KR100688030B1 - Novel luminescent Ir(Ⅲ)-chelated dendritic complexes containing aryl ether-typed dendrons and their synthetic methods - Google Patents

Abstract

The present invention relates to a light-emitting iridium (III) organic metal compound comprising a ligand having a functional formula of Formula 1 and a dendron, and a method of manufacturing the same.

[Formula 1]

Ar ₁ is selected from the following structure,

Ar ₂ is selected from the following structure.

Description

Novel luminescent Ir (III) -chelated dendritic complexes containing aryl ether-typed dendrons and their synthetic methods

Organic Light-Emitting Diodes (OLEDs) have been of considerable interest since they were first reported by CW Tang and JH Burroughes. These materials can be selected from a wide range of organic light emitting materials can produce a full color. Luminescent materials for OLEDs can be classified into organic dyes, coordinated metal compounds and polymers, depending on their molecular structure. In addition, green tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) materials have been successfully used to attract a lot of attention to organometallic complexes. Among them, the iridium (III) complex of 2-phenylpyridine shows high triplet quantum efficiency by spin-orbit coupling between singlet and triplet. In addition, the material has an increased triplet state and high phosphorescence efficiency.

In 1985, KA Kang et al. Described the iridium (III) organometallic material fac -tris (2-phenylpyridinato) Ir (III) {Ir (PPy) ₃ } (PPy = 2-phenylpyridine), which is bound to three organic molecules. Synthesis was performed and the photophysical-chemical properties were studied. The outgassed toluene solvent exhibited a very strong green phosphorescence (λ _max = 514 nm, Φ _p = 0.4) which was emitted from ³ MLCT (metal-to-ligand charge transfer).

In 1999, MA Baldo et al. Made the first OLED using fac -Ir (PPy) ₃ as the luminescent material, and the OLED can obtain about 100% internal quantum efficiency ( η _in ) using both singlet and triplet excitation. there was. Recently, C. Adachi et al. Have obtained nearly 100% internal quantum efficiency ( η _in ) _in green OLEDs.

YJ Su et al. Synthesized a red phosphor, an iridium (III) complex, and also fabricated a device. Among them, the red light-emitting device of Ir (piq-F) ₃ had a good performance as a light emitting layer, and the external quantum efficiency ( η _ex ) was 5.81% at a current density of J = 20 mAcm ^-2 .

An interesting property of the iridium (III) complex is that it is easy to control the phosphorescent color of the desired wavelength band by selecting a ligand that emits light in a specific region. T. Tsuzuki et al. Readily synthesized materials ranging from 513 to 578 nm by controlling the position of perfluorophenyl functional groups for the maximum emission wavelength of iridium complexes. A. Tsuboyama et al. Synthesized iridium (III) complexes with varying ligands with maximum emission wavelengths ranging from 514 to 652 nm. These results have made it possible to realize a display of full colorization using an iridium (III) complex.

On the other hand, luminescent iridium (III) organometallic materials in OLED materials have good properties such as high stability, high luminous efficiency, easy purification, high purity and short excited life, and so on. It's going on. In particular, the phosphor has the possibility of reaching a maximum internal quantum efficiency of 100%, and the light emitting iridium (III) organometallic compound has a very high phosphorescent quantum efficiency. Ir (PPy) ₃ is known as a material having high triplet quantum efficiency due to the increase in the crossover efficiency due to spin-orbital pairing between singlet and triplet. However, phosphors have long lifetimes, triplet-triplet annihilation and non-luminescence due to concentrations that are caused by the interaction of two strong molecules at high current densities or high doping levels. There is an inherent problem that effects are caused. In order to solve such a serious problem and obtain a superior material, the development of a new light emitting iridium (III) organometallic compound is urgently needed.

In order to solve the above problems, the present invention, unlike the conventional method that relies on the characteristics of simple organic molecules composed of light-emitting organic matter which is now widely known, by maximizing the site-isolation effect, very high efficiency It was intended to obtain supramolecular light emitting iridium (III) organometallic compounds having. Accordingly, it is an object of the present invention to provide a compound containing a dendrimer in the aryl-ether form without the interaction between iridium-iridium ions, a light emitting iridium (III) organometallic compound, and a method for preparing the same.

The present invention relates to an iridium (III) organometallic complex having a structure of the following general formula including an aryl-ether type dendrimer, and a method for preparing the same, and including a ligand having a functional formula of Formula 1 and a dendron It is characterized by an iridium (III) organic metal compound.

[Formula 1]

Ar ₁ is selected from the following structure,

Ar ₂ is selected from the following structure.

[R _a in the formula 1 is H, CH ₃ or F and, R _b and R _c are the same as _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CH ₂ OG2, -CH ₂ OG3 or -CH ₂ OG4; R _1, R _2, any one selected from R ₃ and R ₄ are _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CH 2 OG2, -CH ₂ OG3 or -CH ₂ OG4 and the remaining substituents are hydrogen; _{R 5, R 6, R 7} , any one selected from R ₈ and R ₉ is _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CHOG2 , -CH ₂ OG3 or -CH ₂ OG4, and the remaining substituents are hydrogen; _{R 11, R 12, R 13} , any one selected from R ₁₄ and R ₁₅ is _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CHOG2 , -CH ₂ OG3 or -CH ₂ OG4, and the remaining substituents are hydrogen; _{R 10, R 16, R 17} , R 18, R 19, R 20 and R ₂₁ are independently _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 together OG1, -CH ₂ OG2, -CH ₂ OG3 or -CH ₂ OG4; G1, G2, G3 and G4 have the following structure.]

Specific ranges of the compound of formula (1) according to the present invention include the structure of formulas (2) to (59). Substituents of the following formula are the same as those of the formula (1).

[Formula 2]

  [Formula 3]

[Formula 4]

  [Formula 5]

  [Formula 6]

  [Formula 7]

  [Formula 8]

  [Formula 9]

  [Formula 10]

  [Formula 11]

  [Formula 12]

  [Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

  [Formula 18]

  [Formula 19]

  [Formula 20]

  [Formula 21]

  [Formula 22]

  [Formula 23]

  [Formula 24]

  [Formula 25]

  [Formula 26]

  [Formula 27]

  [Formula 28]

  [Formula 29]

  [Formula 30]

  [Formula 31]

       [Formula 32]

  [Formula 33]

       [Formula 34]

  [Formula 35]

  [Formula 36]

  [Formula 37]

  [Formula 38]

  [Formula 39]

[Formula 40]

[Formula 41]

  [Formula 42]

  [Formula 43]

  [Formula 44]

  [Formula 45]

  [Formula 46]

  [Formula 47]

  [Formula 48]

  [Formula 49]

  [Formula 50]

  [Formula 51]

[Formula 52]

[Formula 53]

  [Formula 54]

  [Formula 55]

[Formula 56]

  [Formula 57]

  [Formula 58]

  [Formula 59]

Method for preparing a light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having the functionalities of the compound of formula 1 according to the present invention is a step of synthesizing supermolecules having a light condensing effect by introducing a dendron to an aromatic organic compound and a light-emitting iridium (III) characterized in that it comprises the step of synthesizing the organometallic complex, the method for producing a precursor for preparing the compound of Formula 1 can be prepared through the reaction as described below.

Derivatives of boronic acid are added to bromo derivatives in a non-solvent organic solvent, such as dry THF, in a nitrogen atmosphere.The solution is then slowly added alkyllithium at -78 ^o C and then B (OMe) ₃ is reacted. The aryl-pyridine derivatives containing methoxy could be prepared by mixing methoxyboronic acid derivatives, bromopyridine derivatives, and Pd (PPh ₃ ) ₄ in a nitrogen atmosphere to proceed with the Suzuki CC binding reaction. .

Methylation reactions in aryl-pyridine derivatives containing methoxy could be obtained by reacting methoxy-pyridine derivatives with BBr ₃ at a low temperature of -78 ^o C in a nitrogen atmosphere, aryl-alkyl ether bridge-connected dendrimers (aryl-alkyl ether-bridged dendrimer ) is in a nitrogen atmosphere, under a 18-crown-6 present the hydroxy-aryl pyridine derivatives, was added to the dried K ₂ CO ₃ was added to Gn-Br in acetone solvent, reflux It could be prepared.

Alkyl-alkyl ether-bridged dendrimers are also dried in a nitrogen atmosphere by adding a bromo-alkylphenylpyridine derivative, Gn-OH (5.62 mmole) to dry acetone in the presence of 18-crown-6 in a nitrogen atmosphere. After adding the prepared KOH, it can be prepared by refluxing.

Iridium (III) -organic metal complexes were obtained by reacting a Gn-phenyl-pyridine derivative, Ir (acac) ₃ and a glycerol mixture at 220 ^° C. in a nitrogen atmosphere, containing an iridium (III) -organic metal complex. The polymer blend is polymethyl methacrylate (PMMA), polystyrene (PS), polyimide (PI), polyamide of the iridium (III) -organic metal complex obtained in the above step, and not including or not containing a fluorine substituent. After dissolving 3 to 20% by weight in a polymer material such as polyether and polyester in a chloroform solvent corresponding to 10 times the weight of the total solids, the solution is prepared, and the solution is spin coated to glass and quartz substrates. It was coated on and dried to prepare a thin film of the polymer blend.

The following specifically shows examples for the preparation of intermediates and end products according to the invention. The reaction conditions of each Example were prepared under the same conditions as the preparation method of the compound of each step described in General Preparation Examples.

Previously, ligands as intermediates for preparing the following luminescent iridium (III) organic metal compound including the ligand and the dendron according to the present invention are as shown in Tables 1 to 4 below.

TABLE 1

TABLE 2

TABLE 3

TABLE 4

The following shows examples of specific synthesis for synthesizing intermediates and end products according to the above reaction scheme. In the following chemical formulas and examples, the target product having the 3rd and 4th generation dendrimers has a structural structure very similar to the reaction conditions or starting materials, but has a very similar skeleton, so that the structure of the dendrimer is not specified and is commonly referred to as a 'dendrimer'. It was said.

Hereinafter, the present invention will be described in detail with reference to the following examples, which are not intended to limit the present invention.

Reagents for the preparation of the compounds of the present invention are iridium (III) acetate, 3-bromotoluene, 3-bromoanisole, 3-bromoanisole, trimethylborate, 2.5 mole normal-butyl Lithium solution (2.5M n-BuLi in hexane), benzylbromide, tribromoborane (BBr ₃ ), 2-bromopyridine, N-bromosuccinimide (NBS), isoquinoline (Isoquinoline) , Pyrazole, 3-Iodotoluene, 3-Methoxyphenylmagnesium 0.1 M solution (0.1 M 3-Methoxyphenylmagnesium in THF) is manufactured by Aldrich, 18-crown-6 (1, 4 , 7, 10, 13, 16-hexaoxacyclooctadecane) is manufactured by Acros, Pd (PPh ₃ ) ₄ is manufactured by TCI, 3,5-dihydroxygezyl alcohol (3,5-dihydroxybenzyl alcohol) is manufactured by Fluka, anhydrous ethanol (absolute ethanol) is manufactured by JT Baker, tetrahydrofuran (THF), normal-hexane, toluene, chloroform (CHCl ₃ ), dichloromethane (CH ₂ Cl ₂ ), ethanol, acetone, hydrochloric acid, hydroxide Potassium and anhydrous magnesium sulfate used Samjeon Chemical. In particular, tetrahydrofuran, normal-hexane and toluene solvents are dried under sodium / benzophenone, CHCl ₃ , CH ₂ Cl ₂ is dried under CaH ₂ and P ₂ O ₅ and the solvents are freshly purified and used immediately before use. Other reagents were used without further purification, and the prepared compound was confirmed by ¹ H NMR, ¹³ C NMR, and FT-IR spectroscopic methods. ¹ H NMR was recorded using a Varian 300 spectrometer and all chemical mobility was reported in ppm relative to the internal standard tetramethyl {silaneSi (CH ₃ ) ₄ }. IR spectra were measured on KBr pellets using a Perkin-Elmer spectrometer. The emission spectrum was measured in solution and solid phase with Edinburgh FS920.

[General Production Example 1]

Synthesis of Derivatives of Boronic Acid

In a nitrogen atmosphere, bromo derivative (0.053 mole) is added to 200 mL of dry THF, then the solution is lowered to -78 ^o C and 26 mL (0.065 mol) of 2.5 M n-butyllithium dissolved in n-hexane Take it and add slowly with dice. Hold at this temperature for 2 hours and add 7.3 mL (0.065 mole) of B (OMe) ₃ to the reaction vessel. The reaction solution was allowed to slowly reach room temperature and stirred for about one day. 25 mL of 1 M HCl was slowly added to the reaction vessel and stirred for 1 hour. The reaction was extracted three times with 150 mL of dichloromethane, and the combined organic layers were washed with 250 mL of water and dried over anhydrous magnesium sulfate. Removal of the solvent gave a white solid, which was washed thoroughly with n-hexane to remove impurities.

[General Production Example 2]

Synthesis of Aryl-pyridine Derivatives Containing Methoxy by Suzuki C-C Coupling

In a nitrogen atmosphere, methoxyboronic acid derivative (0.0329 mole), bromopyridine derivative (0.0285 mole) and Pd (PPh ₃ ) ₄ (0.692 mmole) were added to a 250 mL three-necked flask. 100 mL of toluene and 30 mL of aqueous 2 MK ₂ CO ₃ were added and the reaction solution was refluxed with stirring for 48 hours under nitrogen. After the reaction, the flask was cooled to room temperature, the mixture was extracted three times with 100 mL of dichloromethane, the combined organic layers were washed twice with water (250 mL) and dried over anhydrous magnesium sulfate. Removal of the solvent gave a brown oily phase which was separated and purified by column chromatography eluting with chloroform.

[General Production Example 3]

Methylation reaction on aryl-pyridine derivatives including methoxy

In a nitrogen atmosphere, methoxy-pyridine derivative (6.48 mmole) and 20 mL of dry dichloromethane were added to a three-necked flask. This solution was cooled to -78 ^o C and BBr ₃ (1.53 mL, 16.18 mmole) was added slowly to the reaction vessel. The reaction was allowed to slowly reach room temperature and then stirred for 1 day. The resulting product was cooled with ice and slowly adjusted to pH 7 with 2 MK ₂ CO ₃ aqueous solution. The reaction mixture was extracted three times with 50 mL of ethyl acetate. The organic layer was washed twice with water and dried over anhydrous magnesium sulfate. Removal of the solvent gave a brown solid, which was separated and purified by column chromatography eluting with acetone.

[General Production Example 4]

Process for preparing aryl-alkyl ether-bridged dendrimer

Under nitrogen atmosphere, hydroxy-arylpyridine derivative (1.168 mmole), Gn-Br (1.287 mmole) and 18-crown-6 (0.034 mmole) are dissolved in 50 mL of acetone, and dried K ₂ CO ₃ (0.3 g) Added. The reaction mixture was refluxed for 48 hours, cooled slowly to room temperature and the solid was filtered off. The filtrate was diluted with 100 mL of dichloromethane, washed with 50 mL of water, and the organic layer was dried over anhydrous magnesium sulfate. Removal of the solvent gave a brown oil, which was purified by column chromatography eluting with chloroform.

[General Production Example 5]

Process for preparing alkyl-alkyl ether-bridged dendrimer

In a nitrogen atmosphere, brmo-alkylphenylpyridine derivatives (3.22 mmole), Gn-OH (5.62 mmole) and 18-crown-6 (0.0567 mmole) are dissolved in 50 mL of dry acetone, followed by drying KOH (0.14 g). Added. The reaction mixture was refluxed at 70 ^° C. for 48 hours and after slowly cooling to room temperature, the solids were filtered off. This filtrate was diluted with 100 mL of dichloromethane and washed with 50 mL of water. The organic layer is dried over anhydrous magnesium sulfate and the solvent is removed to give a brown oil. It was isolated and purified by column chromatography eluting with ethyl acetate and n-hexane.

[General Production Example 6]

Synthesis of Iridium (III) -Organic Metal Complexes

In a nitrogen atmosphere, Gn-phenyl-pyridine derivative (2.051 mmole), Ir (acac) ₃ (0.319 mmole) and 15 mL of glycerol were added to a three neck flask. The mixture was reacted at 220 ^° C. for 48 hours and then cooled to room temperature. This mixture was added 200 mL of water and extracted three times with 100 mL of dichloromethane. The combined organic layers are dried over anhydrous magnesium sulfate and the solvent is removed to give a brown oil. It was isolated and purified by column chromatography eluting with dichloromethane.

[General Production Example 7]

Polymer Blends Containing Iridium (III) -Organic Metal Complexes

Polymer materials such as polymethyl methacrylate (PMMA), polystyrene (PS), polyimide (PI), polyamide, polyether, polyester, etc., with or without iridium (III) -organic metal complex 3 wt%, 5 wt%, 10 wt%, 15 wt%, 18 wt%, 20 wt% in a chloroform solvent equivalent to 10 times the weight of the total solids to form a solution, and then spin the solution A thin film of polymer blend was prepared by coating and drying the glass and quartz substrates by coating method.

Example 1

2- (2,3 or 4-methoxy-phenyl) pyridine

2- (2,3 or 4-Methoxyphenyl) -pyridine

4, 5 or 6-methoxybenzeneboronic acid and 2-bromopyridine were synthesized using a palladium (0) catalyst. [Ligand 1]

2- (3-methoxy-phenyl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.69 (tt, 1H, J = 1.5), 7.72-7.75 (m, 2H), 7.53-7.60 (m, 2H) , 7.36-7.41 (t, 1H, J = 7.8), 7.20-7.26 (m, 1H), 6.95-6.99 (m, 1H), 3.89 (s, 1H).

Example 2

2- (2-OG1-phenyl) pyridine

2- (2-OG1-phenyl) pyridine

The reaction of 2- (2-Hydroxy-phenyl) -pyridine, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.29-7.44 (m, 10H), 7.20-7.25 ( m, 1H), 7.02 (m, 1H), 6.98 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.86 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 ( t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H). EI (m / z): 898 (M ⁺ ).

Example 3

2- (3-OG1-phenyl) pyridine

2- (3-OG1-phenyl) pyridine

The reaction of 2- (3-Hydroxy-phenyl) -pyridine, G1-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.67-7.73 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.29-7.44 (m, 10H), 7.20-7.23 (m, 1H), 7.00 (m, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H ).

Example 4

2- (4-OG1-phenyl) pyridine

2- (4-OG1-phenyl) pyridine

The reaction of 2- (4-Hydroxy-phenyl) -pyridine, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 7.88 (d, 2H, J = 1.2 Hz), 7.66 (t, 1H, J = 1.2), 7.67-7.74 (m, 2H), 7.48 (d, 1H, J = 7.8), 7.30-7.49 (m, 11H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H). EI (m / z): 898 (M ⁺ ).

Example 5

2- (2-OG2-phenyl) pyridine

2- (2-OG2-phenyl) pyridine

The reaction of 2- (2-Hydroxy-phenyl) -pyridine, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 20H), 7.20 (t , 1H), 7.02 (t, 1H), 6.92 (t, 1H), 6.85 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 6

2- (3-OG2-phenyl) pyridine

2- (3-OG2-phenyl) pyridine

The reaction of 2- (3-Hydroxy-phenyl) -pyridine, G2-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.29-7.43 (m, 20H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s , 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 7

2- (4-OG2-phenyl) pyridine

2- (4-OG2-phenyl) pyridine

The reaction of 2- (4-Hydroxy-phenyl) -pyridine, G2-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 20H), 7.25 (t , 1H), 7.02 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 8

2- (2-OG3-phenyl) pyridine

2- (2-OG3-phenyl) pyridine

The reaction of 2- (2-Hydroxy-phenyl) -pyridine, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 40H), 7.20 (t , 1H), 7.02 (t, 1H), 6.92 (t, 1H), 6.85 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

Example 9

2- (3-OG3-phenyl) pyridine

2- (3-OG3-phenyl) pyridine

The reaction of 2- (3-Hydroxy-phenyl) -pyridine, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.29-7.43 (m, 40H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 10

2- (4-OG3-phenyl) pyridine

2- (4-OG3-phenyl) pyridine

The reaction of 2- (4-Hydroxy-phenyl) -pyridine, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 40H), 7.25 (t , 1H), 7.02 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 11

2- (2-OG4-phenyl) pyridine

2- (2-OG4-phenyl) pyridine

The reaction of 2- (2-Hydroxy-phenyl) -pyridine, G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 80H), 7.20 (t , 1H), 7.02 (t, 1H), 6.92 (t, 1H), 6.85 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 ( s, 32H), 4.95-4.92 (m, 28H).

Example 12

2- (3-OG4-phenyl) pyridine

2- (3-OG4-phenyl) pyridine

The reaction of 2- (3-Hydroxy-phenyl) -pyridine, G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.29-7.43 (m, 80H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 ( m, 28 H).

Example 13

2- (4-OG4-phenyl) pyridine

2- (4-OG4-phenyl) pyridine

The reaction of 2- (4-Hydroxy-phenyl) -pyridine, G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 80H), 7.25 (t , 1H), 7.02 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 14

2- (2-G1-oxymethylenephenyl) -pyridine

2- (2-G1-oxymethylenephenyl) -pyridine

2- (2-Bromomethylphenyl) -pyridine, G1-OH and 18-crown-6 were dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G1-OH (R'-OR) formation reaction by adding KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.30-7.49 (m, 12H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.98 (t, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 15

2- (3-G1-oxymethylenephenyl) -pyridine

2- (3-G1-oxymethylenephenyl) -pyridine

2- (35-Bromomethylphenyl) -pyridine, G1-OH and 18-crown-6 dissolved in acetone and synthesized by the reaction of bromomethylphenyl-pyridine and G1-OH (R'-OR) formation by adding KOH . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.66 (t, 1H, J = 1.2), 8.00 (s, 1H), 7.90-7.92 (m, 1H), 7.70-7.72 (m, 2H), 7.30-7.49 ( m, 11H), 7.18-7.23 (m, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2 H).

Example 16

2- (4-G1-oxymethylenephenyl) -pyridine

2- (4-G1-oxymethylenephenyl) -pyridine

2- (4-Bromomethylphenyl) -pyridine, G1-OH and 18-crown-6 dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G1-OH (R'-OR) formation reaction by adding KOH . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 7.88 (d, 2H, J = 1.2 Hz), 7.66 (t, 1H, J = 1.2), 7.67-7.74 (m, 2H), 7.30 -7.49 (m, 12H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H). EI (m / z): 898 (M ⁺ ).

Example 17

2- (2-G2-oxymethylenephenyl) -pyridine

2- (2-G2-oxymethylenephenyl) -pyridine

2- (2-Bromomethylphenyl) -pyridine, G2-OH and 18-crown-6 dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G2-OH ether (R'-OR) formation by adding KOH . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.27-7.47 (m, 21H), 7.20-7.25 ( m, 1H), 7.02 (m, 1H), 6.98 (t, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4 ), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 18

2- (3-G2-oxymethylenephenyl) -pyridine

2- (3-G2-oxymethylenephenyl) -pyridine

2- (3-Bromomethylphenyl) -pyridine, G2-OH and 18-crown-6 were dissolved in acetone and synthesized by the reaction of bromomethylphenyl-pyridine and G2-OH (R'-OR) formation reaction by adding KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 2H), 7.27-7.47 ( m, 21H), 7.13-7.20 (m, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t , 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 19

2- (4-G2-oxymethylenephenyl) -pyridine

2- (4-G2-oxymethylenephenyl) -pyridine

2- (4-Bromomethylphenyl) -pyridine, G2-OH and 18-crown-6 were synthesized through the reaction of bromomethylphenyl-pyridine and G2-OH ether (R'-OR) formation by dissolving in acetone and adding KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.27-7.47 (m, 21H), 7.02 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 20

2- (2-G3-oxymethylenephenyl) -pyridine

2- (2-G3-oxymethylenephenyl) -pyridine

2- (2-Bromomethylphenyl) -pyridine, G3-OH and 18-crown-6 were synthesized through the reaction of bromomethylphenyl-pyridine and G3-OH ether (R'-OR), which was dissolved in acetone and reacted with KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.27-7.41 (m, 40H), 7.20-7.25 ( m, 2H), 7.02 (m, 1H), 6.98 (t, 1H), .67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 21

2- (3-G3-oxymethylenephenyl) -pyridine

2- (3-G3-oxymethylenephenyl) -pyridine

2- (3-Bromomethylphenyl) -pyridine, G3-OH and 18-crown-6 were synthesized through the reaction of bromomethylphenyl-pyridine and G3-OH ether (R'-OR), which was dissolved in acetone and reacted with KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 2H), 7.27-7.41 ( m, 40H), 7.13-7.20 (m, 3H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t , 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 22

2- (4-G3-oxymethylenephenyl) -pyridine

2- (4-G3-oxymethylenephenyl) -pyridine

2- (4-Bromomethylphenyl) -pyridine, G3-OH and 18-crown-6 dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G3-OH ether (R'-OR) formation by adding KOH . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.27-7.41 (m, 41H), 7.02 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 23

2- (2-G4-oxymethylenephenyl) -pyridine

2- (2-G4-oxymethylenephenyl) -pyridine

2- (2-Bromomethylphenyl) -pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine with G4-OH (R'-OR) formation reaction by adding KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.29-7.44 (m, 80H), 7.20-7.25 ( m, 2H), 7.02 (m, 1H), 6.98 (t, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 24

2- (3-G4-oxymethylenephenyl) -pyridine

2- (3-G4-oxymethylenephenyl) -pyridine

2- (3-Bromomethylphenyl) -pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G4-OH (R'-OR) formation reaction by adding KOH. . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 2H), 7.29-7.43 ( m, 80H), 7.13-7.20 (m, 3H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H ), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 25

2- (4-G4-oxymethylenephenyl) -pyridine

2- (4-G4-oxymethylenephenyl) -pyridine

2- (4-Bromomethylphenyl) -pyridine, G4-OH and 18-crown-6 dissolved in acetone and synthesized through the reaction of bromomethylphenyl-pyridine and G4-OH (R'-OR) formation reaction by adding KOH . [Ligand 1]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 81H), 7.02 (d , 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 26

2- (2 ', 3' or 4'-methoxy-biphenyl-3 or 4-yl) pyridine

2- (2 ', 3' or 4'-Methoxy-biphenyl-3 or 4-yl) pyridine

Suzuki C-C coupling of 2-bromopyridine with 2 ', 3' or 4'-methoxy-biphenyl-3 or 4-boronic acid was synthesized. [Ligand 2]

2- (4'-methoxy-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H, J = 8.4), 8.04 (d, 1H, J = 2.1 Hz) , 7.78-7.84 (m, 2H), 7.57-7.62 (m, 2H), 6.93-7.13 (m, 5H), 3.80 (s, 3H).

Example 27

2- (2'-OG1-biphenyl-3 or 4-yl) pyridine

2- (2'-OG1-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (2'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G1-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (2'-OG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.44 (m, 12H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 28

2- (3'-OG1-biphenyl-3 or 4-yl) pyridine

2- (3'-OG1-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (3'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G1-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (3'-OG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (m, 2H), 7.29-7.44 (m, 11H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (m, 2H), 6.93 (s, 1H), 6.72 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 29

2- (4'-OG1-biphenyl-3 or 4-yl) pyridine

2- (4'-OG1-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (4'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G1-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (4'-OG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.29-7.44 (m, 11H), 7.32 (d, 2H), 6.98 (t, 1H), 6.79 (d, 2H), 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 30

2- (2'-OG2-biphenyl-3 or 4-yl) pyridine

2- (2'-OG2-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (2'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G2-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (2'-OG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (m, 2H), 7.29-7.44 (m, 22H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H) .

Example 31

2- (3'-OG2-biphenyl-3 or 4-yl) pyridine

2- (3'-OG2-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (3'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G2-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (3'-OG2-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 21H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (m, 2H), 6.93 (s, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H) , 4.99 (s, 4 H).

Example 32

2- (4'-OG2-biphenyl-3 or 4-yl) pyridine

2- (4'-OG2-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (4'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G2-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (4'-OG2-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.45 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 23H), 6.98 (t, 1H), 6.79 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 33

2- (2'-OG3-biphenyl-3 or 4-yl) pyridine

2- (2'-OG3-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (2'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G3-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (2'-OG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 42H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 34

2- (3'-OG3-biphenyl-3 or 4-yl) pyridine

2- (3'-OG3-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (3'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G3-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (3'-OG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 41H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 35

2- (4'-OG3-biphenyl-3 or 4-yl) pyridine

2- (4'-OG3-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (4'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G3-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (4'-OG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.29-7.43 (m, 40H), 7.32 (d, 2H), 6.98 (t, 1H), 6.79 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 36

2- (2'-OG4-biphenyl-3 or 4-yl) pyridine

2- (2'-OG4-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (2'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G4-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (2'-OG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (m, 2H), 7.29-7.43 (m, 82H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.65 -6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 37

2- (3'-OG4-biphenyl-3 or 4-yl) pyridine

2- (3'-OG4-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (3'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G4-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (3'-OG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 81H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (m, 2H), 6.93 (s, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 38

2- (4'-OG4-biphenyl-3 or 4-yl) pyridine

2- (4'-OG4-biphenyl-3 or 4-yl) pyridine

Reaction of 2- (4'-Hydroxy-biphenyl-3 or 4-yl) -pyridine, G4-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-methyldendron Synthesized. [Ligand 2]

2- (4'-OG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 ( d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.29-7.43 (m, 82H), 6.98 (t, 1H), 6.79 (d, 2H), 6.65-6.48 (m, 45H) , 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 39

2- (2'-methyleneoxyG1-biphenyl-3 or 4-yl) pyridine

2- (2'-MethyleneoxyG1-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G1-OH by dissolving 2- (2'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G1-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (2'-methyleneoxyG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.31 (d, 1H), 7.30-7.49 (m, 11H), 77.05 (t, 1H) , 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

Example 40

2- (3'-methyleneoxyG1-biphenyl-3-yl) pyridine

2- (3'-MethyleneoxyG1-biphenyl-3-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G1-OH by dissolving 2- (3'-Bromomethylbiphenyl-3-yl) pyridine, G1-OH and 18-crown-6 in acetone and adding KOH Through synthesis. [Ligand 2]

2- (3'-methyleneoxyG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.30-7.49 (m, 11H), 7.15 (t, 1H), 7.05 (d, 1H) , 6.98 (m, 2H), 6.93 (s, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H) , 4.53 (s, 2 H).

Example 41

2- (3'-methyleneoxyG1-biphenyl-4-yl) pyridine

2- (3'-MethyleneoxyG1-biphenyl-4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G1-OH by dissolving 2- (3'-Bromomethylbiphenyl-4-yl) pyridine, G1-OH and 18-crown-6 in acetone and adding KOH Through synthesis. [Ligand 2]

2- (3'-methyleneoxyG1-biphenyl-4-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.05 (d, 2H), 7.57 (d, 2H), 7.54 (d, 1H), 7.50 (t, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.30-7.49 (m, 11H), 7.29 (d, 1H), 7.28 (s, 1H) , 6.98 (t, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H) .

Example 42

2- (4'-methyleneoxyG1-biphenyl-3 or 4-yl) pyridine

2- (4'-MethyleneoxyG1-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G1-OH by dissolving 2- (4'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G1-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (4'-methyleneoxyG1-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.30-7.49 (m, 11H), 7.32 (d, 2H), 6.98 (t, 1H) , 6.79 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H) .

Example 43

2- (2'-methyleneoxyG2-biphenyl-3 or 4-yl) pyridine

2- (2'-MethyleneoxyG2-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G2-OH by dissolving 2- (2'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G2-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (2'-methyleneoxyG2-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.31 (d, 1H), 7.27-7.47 (m, 21H), 7.05 (t, 1H) , 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 44

2- (3'-methyleneoxyG2-biphenyl-3 or 4-yl) pyridine

2- (3'-MethyleneoxyG2-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G2-OH by dissolving 2- (3'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G2-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (3'-methyleneoxyG2-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.27-7.47 (m, 22H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H) , 6.97 (d, 1H), 6.93 (s, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 ( t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 45

2- (4'-methyleneoxyG2-biphenyl-3 or 4-yl) pyridine

2- (4'-MethyleneoxyG2-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G2-OH by dissolving 2- (4'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G2-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (4'-methyleneoxyG2-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.27-7.47 (m, 22H), 7.32 (d, 2H), 6.98 (t, 1H), 6.79 (d, 2H) , 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H ), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 46

2- (2'-methyleneoxyG3-biphenyl-3 or 4-yl) pyridine

2- (2'-MethyleneoxyG3-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G3-OH by dissolving 2- (2'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G3-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (2'-methyleneoxyG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.27-7.41 (m, 42H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H) , 6.79 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4 ), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 47

2- (3'-methyleneoxyG3-biphenyl-3 or 4-yl) pyridine

2- (3'-MethyleneoxyG3-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G3-OH by dissolving 2- (3'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G3-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (3'-methyleneoxyG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.27-7.41 (m, 41H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H) , 6.97 (d, 1H), 6.93 (s, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 ( t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 48

2- (4'-methyleneoxyG3-biphenyl-3 or 4-yl) pyridine

2- (4'-MethyleneoxyG3-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G3-OH by dissolving 2- (4'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G3-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (4'-methyleneoxyG3-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.27-7.41 (m, 42H), 6.98 (t, 1H), 6.79 (d, 2H) , 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H ), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 49

2- (2'-methyleneoxyG4-biphenyl-3 or 4-yl) pyridine

2- (2'-MethyleneoxyG4-biphenyl-3 or 4-yl) pyridine

Produces ether (R'-OR) of bromomethylphenyl pyridine and G4-OH by dissolving 2- (2'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G4-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (2'-methyleneoxyG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.44 (m, 82H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H) , 6.79 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 50

2- (3'-methyleneoxyG4-biphenyl-3 or 4-yl) pyridine

2- (3'-MethyleneoxyG4-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G4-OH by dissolving 2- (3'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G4-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (3'-methyleneoxyG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.29-7.44 (m, 81H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H) , 6.97 (d, 1H), 6.93 (s, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 51

2- (4'-methyleneoxyG4-biphenyl-3 or 4-yl) pyridine

2- (4'-MethyleneoxyG4-biphenyl-3 or 4-yl) pyridine

Formation of ether (R'-OR) of bromomethylphenyl pyridine and G4-OH by dissolving 2- (4'-Bromomethylbiphenyl-3 or 4-yl) pyridine, G4-OH and 18-crown-6 in acetone and adding KOH Synthesis via reaction. [Ligand 2]

2- (4'-methyleneoxyG4-biphenyl-3-yl) pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.29-7.44 (m, 83H), 6.98 (t, 1H), 6.79 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 52

2- (5-methoxy-thiophen-2-yl) pyridine

2- (5-Methoxy-thiophen-2-yl) pyridine

5-methoxy-thiophene-2-boronic acid and 2-bromopyridine were synthesized using a palladium (0) catalyst. [Regal 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.31 (t, 1H), 6.52 (d, 1H), 6.00 (d, 1H ), 3.83 (s, 3 H).

Example 53

2- (5-OG1-thiophen-2-yl) pyridine

2- (5-OG1-thiophen-2-yl) pyridine

2- (5-hydroxy-thiophen-2-yl) pyridine, G1-Br and 18-crown-6 were synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 11H), 6.71 (m, 4H), 6.23 (d , 1H), 6.57 (t, 1H, J = 2.4), 6.52 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 54

2- (5-OG2-thiophen-2-yl) pyridine

2- (5-OG2-thiophen-2-yl) pyridine

The reaction of 2- (5-hydroxy-thiophen-2-yl) pyridine, G2-Br and 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 21H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.52 (d, 1H), 6.24 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 55

2- (5-OG3-thiophen-2-yl) pyridine

2- (5-OG3-thiophen-2-yl) pyridine

2- (5-hydroxy-thiophen-2-yl) pyridine, G3-Br and 18-crown-6 were synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 41H), 6.65-6.52 (m, 21H), 6.24 (d, 1H), 5.09 (m, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 56

2- (5-OG4-thiophen-2-yl) pyridine

2- (5-OG4-thiophen-2-yl) pyridine

2- (5-hydroxy-thiophen-2-yl) pyridine, G4Br, and 18-crown-6 were synthesized by ether (R'-O-R) reaction of hydroxy-aryl and bromo-alkylpyridine. [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 81H), 6.65-6.48 (m, 46H), 6.24 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 57

2- (5-methyleneoxyG1-thiophen-2-yl) pyridine

2- (5-MethyleneoxyG1-thiophen-2-yl) pyridine

Ether of bromomethylthiophen-2-yl-pyridine and G1-OH (2-'5-Bromomethylthiophen-2-yl) pyridine, G1-OH and 18-crown-6 dissolved in acetone and added with KOH to react ) Through synthesis reaction. [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 11H), 6.55 (m, 2H), 6.24 (d , 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 58

2- (5-methyleneoxyG2-thiophen-2-yl) pyridine

2- (5-MethyleneoxyG2-thiophen-2-yl) pyridine

Ether of bromomethylthiophen-2-yl-pyridine and G2-OH (2-'5-Bromomethylthiophen-2-yl) pyridine, G2-OH and 18-crown-6 dissolved in acetone and added with KOH to react ) Through synthesis reaction. [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 20H), 7.02 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.50 (t, 2H, J = 2.4), 6.24 (d, 1H) 4.99 (s , 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 59

2- (5-methyleneoxyG3-thiophen-2-yl) pyridine

2- (5-MethyleneoxyG3-thiophen-2-yl) pyridine

Ether of bromomethylthiophen-2-yl-pyridine and G3-OH (2-'5-Bromomethylthiophen-2-yl) pyridine, G3-OH and 18-crown-6 dissolved in acetone and added with KOH to react ) Through synthesis reaction. [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 40H), 7.02 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.24 (d, 1H), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 60

2- (5-methyleneoxyG4-thiophen-2-yl) pyridine

2- (5-MethyleneoxyG4-thiophen-2-yl) pyridine

Ether (R'-OR) of bromomethylthiophen-2-yl-pyridine and G4-OH which dissolve 2- (5-Bromomethylthiophen-2-yl) pyridine, G4-OH and 18-crown-6 in acetone and add KOH to react ) Through synthesis reaction. [Ligand 3]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 80H), 7.02 (d, 2H), 6.62-6.67 (m, 43H), 6.58 (d, 2H, J = 2.4), 6.24 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

Example 61

2- [5- (2, 3, or 4-methoxy-phenyl) thiophen-2-yl] pyridine

2- [5- (2, 3 or 4-Methoxy-phenyl) thiophen-2-yl] pyridine

5- (2, 3 or 4-methoxyphenyl) thiophene-2-boronic acid and 2-bromopyridine were synthesized using a palladium (0) catalyst. [Ligand 4]

2- [5- (2-methoxy-phenyl) thiophen-2-yl] pyridine: ¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.37 (d, 1H), 7.30 (t, 1H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (t, 1H), 6.84 (d, 1H), 3.73 (s, 3H) ).

Example 62

2- [5- (2-OG1-phenyl) thiophen-2-yl] pyridine

2- [5- (2-OG1-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (2-Hydroxy-phenyl) thiophen-2-yl] pyridine, G1-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 12H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.57 (t, 1H, J = 2.4) , 5.08 (s, 2H), 5.03 (s, 4H).

Example 63

2- [5- (3-OG1-phenyl) thiophen-2-yl] pyridine

2- [5- (3-OG1-phenyl) thiophen-2-yl] pyridine

The reaction of 2- [5- (3-Hydroxy-phenyl) thiophen-2-yl] pyridine, G1-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 10H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.68 (d, 1H), 6.57 (t , 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 64

2- [5- (4-OG1-phenyl) thiophen-2-yl] pyridine

2- [5- (4-OG1-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (4-Hydroxy-phenyl) thiophen-2-yl] pyridine, G1-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 13H), 7.00 (d, 2H), 6.79 (d , 2H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H) .

Example 65

2- [5- (2-OG2-phenyl) thiophen-2-yl] pyridine

2- [5- (2-OG2-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (2-Hydroxy-phenyl) thiophen-2-yl] pyridine, G2-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 22H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 66

2- [5- (3-OG2-phenyl) thiophen-2-yl] pyridine

2- [5- (3-OG2-phenyl) thiophen-2-yl] pyridine

The reaction of 2- [5- (3-Hydroxy-phenyl) thiophen-2-yl] pyridine, G2-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 22H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 67

2- [5- (4-OG2-phenyl) thiophen-2-yl] pyridine

2- [5- (4-OG2-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (4-Hydroxy-phenyl) thiophen-2-yl] pyridine, G2-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 23H), 7.00 (d, 2H), 6.79 (d , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 68

2- [5- (2-OG3-phenyl) thiophen-2-yl] pyridine

2- [5- (2-OG3-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (2-Hydroxy-phenyl) thiophen-2-yl] pyridine, G3-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 42H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H).

Example 69

2- [5- (3-OG3-phenyl) thiophen-2-yl] pyridine

2- [5- (3-OG3-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (3-Hydroxy-phenyl) thiophen-2-yl] pyridine, G3-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 42H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H).

Example 70

2- [5- (4-OG3-phenyl) thiophen-2-yl] pyridine

2- [5- (4-OG3-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (4-Hydroxy-phenyl) thiophen-2-yl] pyridine, G3-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 43H), 7.00 (d, 2H), 6.79 (d , 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 71

2- [5- (2-OG4-phenyl) thiophen-2-yl] pyridine

2- [5- (2-OG4-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (2-Hydroxy-phenyl) thiophen-2-yl] pyridine, G4-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H).

Example 72

2- [5- (3-OG4-phenyl) thiophen-2-yl] pyridine

2- [5- (3-OG4-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (3-Hydroxy-phenyl) thiophen-2-yl] pyridine, G4-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H).

Example 73

2- [5- (4-OG4-phenyl) thiophen-2-yl] pyridine

2- [5- (4-OG4-phenyl) thiophen-2-yl] pyridine

Reaction of 2- [5- (4-Hydroxy-phenyl) thiophen-2-yl] pyridine, G4-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 83H), 7.00 (d, 2H), 6.79 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 74

2- [5- (2-methyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (2-MethyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (2-Bromomethylphenyl) thiophen-2-yl] pyridine, G1-OH and 18-crown-6 were dissolved in acetone and synthesized by ether (R'-OR) reaction to add KOH and react. . [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 12H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.57 (t, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2 H).

Example 75

2- [5- (3-methyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (3-MethyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (3-Bromomethylphenyl) thiophen-2-yl] pyridine, G1-OH and 18-crown-6 were synthesized through ether (R'-OR) formation reaction in which acetone was dissolved and KOH was added for reaction. . [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 12H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.57 (t, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2 H).

Example 76

2- [5- (4-methyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (4-MethyleneoxyG1-phenyl) thiophen-2-yl] pyridine

2- [5- (4-Bromomethylphenyl) thiophen-2-yl] pyridine, G1-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 13H), 7.00 (d, 2H), 6.79 (d , 2H), 6.57 (t, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 77

2- [5- (2-methyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (2-MethyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (2-Bromomethylphenyl) thiophen-2-yl] pyridine, G2-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl 3): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 22H), 7.15 (t, 1H), 7.04 (t, 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 78

2- [5- (3-methyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (3-MethyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (3-Bromomethylphenyl) thiophen-2-yl] pyridine, G2-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 22H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 79

2- [5- (4-methyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (4-MethyleneoxyG2-phenyl) thiophen-2-yl] pyridine

2- [5- (4-Bromomethylphenyl) thiophen-2-yl] pyridine, G2-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 23H), 7.00 (d, 2H), 6.79 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 80

2- [5- (2-methyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (2-MethyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (2-Bromomethylphenyl) thiophen-2-yl] pyridine, G3-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 42H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 81

2- [5- (3-methyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (3-MethyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (3-Bromomethylphenyl) thiophen-2-yl] pyridine, G3-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 42H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 82

2- [5- (4-methyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (4-MethyleneoxyG3-phenyl) thiophen-2-yl] pyridine

2- [5- (4-Bromomethylphenyl) thiophen-2-yl] pyridine, G3-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 43H), 7.00 (d, 2H), 6.79 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 83

2- [5- (2-methyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (2-MethyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (2-Bromomethylphenyl) thiophen-2-yl] pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.15 (t, 1H), 7.04 (t , 1H), 7.00 (d, 2H), 6.95 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 84

2- [5- (3-methyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (3-MethyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (3-Bromomethylphenyl) thiophen-2-yl] pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 85

2- [5- (4-methyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (4-MethyleneoxyG4-phenyl) thiophen-2-yl] pyridine

2- [5- (4-Bromomethylphenyl) thiophen-2-yl] pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 4]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 83H), 7.00 (d, 2H), 6.79 (d , 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 86

2- [7- (4-methoxy-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-Methoxy-phenyl) -9 H -fluoren-2-yl] pyridine

The desired product was synthesized by CC coupling reaction of 7- (4-Methoxy-phenyl) -9 H- fluoren-2-boronic acid with 2-bromopyridine. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 6.98 (t, 1H), 6.83 (d, 2H), 3.87 (s, 1H), 3.83 (s, 3H) .

Example 87

2- [7- (4-OG1-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-OG1-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] pyridine, G1-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'-OR of ) Through synthesis reaction. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.28 (s, 1H), 8.12 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.44 (m, 10H), 6.98 (t, 1H), 6.83 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.87 (s, 1H).

Example 88

2- [7- (4-OG2-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-OG2-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] pyridine, G2-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'-OR of ) Through synthesis reaction. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.46 (t, 1H), 7.29-7.43 (m, 20H), 6.98 (t, 1H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.87 ( s, 1 H).

Example 89

2- [7- (4-OG3-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-OG3-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] pyridine, G3-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'-OR of ) Through synthesis reaction. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 40H), 6.98 (t, 1H), 6.83 (d, 2H), 6.65-6.52 ( m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.87 (s, 1H).

Example 90

2- [7- (4-OG4-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-OG4-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] pyridine, G4-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'-OR of ) Through synthesis reaction. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 80H), 6.98 (t, 1H), 6.83 (d, 2H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.87 (s, 1H).

Example 91

2- [7- (4-methyleneoxyG1-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-MethyleneoxyG1-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-CH ₂ Br-phenyl) -9 H- fluoren-2-yl] pyridine, G1-OH and 18-crown-6 were dissolved in acetone and synthesized by addition of KOH. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.30-7.49 (m, 11H), 6.98 (t, 1H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.87 (s, 1H).

Example 92

2- [7- (4-methyleneoxyG2-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-MethyleneoxyG2-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-CH ₂ Br-phenyl) -9 H- fluoren-2-yl] pyridine, G2-OH and 18-crown-6 were dissolved in acetone and synthesized by addition of KOH. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.27-7.47 (m, 21H), 6.98 (t, 1H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.87 (s, 1H).

Example 93

2- [7- (4-methyleneoxyG3-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-MethyleneoxyG3-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-CH ₂ Br-phenyl) -9 H- fluoren-2-yl] pyridine, G3-OH and 18-crown-6 were dissolved in acetone and synthesized by addition of KOH. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.27-7.41 (m, 41H), 6.98 (t, 1H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 1H).

Example 94

2- [7- (4-methyleneoxyG4-phenyl) -9 H -floren-2-yl] pyridine

2- [7- (4-MethyleneoxyG4-phenyl) -9 H -fluoren-2-yl] pyridine

2- [7- (4-CH ₂ Br-phenyl) -9 H- fluoren-2-yl] pyridine, G4-OH and 18-crown-6 were dissolved in acetone and synthesized by adding KOH. [Ligand 5]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (t, 1H), 6.83 (d, 2H), 6.62-6.67 ( m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 ( s, 1 H).

Example 95

2- (6-methoxy-benzo [ b ] thiophen-2-yl) pyridine

2- (6-Methoxy-benzo [ b ] thiophen-2-yl) pyridine

The desired product was synthesized by C-C coupling reaction of 6-Methoxy-benzo [b] thiophen-2-boronic acid and 2-bromopyridine. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.42 (s, 1H), 7.33 (m, 2H ), 3.73 (s, 1 H).

Example 96

2- (6-OG1-benzo [ b ] thiophen-2-yl) pyridine

2- (6-OG1-benzo [ b ] thiophen-2-yl) pyridine

Reaction of 2- (6-Hydroxy-benzo [ b ] thiophen-2-yl) pyridine, G1-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine Synthesized. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.44 (m, 13H), 6.72 (d , 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.73 (s, 1H) .

Example 97

2- (6-OG2-benzo [ b ] thiophen-2-yl) pyridine

2- (6-OG2-benzo [ b ] thiophen-2-yl) pyridine

Reaction of 2- (6-Hydroxy-benzo [ b ] thiophen-2-yl) pyridine, G2-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine Synthesized. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 23H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.73 (s, 1 H).

Example 98

2- (6-OG3-benzo [ b ] thiophen-2-yl) pyridine

2- (6-OG3-benzo [ b ] thiophen-2-yl) pyridine

Reaction of 2- (6-Hydroxy-benzo [ b ] thiophen-2-yl) pyridine, G3-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine Synthesized. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.63 (d, 1H), 7.83 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 43H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.73 (s, 1H).

Example 99

2- (6-OG4-benzo [ b ] thiophen-2-yl) pyridine

2- (6-OG4-benzo [ b ] thiophen-2-yl) pyridine

Reaction of 2- (6-Hydroxy-benzo [ b ] thiophen-2-yl) pyridine, G4-Br and 18-crown-6 through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine Synthesized. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.81 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 83H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.73 (s, 1H).

Example 100

2- (6-methyleneoxyG1-benzo [ b ] thiophen-2-yl) pyridine

2- (6-MethyleneoxyG1-benzo [ b ] thiophen-2-yl) pyridine

2- (6-Bromomethyl-benzo [ b ] thiophen-2-yl) pyridine, G1-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 13H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.73 (s, 1H).

Example 101

2- (6-methyleneoxyG2-benzo [ b ] thiophen-2-yl) pyridine

2- (6-MethyleneoxyG2-benzo [ b ] thiophen-2-yl) pyridine

2- (6-Bromomethyl-benzo [ b ] thiophen-2-yl) pyridine, G2-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 23H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.73 (s, 1H).

Example 102

2- (6-methyleneoxyG3-benzo [ b ] thiophen-2-yl) pyridine

2- (6-MethyleneoxyG3-benzo [ b ] thiophen-2-yl) pyridine

2- (6-Bromomethyl-benzo [ b ] thiophen-2-yl) pyridine, G3-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.42 (s, 1H), 7.27-7.41 (m , 42H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.57 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.73 (s, 1H).

Example 103

2- (6-methyleneoxyG4-benzo [ b ] thiophen-2-yl) pyridine

2- (6-MethyleneoxyG4-benzo [ b ] thiophen-2-yl) pyridine

2- (6-Bromomethyl-benzo [ b ] thiophen-2-yl) pyridine, G4-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 6]

¹ H-NMR (CDCl ₃ ): δ 8.61 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 83H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.73 (s, 1 H).

Example 104

2- (4-methoxy-naphthalen-1-yl) pyridine

2- (4-Methoxy-naphthalen-1-yl) pyridine

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-naphthalene-1-boronic acid and 2-bromopyridine. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.43 (t, 1H), 7.31 (t, 1H), 6.98 (t, 1H), 6.73 (d, 1H), 3.89 (s, 3H).

Example 105

2- (4-OG1-naphthalene-1-yl) pyridine

2- (4-OG1-naphthalen-1-yl) pyridine

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) pyridine, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.44 (m, 12H), 6.98 (t, 1H), 6.72 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t , 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 106

2- (4-OG2-naphthalene-1-yl) pyridine

2- (4-OG2-naphthalen-1-yl) pyridine

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) pyridine, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.43 (m, 22H), 6.98 (t, 1H), 6.74 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 107

2- (4-OG3-naphthalene-1-yl) pyridine

2- (4-OG3-naphthalen-1-yl) pyridine

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) pyridine, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.43 (m, 42H), 6.98 (t, 1H), 6.70 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

Example 108

2- (4-OG4-naphthalen-1-yl) pyridine

2- (4-OG4-naphthalen-1-yl) pyridine

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) pyridine, G4-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.43 (m, 82H), 6.98 (t, 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 ( s, 32H), 4.95-4.92 (m, 28H).

Example 109

2- (4-methyleneoxyG1-naphthalene-1-yl) pyridine

2- (4-MethyleneoxyG1-naphthalen-1-yl) pyridine

2- (4-Bromomethyl-naphthalen-1-yl) pyridine, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.30-7.49 (m , 13H), 6.98 (t, 1H), 6.71 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 110

2- (4-methyleneoxyG2-naphthalene-1-yl) pyridine

2- (4-MethyleneoxyG2-naphthalen-1-yl) pyridine

2- (4-Bromomethyl-naphthalen-1-yl) pyridine, G2-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.27-7.47 (m, 22H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t , 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 111

2- (4-methyleneoxyG3-naphthalene-1-yl) pyridine

2- (4-MethyleneoxyG3-naphthalen-1-yl) pyridine

2- (4-Bromomethyl-naphthalen-1-yl) pyridine, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

Example 112

2- (4-methyleneoxyG4-naphthalene-1-yl) pyridine

2- (4-MethyleneoxyG4-naphthalen-1-yl) pyridine

2- (4-Bromomethyl-naphthalen-1-yl) pyridine, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 7]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.22 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.43 (m, 82H), 6.62-6.67 (m, 43H, J = 2.1), 6.98 (t, 1H), 6.71 (d, 1H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 113

2- (5-methoxy-naphthalene-1-yl) pyridine

2- (5-Methoxy-naphthalen-1-yl) pyridine

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-naphthalene-1-boronic acid with 2-bromopyridine. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.33 (d, 1H), 7.21 (t, 1H), 6.98 (t, 1H), 6.67 (d, 1H), 3.79 (s, 3H).

Example 114

2- (5-OG1-naphthalen-1-yl) pyridine

2- (5-OG1-naphthalen-1-yl) pyridine

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) pyridine, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (m, 2H), 7.29-7.44 (m , 11H), 7.21 (t, 1H), 6.98 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.67 (d, 1H), 6.57 (t , 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 115

2- (5-OG2-naphthalene-1-yl) pyridine

2- (5-OG2-naphthalen-1-yl) pyridine

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) pyridine, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.29-7.43 (m, 21H), 7.21 (t, 1H), 6.98 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.67 (d , 1H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 116

2- (5-OG3-naphthalen-1-yl) pyridine

2- (5-OG3-naphthalen-1-yl) pyridine

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) pyridine, G3-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.29-7.43 (m, 41H), 7.31 (t, 1H), 6.98 (t, 1H), 6.67 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 117

2- (5-OG4-naphthalen-1-yl) pyridine

2- (5-OG4-naphthalen-1-yl) pyridine

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) pyridine, G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.29-7.43 (m, 81H), 7.21 (t, 1H), 6.98 (t, 1H), 6.67 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 ( s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 118

2- (5-methyleneoxyG1-naphthalene-1-yl) pyridine

2- (5-MethyleneoxyG1-naphthalen-1-yl) pyridine

2- (5-Bromomethyl-naphthalen-1-yl) pyridine, G1-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.30-7.49 (m, 13H), 7.21 (t , 1H), 6.98 (t, 1H), 6.67 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 119

2- (5-methyleneoxyG2-naphthalene-1-yl) pyridine

2- (5-MethyleneoxyG2-naphthalen-1-yl) pyridine

2- (5-Bromomethyl-naphthalen-1-yl) pyridine, G2-OH, was dissolved in acetone and synthesized by adding KOH. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.27-7.47 (m, 21H), 7.21 (t, 1H), 6.98 (t, 1H), 6.68 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 120

2- (5-methyleneoxyG3-naphthalene-1-yl) pyridine

2- (5-MethyleneoxyG3-naphthalen-1-yl) pyridine

2- (5-Bromomethyl-naphthalen-1-yl) pyridine, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.27-7.41 (m, 41H), 7.21 (t, 1H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

Example 121

2- (5-methyleneoxyG4-naphthalene-1-yl) pyridine

2- (5-MethyleneoxyG4-naphthalen-1-yl) pyridine

2- (5-Bromomethyl-naphthalen-1-yl) pyridine, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 8]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 8.21 (d, 1H), 8.13 (d, 1H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H ), 7.29-7.43 (m, 82H), 6.98 (t, 1H), 6.69 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 122

2- (2,3,6-trifluro-4'-methoxybiphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-methoxybiphenyl-4-yl) pyridine

The desired product was synthesized by C-C coupling reaction of 2,3,6-Trifluoro-4'-methoxybiphenyl-4-boronic acid with 2-bromopyridine. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.36 (d, 1H), 6.98 (d, 2H ), 6.83 (d, 2H), 3.87 (s, 3H).

Example 123

2- (2,3,6-trifluro-4'-OG1-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-OG1-biphenyl-4-yl) pyridine

Reaction of 2- (2,3,6-Trifluoro-4'-hydroxybiphenyl-4-yl) pyridine, G1-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.44 (m, 10H), 6.98 (d , 2H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H) , 5.03 (s, 4 H).

Example 124

2- (2,3,6-trifluro-4'-OG2-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-OG2-biphenyl-4-yl) pyridine

Reaction of 2- (2,3,6-Trifluoro-4'-hydroxybiphenyl-4-yl) pyridine, G2-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.43 (m, 21H), 6.98 (d , 2H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 125

2- (2,3,6-trifluro-4'-OG3-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-OG3-biphenyl-4-yl) pyridine

Reaction of 2- (2,3,6-Trifluoro-4'-hydroxybiphenyl-4-yl) pyridine, G3-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.43 (m, 41H), 6.98 (d , 2H), 6.83 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 126

2- (2,3,6-trifluro-4'-OG4-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-OG4-biphenyl-4-yl) pyridine

Reaction of 2- (2,3,6-Trifluoro-4'-hydroxybiphenyl-4-yl) pyridine, G4-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (d , 2H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.04 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 127

2- (2,3,6-trifluro-4'-methyleneoxyG1-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-bromomethylbiphenyl-4-yl) pyridine, G1-OH, was dissolved in acetone and synthesized by adding KOH. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.30-7.49 (m, 12H), 6.98 (d, 2H), 6.83 (d , 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 128

2- (2,3,6-trifluro-4'-methyleneoxyG2-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-bromomethylbiphenyl-4-yl) pyridine, G2-OH, was dissolved in acetone and synthesized by adding KOH. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.27-7.47 (m, 21H), 6.98 (d , 2H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 129

2- (2,3,6-trifluro-4'-methyleneoxyG3-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-bromomethylbiphenyl-4-yl) pyridine, G3-OH, was dissolved in acetone and synthesized by adding KOH. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.27-7.41 (m, 41H), 6.98 (d , 2H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 130

2- (2,3,6-trifluro-4'-methyleneoxyG4-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) pyridine

2- (2,3,6-Trifluoro-4'-bromomethylbiphenyl-4-yl) pyridine, G4-OH, was dissolved in acetone and synthesized by adding KOH. [Legand 9]

¹ H-NMR (CDCl ₃ ): δ 8.58 (d, 1H), 7.55 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (d , 2H), 6.83 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 131

1- (2-methoxy-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-Methoxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

3-methoxyphenylmagnesium solution dissolved in THF was added dropwise at room temperature dropwise to 4- (hydro, fluoro or methyl) isocurolin solution dissolved in diethyl ether, and stirred for 36 hours to obtain the desired species. [Ligand 11]

1- (2-methoxy-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 3.74 (s, 3H), 2.35 (s, 3H).

Example 132

1- (2-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (2-OG1-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.35 (s, 3H).

Example 133

1- (3-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (3-OG1-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.44 (m, 10H), 7.25 (t, 1H), 6.78 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.35 (s, 3H).

Example 134

1- (4-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (4-OG1-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 6.71 (d, 2H, J = 2.1), 6.87 (d, 2H), 6.72 (d, 2H, J = 2.4) , 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

Example 135

1- (2-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (2-OG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.35 (s, 3H ).

Example 136

1- (3-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (3-OG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 20H), 7.25 (t, 1H), 6.78 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.35 (s, 3H ).

Example 137

1- (4-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (4-OG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 6.87 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1) , 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

Example 138

1- (2-OG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (2-OG3-phenyl-4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H), 7.62 ( t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.65-6.52 (m, 21H) , 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.35 (s, 3H).

Example 139

1- (3-OG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (3-OG3-phenyl-4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H), 7.56 ( d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 40H), 7.25 (t, 1H), 6.78 (d, 1H), 6.65-6.52 (m, 21H) , 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.35 (s, 3H).

Example 140

1- (4-OG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (4-OG3-phenyl-4-methyl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 6.87 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H ), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

Example 141

1- (2-OG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-OG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (2-OG4-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.65-6.48 (m, 45H ), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.35 (s, 3H).

Example 142

1- (3-OG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-OG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (3-OG4-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 80H), 7.25 (t, 1H), 6.78 (d, 1H), 6.65-6.48 (m, 45H ), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.35 (s, 3H).

Example 143

1- (4-OG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 It was synthesized through the production reaction. [Ligand 11]

1- (4-OG4-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 6.87 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H ), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.34 (s, 3H).

Example 144

1- (2-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-MethyleneoxyG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (2-methyleneoxyG1-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.55 (t, 1H , J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.35 (s, 3H).

Example 145

1- (3-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-MethyleneoxyG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (3-methyleneoxyG1-phenyl-4-methyl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H) , 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.30-7.49 (m, 11H), 7.25 (t, 1H), 6.78 (d, 1H), 6.55 (t, 1H , J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.35 (s, 3H).

Example 146

1- (4-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG1-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (4-methyleneoxyG1-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 6.87 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H).

Example 147

1- (2-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-MethyleneoxyG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (2-methyleneoxyG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.67 (d, 4H , J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.35 (s, 3H).

Example 148

1- (3-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-MethyleneoxyG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (3-methyleneoxyG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H) , 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.27-7.47 (m, 21H), 7.25 (t, 1H), 6.78 (d, 1H), 6.67 (d, 4H , J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.35 (s, 3H).

Example 149

1- (4-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG2-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (4-methyleneoxyG2-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 6.87 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

Example 150

1- (2-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-MethyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (2-methyleneoxyG3-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.67 (d, 8H , J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s, 3H).

Example 151

1- (3-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-MethyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (3-methyleneoxyG3-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H) , 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.27-7.41 (m, 40H), 7.25 (t, 1H), 6.78 (d, 1H), 6.67 (d, 8H , J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s, 3H).

Example 152

1- (4-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (4-methyleneoxyG3-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 6.87 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 153

1- (2-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2-MethyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (2-methyleneoxyG4-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 1H), 7.82 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.62-6.67 (m , 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s , 3H).

Example 154

1- (3-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3-MethyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (3-methyleneoxyG4-phenyl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 7.89 (d, 2H), 7.62 (t, 1H) , 7.56 (d, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 81H), 7.25 (t, 1H), 6.78 (d, 1H), 6.62-6.67 (m , 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s , 3H).

Example 155

1- (4-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-phenyl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 11]

1- (4-methyleneoxyG4-phenyl) -4-methylisocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 6.87 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 156

1- (2'-methoxy-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-Methoxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

The desired product was synthesized by C-C coupling reaction of 2'-Methoxy-biphenyl-4-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) isocuroline. [Ligand 12]

1- (2'-methoxy-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.38 (d, 1H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 ( d, 1H), 3.74 (s, 3H), 2.32 (s, 3H).

Example 157

1- (2'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2'-hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (2′-OG 1 -biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 11H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

Example 158

1- (3'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (3'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 with hydroxy-aryl and bromo-alkylpyri-

Synthesis was carried out via ether (R'-O-R) production of dine. [Ligand 12]

1- (3'-OG1-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

Example 159

1- (4'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ethers of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (4′-OG 1 -biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 12H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

Example 160

1- (2'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ethers of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (2'-OG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 21H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H) , 4.99 (s, 4H), 2.32 (s, 3H).

Example 161

1- (3'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (3'-OG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H) , 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H).

Example 162

1- (4'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (4'-OG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 22H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H) .

Example 163

1- (2'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ethers of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (2'-OG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 41H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3H).

Example 164

1- (3'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (3'-OG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3 H).

Example 165

1- (4'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (4'-OG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 42H), 6.83 (d, 2H), 6.65-6.52 (m, 21H) , 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3H).

Example 166

1- (2'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (2'-OG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3H ).

Example 167

1- (3'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ether of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (3'-OG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H ), 2.32 (s, 3 H).

Example 168

1- (4'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

Ethers of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4'-Hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 ( R'-OR) was synthesized through the production reaction. [Ligand 12]

1- (4'-OG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 ( d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H) , 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

Example 169

1- (2'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-MethyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (2'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

Example 170

1- (3'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-MethyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (3'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

Example 171

1- (4'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-MethyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (4'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.30-7.49 (m, 12H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

Example 172

1- (2'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-MethyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (2'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

Example 173

1- (3'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-MethyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (3'-MethyloxyG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

Example 174

1- (4'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-MethyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (4'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 22H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

Example 175

1- (2'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-MethyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (2'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 176

1- (3'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-MethyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (3'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 177

1- (4'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-MethyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (4'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.41 (m, 41H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 178

1- (2'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (2'-MethyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (2'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (2'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.05 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 ( s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 179

1- (3'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (3'-MethyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (3'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (3'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.34 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 180

1- (4'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4'-MethyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4'-Bromomethyl-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 12]

1- (4'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.32 (s, 1H), 8.06 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 6.83 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 ( s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 181

1- (5-methoxy-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-Methoxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-thiophen-2-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) -isocurolin. [Ligand 13]

1- (5-methoxy-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 ( t, 1H), 7.51 (t, 1H), 6.66 (d, 1H), 6.01 (d, 1H), 3.80 (s, 3H), 2.33 (s, 3H).

Example 182

1- (5-OG1-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-OG1-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

The reaction of 1- (5-Hydroxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 13]

1- (5-OG1-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t , 1H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 6.72 (d, 2H, J = 2.4), 6.66 (d, 1H), 6.57 (t, 1H, J = 2.4), 6.01 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H), 2.33 (s, 3H).

Example 183

1- (5-OG2-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-OG2-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

The reaction of 1- (5-Hydroxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 13]

1- (5-OG2-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t , 1H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.66 (d, 1H), 6.54 -6.58 (m, 3H), 6.01 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.33 (s, 3H).

Example 184

1- (5-OG3-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-OG3-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (5-Hydroxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 13]

1- (5-OG3-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t , 1H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 20H), 6.66 (d, 1H), 6.01 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.33 (s, 3H).

Example 185

1- (5-OG4-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-OG4-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

The reaction of 1- (5-Hydroxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 13]

1- (5-OG4-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t , 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 6.66 (d, 1H), 6.65-6.48 (m, 45H), 6.01 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.33 (s, 3H).

Example 186

1- (5-methyleneoxyG1-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-MethyleneoxyG1-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (5-CH ₂ Br-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 13]

1- (5-methyleneoxyG1-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.30-7.49 (m, 10H), 6.66 (d, 1H), 6.55 (t, 1H, J = 2.1), 6.01 (d, 1H), 5.02 (s , 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.33 (s, 3H).

Example 187

1- (5-methyleneoxyG2-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-MethyleneoxyG2-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (5-CH ₂ Br-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 13]

1- (5-methyleneoxyG2-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 20H), 6.67 (m, 5H), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 6.01 (d, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.33 (s , 3H).

Example 188

1- (5-methyleneoxyG3-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-MethyleneoxyG3-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (5-CH ₂ Br-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 13]

1- (5-methyleneoxyG3-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 6.67 (d, 8H, J = 2.1), 6.66 (d, 1H), 6.64 (d, 4H, J = 2.4) , 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.01 (d, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H) , 4.52 (d, 2H), 2.33 (s, 3H).

Example 189

1- (5-methyleneoxyG4-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-MethyleneoxyG4-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (5-CH ₂ Br-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 13]

1- (5-methyleneoxyG4-thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 7.02 (d, 2H), 6.62-6.67 (m, 44H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.01 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3H).

Example 190

1- [5- (2-methoxy-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-Methoxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline

The desired product was synthesized by C-C coupling reaction of 5- (2-Methoxy-phenyl) -thiophen-2-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) isocurolin. [Ligand 14]

1- [5- (2-methoxy-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 (d , 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 3.82 (s, 3H), 2.34 (s, 3H).

Example 191

1- [5- (2-OG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-OG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G1-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (2-OG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 (d, 2H), 7.77 (t, 1H), 7.55 (t, 1H), 7.29-7.44 (m, 11H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H) , 2.34 (s, 3 H).

Example 192

1- [5- (3-OG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) isocurolin

1- [5- (3-OG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G1-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (3-OG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.44 (m, 10H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d , 1H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H) , 5.03 (s, 4H), 2.34 (s, 3H).

Example 193

1- [5- (4-OG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-OG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G1-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (4-OG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.44 (m, 12H), 7.05 (d, 2H), 6.89 (d, 2H), 6.71 (d, 2H, J = 2.1) 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

Example 194

1- [5- (2-OG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-OG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G2-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (2-OG2-phenyl) -thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 (d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 20H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t , 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

Example 195

1- [5- (3-OG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-OG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G2-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (3-OG2-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 20H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d , 1H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

Example 196

1- [5- (4-OG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) isocurolin

1- [5- (4-OG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G2-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (4-OG2-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 22H), 7.05 (d, 2H), 6.89 (d, 2H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

Example 197

1- [5- (2-OG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-OG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G3-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (2-OG3-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 (d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 40H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t , 1H), 6.83 (d, 1H), 7.25 (t, 1H), 7.02 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

Example 198

1- [5- (3-OG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-OG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G3-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (3-OG3-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 40H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d , 1H), 6.75 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 ( s, 3H).

Example 199

1- [5- (4-OG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-OG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G3-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (4-OG3-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 42H), 7.05 (d, 2H), 6.89 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

Example 200

1- [5- (2-OG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-OG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G4-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (2-OG4-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 (d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 80H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t , 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.34 (s, 3 H).

Example 201

1- [5- (3-OG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-OG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G4-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (3-OG4-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 80H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d , 1H), 6.75 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.34 (s, 3 H).

Example 202

1- [5- (4-OG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-OG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G4-Br and 18-crown-6 reacted with hydroxy-aryl It was synthesized by ether (R'-OR) production of bromo-alkylpyridine. [Ligand 14]

1- [5- (4-OG4-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 (d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (d, 2H), 6.89 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.34 (s, 3H).

Example 203

1- [5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 ( d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.30-7.49 (m, 10H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H ).

Example 204

1- [5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-MethyleneoxyG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.30-7.49 (m, 10H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d, 1H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H ).

Example 205

1- [5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.30-7.49 (m, 12H), 7.05 (d, 2H), 6.89 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H).

Example 206

1- [5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 ( d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.27-7.47 (m, 21H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

Example 207

1- [5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-MethyleneoxyG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl] -4-methyl-isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.27-7.47 (m, 20H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d, 1H), 6.75 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

Example 208

1- [5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-MethyleneoxyG2-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (4-MethyleneoxyG2-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.27-7.47 (m, 22H), 7.05 (d, 2H), 6.89 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2 H), 4.52 (s, 2 H), 2.34 (s, 3 H).

Example 209

1- [5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 ( d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.27-7.41 (m, 40H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 210

1- [5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-MethyleneoxyG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.27-7.41 (m, 40H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d, 1H), 6.75 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 211

1- [5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -4-methyl-isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.81 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.27-7.41 (m, 43H), 7.05 (d, 2H), 6.89 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2 H), 4.52 (d, 2 H), 2.34 (s, 3 H).

Example 212

1- [5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (2-MethyleneoxyG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (2-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.82 ( d, 2H), 7.77 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 80H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H) , 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 213

1- [5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (3-MethyleneoxyG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (3-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl] -4-methyl-isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.35 (s, 1H), 7.82 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 81H), 7.24 (t, 1H), 7.07 (t, 1H), 7.05 (d, 2H), 6.99 (d, 1H), 6.75 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H) , 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

Example 214

1- [5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [5- (4-MethyleneoxyG4-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

1- [5- (4-BrCH ₂ -phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 14]

1- [5- (4-MethyleneoxyG4-phenyl) -thiophen-2-yl] -4-methyl-isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.36 (s, 1H), 7.81 ( d, 2H), 7.76 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (d, 2H), 6.89 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H) .

Example 215

1- [7- (2-methoxy-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

The desired product was synthesized by CC coupling reaction of 7- (2-Methoxy-phenyl) -9 H- fluorene-2-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) isocurolin. [Ligand 15]

1- [7- (2-methoxy-phenyl) -9 H- floren-2-yl] -4-methyl-isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.37 (d, 1H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 3.88 (d, 2H), 3.73 (s, 3H), 2.32 ( s, 3H).

Example 216

1- [7- (2-OG1-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-OG1-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Hydroxy-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline, G1-Br and 18-crown-6 in the reaction of hydroxy- It was synthesized by ether (R'-OR) formation reaction of aryl and bromo-alkylpyridine. [Ligand 15]

1- [7- (2-OG1-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 ( t, 1H), 7.29-7.44 (m, 11H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 217

1- [7- (2-OG2-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-OG2-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ ) -iso quinoline

1- [7- (2-Hydroxy-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G2-Br and 18-crown-6 It was synthesized by ether (R'-OR) production of -aryl and bromo-alkylpyridine. [Ligand 15]

1- [7- (2-OG2-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 ( t, 1H), 7.29-7.43 (m, 21H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H) .

Example 218

1- [7- (2-OG3-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-OG3-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ ) -iso quinoline

1- [7- (2-Hydroxy-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ ) -iso quinoline, G3-Br and 18-crown-6 It was synthesized by ether (R'-OR) production of -aryl and bromo-alkylpyridine. [Ligand 15]

1- [7- (2-OG3-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 ( t, 1H), 7.29-7.43 (m, 41H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H) , 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 219

1- [7- (2-OG4-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-OG4-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Hydroxy-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline, G4-Br and 18-crown-6 in the reaction of hydroxy- It was synthesized by ether (R'-OR) formation reaction of aryl and bromo-alkylpyridine. [Ligand 15]

1- [7- (2-OG4-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 ( t, 1H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H) , 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 220

1- [7- (2-methyleneoxyG1-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-MethyleneoxyG1-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 15]

1- [7- (2-methyleneoxyG1-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H) , 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.30-7.49 (m, 11H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 ( s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 221

1- [7- (2-methyleneoxyG2-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-MethyleneoxyG2-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 15]

1- [7- (2-methyleneoxyG2-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H) , 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.27-7.47 (m, 21H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 ( d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H ), 4.52 (s, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 222

1- [7- (2-methyleneoxyG3-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-MethyleneoxyG3-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 15]

1- [7- (2-methyleneoxyG3-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H) , 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.27-7.41 (m, 41H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 ( d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H ), 4.52 (d, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 223

1- [7- (2-methyleneoxyG4-phenyl) -9 H -floren-2-yl] -4- (hydro, fluoro or methyl) -isocurolin

1- [7- (2-MethyleneoxyG4-phenyl) -9 H -fluoren-2-yl] -4- (H, F or CH ₃ )-isoquinoline

1- [7- (2-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 15]

1- [7- (2-methyleneoxyG4-phenyl) -9 H -floren-2-yl] -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H) , 8.27 (s, 1H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

Example 224

1- (6-methoxy-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-Methoxy-benzo [b] thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinoline

The desired product was synthesized by C-C coupling reaction of 6-Methoxy-benzo [b] thiophen-2-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) isocurolin. [Ligand 16]

1- (6-methoxy-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H ), 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.43 (s, 1H), 7.33 (s, 1H), 6.82 (d, 1H), 3.79 (s, 3H) , 2.32 (s, 3 H).

Example 225

1- (6-OG1-Benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-OG1-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

Hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline with G1-Br and 18-crown-6 It was synthesized through the ether (R'-OR) formation reaction. [Ligand 16]

1- (6-OG1-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H) , 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.44 (m, 12H), 6.82 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

Example 226

1- (6-OG2-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-OG2-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

Hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline with G2-Br and 18-crown-6 It was synthesized through the ether (R'-OR) formation reaction. [Ligand 16]

1- (6-OG2-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H) , 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 22H), 6.82 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H).

Example 227

1- (6-OG3-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-OG3-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

Hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline with G3-Br and 18-crown-6 It was synthesized through the ether (R'-OR) formation reaction. [Ligand 16]

1- (6-OG3-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H) , 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 42H), 6.82 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s , 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3H).

Example 228

1- (6-OG4-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-OG4-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

Hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline with G4-Br and 18-crown-6 It was synthesized through the ether (R'-OR) formation reaction. [Ligand 16]

1- (6-OG4-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H) , 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 6.82 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s , 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

Example 229

1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-MethyleneoxyG1-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (6-BrCH ₂ -benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 16]

1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H), 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.30-7.49 (m, 12H), 6.82 (d, 1H), 6.55 (t, 1H, J = 2.1) , 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

Example 230

1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (6-MethyleneoxyG2-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (6-BrCH ₂ -benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 16]

1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H), 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.27-7.47 (m, 22H), 6.82 (d, 1H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 ( s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

Example 231

1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) isocurolin

1- (6-MethyleneoxyG3-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (6-BrCH ₂ -benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 16]

1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H), 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.43 (s, 1H), 7.27-7.41 (m, 41H), 6.82 (d, 1H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 232

1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) isocurolin

1- (6-MethyleneoxyG4-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (6-BrCH ₂ -benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 16]

1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -4-methyl) isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.31 (s, 1H), 7.88 (d, 2H), 7.78 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 6.82 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 233

1- (4-methoxy-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-Methoxy-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-naphthalene-1-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) isocurolin. [Ligand 17]

1- (4-methoxy-naphthalene-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d , 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.42 (t, 1H), 7.32 (t, 1H), 6.75 (d, 1H), 3.73 (s, 3H), 2.32 (s, 3H).

Example 234

1- (4-OG1-naphthalen-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG1-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (4-Hydroxy-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline with G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 17]

1- (4-OG 1 -naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.29-7.44 (m, 12H), 6.75 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H) .

Example 235

1- (4-OG2-naphthalen-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG2-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (4-Hydroxy-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline with G2-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 17]

1- (4-OG2-naphthalene-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.29-7.43 (m, 22H), 6.75 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3 H).

Example 236

1- (4-OG3-naphthalen-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG3-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (4-Hydroxy-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline with G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 17]

1- (4-OG3-naphthalene-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.29-7.43 (m, 40H), 6.75 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3H).

Example 237

1- (4-OG4-naphthalen-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-OG4-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (4-Hydroxy-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline with G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Ligand 17]

1- (4-OG4-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.29-7.43 (m, 82H), 6.75 (d, 1H), 6.65-6.48 (m, 45H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

Example 238

1- (4-methyleneoxyG1-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG1-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 17]

1- (4-methyleneoxyG1-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H) , 7.42 (t, 1H), 7.30-7.49 (m, 11H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

Example 239

1- (4-methyleneoxyG2-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG2-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 17]

1- (4-methyleneoxyG2-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H) , 7.27-7.47 (m, 22H), 6.75 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

Example 240

1- (4-methyleneoxyG3-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (4-MethyleneoxyG3-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (4-Bromomethyl-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 17]

1- (4-methyleneoxyG3-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H) , 7.27-7.41 (m, 42H), 6.75 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 241

1- (4-methyleneoxyG4-naphthalene-1-yl) -4-methyl-isocurolin

1- (4-MethyleneoxyG4-naphthalen-1-yl) -4-methyl-isoquinoline

1- (4-Bromomethyl-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 17]

1- (4-methyleneoxyG4-naphthalene-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H) , 7.29-7.43 (m, 82H), 6.75 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 ( s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

Example 242

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-methoxy-biphenyl-4-yl)

-iso quinoline

The desired product was synthesized by CC coupling reaction of 2,3,6-Trifluoro-4'-methoxy-biphenyl-4-boronic acid with 1-bromo-4- (hydro, fluoro or methyl) -isocurolin. . [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H ), 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.38 (d, 2H), 7.05 (s, 1H), 6.88 (d, 2H), 3.76 (s, 3H) , 2.33 (s, 3 H).

Example 243

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-OG1-biphenyl-4-yl) -iso quinoline

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl)-

The reaction of 4- (H, F or CH ₃ ) -isoquinoline, G1-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H) , 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.38 (d, 2H), 7.05 (s, 1H), 6.88 (d, 2H), 7.29-7.44 (m, 10H ), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.33 (s, 3 H).

Example 244

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-OG2-biphenyl-4-yl) -iso quinoline

Hydroxy by reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -iso quinoline, G2-Br and 18-crown-6 It was synthesized by ether (R'-OR) production of -aryl and bromo-alkylpyridine. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H) , 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 22H), 7.05 (s, 1H), 6.88 (d, 2H), 6.71 (d, 2H , J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.33 (s , 3H).

Example 245

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-OG3-biphenyl-4-yl)-

isoquinoline

1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ )-

The reactions of isoquinoline, G3-Br and 18-crown-6 were synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H) , 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 42H), 7.05 (s, 1H), 6.88 (d, 2H), 6.65-6.52 (m , 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.33 (s, 3H).

Example 246

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-OG4-biphenyl-4-yl) -iso quinoline

Hydroxy by reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -iso quinoline, G4-Br and 18-crown-6 It was synthesized by ether (R'-OR) production of -aryl and bromo-alkylpyridine. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H) , 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (s, 1H), 6.88 (d, 2H), 6.65-6.48 (m , 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.33 (s, 3H).

Example 247

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -isoquinoline

Dissolve 1- (2,3,6-Trifluoro-4'-CH ₂ Br-biphenyl-4-yl) -4- (H, F or CH ₃ ) -iso quinoline and G1-OH in acetone and add KOH Synthesized. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.30-7.49 (m, 12H), 7.05 (s, 1H), 6.88 (d, 2H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.33 (s, 3H).

Example 248

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -isoquinoline

Synthesized by dissolving 1- (2,3,6-Trifluoro-4'-CH ₂ Br-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline and G2-OH in acetone and adding KOH It was. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -isocuroline: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.27-7.47 (m, 22H), 7.05 (s, 1H), 6.88 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.33 (s, 3H).

Example 249

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl] -isoquinoline

Synthesized by dissolving 1- (2,3,6-Trifluoro-4'-CH ₂ Br-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline and G3-OH in acetone and adding KOH It was. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.27-7.41 (m, 42H), 7.05 (s, 1H), 6.88 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3H).

Example 250

4- (hydro, fluoro or methyl) -1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -isocurolin

4- (H, F or CH ₃ ) -1- (2,3,6-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -isoquinoline

Synthesized by dissolving 1- (2,3,6-Trifluoro-4'-CH ₂ Br-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline and G4-OH in acetone and adding KOH It was. [Ligand 19]

4-Methyl-1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.34 (s, 1H), 7.83 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (s, 1H), 6.88 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3 H).

Example 251

6- (4-methoxy-phenyl) -phenanthridine

6- (4-Methoxy-phenyl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-benzene-1-boronic acid with 6-bromo-phenanthridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.88 (d, 2H), 7.45 (t, 1H), 6.86 (d, 2H), 3.75 (s, 3H).

Example 252

6- (2-OG1-phenyl) -phenanthtridine

6- (2-OG1-phenyl) -phenanthridine

The reaction of 6- (2-Hydroxy-phenyl) -phenanthridine with G1-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (d, 2H), 7.85 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.29-7.44 (m, 11H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 253

6- (3-OG1-phenyl) -phenanthridine

6- (3-OG1-phenyl) -phenanthridine

The reaction of 6- (3-Hydroxy-phenyl) -phenanthridine with G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.29-7.44 (m, 11H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 254

6- (4-OG1-phenyl) -phenanthtridine

6- (4-OG1-phenyl) -phenanthridine

The reaction of 6- (4-Hydroxy-phenyl) -phenanthridine with G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 18]

1 H-NMR (CDCl 3): δ 8.10 (d, 1H), 7.88 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.44 (m, 10H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H ), 5.03 (s, 4 H).

Example 255

6- (2-OG2-phenyl) -phenanthridine

6- (2-OG2-phenyl) -phenanthridine

The reaction of 6- (2-Hydroxy-phenyl) -phenanthridine with G2-Br and 18-crown-6 was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.89 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 20H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 256

6- (3-OG2-phenyl) -phenanthridine

6- (3-OG2-phenyl) -phenanthridine

The reaction of 6- (3-Hydroxy-phenyl) -phenanthridine with G2-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 20H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 257

6- (4-OG2-phenyl) -phenanthridine

6- (4-OG2-phenyl) -phenanthridine

The reaction of 6- (4-Hydroxy-phenyl) -phenanthridine with G2-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.88 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 20H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 258

6- (2-OG3-phenyl) -phenanthridine

6- (2-OG3-phenyl) -phenanthridine

The reaction of 6- (2-Hydroxy-phenyl) -phenanthridine with G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.89 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 40H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.65-6.52 ( m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 259

6- (3-OG3-phenyl) -phenanthridine

6- (3-OG3-phenyl) -phenanthridine

The reaction of 6- (3-Hydroxy-phenyl) -phenanthridine with G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 40H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.65-6.52 ( m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 260

6- (4-OG3-phenyl) -phenanthridine

6- (4-OG3-phenyl) -phenanthridine

The reaction of 6- (4-Hydroxy-phenyl) -phenanthridine with G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.89 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 40H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

Example 261

6- (2-OG4-phenyl) -phenanthridine

6- (2-OG4-phenyl) -phenanthridine

The reaction of 6- (2-Hydroxy-phenyl) -phenanthridine with G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 80H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 262

6- (3-OG4-phenyl) -phenanthridine

6- (3-OG4-phenyl) -phenanthridine

The reaction of 6- (3-Hydroxy-phenyl) -phenanthridine with G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 80H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 263

6- (4-OG4-phenyl) -phenanthridine

6- (4-OG4-phenyl) -phenanthridine

The reaction of 6- (4-Hydroxy-phenyl) -phenanthridine with G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.89 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 80H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 ( s, 32H), 4.95-4.92 (m, 28H).

Example 264

6- (2-methyleneoxyG1-phenyl) -phenanthtridine

6- (2-MethyleneoxyG1-phenyl) -phenanthridine

6- (2-CH ₂ Br-phenyl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.30-7.49 (m, 11H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 265

6- (3-methyleneoxyG1-phenyl) -phenanthtridine

6- (3-MethyleneoxyG1-phenyl) -phenanthridine

6- (3-CH ₂ Br-phenyl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.30-7.49 (m, 11H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 266

6- (4-methyleneoxyG1-phenyl) -phenanthridine

6- (4-MethyleneoxyG1-phenyl) -phenanthridine

6- (4-CH ₂ Br-phenyl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.88 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.30-7.49 (m, 11H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 267

6- (2-methyleneoxyG2-phenyl) -phenanthtridine

6- (2-MethyleneoxyG2-phenyl) -phenanthridine

6- (2-CH ₂ Br-phenyl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.27-7.47 (m, 21H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 268

6- (3-methyleneoxyG2-phenyl) -phenanthtridine

6- (3-MethyleneoxyG2-phenyl) -phenanthridine

6- (3-CH ₂ Br-phenyl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.27-7.47 (m, 22H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 269

6- (4-methyleneoxyG2-phenyl) -phenanthtridine

6- (4-MethyleneoxyG2-phenyl) -phenanthridine

6- (2-CH ₂ Br-phenyl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.87 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.27-7.47 (m, 20H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t , 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 270

6- (2-methyleneoxyG3-phenyl) -phenanthtridine

6- (2-MethyleneoxyG3-phenyl) -phenanthridine

6- (2-CH ₂ Br-phenyl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (m, 3H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.27-7.41 (m, 40H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

Example 271

6- (3-methyleneoxyG3-phenyl) -phenanthtridine

6- (3-MethyleneoxyG3-phenyl) -phenanthridine

6- (3-CH ₂ Br-phenyl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.27-7.41 (m, 41H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

Example 272

6- (4-methyleneoxyG3-phenyl) -phenanthtridine

6- (4-MethyleneoxyG3-phenyl) -phenanthridine

6- (4-CH ₂ Br-phenyl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.88 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.27-7.41 (m, 40H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

Example 273

6- (2-methyleneoxyG4-phenyl) -phenanthtridine

6- (2-MethyleneoxyG4-phenyl) -phenanthridine

6- (2-CH ₂ Br-phenyl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 81H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.62-6.67 ( m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 274

6- (3-methyleneoxyG4-phenyl) -phenanthtridine

6- (3-MethyleneoxyG4-phenyl) -phenanthridine

6- (3-CH ₂ Br-phenyl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 80H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.62-6.67 ( m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 275

6- (4-methyleneoxyG4-phenyl) -phenanthtridine

6- (4-MethyleneoxyG4-phenyl) -phenanthridine

6- (4-CH ₂ Br-phenyl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 21]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 7.88 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 81H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H , J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 276

6- (2 ', 3' or 4'-methoxy-biphenyl-4-yl) -phenanthtridyne

6- (2 ', 3' or 4'-Methoxy-biphenyl-4-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 2 ', 3', 4 'or 5'-Methoxy-biphenyl-4-boronic acid with 6-bromo-phenanthtridine. [Ligand 22]

6- (4'-methoxy-biphenyl-4-yl) -phenanthtridyne: ¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.37 (d, 2H) ), 6.83 (d, 2H), 3.82 (s, 3H).

Example 277

6- (2'-OG1-biphenyl-4-yl) -phenanthtridiin

6- (2'-OG1-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2'-Hydroxy-biphenyl-4-yl) -phenanthridine, G1-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

6- (2'-OG1-biphenyl-4-yl) -phenanthtridyne: ¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H ), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

Example 278

6- (3'-OG1-biphenyl-4-yl) -phenanthtridiin

6- (3'-OG1-biphenyl-4-yl) -phenanthridine

6- (3'-Hydroxy-biphenyl-4-yl) -phenanthridine, G1-Br and 18-crown-6, were synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.30-7.49 (m, 11H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

Example 279

6- (4'-OG1-biphenyl-4-yl) -phenanthtridiin

6- (4'-OG1-biphenyl-4-yl) -phenanthridine

The reaction of 6- (4'-Hydroxy-biphenyl-4-yl) -phenanthridine, G1-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

Example 280

6- (2'-OG2-biphenyl-4-yl) -phenanthtridyne

6- (2'-OG2-biphenyl-4-yl) -phenanthridine

6- (2'-Hydroxy-biphenyl-4-yl) -phenanthridine, G2-Br and 18-crown-6 were synthesized through the reaction of hydroxy-aryl and bromo-alkylpyridine (R'-OR) formation. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 22H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 281

6- (3'-OG2-biphenyl-4-yl) -phenanthtridyne

6- (3'-OG2-biphenyl-4-yl) -phenanthridine

The reaction of 6- (3'-Hydroxy-biphenyl-4-yl) -phenanthridine, G2-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 22H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (m, 3H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 282

6- (4'-OG2-biphenyl-4-yl) -phenanthtridyne

6- (4'-OG2-biphenyl-4-yl) -phenanthridine

The reaction of 6- (4'-Hydroxy-biphenyl-4-yl) -phenanthridine, G2-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J) = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 283

6- (2'-OG3-biphenyl-4-yl) -phenanthtridyne

6- (2'-OG3-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2'-Hydroxy-biphenyl-4-yl) -phenanthridine, G3-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 42H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65-6.52 ( m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 284

6- (3'-OG3-biphenyl-4-yl) -phenanthtridyne

6- (3'-OG3-biphenyl-4-yl) -phenanthridine

The reaction of 6- (3'-Hydroxy-biphenyl-4-yl) -phenanthridine, G3-Br and 18-crown-6 was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 42H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 285

6- (4'-OG3-biphenyl-4-yl) -phenanthtridyne

6- (4'-OG3-biphenyl-4-yl) -phenanthridine

The reaction of 6- (4'-Hydroxy-biphenyl-4-yl) -phenanthridine, G3-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 43H), 6.83 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 286

6- (2'-OG4-biphenyl-4-yl) -phenanthtridyne

6- (2'-OG4-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2'-Hydroxy-biphenyl-4-yl) -phenanthridine, G4-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 82H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 287

6- (3'-OG4-biphenyl-4-yl) -phenanthtridyne

6- (3'-OG4-biphenyl-4-yl) -phenanthridine

6- (3'-Hydroxy-biphenyl-4-yl) -phenanthridine, G4-Br and 18-crown-6 were synthesized through the reaction of ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 82H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 289

6- (4'-OG4-biphenyl-4-yl) -phenanthtridyne

6- (4'-OG4-biphenyl-4-yl) -phenanthridine

The reaction of 6- (4'-Hydroxy-biphenyl-4-yl) -phenanthridine, G4-Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. . [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 ( s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 290

6- (2'-methyleneoxyG1-biphenyl-4-yl) -phenanthtridyne

6- (2'-MethyleneoxyG1-biphenyl-4-yl) -phenanthridine

6- (2'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.05 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 291

6- (3'-methyleneoxyG1-biphenyl-4-yl) -phenanthridine

6- (3'-MethyleneoxyG1-biphenyl-4-yl) -phenanthridine

6- (3'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 292

6- (4'-methyleneoxyG1-biphenyl-4-yl) -phenanthtridyne

6- (4'-MethyleneoxyG1-biphenyl-4-yl) -phenanthridine

6- (4'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 293

6- (2'-methyleneoxyG2-biphenyl-4-yl) -phenanthridine

6- (2'-MethyleneoxyG2-biphenyl-4-yl) -phenanthridine

6- (2'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.27-7.47 (m, 22H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 294

6- (3'-methyleneoxyG2-biphenyl-4-yl) -phenanthtridyne

6- (3'-MethyleneoxyG2-biphenyl-4-yl) -phenanthridine

6- (3'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.27-7.47 (m, 22H), 7.17 (t, 1H), 7.06 (d, 1H), 7.02 (d, 2H), 6.98 (s, 1H), 6.71 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 295

6- (4'-methyleneoxyG2-biphenyl-4-yl) -phenanthtridyne

6- (4'-MethyleneoxyG2-biphenyl-4-yl) -phenanthridine

6- (4'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.47 (m, 22H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s , 2H), 4.52 (s, 2H).

Example 296

6- (2'-methyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (2'-MethyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (2'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s , 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 297

6- (3'-methyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (3'-MethyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (3'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 298

6- (4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (4'-MethyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (4'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 42H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

Example 299

6- (2'-methyleneoxyG4-biphenyl-4-yl) -phenanthtridyne

6- (2'-MethyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (2'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.62-6.67 ( m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 300

6- (3'-methyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (3'-MethyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (3'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.29-7.43 (m, 81H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 ( s, 2H), 4.52 (d, 2H).

Example 301

6- (4'-methyleneoxyG4-biphenyl-4-yl) -phenanthtridyne

6- (4'-MethyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (4'-Bromomethyl-biphenyl-4-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 22]

¹ H-NMR (CDCl ₃ ): δ 8.05 (d, 2H), 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H ), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.29-7.43 (m, 83H), 6.83 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 302

6- (5-methoxy-thiophen-2-yl) -phenanthtridyne

6- (5-Methoxy-thiophen-2-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-thiophen-2-boronic acid with 6-bromo-phenanthridine. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.43 (t, 1H), 6.53 (d, 1H), 6.03 (d, 1H), 3.85 (s, 3H).

Example 303

6- (5-OG1-thiophen-2-yl) -phenanthtridyne

6- (5-OG1-thiophen-2-yl) -phenanthridine

The reaction of 6- (5-Hydroxy-thiophen-2-yl) -phenanthridine with G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.30-7.49 (m, 11H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.53 (d, 1H), 6.03 (d , 1H), 5.02 (s, 4H), 4.62 (s, 2H).

Example 304

6- (5-OG2-thiophen-2-yl) -phenanthtridyne

6- (5-OG2-thiophen-2-yl) -phenanthridine

The reaction of 6- (5-Hydroxy-thiophen-2-yl) -phenanthridine with G2-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 21H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.53 (d, 1H), 6.05 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 305

6- (5-OG3-thiophen-2-yl) -phenanthtridyne

6- (5-OG3-thiophen-2-yl) -phenanthridine

The reaction of 6- (5-Hydroxy-thiophen-2-yl) -phenanthridine with G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 18]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 41H), 6.65-6.52 (m, 21H), 6.03 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

Example 306

6- (5-OG4-thiophen-2-yl) -phenanthtridyne

6- (5-OG4-thiophen-2-yl) -phenanthridine

The reaction of 6- (5-Hydroxy-thiophen-2-yl) -phenanthridine with G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 81H), 6.65-6.48 (m, 45H), 6.53 (d, 1H), 6.11 (d, 1H), 5.09 (s, 2H), 5.01 ( s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 307

6- (5-methyleneoxyG1-thiophen-2-yl) -phenanthtridyne

6- (5-MethyleneoxyG1-thiophen-2-yl) -phenanthridine

6- (5-Bromomethyl-thiophen-2-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.43 (t, 1H), 7.30-7.49 (m, 11H), 6.55 (t, 1H, J = 2.1), 6.53 (d, 1H), 6.03 (d, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 308

6- (5-methyleneoxyG2-thiophen-2-yl) -phenanthtridyne

6- (5-MethyleneoxyG2-thiophen-2-yl) -phenanthridine

6- (5-Bromomethyl-thiophen-2-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.27-7.47 (m, 22H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (m, 2H), 6.01 (d, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 309

6- (5-methyleneoxyG3-thiophen-2-yl) -phenanthtridyne

6- (5-MethyleneoxyG3-thiophen-2-yl) -phenanthridine

6- (5-Bromomethyl-thiophen-2-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t , 4H, J = 2.4), 6.53 (m, 3H), 6.07 (d, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 310

6- (5-methyleneoxyG4-thiophen-2-yl) -phenanthtridyne

6- (5-MethyleneoxyG4-thiophen-2-yl) -phenanthridine

6- (5-Bromomethyl-thiophen-2-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 23]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 81H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.53 (d, 1H), 6.0 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 311

6- [5- (2, 3, or 4-methoxy-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2, 3 or 4-Methoxy-phenyl) -thiophen-2-yl] -phenanthridine

The desired product was synthesized by C-C coupling reaction of 5- (2, 3 or 4-Methoxy-phenyl) -thiophen-2-boronic acid with 6-bromo-phenanthtridine. [Ligand 24]

6- [5- (4-methoxy-phenyl) -thiophen-2-yl] -phenanthtridyne: ¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H) , 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.44 (t, 1H), 7.37 (d, 2H), 7.03 (d, 2H), 6.86 (d, 2H), 3.73 (s, 3H).

Example 312

6- [5- (2-OG1-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2-OG1-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G1-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.29-7.44 (m, 12H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 313

6- [5- (3-OG1-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (3-OG1-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G1-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.44 (m, 11H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.72 ( d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 314

6- [5- (4-OG1-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-OG1-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G1-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.44 (m, 13H), 7.20-7.23 (m, 1H), 7.03 (d, 2H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4 ), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 315

6- [5- (2-OG2-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2-OG2-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G2-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.29-7.43 (m, 22H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J) = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 316

6- [5- (3-OG2-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (3-OG2-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G2-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 21H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.71 ( d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 317

6- [5- (4-OG2-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-OG2-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G2-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 7.03 (d, 2H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J) = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 318

6- [5- (2-OG3-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2-OG3-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G3-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.29-7.43 (m, 42H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 319

6- [5- (3-OG3-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (3-OG3-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G3-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 41H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.65- 6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 320

6- [5- (4-OG3-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-OG3-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G3-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 43H), 7.03 (d, 2H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 321

6- [5- (2-OG4-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (2-OG4-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G4-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 ( s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 322

6- [5- (3-OG4-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (3-OG4-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G4-Br and 18-crown-6 to generate ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR) Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 81H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.65- 6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 323

6- [5- (4-OG4-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (4-OG4-phenyl) -thiophen-2-yl] -phenanthridine

Reaction of 6- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -phenanthridine with G4-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 7.03 (d, 2H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 ( s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 324

6- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.30-7.49 (m, 13H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 325

6- [5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (3-MethyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.30-7.49 (m, 13H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 326

6- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.30-7.49 (m, 14H), 7.03 (d, 2H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 327

6- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (m, 2H ), 7.27-7.47 (m, 23H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 328

6- [5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (3-MethyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.57 (t, 1H), 7.67 (t, 1H ), 7.50 (t, 1H), 7.27-7.47 (m, 22H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.67 ( d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 329

6- [5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-MethyleneoxyG2-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.27-7.47 (m, 24H), 7.03 (d, 2H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 330

6- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H ), 7.57 (t, 1H), 7.44 (t, 1H), 7.27-7.41 (m, 42H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 331

6- [5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (3-MethyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.44 (t, 1H), 7.27-7.41 (m, 41H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 ( d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 332

6- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.44 (t, 1H), 7.27-7.41 (m, 43H), 7.03 (d, 2H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

Example 333

6- [5- (2-MethyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (2-MethyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H ), 7.59 (t, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.62-6.67 ( m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 334

6- [5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthtridyne

6- [5- (3-MethyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 81H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 ( d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2 H).

Example 335

6- [5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthtridiin

6- [5- (4-MethyleneoxyG4-phenyl) -thiophen-2-yl] -phenanthridine

6- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 24]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 7.03 (d, 2H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 336

6- [7- (4-methoxy-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-Methoxy-phenyl) -9 H -fluoren-2-yl] -phenanthridine

The desired product was synthesized by CC coupling reaction of 7- (4-Methoxy-phenyl) -9 H- fluoren-2-boronic acid with 6-bromo-phenanthtridine. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (m, 2H), 7.73 (d, 1H), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H) , 7.44 (t, 1H), 7.37 (d, 2H), 6.86 (d, 2H), 3.87 (d, 2H), 3.73 (s, 3H).

Example 337

6- [7- (4-OG1-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-OG1-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] -phenanthridine, G1-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'- of OR) through synthesis reaction. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (m, 2H), 7.73 (d, 1H), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H) , 7.29-7.44 (m, 13H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.86 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.87 (d, 2H).

Example 338

6- [7- (4-OG2-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-OG2-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] -phenanthridine, G2-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'- of OR) through synthesis reaction. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.13 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H ), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.87 ( d, 2H).

Example 339

6- [7- (4-OG3-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-OG3-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] -phenanthridine, G3-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'- of OR) through synthesis reaction. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.73 (m, 3H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 43H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.87 (d, 2H).

Example 340

6- [7- (4-OG4-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-OG4-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Hydroxy- phenyl) -9 H -fluoren-2-yl] -phenanthridine, G4-Br and 18-crown-6 by reaction with hydroxy-aryl ether of bromo-alkylpyridine (R'- of OR) through synthesis reaction. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (s, 1H), 7.73 (m, 3H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.87 (d, 2H).

Example 341

6- [7- (4-methyleneoxyG1-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-MethyleneoxyG1-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (s, 1H), 7.73 (m, 3H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.30-7.49 (m, 14H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.87 (d, 2H).

Example 342

6- [7- (4-methyleneoxyG2-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-MethyleneoxyG2-phenyl) -9 H -fluoren-2-yl] -phenanthridine

Dissolve 6- [7- (4-Bromomethyl- phenyl) -9 H -fluoren-2-yl] -phenanthridine and G2-OH were prepared in acetone by addition of KOH. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (s, 1H), 7.73 (m, 3H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.27-7.47 (m, 24H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.87 (d, 2H).

Example 343

6- [7- (4-methyleneoxyG3-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-MethyleneoxyG3-phenyl) -9 H -fluoren-2-yl] -phenanthridine

6- [7- (4-Bromomethyl-phenyl) -9 H- fluoren-2-yl] -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (m 2), 7.73 (d, 1H), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.27-7.41 (m, 44H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (d, 2H).

Example 344

6- [7- (4-methyleneoxyG4-phenyl) -9 H -floren-2-yl] -phenanthtridyne

6- [7- (4-MethyleneoxyG4-phenyl) -9 H -fluoren-2-yl] -phenanthridine

Dissolve 6- [7- (4-Bromomethyl- phenyl) -9 H -fluoren-2-yl] -phenanthridine and G4-OH were prepared in acetone by addition of KOH. [Ligand 25]

¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H), 8.12 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H ), 7.77 (m, 2H), 7.73 (d, 1H), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H) , 7.37 (d, 2H), 7.29-7.43 (m, 82H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 ( s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (d, 2H).

Example 345

6- (6-methoxy-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-Methoxy-benzo [b] thiophen-2-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 6-Methoxy-benzo [b] thiophen-2-boronic acid with 6-bromo-phenanthtridine. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.75 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.41 (t, 1H), 7.31 (s, 1H), 6.81 (d, 1H), 3.73 (s, 3H).

Example 346

6- (6-OG1-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-OG1-benzo [b] thiophen-2-yl) -phenanthridine

Reaction of 6- (6-Hydroxy-benzo [b] thiophen-2-yl) -phenanthridine, G1-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.76 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.29-7.44 (m, 13H), 6.81 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4) , 5.08 (s, 2H), 5.03 (s, 4H).

Example 347

6- (6-OG2-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-OG2-benzo [b] thiophen-2-yl) -phenanthridine

Reaction of 6- (6-Hydroxy-benzo [b] thiophen-2-yl) -phenanthridine, G2-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.29-7.43 (m, 23H), 6.81 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 348

6- (6-OG3-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-OG3-benzo [b] thiophen-2-yl) -phenanthridine

Reaction of 6- (6-Hydroxy-benzo [b] thiophen-2-yl) -phenanthridine, G3-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.74 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.29-7.43 (m, 43H), 6.81 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H).

Example 349

6- (6-OG4-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-OG4-benzo [b] thiophen-2-yl) -phenanthridine

Reaction of 6- (6-Hydroxy-benzo [b] thiophen-2-yl) -phenanthridine, G4-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.76 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.29-7.43 (m, 83H), 6.81 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H).

Example 350

6- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -phenanthtridyne

6- (6-MethyleneoxyG1-benzo [b] thiophen-2-yl) -phenanthridine

6- (6-Bromomethyl-benzo [b] thiophen-2-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.74 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.30-7.49 (m, 13H), 6.81 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 351

6- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -phenanthtridyne

6- (6-MethyleneoxyG2-benzo [b] thiophen-2-yl) -phenanthridine

6- (6-Bromomethyl-benzo [b] thiophen-2-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.75 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.27-7.47 (m, 24H), 6.81 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 352

6- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -phenanthtridiin

6- (6-MethyleneoxyG3-benzo [b] thiophen-2-yl) -phenanthridine

6- (6-Bromomethyl-benzo [b] thiophen-2-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.27-7.41 (m, 44H), 6.81 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 353

6- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -phenanthtridyne

6- (6-MethyleneoxyG4-benzo [b] thiophen-2-yl) -phenanthridine

6- (6-Bromomethyl-benzo [b] thiophen-2-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.62 (t, 1H), 7.57 (t, 1H), 7.51 (t, 1H ), 7.29-7.43 (m, 84H), 6.81 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 354

6- (4-methoxy-naphthalene-1-yl) -phenanthtridiin

6- (4-Methoxy-naphthalen-1-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-naphthalen-1-boronic acid with 6-bromo-phenanthridine. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.32 (t, 1H), 6.71 (d, 1H), 3.73 (s, 3H).

Example 355

6- (4-OG1-naphthalene-1-yl) -phenanthtridiin

6- (4-OG1-naphthalen-1-yl) -phenanthridine

6- (4-Hydroxy-naphthalen-1-yl) -phenanthridine, G1-Br and 18-crown-6 were synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 7.87 (d, 1H), 8.01 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.44 (m, 13H), 6.72 (m, 3H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4 H).

Example 356

6- (4-OG2-naphthalene-1-yl) -phenanthtridyne

6- (4-OG2-naphthalen-1-yl) -phenanthridine

6- (4-Hydroxy-naphthalen-1-yl) -phenanthridine, G2-Br and 18-crown-6 were synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 6.71 (m, 3H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H) ), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 357

6- (4-OG3-naphthalene-1-yl) -phenanthtridiin

6- (4-OG3-naphthalen-1-yl) -phenanthridine

6- (4-Hydroxy-naphthalen-1-yl) -phenanthridine, G3-Br and 18-crown-6 were synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 43H), 6.71 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 358

6- (4-OG4-naphthalene-1-yl) -phenanthtridyne

6- (4-OG4-naphthalen-1-yl) -phenanthridine

6- (4-Hydroxy-naphthalen-1-yl) -phenanthridine, G4-Br and 18-crown-6 were synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 6.71 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 ( s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 359

6- (4-methyleneoxyG1-naphthalene-1-yl) -phenanthtridiin

6- (4-MethyleneoxyG1-naphthalen-1-yl) -phenanthridine

6- (4-Bromomethyl-naphthalen-1-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 6.71 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 360

6- (4-methyleneoxyG2-naphthalene-1-yl) -phenanthtridyne

6- (4-MethyleneoxyG2-naphthalen-1-yl) -phenanthridine

6- (4-Bromomethyl-naphthalen-1-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.27-7.47 (m, 24H), 6.71 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 361

6- (4-methyleneoxyG3-naphthalene-1-yl) -phenanthridine

6- (4-MethyleneoxyG3-naphthalen-1-yl) -phenanthridine

6- (4-Bromomethyl-naphthalen-1-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 44H), 6.71 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

Example 362

6- (4-methyleneoxyG4-naphthalene-1-yl) -phenanthridine

6- (4-MethyleneoxyG4-naphthalen-1-yl) -phenanthridine

6- (4-Bromomethyl-naphthalen-1-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 27]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (m, 3H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 84H), 6.71 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H) , J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 363

6- (5-methoxy-naphthalene-1-yl) -phenanthtridiin

6- (5-Methoxy-naphthalen-1-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-naphthalen-1-boronic acid with 6-bromo-phenanthridine. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.42 (m, 2H), 7.21 (t, 1H), 6.66 (d, 1H), 3.73 (s, 3H).

Example 364

6- (5-OG1-naphthalene-1-yl) -phenanthtridyne

6- (5-OG1-naphthalen-1-yl) -phenanthridine

6- (5-Hydroxy-naphthalen-1-yl) -phenanthridine, G1-Br and 18-crown-6 were synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.44 (m, 12H), 7.21 (t, 1H), 6.66 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.86 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 365

6- (5-OG2-naphthalene-1-yl) -phenanthtridyne

6- (5-OG2-naphthalen-1-yl) -phenanthridine

6- (5-Hydroxy-naphthalen-1-yl) -phenanthridine, G2-Br, and 18-crown-6 were synthesized by the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 22H), 7.21 (t, 1H), 6.66 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 366

6- (5-OG3-naphthalene-1-yl) -phenanthtridyne

6- (5-OG3-naphthalen-1-yl) -phenanthridine

The reaction of 6- (5-Hydroxy-naphthalen-1-yl) -phenanthridine, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 42H), 7.21 (t, 1H), 6.66 (d, 1H), 6.65-6.52 (m, 21H), 5.09 ( s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 367

6- (5-OG4-naphthalene-1-yl) -phenanthtridyne

6- (5-OG4-naphthalen-1-yl) -phenanthridine

6- (5-Hydroxy-naphthalen-1-yl) -phenanthridine, G4-Br, and 18-crown-6 were synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 82H), 7.21 (t, 1H), 6.66 (d, 1H), 6.65-6.48 (m, 45H), 5.09 ( s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 368

6- (5-methyleneoxyG1-naphthalene-1-yl) -phenanthtridiin

6- (5-MethyleneoxyG1-naphthalen-1-yl) -phenanthridine

6- (5-Bromomethyl-naphthalen-1-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 7.21 (t, 1H), 6.66 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 369

6- (5-MethyleneoxyG2-naphthalene-1-yl) -phenanthtridiin

6- (5-MethyleneoxyG2-naphthalen-1-yl) -phenanthridine

6- (5-Bromomethyl-naphthalen-1-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.42 (m, 2H), 7.27-7.47 (m, 21H), 7.21 (t, 1H), 6.67 (m, 5H), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2 H).

Example 370

6- (5-methyleneoxyG3-naphthalene-1-yl) -phenanthtridyne

6- (5-MethyleneoxyG3-naphthalen-1-yl) -phenanthridine

6- (5-Bromomethyl-naphthalen-1-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.42 (m, 2H), 7.27-7.41 (m, 41H), 7.21 (t, 1H), 6.66 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 371

6- (5-methyleneoxyG4-naphthalene-1-yl) -phenanthtridyne

6- (5-MethyleneoxyG4-naphthalen-1-yl) -phenanthridine

6- (5-Bromomethyl-naphthalen-1-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 28]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 7.21 (t, 1H), 6.62-6.67 (m, 44H), 6.57 (d, 2H, J = 2.4 ), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 372

6- (2, 3, 6-trifluoro-4'-methoxy-biphenyl-4-yl) -phenanthtridiin

6- (2, 3, 6-Trifluoro-4'-methoxy-biphenyl-4-yl) -phenanthridine

The desired product was synthesized by C-C coupling reaction of 2, 3, 6-Trifluoro-4'-methoxy-biphenyl-4-boronic acid with 6-bromo-phenanthtridine. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.41 (t, 1H), 7.38 (d, 2H), 6.86 (d, 2H), 3.73 (s, 3H).

Example 373

6- (2, 3, 6-trifluoro-4'-OG 1 -biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-OG1-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2, 3, 6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -phenanthridine, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.29-7.44 (m, 13H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 374

6- (2, 3, 6-trifluoro-4'-OG2-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-OG2-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2, 3, 6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -phenanthridine, G2-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.54 (s, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 23H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 375

6- (2, 3, 6-trifluoro-4'-OG3-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-OG3-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2, 3, 6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -phenanthridine, G3-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 43H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 376

6- (2, 3, 6-trifluoro-4'-OG4-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-OG4-biphenyl-4-yl) -phenanthridine

The reaction of 6- (2, 3, 6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -phenanthridine, G4-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 83H), 6.65-6.48 (m, 45H), 6.86 (d, 2H), 5.09 (s, 2H), 5.03 ( s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 377

6- (2, 3, 6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -phenanthtridyne

6- (2,3,6-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -phenanthridine and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.30-7.49 (m, 14H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

Example 378

6- (2, 3, 6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -phenanthtridyne

6- (2, 3, 6-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) phenanthridine

6- (2, 3, 6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -phenanthridine and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 23H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

Example 379

6- (2, 3, 6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -phenanthridine and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.41 (t, 1H), 7.27-7.41 (m, 43H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

Example 380

6- (2, 3, 6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -phenanthridine

6- (2, 3, 6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 29]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.41 (t, 1H), 7.29-7.43 (m, 83H), 6.86 (d, 2H), 6.62-6.67 (m, 43H), 6.57 ( d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 381

2- (2, 3 or 4-methoxy-phenyl) -benzothiazole

2- (2, 3 or 4-Methoxy-phenyl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 2, 3 or 4-Methoxy-benzene-1-boronic acid with 2-bromo-benzothiazole. [Ligand 31]

2- (4-methoxy-phenyl) -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.38 (d, 2H), 6.90 (d, 2H), 3.84 (d, 2H).

Example 382

2- (2-OG1-phenyl) -benzothiazole

2- (2-OG1-phenyl) -benzothiazole

The reaction of 2- (2-Hydroxy-phenyl) -benzothiazole, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

Example 383

2- (3-OG1-phenyl) -benzothiazole

2- (3-OG1-phenyl) -benzothiazole

The reaction of 2- (3-Hydroxy-phenyl) -benzothiazole, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 11H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s , 2H).

Example 384

2- (4-OG1-phenyl) -benzothiazole

2- (4-OG1-phenyl) -benzothiazole

The reaction of 2- (4-Hydroxy-phenyl) -benzothiazole, G1-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.44 (m, 12H), 6.90 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

Example 385

2- (2-OG2-phenyl) -benzothiazole

2- (2-OG2-phenyl) -benzothiazole

The reaction of 2- (2-Hydroxy-phenyl) -benzothiazole, G2-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 21H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 386

2- (3-OG2-phenyl) -benzothiazole

2- (3-OG2-phenyl) -benzothiazole

The reaction of 2- (3-Hydroxy-phenyl) -benzothiazole, G2-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 20H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 387

2- (4-OG2-phenyl) -benzothiazole

2- (4-OG2-phenyl) -benzothiazole

The reaction of 2- (4-Hydroxy-phenyl) -benzothiazole, G2-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 22H), 6.90 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 388

2- (2-OG3-phenyl) -benzothiazole

2- (2-OG3-phenyl) -benzothiazole

The reaction of 2- (2-Hydroxy-phenyl) -benzothiazole, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 41H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 389

2- (3-OG3-phenyl) -benzothiazole

2- (3-OG3-phenyl) -benzothiazole

The reaction of 2- (3-Hydroxy-phenyl) -benzothiazole, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 40H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H).

Example 390

2- (4-OG3-phenyl) -benzothiazole

2- (4-OG3-phenyl) -benzothiazole

The reaction of 2- (4-Hydroxy-phenyl) -benzothiazole, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 42H), 6.90 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 391

2- (2-OG4-phenyl) -benzothiazole

2- (2-OG4-phenyl) -benzothiazole

The reaction of 2- (2-Hydroxy-phenyl) -benzothiazole, G4-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 392

2- (3-OG4-phenyl) -benzothiazole

2- (3-OG4-phenyl) -benzothiazole

The reaction of 2- (3-Hydroxy-phenyl) -benzothiazole, G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 80H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H).

Example 393

2- (4-OG4-phenyl) -benzothiazole

2- (4-OG4-phenyl) -benzothiazole

The reaction of 2- (4-Hydroxy-phenyl) -benzothiazole, G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 82H), 6.90 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 394

2- (2-methyleneoxyG1-phenyl) -benzothiazole

2- (2-MethyleneoxyG1-phenyl) -benzothiazole

2- (2-Bromomethyl-phenyl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 395

2- (3-methyleneoxyG1-phenyl) -benzothiazole

2- (3-MethyleneoxyG1-phenyl) -benzothiazole

2- (3-Bromomethyl-phenyl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 11H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 396

2- (4-methyleneoxyG1-phenyl) -benzothiazole

2- (4-MethyleneoxyG1-phenyl) -benzothiazole

2- (4-Bromomethyl-phenyl) -benzothiazole and G1-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 12H), 6.90 (d, 2H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 397

2- (2-methyleneoxyG2-phenyl) -benzothiazole

2- (2-MethyleneoxyG2-phenyl) -benzothiazole

2- (2-Bromomethyl-phenyl) -benzothiazole and G2-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 398

2- (3-methyleneoxyG2-phenyl) -benzothiazole

2- (3-MethyleneoxyG2-phenyl) -benzothiazole

2- (3-Bromomethyl-phenyl) -benzothiazole and G2-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.47 (m, 21H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 399

2- (4-methyleneoxyG2-phenyl) -benzothiazole

2- (4-MethyleneoxyG2-phenyl) -benzothiazole

2- (4-Bromomethyl-phenyl) -benzothiazole and G2-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.47 (m, 22H), 6.90 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 400

2- (2-methyleneoxyG3-phenyl) -benzothiazole

2- (2-MethyleneoxyG3-phenyl) -benzothiazole

2- (2-Bromomethyl-phenyl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.41 (m, 41H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 401

2- (3-methyleneoxyG3-phenyl) -benzothiazole

2- (3-MethyleneoxyG3-phenyl) -benzothiazole

2- (3-Bromomethyl-phenyl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.41 (m, 41H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 402

2- (4-methyleneoxyG3-phenyl) -benzothiazole

2- (4-MethyleneoxyG3-phenyl) -benzothiazole

2- (4-Bromomethyl-phenyl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.27-7.41 (m, 42H), 6.90 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 403

2- (2-methyleneoxyG4-phenyl) -benzothiazole

2- (2-MethyleneoxyG4-phenyl) -benzothiazole

2- (2-Bromomethyl-phenyl) -benzothiazole and G4-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 404

2- (3-methyleneoxyG4-phenyl) -benzothiazole

2- (3-MethyleneoxyG4-phenyl) -benzothiazole

2- (3-Bromomethyl-phenyl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 80H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 405

2- (4-methyleneoxyG4-phenyl) -benzothiazole

2- (4-MethyleneoxyG4-phenyl) -benzothiazole

2- (4-Bromomethyl-phenyl) -benzothiazole and G4-OH were dissolved in acetone and KOH was added. [Ligand 31]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.29-7.43 (m, 82H), 6.90 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 406

2- (2 ', 3', or 4'-methoxy-biphenyl-4-yl) -benzothiazole

2- (2 ', 3', or 4'-Methoxy-biphenyl-4-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 2 ', 3', or 4'-Methoxy-biphenyl-4-boronic acid with 2-bromo-benzothiazole. [Ligand 32]

2- (2'-methoxy-biphenyl-4-yl) -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H ), 7.37 (d, 1H), 7.1 (t, 1H), 6.83 (m, 2H), 3.73 (s, 3H).

2- (3'-methoxy-biphenyl-4-yl) -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H ), 7.21 (t, 1H), 7.04 (m, 2H), 6.73 (d, 1H), 3.73 (s, 3H).

2- (4'-methoxy-biphenyl-4-yl) -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H ), 7.37 (d, 2H), 6.83 (d, 2H), 3.73 (s, 3H).

Example 407

2- (2'-OG1-biphenyl-4-yl) -benzothiazole

2- (2'-OG1-biphenyl-4-yl) -benzothiazole

2- (2'-Hydroxy-biphenyl-4-yl) -benzothiazole, G1-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.11 (t, 1H), 6.83 (m , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 408

2- (3'-OG1-biphenyl-4-yl) -benzothiazole

2- (3'-OG1-biphenyl-4-yl) -benzothiazole

2- (3'-Hydroxy-biphenyl-4-yl) -benzothiazole, G1-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 7.04 (m , 2H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 409

2- (4'-OG1-biphenyl-4-yl) -benzothiazole

2- (4'-OG1-biphenyl-4-yl) -benzothiazole

2- (4'-Hydroxy-biphenyl-4-yl) -benzothiazole, G1-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 12H), 6.83 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 410

2- (2'-OG2-biphenyl-4-yl) -benzothiazole

2- (2'-OG2-biphenyl-4-yl) -benzothiazole

2- (2'-Hydroxy-biphenyl-4-yl) -benzothiazole, G2-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 21H), 7.13 (t, 1H), 6.83 (m , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 411

2- (3'-OG2-biphenyl-4-yl) -benzothiazole

2- (3'-OG2-biphenyl-4-yl) -benzothiazole

2- (3'-Hydroxy-biphenyl-4-yl) -benzothiazole, G2-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 7.04 (m , 2H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 412

2- (4'-OG2-biphenyl-4-yl) -benzothiazole

2- (4'-OG2-biphenyl-4-yl) -benzothiazole

2- (4'-Hydroxy-biphenyl-4-yl) -benzothiazole, G2-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 22H), 6.83 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 413

2- (2'-OG3-biphenyl-4-yl) -benzothiazole

2- (2'-OG3-biphenyl-4-yl) -benzothiazole

2- (2'-Hydroxy-biphenyl-4-yl) -benzothiazole, G3-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 41H), 7.13 (t, 1H), 6.83 (m , 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 414

2- (3'-OG3-biphenyl-4-yl) -benzothiazole

2- (3'-OG3-biphenyl-4-yl) -benzothiazole

2- (3'-Hydroxy-biphenyl-4-yl) -benzothiazole, G3-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 7.04 (m , 2H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 415

2- (4'-OG3-biphenyl-4-yl) -benzothiazole

2- (4'-OG3-biphenyl-4-yl) -benzothiazole

2- (4'-Hydroxy-biphenyl-4-yl) -benzothiazole, G3-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 42H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 416

2- (2'-OG4-biphenyl-4-yl) -benzothiazole

2- (2'-OG4-biphenyl-4-yl) -benzothiazole

2- (2'-Hydroxy-biphenyl-4-yl) -benzothiazole, G4-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.17 (t, 1H), 6.83 (m , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 417

2- (3'-OG4-biphenyl-4-yl) -benzothiazole

2- (3'-OG4-biphenyl-4-yl) -benzothiazole

2- (3'-Hydroxy-biphenyl-4-yl) -benzothiazole, G4-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 7.04 (m , 2H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 418

2- (4'-OG4-biphenyl-4-yl) -benzothiazole

2- (4'-OG4-biphenyl-4-yl) -benzothiazole

2- (4'-Hydroxy-biphenyl-4-yl) -benzothiazole, G4-Br and 18-crown

The reaction of -6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 419

2- (2'-methyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (2'-MethyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (2'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.12 (m, 3H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 420

2- (3'-methyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (3'-MethyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (3'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 12H), 7.24 (t, 1H), 7.02 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 421

2- (4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (4'-MethyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (4'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 422

2- (2'-methyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (2'-MethyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (2'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 21H), 7.12 (m, 3H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 423

2- (3'-methyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (3'-MethyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (3'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 22H), 7.25 (t, 1H), 7.02 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 424

2- (4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (4'-MethyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (4'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 425

2- (2'-methyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (2'-MethyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (2'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.41 (m, 41H), 7.12 (m, 3H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 426

2- (3'-methyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (3'-MethyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (3'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.41 (m, 42H), 7.23 (t, 1H), 7.02 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 427

2- (4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (4'-MethyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (4'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 428

2- (2'-methyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (2'-MethyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (2'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.12 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 429

2- (3'-methyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (3'-MethyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (3'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 82H), 7.23 (t, 1H), 7.02 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 430

2- (4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (4'-MethyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (4'-Bromomethyl-biphenyl-4-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 32]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 431

2- (5-methoxy-thiophen-2-yl) -benzothiazole

2- (5-Methoxy-thiophen-2-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-thiophen-2-boronic acid and 2-bromo-benzothiazole. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 6.54 (d, 1H), 6.03 (d, 1H), 3.73 (s, 3H ).

Example 432

2- (5-OG1-thiophen-2-yl) -benzothiazole

2- (5-OG1-thiophen-2-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-thiophen-2-yl) -benzothiazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 6.65 (d, 2H, J = 3.9) 6.55 (t, 1H, J = 2.1), 6.50 (d, 1H), 6.10 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 433

2- (5-OG2-thiophen-2-yl) -benzothiazole

2- (5-OG2-thiophen-2-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-thiophen-2-yl) -benzothiazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 20H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 4H), 6.04 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 434

2- (5-OG3-thiophen-2-yl) -benzothiazole

2- (5-OG3-thiophen-2-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-thiophen-2-yl) -benzothiazole, G3-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 22H), 6.51 (d, 1H), 6.01 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 435

2- (5-OG4-thiophen-2-yl) -benzothiazole

2- (5-OG4-thiophen-2-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-thiophen-2-yl) -benzothiazole, G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 6.65-6.48 (m, 46H), 6.06 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 436

2- (5-methyleneoxyG1-thiophen-2-yl) -benzothiazole

2- (5-MethyleneoxyG1-thiophen-2-yl) -benzothiazole

2- (5-Bromomethyl-thiophen-2-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 6.73 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 437

2- (5-methyleneoxyG2-thiophen-2-yl) -benzothiazole

2- (5-MethyleneoxyG2-thiophen-2-yl) -benzothiazole

2- (5-Bromomethyl-thiophen-2-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 20H), 6.73 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 438

2- (5-methyleneoxyG3-thiophen-2-yl) -benzothiazole

2- (5-MethyleneoxyG3-thiophen-2-yl) -benzothiazole

2- (5-Bromomethyl-thiophen-2-yl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 40H), 6.71 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 439

2- (5-methyleneoxyG4-thiophen-2-yl) -benzothiazole

2- (5-MethyleneoxyG4-thiophen-2-yl) -benzothiazole

2- (5-Bromomethyl-thiophen-2-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Legal 33]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 6.72 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 440

2- [5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2, 3 or 4-Methoxy-phenyl) -thiophen-2-yl] -benzothiazole

The desired product was synthesized by C-C coupling reaction of 5- (2, 3, or 4-Methoxy-phenyl) -thiophen-2-boronic acid with 2-bromo-benzothiazole. [Ligand 34]

2- [5- (2-methoxy-phenyl) -thiophen-2-yl] -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.37 (d, 1H), 7.13 (t, 1H), 7.04 (d, 2H), 6.83 (m, 2H), 3.73 (s, 3H).

2- [5- (3-methoxy-phenyl) -thiophen-2-yl] -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.21 (t, 1H), 7.04 (m, 4H), 6.73 (d, 1H), 3.73 (s, 3H).

2- [5- (4-methoxy-phenyl) -thiophen-2-yl] -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.37 (d, 2H), 7.05 (d, 2H), 6.83 (d, 2H), 3.73 (s, 3H).

Example 441

2- [5- (2-OG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-OG1-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G1-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.15 (t, 1H), 7.05 (d , 2H), 6.83 (m, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 442

2- [5- (3-OG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-OG1-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G1-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 7.04 (m , 4H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 443

2- [5- (4-OG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-OG1-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G1-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.01 (d, 2H), 6.83 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 444

2- [5- (2-OG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-OG2-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G2-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 21H), 7.13 (t, 1H), 7.04 (d , 2H), 6.83 (m, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 445

2- [5- (3-OG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-OG2-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G2-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 7.02 (m , 4H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 446

2- [5- (4-OG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-OG2-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G2-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 7.04 (d, 2H), 6.83 (d , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 447

2- [5- (2-OG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-OG3-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G3-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 41H), 7.13 (t, 1H), 7.02 (d , 2H), 6.83 (m, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 448

2- [5- (3-OG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-OG3-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G3-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 7.04 (m , 4H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 449

2- [5- (4-OG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-OG3-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G3-Br and 18-crown-6 to generate ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 7.02 (d, 2H), 6.83 (d , 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 450

2- [5- (2-OG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-OG4-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G4-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 7.02 (d , 2H), 6.83 (m, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 451

2- [5- (3-OG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-OG4-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G4-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 7.06 (m , 4H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 452

2- [5- (4-OG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-OG4-phenyl) -thiophen-2-yl] -benzothiazole

Reaction of 2- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -benzothiazole, G4-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.03 (d, 2H), 6.83 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 453

2- [5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G1-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (m, 3H), 7.02 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 454

2- [5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-MethyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G1-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.21 (t, 1H), 7.03 (m , 3H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 455

2- [5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G1-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 7.05 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 456

2- [5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (m, 3H), 7.04 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 457

2- [5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-MethyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G2-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 22H), 7.23 (t, 1H), 7.05 (m , 3H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 458

2- [5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-MethyleneoxyG2-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 7.04 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 459

2- [5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.12 (m, 3H), 7.04 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 460

2- [5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-MethyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 42H), 7.23 (t, 1H), 7.03 (m , 3H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 461

2- [5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 7.04 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 462

2- [5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-MethyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G4-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (m, 3H), 7.05 (d , 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

Example 463

2- [5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-MethyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G4-OH were dissolved in acetone and KOH was added. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.22 (t, 1H), 7.02 (m , 3H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

Example 464

2- [5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-MethyleneoxyG4-phenyl) -thiophen-2-yl] -benzothiazole

2- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 34]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 7.02 (d , 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

Example 465

2- [7- (4-methoxy-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-Methoxy-phenyl) -9H-fluoren-2-yl] -benzothiazole

The desired product was synthesized by C-C coupling reaction of 7- (4-Methoxy-phenyl) -9H-fluoren-2-boronic acid with 2-bromo-benzothiazole. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.94 (d, 2H), 7.77 (s, 2H), 7.63 (d, 2H), 7.55 (m, 2H ), 7.37 (d, 2H), 6.83 (d, 2H), 3.87 (s, 2H), 3.73 (s, 3H).

Example 466

2- [7- (4-OG1-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-OG1-phenyl) -9H-fluoren-2-yl] -benzothiazole

Reaction of 2- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -benzothiazole, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.91 (d, 2H), 7.77 (s, 2H), 7.63 (d, 2H), 7.55 (m, 2H ), 7.30-7.49 (m, 12H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s , 4H), 3.87 (s, 2H).

Example 467

2- [7- (4-OG2-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-OG2-phenyl) -9H-fluoren-2-yl] -benzothiazole

Reaction of 2- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -benzothiazole, G2-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.94 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 22H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.87 (s, 2H).

Example 468

2- [7- (4-OG3-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-OG3-phenyl) -9H-fluoren-2-yl] -benzothiazole

Reaction of 2- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -benzothiazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.92 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 42H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H), 3.87 (s, 2H).

Example 469

2- [7- (4-OG4-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-OG4-phenyl) -9H-fluoren-2-yl] -benzothiazole

Reaction of 2- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -benzothiazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.94 (d, 2H), 7.77 (s, 2H), 7.64 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H), 3.87 (s, 2 H).

Example 470

2- [7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-MethyleneoxyG1-phenyl) -9H-fluoren-2-yl] -benzothiazole

2- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.93 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s , 2H), 4.53 (s, 2H), 3.87 (s, 2H).

Example 471

2- [7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-MethyleneoxyG2-phenyl) -9H-fluoren-2-yl] -benzothiazole

2- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.93 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.87 (s, 2H).

Example 472

2- [7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-MethyleneoxyG3-phenyl) -9H-fluoren-2-yl] -benzothiazole

2- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.93 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 2H).

Example 473

2- [7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl] -benzothiazole

2- [7- (4-MethyleneoxyG4-phenyl) -9H-fluoren-2-yl] -benzothiazole

2- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [35]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.92 (d, 2H), 7.77 (s, 2H), 7.63 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 2H).

Example 474

2- (6-methoxy-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-Methoxy-benzo [b] thiophen-2-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 6-Methoxy-benzo [b] thiophen-2-boronic acid and 2-bromo-benzothiazole. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.74 (d, 1H), 7.55 (m, 2H), 7.42 (s, 1H), 7.33 (s, 1H ), 6.83 (d, 1 H), 3.73 (s, 3 H).

Example 475

2- (6-OG1-Benzo [b] thiophen-2-yl) -benzothiazole

2- (6-OG1-benzo [b] thiophen-2-yl) -benzothiazole

Reaction of 2- (6-Hydroxy-benzo [b] thiophen-2-yl) -benzothiazole, G1-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 6.83 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 476

2- (6-OG2-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-OG2-benzo [b] thiophen-2-yl) -benzothiazole

Reaction of 2- (6-Hydroxy-benzo [b] thiophen-2-yl) -benzothiazole, G2-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 6.82 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 477

2- (6-OG3-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-OG3-benzo [b] thiophen-2-yl) -benzothiazole

Reaction of 2- (6-Hydroxy-benzo [b] thiophen-2-yl) -benzothiazole, G3-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.76 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 6.82 (d , 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 478

2- (6-OG4-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-OG4-benzo [b] thiophen-2-yl) -benzothiazole

Reaction of 2- (6-Hydroxy-benzo [b] thiophen-2-yl) -benzothiazole, G4-Br and 18-crown-6 to produce ether (R'-OR) reaction of hydroxy-aryl and bromo-alkylpyridine Through synthesis. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 6.81 (d , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 479

2- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-MethyleneoxyG1-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-Bromomethyl-benzo [b] thiophen-2-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.76 (m, 2H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.14 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 480

2- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-MethyleneoxyG2-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-Bromomethyl-benzo [b] thiophen-2-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (m, 2H), 7.55 (m, 2H), 7.27-7.47 (m, 21H), 7.11 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 481

2- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-MethyleneoxyG3-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-Bromomethyl-benzo [b] thiophen-2-yl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.71 (m, 2H), 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.13 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 482

2- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-MethyleneoxyG4-benzo [b] thiophen-2-yl) -benzothiazole

2- (6-Bromomethyl-benzo [b] thiophen-2-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 36]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (m, 2H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.11 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 483

2- (4-methoxy-naphthalein-1-yl) -benzothiazole

2- (4-Methoxy-naphthalen-1-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-naphthalen-1-boronic acid and 2-bromo-benzothiazole. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.22 (m, 2H), 8.12 (d, 1H), 7.75 (d, 1H), 7.55 (m, 2H), 7.43 (m, 2H), 7.32 (t, 1H ), 6.74 (d, 1 H), 3.73 (s, 3 H).

Example 484

2- (4-OG1-naphthalein-1-yl) -benzothiazole

2- (4-OG1-naphthalen-1-yl) -benzothiazole

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) -benzothiazole, G1-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.22 (m, 2H), 8.12 (d, 1H), 7.74 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 13H), 6.72 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 485

2- (4-OG2-naphthalein-1-yl) -benzothiazole

2- (4-OG2-naphthalen-1-yl) -benzothiazole

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) -benzothiazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.22 (m, 2H), 8.12 (d, 1H), 7.73 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 23H), 6.74 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 486

2- (4-OG3-naphthalein-1-yl) -benzothiazole

2- (4-OG3-naphthalen-1-yl) -benzothiazole

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) -benzothiazole, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.22 (m, 2H), 8.12 (d, 1H), 7.73 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 43H), 6.71 (d , 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 487

2- (4-OG4-naphthalein-1-yl) -benzothiazole

2- (4-OG4-naphthalen-1-yl) -benzothiazole

The reaction of 2- (4-Hydroxy-naphthalen-1-yl) -benzothiazole, G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.22 (m, 2H), 8.12 (d, 1H), 7.7 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 83H), 6.70 (d , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 488

2- (4-methyleneoxyG1-naphthalein-1-yl) -benzothiazole

2- (4-MethyleneoxyG1-naphthalen-1-yl) -benzothiazole

2- (4-Bromomethyl-naphthalen-1-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.81 (d, 1H), 7.62 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m , 13H), 7.21 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

Example 489

2- (4-methyleneoxyG2-naphthalein-1-yl) -benzothiazole

2- (4-MethyleneoxyG2-naphthalen-1-yl) -benzothiazole

2- (4-Bromomethyl-naphthalen-1-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.82 (d, 1H), 7.63 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m , 23H), 7.21 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 490

2- (4-methyleneoxyG3-naphthalein-1-yl) -benzothiazole

2- (4-MethyleneoxyG3-naphthalen-1-yl) -benzothiazole

2- (4-Bromomethyl-naphthalen-1-yl) -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.81 (d, 1H), 7.63 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m , 43H), 7.23 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 491

2- (4-methyleneoxyG4-naphthalein-1-yl) -benzothiazole

2- (4-MethyleneoxyG4-naphthalen-1-yl) -benzothiazole

2- (4-Bromomethyl-naphthalen-1-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Reed 37]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.83 (d, 1H), 7.62 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m , 83H), 7.20 (d, 1H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H ), 4.52 (d, 2 H).

Example 492

2- (5-methoxy-naphthalein-1-yl) -benzothiazole

2- (5-Methoxy-naphthalen-1-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-naphthalen-1-boronic acid with 2-bromo-benzothiazole. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.63 (d, 1H), 7.55 (m, 2H), 7.42 (t, 1H), 7.33 (d, 1H ), 7.22 (t, 1 H), 6.61 (d, 1 H), 3.73 (s, 3 H).

Example 493

2- (5-OG1-naphthalein-1-yl) -benzothiazole

2- (5-OG1-naphthalen-1-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) -benzothiazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.6 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.21 (t , 1H), 6.65 (d, 2H, J = 3.9), 6.62 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 494

2- (5-OG2-naphthalein-1-yl) -benzothiazole

2- (5-OG2-naphthalen-1-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) -benzothiazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.62 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 7.21 (t , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.61 (d, 1H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 495

2- (5-OG3-naphthalein-1-yl) -benzothiazole

2- (5-OG3-naphthalen-1-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) -benzothiazole, G3-Br and 18-crown-6 was synthesized through ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.64 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 7.23 (t , 1H), 6.65-6.52 (m, 23H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 496

2- (5-OG4-naphthalein-1-yl) -benzothiazole

2- (5-OG4-naphthalen-1-yl) -benzothiazole

The reaction of 2- (5-Hydroxy-naphthalen-1-yl) -benzothiazole, G4-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.64 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.21 (t , 1H), 6.65-6.48 (m, 46H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 497

2- (5-methyleneoxyG1-naphthalein-1-yl) -benzothiazole

2- (5-MethyleneoxyG1-naphthalen-1-yl) -benzothiazole

2- (5-Bromomethyl-naphthalen-1-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.7 (d, 1H), 7.55 (m, 4H), 7.30-7.49 (m, 11H), 7.23 (t , 1H), 7.13 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

Example 498

2- (5-methyleneoxyG2-naphthalein-1-yl) -benzothiazole

2- (5-MethyleneoxyG2-naphthalen-1-yl) -benzothiazole

2- (5-Bromomethyl-naphthalen-1-yl) -benzothiazole and G2-OH were dissolved in acetone and KOH was added. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.73 (d, 1H), 7.55 (m, 4H), 7.27-7.47 (m, 21H), 7.22 (t , 1H), 7.13 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 499

2- (5-methyleneoxyG3-naphthalein-1-yl) -benzothiazole

2- (5-MethyleneoxyG3-naphthalen-1-yl) -benzothiazole

2- (5-Bromomethyl-naphthalen-1-yl) -benzothiazole and G3-OH were dissolved in acetone and KOH was added. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.74 (d, 1H), 7.55 (m, 4H), 7.27-7.41 (m, 41H), 7.22 (t , 1H), 7.13 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 500

2- (5-methyleneoxyG4-naphthalein-1-yl) -benzothiazole

2- (5-MethyleneoxyG4-naphthalen-1-yl) -benzothiazole

2- (5-Bromomethyl-naphthalen-1-yl) -benzothiazole and G4-OH were dissolved in acetone and KOH was added. [Ligand 38]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (m, 2H), 7.73 (d, 1H), 7.55 (m, 4H), 7.29-7.43 (m, 81H), 7.22 (t , 1H), 7.11 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 501

2- (2,3,5-Trifluoro-4'-methoxy-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-methoxy-biphenyl-4-yl) -benzothiazole

The desired product was synthesized by C-C coupling reaction of 2,3,5-Trifluoro-4'-methoxy-biphenyl-4-boronic acid and 2-bromo-benzothiazole. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.37 (d, 2H), 7.09 (s, 1H), 6.83 (d, 2H ), 3.73 (s, 3 H).

Example 502

2- (2,3,5-Trifluoro-4'-OG 1 -biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-OG1-biphenyl-4-yl) -benzothiazole

Reactions of 2- (2,3,5-Trifluoro-4'-hydroxy-biphenyl-4-yl) -benzothiazole, G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.02 (s, 1H), 6.83 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

Example 503

2- (2,3,5-Trifluoro-4'-OG2-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-OG2-biphenyl-4-yl) -benzothiazole

Reactions of 2- (2,3,5-Trifluoro-4'-hydroxy-biphenyl-4-yl) -benzothiazole, G2-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 7.02 (s, 1H), 6.83 (d , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 504

2- (2,3,5-Trifluoro-4'-OG3-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-OG3-biphenyl-4-yl) -benzothiazole

Reactions of 2- (2,3,5-Trifluoro-4'-hydroxy-biphenyl-4-yl) -benzothiazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 7.03 (s, 1H), 6.83 (d , 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 505

2- (2,3,5-Trifluoro-4'-OG 4 -biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-OG4-biphenyl-4-yl) -benzothiazole

Reactions of 2- (2,3,5-Trifluoro-4'-hydroxy-biphenyl-4-yl) -benzothiazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'- OR) through synthesis reaction. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.03 (s, 1H), 6.83 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 506

2- (2,3,5-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -benzothiazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 507

2- (2,3,5-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -benzothiazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 508

2- (2,3,5-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -benzothiazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 509

2- (2,3,5-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazole

2- (2,3,5-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -benzothiazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 39]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 510

1- (2, 3 or 4-methoxy-phenyl) -1H-pyrazole

1- (2, 3 or 4-Methoxy-phenyl) -1H-Pyrazole

The desired product was synthesized by C-C coupling reaction of 2, 3 or 4-Methoxy-1-boronic acid with 1-bromo-1H-pyrazole. [Ligand 41]

1- (2-methoxy-phenyl) -1 H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.24 (m, 2H), 6.85 (m , 2H), 6.46 (t, 1H), 3.78 (s, 3H).

1- (3-methoxy-phenyl) -1H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.23 (t, 1H), 6.82 (m , 3H), 6.46 (t, 1H), 3.73 (s, 3H).

1- (4-methoxy-phenyl) -1 H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.23 (d, 2H), 6.85 (d , 2H), 6.46 (t, 1H), 3.73 (s, 3H).

Example 511

1- (2-OG1-phenyl) -1H-pyrazole

1- (2-OG1-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -1H-Pyrazole, G1-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.21 (m, 2H), 6.83 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 512

1- (3-OG1-phenyl) -1H-pyrazole

1- (3-OG1-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -1H-Pyrazole, G1-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 6.84 (m, 3H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 513

1- (4-OG1-phenyl) -1H-pyrazole

1- (4-OG1-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -1H-Pyrazole, G1-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.24 (d, 2H), 6.85 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 514

1- (2-OG2-phenyl) -1H-pyrazole

1- (2-OG2-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -1H-Pyrazole, G2-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 20H), 7.22 (m, 2H), 6.85 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 515

1- (3-OG2-phenyl) -1H-pyrazole

1- (3-OG2-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -1H-Pyrazole, G2-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 6.83 (m, 3H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 516

1- (4-OG2-phenyl) -1H-pyrazole

1- (4-OG2-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -1H-Pyrazole, G2-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 20H), 7.24 (d, 2H), 6.83 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 517

1- (2-OG3-phenyl) -1H-pyrazole

1- (2-OG3-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -1H-Pyrazole, G3-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 40H), 7.23 (m, 2H), 6.82 (m, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 518

1- (3-OG3-phenyl) -1H-pyrazole

1- (3-OG3-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (3-Hydroxy-phenyl) -1H-Pyrazole, G3-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 6.88 (m, 3H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 519

1- (4-OG3-phenyl) -1H-pyrazole

1- (4-OG3-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -1H-Pyrazole, G3-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 40H), 7.25 (d, 2H), 6.85 (d, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 520

1- (2-OG4-phenyl) -1H-pyrazole

1- (2-OG4-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (2-Hydroxy-phenyl) -1H-Pyrazole, G4-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.24 (m, 2H), 6.82 (m, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 521

1- (3-OG4-phenyl) -1H-pyrazole

1- (3-OG4-phenyl) -1H-Pyrazole

1- (3-Hydroxy-phenyl) -1H-Pyrazole, G4-Br and 18-crown-6 were synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 6.85 (m, 3H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 522

1- (4-OG4-phenyl) -1H-pyrazole

1- (4-OG4-phenyl) -1H-Pyrazole

It was synthesized by C-C coupling reaction of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- (4-Hydroxy-phenyl) -1H-Pyrazole, G4-Br and 18-crown-6. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.22 (d, 2H), 6.85 (d, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 523

1- (2-methyleneoxyG1-phenyl) -1H-pyrazole

1- (2-MethyleneoxyG1-phenyl) -1H-Pyrazole

1- (2-Bromomethyl-phenyl) -1H-Pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.11 (m, 4H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 524

1- (3-methyleneoxyG1-phenyl) -1H-pyrazole

1- (3-MethyleneoxyG1-phenyl) -1H-Pyrazole

1- (3-Bromomethyl-phenyl) -1H-Pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.15 (m, 4H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 525

1- (4-methyleneoxyG1-phenyl) -1H-pyrazole

1- (4-MethyleneoxyG1-phenyl) -1H-Pyrazole

1- (4-Bromomethyl-phenyl) -1H-Pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 10H), 7.11 (m, 4H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 526

1- (2-methyleneoxyG2-phenyl) -1H-pyrazole

1- (2-MethyleneoxyG2-phenyl) -1H-Pyrazole

1- (2-Bromomethyl-phenyl) -1H-Pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 20H), 7.12 (m, 4H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 527

1- (3-methyleneoxyG2-phenyl) -1H-pyrazole

1- (3-MethyleneoxyG2-phenyl) -1H-Pyrazole

1- (3-Bromomethyl-phenyl) -1H-Pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 20H), 7.15 (m, 4H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 528

1- (4-methyleneoxyG2-phenyl) -1H-pyrazole

1- (4-MethyleneoxyG2-phenyl) -1H-Pyrazole

1- (4-Bromomethyl-phenyl) -1H-Pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 20H), 7.13 (m, 4H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 529

1- (2-methyleneoxyG3-phenyl) -1H-pyrazole

1- (2-MethyleneoxyG3-phenyl) -1H-Pyrazole

1- (2-Bromomethyl-phenyl) -1H-Pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 40H), 7.14 (m, 4H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 530

1- (3-methyleneoxyG3-phenyl) -1H-pyrazole

1- (3-MethyleneoxyG3-phenyl) -1H-Pyrazole

1- (3-Bromomethyl-phenyl) -1H-Pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 40H), 7.11 (m, 4H), 6.73 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 531

1- (4-methyleneoxyG3-phenyl) -1H-pyrazole

1- (4-MethyleneoxyG3-phenyl) -1H-Pyrazole

1- (4-Bromomethyl-phenyl) -1H-Pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 40H), 7.14 (m, 4H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.52 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 532

1- (2-methyleneoxyG4-phenyl) -1H-pyrazole

1- (2-MethyleneoxyG4-phenyl) -1H-Pyrazole

1- (2-Bromomethyl-phenyl) -1H-Pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.12 (m, 4H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 534

1- (3-methyleneoxyG4-phenyl) -1H-pyrazole

1- (3-MethyleneoxyG4-phenyl) -1H-Pyrazole

1- (3-Bromomethyl-phenyl) -1H-Pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.12 (m, 4H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 535

1- (4-methyleneoxyG4-phenyl) -1H-pyrazole

1- (4-MethyleneoxyG4-phenyl) -1H-Pyrazole

1- (4-Bromomethyl-phenyl) -1H-Pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 41]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 80H), 7.14 (m, 4H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 536

1- (2 ', 3' or 4'-methoxy-biphenyl) -1H-pyrazole

1- (2 ', 3' or 4'-Methoxy-biphenyl) -1H-Pyrazole

The desired product was synthesized by C-C coupling reaction of 2 ', 3' or 4'-Methoxy-biphenyl-4-boronic acid with 1-bromo-1H-pyrazole. [Ligand 42]

1- (2'-methoxy-biphenyl) -1H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.55 (d, 2H), 7.37 (d, 1H), 7.31 (d, 2H), 7.12 (t, 1H), 6.85 (m, 2H), 6.46 (t, 1H), 3.73 (s, 3H).

1- (3'-methoxy-biphenyl) -1H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.52 (d, 2H), 7.31 (d, 2H), 7.21 (t, 1H), 7.02 (m, 2H), 6.73 (d, 1H), 6.46 (t, 1H), 3.73 (s, 3H).

1- (4'-methoxy-biphenyl) -1H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.53 (d, 2H), 7.37 (d, 2H), 7.32 (d, 2H), 6.83 (d, 2H), 6.46 (t, 1H), 3.73 (s, 3H).

Example 537

1- (2'-OG1-biphenyl) -1H-pyrazole

1- (2'-OG1-biphenyl) -1H-Pyrazole

The reaction of 1- (2'-Hydroxy-biphenyl) -1H-Pyrazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 15H), 7.13 (t, 1H), 6.83 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 538

1- (3'-OG1-biphenyl) -1H-pyrazole

1- (3'-OG1-biphenyl) -1H-Pyrazole

The reaction of 1- (3'-Hydroxy-biphenyl) -1H-Pyrazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 14H), 7.21 (t, 1H), 7.04 (m, 2H), 6.73 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 539

1- (4'-OG1-biphenyl) -1H-pyrazole

1- (4'-OG1-biphenyl) -1H-Pyrazole

The reaction of 1- (4'-Hydroxy-biphenyl) -1H-Pyrazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 16H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 540

1- (5'-OG1-biphenyl) -1H-pyrazole

1- (5'-OG1-biphenyl) -1H-Pyrazole

The reaction of 1- (5'-Hydroxy-biphenyl) -1H-Pyrazole, G1-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 14H), 7.21 (t, 1H), 7.01 (m, 2H), 6.73 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 541

1- (2'-OG2-biphenyl) -1H-pyrazole

1- (2'-OG2-biphenyl) -1H-Pyrazole

The reaction of 1- (2'-Hydroxy-biphenyl) -1H-Pyrazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 25H), 7.13 (t, 1H), 6.83 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 542

1- (3'-OG2-biphenyl) -1H-pyrazole

1- (3'-OG2-biphenyl) -1H-Pyrazole

The reaction of 1- (3'-Hydroxy-biphenyl) -1H-Pyrazole, G2-Br and 18-crown-6 was synthesized by ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 24H), 7.21 (t, 1H), 7.0 (m, 2H), 6.73 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 543

1- (4'-OG2-biphenyl) -1H-pyrazole

1- (4'-OG2-biphenyl) -1H-Pyrazole

The reaction of 1- (4'-Hydroxy-biphenyl) -1H-Pyrazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 26H), 6.83 (d, 2H), 6.73 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 544

1- (5'-OG2-biphenyl) -1H-pyrazole

1- (5'-OG2-biphenyl) -1H-Pyrazole

The reaction of 1- (5'-Hydroxy-biphenyl) -1H-Pyrazole, G2-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 24H), 7.21 (t, 1H), 7.01 (m, 2H), 6.73 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 545

1- (2'-OG3-biphenyl) -1H-pyrazole

1- (2'-OG3-biphenyl) -1H-Pyrazole

The reaction of 1- (2'-Hydroxy-biphenyl) -1H-Pyrazole, G3-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 45H), 7.1 (t, 1H), 6.8 (m, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 546

1- (3'-OG3-biphenyl) -1H-pyrazole

1- (3'-OG3-biphenyl) -1H-Pyrazole

The reaction of 1- (3'-Hydroxy-biphenyl) -1H-Pyrazole, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 44H), 7.21 (t, 1H), 7.03 (m, 2H), 6.73 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.94 (s, 4H).

Example 547

1- (4'-OG3-biphenyl) -1H-pyrazole

1- (4'-OG3-biphenyl) -1H-Pyrazole

The reaction of 1- (4'-Hydroxy-biphenyl) -1H-Pyrazole, G3-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 46H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 548

1- (5'-OG3-biphenyl) -1H-pyrazole

1- (5'-OG3-biphenyl) -1H-Pyrazole

The reaction of 1- (5'-Hydroxy-biphenyl) -1H-Pyrazole, G3-Br and 18-crown-6 was synthesized by ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 44H), 7.21 (t, 1H), 7.06 (m, 2H), 6.73 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 549

1- (2'-OG4-biphenyl) -1H-pyrazole

1- (2'-OG4-biphenyl) -1H-Pyrazole

The reaction of 1- (2'-Hydroxy-biphenyl) -1H-Pyrazole, G4-Br and 18-crown-6 was synthesized through ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 85H), 7.11 (t, 1H), 6.83 (m, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 550

1- (3'-OG4-biphenyl) -1H-pyrazole

1- (3'-OG4-biphenyl) -1H-Pyrazole

The reaction of 1- (3'-Hydroxy-biphenyl) -1H-Pyrazole, G4-Br and 18-crown-6 was synthesized by ether (R'-O-R) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 84H), 7.21 (t, 1H), 7.02 (m, 2H), 6.73 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 551

1- (4'-OG4-biphenyl) -1H-pyrazole

1- (4'-OG4-biphenyl) -1H-Pyrazole

The reaction of 1- (4'-Hydroxy-biphenyl) -1H-Pyrazole, G4-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 86H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 552

1- (5'-OG4-biphenyl) -1H-pyrazole

1- (5'-OG4-biphenyl) -1H-Pyrazole

The reaction of 1- (5'-Hydroxy-biphenyl) -1H-Pyrazole, G4-Br and 18-crown-6 was synthesized through the reaction of ether (R'-O-R) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 84H), 7.21 (t, 1H), 7.0 (m, 2H), 6.73 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 553

1- (2'-methyleneoxyG1-biphenyl) -1H-pyrazole

1- (2'-MethyleneoxyG1-biphenyl) -1H-Pyrazole

1- (2'-Bromomethyl-biphenyl) -1H-Pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 15H), 7.12 (m, 3H), 6.65 (d, 2H, J = 3.9 ), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 554

1- (3'-methyleneoxyG1-biphenyl) -1H-pyrazole

1- (3'-MethyleneoxyG1-biphenyl) -1H-Pyrazole

1- (3'-Bromomethyl-biphenyl) -1H-Pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 16H), 7.21 (t, 1H), 7.02 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 555

1- (4'-methyleneoxyG1-biphenyl) -1H-pyrazole

1- (4'-MethyleneoxyG1-biphenyl) -1H-Pyrazole

1- (4'-Bromomethyl-biphenyl) -1H-Pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 16H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 556

1- (5'-methyleneoxyG1-biphenyl) -1H-pyrazole

1- (5'-MethyleneoxyG1-biphenyl) -1H-Pyrazole

1- (5'-Bromomethyl-biphenyl) -1H-Pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 16H), 7.21 (t, 1H), 7.02 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 557

1- (2'-methyleneoxyG2-biphenyl) -1H-pyrazole

1- (2'-MethyleneoxyG2-biphenyl) -1H-Pyrazole

1- (2'-Bromomethyl-biphenyl) -1H-Pyrazole, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 25H), 7.1 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 558

1- (3'-methyleneoxyG2-biphenyl) -1H-pyrazole

1- (3'-MethyleneoxyG2-biphenyl) -1H-Pyrazole

1- (3'-Bromomethyl-biphenyl) -1H-Pyrazole, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 26H), 7.2 (t, 1H), 7.02 (d, 1H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 559

1- (4'-methyleneoxyG2-biphenyl) -1H-pyrazole

1- (4'-MethyleneoxyG2-biphenyl) -1H-Pyrazole

1- (4'-Bromomethyl-biphenyl) -1H-Pyrazole, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 26H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 560

1- (5'-methyleneoxyG2-biphenyl) -1H-pyrazole

1- (5'-MethyleneoxyG2-biphenyl) -1H-Pyrazole

1- (5'-Bromomethyl-biphenyl) -1H-Pyrazole, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 26H), 7.21 (t, 1H), 7.02 (d, 1H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 561

1- (2'-methyleneoxyG3-biphenyl) -1H-pyrazole

1- (2'-MethyleneoxyG3-biphenyl) -1H-Pyrazole

1- (2'-Bromomethyl-biphenyl) -1H-Pyrazole, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 45H), 7.1 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 562

1- (3'-methyleneoxyG3-biphenyl) -1H-pyrazole

1- (3'-MethyleneoxyG3-biphenyl) -1H-Pyrazole

1- (3'-Bromomethyl-biphenyl) -1H-Pyrazole, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 46H), 7.24 (t, 1H), 7.02 (d, 1H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 563

1- (4'-methyleneoxyG3-biphenyl) -1H-pyrazole

1- (4'-MethyleneoxyG3-biphenyl) -1H-Pyrazole

1- (4'-Bromomethyl-biphenyl) -1H-Pyrazole, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 46H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 564

1- (5'-methyleneoxyG3-biphenyl) -1H-pyrazole

1- (5'-MethyleneoxyG3-biphenyl) -1H-Pyrazole

1- (5'-Bromomethyl-biphenyl) -1H-Pyrazole, G3-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 46H), 7.21 (t, 1H), 7.02 (d, 1H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 565

1- (2'-methyleneoxyG4-biphenyl) -1H-pyrazole

1- (2'-MethyleneoxyG4-biphenyl) -1H-Pyrazole

1- (2'-Bromomethyl-biphenyl) -1H-Pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 85H), 7.1 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 566

1- (3'-methyleneoxyG4-biphenyl) -1H-pyrazole

1- (3'-MethyleneoxyG4-biphenyl) -1H-Pyrazole

1- (3'-Bromomethyl-biphenyl) -1H-Pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 86H), 7.2 (t, 1H), 7.02 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 567

1- (4'-methyleneoxyG4-biphenyl) -1H-pyrazole

1- (4'-MethyleneoxyG4-biphenyl) -1H-Pyrazole

1- (4'-Bromomethyl-biphenyl) -1H-Pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 86H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 568

1- (5'-methyleneoxyG4-biphenyl) -1H-pyrazole

1- (5'-MethyleneoxyG4-biphenyl) -1H-Pyrazole

1- (5'-Bromomethyl-biphenyl) -1H-Pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 42]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 86H), 7.21 (t, 1H), 7.02 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 569

1- (5-methoxy-thiophen-2-yl) -1H-pyrazole

1- (5-Methoxy-thiophen-2-yl) -1H-Pyrazole

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-thiophen-2-boronic acid with 1-bromo-1H-pyrazole. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.64 (m, 2H), 6.55 (d, 1H), 6.23 (t, 1H), 6.05 (d, 1H), 3.73 (s, 3H).

Example 570

1- (5-OG1-thiophen-2-yl) -1H-pyrazole

1- (5-OG1-thiophen-2-yl) -1H-Pyrazole

Synthesis of 1- (5-Hydroxy-thiophen-2-yl) -1H-Pyrazole, G1-Br, and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.64 (m, 2H), 7.30-7.49 (m, 10H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.50 ( d, 1H), 6.21 (t, 1H), 6.03 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 571

1- (5-OG2-thiophen-2-yl) -1H-pyrazole

1- (5-OG2-thiophen-2-yl) -1H-Pyrazole

Synthesis of 1- (5-Hydroxy-thiophen-2-yl) -1H-Pyrazole, G2-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 20H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54- 6.58 (m, 3H), 6.55 (d, 1H), 6.23 (t, 1H), 6.04 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 572

1- (5-OG3-thiophen-2-yl) -1H-pyrazole

1- (5-OG3-thiophen-2-yl) -1H-Pyrazole

Synthesis of 1- (5-Hydroxy-thiophen-2-yl) -1H-Pyrazole, G3-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.63 (m, 2H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 22H), 6.53 (d, 1H), 6.24 (t, 1H), 6.0 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 573

1- (5-OG4-thiophen-2-yl) -1H-pyrazole

1- (5-OG4-thiophen-2-yl) -1H-Pyrazole

Synthesis of 1- (5-Hydroxy-thiophen-2-yl) -1H-Pyrazole, G4-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.63 (m, 2H), 7.29-7.43 (m, 80H), 6.65-6.48 (m, 45H), 6.51 (d, 1H), 6.23 (t, 1H), 6.0 (d, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 574

1- (5-methyleneoxyG1-thiophen-2-yl) -1H-pyrazole

1- (5-MethyleneoxyG1-thiophen-2-yl) -1H-Pyrazole

1- (5-Bromomethyl-thiophen-2-yl) -1H-Pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.30-7.49 (m, 10H), 6.7 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.60 (d, 1H) , 6.55 (t, 1H, J = 2.1), 6.23 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 575

1- (5-methyleneoxyG2-thiophen-2-yl) -1H-pyrazole

1- (5-MethyleneoxyG2-thiophen-2-yl) -1H-Pyrazole

1- (5-Bromomethyl-thiophen-2-yl) -1H-Pyrazole, G2-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.27-7.47 (m, 20H), 6.7 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.61 (d, 1H), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 576

1- (5-methyleneoxyG3-thiophen-2-yl) -1H-pyrazole

1- (5-MethyleneoxyG3-thiophen-2-yl) -1H-Pyrazole

1- (5-Bromomethyl-thiophen-2-yl) -1H-Pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.27-7.41 (m, 40H), 6.7 (d, 1H), 6.67 (m, 9H), 6.64 (d, 4H, J = 2.4) , 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H) , 4.52 (d, 2 H).

Example 577

1- (5-methyleneoxyG4-thiophen-2-yl) -1H-pyrazole

1- (5-MethyleneoxyG4-thiophen-2-yl) -1H-Pyrazole

1- (5-Bromomethyl-thiophen-2-yl) -1H-Pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 43]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 80H), 6.73 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.66 (d, 1H), 6.57 (d, 2H, J = 2.4), 6.26 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 578

1- [5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2, 3 or 4-Methoxy-phenyl) -thiophen-2-yl] -1H-Pyrazole

The desired product was synthesized by C-C coupling reaction of 5- (4-Methoxy-phenyl) -thiophen-2-boronic acid with 1-bromo-1H-pyrazole. [Ligand 44]

1- [5- (2-methoxy-phenyl) -thiophen-2-yl] -1 H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.65 (m, 2H), 7.37 (d, 1H) , 7.15 (t, 1 H), 7.02 (d, 2H), 6.8 (m, 2H), 6.24 (t, 1H), 3.73 (s, 3H).

1- [5- (3-methoxy-phenyl) -thiophen-2-yl] -1 H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.65 (m, 2H), 7.24 (t, 1H) , 7.04 (m, 4H), 6.73 (d, 1H), 6.2 (t, 1H), 3.73 (s, 3H).

1- [5- (4-methoxy-phenyl) -thiophen-2-yl] -1 H-pyrazole: ¹ H-NMR (CDCl ₃ ): δ 7.64 (m, 2H), 7.37 (d, 2H) , 7.04 (d, 2H), 6.83 (d, 2H), 6.26 (t, 1H), 3.73 (s, 3H).

Example 579

1- [5- (2-OG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-OG1-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.65 (m, 2H), 7.30-7.49 (m, 11H), 7.14 (t, 1H), 7.03 (d, 2H), 6.85 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.42 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 580

1- [5- (3-OG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-OG1-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.30-7.49 (m, 10H), 7.22 (t, 1H), 7.03 (m, 4H), 6.73 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.26 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 581

1- [5- (4-OG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-OG1-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reaction of 1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.30-7.49 (m, 12H), 7.03 (d, 2H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.25 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 582

1- [5- (5-OG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-OG1-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reaction of 1- [5- (5-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.66 (m, 2H), 7.30-7.49 (m, 10H), 7.24 (t, 1H), 7.0 (m, 4H), 6.73 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.26 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 583

1- [5- (2-OG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-OG2-phenyl) -thiophen-2-yl] -1H-Pyrazole

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G2-Br and 18-crown-6 ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.67 (m, 2H), 7.29-7.43 (m, 21H), 7.1 (t, 1H), 7.0 (d, 2H), 6.84 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 584

1- [5- (3-OG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-OG2-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G2-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 7.05 (m, 4H), 6.73 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 585

1- [5- (4-OG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-OG2-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reaction of 1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G2-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 22H), 7.03 (d, 2H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 586

1- [5- (5-OG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-OG2-phenyl) -thiophen-2-yl] -1H-Pyrazole

Ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine by reaction of 1- [5- (5-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G2-Br and 18-crown-6 ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 20H), 7.24 (t, 1H), 7.0 (m, 4H), 6.73 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.22 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 587

1- [5- (2-OG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-OG3-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 41H), 7.13 (t, 1H), 7.04 (d, 2H), 6.84 (m, 2H), 6.65-6.52 (m, 22H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 588

1- [5- (3-OG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-OG3-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 40H), 7.22 (t, 1H), 7.0 (m, 4H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 589

1- [5- (4-OG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-OG3-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reaction of 1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 42H), 7.0 (d, 2H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 590

1- [5- (5-OG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-OG3-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (5-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G3-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 40H), 7.22 (t, 1H), 7.02 (m, 4H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 591

1- [5- (2-OG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-OG4-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (2-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 7.06 (d, 2H), 6.8 (m, 2H), 6.65-6.48 (m, 45H), 6.27 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 592

1- [5- (3-OG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-OG4-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (3-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 80H), 7.22 (t, 1H), 7.0 (m, 4H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.26 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 593

1- [5- (4-OG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-OG4-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (4-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 82H), 7.09 (d, 2H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 594

1- [5- (5-OG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-OG4-phenyl) -thiophen-2-yl] -1H-Pyrazole

Reactions of 1- [5- (5-Hydroxy-phenyl) -thiophen-2-yl] -1H-Pyrazole, G4-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R'-OR ) Through synthesis reaction. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 80H), 7.22 (t, 1H), 7.08 (m, 4H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.24 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

Example 595

1- [5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-MethyleneoxyG1-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.63 (m, 2H), 7.30-7.49 (m, 11H), 7.13 (m, 3H), 7.03 (d, 2H), 6.65 (d, 2H, J = 3.9) 6.55 (t, 1H, J = 2.1), 6.2 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 596

1- [5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-MethyleneoxyG1-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.30-7.49 (m, 12H), 7.21 (t, 1H), 7.0 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.22 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 597

1- [5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-MethyleneoxyG1-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole, G1-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 7.0 (d, 2H), 6.65 (d, 2H, J = 3.9) 6.55 (t, 1H, J = 2.1), 6.2 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 598

1- [5- (5-methyleneoxyG1-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-MethyleneoxyG1-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (5-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.30-7.49 (m, 12H), 7.23 (t, 1H), 7.03 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.21 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 599

1- [5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-MethyleneoxyG2-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.27-7.47 (m, 21H), 7.11 (m, 3H), 7.03 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.54 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.24 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 600

1- [5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-MethyleneoxyG2-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.27-7.47 (m, 22H), 7.23 (t, 1H), 7.04 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 601

1- [5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-MethyleneoxyG2-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 7.02 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 602

1- [5- (5-methyleneoxyG2-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-MethyleneoxyG2-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (5-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.27-7.47 (m, 22H), 7.22 (t, 1H), 7.03 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 603

1- [5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-MethyleneoxyG3-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.27-7.41 (m, 41H), 7.1 (m, 3H), 7.0 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 604

1- [5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-MethyleneoxyG3-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.27-7.41 (m, 42H), 7.2 (t, 1H), 7.0 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.21 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 605

1- [5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-MethyleneoxyG3-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 7.0 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 606

1- [5- (5-methyleneoxyG3-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-MethyleneoxyG3-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (5-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.27-7.41 (m, 42H), 7.23 (t, 1H), 7.0 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.21 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 607

1- [5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (2-MethyleneoxyG4-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (2-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.61 (m, 2H), 7.29-7.43 (m, 81H), 7.14 (m, 3H), 7.08 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 608

1- [5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (3-MethyleneoxyG4-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (3-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole, G4-OH was dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 82H), 7.21 (t, 1H), 7.03 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 609

1- [5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (4-MethyleneoxyG4-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (4-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.63 (m, 2H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 7.02 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 610

1- [5- (5-methyleneoxyG4-phenyl) -thiophen-2-yl] -1 H-pyrazole

1- [5- (5-MethyleneoxyG4-phenyl) -thiophen-2-yl] -1H-pyrazole

1- [5- (5-Bromomethyl-phenyl) -thiophen-2-yl] -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 44]

¹ H-NMR (CDCl ₃ ): δ 7.62 (m, 2H), 7.29-7.43 (m, 82H), 7.23 (t, 1H), 7.02 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 611

1- [7- (4-methoxy-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-Methoxy-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

The desired product was synthesized by C-C coupling reaction of 7- (4-Methoxy-phenyl) -9H-fluoren-2-boronic acid with 1-bromo-1H-pyrazole. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.92 (m, 2H), 7.84 (m, 2H), 7.72 (d, 1H), 7.61 (m, 2H), 7.43 (m, 3H), 6.83 (d, 2H ), 6.46 (t, 1 H), 3.93 (s, 2 H), 3.73 (s, 3 H).

Example 612

1- [7- (4-OG1-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-OG1-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

Reaction of 1- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R ' -OR) synthesized through the production reaction. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.91 (m, 2H), 7.81 (m, 2H), 7.72 (d, 1H), 7.65 (m, 2H), 7.30-7.49 (m, 13H), 6.65 (d , 2H, J = 3.9), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H), 3.93 (s , 2H).

Example 613

1- [7- (4-OG2-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-OG2-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

Reaction of 1- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole, G2-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R ' -OR) synthesized through the production reaction. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.91 (m, 2H), 7.82 (m, 2H), 7.72 (d, 1H), 7.6 (m, 2H), 7.29-7.43 (m, 23H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.83 (d, 2H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.9 (s, 2 H).

Example 614

1- [7- (4-OG3-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-OG3-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

Reaction of 1- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole, G3-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R ' -OR) synthesized through the production reaction. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.91 (m, 2H), 7.82 (m, 2H), 7.72 (d, 1H), 7.6 (m, 2H), 7.29-7.43 (m, 43H), 6.83 (d , 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.91 ( s, 2H).

Example 615

1- [7- (4-OG4-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-OG4-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

The reaction of 1- [7- (4-Hydroxy-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole, G4-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R ' -OR) synthesized through the production reaction. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.92 (m, 2H), 7.83 (m, 2H), 7.72 (d, 1H), 7.62 (m, 2H), 7.29-7.43 (m, 83H), 6.83 (d , 2H), 6.65-6.48 (m, 45H), 6.66 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 3.92 (s, 2 H).

Example 616

1- [7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-MethyleneoxyG1-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

1- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.92 (m, 2H), 7.82 (m, 2H), 7.72 (d, 1H), 7.6 (m, 2H), 7.30-7.49 (m, 13H), 7.11 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H), 3.92 (s, 2H).

Example 617

1- [7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-MethyleneoxyG2-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

1- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.91 (m, 2H), 7.83 (m, 2H), 7.72 (d, 1H), 7.62 (m, 2H), 7.27-7.47 (m, 23H), 7.13 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.93 (s, 2H).

Example 618

1- [7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-MethyleneoxyG3-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

1- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.92 (m, 2H), 7.82 (m, 2H), 7.72 (d, 1H), 7.62 (m, 2H), 7.27-7.41 (m, 43H), 7.12 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.93 (s, 2H).

Example 619

1- [7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl] -1H-pyrazole

1- [7- (4-MethyleneoxyG4-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole

1- [7- (4-Bromomethyl-phenyl) -9H-fluoren-2-yl] -1H-Pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 45]

¹ H-NMR (CDCl ₃ ): δ 7.92 (m, 2H), 7.83 (m, 2H), 7.72 (d, 1H), 7.6 (m, 2H), 7.29-7.43 (m, 83H), 7.13 (d , 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.93 (s, 2H).

Example 620

1- (6-methoxy-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-Methoxy-benzo [b] thiophen-2-yl) -1H-pyrazole

The desired product was synthesized by C-C coupling reaction of 6-Methoxy-benzo [b] thiophen-2-boronic acid with 1-bromo-1H-pyrazole. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.74 (m, 2H), 7.62 (d, 1H), 7.45 (s, 1H), 7.32 (s, 1H), 6.83 (d, 1H), 6.25 (t, 1H ), 3.73 (s, 3 H).

Example 621

1- (6-OG1-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-OG1-benzo [b] thiophen-2-yl) -1H-pyrazole

Reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -1H-pyrazole, G1-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.61 (d, 1H), 7.30-7.49 (m, 12H), 6.65 (d, 2H, J = 3.9), 6.8 (d, 1H) , 6.55 (t, 1H, J = 2.1), 6.22 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 622

1- (6-OG2-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-OG2-benzo [b] thiophen-2-yl) -1H-pyrazole

Reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -1H-pyrazole, G2-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.63 (d, 1H), 7.29-7.43 (m, 22H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.25 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 623

1- (6-OG3-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-OG3-benzo [b] thiophen-2-yl) -1H-pyrazole

Reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -1H-pyrazole, G3-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.61 (d, 1H), 7.29-7.43 (m, 42H), 6.8 (d, 1H), 6.65-6.52 (m, 22H), 6.22 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 624

1- (6-OG4-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-OG4-benzo [b] thiophen-2-yl) -1H-pyrazole

Reaction of 1- (6-Hydroxy-benzo [b] thiophen-2-yl) -1H-pyrazole, G4-Br and 18-crown-6 to produce ether (R'-OR) of hydroxy-aryl and bromo-alkylpyridine Synthesis via reaction. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 6.82 (d, 1H), 6.65-6.48 (m, 45H), 6.22 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 625

1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-MethyleneoxyG1-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-Bromomethyl-benzo [b] thiophen-2-yl) -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.63 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (d, 1H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.24 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 626

1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-MethyleneoxyG2-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-Bromomethyl-benzo [b] thiophen-2-yl) -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.71 (m, 2H), 7.63 (m, 2H), 7.27-7.47 (m, 21H), 7.1 (d, 1H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.21 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 627

1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-MethyleneoxyG3-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-Bromomethyl-benzo [b] thiophen-2-yl) -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.63 (m, 2H), 7.27-7.41 (m, 41H), 7.13 (d, 1H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 628

1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-MethyleneoxyG4-benzo [b] thiophen-2-yl) -1H-pyrazole

1- (6-Bromomethyl-benzo [b] thiophen-2-yl) -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 46]

¹ H-NMR (CDCl ₃ ): δ 7.72 (m, 2H), 7.63 (m, 2H), 7.29-7.43 (m, 81H), 7.21 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 629

1- (4-methoxy-naphthalein-1-yl) -1H-pyrazole

1- (4-Methoxy-naphthalen-1-yl) -1H-pyrazole

The desired product was synthesized by C-C coupling reaction of 4-Methoxy-naphthalen-1-boronic acid with 1-bromo-1H-pyrazole. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.4 (t, 1H), 7.3 (t, 1H), 7.22 (d, 1H ), 6.65 (d, 1 H), 6.46 (t, 1 H), 3.73 (s, 3 H).

Example 630

1- (4-OG1-naphthalein-1-yl) -1H-pyrazole

1- (4-OG1-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (4-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G1-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.30-7.49 (m, 12H), 7.22 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.62 (d, 1H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 631

1- (4-OG2-naphthalein-1-yl) -1H-pyrazole

1- (4-OG2-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (4-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G2-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.29-7.43 (m, 22H), 7.2 (t, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.62 (d, 1H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 632

1- (4-OG3-naphthalein-1-yl) -1H-pyrazole

1- (4-OG3-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (4-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G3-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.29-7.43 (m, 42H), 7.22 (t, 1H), 6.6 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 633

1- (4-OG4-naphthalein-1-yl) -1H-pyrazole

1- (4-OG4-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (4-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G4-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (m, 2H), 7.29-7.43 (m, 82H), 7.22 (t, 1H), 6.61 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 634

1- (4-methyleneoxyG1-naphthalein-1-yl) -1H-pyrazole

1- (4-MethyleneoxyG1-naphthalen-1-yl) -1H-pyrazole

1- (4-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 7.6 (d, 1H) 7.30-7.49 (m, 12H), 7.22 (t, 1H), 7.11 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 635

1- (4-methyleneoxyG2-naphthalein-1-yl) -1H-pyrazole

1- (4-MethyleneoxyG2-naphthalen-1-yl) -1H-pyrazole

1- (4-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.6 (d, 1H), 7.27-7.47 (m, 22H), 7.23 (t , 1H), 7.12 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 636

1- (4-methyleneoxyG3-naphthalein-1-yl) -1H-pyrazole

1- (4-MethyleneoxyG3-naphthalen-1-yl) -1H-pyrazole

1- (4-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.80 (d, 1H), 7.72 (d, 1H), 7.62 (d, 1H), 7.27-7.41 (m, 42H), 7.23 (t , 1H), 7.11 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 637

1- (4-methyleneoxyG4-naphthalein-1-yl) -1H-pyrazole

1- (4-MethyleneoxyG4-naphthalen-1-yl) -1H-pyrazole

1- (4-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 47]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.22 (t , 1H), 7.12 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

Example 638

1- (5-methoxy-naphthalein-1-yl) -1H-pyrazole

1- (5-Methoxy-naphthalen-1-yl) -1H-pyrazole

The desired product was synthesized by C-C coupling reaction of 5-Methoxy-naphthalen-1-boronic acid with 1-bromo-1H-pyrazole. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (d, 1H), 7.41 (d, 1H), 7.33 (m, 2H), 7.23 (t, 1H ), 6.64 (d, 1 H), 6.46 (t, 1 H), 3.73 (s, 3 H).

Example 639

1- (5-OG1-naphthalein-1-yl) -1H-pyrazole

1- (5-OG1-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (5-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G1-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 13H), 7.22 (t, 1H), 6.65 (d , 2H, J = 3.9), 6.6 (d, 1H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 640

1- (5-OG2-naphthalein-1-yl) -1H-pyrazole

1- (5-OG2-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (5-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G2-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 23H), 7.22 (t, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.6 (d, 1H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

Example 641

1- (5-OG3-naphthalein-1-yl) -1H-pyrazole

1- (5-OG3-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (5-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G3-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 43H), 7.22 (t, 1H), 6.62 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 642

1- (5-OG4-naphthalein-1-yl) -1H-pyrazole

1- (5-OG4-naphthalen-1-yl) -1H-pyrazole

Synthesis of 1- (5-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G4-Br and 18-crown-6 by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine It was. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 8.22 (d, 1H), 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 83H), 7.21 (t, 1H), 6.63 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 643

1- (5-methyleneoxyG1-naphthalein-1-yl) -1H-pyrazole

1- (5-MethyleneoxyG1-naphthalen-1-yl) -1H-pyrazole

1- (5-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 13H), 7.22 (t, 1H), 7.13 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

Example 644

1- (5-methyleneoxyG2-naphthalein-1-yl) -1H-pyrazole

1- (5-MethyleneoxyG2-naphthalen-1-yl) -1H-pyrazole

1- (5-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 23H), 7.21 (t, 1H), 7.13 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 645

1- (5-methyleneoxyG3-naphthalein-1-yl) -1H-pyrazole

1- (5-MethyleneoxyG3-naphthalen-1-yl) -1H-pyrazole

1- (5-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 43H), 7.22 (t, 1H), 7.12 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 646

1- (5-methyleneoxyG4-naphthalein-1-yl) -1H-pyrazole

1- (5-MethyleneoxyG4-naphthalen-1-yl) -1H-pyrazole

1- (5-Bromomethyl-naphthalen-1-yl) -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Legal 48]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 83H), 7.25 (t, 1H), 7.12 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 647

1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazole

The desired product was synthesized by C-C coupling reaction of 2,3,6-Trifluoro-4'-methoxy-biphenyl-4-boronic acid with 1-bromo-1H-pyrazole. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.37 (d, 2H), 6.83 (m, 3H), 6.46 (t, 1H), 3.73 (s, 3H ).

Example 648

1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazole

The reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -1H-pyrazole, G1-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 12H), 6.83 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

Example 649

1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-OG2-biphenyl-4-yl) -1H-pyrazole

The reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -1H-pyrazole, G2-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 22H), 6.83 (m, 3H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

Example 650

1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-OG3-biphenyl-4-yl) -1H-pyrazole

The reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -1H-pyrazole, G3-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 42H), 6.83 (m, 3H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

Example 651

1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-OG4-biphenyl-4-yl) -1H-pyrazole

The reaction of 1- (2,3,6-Trifluoro-4'-hydroxy-biphenyl-4-yl) -1H-pyrazole, G4-Br and 18-crown-6 with ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) was synthesized through the production reaction. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 82H), 6.83 (m, 3H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

Example 652

1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -1H-pyrazole and G1-OH were dissolved in acetone and synthesized by adding KOH. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

Example 653

1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -1H-pyrazole and G2-OH were dissolved in acetone and synthesized by adding KOH. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

Example 654

1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -1H-pyrazole and G3-OH were dissolved in acetone and synthesized by adding KOH. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.52 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 655

1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -1H-pyrazole

1- (2,3,6-Trifluoro-4'-bromomethyl-biphenyl-4-yl) -1H-pyrazole and G4-OH were dissolved in acetone and synthesized by adding KOH. [Legal 49]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

Example 656

1- (5-OG1-naphthalen-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-OG1-naphthalen-1-yl] -4- (H, F or CH ₃ ) -isoquinoline

Reaction of 1- (5-Hydroxy-naphthalen-1-yl] -4- (H, F or CH ₃ ) -isoquinoline with G1-Br and 18-crown-6 ethers of hydroxy-aryl and bromo-alkylpyridine (R '-OR) synthesis via synthesis [ligand 18].

1- (5-OG1-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ ): δ 8.33 (s, 1H), 8.23 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H), 7.29-7.44 (m, 12H), 6.75 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H) .

Example 657

1- (5-methyleneoxyG1-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolin

1- (5-MethyleneoxyG1-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline

1- (5-Bromomethyl-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinoline and G1-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 17]

1- (5-methyleneoxyG1-naphthalen-1-yl) -4-methyl-isocurolin: ¹ H-NMR (CDCl ₃ )

δ 8.33 (s, 1H), 8.22 (d, 1H), 8.02 (d, 1H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.53 (t, 1H) , 7.30-7.49 (m, 12H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3 H).

Example 658

5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-boronic acid and 5-bromo-2

The desired product was synthesized by C-C coupling reaction of -phenylpyridine. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.92 (d, 2H), 7.73 (d, 1H), 7.62 (m, 4H), 7.37 (m, 6H), 7.28 (t, 1H ), 6.83 (d, 4H), 3.73 (s, 6H).

Example 659

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenylpyridine

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

By reaction of 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine, G1-Br and 18-crown-6 The synthesis of hydroxy-aryl and bromo-alkylpyridine by ether (R'-OR) production was performed. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.92 (d, 2H), 7.73 (d, 1H), 7.61 (m, 4H), 7.30-7.49 (m, 26H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 660

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

By reaction of 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine, G2-Br and 18-crown-6 The synthesis of hydroxy-aryl and bromo-alkylpyridine by ether (R'-OR) production was performed. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.84 (s, 1H), 7.92 (d, 2H), 7.73 (d, 1H), 7.61 (m, 4H), 7.29-7.43 (m, 46H), 7.28 (t , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

Example 661

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine, G3-Br and 18-crown-6 The synthesis of hydroxy-aryl and bromo-alkylpyridine by ether (R'-OR) production was performed. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.6 (m, 4H), 7.29-7.43 (m, 86H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 662

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

By reaction of 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine, G4-Br and 18-crown-6 The synthesis of hydroxy-aryl and bromo-alkylpyridine by ether (R'-OR) production was performed. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.92 (d, 2H), 7.71 (d, 1H), 7.62 (m, 4H), 7.29-7.43 (m, 166H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 663

5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dihydroxymethyl- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine and G1-OH dissolved in acetone and synthesized by adding KOH It was. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.91 (d, 2H), 7.73 (d, 1H), 7.61 (m, 4H), 7.30-7.49 (m, 26H), 7.28 (t , 1H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

Example 664

5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dihydroxymethyl- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine and G2-OH dissolved in acetone and synthesized by adding KOH It was. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.92 (d, 2H), 7.71 (d, 1H), 7.61 (m, 4H), 7.27-7.47 (m, 46H), 7.28 (t , 1H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.51 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 665

5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dihydroxymethyl- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine and G3-OH dissolved in acetone and synthesized by adding KOH It was. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.61 (m, 4H), 7.27-7.41 (m, 86H), 7.28 (t , 1H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.51 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 666

5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine

5- (4,4 ''-Dihydroxymethyl- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridine and G4-OH dissolved in acetone and synthesized by adding KOH It was. [Ligand 10]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.92 (d, 2H), 7.71 (d, 1H), 7.62 (m, 4H), 7.29-7.43 (m, 166H), 7.28 (t , 1H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 667

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-pyridine

By CC coupling reaction of 2-Bromo-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine with thiophen-2-boronic acid The desired product was synthesized. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.01 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H), 7.37 (d, 4H), 7.22 (d, 1H ), 7.02 (m, 2H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 668

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine, G1-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 24H), 7.22 (d , 1H), 7.02 (m, 2H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

Example 669

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine, G2-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.01 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 44H), 7.22 (d , 1H), 7.03 (m, 2H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

Example 670

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine, G3-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H), 7.29-7.43 (m, 84H), 7.22 (d , 1H), 7.0 (m, 2H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

Example 671

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine, G4-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.02 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 164H), 7.23 (d , 1H), 7.02 (m, 2H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95- 4.92 (m, 56 H).

Example 672

5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-DibromoG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine and G1-OH in acetone It was dissolved and synthesized by adding KOH. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.71 (d, 1H), 7.61 (m, 3H), 7.30-7.49 (m, 24H), 7.21 (d , 1H), 7.12 (d, 4H), 7.0 (m, 2H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

d

Example 673

5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-DibromoG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine and G2-OH in acetone It was dissolved and synthesized by adding KOH. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.03 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H), 7.27-7.47 (m, 44H), 7.22 (d , 1H), 7.12 (d, 4H), 7.02 (m, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 674

5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-DibromoG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine and G3-OH in acetone It was dissolved and synthesized by adding KOH. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.01 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.27-7.41 (m, 84H), 7.22 (d , 1H), 7.12 (d, 4H), 7.0 (m, 2H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.5 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 675

5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl -pyridine

5- (4,4 ''-DibromoG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridine and G4-OH in acetone It was dissolved and synthesized by adding KOH. [Ligand 52]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 164H), 7.22 (d , 1H), 7.12 (d, 4H), 7.03 (m, 2H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 676

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

CC coupling reaction of 2-Bromo-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine with 9H-fluoren-2-boronic acid The desired product was synthesized by [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.61 (m, 4H), 7.55 (d, 1H), 7.37 (m, 5H), 7.28 (t, 1H), 6.83 (d, 4H), 3.87 (s, 2H), 3.73 (s, 6H) .

Example 677

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine, G1-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.71 (d, 1H ), 7.61 (m, 4H), 7.55 (d, 1H), 7.30-7.49 (m, 26H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H), 3.87 (s, 2H).

Example 678

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine, G2-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.74 (d, 1H ), 7.63 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 46H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J) = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H), 3.87 (s, 2H).

Example 679

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine, G3-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 86H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 ( s, 32H), 4.99 (s, 16H), 4.93 (s, 8H), 3.87 (s, 2H).

Example 680

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine, G4-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.71 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 166H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 ( s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H), 3.87 (s, 2H).

Example 681

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine and G1-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.73 (d, 1H ), 7.61 (m, 4H), 7.55 (d, 1H), 7.30-7.49 (m, 26H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H), 3.87 (s, 2H).

Example 682

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine and G2-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.73 (d, 1H ), 7.65 (m, 4H), 7.55 (d, 1H), 7.27-7.47 (m, 47H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s , 4H), 3.87 (s, 2H).

Example 683

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine and G3-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.27-7.41 (m, 87H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J) = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d , 4H), 3.87 (s, 2H).

Example 684

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridine and G4-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 54]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.28 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.63 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 167H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H) , J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H), 3.87 (s, 2H).

Example 685

2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

CC of 2-Bromo-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and benzo [b] thiophen-2-boronic acid The desired product was synthesized by the coupling reaction. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.05 (d, 1H), 7.91 (d, 1H), 7.82 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H ), 7.32 (m, 7H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 686

2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine, G1-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.01 (d, 1H), 7.91 (d, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H ), 7.30-7.49 (m, 27H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

Example 687

2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine, G2-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H ), 7.29-7.43 (m, 47H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

Example 688

2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine, G3-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.83 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H ), 7.29-7.43 (m, 87H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

Example 689

2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine, G4-Br and The reaction of 18-crown-6 was carried out through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.03 (d, 1H), 7.92 (d, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 7.63 (m, 3H ), 7.29-7.43 (m, 167H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95- 4.92 (m, 56 H).

Example 690

2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dibromo- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and G1-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.01 (d, 1H), 7.93 (d, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H ), 7.30-7.49 (m, 27H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

Example 691

2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dibromo- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and G2-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.81 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H ), 7.27-7.47 (m, 47H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 692

2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dibromo- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and G3-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.91 (s, 1H), 8.03 (d, 1H), 7.92 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.63 (m, 3H ), 7.27-7.41 (m, 87H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.5 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 693

2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine

2-Benzo [b] thiophen-2-yl-5- (4,4 ''-dibromo- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and G4-OH It was dissolved in acetone and synthesized by adding KOH. [Ligand 55]

¹ H-NMR (CDCl ₃ ): δ 8.92 (s, 1H), 8.02 (d, 1H), 7.91 (d, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H ), 7.29-7.43 (m, 167H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 694

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

By CC coupling reaction of 2-Bromo-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine with naphthalen-1-boronic acid The desired product was synthesized. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.13 (d, 1H), 7.72 (m, 4H), 7.61 (m, 4H), 7.41 (t, 1H), 7.37 (d, 4H ), 7.33 (m, 2H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 695

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine, G1-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.12 (d, 1H), 7.73 (m, 4H), 7.61 (m, 4H), 7.30-7.49 (m, 27H), 6.83 (d , 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 696

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine, G2-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.11 (d, 1H), 7.71 (m, 4H), 7.63 (m, 4H), 7.29-7.43 (m, 47H), 6.83 (d , 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8 H).

Example 697

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine, G3-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.11 (d, 1H), 7.72 (m, 4H), 7.61 (m, 4H), 7.29-7.43 (m, 87H), 6.83 (d , 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 698

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine, G4-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.11 (d, 1H), 7.72 (m, 4H), 7.61 (m, 4H), 7.29-7.43 (m, 167H), 6.83 (d , 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 699

5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

Dissolve 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine and G1-OH in acetone Was synthesized by addition. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.21 (d, 1H), 7.72 (m, 4H), 7.61 (m, 4H), 7.30-7.49 (m, 27H), 7.12 (d , 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

Example 700

5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

Dissolve 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine and G2-OH in acetone Was synthesized by addition. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.11 (d, 1H), 7.71 (m, 4H), 7.62 (m, 4H), 7.27-7.47 (m, 47H), 7.12 (d , 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.51 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 701

5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

Dissolve 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine and G3-OH in acetone Was synthesized by addition. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 8.11 (d, 1H), 7.72 (m, 4H), 7.62 (m, 4H), 7.27-7.41 (m, 87H), 7.12 (d , 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 ( s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 702

5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridine

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine

Dissolve 5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridine and G4-OH in acetone Was synthesized by addition. [Ligand 56]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 8.12 (d, 1H), 7.71 (m, 4H), 7.61 (m, 4H), 7.29-7.43 (m, 167H), 7.12 (d , 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 703

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl)- Pyridine

5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

2-Bromo-5- (4,4 ''-Dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridine and 2,3,5-trifluro-1-boronic acid The desired product was synthesized by the CC coupling reaction. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.72 (d, 1H), 7.62 (m, 4H), 7.45 (s, 1H), 7.37 (d, 4H), 6.83 (d, 4H ), 6.68 (s, 1 H) 3.73 (s, 6 H).

Example 704

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) Pyridine

5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine, G1- The reaction of Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.83 (s, 1H), 7.72 (d, 1H), 7.6 (m, 4H), 7.30-7.49 (m, 25H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 705

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) Pyridine

5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro -phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine, G2- The reaction of Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. Ligand 57

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.71 (d, 1H), 7.63 (m, 4H), 7.29-7.43 (m, 45H), 6.83 (d, 4H), 6.68 (s , 1H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8 H).

Example 706

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) Pyridine

5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine, G3- The reaction of Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.71 (d, 1H), 7.61 (m, 4H), 7.29-7.43 (m, 85H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 707

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) Pyridine

5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine, G4- The reaction of Br and 18-crown-6 was synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.72 (d, 1H), 7.65 (m, 4H), 7.29-7.43 (m, 165H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 708

5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl ) -Pyridine

5- (4,4 ''-DimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine and G1- OH was dissolved in acetone and synthesized by adding KOH. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.72 (d, 1H), 7.63 (m, 4H), 7.30-7.49 (m, 25H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

Example 709

5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl ) -Pyridine

5- (4,4 ''-DimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine and G2- OH was dissolved in acetone and synthesized by adding KOH. Ligand 57

¹ H-NMR (CDCl ₃ ): δ 8.82 (s, 1H), 7.71 (d, 1H), 7.62 (m, 4H), 7.27-7.47 (m, 45H), 6.83 (d, 4H), 6.68 (s , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.52 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 710

5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl ) -Pyridine

5- (4,4 ''-DimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine and G3- OH was dissolved in acetone and synthesized by adding KOH. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.72 (d, 1H), 7.62 (m, 4H), 7.27-7.41 (m, 85H), 6.83 (d, 4H), 6.68 (s , 1H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.51 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 ( s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 711

5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl ) -Pyridine

5- (4,4 ''-DimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine

5- (4,4 ''-Dihydroxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine and G4- OH was dissolved in acetone and synthesized by adding KOH. [Rigand 57]

¹ H-NMR (CDCl ₃ ): δ 8.81 (s, 1H), 7.72 (d, 1H), 7.61 (m, 4H), 7.29-7.43 (m, 168H), 6.83 (d, 4H), 6.68 (s , 1H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 712

4 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Desired by CC coupling reaction of 4 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) benzene-3'-boronic acid and 2-bromopyridine The product was synthesized. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.47 (t, 1H ), 7.41 (t, 1H), 7.37 (d, 4H), 6.98 (t, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 713

4 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Reaction of 4 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine, G1-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 28H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 714

4 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Reaction of 4 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine, G2-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.6 (m, 3H), 7.29-7.43 (m, 48H), 6.98 (t , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

Example 715

4 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Reaction of 4 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine, G3-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.63 (m, 3H), 7.29-7.43 (m, 88H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 716

4 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Reaction of 4 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine, G4-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.6 (m, 3H), 7.29-7.43 (m, 168H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 717

4 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-DimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Dissolve 4 '-(4,4' '-Dimethylbromo- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine and G1-OH in acetone and add KOH Synthesized. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.6 (m, 3H), 7.30-7.49 (m, 28H), 7.12 (d , 4H), 6.98 (t, 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

Example 718

4 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-DimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Dissolve 4 '-(4,4' '-Dimethylbromo- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine and G2-OH in acetone and add KOH Synthesized. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.27-7.47 (m, 48H), 7.12 (d , 4H), 6.98 (t, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 719

4 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-DimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Dissolve 4 '-(4,4' '-Dimethylbromo- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine and G3-OH in acetone and add KOH Synthesized. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.6 (m, 3H), 7.27-7.41 (m, 88H), 7.12 (d , 4H), 6.98 (t, 1H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 720

4 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridine

4 '-(4,4' '-DimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine

Dissolve 4 '-(4,4' '-Dimethylbromo- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridine and G4-OH in acetone and add KOH Synthesized. [Ligand 51]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.6 (m, 3H), 7.29-7.43 (m, 168H), 7.12 (d , 4H), 6.98 (t, 1H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 721

1- [3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

CC coupling of 5 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) benzene-3'-boronic acid with 1-bromo-4-isoquinoline The desired product was synthesized by the reaction. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.91 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.51 (m, 2H), 7.42 (t, 1H), 7.37 (d, 4H), 7.12 (d, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 722

1- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Reaction of 1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline, G1-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.9 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.30-7.49 (m, 27H), 7.13 (d, 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s , 4H), 5.03 (s, 8H).

Example 723

1- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Reaction of 1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline, G2-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.91 (d, 1H), 7.72 (d, 1H), 7.65 (m, 4H ), 7.29-7.43 (m, 47H), 7.16 (d, 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

Example 724

1- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Reaction of 1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline, G3-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.91 (d, 1H), 7.72 (d, 1H), 7.62 (m, 4H ), 7.29-7.43 (m, 87H), 7.12 (d, 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 ( s, 16 H), 4.93 (s, 8 H).

Example 725

1- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Reaction of 1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline, G4-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.93 (d, 1H), 7.76 (d, 1H), 7.62 (m, 4H ), 7.29-7.43 (m, 167H), 7.1 (d, 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 ( s, 32H), 4.95-4.92 (m, 56H).

Example 726

1- [3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-DimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Dissolve 1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline and G1-OH in acetone and add KOH Synthesized. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.30-7.49 (m, 27H), 7.12 (m, 5H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

Example 727

1- [3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-DimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Dissolve 1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline and G2-OH in acetone and add KOH Synthesized. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.52 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.93 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.27-7.47 (m, 47H), 7.12 (m, 5H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 728

1- [3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-DimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Dissolve 1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline and G3-OH in acetone and add KOH Synthesized. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.54 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.93 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.27-7.41 (m, 87H), 7.12 (m, 5H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.5 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 729

1- [3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] isocurolin

1- [3 '-(4,4' '-DimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline

Dissolve 1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] isoquinoline and G4-OH in acetone and add KOH Synthesized. [Ligand 20]

¹ H-NMR (CDCl ₃ ): δ 8.53 (d, 1H), 8.21 (s, 1H), 7.95 (d, 1H), 7.94 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.29-7.43 (m, 165H), 7.12 (m, 5H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 730

6- [5 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

CC coupling reaction of 5 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) benzene-3'-boronic acid with 6-bromo-phenanthridine The desired product was synthesized by this. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.12 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.72 (d, 1H), 7.6 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.5 (t, 1H), 7.4 (m, 2H), 7.37 (d, 4H), 6.83 (d, 4H), 3.73 (s, 6H) .

Example 731

6- [5 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine, of G1-Br and 18-crown-6 Reactions were synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.62 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.30-7.49 (m, 27H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J) = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 732

6- [5 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine, of G2-Br and 18-crown-6 Reactions were synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 47H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J) = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

Example 733

6- [5 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine, of G3-Br and 18-crown-6 Reactions were synthesized through ether (R'-OR) production of hydroxy-aryl and bromo-alkylpyridine. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.62 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 87H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 ( s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 734

6- [5 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] of phenanthridine, G3-Br and 18-crown-6 Reactions were synthesized through ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.14 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.7 (d, 1H), 7.63 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 167H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 ( s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 735

6- [5 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-DimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] Dissolve phenanthridine and G1-OH in acetone and add KOH Synthesized. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.14 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.71 (d, 1H), 7.64 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.30-7.49 (m, 27H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J) = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

Example 736

6- [5 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-DimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine and G2-OH dissolved in acetone and KOH added Synthesized. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.27-7.47 (m, 47H), 6.83 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s , 4H).

Example 737

6- [5 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-DimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine and G3-OH dissolved in acetone and KOH added Synthesized. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.7 (d, 1H), 7.62 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.27-7.41 (m, 87H), 6.83 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J) = 2.4), 6.5 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d , 4H).

Example 738

6- [5 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl] phenanthridine

6- [5 '-(4,4' '-DimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine

Dissolve 6- [5 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl] phenanthridine and G4-OH in acetone and add KOH Synthesized. [Ligand 30]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.11 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.7 (d, 1H), 7.65 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 165H), 6.83 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H) , J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 739

2- [3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

CC coupling reaction of 5 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) benzene-3'-boronic acid with 2-bromo-benzothiazole The desired product was synthesized by this. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.7 (s, 1H), 7.62 (m, 3H), 7.55 (m, 2H), 7.41 (m, 2H ), 7.37 (m, 5H), 6.83 (d, 4H), 3.73 (s, 6H).

Example 740

2- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

Reaction of 2- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole, G1-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (s, 1H), 7.61 (m, 3H), 7.55 (m, 2H), 7.30-7.49 (m , 27H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

Example 741

2- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

Reaction of 2- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole, G2-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (s, 1H), 7.61 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m , 47H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

Example 742

2- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

Reaction of 2- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole, G3-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (s, 1H), 7.62 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m 87H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

Example 743

2- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl]) benzothiazole

2- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

Reaction of 2- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole, G4-Br and 18-crown-6 It was synthesized by ether (R'-OR) formation of hydroxy-aryl and bromo-alkylpyridine. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (s, 1H), 7.61 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m 167H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

Example 744

2- [3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-DimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole and G1-OH are dissolved in acetone and KOH is added Synthesized. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (s, 1H), 7.62 (m, 3H), 7.55 (m, 2H), 7.30-7.49 (m , 27H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

Example 745

2- [3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-DimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole and G2-OH are dissolved in acetone and KOH is added Synthesized. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.72 (s, 1H), 7.62 (m, 3H), 7.55 (m, 2H), 7.27-7.47 (m , 47H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 746

2- [3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-DimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole and G3-OH are dissolved in acetone and KOH is added Synthesized. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (s, 1H), 7.61 (m, 3H), 7.55 (m, 2H), 7.27-7.41 (m , 87H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 6.51 (t, 8H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 747

2- [3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-DimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

2- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] benzothiazole

6- (5- (3,5-Di (4-bromomethylphenyl) phenyl) phenyl) phenanthridine and G4-OH were dissolved in acetone and synthesized by adding KOH. [Ligand 40]

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.73 (s, 1H), 7.61 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m , 165H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 748

1- [3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

CC coupling of 5 '-(4,4' '-Dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) benzene-3'-boronic acid with 1-bromo-1H-pyrazole The desired product was synthesized by the reaction. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.6 (m, 3H), 7.5 (m, 2H), 7.37 (d, 4H), 7.31 (t, 1H ), 7.22 (d, 1H), 6.83 (d, 4H), 6.46 (t, 1H), 3.73 (s, 6H).

Example 749

1- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole, G1-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.53 (m, 2H), 7.30-7.49 (m, 25H), 7.2 (d , 1H), 6.83 (d, 4H), 6.46 (t, 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

Example 750

1- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole, G2-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.29-7.43 (m, 45H), 7.22 (d , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 6.46 (t, 1H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

Example 751

1- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole, G3-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.29-7.43 (m, 85H), 7.23 (d , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 6.46 (t, 1H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

Example 752

1- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dihydroxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole, G4-Br and 18-crown- In the reaction of 6, hydroxy-aryl and bromo-alkylpyridine were synthesized through ether (R'-OR) reaction. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.5 (m, 2H), 7.29-7.43 (m, 165H), 7.24 (d , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 6.46 (t, 1H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95- 4.92 (m, 56 H).

Example 753

1- [3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-DimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole and G1-OH in acetone and KOH Was synthesized by addition. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.30-7.49 (m, 25H), 7.12 (d , 4H), 7.2 (d, 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

Example 754

1- [3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-DimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole and G2-OH are dissolved in acetone and KOH Was synthesized by addition. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.61 (m, 3H), 7.54 (m, 2H), 7.27-7.47 (m, 45H), 7.23 (d , 1H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

Example 755

1- [3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-DimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole and G3-OH in acetone Was synthesized by addition. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.27-7.41 (m, 85H), 7.24 (d , 1H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 756

1- [3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-DimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole

1- [3 '-(4,4' '-Dibromomethyl- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl] -1H-pyrazole and G4-OH are dissolved in acetone and KOH Was synthesized by addition. [Ligand 50]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.51 (m, 2H), 7.29-7.43 (m, 165H), 7.22 (d , 1H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

Example 757

Tris [2- (3-methoxy-phenyl) pyridineeto] iridium (III)

Tris [2- (3-methoxy-phenyl) pyridinato] iridium (III)

In a nitrogen atmosphere, ligand (1.0 g), Ir (acac) ₃ (0.156 g) and glycerol (15 mL) are placed in a three neck flask and the mixture is reacted at 220 ^° C. for 48 hours and cooled to room temperature. 200 mL of water is added to the product and extracted three times with 100 mL of dichloromethane. The organic layer collected in one place was dried over anhydrous magnesium sulfate, and the solvent was removed to obtain an oil. The purification was separated by column chromatography. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 9.58 (s, 1 H), 8.62 (m, 1 H), 7.82-7.88 (m, 2 H), 7.44-7.52 (m, 2H), 7.38 (t, 1 H, J = 7.8), 7.22-7.32 (m, 2H), 6.82 (m, 1H), 3.4 (S, 3H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 758

Tris [2- (2-OG1-phenyl) pyridineeto] iridium (III)

Tris [2- (2-OG1-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 7.88 (d, 2H, J = 1.2 Hz), 7.66 (t, 1H, J = 1.2), 7.67-7.74 (m, 2H), 7.30 -7.49 (m, 11H), 7.20-7.25 (m, 1H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H). EI (m / z): 898 (M ⁺ ).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 759

Tris [2- (3-OG1-phenyl) pyridineeto] iridium (III)

Tris [2- (3-OG1-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.55-7.75 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.19-7.34 (m, 11H), 7.00 (m, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 760

Tris [2- (4-OG1-phenyl) pyridineeto] iridium (III)

Tris [2- (4-OG1-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.47 (t, 1H) 7.19-7.34 (m, 10H), 7.20-7.25 (m, 1H), 7.02 ( m, 1H), 6.98 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.86 (d, 1H), 6.57 (t, 1H, J = 2.4 ), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 761

Tris [2- (2-OG2-phenyl) pyridineeto] iridium (III)

Tris [2- (2-OG2-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (tt, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.19-7.33 (m, 21H), 7.02 (d , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 762

Tris [2- (3-OG2-phenyl) pyridineeto] iridium (III)

Tris [2- (3-OG2-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (tt, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.19-7.33 (m, 21H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 763

Tris [2- (4-OG2-phenyl) pyridineeto] iridium (III)

Tris [2- (4-OG2-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex.

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.47 (t, 1H), 7.20-7.34 (m, 21H), 7.02 (t, 1H), 6.92 (d , 1H), 6.85 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 764

Tris [2- (2-OG3-phenyl) pyridineeto] iridium (III)

Tris [2- (2-OG3-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (tt, 1H), 7.67 (d, 2H), 7.47 (t, 1H), 7.19-7.34 (m, 41H), 7.02 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 765

Tris [2- (3-OG3-phenyl) pyridineeto] iridium (III)

Tris [2- (3-OG3-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (t, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.56 (d, 1H, J = 7.8), 7.20-7.33 (m, 41H), 7.02 (m, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 766

Tris [2- (4-OG3-phenyl) pyridineeto] iridium (III)

Tris [2- (4-OG3-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.56 (d, 1H), 7.20-7.36 (m, 40H), 7.02 (t, 1H), 6.92 (t , 1H), 6.85 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 767

Tris [2- (2-OG4-phenyl) pyridineeto] iridium (III)

Tris [2- (2-OG4-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.56 (d, 1H), 7.47 (t, 1H), 7.20-7.37 (m, 81H), 7.02 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 768

Tris [2- (3-OG4-phenyl) pyridineeto] iridium (III)

Tris [2- (3-OG4-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (tt, 1H, J = 1.2), 7.67-7.74 (m, 4H), 7.20-7.36 (m, 81H), 7.02 (m, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 769

Tris [2- (4-OG4-phenyl) pyridineeto] iridium (III)

Tris [2- (4-OG4-phenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.74 (d, 1H), 7.47 (t, 1H), 7.20-7.37 (m, 81H), 7.02 (t, 1H), 6.92 (t , 1H), 6.85 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 770

Tris [2- (2-G1-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (2-G1-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 7.88 (d, 2H, J = 1.2 Hz), 7.67-7.74 (m, 3H), 7.48 (d, 1H, J = 7.8), 7.20 -7.39 (m, 12H), 7.02 (m, 1H), 6.71 (d, 2H, J = 2.1), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H) , 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 771

Tris [2- (3-G1-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (3-G1-oxymethylenephenyl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

1 H-NMR (CDCl 3): δ 8.66 (t, 1H, J = 1.2), 8.00 (s, 1H), 7.90-7.92 (m, 1H), 7.70-7.72 (m, 2H), 7.20-7.39 (m, 13H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 772

Tris [2- (4-G1-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (4-G1-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.20-7.39 (m, 12H), 7.02 (m, 1H), 6.98 (t, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 773

Tris [2- (2-G2-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (2-G2-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.47 (t, 1H), 7.17-7.37 (m, 21H), 7.02 (m, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.54 (t, 2H, J = 2.4), 6.51 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 774

Tris [2- (3-G2-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (3-G2-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 1H), 7.17-7.37 ( m, 21H), 7.13-7.20 (m, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t , 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 775

Tris [2- (4-G2-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (4-G2-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.69 (d, 1H), 7.88 (d, 1H), 7.47 (t, 1H), 7.12 (d, 4H), 7.17-7.39 (m, 22H), 7.02 (m , 1H), 6.98 (t, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 776

Tris [2- (2-G3-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (2-G3-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.47 (t, 1H), 7.17-7.31 (m, 41H), 7.08 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 777

Tris [2- (3-G3-oxymethylenephenyl) pyridineeto] iridium (III)

Trsi [2- (3-G3-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 2H), 7.17-7.31 ( m, 43H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 778

Tris [2- (4-G3-oxymethylenephenyl) pyridineeto] iridium (III)

Trsi [2- (4-G3-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.17-7.31 (m, 42H), 7.02 (m, 1H ), 6.98 (t, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 779

Tris [2- (2-G4-oxymethylenephenyl) pyridineeto] iridium (III)

Trsi [2- (2-G4-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.68 (t, 1H), 7.67 (d, 2H), 7.47 (t, 1H), 7.19-7.33 (m, 81H), 7.02 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 780

Tris [2- (3-G4-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (3-G4-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): δ 8.66 (d, 1H, J = 4.2), 8.00 (s, 1H), 7.91-7.89 (m, 1H), 7.69-7.67 (m, 1H), 7.20-7.33 ( m, 80H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2 H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 781

Tris [2- (4-G4-oxymethylenephenyl) pyridineeto] iridium (III)

Tris [2- (4-G4-oxymethylenephenyl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 2]

¹ H-NMR (CDCl ₃ ): 8.69 (d, 1H), 7.88 (d, 1H), 7.56 (d, 1H), 7.47 (t, 1H) 7.19-7.34 (m, 82H), 7.02 (m, 1H ), 6.98 (t, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 782

Tris [2- (2'-methoxy-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2'-methoxy-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (2'-methoxy-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.29 (d, 1H, J = 8.4), 8.04 ( d, 1H, J = 2.1 Hz), 7.78-7.84 (m, 1H), 7.57-7.62 (m, 2H), 6.93-7.13 (m, 5H), 3.80 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 783

Tris [2- (2'-OG1-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (2'-OG1-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (2'-OG1-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.34 (m, 11H), 7.05 (t, 1H), 6.98 (t, 1H) , 6.88 (t, 1H), 6.79 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 ( s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 784

Tris [2- (3'-OG1-biphenyl-3 or 4-yl) pyridineeto] iridium

Tris [2- (3'-OG1-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (3'-OG1-biphenyl-4-yl) pyridineeto] iridium: ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d , 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.34 (m, 10H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 ( t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4 ), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 785

Tris [2- (4'-OG1-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (4'-OG1-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (4'-OG1-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.34 (m, 12H), 6.98 (t, 1H) , 6.79 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 ( s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 786

Tris [2- (2'-OG2-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (2'-OG2-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (2'-OG2-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.34 (m, 21H), 7.05 (t, 1H) , 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 787

Tris [2- (3'-OG2-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (3'-OG2-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (3'-OG2-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.33 (m, 20H), 7.15 (t, 1H), 7.05 (d, 1H) , 6.98 (t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 788

Tris [2- (4'-OG2-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (4'-OG2-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (4'-OG2-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.29-7.43 (m, 22H), 6.98 (d, 1H), 6.79 (d, 2H) , 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 789

Tris [2- (2'-OG3-biphenyl-3 or 4-yl) pyridyl] iridium (III)

Tris [2- (2'-OG3-biphenyl-3 or 4-yl) pyridyl] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (2'-OG3-biphenyl-4-yl) pyridyl] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.18-7.33 (m, 41H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (d, 1H), 6.79 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H) , 4.93 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 790

Tris [2- (3'-OG3-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (3'-OG3-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (3'-OG3-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.33 (m, 40H), 7.15 (t, 1H), 7.05 (d, 1H) , 6.98 (t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H ), 4.93 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 791

Tris [2- (4'-OG3-biphenyl-3 or 4-yl) pyridineeto] iridium (III)

Tris [2- (4'-OG3-biphenyl-3 or 4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

Tris [2- (4'-OG3-biphenyl-4-yl) pyridineeto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H), 7.19-7.33 (m, 42H), 6.98 (t, 1H) , 6.79 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 792

Tris [2- (2'-OG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (2'-OG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H ), 7.41 (t, 1H), 7.19-7.35 (m, 81H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 793

Tris [2- (3'-OG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (3'-OG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.19-7.33 (m, 80H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 794

Tris [2- (4'-OG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (4'-OG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.19-7.33 (m, 82H), 6.98 (t, 1H), 6.79 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 ( s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 795

Tris [2- (2'-methyleneoxyG1-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (2'-methyleneoxyG1-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.20-7.39 (m, 11H), 7.05 (d, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 796

Tris [2- (3'-methyleneoxyG1-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (3'-methyleneoxyG1-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.20-7.39 (m, 11H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (t, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 797

Tris [2- (3'-methyleneoxyG1-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (3'-methyleneoxyG1-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.05 (d, 2H), 7.57 (d, 2H), 7.54 (d, 1H), 7.50 (t, 1H), 7.49 (t, 1H ), 7.41 (t, 1H), 7.20-7.39 (m, 13H), 6.98 (t, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s , 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 798

Tris [2- (4'-methyleneoxyG1-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (4'-methyleneoxyG1-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H ), 7.41 (t, 1H), 7.20-7.39 (m, 13H), 6.98 (d, 1H), 6.79 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J) = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 799

Tris [2- (2'-methyleneoxyG2-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (2'-methyleneoxyG2-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.49 (t, 1H ), 7.41 (t, 1H), 7.17-7.37 (m, 21H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 800

Tris [2- (3'-methyleneoxyG2-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (3'-methyleneoxyG2-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.17-7.37 (m, 21H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (m, H), 6.93 (s, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s , 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 801

Tris [2- (4'-methyleneoxyG2-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (4'-methyleneoxyG2-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H ), 7.41 (t, 1H), 7.17-7.37 (m, 23H), 6.98 (t, 1H), 6.79 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 802

Tris [2- (2'-methyleneoxyG3-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (2'-methyleneoxyG3-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.49 (t, 1H), 7.17-7.31 (m , 42H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (d, 1H), 6.79 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 803

Tris [2- (3'-methyleneoxyG3-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (3'-methyleneoxyG3-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.50 (m, 2H), 7.17-7.31 (m, 41H), 7.15 (t , 1H), 7.05 (d, 1H), 6.98 (m 2H), 6.93 (s, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 804

Tris [2- (4'-methyleneoxyG3-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (4'-methyleneoxyG3-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.51 (d, 1H), 7.49 (t, 1H), 7.41 (t, 1H ), 7.17-7.31 (m, 42H), 6.98 (d, 1H), 6.79 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t , 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 805

Tris [2- (2'-methyleneoxyG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (2'-methyleneoxyG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.21 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.50 (m, 2H), 7.41 (t, 1H ), 7.19-7.34 (m, 81H), 7.05 (t, 1H), 6.98 (t, 1H), 6.88 (t, 1H), 6.79 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 806

Tris [2- (3'-methyleneoxyG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (3'-methyleneoxyG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.23 (s, 1H), 7.96 (d, 1H), 7.50 (m, 2H), 7.41 (t, 1H), 7.19-7.34 (m , 80H), 7.15 (t, 1H), 7.05 (d, 1H), 6.98 (d, 1H), 6.97 (d, 1H), 6.93 (s, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 807

Tris [2- (4'-methyleneoxyG4-biphenyl-3-yl) pyridineeto] iridium (III)

Tris [2- (4'-methyleneoxyG4-biphenyl-3-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 3]

¹ H-NMR (CDCl ₃ ): δ 8.55 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.54 (d, 1H), 7.51 (m, 2H), 7.41 (t, 1H ), 7.19-7.34 (m, 82H), 6.98 (t, 1H), 6.79 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 808

Tris [2- (5-methoxy-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-methoxy-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.31 (d, 1H), 6.00 (d, 1H), 3.83 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 809

Tris [2- (5-OG1-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-OG1-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.19-7.34 (m, 11H), 6.72 (m, 4H), 6.57 (t, 1H, J = 2.4) , 6.52 (d, 1H), 6.23 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 810

Tris [2- (5-OG2-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-OG2-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.20-7.34 (m, 21H), 6.73 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 4H), 6.24 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 811

Tris [2- (5-OG3-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-OG3-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.21-7.37 (m, 41H), 6.65-6.52 (m, 21H), 6.24 (d, 1H), 5.09 (m, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 812

Tris [2- (5-OG4-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-OG4-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.29-7.43 (m, 81H), 6.65-6.48 (m, 46H), 6.24 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 813

Tris [2- (5-methyleneoxyG1-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG1-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.00 (d, 1H), 7.80 (t, 1H), 7.20-7.49 (m, 11H), 6.55 (m, 2H), 6.24 (d, 1H), 5.02 (s , 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 814

Tris [2- (5-methyleneoxyG2-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG2-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.09 (d, 1H), 7.70 (t, 1H), 7.27-7.47 (m, 20H), 7.02 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.50 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.24 (d, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 815

Tris [2- (5-methyleneoxyG3-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG3-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.71 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 40H), 7.02 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 6H), 6.24 (d, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 816

Tris [2- (5-methyleneoxyG4-thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG4-thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 4]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 1H), 7.75 (t, 1H), 7.29-7.44 (m, 80H), 7.02 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.58 (d, 2H, J = 2.4), 6.44 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 585 nm.

Example 817

Tris [2- {5- (2-methoxy-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-methoxy-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.71 (t, 1H), 7.61 (d, 1H), 7.37 (d, 1H), 7.30 (t, 1H), 7.11 (t, 1H ), 7.02 (d, 2H), 6.88 (m, 2H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 818

Tris [2- {5- (2-OG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-OG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.09 (d, 1H), 7.69 (t, 1H), 7.29-7.44 (m, 12H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (d , 1H), 6.84 (d, 1H), 6.72 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 819

Tris [2- {5- (3-OG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-OG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.71 (t, 1H), 7.29-7.44 (m, 10H), 7.15 (t, 1H), 7.04 (t, 1H), 7.00 (d , 2H), 6.95 (d, 1H), 6.72 (m, 4H), 6.68 (d, 1H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 820

Tris [2- {5- (4-OG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-OG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.72 (t, 1H), 7.29-7.44 (m, 13H), 7.00 (d, 2H), 6.79 (d, 2H), 6.72 (m , 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 821

Tris [2- {5- (2-OG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-OG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 7.72 (t, 1H), 7.29-7.43 (m, 22H), 7.15 (t, 1H), 7.04 (t, 1H), 7.00 (d , 2H), 6.95 (d, 1H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 822

Tris [2- {5- (3-OG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-OG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.70 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 22H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (t, 1H), 6.84 (d, 1H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 ( s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 823

Tris [2- {5- (4-OG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-OG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.71 (t, 1H), 7.29-7.43 (m, 23H), 7.00 (d, 2H), 6.79 (d, 2H), 6.71 (m , 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.02 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 824

Tris [2- {5- (2-OG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-OG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 7.75 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 42H), 7.15 (t, 1H), 7.00 (m , 3H), 6.95 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.01 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 825

Tris [2- {5- (3-OG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-OG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.29-7.43 (m, 42H), 7.11 (t, 1H), 6.88 (t, 1H), 6.84 (d , 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.01 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 826

Tris [2- {5- (4-OG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-OG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.29-7.43 (m, 43H), 7.00 (d, 2H), 6.79 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 827

Tris [2- {5- (2-OG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-OG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 82H), 7.15 (t, 1H), 7.04 (m , 3H), 6.95 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 828

Tris [2- {5- (3-OG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-OG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 1H), 7.71 (t, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (d , 1H), 6.84 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 829

Tris [2- {5- (4-OG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-OG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.71 (t, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 83H), 7.00 (m, 4H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 830

Tris [2- {5- (2-methyleneoxyG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-methyleneoxyG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.30-7.49 (m, 12H), 7.15 (t, 1H), 7.04 (m , 3H), 6.95 (d, 1H), 6.57 (m, 3H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 831

Tris [2- {5- (3-methyleneoxyG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-methyleneoxyG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 7.70 (t, 1H), 7.30-7.49 (m, 12H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (t , 1H), 6.82 (d, 1H), 6.55 (m, 3H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 832

Tris [2- {5- (4-methyleneoxyG1-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-methyleneoxyG1-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.62 (d, 1H), 7.80 (t, 1H), 7.30-7.49 (m, 13H), 7.00 (d, 2H), 6.79 (d, 2H), 6.55 (m , 3H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 833

Tris [2- {5- (2-methyleneoxyG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-methyleneoxyG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.27-7.47 (m, 22H), 7.15 (t, 1H), 7.04 (m, 3H), 6.95 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.54 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s , 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 834

Tris [2- {5- (3-methyleneoxyG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-methyleneoxyG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.09 (d, 1H), 7.71 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 22H), 7.11 (t, 1H), 7.02 (d , 2H), 6.88 (m, 2H), 6.67 (d, 4H, J = 2.1), 6.62 (d, 2H, J = 2.4), 6.52 (m, 3H), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 835

Tris [2- {5- (4-methyleneoxyG2-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-methyleneoxyG2-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.71 (t, 1H), 7.61 (d, 1H), 7.27-7.47 (m, 23H), 7.00 (d, 2H), 6.79 (d , 2H), 6.67 (m, 6H), 6.54 (m, 3H), 4.99 (s, 8H), 4.91 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 836

Tris [2- {5- (2-methyleneoxyG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-methyleneoxyG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 42H), 7.15 (t, 1H), 7.04 (m , 3H), 6.95 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 4H), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 837

Tris [2- {5- (3-methyleneoxyG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-methyleneoxyG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.27-7.41 (m, 42H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (m , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 838

Tris [2- {5- (4-methyleneoxyG3-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-methyleneoxyG3-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.73 (t, 1H), 7.61 (d, 1H), 7.27-7.41 (m, 43H), 7.00 (d, 2H), 6.79 (d , 2H), 6.67 (m, 12H), 6.52 (m, 4H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 839

Tris [2- {5- (2-methyleneoxyG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (2-methyleneoxyG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.29-7.43 (m, 82H), 7.15 (t, 1H), 7.04 (m, 3H), 6.95 (d , 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.92 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 840

Tris [2- {5- (3-methyleneoxyG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (3-methyleneoxyG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.59 (d, 1H), 7.80 (t, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 7.02 (d, 2H), 6.88 (m , 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 841

Tris [2- {5- (4-methyleneoxyG4-phenyl) thiophen-2-yl} pyridineeto] iridium (III)

Tris [2- {5- (4-methyleneoxyG4-phenyl) thiophen-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 5]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.68 (t, 1H), 7.29-7.43 (m, 83H), 7.00 (d, 2H), 6.79 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 555 nm.

Example 842

Tris [2- {7- (4-methoxy-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-methoxy-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.18 (s, 1H), 8.11 (d, 2H), 7.93 (m, 2H), 7.77 (d, 1H), 7.60 (d, 1H ), 7.54 (d, 1H), 7.47 (t, 1H), 6.98 (t, 1H), 6.83 (d, 2H), 3.87 (s, 1H), 3.83 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 843

Tris [2- {7- (4-OG1-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-OG1-phenyl) -9H-fluoren-2-yl} pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 8.19 (s, 1H), 8.12 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.44 (m, 10H), 6.98 (t, 1H), 6.83 (d, 2H), 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 844

Tris [2- {7- (4-OG2-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-OG2-phenyl) -9H-fluoren-2-yl} pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.27 (d, 1H), 8.18 (s, 1H), 8.11 (d, 2H), 7.93 (m, 2H), 7.60 (d, 1H), 7.54 (d, 1H ), 7.46 (t, 1H), 7.29-7.43 (m, 20H), 6.98 (t, 1H), 6.83 (d, 2H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 ( s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 845

Tris [2- {7- (4-OG3-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-OG3-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.57 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 40H), 6.98 (d, 1H), 6.83 (d, 2H), 6.65-6.52 (m, 21H), 5.09 ( s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 846

Tris [2- {7- (4-OG4-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-OG4-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.56 (d, 1H), 8.28 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.54 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 80H), 6.98 (t, 1H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 ( s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 550 nm.

Example 847

Tris [2- {7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-methyleneoxyG1-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.09 (d, 1H), 8.18 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.54 (d, 1H), 7.47 (d, 1H), 7.30-7.49 (m, 11H), 6.98 (t, 1H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 848

Tris [2- {7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-methyleneoxyG2-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.17 (s, 1H), 8.11 (d, 2H), 7.93 (m, 2H), 7.77 (d, 1H), 7.60 (d, 1H ), 7.54 (d, 1H), 7.47 (t, 1H), 7.27-7.47 (m, 21H), 6.98 (t, 1H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 849

Tris [2- {7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-methyleneoxyG3-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.09 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.47 (d, 1H), 7.27-7.41 (m, 41H), 6.98 (t, 1H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 850

Tris [2- {7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl} pyridineeto] iridium (III)

Tris [2- {7- (4-methyleneoxyG4-phenyl) -9H-fluoren-2-yl} pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 6]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.17 (s, 1H), 8.11 (d, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H ), 7.60 (d, 1H), 7.47 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (t, 1H), 6.83 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.92 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 851

Tris [2- (6-methoxy-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-methoxy-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.72 (d, 1H), 7.70 (d, 1H), 7.42 (s, 1H), 7.33 (m, 2H), 3.73 (s, 1H ).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 852

Tris [2- (6-OG1-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-OG1-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.72 (m, 2H), 7.61 (d, 1H), 7.29-7.44 (m, 12H), 6.71 (d, 2H, J = 2.1) , 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 853

Tris [2- (6-OG2-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-OG2-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.72 (d, 1H), 7.70 (d, 1H), 7.61 (d, 1H), 7.29-7.43 (m, 23H), 6.71 (m , 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 854

Tris [2- (6-OG3-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-OG3-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.72 (m, 2H), 7.61 (d, 1H), 7.29-7.43 (m, 43H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 855

Tris [2- (6-OG4-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-OG4-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.72 (d, 1H), 7.70 (d, 1H), 7.29-7.43 (m, 83H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 856

Tris [2- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.72 (d, 1H), 7.70 (d, 1H), 7.30-7.49 (m, 13H), 6.55 (t, 1H, J = 2.1) , 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 857

Tris [2- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.72 (d, 1H), 7.70 (d, 1H), 7.27-7.47 (m, 23H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.5 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.73 (s , 1H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 858

Tris [2- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.73 (m, 2H), 7.61 (d, 1H), 7.27-7.41 (m, 43H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.52 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.73 (s , 1H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 859

Tris [2- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) pyridineeto] iridium (III)

Tris [2- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 7]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.73 (d, 1H), 7.70 (d, 1H), 7.29-7.43 (m, 83H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.73 (s, 1H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 860

Tris [2- (4-methoxy-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-methoxy-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.17 (d, 1H), 8.10 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.48 (t, 1H), 7.43 (t, 1H ), 7.31 (t, 1H), 6.98 (t, 1H), 6.72 (d, 1H), 3.89 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 861

Tris [2- (4-OG1-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-OG1-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.12 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.48 (t, 1H), 7.29-7.44 (m 12H), 6.98 (t, 1H), 6.72 (d, 1H), 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 862

Tris [2- (4-OG2-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-OG2-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 8.12 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H ), 7.29-7.43 (m, 22H), 6.98 (t, 1H), 6.74 (m, 3H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H) ), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 863

Tris [2- (4-OG3-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-OG3-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.03 (m, 2H), 7.72 (d, 1H), 7.48 (t, 1H), 7.29-7.43 (m, 42H), 6.98 (t , 1H), 6.70 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 864

Tris [2- (4-OG4-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-OG4-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.17 (d, 1H), 8.12 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.48 (t, 1H), 7.29-7.43 ( m, 82H), 6.98 (t, 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95 -4.92 (m, 28 H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 865

Tris [2- (4-methyleneoxyG1-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-methyleneoxyG1-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 8.03 (m, 2H), 7.72 (d, 1H), 7.30-7.49 (m, 13H), 6.98 (t, 1H), 6.71 (d , 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 866

Tris [2- (4-methyleneoxyG2-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-methyleneoxyG2-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.15 (d, 1H), 8.03 (m, 2H), 7.72 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H), 7.27-7.47 (m , 22H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (m, 3H), 4.99 (s , 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 867

Tris [2- (4-methyleneoxyG3-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-methyleneoxyG3-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.17 (d, 1H), 8.09 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.48 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.51 ( m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 868

Tris [2- (4-methyleneoxyG4-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (4-methyleneoxyG4-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 8]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 1H), 8.12 (d, 1H), 8.03 (d, 1H), 7.72 (d, 1H), 7.48 (t, 1H), 7.29-7.43 (m , 82H), 6.62-6.67 (m, 43H, J = 2.1), 6.98 (t, 1H), 6.71 (d, 1H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.92 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 867

Tris [2- (5-methoxy-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-methoxy-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.28 (d, 1H), 8.11 (m, 2H), 7.52 (d, 1H), 7.46 (m, 2H), 7.33 (d, 1H), 7.21 (t, 1H ), 6.98 (t, 1 H), 6.67 (d, 1 H), 3.79 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 615 nm.

Example 868

Tris [2- (5-OG1-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-OG1-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.28 (d, 1H), 8.13 (m, 2H), 7.52 (d, 1H), 7.46 (m, 2H), 7.29-7.44 (m, 10H), 7.21 (t , 1H), 6.98 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.67 (d, 1H), 6.57 (t, 1H, J = 2.4) , 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 615 nm.

Example 869

Tris [2- (5-OG2-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-OG2-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.10 (m, 2H), 7.52 (d, 1H), 7.46 (m, 2H), 7.29-7.43 (m, 21H), 7.21 (t , 1H), 6.98 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.67 (d, 1H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 615 nm.

Example 870

Tris [2- (5-OG3-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-OG3-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.11 (m, 2H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H), 7.29-7.43 (m , 41H), 7.21 (t, 1H), 6.98 (t, 1H), 6.67 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 615 nm.

Example 871

Tris [2- (5-OG4-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-OG4-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.09 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H), 7.29-7.43 (m, 81H), 7.21 (t , 1H), 6.98 (t, 1H), 6.67 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95- 4.92 (m, 28 H).

λ _em (CH ₂ Cl ₂ ) = 615 nm.

Example 872

Tris [2- (5-methyleneoxyG1-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG1-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.07 (m, 2H), 7.52 (d, 1H), 7.30-7.49 (m, 13H), 7.21 (t, 1H), 6.98 (t , 1H), 6.67 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 873

Tris [2- (5-methyleneoxyG2-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG2-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.03 (m, 2H), 7.52 (d, 1H), 7.46 (t, 1H), 7.44 (t, 1H), 7.27-7.47 (m , 21H), 7.21 (t, 1H), 6.98 (t, 1H), 6.68 (d, 5H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 874

Tris [2- (5-methyleneoxyG3-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG3-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.19 (d, 1H), 8.03 (m, 2H), 7.52 (d, 1H), 7.46 (m, 2H), 7.27-7.41 (m, 41H), 7.21 (t , 1H), 6.98 (t, 1H), 6.72 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 6H), 4.99 (s , 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 875

Tris [2- (5-methyleneoxyG4-naphthalene-1-yl) pyridineeto] iridium (III)

Tris [2- (5-methyleneoxyG4-naphthalen-1-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 9]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 8.04 (m, 2H), 7.46 (m, 2H), 7.29-7.43 (m, 82H), 6.98 (t, 1H), 6.69 (d , 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 876

Tris [2- (2,3,6-trifluro-4'-methoxybiphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-methoxybiphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.41 (s, 1H), 7.48 (t, 1H), 7.36 (d, 1H), 6.98 (d, 2H), 6.83 (d, 2H ), 3.87 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 485 nm.

Example 877

Tris [2- (2,3,6-trifluro-4'-OG1-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.45 (d, 1H), 7.51 (s, 1H), 7.48 (t, 1H), 7.29-7.44 (m, 10H), 6.98 (d , 2H), 6.83 (d, 2H), 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 485 nm.

Example 878

Tris [2- (2,3,6-trifluro-4'-OG2-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.51 (s, 1H), 7.29-7.43 (m, 22H), 6.98 (d, 2H), 6.83 (d, 2H), 6.71 (m , 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 485 nm.

Example 879

Tris [2- (2,3,6-trifluro-4'-OG3-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.18 (d, 1H), 7.45 (m, 2H), 7.29-7.43 (m, 41H), 6.98 (d, 2H), 6.83 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 485 nm.

Example 880

Tris [2- (2,3,6-trifluro-4'-OG4-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) pyridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.51 (s, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (d, 2H), 6.83 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 485 nm.

Example 881

Tris [2- (2,3,6-trifluro-4'-methyleneoxyG1-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.45 (d, 1H), 7.31 (s, 1H), 7.30-7.49 (m, 12H), 6.98 (d, 2H), 6.83 (d , 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 480 nm.

Example 882

Tris [2- (2,3,6-trifluro-4'-methyleneoxyG2-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.51 (s, 1H), 7.38 (t, 1H), 7.27-7.47 (m, 21H), 6.98 (d, 2H), 6.83 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s , 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 480 nm.

Example 883

Tris [2- (2,3,6-trifluro-4'-methyleneoxyG3-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.51 (s, 1H), 7.42 (t, 1H), 7.27-7.41 (m, 41H), 6.98 (d, 2H), 6.83 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 480 nm.

Example 884

Tris [2- (2,3,6-trifluro-4'-methyleneoxyG4-biphenyl-4-yl) pyridineeto] iridium (III)

Tris [2- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 10]

¹ H-NMR (CDCl ₃ ): δ 8.08 (d, 1H), 7.51 (s, 1H), 7.38 (t, 1H), 7.29-7.43 (m, 81H), 6.98 (d, 2H), 6.83 (d , 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 480 nm.

Example 885

Tris [1- (2-methoxy-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-methoxy-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-methoxy-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H ), 7.62 (t, 1H), 7.51 (t, 1H), 7.17 (t, 1H), 6.92 (d, 1H), 6.88 (d, 1H), 3.74 (s, 3H), 2.35 (s, 3H) .

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 886

Tris [1- (2-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-OG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.91 (s, 1H), 7.72 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.71 (d, 2H , J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH _3: λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 887

Tris [1- (3-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-OG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.62 (t, 1H) , 7.51 (m, 2H), 7.49 (s, 1H), 7.29-7.44 (m, 10H), 7.25 (t, 1H), 6.78 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH _3: λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 888

Tris [1- (4-OG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG1-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-OG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.89 (s, 1H), 7.81 (d, 2H) , 7.62 (d, 1H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 6.71 (d, 2H, J = 2.1), 6.87 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 889

Tris [1- (2-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-OG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.62 (t, 1H) , 7.51 (t, 1H), 7.29-7.43 (m, 20H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 890

Tris [1- (3-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-OG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ7.92 (s, 1H), 7.62 (t, 1H ), 7.56 (d, 1H), 7.51 (d, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 20H), 7.25 (t, 1H), 6.78 (d, 1H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 891

Tris [1- (4-OG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG2-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-OG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 6.87 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 892

Tris [1- (2-OG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-OG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H) , 7.62 (t, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 40H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.65-6.52 (m , 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ e) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 893

Tris [1- (3-OG3-phenyl) -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Trsi [1- (3-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-OG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H) , 7.62 (t, 1H), 7.51 (d, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 40H), 7.25 (t, 1H), 6.78 (d, 1H), 6.65-6.52 (m , 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 894

Tris [1- (4-OG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-OG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H) , 7.62 (t, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 40H), 6.87 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s , 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 895

Tris [1- (2-OG4-phenyl) -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- (2-OG4-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-OG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H) , 7.62 (t, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 80H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.65-6.48 (m , 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 896

Tris [1- (3-OG4-phenyl) -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- (3-OG4-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-OG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.29-7.43 (m, 80H), 7.25 (t, 1H), 6.78 (d, 1H), 6.65-6.48 (m , 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 897

Tris [1- (4-OG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG4-phenyl) -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-OG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H) , 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 6.87 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s , 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 898

Tris [1- (2-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-methyleneoxyG1-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-methyleneoxyG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 899

Tris [1- (3-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-methyleneoxyG1-phenyl) -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-methyleneoxyG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.49 (s, 1H), 7.30-7.49 (m, 11H), 7.25 (t, 1H), 6.78 (d, 1H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 900

Tris [1- (4-methyleneoxyG1-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG1-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-methyleneoxyG1-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H), 7.62 (t, 1H), 7.51 (d, 1H), 7.30-7.49 (m, 11H), 6.87 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H) , 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 901

Tris [1- (2-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-methyleneoxyG2-phenyl) -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-methyleneoxyG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.67 (m) , 6H), 6.54 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 902

Tris [1- (3-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-methyleneoxyG2-phenyl) -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-methyleneoxyG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.49 (m, 2H), 7.27-7.47 (m, 21H), 7.25 (t, 1H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.52 (m, 3H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H) , 2.35 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 903

Tris [1- (4-methyleneoxyG2-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG2-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-methyleneoxyG2-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 6.87 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.53 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 904

Tris [1- (2-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-methyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-methyleneoxyG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.17 (t, 1H), 6.92 (d, 1H), 6.88 (d, 1H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 905

Tris [1- (3-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-methyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-methyleneoxyG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.51 (m, 2H), 7.27-7.41 (m, 40H), 7.25 (t, 1H), 6.68 (m, 8H), 6.64 (d , 4H, J = 2.4), 6.54 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 906

Tris [1- (4-methyleneoxyG3-phenyl) -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG3-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-methyleneoxyG3-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H), 7.62 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 6.87 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 907

Tris [1- (2-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2-methyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (2-methyleneoxyG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.17 (t, 1H), 6.92 (t, 1H), 6.88 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 908

Tris [1- (3-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3-methyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (3-methyleneoxyG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.79 (d, 2H), 7.62 (t, 1H), 7.56 (d, 1H), 7.51 (m, 2H), 7.29-7.43 (m, 81H), 7.25 (t, 1H), 6.62-6.67 (m, 44H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.35 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 909

Tris [1- (4-methyleneoxyG4-phenyl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG4-phenyl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 12]

Tris [1- (4-methyleneoxyG4-phenyl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.78 (d, 2H), 7.62 (t, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 81H), 6.87 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 910

Tris [1- (2'-methoxy-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-methoxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoli-

nato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-methoxy-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H) , 7.95 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.11 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1 H), 3.74 (s, 3 H), 2.32 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 911

Tris [1- (2'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-OG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.85 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 11H), 7.11 (t, 1H) , 6.88 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 ( s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 912

Tris [1- (3'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-OG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.71 (d, 2H), 7.62 (t, 1H), 7.57 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 10H), 7.22 (t, 1H), 7.05 (d, 1H) , 6.99 (d, 1H), 6.73 (m, 5H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 913

Tris [1- (4'-OG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-OG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-OG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.96 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.44 (m, 12H), 6.83 (d, 2H) , 6.71 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 914

Tris [1- (2'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-OG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.85 (d, 2H), 7.67 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 21H), 7.11 (t, 1H) , 6.88 (t, 1H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H ).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 915

Tris [1- (3'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-OG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.86 (d, 2H), 7.71 (d, 2H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 7.22 (t, 1H), 7.05 (m, 2H) , 6.99 (d, 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 916

Tris [1- (4'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-OG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ8.02 (s, 1H) , 7.95 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 22H), 6.83 (d, 2H ), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s , 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 917

Tris [1- (2'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (IIII)

Tris [1- (2'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-OG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (IIII): ¹ H-NMR (CDCl ₃ ): δ 7.93 (s, 1H), 7.85 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 41H), 7.11 (t, 1H) , 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H ), 2.32 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 918

Tris [1- (3'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-OG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.86 (d, 2H), 7.71 (m, 3H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 7.22 (t, 1H), 7.05 (d, 1H) , 6.99 (d, 1H), 6.73 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H ), 2.32 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 919

Tris [1- (4'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-OG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.96 (d, 2H), 7.71 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 42H), 6.83 (d, 2H) , 6.65-6.52 (m, 21 H), 5.09 (s, 2 H), 5.03 (s, 16 H), 4.99 (s, 8 H), 4.93 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 920

Tris [1- (2'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-OG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.85 (d, 2H), 7.80 (d, 2H), 7.57 (m, 3H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.88 (t, 1H) , 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.32 (s , 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 921

Tris [1- (3'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinoline] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-OG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.96 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 7.22 (t, 1H) , 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H ), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 922

Tris [1- (4'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-OG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.86 (d, 2H), 7.73 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 82H), 6.83 (d, 2H) , 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 625 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 923

Tris [1- (2'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-methyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H ), 7.85 (d, 2H), 7.71 (d, 2H), 7.62 (t, 1H), 7.58 (m, 3H), 7.30-7.49 (m, 11H), 7.11 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 924

Tris [1- (3'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-methyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H ), 7.96 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.30-7.49 (m, 11H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 925

Tris [1- (4'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-methyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H ), 7.86 (d, 2H), 7.71 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.30-7.49 (m, 12H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 926

Tris [1- (2'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-methyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H ), 7.85 (d, 2H), 7.72 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.11 (t, 1H), 6.88 (t, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 927

Tris [1- (3'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-methyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H ), 7.86 (d, 2H), 7.75 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 21H), 7.22 (t, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 928

Tris [1- (4'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-methyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H ), 7.86 (d, 2H), 7.73 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.47 (m, 22H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.54 (m, 3H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 929

Tris [1- (2'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-methyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.93 (s, 1H ), 7.75 (d, 2H), 7.71 (m, 3H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.11 (t, 1H), 6.88 (d, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 930

Tris [1- (3'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-methyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H ), 7.96 (d, 2H), 7.81 (d, 2H), 7.58 (m, 3H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 7.22 (t, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 931

Tris [1- (4'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4'-methyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H ), 7.96 (d, 2H), 7.71 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.27-7.41 (m, 41H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (m, 6H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 932

Tris [1- (2'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2'-methyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (2'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H ), 7.85 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.88 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 ( s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 933

Tris [1- (3'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (3'-methyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (3'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H ), 7.96 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 7.22 (d, 1H), 6.99 (d, 1H), 6.73 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 ( s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 934

Tris [1- (4'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Trsi [1- (4'-methyleneoxyG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] irdium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 13]

Tris [1- (4'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H ), 7.96 (d, 2H), 7.81 (d, 2H), 7.62 (t, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 6.83 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 ( d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 620 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 615 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 935

Tris [1- (5-methoxy-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-methoxy-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoli-

nato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-methoxy-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III)

¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 6.66 (d, 1H), 3.80 (s, 3H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 665 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 660 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 936

Tris [1- (5-OG1-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-OG1-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato]

iridum (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-OG1-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (d, 1H), 7.29-7.44 (m, 10H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4) , 6.01 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 665 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 660 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 937

Tris [1- (5-OG2-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-OG2-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridum (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-OG2-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 20H), 6.71 (m, 6H), 6.66 (d, 1H), 6.54-6.58 (m, 3H ), 6.01 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 665 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 660 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 938

Tris [1- (5-OG3-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-OG3-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-OG3-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 20H), 6.66 (d, 1H), 5.09 (s, 2H ), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 665 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 660 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 939

Tris [1- (5-OG4-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-OG4-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-OG4-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.91 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 80H), 6.65-6.48 (m, 46H), 6.01 (d, 1H), 5.09 (s, 2H ), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 665 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 660 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 940

Tris [1- (5-methyleneoxyG1-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-methyleneoxyG1-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-methyleneoxyG1-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H) , 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (d, 1H), 7.30-7.49 (m, 10H), 6.55 (t, 1H, J = 2.1), 6.01 (d, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 941

Tris [1- (5-methyleneoxyG2-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-methyleneoxyG2-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-methyleneoxyG2-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H) , 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.27-7.47 (m, 20H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.53 (m, 3H), 6.01 (d, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.33 (s, 3H) ).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 942

Tris [1- (5-methyleneoxyG3-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-methyleneoxyG3-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinoli-nato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-methyleneoxyG3-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H) , 7.71 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.27-7.41 (m, 40H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (m, 6H), 6.01 (d, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3H ).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 943

Tris [1- (5-methyleneoxyG4-thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (5-methyleneoxyG4-thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] irdium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 14]

Tris [1- (5-methyleneoxyG4-thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H) , 7.70 (d, 2H), 7.63 (t, 1H), 7.51 (t, 1H), 7.29-7.43 (m, 81H), 6.62-6.67 (m, 44H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.01 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 944

Tris [1- [5- (2-methoxy-phenyl) -thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- [5- (2-methoxy-phenyl) -thiophen-2-yl] -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tricy [1- [5- (2-methoxy-phenyl) -thiophen-2-yl] -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.82 (d, 2H), 7.77 (t, 1H), 7.55 (m, 2H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1 H), 3.82 (s, 3 H), 2.34 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 945

Tris [1- {5- (2-OG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-OG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-OG1-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 ( s, 1H), 7.77 (m, 3H), 7.55 (t, 1H), 7.29-7.44 (m, 11H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 946

Tris [1- {5- (3-OG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-OG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-OG1-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.72 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.29-7.44 (m, 10H), 7.24 (t, 1H), 7.07 (m, 3H), 6.99 (d, 1H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 947

Tris [1- {5- (4-OG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-OG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-OG1-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.71 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.29-7.44 (m, 12H), 7.05 (d, 2H), 6.89 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH _3: λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 948

Tris [1- {5- (2-OG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-OG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-OG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 ( s, 1H), 7.72 (m, 3H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 20H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 949

Tris [1- {5- (3-OG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-OG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-OG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 ( s, 1H), 7.72 (d, 2H), 7.65 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 20H), 7.24 (t, 1H), 7.07 (m, 3H), 6.99 (d, 1H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H) , 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 950

Tris [1- {5- (4-OG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-OG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-OG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.71 (d, 2H), 7.65 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 22H), 7.05 (d, 2H), 6.89 (d, 2H), 6.71 (m, 6H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 951

Tris [1- {5- (2-OG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-OG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-OG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 ( s, 1H), 7.77 (m, 3H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 40H), 7.11 (t, 1H), 7.05 (d, 2H), 6.89 (t, 1H), 6.83 (d, 1H), 7.25 (t, 1H), 7.02 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 952

Tris [1- {5- (3-OG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-OG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-OG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.76 (m, 3H), 7.55 (t, 1H), 7.29-7.43 (m, 40H), 7.24 (t, 1H), 7.07 (d, 1H), 7.05 (d, 2H), 6.75 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 953

Tris [1- {5- (4-OG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-OG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-OG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.76 (m, 3H), 7.55 (t, 1H), 7.29-7.43 (m, 42H), 7.05 (d, 2H), 6.89 (d, 2H), 6.65-6.52 (m, 21H) , 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 954

Tris [1- {5- (2-OG4-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III)

Tris [1- {5- (2-OG4-phenyl) -thiophen-2-yl} -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.72 (m, 3H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 80H), 7.11 (t , 1H), 7.05 (d, 2H), 6.89 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95- 4.92 (m, 28 H), 2.34 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 955

Tris [1- {5- (3-OG4-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- {5- (3-OG4-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1-5- (3-OG4-phenyl) -thiophen-2-yl-4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 80H), 7.24 (t, 1H), 7.07 (d, 1H), 7.05 (d, 2H), 6.99 (d , 1H), 6.75 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 2.34 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 956

Tris [1- {5- (4-OG4-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- {5- (4-OG4-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -iso quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-OG4-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.71 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 81H), 7.05 (d, 2H), 6.89 (d, 2H), 6.65 -6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 957

Tris [1- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.72 (d, 2H), 7.67 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.30-7.49 (m, 10H), 7.11 (t, 1H) , 7.05 (d, 2H), 6.89 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s , 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 958

Tris [1- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Trsi [1- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.72 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.30-7.49 (m, 10H), 7.24 (t, 1H), 7.07 (d, 1H) , 7.05 (d, 2H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s , 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 959

Tris [1- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1-5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl-4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 ( s, 1H), 7.71 (d, 2H), 7.55 (t, 1H), 7.30-7.49 (m, 12H), 7.05 (d, 2H), 6.89 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 960

Tris [1- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.72 (d, 2H), 7.67 (t, 1H), 7.55 (t, H), 7.27-7.47 (m, 21H), 7.11 (t, 1H), 7.05 (d, 2H) , 6.89 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4 ), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 961

Tris [1- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.72 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.27-7.47 (m, 20H), 7.24 (d, 1H), 7.07 (t, 1H) , 7.05 (d, 2H), 6.75 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 ( t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 962

Tris [1- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.71 (d, 2H), 7.66 (t, 1H), 7.27-7.47 (m, 22H), 7.05 (d, 2H), 6.89 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H ), 4.61 (s, 2H), 4.52 (s, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 963

Tris [1- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.72 (d, 2H), 7.67 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.27-7.41 (m, 40H), 7.11 (t, 1H) , 7.05 (d, 2H), 6.89 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 ( t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 964

Tris [1- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.72 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.27-7.41 (m, 40H), 7.24 (t, 1H), 7.07 (d, 1H) , 7.05 (d, 2H), 6.75 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 ( t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 965

Tris [1- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8 .05 (s, 1H), 7.71 (d, 2H), 7.66 (t, 1H), 7.38 (d, 2H), 7.27-7.41 (m, 41H), 7.05 (d, 2H), 6.89 (d, 2H ), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 966

Tris [1- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.72 (d, 2H), 7.67 (t, 1H), 7.55 (t, H), 7.44 (d, 1H), 7.29-7.43 (m, 80H), 7.11 (t, 1H) , 7.05 (d, 2H), 6.89 (d, 1H), 6.62-6.67 (m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 967

Tris [1- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.72 (d, 2H), 7.66 (t, 1H), 7.55 (t, 1H), 7.29-7.43 (m, 81H), 7.24 (t, 1H), 7.07 (d, 1H) , 7.05 (d, 2H), 6.75 (d, 1H), 6.62-6.67 (m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 968

Tris [1- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 15]

Tris [1- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.05 (s, 1H), 7.71 (d, 2H), 7.66 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (d, 2H), 6.89 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1, 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.34 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 645 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 640 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 969

Tris [1- {7- (2-methoxy-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-methoxy-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-methoxy-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.17 (m, 2H), 8.12 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 3.88 (d, 2H), 3.73 (s, 3H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 705 nm.

Example 970

Tris [1- {7- (2-OG1-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- {7- (2-OG1-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-OG1-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.07 (m, 2H), 7.93 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (d, 1H), 7.29 -7.44 (m, 11H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4) , 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 705 nm.

Example 971

Tris [1- {7- (2-OG2-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-OG2-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-OG2-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 8.07 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.29-7.43 (m, 21H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d , 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H ).

4-H: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 705 nm.

Example 972

Tris [1- {7- (2-OG3-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-OG3-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-OG3-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.07 (s, 1H), 8.01 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.29-7.43 (m, 41H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H ), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 705 nm.

Example 973

Tris [1- {7- (2-OG4-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-OG4-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ )-isoquinolinato] iridium (III)

Synthesis and purification was carried out by a method similar to the synthesis method of the foregoing iridium (III) complex.

Tris [1- {7- (2-OG4-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.07 (s, 1H), 8.01 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H), 7.55 (t, 1H), 7.29-7.43 (m, 81H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H ), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 705 nm.

Example 974

Tris [1- {7- (2-methyleneoxyG1-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-methyleneoxyG1-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-methyleneoxyG1-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ) : δ 8.07 (s, 1H), 8.01 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H) , 7.55 (t, 1H), 7.30-7.49 (m, 11H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 685 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 700 nm.

Example 975

Tris [1- {7- (2-methyleneoxyG2-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-methyleneoxyG2-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-methyleneoxyG2-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ) δ 8.11 (s, 1H), 8.07 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H) , 7.55 (t, 1H), 7.27-7.47 (m, 21H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 685 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 700 nm.

Example 976

Tris [1- {7- (2-methyleneoxyG3-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-methyleneoxyG3-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-methyleneoxyG3-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ) δ 8.11 (s, 1H), 8.07 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H) , 7.55 (t, 1H), 7.27-7.41 (m, 41H), 7.12 (d, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.88 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 685 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 700 nm.

Example 977

Tris [1- {7- (2-methyleneoxyG4-phenyl) -9H-floren-2-yl} -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- {7- (2-methyleneoxyG4-phenyl) -9H-fluoren-2-yl} -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 16]

Tris [1- {7- (2-methyleneoxyG4-phenyl) -9H-floren-2-yl} -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ) δ 8.11 (s, 1H), 8.07 (s, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.82 (d, 2H), 7.78 (s, 1H), 7.60 (m, 2H) , 7.55 (d, 1H), 7.29-7.43 (m, 81H), 7.12 (t, 1H), 6.88 (t, 1H), 6.83 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1) , 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.88 (d, 2H), 2.32 (s , 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 690 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 685 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 700 nm.

Example 978

Tris [1- (6-methoxy-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-methoxy-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-methoxy-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.11 (s , 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.43 (s, 1H), 7.33 (s, 1H), 6.82 (d, 1H), 3.79 (s, 3H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 979

Tris [1- (6-OG1-Benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-OG1-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoqui-

nolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-OG1-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 7.78 (d, 2H), 7.61 (t, 1H), 7.52 (d, 1H), 7.29-7.44 (m, 12H), 6.82 (d, 1H), 6.72 (d, 2H, J = 2.4) , 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 980

Tris [1- (6-OG2-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-OG2-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoqui-

nolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-OG2-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 2H), 7.61 (t, 1H), 7.52 (d, 1H), 7.29-7.43 (m, 22H), 6.82 (d, 1H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 981

Tris [1- (6-OG3-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-OG3-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoqui-

nolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-OG3-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 42H), 6.82 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 982

Tris [1- (6-OG4-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-OG4-benzo [b] thiophen-2-yl] -4- (H, F or CH ₃ ) -isoqui-

nolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-OG4-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 6.82 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 983

Tris [1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 ( s, 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.30-7.49 (m, 12H), 6.82 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 720 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 725 nm.

Example 984

Tris [1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridum (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 ( s, 1H), 7.78 (d, 2H), 7.68 (d, 1H), 7.61 (t, 1H), 7.52 (t, 1H), 7.27-7.47 (m, 22H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2 H), 4.52 (s, 2 H), 2.32 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 700 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 710 nm.

Example 985

Tris [1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 ( s, 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.43 (s, 1H), 7.27-7.41 (m, 41H), 6.82 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 700 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 710 nm.

Example 986

Tris [1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -4- (hydro, fluoro or methyl) isocurolineto] iridium (III)

Tris [1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 17]

Tris [1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.01 ( s, 1H), 7.78 (d, 2H), 7.61 (d, 1H), 7.52 (t, 1H), 7.29-7.43 (m, 82H), 6.82 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H) .

4-H: λ _em (CH ₂ Cl ₂ ) = 700 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 695 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 710 nm.

Example 987

Tris [1- (4-methoxy-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-methoxy-naphthalen-1-yl] -4- (H, F or CH ₃ ) -isoquinoli

nato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

Tris [1- (4-methoxy-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 8.02 (m, 2H), 7.82 (d, 2H), 7.61 (t, 1H), 7.53 (t, 1H), 7.42 (d, 1H), 7.32 (t, 1H), 6.75 (d, 1H), 3.73 ( s, 3H), 2.32 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 988

Tris [1- (4-OG1-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG1-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

Tris [1- (4-OG1-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.13 (s, 1H), 8.02 ( m, 2H), 7.82 (d, 2H), 7.74 (d, 1H), 7.61 (d, 1H), 7.53 (t, 1H), 7.29-7.44 (m, 12H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 2.32 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 989

Tris [1- (4-OG2-naphthalene-1-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (4-OG2-naphthalen-1-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

Tris [1- (4-OG2-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.13 (s, 1H), 8.02 ( m, 2H), 7.82 (d, 2H), 7.61 (d, 1H), 7.53 (t, 1H), 7.29-7.43 (m, 22H), 6.71 (d, 2H, J = 2.1), 6.75 (d, 1H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.32 (s, 3H) .

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 990

Tris [1- (4-OG3-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-OG3-naphthalen-1-yl) -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.92 (m, 2H), 7.82 (d, 2H), 7.61 (t, 1H), 7.53 (d, 1H), 7.29-7.43 (m , 40H), 6.75 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.32 ( s, 3H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 991

Tris [1- (4-OG4-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-OG4-naphthalen-1-yl) -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.92 (m, 2H), 7.82 (d, 2H), 7.61 (t, 1H), 7.53 (d, 1H), 7.29-7.43 (m , 82H), 6.75 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.32 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 992

Tris [1- (4-methyleneoxyG1-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG1-naphthalen-1-yl) -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.94 (m, 2H), 7.82 (d, 2H), 7.61 (d, 1H), 7.53 (t, 1H), 7.42 (t, 1H ), 7.30-7.49 (m, 11H), 6.75 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.32 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 993

Tris [1- (4-methyleneoxyG2-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG2-naphthalen-1-yl) -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.94 (m, 2H), 7.82 (d, 2H), 7.61 (t, 1H), 7.53 (d, 1H), 7.27-7.47 (m , 22H), 6.75 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.32 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 994

Tris [1- (4-methyleneoxyG3-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG3-naphthalen-1-yl] -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.93 (m, 2H), 7.82 (d, 2H), 7.61 (t, 1H), 7.53 (d, 1H), 7.42 (t, 1H ), 7.27-7.41 (m, 41H), 6.75 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.32 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 995

Tris [1- (4-methyleneoxyG4-naphthalene-1-yl) -4-methyl-isocurolineto] iridium (III)

Tris [1- (4-methyleneoxyG4-naphthalen-1-yl) -4-methyl-isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 18]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.94 (m, 2H), 7.82 (d, 2H), 7.61 (d, 1H), 7.53 (t, 1H), 7.29-7.43 (m , 82H), 6.75 (d, 1H), 6.62-6.67 (m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H ), 4.52 (d, 2H), 2.32 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 996

Tris [1- (2,3,6-triproro-4'-methoxy-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methyoxy-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-triproro-4'-methoxy-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.38 (d, 2H), 7.05 (s, 1H), 6.88 (d, 2H), 3.76 (s, 3H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 998

Tris [1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.29-7.43 (m, 22H), 7.05 (s, 1H), 6.88 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 2.33 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 999

Tris [1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.29-7.43 (m, 42H), 7.05 (s, 1H), 6.88 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1000

Tris [1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (s, 1H), 6.88 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1001

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III )

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR ( CDCl ₃ ): δ 8.03 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.52 (t, 1H), 7.30-7.49 (m, 12H), 6.88 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 585 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1002

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III )

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR ( CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.27-7.47 (m, 22H), 7.05 (s, 1H), 6.88 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 585 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1003

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III )

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR ( CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.27-7.41 (m, 42H), 7.05 (s, 1H), 6.88 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 2.33 (s, 3H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 585 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1004

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -4- (hydro, fluoro or methyl) -isocurolineto] iridium (III )

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl] -4- (H, F or CH ₃ ) -isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 20]

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -4-methyl-isocurolineto] iridium (III): ¹ H-NMR ( CDCl ₃ ): δ 8.04 (s, 1H), 7.73 (t, 2H), 7.61 (t, 1H), 7.29-7.43 (m, 82H), 7.05 (s, 1H), 6.88 (d, 2H), 6.62 -6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H) , 2.33 (s, 3 H).

4-H: λ _em (CH ₂ Cl ₂ ) = 590 nm.

4-F: λ _em (CH ₂ Cl ₂ ) = 585 nm.

4-CH ₃ : λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1005

Tris [6- (4-methoxy-phenyl) -phenanthridiene] iridium (III)

Tris [6- (4-methoxy-phenyl) -phenanthridinate] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 8.00 (d, 1H), 7.77 (d, 1H), 7.62 (m, 3H), 7.59 (t, 1H), 7.52 (t, 1H), 7.88 (d, 2H ), 7.45 (t, 1 H), 6.86 (d, 2 H), 3.75 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1006

Tris [6- (2-OG1-phenyl) -phenanthtridiene] iridium (III)

Tris [6- (2-OG1-phenyl) -phenanthridinate] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.78 (d, 2H), 7.72 (m, 3H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.44 (m, 10H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1007

Tris [6- (3-OG1-phenyl) -phenanthtridiene] iridium (III)

Tris [6- (3-OG1-phenyl) -phenanthridinate] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.77 (d, 1H), 7.61 (m, 2H), 7.59 (t, 1H), 7.52 (s, 1H), 7.45 (t, 1H ), 7.29-7.44 (m, 10H), 7.27 (t, 1H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1008

Tris [6- (4-OG1-phenyl) -phenanthtridiene] iridium (III)

Tris [6- (4-OG1-phenyl) -phenanthridinate] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

1 H-NMR (CDCl ₃ ): δ 8.00 (d, 1H), 7.78 (d, 2H), 7.67 (m, 3H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H) , 7.45 (t, 1H), 7.29-7.44 (m, 10H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1009

Tris [6- (2-OG2-phenyl) -phenanthridiene] iridium (III)

Tris [6- (2-OG2-phenyl) -phenanthridinate] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.79 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 20H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1010

Tris [6- (3-OG2-phenyl) -phenanthridiene] iridium (III)

Tris [6- (3-OG2-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.77 (d, 1H), 7.62 (m, 3H), 7.59 (t, 1H), 7.52 (s, 1H), 7.45 (t, 1H ), 7.29-7.43 (m, 20H), 7.27 (t, 1H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1011

Tris [6- (4-OG2-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG2-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 20H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1012

Tris [6- (2-OG3-phenyl) -phenanthridineeto] iridium (III)

Tris [6- (2-OG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.79 (d, 2H), 7.72 (m, 2H), 7.59 (m, 2H), 7.52 (t, 1H), 7.45 (t, 1H ), 7.29-7.43 (m, 40H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1013

Tris [6- (3-OG3-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (3-OG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.77 (d, 1H), 7.61 (m, 2H), 7.59 (t, 1H), 7.52 (s, 1H), 7.45 (t, 1H ), 7.29-7.43 (m, 40H), 7.27 (t, 1H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.65-6.52 (m, 21H), 5.09 ( s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1014

Tris [6- (4-OG3-phenyl) -phenanthridineeto] iridium (III)

Tris [6- (4-OG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.79 (d, 2H), 7.72 (m, 3H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (d, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 40H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1015

Tris [6- (2-OG4-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (2-OG4-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.88 (d, 2H), 7.87 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H ), 7.52 (t, 1H), 7.45 (t, 1H), 7.29-7.43 (m, 80H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1016

Tris [6- (3-OG4-phenyl) -phenanthridineeto] iridium (III)

Tris [6- (3-OG4-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.95 (d, 1H), 7.77 (d, 1H), 7.62 (m, 2H), 7.59 (t, 1H), 7.52 (s, 1H), 7.45 (t, 1H ), 7.29-7.43 (m, 80H), 7.27 (t, 1H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.65-6.48 (m, 45H), 5.09 ( s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1017

Tris [6- (4-OG4-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG4-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.79 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (d, 1H), 7.29-7.43 (m, 80H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 ( s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1018

Tris [6- (2-methyleneoxyG1-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (2-methyleneoxyG1-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (d, 1H ), 7.30-7.49 (m, 11H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1019

Tris [6- (3-methyleneoxyG1-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (3-methyleneoxyG1-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

1 H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.77 (d, 1H), 7.61 (m, 2H), 7.59 (t, 1H), 7.52 (s, 1H), 7.30-7.49 (m, 11H), 7.27 (t, 1H), 7.19 (t, 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1020

Tris [6- (4-methyleneoxyG1-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (4-methyleneoxyG1-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.77 (d, 1H), 7.62 (m, 2H), 7.59 (t, 1H), 7.52 (t, 1H), 7.88 (d, 2H ), 7.30-7.49 (m, 11H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1021

Tris [6- (2-methyleneoxyG2-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (2-methyleneoxyG2-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.77 (d, 1H), 7.61 (m, 2H), 7.59 (t, 1H), 7.52 (t, 1H), 7.88 (d, 2H ), 7.30-7.49 (m, 11H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1022

Tris [6- (3-methyleneoxyG2-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (3-methyleneoxyG2-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.62 (m, 2H), 7.59 (t, 1H), 7.52 (s, 1H), 7.27-7.47 (m, 22H), 7.19 (t , 1H), 6.79 (d, 1H), 6.86 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1023

Tris [6- (4-methyleneoxyG2-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (4-methyleneoxyG2-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.77 (d, 1H), 7.72 (m, 2H), 7.59 (t, 1H), 7.52 (t, 1H), 7.88 (d, 2H ), 7.45 (t, 1H), 7.27-7.47 (m, 20H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t , 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1024

Tris [6- (2-methyleneoxyG3-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (2-methyleneoxyG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.27-7.41 (m, 40H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1025

Tris [6- (3-methyleneoxyG3-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (3-methyleneoxyG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.77 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H ), 7.45 (t, 1H), 7.27-7.41 (m, 41H), 7.19 (t, 1H), 6.86 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1026

Tris [6- (4-methyleneoxyG3-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (4-methyleneoxyG3-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.27-7.41 (m, 40H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.54 (t , 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1027

Tris [6- (2-methyleneoxyG4-phenyl) -phenanthridinein] iridium (III)

Tris [6- (2-methyleneoxyG4-phenyl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 81H), 7.19 (t, 1H), 6.93 (t, 1H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1028

Tris [6- (3-methyleneoxyG4-phenyl) -phenanthridineinto] iridium (III)

Tris [6- (3-methyleneoxyG4-phenyl) -phenanthridineato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.93 (d, 1H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (s, 1H), 7.45 (t, 1H ), 7.29-7.43 (m, 80H), 7.27 (t, 1H), 7.19 (t, 1H), 6.86 (d, 1H), 6.79 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1029

Tris [6- (4-methyleneoxyG4-phenyl) -phenanthridiyneto] iridium (III)

Tris [6- (4-methyleneoxyG4-phenyl) -phenanthridineato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 22]

¹ H-NMR (CDCl ₃ ): δ 7.90 (d, 1H), 7.78 (d, 2H), 7.72 (m, 2H), 7.61 (t, 1H), 7.59 (t, 1H), 7.52 (t, 1H ), 7.45 (t, 1H), 7.29-7.43 (m, 81H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1030

Tris [6- (2 ', 3' or 4'-methoxy-biphenyl-4-yl) -phenantridiyneto] iridium (III)

Tris [6- (2 ', 3' or 4'-Methoxy-biphenyl-4-yl) -phenanthridineato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

6- (4'-methoxy-biphenyl-4-yl) -phenanthtridyne: ¹ H-NMR (CDCl ₃ ): δ 7.95 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.37 (d, 2H), 6.83 (d, 2H) ), 3.82 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1031

Tris [6- (2'-OG1-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (2'-OG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

6- (2'-OG1-biphenyl-4-yl) -phenanthtridyne: ¹ H-NMR (CDCl ₃ ): δ 7.91 (m, 3H), 7.87 (d, 1H), 7.74 (d, 1H ), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1032

Tris [6- (3'-OG1-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (3'-OG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H ), 7.43 (t, 1H), 7.30-7.49 (m, 11H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1033

Tris [6- (4'-OG1-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (4'-OG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 7.95 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s , 4H), 4.62 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1034

Tris [6- (2'-OG2-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (2'-OG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (d, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 22H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1035

Tris [6- (3'-OG2-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (3'-OG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.07 (d, 2H), 7.77 (d, 1H), 7.74 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H ), 7.29-7.43 (m, 22H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (m, 3H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1036

Tris [6- (4'-OG2-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (4'-OG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 7.95 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1037

Tris [6- (2'-OG3-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (2'-OG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H ), 7.29-7.43 (m, 42H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1038

Tris [6- (3'-OG3-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (3'-OG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H), 7.50 (t, 1H ), 7.29-7.43 (m, 42H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65-6.52 (m, 21H), 5.09 ( s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1039

Tris [6- (4'-OG3-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (4'-OG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 43H), 6.83 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1040

Tris [6- (2'-OG4-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (2'-OG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 82H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.65-6.48 (m, 45H), 5.09 ( s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1041

Tris [6- (3'-OG4-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (3'-OG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 82H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.65-6.48 ( m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1042

Tris [6- (4'-OG4-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (4'-OG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.29-7.43 (m, 83H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 ( s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 660 nm.

Example 1043

Tris [6- (2'-methyleneoxyG1-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2'-methyleneoxyG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1044

Tris [6- (3'-methyleneoxyG1-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (3'-methyleneoxyG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.30-7.49 (m, 12H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1045

Tris [6- (4'-methyleneoxyG1-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4'-methyleneoxyG1-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.30-7.49 (m, 13H), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1046

Tris [6- (2'-methyleneoxyG2-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2'-methyleneoxyG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (d, 1H), 7.27-7.47 (m, 22H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s , 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1047

Tris [6- (3'-methyleneoxyG2-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (3'-methyleneoxyG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (d, 1H), 7.27-7.47 (m, 22H), 7.17 (t, 1H), 7.06 (d, 1H), 7.02 (d, 2H), 6.98 (s, 1H), 6.71 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s , 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1048

Tris [6- (4'-methyleneoxyG2-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4'-methyleneoxyG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (m, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.47 (m, 22H), 6.83 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1049

Tris [6- (2'-methyleneoxyG3-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2'-methyleneoxyG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ ¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 ( t, 1H), 7.57 (m, 3H), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1050

Tris [6- (3'-methyleneoxyG3-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (3'-methyleneoxyG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s , 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1051

Tris [6- (4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.43 (d, 1H), 7.27-7.41 (m, 42H), 6.83 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1052

Tris [6- (2'-methyleneoxyG4-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2'-methyleneoxyG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (d, 1H), 7.29-7.43 (m, 83H), 7.06 (t, 1H), 6.88 (t, 1H), 6.80 (t, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm

Example 1053

Tris [6- (3'-methyleneoxyG4-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (3'-methyleneoxyG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.06 (d, 2H), 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.43 (d, 1H), 7.29-7.43 (m, 81H), 7.17 (t, 1H), 7.06 (d, 1H), 6.98 (s, 1H), 6.71 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 ( d, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1054

Tris [6- (4'-methyleneoxyG4-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4'-methyleneoxyG4-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 23]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (m, 3H ), 7.50 (t, 1H), 7.43 (d, 1H), 7.29-7.43 (m, 83H), 6.83 (d, 2H), 6.62-6.67 (m, 43H), 6.57 (d, 2H, J = 2.4 ), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 655 nm.

Example 1055

Tris [6- (5-methoxy-thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (5-methoxy-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.43 (t, 1H), 6.53 (d, 1H), 6.06 (d, 1H), 3.85 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1056

Tris [6- (5-OG1-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG1-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.30-7.49 (m, 11H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.53 (d, 1H), 6.06 (d, 1H), 5.02 (s , 4H), 4.62 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1057

Tris [6- (5-OG2-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG2-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 21H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.53 (d, 1H), 6.05 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1058

Tris [6- (5-OG3-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG3-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 41H), 6.65-6.52 (m, 21H), 6.03 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1059

Tris [6- (5-OG4-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG4-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 81H), 6.65-6.48 (m, 45H), 6.53 (d, 1H), 6.11 (d, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 ( s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1060

Tris [6- (5-methyleneoxyG1-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG1-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.43 (t, 1H), 7.30-7.49 (m, 11H), 6.55 (t, 1H, J = 2.1), 6.53 (d, 1H), 6.06 (d, 1H), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1061

Tris [6- (5-methyleneoxyG1-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG1-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.43 (t, 1H), 7.30-7.49 (m, 11H), 6.55 (t, 1H, J = 2.1), 6.53 (d, 1H), 6.04 (d, 1H), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1062

Tris [6- (5-methyleneoxyG2-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG2-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.43 (t, 1H), 7.27-7.47 (m, 21H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (m, 2H), 6.0 (d, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1063

Tris [6- (5-methyleneoxyG3-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG3-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.43 (t, 1H), 7.27-7.41 (m, 41H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (m, 3H), 6.07 (d, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1064

Tris [6- (5-methyleneoxyG4-thiophen-2-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG4-thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 24]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.74 (d, 1H), 7.71 (d, 1H), 7.63 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 81H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.53 (d, 1H), 6.0 (d, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1065

Tris [6- {5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

Tris [6- {5- (4-methoxy-phenyl) -thiophen-2-yl} -phenanthtridiinto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.37 (d, 2H) ), 7.03 (d, 2H), 6.86 (d, 2H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1066

Tris [6- {5- (2-OG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-OG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.78 (d, 1H), 7.59 (t, 1H ), 7.57 (d, 1H), 7.37 (d, 1H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 7.29-7.44 (m, 10H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1067

Tris [6- {5- (3-OG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-OG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.67 (t, 1H), 7.44 (t, 1H), 7.73 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 7.29-7.44 (m, 10H), 7.20- 7.23 (m, 1H), 7.00 (m, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1068

Tris [6- {5- (4-OG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-OG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.67 (t, 1H), 7.73 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.44 (m, 14H), 7.20-7.23 (m, 1H), 7.03 (d, 2H), 6.86 (d, 2H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H) , J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1069

Tris [6- {5- (2-OG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-OG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.29-7.43 (m , 22H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1070

Tris [6- {5- (3-OG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-OG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 21H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.71 (d, 2H, J = 2.1 ), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1071

Tris [6- {5- (4-OG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-OG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 23H), 7.03 (d, 2H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1072

Tris [6- {5- (2-OG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [{5- (2-OG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H), 7.57 (t, 1H ), 7.29-7.43 (m, 42H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1073

Tris [6- {5- (3-OG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-OG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.29-7.43 (m, 41H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1074

Tris [6- {5- (4-OG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-OG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 42H), 7.03 (d, 2H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1075

Tris [6- {5- (2-OG4-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-OG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H), 7.57 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 5.09 ( s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1076

Tris [6- {5- (3-OG4-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-OG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 80H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.65- 6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1076

Tris [6- {5- (4-OG4-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-OG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 82H), 7.03 (d, 2H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 ( s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 680 nm

Example 1077

Tris [6- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H), 7.57 (t, 1H ), 7.30-7.49 (m, 13H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.55 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1078

Tris [6- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.30-7.49 (m, 12H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.55 (t, 1H), 5.02 ( s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 675 nm.

Example 1079

Tris [6- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.37 (d, 2H), 7.30-7.49 (m, 12H), 7.03 (d, 2H), 6.86 (d, 2H), 6.55 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1080

Tris [6- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H), 7.57 (t, 1H ), 7.27-7.47 (m, 23H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J) = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1081

Tris [6- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.27-7.47 (m, 22H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.67 (d, 4H, J = 2.1 ), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1082

Tris [6- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.27-7.47 (m, 24H), 7.03 (d, 2H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t , 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1083

Tris [6- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.59 (t, 1H), 7.57 (t, 1H ), 7.44 (t, 1H), 7.27-7.41 (m, 42H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1084

Tris [6- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.27-7.41 (m, 41H), 7.22 (t, 1H), 7.05 (d, 2H), 6,99 (s, 1H), 6.75 (d, 1H), 6.67 ( d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1085

Tris [6- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.27-7.41 (m, 43H), 7.03 (d, 2H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1086

Tris [6-5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl-phenanthtridieto] iridium (III)

Tris [6- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.59 (t, 1H), 7.67 (t, 1H), 7.57 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 82H), 7.11 (t, 1H), 6.89 (t, 1H), 6.83 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1087

Tris [6- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 81H), 7.22 (t, 1H), 7.05 (d, 2H), 6.99 (s, 1H), 6.75 (d, 1H), 6.62-6.67 ( m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1088

Tris [6- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 25]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.50 (t, 1H ), 7.44 (t, 1H), 7.29-7.43 (m, 83H), 7.03 (d, 2H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H) , J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1089

Tris [6- {7- (4-methoxy-phenyl) -9H-floren-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {7- (4-Methoxy-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (s, 1H), 7.73 (m, 3H ), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.44 (t, 1H), 7.37 (d, 2H), 6.86 (d, 2H) , 3.87 (d, 2 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1090

Tris [6- {7- (4-OG1-phenyl) -9H-floren-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {7- (4-OG1-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.44 (m, 13H), 6.86 (m, 3H), 6.72 (m, 4H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H), 3.87 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1091

Tris [6- {7- (4-OG2-phenyl) -9H-floren-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {7- (4-OG2-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.29-7.43 (m, 23H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 ( s, 4H), 3.87 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1092

Tris [6- {7- (4-OG3-phenyl) -9H-floren-2-yl} -phenanthridiyneto] iridium (III)

Tris [6- {7- (4-OG3-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.44 (t, 1H), 7.29-7.43 (m, 42H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.87 (d, 2 H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1093

Tris [6- {7- (4-OG4-phenyl) -9H-floren-2-yl} -phenantridiyneto] iridium (III)

Tris [6- {7- (4-OG4-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.12 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.44 (t, 1H), 7.29-7.43 (m, 82H), 6.86 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H), 3.87 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 695 nm.

Example 1094

Tris [6- {7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl} -phenanthridinein] iridium (III)

Tris [6- {7- (4-methyleneoxyG1-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.11 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.30-7.49 (m, 14H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.87 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 690 nm

Example 1095

Tris [6- {7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl} -phenanthridineinto] iridium (III)

Tris [6- {7- (4-methyleneoxyG2-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.01 (m, 2H), 7.93 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.30-7.49 (m, 14H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H), 3.87 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 690 nm

Example 1096

Tris [6- {7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl} -phenanthridinein]] iridium (III)

Tris [6- {7- (4-methyleneoxyG3-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.01 (m, 2H), 7.83 (d, 1H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H ), 7.71 (d, 1H), 7.67 (t, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.27-7.41 (m, 41H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s , 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1097

Tris [6-7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl-phenantridiyneto] iridium (III)

Tris [6- {7- (4-methyleneoxyG4-phenyl) -9H-fluoren-2-yl} -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 26]

¹ H-NMR (CDCl ₃ ): δ 8.04 (m, 2H), 7.90 (d, 1H), 7.87 (d, 1H), 7.77 (m, 2H), 7.73 (d, 1H), 7.71 (d, 1H ), 7.67 (d, 1H), 7.61 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.27-7.41 (m, 41H), 7.29-7.43 (m, 81H), 6.86 ( d, 2H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2 H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1098

Tris [6- (6-methoxy-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-methoxy-benzo [b] thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (s, 1H), 7.31 (m, 2H), 6.81 (d, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1099

Tris [6- (6-OG1-Benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-OG1-benzo [b] thiophen-2-yl) -phenanthridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.77 (m, 2H), 7.71 (m, 2H), 7.57 (t, 1H), 7.62 (t, 1H), 7.51 (t, 1H ), 7.29-7.44 (m, 13H), 6.86 (d, 1H), 6.81 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.71 (d, 2H, J = 2.1), 6.57 (t , 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1100

Tris [6- (6-OG2-Benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-OG2-benzo [b] thiophen-2-yl) -phenanthridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.29-7.43 (m, 23H), 6.81 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1101

Tris [6- (6-OG3-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-OG3-benzo [b] thiophen-2-yl) -phenanthridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 41H), 6.81 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 ( s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1102

Tris [6- (6-OG4-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-OG4-benzo [b] thiophen-2-yl) -phenanthridinato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 81H), 6.81 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 ( s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 690 nm.

Example 1103

Tris [6- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (s, 1H), 7.31 (m, 2H), 7.20-7.39 (m, 11H), 6.81 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1104

Tris [6- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (m, 2H), 7.17-7.37 (m, 21H), 6.81 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (t, 2H, J = 2.4), 6.51 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1105

Tris [6- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.41 (m, 2H), 7.17-7.31 (m, 41H), 6.81 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d , 2H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1106

Tris [6- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -phenanthridiyneto] iridium (III)

Tris [6- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 27]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.51 (t, 1H), 7.29-7.43 (m, 82H), 6.81 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1107

Tris [6- (4-methoxy-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (4-methoxy-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H ), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.32 (t, 1H), 6.71 (d, 1H), 3.73 (s, 3H) .

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1108

Tris [6- (4-OG1-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG1-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

1 H-NMR (CDCl 3): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 1H), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.19-7.34 (m, 11H), 6.71 (d, 1H), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1109

Tris [6- (4-OG2-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG2-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H ), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 21H), 6.71 (m, 3H), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1110

Tris [6- (4-OG3-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG3-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.72 (m, 1H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 41H), 6.71 (d, 1H), 6.65-6.52 (m, 21H), 5.09 ( s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1111

Tris [6- (4-OG4-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (4-OG4-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.32 (t, 1H), 7.87 (d, 1H), 7.77 (m, 2H ), 7.71 (d, 1H), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 80H), 6.71 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 32H), 5.01 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1112

Tris [6- (4-methyleneoxyG1-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4-methyleneoxyG1-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.41 (t, 1H), 7.87 (d, 1H), 7.77 (d, 1H ), 7.71 (m, 2H), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (t, 1H), 7.21-7.39 (m, 11H), 6.71 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1113

Tris [6- (4-methyleneoxyG2-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4-methyleneoxyG2-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H ), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.17-7.37 (m, 21H), 6.71 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.51 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1114

Tris [6- (4-methyleneoxyG3-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4-methyleneoxyG3-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.71 (m, 2H ), 7.61 (t, 1H), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.17-7.34 (m, 41H), 6.71 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1115

Tris [6- (4-methyleneoxyG4-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (4-methyleneoxyG4-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 28]

¹ H-NMR (CDCl ₃ ): δ 8.21 (d, 1H), 8.11 (d, 1H), 8.01 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.61 (t, 1H ), 7.56 (t, 1H), 7.50 (t, 1H), 7.41 (m, 2H), 7.19-7.33 (m, 81H), 6.71 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1116

Tris [6- (5-methoxy-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methoxy-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.21 (d, 1H), 6.66 (d, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1117

Tris [6- (5-OG1-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG1-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.42 (m, 2H), 7.19-7.34 (m, 11H), 6.72 (d, 2H, J = 2.1), 6.71 (d, 2H, J) = 2.4), 6.66 (d, 1H), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1118

Tris [6- (5-OG2-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG2-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (d, 1H), 7.42 (m, 2H), 7.19-7.13 (m, 21H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.66 (d , 1H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1119

Tris [6- (5-OG3-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG3-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.19-7.33 (m, 41H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1120

Tris [6- (5-OG4-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-OG4-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.19-7.33 (m, 81H), 6.67 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 ( s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 680 nm.

Example 1121

Tris [6- (5-methyleneoxyG1-naphthalene-1-yl) -phenanthridineinto] iridium (III)

Tris [6- (5-methyleneoxyG1-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.20-7.39 (m, 11H), 6.66 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2 H), 4.53 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1122

Tris [6- (5-methyleneoxyG2-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (5-methyleneoxyG2-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.17-7.37 (m, 21H), 6.67 (m, 5H), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1123

Tris [6- (5-methyleneoxyG3-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (5-methyleneoxyG3-naphthalen-1-yl) -phenanthridinato] iridium (II)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.61 (t, 1H), 7.57 (t, 1H ), 7.50 (t, 1H), 7.42 (m, 2H), 7.21 (t, 1H), 7.17-7.32 (m, 41H), 6.69 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s , 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1124

Tris [6- (5-methyleneoxyG4-naphthalene-1-yl) -phenanthridiyneto] iridium (III)

Tris [6- (5-methyleneoxyG4-naphthalen-1-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 29]

¹ H-NMR (CDCl ₃ ): δ 8.23 (m, 2H), 8.21 (d, 1H), 7.87 (m, 2H), 7.74 (d, 1H), 7.70 (d, 1H), 7.61 (t, 1H ), 7.57 (t, 1H), 7.50 (t, 1H), 7.42 (m, 2H), 7.19-7.33 (m, 82H), 6.66 (d, 1H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 670 nm.

Example 1125

Tris [6- (2, 3, 6-trifluoro-4'-methoxy-biphenyl-4-yl) -phenantridiyneto] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-methoxy-biphenyl-4-yl) -phenanthridinato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H), 7.52 (s, 1H ), 7.51 (d, 1H), 7.41 (t, 1H), 7.38 (d, 2H), 6.86 (d, 2H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1126

Tris [6- (2, 3, 6-trifluoro-4'-OG1-biphenyl-4-yl) -phenanthridinein]] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-OG1-biphenyl-4-yl) -phenanthridinato]

iridium (III). [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.21-7.35 (m, 13H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1127

Tris [6- (2, 3, 6-trifluoro-4'-OG2-biphenyl-4-yl) -phenanthridinein]] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-OG2-biphenyl-4-yl) -phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H), 7.52 (s, 1H ), 7.51 (t, 1H), 7.19-7.33 (m, 23H), 6.86 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1128

Tris [6- (2, 3, 6-trifluoro-4'-OG3-biphenyl-4-yl) -phenanthridinein]] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-OG3-biphenyl-4-yl) -phenanthridinato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H), 7.52 (s, 1H ), 7.51 (t, 1H), 7.19-7.33 (m, 43H), 6.86 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 ( s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1129

Tris [6- (2, 3, 6-trifluoro-4'-OG4-biphenyl-4-yl) -phenanthridineinto] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-OG4-biphenyl-4-yl) -phenanthridinato]

Synthesis and purification were carried out by a similar method to the synthesis of iridium (III) complexes before iridium (III). [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H), 7.52 (s, 1H ), 7.51 (t, 1H), 7.19-7.33 (m, 83H), 6.65-6.48 (m, 45H), 6.86 (d, 2H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 ( s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1130

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -phenantridiyneto] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl)

phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.50 (t, 1H), 7.41 (t, 1H), 7.20-7.39 (m, 12H), 6.86 (d, 2H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1131

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl-phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.41 (t, 1H), 7.38 (d, 2H), 7.17-7.37 (m, 21H), 6.86 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (t, 2H, J = 2.4), 6.50 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s , 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1132

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -phenanthridiyneto] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl)-

phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.70 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H ), 7.52 (s, 1H), 7.51 (t, 1H), 7.41 (t, 1H), 7.38 (d, 2H), 7.17-7.31 (m, 41H), 6.86 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (t, 4H, J = 2.4), 6.51 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d , 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1133

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -phenanthridinein]] iridium (III)

Tris [6- (2, 3, 6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl-phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 30]

¹ H-NMR (CDCl ₃ ): δ 8.13 (d, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.62 (t, 1H), 7.57 (t, 1H), 7.52 (s, 1H ), 7.51 (t, 1H), 7.41 (d, 1H), 7.38 (d, 2H), 7.19-7.33 (m, 81H), 6.86 (d, 2H), 6.62-6.67 (m, 43H, J = 2.1 ), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1134

Tris [2- (2, 3 or 4-methoxy-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2, 3 or 4-methoxy-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

2- (4-methoxy-phenyl) -benzothiazole: ¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.38 (d, 2H), 6.90 (d, 2H), 3.84 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1135

Tris [2- (2-OG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-OG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.24-7.38 (m, 11H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1136

Tris [2- (3-OG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-OG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.23-7.39 (m, 11H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1137

Tris [2- (4-OG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.34 (m, 12H), 6.90 (d, 2H), 6.71 (d, 2H, J = 2.1) 6.72 (d, 2H, J = 2.4), 6.57 (t, 1H, J = 2.4), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1138

Tris [2- (2-OG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-OG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.54 (m, 2H), 7.22-7.33 (m, 21H), 7.12 (d, 1H), 6.89 (t, 1H), 6.82 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1139

Tris [2- (3-OG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-OG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.35 (m, 20H), 7.18 (t, 1H), 7.06 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1140

Tris [2- (4-OG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.34 (m, 22H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1142

Tris [2- (2-OG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-OG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.22-7.33 (m, 41H), 7.12 (t, 1H), 6.89 (t, 1H), 6.82 (d , 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1143

Tris [2- (3-OG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-OG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.34 (m, 40H), 7.18 (d, 1H), 7.06 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1144

Tris [2- (4-OG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.19-7.33 (m, 42H), 6.90 (d, 2H), 6.65-6.52 (m, 21H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1145

Tris [2- (2-OG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-OG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.19-7.33 (m, 81H), 7.12 (t, 1H), 6.89 (t, 1H), 6.82 (d , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1146

Tris [2- (3-OG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-OG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.21-7.33 (m, 80H), 7.18 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 4.95-4.92 (m, 28H), 5.01 (s, 32H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1147

Tris [2- (4-OG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.21-7.33 (m, 82H), 6.90 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1148

Tris [2- (2-methyleneoxyG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-methyleneoxyG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.20-7.38 (m, 11H), 7.12 (t, 1H), 6.89 (t , 1H), 6.82 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1149

Tris [2- (3-methyleneoxyG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-methyleneoxyG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.21-7.39 (m, 11H), 7.18 (t, 1H), 7.06 (d , 1H), 6.99 (s, 1H), 6.73 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1150

Tris [2- (4-methyleneoxyG1-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG1-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.30-7.49 (m, 12H), 6.90 (d, 2H), 6.55 (t , 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1151

Tris [2- (2-methyleneoxyG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-methyleneoxyG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (t, 1H), 6.89 (t, 1H), 6.82 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1152

Tris [2- (3-methyleneoxyG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-methyleneoxyG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.17-7.37 (m, 21H), 7.18 (t, 1H), 7.06 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1153

Tris [2- (4-methyleneoxyG2-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG2-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.17-7.37 (m, 22H), 6.90 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 ( s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1154

Tris [2- (2-methyleneoxyG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-methyleneoxyG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.31 (m, 41H), 7.12 (t, 1H), 6.89 (d, 1H), 6.82 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1155

Tris [2- (3-methyleneoxyG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-methyleneoxyG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.21-7.31 (m, 41H), 7.18 (d, 1H), 7.06 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1156

Tris [2- (4-methyleneoxyG3-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG3-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 6.90 (d, 2H), 7.17-7.31 (m, 41H), 6.90 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1157

Tris [2- (2-methyleneoxyG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (2-methyleneoxyG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.19-7.33 (m, 81H), 7.12 (d, 1H), 6.89 (t, 1H), 6.82 (d , 1H), 6.62-6.67 (m, 43H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1158

Tris [2- (3-methyleneoxyG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (3-methyleneoxyG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 8.13 (d, 1H), 7.56 (m, 2H), 7.20-7.33 (m, 80H), 7.18 (d, 1H), 6.99 (s , 1H), 6.73 (d, 1H), 6.52-6.57 (m, 43H, J = 2.1), 6.51 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1159

Tris [2- (4-methyleneoxyG4-phenyl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG4-phenyl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 32]

¹ H-NMR (CDCl ₃ ): δ 8.24 (d, 1H), 7.56 (m, 2H), 7.19-7.33 (m, 82H), 6.90 (d, 2H), 6.62-6.67 (m, 43H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1160

Tris [2- (2 ', 3' or 4'-methoxy-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2 ', 3' or 4'-methoxy-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

Tris [2- (2'-methoxy-biphenyl-4-yl) -benzothiazoleto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.37 (d, 1H), 7.1 (t, 1H), 6.83 (m, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Tris [2- (3'-methoxy-biphenyl-4-yl) -benzothiazoleto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.21 (t, 1H), 7.04 (m, 1H), 6.73 (d, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Tris [2- (4'-methoxy-biphenyl-4-yl) -benzothiazoleto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 6H), 7.37 (s, 1H), 6.83 (d, 2H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1161

Tris [2- (2'-OG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-OG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.12 (t, 1H), 6.83 (m , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1162

Tris [2- (3'-OG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-OG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 7.04 (m , 1H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1163

Tris [2- (4'-OG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-OG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 6.83 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1164

Tris [2- (2'-OG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-OG2-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.63 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 21H), 7.12 (t, 1H), 6.83 (m , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1165

Tris [2- (3'-OG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-OG2-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 7.04 (m , 1H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1166

Tris [2- (4'-OG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-OG2-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 21H), 6.83 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1167

Tris [2- (2'-OG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-OG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.63 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 41H), 7.1 (t, 1H), 6.83 (m , 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1168

Tris [2- (3'-OG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-OG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.63 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 7.04 (m , 1H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1169

Tris [2- (4'-OG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-OG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 41H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1170

Tris [2- (2'-OG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-OG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.11 (t, 1H), 6.83 (m , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1171

Tris [2- (3'-OG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-OG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.6 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 7.04 (m , 1H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1172

Tris [2- (4'-OG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-OG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.63 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1173

Tris [2- (2'-methyleneoxyG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Trsi [2- (2'-methyleneoxyG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.12 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1174

Tris [2- (3'-methyleneoxyG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-methyleneoxyG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.22 (t, 1H), 7.02 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1175

Tris [2- (4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.30-7.49 (m, 11H), 7.12 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1176

Tris [2- (2'-methyleneoxyG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-methyleneoxyG2-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.61 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 21H), 7.12 (m, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm

Example 1177

Tris [2- (3'-methyleneoxyG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-methyleneoxyG2-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 21H), 7.22 (t, 1H), 7.02 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1178

Tris [2- (4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazoato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.27-7.47 (m, 21H), 7.12 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1179

Tris [2- (2'-methyleneoxyG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-methyleneoxyG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.62 (d, 1H), 7.55 (m, 6H), 7.27-7.41 (m, 41H), 7.12 (m, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm

Example 1180

Tris [2- (4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.82 (d, 1H), 7.55 (m, 6H), 7.27-7.41 (m, 41H), 7.12 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm

Example 1181

Tris [2- (2'-methyleneoxyG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2'-methyleneoxyG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.0 (d, 1H), 7.8 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.12 (m, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1182

Tris [2- (3'-methyleneoxyG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (3'-methyleneoxyG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.2 (t, 1H), 7.02 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1183

Tris [2- (4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 33]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 6H), 7.29-7.43 (m, 81H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1184

Tris [2- (5-methoxy-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methoxy-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 6.0 (s, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1185

Tris [2- (5-OG1-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG1-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 6.65 (d, 2H, J = 3.9) 6.55 (t, 1H, J = 2.1), 6.0 (s, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm

Example 1186

Tris [2- (5-OG2-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG2-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 20H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.0 (s, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1187

Tris [2- (5-OG3-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG3-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 22H), 6.0 (s, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1188

Tris [2- (5-OG4-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG4-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 6.65-6.48 (m, 45H), 6.0 (s, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1189

Tris [2- (5-methyleneoxyG1-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG1-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 6.7 (s, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm

Example 1190

Tris [2- (5-methyleneoxyG2-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG2-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.0 (d, 1H), 7.8 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 20H), 6.72 (s, 1H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.5 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1191

Tris [2- (5-methyleneoxyG3-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG3-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), λ 7.27-7.41 (m, 40H), 6.72 (s, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1192

Tris [2- (5-methyleneoxyG4-thiophen-2-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG4-thiophen-2-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 34]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 6.72 (s, 1H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1193

Tris [2- {5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

Tris [2- {5- (2-methoxy-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.15 (t, 1H), 7.02 (d, 2H), 6.83 (m, 2H ), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Tris [2- {5- (3-methoxy-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.21 (t, 1H), 7.02 (m, 3H), 6.73 (d, 1H ), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Tris [2- {5- (4-methoxy-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

¹ H-NMR (CDCl ₃ ): δ 8.23 (d, 1H), 8.12 (d, 1H), 7.55 (m, 2H), 7.37 (d, 2H), 7.03 (s, 1H), 6.83 (d, 2H ), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1194

Tris [2- {5- (2-OG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-OG1-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 7.12 (t, 1H), 7.03 (d , 2H), 6.83 (m, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1195

Tris [2- {5- (3-OG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-OG1-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 7.02 (m , 3H), 6.73 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1196

Tris [2- {5- (4-OG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-OG1-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.85 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.04 (d, 2H), 6.83 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1197

Tris [2- {5- (2-OG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-OG2-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 20H), 7.12 (t, 1H), 7.0 (d , 2H), 6.83 (m, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1198

Tris [2- {5- (3-OG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-OG2-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 7.02 (m , 3H), 6.73 (d, 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1199

Tris [2- {5- (4-OG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-OG2-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 21H), 7.02 (d, 2H), 6.83 (d , 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1200

Tris [2- {5- (2-OG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-OG3-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 41H), 7.13 (t, 1H), 7.04 (s , 1H), 6.83 (m, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1201

Tris [2- {5- (3-OG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-OG3-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 7.02 (m , 3H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1202

Tris [2- {5- (4-OG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-OG3-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 41H), 7.03 (d, 2H), 6.83 (d , 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1203

Tris [2- {5- (2-OG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-OG4-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.14 (t, 1H), 7.02 (s , 1H), 6.83 (m, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1204

Tris [2- {5- (3-OG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-OG4-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 7.02 (m , 3H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1205

Tris [2- {5- (4-OG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-OG4-phenyl) -thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.04 (s, 1H), 6.83 (d , 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1206

Tris [2- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (m, 3H), 7.01 (s , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1207

Tris [2- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.24 (t, 1H), 7.05 (m , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1208

Tris [2- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 7.06 (s , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1209

Tris [2- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (m, 3H), 7.03 (s , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1210

Tris [2- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 22H), 7.25 (t, 1H), 7.03 (m , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1211

Tris [2- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 7.02 (s , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1212

Tris [2- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.12 (m, 3H), 7.04 (s , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1213

Tris [2- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.82 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 42H), 7.21 (t, 1H), 7.03 (m , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1214

Tris [2- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.84 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 7.03 (s , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1215

Tris [2- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (m, 3H), 7.04 (s , 1H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1216

Tris [2- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.22 (t, 1H), 7.03 (m , 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1217

Tris [2- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 35]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 7.04 (s , 1H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H ).

λ _em (CH ₂ Cl ₂ ) = 580 nm.

Example 1218

Tris [2- {7- (4-methoxy-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-methoxy-phenyl) -9H-fluoren-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.82 (d, 1H), 7.94 (d, 2H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 1H ), 7.37 (d, 2H), 6.83 (d, 2H), 3.87 (s, 2H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1219

Tris [2- {7- (4-OG1-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-OG1-phenyl) -9H-fluoren-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.93 (d, 2H), 7.82 (d, 1H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.30-7.49 (m, 11H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s , 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1220

Tris [2- {7- (4-OG2-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-OG2-phenyl) -9H-fluoren-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.93 (d, 2H), 7.82 (d, 1H), 7.77 (s, 2H), 7.63 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 21H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1221

Tris [2- {7- (4-OG3-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-OG3-phenyl) -9H-fluoren-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.93 (d, 2H), 7.82 (d, 1H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 41H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 ( s, 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1222

Tris [2- {7- (4-OG4-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-OG4-phenyl) -9H-fluoren-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.93 (d, 2H), 7.83 (d, 1H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 81H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95- 4.92 (m, 28 H), 3.87 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1223

Tris [2- {7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-methyleneoxyG1-phenyl) -9H-fluoren-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. . [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.94 (d, 2H), 7.83 (d, 1H), 7.77 (s, 2H), 7.61 (d, 2H), 7.55 (m, 2H ), 7.30-7.49 (m, 11H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s , 2H), 4.53 (s, 2H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1224

Tris [2- {7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-methyleneoxyG2-phenyl) -9H-fluoren-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.00 (d, 1H), 7.92 (d, 2H), 7.81 (d, 1H), 7.77 (s, 2H), 7.61 (d, 2H), 7.55 (m, 2H ), 7.27-7.47 (m, 21H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4) , 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1225

Tris [2- {7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-methyleneoxyG3-phenyl) -9H-fluoren-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.93 (d, 2H), 7.82 (d, 1H), 7.77 (s, 2H), 7.61 (d, 2H), 7.55 (m, 2H ), 7.27-7.41 (m, 41H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1226

Tris [2- {7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {7- (4-methyleneoxyG4-phenyl) -9H-fluoren-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. . [Formula 36]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.92 (d, 2H), 7.84 (d, 1H), 7.77 (s, 2H), 7.62 (d, 2H), 7.55 (m, 2H ), 7.29-7.43 (m, 81H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 570 nm.

Example 1227

Tris [2- {6-methoxy-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-methoxy-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.73 (d, 1H), 7.55 (m, 2H), 7.32 (s, 1H), 6.8 (d, 1H ), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 1228

Tris [2- {6-OG1-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-OG1-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.04 (d, 1H), 7.83 (d, 1H), 7.73 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 6.83 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 1229

Tris [2- {6-OG2-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-OG2-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 21H), 6.83 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 1230

Tris [2- {6-OG3-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-OG3-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 41H), 6.83 (d , 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 635 nm

Example 1231

Tris [2- {6-OG4-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-OG4-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.74 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 6.8 (d , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 635 nm.

Example 1232

Tris [2- {6-methyleneoxyG1-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-methyleneoxyG1-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.71 (m, 2H), 7.55 (m, 2H), 7.30-7.49 (m, 10H), 7.13 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 630 nm

Example 1233

Tris [2-6-methyleneoxyG2-3a, 7b-dihydro-benzo [b] thiophen-2-yl-benzothiazoleto] iridium (III)

Tris [2-6-methyleneoxyG2-3a, 7b-dihydro-benzo [b] thiophen-2-yl-benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (d, 1H), 7.73 (m, 2H), 7.55 (m, 2H), 7.27-7.47 (m, 20H), 7.14 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 630 nm

Example 1234

Tris [2- {6-methyleneoxyG3-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-methyleneoxyG3-3a, 7b-dihydro-benzo [b] thiophen-2-yl}-

benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.73 (m, 2H), 7.55 (m, 2H), 7.27-7.41 (m, 40H), 7.13 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 1235

Tris [2- {6-methyleneoxyG4-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazoleto] iridium (III)

Tris [2- {6-methyleneoxyG4-3a, 7b-dihydro-benzo [b] thiophen-2-yl} -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 37]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.81 (d, 1H), 7.73 (m, 2H), 7.55 (m, 2H), 7.29-7.43 (m, 80H), 7.14 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 630 nm.

Example 1236

Tris [2- (4-methoxy-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-methoxy-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.03 (m, 2H), 7.82 (d, 1H), 7.72 (d, 1H), 7.55 (m, 2H), 7.42 (m, 1H), 7.32 (t, 1H ), 6.73 (d, 1 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1237

Tris [2- (4-OG1-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG1-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (m, 2H), 7.82 (d, 1H), 7.72 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 6.72 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1238

Tris [2- (4-OG2-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG2-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (m, 2H), 7.82 (d, 1H), 7.74 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 6.73 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1239

Tris [2- (4-OG3-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG3-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (m, 2H), 7.82 (d, 1H), 7.74 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 6.75 (d , 1H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1240

Tris [2- (4-OG4-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-OG4-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (m, 2H), 7.81 (d, 1H), 7.71 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 6.74 (d , 1H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 625 nm.

Example 1241

Tris [2- (4-methyleneoxyG1-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG1-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.82 (d, 1H), 7.80 (d, 1H), 7.63 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m , 12H), 7.21 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1242

Tris [2- (4-methyleneoxyG2-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG2-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.81 (d, 1H), 7.63 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m , 22H), 7.23 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1243

Tris [2- (4-methyleneoxyG3-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG3-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m , 42H), 7.23 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.52 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1244

Tris [2- (4-methyleneoxyG4-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (4-methyleneoxyG4-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 38]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.84 (d, 1H), 7.81 (d, 1H), 7.62 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m , 82H), 7.23 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1245

Tris [2- (5-methoxy-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methoxy-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (m, 2H), 7.62 (d, 1H), 7.55 (m, 2H), 7.41 (t, 1H), 7.22 (t, 1H ), 6.63 (d, 1 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1246

Tris [2- (5-OG1-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG1-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (m, 2H), 7.62 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.22 (t , 1H), 6.65 (d, 2H, J = 3.9), 6.64 (d, 1H), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1247

Tris [2- (5-OG2-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG2-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (m, 2H), 7.61 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 21H), 7.23 (t , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.62 (d, 1H), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1248

Tris [2- (5-OG3-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG3-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (m, 2H), 7.61 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 41H), 7.23 (t , 1H), 6.65-6.52 (m, 23H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1249

Tris [2- (5-OG4-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-OG4-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (m, 2H), 7.61 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.23 (t , 1H), 6.65-6.48 (m, 46H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 620 nm.

Example 1250

Tris [2- (5-methyleneoxyG1-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG1-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (m, 2H), 7.73 (d, 1H), 7.55 (m, 3H), 7.30-7.49 (m, 11H), 7.22 (t , 1H), 7.13 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1251

Tris [2- (5-methyleneoxyG2-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG2-naphthalen-1-yl) -benzothiazolato] iridum (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (m, 2H), 7.72 (d, 1H), 7.55 (m, 3H), 7.27-7.47 (m, 21H), 7.23 (t , 1H), 7.15 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.52 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1252

Tris [2- (5-methyleneoxyG3-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG3-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (m, 2H), 7.72 (d, 1H), 7.55 (m, 3H), 7.27-7.41 (m, 41H), 7.21 (t , 1H), 7.13 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1253

Tris [2- (5-methyleneoxyG4-naphthalein-1-yl) -benzothiazoleto] iridium (III)

Tris [2- (5-methyleneoxyG4-naphthalen-1-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.82 (m, 2H), 7.72 (d, 1H), 7.55 (m, 3H), 7.29-7.43 (m, 81H), 7.25 (t , 1H), 7.12 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 610 nm.

Example 1254

Tris [2- (2,3,5-trifluoro-4'-methoxy-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-methoxy-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 39]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.37 (d, 2H), 6.83 (d, 2H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1255

Tris [2- (2,3,5-trifluoro-4'-OG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-OG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 12H), 6.83 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1256

Tris [2- (2,3,5-trifluoro-4'-OG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-OG2-biphenyl-4-yl) -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 22H), 6.83 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1257

Tris [2- (2,3,5-trifluoro-4'-OG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-OG3-biphenyl-4-yl) -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 42H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1258

Tris [2- (2,3,5-trifluoro-4'-OG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-OG4-biphenyl-4-yl) -benzothiazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1259

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1260

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.83 (d, 1H), 7.55 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (d, 2H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1261

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl)-

benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.12 (d, 2H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1262

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazoleto] iridium (III)

Tris [2- (2,3,5-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 40]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.63 (d, 1H), 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1263

Tris [1- (2, 3 or 4-methoxy-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2, 3 or 4-methoxy-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

Tris [1- (2-methoxy-phenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.23 ( m, 1H), 6.84 (m, 2H) 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Tris [1- (3-methoxy-phenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.23 ( t, 1H), 6.84 (m, 2H) 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Tris [1- (4-methoxy-phenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.23 ( s, 1H), 6.84 (d, 2H), 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1264

Tris [1- (2-OG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-OG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.54 (d, 1H), 7.30-7.49 (m, 10H), 7.23 (s, 1H), 6.83 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1265

Tris [1- (3-OG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-OG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.53 (d, 1H), 7.30-7.49 (m, 10H), 7.21 (t, 1H), 6.8 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1266

Tris [1- (4-OG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.53 (d, 1H), 7.30-7.49 (m, 10H), 7.22 (s, 1H), 6.83 (d, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1267

Tris [1- (2-OG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-OG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.52 (d, 1H), 7.29-7.43 (m, 20H), 7.22 (s, 1H), 6.81 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1268

Tris [1- (3-OG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-OG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.53 (d, 1H), 7.29-7.43 (m, 20H), 7.21 (t, 1H), 6.82 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1269

Tris [1- (4-OG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 20H), 7.22 (s, 1H), 6.83 (d, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1270

Tris [1- (2-OG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-OG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.52 (d, 1H), 7.29-7.43 (m, 40H), 7.22 (m, 1H), 6.82 (m, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1271

Tris [1- (3-OG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-OG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.51 (d, 1H), 7.29-7.43 (m, 40H), 7.21 (t, 1H), 6.8 (m, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1272

Tris [1- (4-OG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.52 (d, 1H), 7.29-7.43 (m, 40H), 7.23 (s, 1H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1273

Tris [1- (2-OG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-OG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.53 (d, 1H), 7.29-7.43 (m, 80H), 7.2 (m, 1H), 6.82 (m, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1274

Tris [1- (3-OG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-OG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.29-7.43 (m, 80H), 7.21 (t, 1H), 6.83 (m, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1275

Tris [1- (4-OG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.53 (d, 1H), 7.29-7.43 (m, 80H), 7.22 (s, 1H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1276

Tris [1- (2-methyleneoxyG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-methyleneoxyG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.30-7.49 (m, 10H), 7.13 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1277

Tris [1- (3-methyleneoxyG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-methyleneoxyG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.51 (d, 1H), 7.30-7.49 (m, 10H), 7.13 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1278

Tris [1- (4-methyleneoxyG1-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG1-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.30-7.49 (m, 10H), 7.12 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1279

Tris [1- (2-methyleneoxyG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-methyleneoxyG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.53 (d, 1H), 7.27-7.47 (m, 20H), 7.13 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1280

Tris [1- (3-methyleneoxyG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-methyleneoxyG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.53 (d, 1H), 7.27-7.47 (m, 20H), 7.14 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.54 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1281

Tris [1- (4-methyleneoxyG2-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG2-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.27-7.47 (m, 20H), 7.13 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1282

Tris [1- (2-methyleneoxyG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-methyleneoxyG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.27-7.41 (m, 40H), 7.14 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1283

Tris [1- (3-methyleneoxyG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-methyleneoxyG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.65 (d, 1H), 7.53 (d, 1H), 7.27-7.41 (m, 40H), 7.14 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1284

Tris [1- (4-methyleneoxyG3-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG3-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.61 (d, 1H), 7.53 (d, 1H), 7.27-7.41 (m, 40H), 7.15 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1285

Tris [1- (2-methyleneoxyG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2-methyleneoxyG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.29-7.43 (m, 80H), 7.15 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1286

Tris [1- (3-methyleneoxyG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3-methyleneoxyG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.62 (d, 1H), 7.54 (d, 1H), 7.29-7.43 (m, 80H), 7.13 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1287

Tris [1- (4-methyleneoxyG4-phenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG4-phenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 42]

¹ H-NMR (CDCl ₃ ): δ 7.63 (d, 1H), 7.54 (d, 1H), 7.29-7.43 (m, 80H), 7.14 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 417 nm.

Example 1288

Tris [1- (2 ', 3' or 4'-methoxy-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2 ', 3' or 4'-methoxy-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

Tris [1- (2'-methoxy-biphenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.53 (d, 2H), 7.33 (d, 2H), 7.13 (t, 1H), 6.84 (m, 2H), 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 425 nm

Tris [1- (3'-methoxy-biphenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.52 (d, 2H), 7.32 (d, 1H), 7.21 (t, 1H), 7.0 (m, 2H), 6.73 (d, 1H), 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Tris [1- (4'-methoxy-biphenyl) -1H-pyrazoletto] iridium (III): ¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.52 (d, 2H), 7.37 (d, 2H), 7.31 (d, 1H), 6.83 (d, 2H), 6.46 (t, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1289

Tris [1- (2'-OG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-OG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 14H), 7.12 (t, 1H), 6.81 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1290

Tris [1- (3'-OG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-OG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 13H), 7.21 (t, 1H), 7.09 (m, 2H), 6.73 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1291

Tris [1- (4'-OG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-OG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 15H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1292

Tris [1- (2'-OG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-OG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 24H), 7.13 (t, 1H), 6.83 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1293

Tris [1- (3'-OG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-OG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 23H), 7.21 (t, 1H), 7.09 (m, 2H), 6.73 (d , 1H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1294

Tris [1- (4'-OG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-OG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 25H), 6.83 (d, 2H), 6.73 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1295

Tris [1- (2'-OG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-OG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 44H), 7.12 (t, 1H), 6.83 (m, 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1296

Tris [1- (3'-OG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-OG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 43H), 7.21 (t, 1H), 7.02 (m, 2H), 6.73 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1297

Tris [1- (4'-OG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-OG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 45H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1298

Tris [1- (2'-OG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-OG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 84H), 7.14 (t, 1H), 6.84 (m, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1299

Tris [1- (3'-OG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-OG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 83H), 7.21 (t, 1H), 7.03 (m, 2H), 6.73 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1300

Tris [1- (4'-OG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-OG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 85H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 425 nm.

Example 1301

Tris [1- (2'-methyleneoxyG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-methyleneoxyG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 14H), 7.13 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1302

Tris [1- (3'-methyleneoxyG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-methyleneoxyG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 15H), 7.22 (t, 1H), 7.02 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1303

Tris [1- (4'-methyleneoxyG1-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-methyleneoxyG1-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.30-7.49 (m, 15H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1304

Tris [1- (2'-methyleneoxyG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-methyleneoxyG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 24H), 7.13 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1305

Tris [1- (3'-methyleneoxyG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-methyleneoxyG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 25H), 7.22 (t, 1H), 7.02 (d, 1H), 6.67 (d , 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1306

Tris [1- (4'-methyleneoxyG2-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-methyleneoxyG2-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.47 (m, 25H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1307

Tris [1- (2'-methyleneoxyG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-methyleneoxyG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 44H), 7.15 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1308

Tris [1- (3'-methyleneoxyG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-methyleneoxyG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 45H), 7.25 (t, 1H), 7.02 (d, 1H), 6.67 (d , 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 ( s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1309

Tris [1- (4'-methyleneoxyG3-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-methyleneoxyG3-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.27-7.41 (m, 45H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1310

Tris [1- (2'-methyleneoxyG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (2'-methyleneoxyG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 84H), 7.14 (m, 3H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1311

Tris [1- (3'-methyleneoxyG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (3'-methyleneoxyG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 85H), 7.22 (t, 1H), 7.02 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1312

Tris [1- (4'-methyleneoxyG4-biphenyl) -1H-pyrazoletto] iridium (III)

Tris [1- (4'-methyleneoxyG4-biphenyl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 43]

¹ H-NMR (CDCl ₃ ): δ 7.77 (d, 1H), 7.72 (d, 1H), 7.29-7.43 (m, 85H), 7.12 (d, 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1313

Tris [1- (5-methoxy-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methoxy-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 6.25 (t, 1H), 6.05 (d, 1H), 3.73 (s, 3H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1314

Tris [1- (5-OG1-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG1-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.30-7.49 (m, 10H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.24 ( t, 1H), 6.08 (d, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1315

Tris [1- (5-OG2-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG2-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.56 (m, 2H), 7.29-7.43 (m, 20H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54- 6.58 (m, 3H), 6.26 (t, 1H), 6.03 (d, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1316

Tris [1- (5-OG3-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG3-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.52 (m, 2H), 7.29-7.43 (m, 40H), 6.65-6.52 (m, 22H), 6.22 (t, 1H), 6.04 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1317

Tris [1- (5-OG4-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG4-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 80H), 6.65-6.48 (m, 45H), 6.23 (t, 1H), 6.06 (d, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1318

Tris [1- (5-methyleneoxyG1-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG1-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.30-7.49 (m, 10H), 6.65 (d, 2H, J = 3.9), 6.64 (d, 1H), 6.55 (t, 1H, J = 2.1), 6.24 (t, 1 H), 5.02 (s, 4 H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1319

Tris [1- (5-methyleneoxyG2-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG2-thiophen-2-yl) -1H-pyrazolato] iridium (III)

δ was synthesized and purified by a method similar to the synthesis method of the iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.27-7.47 (m, 20H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.62 ( d, 1H), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 ( s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1320

Tris [1- (5-methyleneoxyG3-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG3-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.27-7.41 (m, 40H), 6.67 (d, 8H, J = 2.1), 6.64 (m, 5H), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.21 (t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H) .

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1321

Tris [1- (5-methyleneoxyG4-thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG4-thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 44]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.29-7.43 (m, 80H), 6.62-6.67 (m, 23H), 6.61 (d, 1H), 6.57 (d, 2H, J = 2.4), 6.25 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1322

Tris [1-5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (2, 3 or 4-methoxy-phenyl) -thiophen-2-yl-1H -pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

Tris [1-5- (2-methoxy-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III):

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.15 (t, 1H), 7.04 (d, 2H), 6.83 (m, 2H), 6.22 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Tris [1-5- (3-methoxy-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III):

¹ H-NMR (CDCl ₃ ): δ 7.56 (m, 2H), 7.24 (t, 1H), 7.06 (m, 2H), 6.73 (d, 1H), 6.21 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Tris [1-5- (4-methoxy-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III):

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.37 (d, 2H), 7.05 (d, 1H), 6.83 (d, 2H), 6.25 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1323

Tris [1-5- (2-OG1-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (2-OG1-phenyl) -thiophen-2-yl-1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.30-7.49 (m, 10H), 7.14 (t, 1H), 7.08 (d, 2H), 6.84 (m, 2H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.23 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1324

Tris [1-5- (3-OG1-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1- [5- (3-OG1-phenyl) -thiophen-2-yl-1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.30-7.49 (m, 10H), 7.27 (t, 1H), 7.05 (m, 3H), 6.73 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.2 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1325

Tris [1-5- (4-OG1-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (4-OG1-phenyl) -thiophen-2-yl-1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.51 (m, 2H), 7.30-7.49 (m, 11H), 7.03 (d, 2H), 6.83 (d, 2H), 6.65 (d, 2H, J = 3.9) 6.55 (t, 1H, J = 2.1), 6.24 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1326

Tris [1-5- (2-OG2-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (2-OG2-phenyl) -thiophen-2-yl-1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 20H), 7.14 (t, 1H), 7.08 (d, 2H), 6.84 (m, 2H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1327

Tris [1-5- (3-OG2-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (3-OG2-phenyl) -thiophen-2-yl-1H-Pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 20H), 7.24 (t, 1H), 7.07 (m, 3H), 6.73 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1328

Tris [1-5- (4-OG2-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (4-OG2-phenyl) -thiophen-2-yl-1H-Pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 21H), 7.06 (d, 2H), 6.83 (d, 2H), 6.71 (d, 2H, J = 2.1) , 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.2 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1329

Tris [1-5- (2-OG3-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (2-OG3-phenyl) -thiophen-2-yl-1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.29-7.43 (m, 40H), 7.14 (t, 1H), 7.04 (d, 2H), 6.84 (m, 2H), 6.65-6.52 (m, 22H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1330

Tris [1-5- (3-OG3-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (3-OG3-phenyl) -thiophen-2-yl-1H-Pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.52 (m, 2H), 7.29-7.43 (m, 40H), 7.23 (t, 1H), 7.02 (m, 3H), 6.73 (d, 1H), 6.65-6.52 (m, 22H), 6.21 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1331

Tris [1-5- (4-OG3-phenyl) -thiophen-2-yl-1H-pyrazoletto] iridium (III)

Tris [1-5- (4-OG3-phenyl) -thiophen-2-yl-1H-Pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 41H), 7.08 (d, 2H), 6.83 (d, 2H), 6.65-6.52 (m, 22H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1332

Tris [1- {5- (2-OG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (2-OG4-phenyl) -thiophen-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.29-7.43 (m, 80H), 7.14 (t, 1H), 7.07 (d, 2H), 6.85 (m, 2H), 6.65-6.48 (m, 45H), 6.24 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1333

Tris [1- {5- (3-OG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (3-OG4-phenyl) -thiophen-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 80H), 7.24 (t, 1H), 7.05 (m, 3H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.24 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1334

Tris [1- {5- (4-OG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (4-OG4-phenyl) -thiophen-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.53 (m, 2H), 7.29-7.43 (m, 81H), 7.06 (d, 2H), 6.83 (d, 2H), 6.73 (d, 1H), 6.65-6.48 (m, 45H), 6.26 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 445 nm.

Example 1335

Tris [1- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (2-methyleneoxyG1-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.30-7.49 (m, 10H), 7.15 (m, 3H), 7.09 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.21 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1336

Tris [1- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (3-methyleneoxyG1-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.30-7.49 (m, 11H), 7.24 (t, 1H), 7.07 (m, 3H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.24 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1337

Tris [1- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (4-methyleneoxyG1-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.30-7.49 (m, 11H), 7.12 (d, 2H), 7.09 (d, 2H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.23 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1338

Tris [1- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (2-methyleneoxyG2-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.52 (m, 2H), 7.27-7.47 (m, 20H), 7.15 (m, 3H), 7.08 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1339

Tris [1- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (3-methyleneoxyG2-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.27-7.47 (m, 21H), 7.25 (t, 1H), 7.0 (m, 3H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1340

Tris [1- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (4-methyleneoxyG2-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.54 (m, 2H), 7.27-7.47 (m, 21H), 7.12 (d, 2H), 7.01 (d, 2H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1341

Tris [1- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (2-methyleneoxyG3-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.27-7.41 (m, 40H), 7.17 (m, 3H), 7.09 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1342

Tris [1- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {5- (3-methyleneoxyG3-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.24 (t, 1H), 7.08 (m, 3H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1343

Tris [1- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (4-methyleneoxyG3-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.27-7.41 (m, 41H), 7.12 (d, 2H), 7.08 (d, 2H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.23 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1344

Tris [1- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (2-methyleneoxyG4-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.29-7.43 (m, 80H), 7.13 (m, 3H), 7.04 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.24 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1345

Tris [1- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (3-methyleneoxyG4-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.27 (t, 1H), 7.06 (m, 3H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.25 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1346

Tris [1- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -1 H-pyrazoletto] iridium (III)

Tris [1- {5- (4-methyleneoxyG4-phenyl) -thiophen-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 45]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.29-7.43 (m, 81H), 7.12 (d, 2H), 7.09 (d, 2H), 6.62-6.67 (m, 23H), 6.57 (d, 2H, J = 2.4), 6.26 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1347

Tris [1- {7- (4-methoxy-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-methoxy-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.84 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.64 (m, 2H), 7.44 (m, 2H), 6.83 (d, 2H ), 6.46 (t, 1 H), 3.9 (s, 2 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1348

Tris [1- {7- (4-OG1-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-OG1-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.84 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.64 (m, 2H), 7.30-7.49 (m, 12H), 6.65 (d , 2H, J = 3.9), 6.83 (d, 2H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H), 3.9 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1349

Tris [1- {7- (4-OG2-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-OG2-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.85 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.63 (m, 2H), 7.29-7.43 (m, 22H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.83 (d, 2H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H), 3.9 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1350

Tris [1- {7- (4-OG3-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-OG3-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.84 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.64 (m, 2H), 7.29-7.43 (m, 42H), 6.83 (d , 2H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H), 3.9 ( s, 2H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1351

Tris [1- {7- (4-OG4-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-OG4-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

_{^{1 H-NMR (CDCl 3)}} : δ 7.84 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.62 (m, 2H), 7 .29-7.43 (m, 82H), 6.83 (d, 2H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.01 (s, 32H), 5.03 (s, 16H), 4.95-4.92 (m, 28H ), 3.92 (s, 2 H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1352

Tris [1- {7- (4-methyleneoxyG1-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-methyleneoxyG1-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.85 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.64 (m, 2H), 7.30-7.49 (m, 12H), 7.15 (d , 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H), 3.93 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1353

Tris [1- {7- (4-methyleneoxyG2-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-methyleneoxyG2-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.85 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.61 (m, 2H), 7.27-7.47 (m, 22H), 7.14 (d , 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H), 3.91 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1354

Tris [1- {7- (4-methyleneoxyG3-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-methyleneoxyG3-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.83 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.64 (m, 2H), 7.27-7.41 (m, 42H), 7.13 (d , 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H), 3.91 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1355

Tris [1- {7- (4-methyleneoxyG4-phenyl) -9H-floren-2-yl} -1H-pyrazoletto] iridium (III)

Tris [1- {7- (4-methyleneoxyG4-phenyl) -9H-fluoren-2-yl} -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 46]

¹ H-NMR (CDCl ₃ ): δ 7.85 (m, 2H), 7.75 (m, 2H), 7.72 (d, 1H), 7.63 (m, 2H), 7.29-7.43 (m, 82H), 7.14 (d , 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 440 nm.

Example 1356

Tris [1- (6-methoxy-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-methoxy-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.55 (d, 1H), 7.43 (s, 1H), 6.81 (d, 1H), 6.23 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1357

Tris [1- (6-OG1-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-OG1-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.53 (d, 1H), 7.30-7.49 (m, 11H), 6.65 (d, 2H, J = 3.9), 6.83 (d, 1H) 6.55 (t, 1H, J = 2.1), 6.24 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1358

Tris [1- (6-OG2-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-OG2-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.53 (d, 1H), 7.29-7.43 (m, 21H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.8 (d, 1H), 6.54-6.58 (m, 3H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm

Example 1359

Tris [1- (6-OG3-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-OG3-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.53 (d, 1H), 7.29-7.43 (m, 41H), 6.83 (d, 1H), 6.65-6.52 (m, 22H), 6.23 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1360

Tris [1- (6-OG4-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-OG4-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.53 (d, 1H), 7.29-7.43 (m, 81H), 6.83 (d, 1H), 6.65-6.48 (m, 45H), 6.24 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1361

Tris [1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-methyleneoxyG1-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.52 (m, 2H), 7.30-7.49 (m, 10H), 7.14 (d, 1H), 6.65 (d, 2H, J = 3.9) , 6.55 (t, 1H, J = 2.1), 6.23 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 500 nm.

Example 1362

Tris [1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-methyleneoxyG2-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.52 (m, 2H), 7.27-7.47 (m, 20H), 7.14 (d, 1H), 6.67 (d, 4H, J = 2.1) , 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 8H), 4.95 ( s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 500 nm.

Example 1363

Tris [1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-methyleneoxyG3-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.53 (m, 2H), 7.27-7.41 (m, 40H), 7.15 (d, 1H), 6.67 (d, 8H, J = 2.1) , 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.2 (t, 1H), 4.99 (s, 16H), 4.95 ( d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 500 nm.

Example 1364

Tris [1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (6-methyleneoxyG4-benzo [b] thiophen-2-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 47]

¹ H-NMR (CDCl ₃ ): δ 7.55 (m, 2H), 7.52 (m, 2H), 7.29-7.43 (m, 80H), 7.14 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.22 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 500 nm.

Example 1365

Tris [1- (4-methoxy-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methoxy-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.64 (d, 1H), 7.52 (m, 2H), 7.33 (t, 1H), 7.23 (d, 1H), 6.64 (d, 1H ), 6.46 (t, 1 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 1366

Tris [1- (4-OG1-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG1-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.61 (d, 1H), 7.52 (m, 2H), 7.30-7.49 (m, 11H), 7.22 (d, 1H), 6.65 (d , 2H, J = 3.9), 6.64 (d, 1H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 1367

Tris [1- (4-OG2-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG2-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.52 (m, 2H), 7.29-7.43 (m, 21H), 7.24 (t, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.63 (d, 1H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 1368

Tris [1- (4-OG3-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG3-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.63 (d, 1H), 7.52 (m, 2H), 7.29-7.43 (m, 41H), 7.23 (t, 1H), 6.64 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 1369

Tris [1- (4-OG4-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-OG4-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.63 (d, 1H), 7.52 (m, 2H), 7.29-7.43 (m, 81H), 7.23 (t, 1H), 6.64 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 515 nm.

Example 1370

Tris [1- (4-methyleneoxyG1-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG1-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.65 (d, 1H), 7.63 (d, 1H), 7.55 (d, 1H), 7.51 (d, 1H), 7.30-7.49 (m, 11H), 7.23 (t , 1H), 7.15 (d, 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s , 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1371

Tris [1- (4-methyleneoxyG2-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG2-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.65 (d, 1H), 7.61 (d, 1H), 7.55 (d, 1H), 7.52 (d, 1H), 7.27-7.47 (m, 21H), 7.23 (t , 1H), 7.13 (d, 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1372

Tris [1- (4-methyleneoxyG3-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG3-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.65 (d, 1H), 7.62 (d, 1H), 7.55 (d, 1H), 7.52 (d, 1H), 7.27-7.41 (m, 41H), 7.23 (t , 1H), 7.14 (d, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1373

Tris [1- (4-methyleneoxyG4-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (4-methyleneoxyG4-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 48]

¹ H-NMR (CDCl ₃ ): δ 7.65 (d, 1H), 7.62 (d, 1H), 7.55 (d, 1H), 7.54 (d, 1H), 7.29-7.43 (m, 81H), 7.23 (t , 1H), 7.10 (d, 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28 H), 4.61 (s, 2 H), 4.52 (d, 2 H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1374

Tris [1- (5-methoxy-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methoxy-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.44 (d, 1H), 7.36 (m, 1H), 7.24 (d, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 7.12 (t, 1H ), 6.66 (d, 1 H), 6.46 (t, 1 H), 3.73 (s, 3 H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1375

Tris [1- (5-OG1-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG1-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.54 (d, 1H), 7.30-7.49 (m, 12H), 7.23 (t, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 6.65 (m , 3H), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.08 (s, 2H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1376

Tris [1- (5-OG2-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG2-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.54 (d, 1H), 7.29-7.43 (m, 22H), 7.22 (t, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 6.71 (d , 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.63 (d, 1H), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8 H), 4.99 (s, 4 H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1377

Tris [1- (5-OG3-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG3-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by methods analogous to the synthesis of 1- (5-Hydroxy-naphthalen-1-yl) -1H-pyrazole, G3-Br and the preceding iridium (III) complexes. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.54 (d, 1H), 7.29-7.43 (m, 42H), 7.23 (t, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 6.67 (d , 1H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1378

Tris [1- (5-OG4-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-OG4-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.54 (d, 1H), 7.29-7.43 (m, 82H), 7.23 (t, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 6.67 (d , 1H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1379

Tris [1- (5-methyleneoxyG1-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG1-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.30-7.49 (m, 12H), 7.22 (t, 1H), 7.18 (d, 1H), 7.12 (d, 1H), 7.10 (d , 1H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1H), 5.02 (s, 4H), 4.62 (s, 2H), 4.53 (s , 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1380

Tris [1- (5-methyleneoxyG2-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG2-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.27-7.47 (m, 22H), 7.23 (t, 1H), 7.18 (d, 1H), 7.12 (d, 1H), 7.11 (d , 1H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.56 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 (s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1381

Tris [1- (5-methyleneoxyG3-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG3-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.27-7.41 (m, 42H), 7.24 (t, 1H), 7.18 (d, 1H), 7.14 (d, 1H), 7.11 (d , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 ( t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1382

Tris [1- (5-methyleneoxyG4-naphthalein-1-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (5-methyleneoxyG4-naphthalen-1-yl) -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 49]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.29-7.43 (m, 82H), 7.24 (t, 1H), 7.18 (d, 1H), 7.12 (d, 1H), 7.11 (d , 1H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 510 nm.

Example 1383

Tris [1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.37 (d, 1H), 7.32 (d, 1H), 7.37 (d, 2H), 6.83 (m, 2H), 6.46 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1384

Tris [1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazolato] -iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.30-7.49 (m, 12H), 6.83 (m, 3H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1 H), 5.08 (s, 2 H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1385

Tris [1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG2-biphenyl-4-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.29-7.43 (m, 22H), 6.83 (m, 3H), 6.71 (d, 2H, J = 2.1), 6.69 (d, 4H, J = 2.1), 6.54-6.58 (m, 3H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 8H), 4.99 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1386

Tris [1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG3-biphenyl-4-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.29-7.43 (m, 42H), 6.83 (m, 3H), 6.65-6.52 (m, 22H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 4.99 (s, 8H), 4.93 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1387

Tris [1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -1H-pyrazoletto] iridiumIII)

Tris [1- (2,3,6-trifluoro-4'-OG4-biphenyl-4-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.29-7.43 (m, 82H), 6.83 (m, 3H), 6.65-6.48 (m, 45H), 6.46 (t, 1H), 5.09 (s, 2H), 5.03 (s, 16H), 5.01 (s, 32H), 4.95-4.92 (m, 28H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1388

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG1-biphenyl-4-yl) -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.56 (d, 1H), 7.30-7.49 (m, 12H), 7.12 (d, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1 H), 5.02 (s, 4 H), 4.62 (s, 2H), 4.53 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1389

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG2-biphenyl-4-yl) -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.56 (d, 1H), 7.27-7.47 (m, 22H), 7.12 (d, 2H), 6.67 (d, 4H, J = 2.1), 6.64 (d, 2H, J = 2.4), 6.55 (t, 2H, J = 2.4), 6.53 (t, 1H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 8H), 4.95 (s, 4H), 4.61 ( s, 2H), 4.52 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1390

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG3-biphenyl-4-yl) -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.27-7.41 (m, 42H), 7.12 (d, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 16H), 4.95 (d, 12H), 4.61 ( s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1391

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methyleneoxyG4-biphenyl-4-yl) -1H-pyrazolato]

iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.29-7.43 (m, 82H), 7.12 (d, 2H), 6.62-6.67 (m, 23H, J = 2.1), 6.57 (d, 2H, J = 2.4), 6.46 (t, 1H), 4.99 (s, 32H), 4.95 (s, 28H), 4.61 (s, 2H), 4.52 (d, 2H).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1392

Tris [1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazoletto] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-methoxy-biphenyl-4-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.37 (d, 2H), 7.32 (d, 1H), 6.83 (m, 2H), 6.46 (t, 1H), 3.73 (s, 3H ).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1393

Tris [1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazollet] iridium (III)

Tris [1- (2,3,6-trifluoro-4'-OG1-biphenyl-4-yl) -1H-pyrazolato] iridium

(III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 7.57 (d, 1H), 7.30-7.49 (m, 13H), 6.83 (m, 2H), 6.65 (d, 2H, J = 3.9), 6.55 (t, 1H, J = 2.1), 6.46 (t, 1 H), 5.08 (s, 2 H), 5.03 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 410 nm.

Example 1394

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.62 (m, 4H), 7.37 (m, 5H), 7.28 (t, 1H ), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 525 nm.

Example 1395

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.63 (m, 4H), 7.30-7.49 (m, 25H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 525 nm.

Example 1396

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.62 (m, 4H), 7.29-7.43 (m, 45H), 7.28 (t , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 525 nm.

Example 1397

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.13 (s, 1H), 7.91 (d, 2H), 7.72 (d, 1H), 7.63 (m, 4H), 7.29-7.43 (m, 85H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 525 nm.

Example 1398

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 7.92 (d, 2H), 7.71 (d, 1H), 7.62 (m, 4H), 7.29-7.43 (m, 165H), 7.28 (t , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 525 nm.

Example 1399

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 7.92 (d, 2H), 7.73 (d, 1H), 7.62 (m, 4H), 7.30-7.49 (m, 25H), 7.28 (t , 1H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1400

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.10 (s, 1H), 7.92 (d, 2H), 7.72 (d, 1H), 7.63 (m, 4H), 7.27-7.47 (m, 45H), 7.28 (t , 1H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.53 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1401

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 7.92 (d, 2H), 7.73 (d, 1H), 7.63 (m, 4H), 7.27-7.41 (m, 85H), 7.23 (t , 1H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.53 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1402

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Dendrimer 67]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 7.93 (d, 2H), 7.73 (d, 1H), 7.62 (m, 4H), 7.29-7.43 (m, 165H), 7.22 (t , 1H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 520 nm.

Example 1403

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. Formula 446

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 8.03 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H), 7.37 (d, 4H), 7.21 (d, 1H ), 7.05 (m, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1404

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.73 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 23H), 7.22 (d , 1H), 7.03 (m, 2H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1405

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-

pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H), 7.29-7.43 (m, 43H), 7.23 (d , 1H), 7.01 (m, 2H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1406

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.74 (d, 1H), 7.62 (m, 3H), 7.29-7.43 (m, 83H), 7.23 (d , 1H), 7.02 (m, 2H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1407

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.10 (s, 1H), 8.03 (d, 1H), 7.73 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 163H), 7.23 (d , 1H), 7.03 (m, 2H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95- 4.92 (m, 56 H).

λ _em (CH ₂ Cl ₂ ) = 560 nm.

Example 1408

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto ] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2thiophen

-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.73 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 23H), 7.21 (d , 1H), 7.12 (d, 4H), 7.03 (m, 2H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 558 nm.

Example 1409

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto ] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2thiophen

-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.73 (d, 1H), 7.62 (m, 3H), 7.27-7.47 (m, 43H), 7.22 (d , 1H), 7.12 (d, 4H), 7.06 (m, 2H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.56 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 558 nm.

Example 1410

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto ] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen

-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.73 (d, 1H), 7.64 (m, 3H), 7.27-7.41 (m, 83H), 7.22 (d , 1H), 7.12 (d, 4H), 7.02 (m, 2H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 558 nm.

Example 1411

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-thiophen-2-yl-pyridineeto ] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-thiophen

-2-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 50]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.71 (d, 1H), 7.63 (m, 3H), 7.29-7.43 (m, 163H), 7.23 (d , 1H), 7.12 (d, 4H), 7.07 (m, 2H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 558 nm.

Example 1412

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -pyridine Etho] Iridium (III)

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.37 (m, 4H), 7.28 (t, 1H), 6.83 (d, 4H), 3.87 (s, 2H), 3.73 (s, 6H) .

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 1413

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl)- PyridineEtho] iridium (III)

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.30-7.49 (m, 25H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J) = 2.1), 5.08 (s, 4H), 5.03 (s, 8H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 1414

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl)- PyridineEtho] iridium (III)

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.71 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 45H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J) = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 1415

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl)- PyridineEtho] iridium (III)

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.63 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 85H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 ( s, 32H), 4.99 (s, 16H), 4.93 (s, 8H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 1416

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl)- PyridineEtho] iridium (III)

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 165H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 ( s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 545 nm.

Example 1417

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -Pyridine ether] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridineato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.30-7.49 (m, 26H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J) = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 540 nm.

Example 1418

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -Pyridine ether] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.21 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.73 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.27-7.47 (m, 46H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.56 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s , 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 540 nm.

Example 1419

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -Pyridine ether] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.22 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.63 (m, 4H), 7.55 (d, 1H), 7.27-7.41 (m, 86H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J) = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d , 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 540 nm.

Example 1420

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (9H-floren-2-yl) -Pyridine ether] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (9H-fluoren-2-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 56]

¹ H-NMR (CDCl ₃ ): δ 8.22 (s, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H ), 7.62 (m, 4H), 7.55 (d, 1H), 7.29-7.43 (m, 166H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H) , J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H), 3.87 (s, 2H).

λ _em (CH ₂ Cl ₂ ) = 540 nm.

Example 1421

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -pyridine Etho] Iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.94 (d, 1H), 7.82 (d, 1H), 7.73 (d, 1H), 7.64 (m, 3H ), 7.33 (m, 6H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1422

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl)- PyridineEtho] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.83 (d, 1H), 7.76 (d, 1H), 7.64 (m, 3H ), 7.30-7.49 (m, 26H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1423

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl)- PyridineEtho] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.83 (d, 1H), 7.71 (d, 1H), 7.63 (m, 3H ), 7.29-7.43 (m, 46H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1424

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl)- PyridineEtho] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 8.02 (d, 1H), 7.92 (d, 1H), 7.83 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H ), 7.29-7.43 (m, 86H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1425

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl)- PyridineEtho] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 8.02 (d, 1H), 7.92 (d, 1H), 7.81 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H ), 7.29-7.43 (m, 166H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95- 4.92 (m, 56 H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1426

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -Pyridine ether] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -pyridinato] iridium ( III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.83 (d, 1H), 7.71 (d, 1H), 7.62 (m, 3H ), 7.30-7.49 (m, 26H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1427

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -Pyridine ether] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 '']

terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.63 (m, 3H ), 7.27-7.47 (m, 46H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1428

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -Pyridine ether] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 '']

terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.72 (d, 1H), 7.63 (m, 3H ), 7.27-7.41 (m, 86H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.56 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1429

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -Pyridine ether] iridium (III)

Tris [2-benzo [b] thiophen-2-yl-5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 '']

terphenyl-5'-yl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 57]

¹ H-NMR (CDCl ₃ ): δ 8.10 (s, 1H), 8.02 (d, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.73 (d, 1H), 7.63 (m, 3H ), 7.29-7.43 (m, 166H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 590 nm.

Example 1430

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] iridium ( III)

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 7.92 (d, 1H), 7.73 (m, 4H), 7.62 (m, 4H), 7.43 (t, 1H), 7.37 (d, 4H ), 7.32 (m, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1431

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.93 (d, 1H), 7.74 (m, 4H), 7.64 (m, 4H), 7.30-7.49 (m, 26H), 6.83 (d , 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1432

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.91 (d, 1H), 7.73 (m, 4H), 7.63 (m, 4H), 7.29-7.43 (m, 46H), 6.83 (d , 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1433

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.93 (d, 1H), 7.74 (m, 4H), 7.63 (m, 4H), 7.29-7.43 (m, 86H), 6.83 (d , 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1434

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphthalen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.92 (d, 1H), 7.73 (m, 4H), 7.63 (m, 4H), 7.29-7.43 (m, 166H), 6.83 (d , 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.01 (s, 64H), 5.03 (s, 32H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1435

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphth

alen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.92 (d, 1H), 7.71 (m, 4H), 7.61 (m, 4H), 7.30-7.49 (m, 26H), 7.12 (d , 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1436

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphth

alen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.91 (d, 1H), 7.73 (m, 4H), 7.63 (m, 4H), 7.27-7.47 (m, 46H), 7.12 (d , 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1437

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphth

alen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.93 (d, 1H), 7.71 (m, 4H), 7.62 (m, 4H), 7.27-7.41 (m, 86H), 7.12 (d , 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 ( s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1438

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2-naphthalene-1-yl-pyridineeto] Iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2-naphth

alen-1-yl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.94 (d, 1H), 7.74 (m, 4H), 7.62 (m, 4H), 7.29-7.43 (m, 166H), 7.12 (d , 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1439

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl ) -Pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethoxy- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.72 (d, 1H), 7.63 (m, 4H), 7.37 (d, 4H), 6.83 (d, 4H), 6.68 (s, 1H ) 3.73 (s, 6 H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1440

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro- Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG1, OG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl)- pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.72 (d, 1H), 7.62 (m, 4H), 7.30-7.49 (m, 24H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1441

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro- Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG2, OG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl)- pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.73 (d, 1H), 7.64 (m, 4H), 7.29-7.43 (m, 44H), 6.83 (d, 4H), 6.68 (s , 1H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1442

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro- Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG3, OG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl)- pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.73 (d, 1H), 7.63 (m, 4H), 7.29-7.43 (m, 84H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1443

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro- Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-OG4, OG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl)- pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.73 (d, 1H), 7.63 (m, 4H), 7.29-7.43 (m, 164H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1444

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro -Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG1- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.73 (d, 1H), 7.63 (m, 4H), 7.30-7.49 (m, 24H), 6.83 (d, 4H), 6.68 (s , 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1445

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro -Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG2- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.74 (d, 1H), 7.63 (m, 4H), 7.27-7.47 (m, 44H), 6.83 (d, 4H), 6.68 (s , 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 ( s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1446

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro -Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG3- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.02 (s, 1H), 7.73 (d, 1H), 7.64 (m, 4H), 7.27-7.41 (m, 85H), 6.83 (d, 4H), 6.68 (s , 1H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.56 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 ( s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1447

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] tphenyl-5'-yl) -2- (2,3,5-trifluoro -Phenyl) -pyridineeto] iridium (III)

Tris [5- (4,4 ''-dimethyleneoxyG4- [1,1 ', 3', 1 ''] terphenyl-5'-yl) -2- (2,3,5-trifluoro-phenyl) -pyridine] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [115]

¹ H-NMR (CDCl ₃ ): δ 8.03 (s, 1H), 7.73 (d, 1H), 7.63 (m, 4H), 7.29-7.43 (m, 164H), 6.83 (d, 4H), 6.68 (s , 1H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 460 nm.

Example 1448

Tris [4 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [4 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.63 (m, 3H), 7.53 (m, 1H), 7.47 (t, 1H ), 7.41 (t, 1H), 7.37 (d, 4H), 6.98 (t, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 530 nm.

Example 1449

Tris [4 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [4 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.01 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 27H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 530 nm.

Example 1450

Tris [4 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [4 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.10 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.63 (m, 3H), 7.29-7.43 (m, 47H), 6.98 (t , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 530 nm.

Example 1451

Tris [4 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [4 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 87H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 530 nm.

Example 1452

Tris [4 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III)

Tris [4 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridina

to] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.03 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.29-7.43 (m, 167H), 6.98 (t , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 530 nm.

Example 1453

Tris [4 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III )

Tris [4 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.30-7.49 (m, 27H), 7.12 (d , 4H), 6.98 (t, 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm

Example 1454

Tris [4 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III )

Tris [4 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.11 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.27-7.47 (m, 47H), 7.12 (d , 4H), 6.98 (t, 1H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 1455

Tris [4 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (III )

Tris [4 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -2-phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 8.01 (s, 1H), 7.95 (d, 1H), 7.62 (m, 3H), 7.27-7.41 (m, 87H), 7.12 (d , 4H), 6.98 (t, 1H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 1456

Tris [4 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -2-phenyl-pyridineeto] iridium (IIII )

Tris [4 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl-pyridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 109]

¹ H-NMR (CDCl ₃ ): δ 8.12 (d, 1H), 8.03 (s, 1H), 7.95 (d, 1H), 7.61 (m, 3H), 7.29-7.43 (m, 167H), 7.12 (d , 4H), 6.98 (t, 1H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 527 nm.

Example 1457

Tris [1- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] iridium ( III)

Tris [1- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.32 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.53 (m, 1H), 7.42 (t, 1H), 7.37 (d, 4H), 7.13 (d, 1H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1458

Tris [1- {3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] iridium (III)

Tris [1- {3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.32 (d, 1H), 8.01 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.73 (d, 1H), 7.63 (m, 4H ), 7.30-7.49 (m, 26H), 7.13 (d, 1H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s , 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1459

Tris [1- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] iridium (III)

Tris [1- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.31 (d, 1H), 8.01 (s, 1H), 7.95 (d, 1H), 7.93 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.29-7.43 (m, 46H), 7.15 (d, 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1460

Tris [1- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] iridium (III)

Tris [1- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Ligand 1114]

¹ H-NMR (CDCl ₃ ): δ 8.32 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.72 (d, 1H), 7.64 (m, 4H ), 7.29-7.43 (m, 86H), 7.13 (d, 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 ( s, 16 H), 4.93 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1461

Tris [1- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] iridium (III)

Tris [1- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} iso

quinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.31 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.29-7.43 (m, 166H), 7.13 (d, 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 ( s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 605 nm.

Example 1462

Tris [1- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.31 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.93 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.30-7.49 (m, 26H), 7.12 (m, 5H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s , 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1463

Tris [1- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.32 (d, 1H), 8.03 (s, 1H), 7.95 (d, 1H), 7.94 (d, 1H), 7.71 (d, 1H), 7.63 (m, 4H ), 7.27-7.47 (m, 46H), 7.12 (m, 5H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4) , 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1464

Tris [1- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.31 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.91 (d, 1H), 7.72 (d, 1H), 7.63 (m, 4H ), 7.27-7.41 (m, 86H), 7.12 (m, 5H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4) , 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1465

Tris [1- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} isocurolineto] Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} isoquinolinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 58]

¹ H-NMR (CDCl ₃ ): δ 8.31 (d, 1H), 8.02 (s, 1H), 7.95 (d, 1H), 7.92 (d, 1H), 7.73 (d, 1H), 7.62 (m, 4H ), 7.29-7.43 (m, 164H), 7.12 (m, 5H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 600 nm.

Example 1466

Tris [6- {5 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineeto] iridium ( III)

Tris [6- {5 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenan

thridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.01 (s, 1H), 8.0 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.7 (d, 1H), 7.6 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.5 (t, 1H), 7.4 (m, 1H), 7.37 (d, 4H), 6.83 (d, 4H), 3.73 (s, 6H)

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1467

Tris [6- {5 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineeto] iridium (III)

Tris [6- {5 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenan

thridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.12 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.74 (d, 1H), 7.63 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.30-7.49 (m, 26H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1468

Tris [6- {5 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridineeto] iridium ( III)

Tris [6- {5 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenan

thridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.7 (d, 1H), 7.64 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 46H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J) = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1469

Tris [6- {5 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridineeto] iridium ( III)

Tris [6- {5 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenan

thridinato] iridium (III)

Synthesis and purification was carried out by a method similar to the synthesis method of the foregoing iridium (III) complexes. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.71 (d, 1H ), 7.63 (m, 4H), 7.57 (t, 1H), 7.29-7.43 (m, 86H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 ( s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1470

Tris [6- {5 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridineeto] iridium ( III)

Tris [6- {5 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenan

thridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.63 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.29-7.43 (m, 166H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 ( s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 650 nm.

Example 1471

Tris [6- {5 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineeto] Iridium (III)

Tris [6- {5 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.05 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.71 (d, 1H ), 7.63 (m, 4H), 7.57 (t, 1H), 7.30-7.49 (m, 26H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 640 nm.

Example 1472

Tris [6- {5 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineeto] Iridium (III)

Tris [6- {5 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.02 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.72 (d, 1H), 7.71 (d, 1H ), 7.63 (m, 4H), 7.57 (t, 1H), 7.27-7.47 (m, 46H), 6.83 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.5 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s , 4H).

λ _em (CH ₂ Cl ₂ ) = 640 nm.

Example 1473

Tris [6- {5 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineethiridium (III)

Tris [6- {5 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.64 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.27-7.41 (m, 86H), 6.83 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J) = 2.4), 6.56 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d , 4H).

λ _em (CH ₂ Cl ₂ ) = 640 nm.

Example 1474

Tris [6- {5 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} phenanthridineeto] Iridium (III)

Tris [6- {5 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} phenanthridinato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 31]

¹ H-NMR (CDCl ₃ ): δ 8.11 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 7.87 (d, 2H), 7.73 (d, 1H), 7.64 (m, 4H ), 7.71 (d, 1H), 7.57 (t, 1H), 7.27-7.41 (m, 167H), 6.83 (d, 4H), 6.67 (d, 46H, J = 2.1), 6.64 (d, 4H, J) = 2.4), 6.56 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (d, 56H), 4.61 (s, 4H), 4.52 (d , 4H).

λ _em (CH ₂ Cl ₂ ) = 640 nm.

Example 1475

Tris [2- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium (III )

Tris [2- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzo

hiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.84 (d, 1H), 7.75 (s, 1H), 7.63 (m, 3H), 7.55 (m, 2H), 7.43 (m, 1H ), 7.37 (m, 5H), 6.83 (d, 4H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 596 nm.

Example 1476

Tris [2- (3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) phenyl) benzothiazoleto] iridium (III )

Tris [2- (3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) phenyl) benzo

thiazolato] ridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.82 (d, 1H), 7.74 (s, 1H), 7.62 (m, 3H), 7.55 (m, 2H), 7.30-7.49 (m , 26H), 6.83 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 596 nm.

Example 1477

Tris [2- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium ( III)

Tris [2- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzo

thiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.01 (d, 1H), 7.83 (d, 1H), 7.74 (s, 1H), 7.64 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m , 46H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 5.09 (s, 4H), 5.03 (s, 16 H), 4.99 (s, 8 H).

λ _em (CH ₂ Cl ₂ ) = 596 nm.

Example 1478

Tris [2- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium ( III)

Tris [2- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzo

thiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.84 (d, 1H), 7.75 (s, 1H), 7.66 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m , 86H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 596 nm.

Example 1479

Tris [2- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium ( II)

Tris [2- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzo

thiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.81 (d, 1H), 7.73 (s, 1H), 7.64 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m 166H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95-4.92 (m, 56H).

λ _em (CH ₂ Cl ₂ ) = 596 nm.

Example 1480

Tris [2- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium (III)

Tris [2- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzothiazolato] iridium (III)

Synthesis and purification was carried out by a method similar to the synthesis method of the foregoing iridium (III) complex.

¹ H-NMR (CDCl ₃ ): δ 8.03 (d, 1H), 7.83 (d, 1H), 7.71 (s, 1H), 7.63 (m, 3H), 7.55 (m, 2H), 7.30-7.49 (m , 26H), 7.12 (d, 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s , 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1481

Tris [2- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium (III)

Tris [2- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.80 (d, 1H), 7.71 (s, 1H), 7.63 (m, 3H), 7.55 (m, 2H), 7.27-7.47 (m , 46H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1482

Tris [2- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium (III)

Tris [2- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex.

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.84 (d, 1H), 7.74 (s, 1H), 7.63 (m, 3H), 7.55 (m, 2H), 7.27-7.41 (m , 86H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.5 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1483

Tris [2- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} benzothiazoleto] iridium (III)

Tris [2- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} benzothiazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 41]

¹ H-NMR (CDCl ₃ ): δ 8.02 (d, 1H), 7.84 (d, 1H), 7.74 (s, 1H), 7.63 (m, 3H), 7.55 (m, 2H), 7.29-7.43 (m , 166H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 595 nm.

Example 1484

Tris [1- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazoleto] iridium (III)

Tris [1- {3 '-(4,4' '-dimethoxy- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.63 (m, 2H), 7.53 (m, 2H), 7.37 (d, 4H), 7.30 (t, 1H ), 7.22 (d, 1H), 6.83 (d, 4H), 6.46 (t, 1H), 3.73 (s, 6H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1485

Tris [1- {3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazoleto Iridium (III)

Tris [1- {3 '-(4,4' '-OG1, OG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III )

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.62 (m, 3H), 7.53 (m, 2H), 7.30-7.49 (m, 24H), 7.22 (d , 1H), 6.83 (d, 4H), 6.46 (t, 1H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.08 (s, 4H), 5.03 (s , 8H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1486

Tris [1- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazoleto] Iridium (III)

Tris [1- {3 '-(4,4' '-OG2, OG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III )

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.87 (d, 1H), 7.72 (d, 1H), 7.63 (m, 3H), 7.52 (m, 2H), 7.29-7.43 (m, 44H), 7.21 (d , 1H), 6.83 (d, 4H), 6.71 (d, 4H, J = 2.1), 6.69 (d, 8H, J = 2.1), 6.54-6.58 (m, 6H), 6.46 (t, 1H), 5.09 (s, 4H), 5.03 (s, 16H), 4.99 (s, 8H).

λ _em (CH ₂ Cl ₂ ) = 420 nm

Example 1487

Tris [1- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazoleto ] Iridium (III)

Tris [1- {3 '-(4,4' '-OG3, OG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III )

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.60 (m, 3H), 7.52 (m, 2H), 7.29-7.43 (m, 84H), 7.22 (d , 1H), 6.83 (d, 4H), 6.65-6.52 (m, 44H), 6.46 (t, 1H), 5.09 (s, 4H), 5.03 (s, 32H), 4.99 (s, 16H), 4.93 ( s, 8H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1488

Tris [1- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazoleto ] Iridium (III)

Tris [1- {3 '-(4,4' '-OG4, OG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III )

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.62 (m, 3H), 7.52 (m, 2H), 7.29-7.43 (m, 164H), 7.24 (d , 1H), 6.83 (d, 4H), 6.65-6.48 (m, 90H), 6.46 (t, 1H), 5.09 (s, 4H), 5.03 (s, 32H), 5.01 (s, 64H), 4.95- 4.92 (m, 56 H).

λ _em (CH ₂ Cl ₂ ) = 420 nm.

Example 1489

To tris [1- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazole Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG1- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (m, 4H), 7.52 (m, 2H), 7.30-7.49 (m, 24H), 7.22 (d, 1H), 7.12 (d , 4H), 6.65 (d, 4H, J = 3.9), 6.55 (t, 2H, J = 2.1), 5.02 (s, 8H), 4.62 (s, 4H), 4.53 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1490

To tris [1- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazole Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG2- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.61 (m, 3H), 7.52 (m, 2H), 7.27-7.47 (m, 44H), 7.22 (d , 1H), 7.12 (d, 4H), 6.67 (d, 8H, J = 2.1), 6.64 (d, 4H, J = 2.4), 6.55 (t, 4H, J = 2.4), 6.53 (t, 2H, J = 2.4), 4.99 (s, 16H), 4.95 (s, 8H), 4.61 (s, 4H), 4.52 (s, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm

Example 1491

To tris [1- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazole Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG3- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.60 (m, 3H), 7.52 (m, 2H), 7.27-7.41 (m, 84H), 7.22 (d , 1H), 7.12 (d, 4H), 6.67 (d, 16H, J = 2.1), 6.64 (d, 8H, J = 2.4), 6.55 (t, 8H, J = 2.4), 6.53 (t, 4H, J = 2.4), 4.99 (s, 32H), 4.95 (d, 24H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1492

To tris [1- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] tphenyl-5'-yl) -phenyl} -1H-pyrazole Iridium (III)

Tris [1- {3 '-(4,4' '-dimethyleneoxyG4- [1,1', 3 ', 1' '] terphenyl-5'-yl) -phenyl} -1H-pyrazolato] iridium (III)

Synthesis and purification were carried out by a method similar to the synthesis method of the foregoing iridium (III) complex. [Formula 51]

¹ H-NMR (CDCl ₃ ): δ 7.67 (d, 1H), 7.62 (d, 1H), 7.60 (m, 3H), 7.51 (m, 2H), 7.29-7.43 (m, 164H), 7.22 (d , 1H), 7.12 (d, 4H), 6.62-6.67 (m, 46H, J = 2.1), 6.57 (d, 4H, J = 2.4), 4.99 (s, 64H), 4.95 (s, 56H), 4.61 (s, 4H), 4.52 (d, 4H).

λ _em (CH ₂ Cl ₂ ) = 415 nm.

Example 1493

The absorption characteristics of the light emitting iridium (III) organometallic compound have two bands in the UV-visible region, one of the ligand-specific absorption bands, and the other of the metal-to-ligand charge states (MLCT). -transfer). In Figure 1 2- (3-Gnoxyl-phenyl ) eotneunde indicate the absorption spectrum of iridium complex of pyridine, the absorption of the ligand and the dendrimer occurred at 285 nm 400 nm in the single term metal-ligand charge transfer can view the state of ¹ MLCT A very weak absorption band near 500 nm showed ³ MLCT, a triplet metal-ligand charge transfer state. In Fig. 2, the excitation spectrum of Ir (III) -OG2 is the same as the absorption spectrum of the ligand, showed the lowest fluorescence intensity when excited at 525 nm, the strongest fluorescence intensity when excited at 285 nm. In the process of PL excitation, the energy pathway assumes that the ligand absorbs energy to excite it as a single term, the single term of the first ligand dies with ¹ MLCT, and then part of the ¹ MLCT state is transferred to ³ MLCT through the ISC process and finally ³ MLCT. The state fluoresces and falls to the ground state. Light emitting iridium (III) organometallic compounds are given strong yellow fluorescence. Figure 3 shows the absorption spectrum of the iridium (III) complex of 2- (3-Gnoxymethylene-phenyl) pyridine, where the intrinsic absorption characteristics of the iridium (III) complex can be seen. Compared with the absorption spectrum of Ir (III) -CH ₃ , the ¹ MLCT state of this complex showed a short wavelength shift near 380 nm and showed strong green fluorescence. The iridium (III) complex of 1- (3-Gnoxy-phenyl) isoquinoline showed strong red color, and the iridium complex of 1- (3-Gnoxymethylene-phenyl) pyrazole showed blue phosphorescence. Photoluminescence spectra for Ir (III) -OCH ₃ and Ir (III) -OG2 of luminescent iridium (III) organometallic complexes in solution are shown in FIG. 4, and Ir of luminescent iridium (III) organometallic complexes on film (III) -OCH ₃ , Ir (III) -OG1 and Ir (III) -OG2 and Ir (III) -CH ₃ , Photoluminescence spectra for Ir (III) -CH ₂ OG1 and Ir (III) -CH ₂ OG2 are shown in FIGS. 5 and 6. Looking at the photoluminescence spectra at the same concentration in Figure 4 it was clearly observed the effect of site separation. 5 and 6, it can be clearly seen that the light emission intensity due to the separation effect increases as G0, G1, and G2, that is, the larger the number of generations. As a result, the light-emitting iridium (III) organic metal of the ligand-substituted ligand is caused by the triplet-triplet extinction, which changes the color of the emission spectrum at high current, or the non-luminescent effect due to strong intermolecular interaction at high concentration. The problem of existing iridium complexes can be overcome.

After the first report by C. W. Tang and J. H. Burroughes, the research of organic light-emitting diodes (OLEDs) has proceeded considerably, but still remains a problem in terms of low quantum efficiency and full color of conventional fluorescent materials. This problem may cause a delay in practical use, and thus, a breakthrough may be found through the discovery of phosphors. The phosphor can use both singlet and triplet for luminescence unlike conventional EL materials. These materials potentially have 100% internal quantum efficiency to improve OLED performance. Among the phosphors, iridium (III) complexes of 2-phenylpyridine show high triplet quantum efficiencies due to spin-orbit coupling between singlet and triplet. This can lead to high triplet efficiency by increasing triplet. Moreover, the emission color of the iridium complex can be easily adjusted according to the structure of the ligand, which is convenient for obtaining the full color. Phosphors, on the other hand, contain triplet excitons, which cause long phosphorescence lifetimes, triplet-triplet extinctions that rapidly reduce phosphorescence efficiency at high current densities, and non-luminescent effects due to strong intermolecular interactions when doped at high concentrations. There is an inherent flaw. To overcome this problem, the design or synthesis of new phosphors is of great importance and can improve device characteristics. This patent covers the design and synthesis of light-emitting iridium (III) organometallic compounds based on blue, green and red, using dendrimer-substituted ligands for full-color display. By utilizing the positional separation effect of the dendrimer, this patent can solve the non-luminescent effect according to the concentration of the iridium complex. This patent is important in the field of OLEDs and new concepts have been introduced in the design and synthesis of electroluminescent materials. The research will also be a new breakthrough in the practical application of OLEDs.

1 is an ultraviolet-visible light absorption spectra of Ir (III) -OCH ₃ , Ir (III) -OG1 and Ir (III) -OG2.

2 is excitation and photoluminescence spectra of Ir (III) -OG 2.

3 is ultraviolet and visible light spectra of Ir (III) -OCH ₃ , Ir (III) -OCH ₂ G1 and Ir (III) -CH ₂ OG2.

4 is a photoluminescent spectra of Ir (III) -PPYOMe and Ir (III) -PPYOG2.

5 is a photoluminescence spectra of Ir (III) -PPYOMe, Ir (III) -PPYOG1 and Ir (III) -PPYOG2 on films.

6 is a photoluminescence spectra of Ir (III) -PPYCH ₃ , Ir (III) -PPYCH ₂ OG1 and Ir (III) -PPYCH ₂ OG2 on films.

Claims (16)

A light-emitting iridium (III) organic metal compound comprising a ligand having a functional formula of Formula 1 and a dendron. [Formula 1] Ar ₁ is selected from the following structure, Ar ₂ is selected from the following structure. [R _a in the formula 1 is H, CH ₃ or F and, R _b and R _c are the same as _{-H, -CH 3, -OCH 3,} -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CH ₂ OG2, -CH ₂ OG3 or -CH ₂ OG4; R _1, R _2, any one selected from R ₃ and R ₄ are -OG1, -OG2, -OG3, -OG4, -CH 2 OG1, -CH 2 OG2, -CH 2 OG3 or -CH ₂ OG4, The remaining substituents are hydrogen; Any one selected from R ₅ , R ₆ , R ₇ , R ₈ and R ₉ is -OG1, -OG2, -OG3, -OG4, -CH ₂ OG1, -CHOG2, -CH ₂ OG3 or -CH ₂ OG4 , The remaining substituents are hydrogen; Any one selected from R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ and R ₁₅ is -OG1, -OG2, -OG3, -OG4, -CH ₂ OG1, -CHOG2, -CH ₂ OG3 or -CH ₂ OG4 , The remaining substituents are hydrogen; R ₁₀ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ and R ₂₁ independently of one another are -OG1, -OG2, -OG3, -OG4, -CH ₂ OG1, -CH ₂ OG2, -CH ₂ OG3 Or -CH ₂ OG4; G1, G2, G3 and G4 have the following structure.] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 2 and 3 below.   [Formula 2]   [Formula 3] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formula 4 or Chemical Formula 5. [Formula 4]   [Formula 5] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 6 to 9.   [Formula 6]   [Formula 7]   [Formula 8]   [Formula 9] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formula 10:   [Formula 10] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from Formula 11 below.   [Formula 11] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 12 to 15:   [Formula 12]   [Formula 13] [Formula 14] [Formula 15] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formula 16. [Formula 16] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formula 17. [Formula 17] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 18 to 21.   [Formula 18]   [Formula 19]   [Formula 20]   [Formula 21] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 22 to 31.   [Formula 22]   [Formula 23]   [Formula 24]   [Formula 25]   [Formula 26]   [Formula 27]   [Formula 28]   [Formula 29]   [Formula 30]   [Formula 31] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 32 to 41:        [Formula 32]   [Formula 33]        [Formula 34]   [Formula 35]   [Formula 36]   [Formula 37]   [Formula 38]   [Formula 39] [Formula 40] [Formula 41] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 42 to 51.   [Formula 42]   [Formula 43]   [Formula 44]   [Formula 45]   [Formula 46]   [Formula 47]   [Formula 48]   [Formula 49]   [Formula 50]   [Formula 51] [Substituent of the above formula is the same as the substituent of formula (1).] The method of claim 1, A light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having a function selected from the following Chemical Formulas 52 to 59. [Formula 52] [Formula 53]   [Formula 54]   [Formula 55] [Formula 56]   [Formula 57]   [Formula 58]   [Formula 59] [Substituent of the above formula is the same as the substituent of formula (1).] Introducing a dendron to an aromatic organic compound to synthesize supramolecules having a light condensing effect; Synthesizing a light-emitting iridium (III) organometallic complex to prepare a light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having the functionality of the compound of formula 1 according to claim 1 comprising a Way. An OLED device containing a light-emitting iridium (III) organic metal compound comprising a ligand and a dendron having the functionality of the compound of formula 1 according to claim 1.