TWI358412B - - Google Patents

Description

1358412 ····················································· The polymer derived and a method of forming the same. [Prior Art] Displays of organic light-emitting diodes (OLEDs), also known as Organic Electroluminescent Display (OEL Display), have self-luminescence, short reaction time, large viewing angle, simple process, and flexibility ( Flexible) and other advantages. The principle of luminescence of organic electroluminescence is similar to that of inorganic materials, and can be broadly classified into two types: small molecule organic light-emitting diodes and polymer organic light-emitting diodes. The small molecule organic light-emitting diode is mainly composed of a small molecule dye or pigment, and the polymer light-emitting diode is mainly a conjugated polymer organic material. The most common disadvantage, whether it is a small molecule dye or pigment, a polymer luminescent material, or even a hole injection material or a hole transport material, is a low glass transition temperature. Due to the excessive Joule heat generated by the OEL element during long-term operation, the temperature of the component operation 7 1358412 often exceeds the Tg of the material, causing the material to recrystallize, resulting in a decrease in the luminous efficiency of the element. In view of this, there is still a need to develop new organic light-emitting diode materials to provide superior products with good thermal stability, low crystallinity, and high luminous efficiency, thereby extending the life of components and improving luminous efficiency. SUMMARY OF THE INVENTION In view of the above-described background of the invention, in order to meet the industrial requirements, the present invention provides a novel pentadylene-containing compound, a polymer derived therefrom, and a method for forming the same. One of the objectives of the present invention is to introduce a pentacene benzene substituent to a ruthenium metal phosphorescent material, so that the energy transfer between molecules can transform the energy transfer in the component to improve energy transfer efficiency and luminous efficiency, and at the same time strengthen steric obstacles. Reduce the quenching effect caused by the concentration. Another object of the present invention is to adjust the color of the phosphorescent material by modifying the substituents on the phenyl-pyridines. Another object of the present invention is to use 9-(pentaphenylbenzene) kawa as the main component, and then select ruthenium and carbazole with a side chain as a long alkyl chain as a monomer, and use Suzuki Coupling to react with HWE to carry out polymer synthesis. The electroluminescent material of the polymer was obtained, and 0PV and Benz〇thiaz〇le were also introduced respectively to improve the photoelectric properties of the polymer. In terms of thermal properties, the pentacene side chain structure is increased by 8 1358412. The steric hindrance of the polymer is added to reduce the molecular pairing, reducing the molecular bond aggregation phenomenon to avoid excessively serious fluorescence red shift; The pentacene benzene side chain structure reduces the degree of rotational freedom. Therefore, the glass transition temperature of the polymer provided by the present invention is higher than that of the general carbene polymer, and has good thermal stability. Accordingly, the present invention can meet economic benefits and industrial applicability. In accordance with the above objects, the present invention discloses a silver complex having a pentacene benzene ligand having the general formula:

Wherein R' and R" are auxiliary ligands, and the ruthenium 117 may be the same or different, and are independently selected from one of the following groups: a hydrogen atom and an electron withdrawing group. In another aspect, the present invention A compound having a 9-(pentaphenylene) carbene structure and a derivative thereof, and a compound having a core structure of 2-(pentaphenylbenzene)biphenyl and a derivative thereof are also disclosed. The invention is directed to a compound containing a pentacenephenyl group, a polymer of the group, and a method for forming the same. In order to thoroughly understand the present invention, detailed steps will be presented in the following description. And its composition. The implementation of the invention is not limited to the two sides of the collar, the face of the strong group step bribes in the fine section, = cost inventions do not turn _. This issue _ health association will describe in detail In addition to the detailed descriptions of the above, the present invention can be widely applied to other embodiments, and the present invention is based on the scope of the present invention. _Photoluminescent material. Its reading is composed of pure money molecules _ light luminescence The materials of red light and green light have been satisfactorily developed, but the progress of the dawn is difficult. Most of the blue phosphorescent molecules use 2-(2,4-difluorophenyl)-pyridine as the ring-shaped metal. The core of the complex ligand. The most widely known is FIrpic, iridium(m)bis (4,6-difluorophenylpyridinato) picolate, in [ITO/CuPc (10 nm)/a-NPD (30 nm)/ FIrpic : CBP (6 wt%) (3 〇 nm) / LiF (1 nm) / Al (100 nm)] element structure, when the high current j = 1 〇〇 mA / cm2, the maximum illuminance is 6400 cd / m2, The maximum external quantum efficiency is about 3.0%, its maximum emission peak is 495 and 540 nm, and the CIE coordinate (x, y) = (〇.16, 0.29). Its maximum external quantum efficiency is about 10%, and the maximum luminous efficiency is 10 lm. /W, the radiant peak is at 470 nm, although it has good efficiency, but its spectrum has a very obvious vibration structure, there is a double peak problem, resulting in 1358412 its light color is less saturated, its cie coordinates (x, y)=(〇.i7,o.34), and depending on the sensitivity of the human eye, this color is more similar to cyan. In addition, it may be the second and practical blue. The phosphorescent material is FIr6, iridium(nr)bis-(4,6'-difluorophenylpyridinato)tetrakis(l-pyrazolyl)borate, which has a maximum external quantum efficiency of about 9-10% and a maximum luminous efficiency of 11-14 lm/W. And the CIE coordinates (x, y) = (0.16, 0.26) have also been greatly improved.

A first embodiment of the present invention discloses a silver complex having a pentacene benzene ligand having the general formula:

R. R"

Where 'G & includes one of the following groups:

twenty two

< R\〇3

R104 R1〇S

:< R\07

R汹 R108

<

R"V

R1JS

Rile R114

Wherein R and R are auxiliary ligands, and R1 to Rll7 may be selected from each other and are independently selected from the group consisting of 虱 atoms and electron withdrawing groups. In other words, the implementation of the ride provides a five-pronged benzene-based recording complex that can be used as a guest luminaire in a scalar element. - The above-mentioned electron withdrawing group contains one of the following groups: a fluorine group and a trimethyl group, and R' and R" are selected from one of the following groups:

In a preferred embodiment of the present embodiment, the above-described silver 1358412 complex having a pentacene benzene ligand comprises one of the following groups.

The method of forming the complex compound, Wei, provides the "the first reagent", which is generally as follows: • xr2 X1 八Z〆 Among them, the Z system is a 5A group element, and the X1 and X2 systems are independently selected from one of the following groups: Chlorine (C1), bromine (βγ) and moth (Ο ' and χ 1 are different from X2. Secondly, a second reagent is provided, and the general formula of the second reagent is as follows: R3 1:^ 曰(〇R)2 13 1358412 where ' R is a hydrogen atom, a silk or an aromatic group 3 which may be the same or different, and R^R^R3 and R4 are the same as those of R and Han 4: a hydrogen atom and an electron-withdrawing group. _-Selected from the next group to react with Na-_"_ into - as follows:

The receiver's S〇n〇gashira coupling reaction with the first intermediate by the base B to form a second intermediate, the general formula of the second intermediate is as follows:

After the completion of the Sonogashira coupling reaction, a Diels-Alder reaction is carried out with tetraphenylcyclopentadiene (TPPDO) and a second intermediate to form a third intermediate. The general formula of the third intermediate is as follows :

14

Secondly, an additive reaction is carried out by silvering the silver with the third intermediate to form a bridged double-body silver complex' bridge-toothed double-body silver complex as follows:

Wherein X3 is selected from one of the group consisting of chlorine (C1), bromine (Br) and iodine (I). Finally, a chelating agent is subjected to a substitution reaction with a halobridged bismuth complex to form a silver complex having a pentacene stupid ligand, and a silver complex having a pentacene benzene ligand. The general formula is as follows:

2 15 十〇彳 -^-Ν〇 where R5 and R6 are selected from one of the following groups: - ◦ ◦ <, +〇Λ〇

Example 1 Referring to scheme 1, an organometallic catalyst Pd(PPh3)4 was reacted with a 5-bromo-2-iodo-pyridine starting material having a reaction selectivity. The starting material is first subjected to a Suzuki coupling reaction with a linoleic acid having a different electron-withdrawing substituent, and the ruthenium atom at the position 2 of the starting material can be preferentially replaced; then the Sonogashira coupling reaction with the phenylacetylene can be used to replace the initial From the bromine atom at the position of No. 5, the compounds 4 to 6 can be successfully obtained by this method, and the desired yield is obtained.

1 (R1=H, ^H. R3=H, ^=Η) 86% 2 (R1=F, R2=H, R^F, R4=H) 89% 3 (R1=H, R2=CF3lR3=H , R4=CF3) 90% 4 (R1=H, R?=H, R^H, R4=H) 83% 5 (R1=F, R2=H. R^F, R^=H) 97% 6 (R1=H, R^CFs.R^H, R4=CF3) 97%

Scheme 1 refers to scheme 2, followed by Diels-Alder reaction of compounds 4 to 6 with tetraphenylcyclopentadienone (TPCDO), which requires about 260 ° C at high temperature, and TPCDO as the reaction medium 1358412

The reaction does not require the addition of a solvent, and the reaction is about three hours of the compound 7 to 9 of the benzene substituent. It can be obtained with pentacene

4 (R1=H, R2=H, R3=H, R4=H) 5 (R1=F, R2=H, R3=F, R4=H) 6 (R1=H, R2=CF3i R3=H, R4 =CF3)

Scheme 2 Referring to Scheme 3, a gas bridged dimeric ruthenium complex was synthesized according to the method published by N_yama on the synthesis of a ruthenium metal complex. IrCl3 3Ηζ〇 is reacted with 2~2.5 equivalents of ligand by using ethoxyethanol (2_eth〇Xyethano1) and deionized water in a ratio of 3:1 as a solvent. After filtration, a pale yellow to yellowish green color can be obtained. The powder of the chlorinated bridged bismuth complex is 1 〇~12. 17 1358412

ΙγΟ3.3Η20

〇i=H, R2=H' r3=h> 2 H R25=H, R3=F, r4=H) 12 (R = H, R2=CF3l R3=H, R4=CF3) 7 (R1=H, R2=H, R3=H, R4=H) 8 (R1=F, R2=H, R3=F, R4=H) g (R1=H, R2=CF3, R3=H, R4=CF3)

Scheme 3 If the base metal of the complex core can be tightly wrapped, not only the ligand can undergo the effect of intramolecular energy transfer, but also the stacking of the bare base metal or the formation of excimer can be avoided and the solid color is affected. Therefore, we modify the orientation. The direction of the second ligand is moving forward. Refer to Scheme 4, in the presence of ethoxyethanol as the solvent and sodium carbonate as the base, at 13 Torr. (: reacted with different auxiliary ligands, and purified to obtain target ruthenium metal complexes 13~17, HOMO of the compounds 13~17, energy difference Eg and LUM〇 are shown in Table i. 1358412

15(R1=F, R^H, R^F, R4=H) 82% 17 <R1=H· R2=CF3, R3=H, R^CFj 49%

Scheme 4

Table 1

Complexes e1/20X (V) HOMO (V) λ (nm)c Eg (V) LUMO (V) 13 Ir(ppy_6ph)2(acac) 0.861a 5.116 486.5 2.550 2.566 14 Ir(F-ppy-6ph)2( Acac) 1.1658 5.420 458.0 2.709 2.711 15 Ir(F-ppy-6ph)2(pic) 1.378a 5.633 441.5 2.811 2.822 16 Ir(CF3-ppy-6ph)2(acac) 1.4358 5.690 425.0 2.920 2.770 17 Ir(CF3-ppy -6ph)2(pic) 1.613b 5.903 413.5 3.001 2.902 a : Reversible redox potential measured relative to Cp2Fe/Cp2Fe+ in dichloromethane solution, where E1/2, Ferrocene〇X=〇.545V b: relative Cp2Fe / Cp2Fe+ Reversible redox potential measured in a cyanide solution, where E1/2, Ferrocene〇X=〇.510V 19 1358412: the intersection of the edge of the longest absorption wavelength and the horizontal line in the UV-Vis spectrum. The spectral data are as follows: 'H NMR (400 MHz, CDC13): δ 7.92 (d, J = 2.0 Hz, 2H), δ 7.29 (d, J = 8.8 Hz, 2H), δ 7.16 (dd, J = 2.0, 8.4 Hz, 2H), δ 6.98~6.70 (m, 52H), δ 6.66~6.64 (m, 2H), δ 6.61 ～6.59 (m, 2H), δ 5.69 (d, ·7=6.8 Hz, 2H), δ 4.95 (s, 1H), δ φ 1.70 (s, 6H); 13C NMR (100 MHz, CDC13): 8182.12, 164.79, 1 48.88, 147.16, 143.88, 140.74, 140.48, 140.28, 140.14, 139.99, 139.79, 139.73, 139.65, 139.12, 139.09, 138.77, 134.96, 134.07, 132.84, 130.96, 130.85, 130.79, 130.73, 130.70, 130.63, 130.60, 128.17, 127.35, 127.17, 126.60, 126.44, 126.28, 126.23, 126.19, 125.75, 125.14, 124.94, 124.90, 122.90, 119.84, 116.05, 101.55, 29.34; MS m/z FAB (NBA) 1414.3 (14), 1513.6 (4); HRMS (Nf) calcd for C99H71IrN202 1512.5144, found 1512.5082 (IVT). Anal, calcd for C99H71IrN202: C,78.60; H,4.73; N,1.85; found C,78·74; H, 5.02; N, 1.98. 14 Spectral data are as follows: MS m/z FAB (NBA) 1585.8 (0.04), 1586.8 (0.02); HRMS (IVT) calcd for C99H67F4IrN202 1584.4767, found 1584.4712 (IVT). Anal, calcd for C99H67F4IrN202: C,75.03; 4.26; N, 1.77; found C, 75.07; H, 4.84; N, 1.53. Compound 15 spectral data is as follows 20 1358412

*H NMR (400 MHz, CD2C12): δ 8.43 (d, ^8.0 Hz, 1H), δ 8.16 (d, J = 1.6 Hz, 1H), δ 8.14~8.09 (m, 1H), δ 7·73~ 7.69 (m, 2H), δ 7.42~7.39 (m, 1H), δ 7.32 (d, /=5.2 Hz, 1H), δ 7.28 (dd, J=1.6, 8.4 Hz, 1H), δ 7.22 (dd, /=1.6, 8.4 Hz, 1H), δ 7.17~7.13 (m, 1H), δ 7.08 (t, J=7.6 Hz, 1H), δ 7.03~6.99 (m, 1H), δ 6_97~6.69 (m, 42H), δ 6.58 (d, /=2.0 Hz, 1H), δ 6.50 (d, J=7.2 Hz, 1H), δ 6.46 (d, J=7.6 Hz, 1H), δ 6.35~6.18 (m, 5H ), δ 4.98 (dd, J=2.0, 7.8 Hz, 1H), δ 4.91 (dd, J=2.0, 7.8 Hz, 1H); 13C NMR (100 MHz,

CD2C12): δ 171.41, 161.50, 160.60, 160.53, 159.03, 152.72, 151.52, 150.31, 149.36, 149.21, 148.59, 141.50, 141.32, 140.85, 140.74, 140.65, 140.54, 140.38, 140.26, 140.23, 140.12, 140.05, 139.97, 139.86, 139.71, 139.51, 139.30, 139.25, 139.03, 138.11, 135.90, 135.65, 134.47, 134.37, 131.43, 131.35, 131.32, 131.24, 131.20, 131.09, 131.04, 130.99, 130.89, 130.75, 130.68, 130.62, 130.16, 128.45, 128.37, 127.78, 127.59, 127.04, 126.97, 126.90, 126.80, 126.62, 126.58, 126.48, 126.43, 126.39, 126.11, 125.44, 125.34, 125.17, 121.25, 121.05, 120.74, 120.56, 115.34, 115.19, 114.59,

(M.s. (400 MHz, CDC13) : δ 7·74 (s, 2H), δ 7_62 (s, 2H), δ 7.40~7.33 (m, 6Η), δ 7.29 (s, 2Η), δ 6.97~6.60 (m, 50Η), δ 4.68 (s, 1Η), δ 1.60 (s, 6H) ; , 3C NMR (100 MHz, CDC13) : δ 183.05, 162.66, 150.31, 150.25, 141.32, 141.26, 141.02, 140.68, 140.65, 139.96, 139.94, 139.91, 139.74, 139.45, 138.54, 136.41, 136.11, 134.03, 133.70, 132.02, 131.21, 131.05, 21 1358412 130.95, 130.90, 130.83, 130.76, 130.64, 130.52, 127.33, 127.01, 126.84, 126.52, 126.40, 126.36, 126.32, 126.14, 125.81, 125.66, 125.20, 125.14, 123.13, 123.15, 122.83, 121.70, 121.29, 116.73, 101.83, 29.46; MS m/z FAB (NBA) 1686.7 (100), 1786.1 (34); HRMS (IVf) Calcd for C, 〇3H67Fi2lrN2〇2 1784.4640, found 1784.4620 (IVT). Anal, calcd for Ci〇3H67F12IrN2〇2: C, 69.31; H, 3.78; N, 1.57; found C, 69.05; H, 4.03; N, 1.55 .

The spectral data of Compound 17 is as follows: NMR (400 MHz, CDC13): δ 8.36 (d, > 8.0 Hz, 1H), δ 8.13 to 8.08 (m, 2H), δ 7.77 (s, 2H), δ 7.45 to 7.40 ( m, 3H), δ 7.35~7.26 (m, 4H), δ 7.20 (dd, «7=2.0, 8.6 Hz, 1Η), δ 7.13 (s, 1Η), δ 7.00~6.92 (m, 5Η), δ 6.88~6.56 (m, 39H), δ 6.50~6·46 (m, 2H), δ 6.36 (d, J=7.6 Hz, 1H), δ 6.19 (d, J=6 Hz, 1H), δ 6.00 ( d, J = 5.6 Hz, 2H); 13C NMR (100 MHz, CDC13): δ 170.91, 151.61, 150.05, 149.81, 148.99, 147.66, 141.48, 141.34,

162.96, 161.63, 141.00, 140.75, 139.71, 139.68, 135.24, 133.38, 130.71, 130.34, 126.51, 126.46, 122.88, 121.96, 140.69, 140.36, 140.24, 140.06, 140.00, 139.82, 139.80, 139.48, 138.56, 138.43, 138.37, 138.21, 136.18, 135.71, 133.11, 131.64, 131.10, 131.02, 130.93, 130.84, 130.80, 130.17, 129.89, 128.80, 128.04, 127.62, 127.09, 126.55, 126.33, 126.24, 126.07, 125.28, 125.17, 125.10, 125.01, 117.83, 117.11; MS m/z FAB (NBA) 1686.2 (100), 1808.7 (44); HRMS (IVT) calcd for C104H64F12IrN3O2 1807.4436, found 1807.4353 (IVT). 22 1358412

Example 2 In general, OLED components are often fabricated by vacuum evaporation. The principle is to sublimate the compound onto the IT glass under vacuum conditions, provided that the compound is capable of withstanding the high temperature test of 300 to 400 °C. There will still be no decomposition or change afterwards. When the material molecules are decomposed during the evaporation process, the decomposed compound may contaminate the components and deteriorate the performance of the components. In the present invention, although the element is produced by spin coating, and the material molecules are not directly heated, the applied current in the test of the element also generates heat and is transmitted to the compound in the element. . Therefore, OLED materials need to have considerable thermal stability, and if the material's thermal cracking temperature (Td) is too low, it will limit its application range. On the other hand, the glass transition temperature Tg of the material also affects the life, efficiency, and chromatic aberration of the component. If the Tg of the material is too low, an external source of heat can cause the material to soften or cause the molecules to create a knot during the fabrication or testing of the component, creating a problem of diffusion between the interfaces of the material. The thermal properties of the silver metal in the £xampie 1 are 13 to 17 as shown in Table 2. Compound U 14 15 16 17 Molecular Weight Τ512.5Τ 1584.48 1607.46 1784.46 1807.44

Td ~423 399 459 411 470

Tg 222 221 219 245 23 1358412

Example 3 Preparation and Characteristics of 元件 Metal Complex 13~17 Doped in PVK 〇 LED Element

The base metal complexes 13 to 17 in Example 1 have poor solubility due to the solubility of 14 and only slightly soluble in dibenzene, and poor film formation in the spin coating of the second gas solution, resulting in low efficiency. This example only discusses the component properties of 13, 15, 16 and 17. The silver metal complexes 13, 15·17 were doped in poly(vinylcarbazole) [PVK, average MW 90000], and PVK was used as the main luminescent material. Since PVK is a derivative of carbazole and has a better ability to transfer holes, electrons entering from the cathode can stay on the silver metal complex and wait for recombination with the hole for light emission. The component fabrication steps are as follows: (1) hole injection layer: spin-coated poly(3,4-ethylenedioxythiophene)-poly(styrene) sufonic acid (hereinafter referred to as [PEDOT/PSS]' has a thickness of about 50 nm; (2) Luminescent layer: In 8 ml of chloroform solution, 100 mg of host material PVK, 40 mg of electron transport layer 2-(4-biphenylyl-5-(4-tertbutylphenyl)-l, 2,3-oxadiazole (PBD) And different doping ratios of the base metal complexes 13, 15-17, and then spin coating the solution on the baked hole injection layer. (3) The metal material of the cathode is conventionally used for low work. A metal material (or 24 1358412 alloy) of a work function, such as a high-active metal such as Li, Mg, Ca·., to facilitate electron injection from a cathode to an electron transport layer, which is formed by thermal evaporation In addition, in order to reduce the energy barrier of the cathode and the electron transport layer and reduce the driving voltage, a layer of electron injecting layer may be introduced between the cathode and the electron transporting layer. The common material is a very thin working function metal complex or oxide. LiF, MgO or Li20. The completed OLED component structure is ITO/P EDOT/13, 15-17-PBD-PVK/Mg/Ag (hereinafter referred to as component work, Π III and IV), the range of doping of the base metal complexes 13, 15-17 is about 15% to 40~ The 1% ' results are shown in the first to third figures. The maximum brightness of the components ^冚 and ... are 2380, 355, 824 and 871 cd/m2, respectively, and the maximum efficiencies are 22.7, 4.37, 18.5 and 15 cd/A, respectively. In addition, the electroluminescence spectra of elements I, IIIII and IV are shown in the fourth figure. As the doping ratio increases, there is no tendency for the element to red-shift (refer to the fifth figure), so that compounds 13, 15-17 are known. The core metal is tightly packed, so there is no need to avoid the general doping ratio of T-Tannihilation in the fabrication of the components; and the brightness of the light is usually proportional to the content of the base metal, so the invention can be made by the __ To improve the brightness. A third embodiment of the present invention discloses a compound having a 9-(pentabenzophene)carbazole structure, the general formula of which is as follows: 25

1358412 G and G may be the same or different, and G1 and G2 are independently selected from one of the following groups: a hydrogen atom, a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, a dentate atom, . J, dP (°R) 2, _B (QR) 2, Β, 〇 φ, _Ar_G3, wherein R is a hydrogen atom, an alkyl group or an aromatic group, Ar is an aromatic group, and G3 is a hydrogen atom. A slow acid group, a thiol group, an amine group, a double bond group or a triple bond group. In addition, the compound having the structure of 9-(pentabenzophenone)carbazole provided in the present embodiment can be applied to an organic solar cell element or to an organic electroluminescence element and/or phosphorescence (ph〇). A sph〇rescence element in a hole injection material, a hole transport material, an emitting material, or a host material. The compound having the structure of 9-(pentabenzophenone)carbazole provided by the present embodiment can be used to form a polymer derived from a 9-(pentaphenylene)carbazole structure, which has 9-(by the above). The pentacene benzene) carbazole structure is formed by reacting with at least one reactive monomer, and the reactive single system is selected from one of the following groups: 26 1358412

Wherein R1, r2, R3, R4 and R5 are independently selected from one of the following groups: an alkyl group and an aromatic group, and the G4 system is a halogen atom, -b(or)2.

~K 乂 , corpse (0R) 2 0 = / ' 0 carboxylic acid group, hydroxyl group, amine group, double bond group or triple bond group, wherein R is a hydrogen atom, an alkyl group or an aromatic group. Further, the polymer derived from the above 9-(pentaphenylene)carbazole structure can be applied to an organic solar cell element or to an organic electroluminescence element and/or a phosphorescence element. A hole injection material, a hole transport material, an emitting material, or a host material. 27 1358412

Example 4 This example provides seven polymers derived from 9(pentaphenyl)carbazole structure (Ρ1-Ρ7 as shown below) and a control polymer ρ8, of which polymer 1>Bu 2 and! > 4-Ρ8 synthesis is synthesized by Suzuki Coupling method. First, the rotten vinegar or boric acid compound monomer and brominated monomer are treated with THF as solvent, pd(pph3)4 as catalyst, and P(t-Bu)3 as Ligand, and added κ3ρ〇4, the reaction temperature was controlled at 7 ° C ° 'reflow reaction for 40 hours. Then, triphenylammonium desertate was added to the reaction as a terminal group, and the reaction was terminated one day later. Finally, we extracted our crude polymer by gas-like imitation, using toluene as the extract, and using column chromatography to remove the salt and heavy metal catalyst. The product was concentrated under reduced pressure and then immersed in sterol. The purified southern molecule is obtained. The molecular weight and molecular weight of the south molecular PH8 are shown in Table 3. The HOMO and LUMO energy level finishing is shown in Table 4.

28 1358412

Table 3 Μη Mw PDI PI 4400 5500 1.25 P2 14200 21000 1.48 29 1358412

P3 24000 35500 1.48 P4 16100 21200 1.33 P5 12200 18000 1.5 P6 16100 21600 1.35 P7 15200 21100 1.39 P8 6900 9100 1.32 Table 4 Oxidation onset energy difference HOMO LUM0 potential (V) (eV) P1 0.87 3.16 5.13 1.97 P2 1.08 3.08 5 34 2.26 P3 0.68 2.49 4. 94 2.45 P4 0.85 3.2 5.11 1.91 P5 0.81 3.16 5.07 1.91 P6 1.08 3.09 a 5.34 2.25 P7 1.2 3. 08 5.46 2.38 P8 0.8 3.2 5.06 1.86

Example 5 The effect of thermal stability on the performance of components can be divided into two parts to say 30 1358412. The first part is the stability of the front part of the component process: although the polymer material film is spin coating, it is not necessary for the small molecule material to be vacuum-heated', but still needs to use vacuum heating metal. As an electrode. Although it is not heated directly on the compound film, the temperature of the metal is extremely high when it settles on the surface of the high molecular film. Therefore, if the thermal decomposition temperature of the polymer is too low, decomposition will occur during vapor deposition. The second part of the component operation process: the working component is continuously absorbed by the voltage, the heat generated and the temperature of the operating environment are absorbed by the polymer in the component. In this step, the glass transition temperature (Tg) of the compound is compared. Low, it will soften the organic material and affect the efficiency of the component. After component fabrication, we measured the glass transition temperature of the compound by thermogravimetry analysis (TGA) measuring the thermal cracking temperature (Td) of the compound and differential scanning calorimetry (DSC). (glass transition temperature, Tg) to understand the thermal properties of the material 'Table 5 shows the glass transition temperature (Tg) and thermal cracking temperature (Td) of the polymer ρι·ρ8. The pyrolysis temperature is above 400 °C, which is a good thermal stability' and the glass transition temperature is between 100~12 (TC), compared with P8 with no pentacene phenyl group in the main chain, P1 The Tg of ~P7 has a significant improvement. The reason is that the steric obstacle of pentacene is extremely large, so the degree of freedom of rotation is reduced, so the Tg is obviously improved. Table 5 31

Thermal Cracking Temperature (Td) Glass Conversion > P1 436°C 118°C P2 415°C 99°C P3 432°C 112°C P4 430°C 118°C P5 421°C 113°C P6 415°C 109° C P7 418°C 91°C P8 440°C 83°C 1358412

Example 5

Scheme 5 shows that the synthesis process of P3 is based on the Horner-Wadsworth-Emmons reaction (HWE reaction) to polymerize P3'. Under the experimental conditions, compound 14 and compound 15 react to form carbon-carbon double bonds to polymerize polymer P3, HWE. The polymer produced by the reaction predicts that the molecular weight will be higher than that of the polymer produced by the Suzuki Coupling reaction. 32 1358412

Scheme 5

Example 6 OLED elements V and VI are fabricated by P6, and their structures are ITO/PEDOT: PSS/P6/LiF/Al and ITO/PEDOT: PSS/ P6_PBD-Ir(ppy)3/LiF/A, P6: PBD : Ir(ppy)3 The weight ratio is 33 丄 412 H 40 : 8 (THF). Referring to the fifth to eleventh figures, the pure P6 component V emits green light with a maximum brightness of 91〇ed/m2, which can be achieved without mixing any electronic or electrical 'same transmission material'. It is a good performance; the component VI mixed with bismuth metal phosphorescent material can emit green light, and after mixing the phosphorescent guest ir(ppy)3, the brightness can reach nearly 2700 cd/m2, the maximum luminous efficiency is 5.2 cd/A, and the components v and VI The characteristics are organized as shown in Table 6. Table 6 Component Starting Voltage Maximum Brightness Maximum Efficiency (V) (cd/m2) (cd/A) V 5.5 910 1.15 VI 11 2650 5.2 This embodiment also discloses a method for forming a 9-(five stupid benzene) card β sitting First, an azole compound and a double halogen compound are provided, and the general formula of the two is as follows: X1

Wherein 'X1 and X2' may be the same or different, and X and X2 are independently selected from one of the following groups: chlorine (C1), bromine (Br) and iodine (I). Next, a 34 1358412 displacement reaction is carried out to form a first intermediate of the carbaryl compound and the bis-based compound. The structural formula is as follows:

X

Wherein 'X is independently selected from the group consisting of: chlorine (C1), odor (Br) and iodine (1); and then 's_gashira coupling reaction with phenylacetylene and the first intermediate to form - second The intermediate, the second intermediate is as follows:

Finally, four tetraphenylcyclopentadienone (TPCDO) were reacted with a second intermediate to form 9-(pentaphenylene) carbene. The structural formula is as follows: 35 1358412

Example 7 Refer to scheme 6 'Firstly use salt to catalyze the reaction to form compound 1' and then compound 1 and phenylacetylene in Sonogashira Coupling reaction to obtain compound 2, then compound 2 and tetraphenylcyclopentadienone in Diels-Alder reaction to obtain compound 3 'final The compound is dissolved in THF and brominated with NBS to obtain 3,6-di-bromo-9-(pentabenzophenone). The spectral data of 4 chelate 3 is as follows: mp 329 ° C - 332 ° C ; !H NMR (400 MHz, CDCh) < 5 6.85 - 7.02 (m, 31H), 7. 23 (t, 2H), 7.32 (t, 2H), 8. 06(t, 2H); 13C NMR (400 MHz, CDCh) 5 109.60, 119.57, 120.12, 123.97, 125.28, 125.32, 125.43, 125.59, 125.67, 126.63, 126.80, 131.41, 131.53, 134.425, 140.35, 36 1358412 140.40, 140.43, 140.47, 140.49, 140.92. The spectral data of compound 4 is as follows: mp > 380 ° C; Ή NMR (400 MHz, CDCh) δ 6. 82~6. 94 (m, 29H ), 7.01(d, 2H), 7.41(d, 2H), 8.10(s, 2H) ; 13C NMR (400 MHz, CDCh) 5 111.34, 112.75, 123.04, 123.65, 125.34, 125.37, 125.45, 126.66, 126.7, 126.82, 129.18, 131.36, 131.5, 132.99, 133.49, 139.87, 140.25, 140.31, 140.36, 140.44, 140.47, 141.23.

37 1358412

NBS, 0°C 5hr, 90%

Scheme 6

Example 8 Referring to scheme 7, first, compound 3 is dissolved in dichloroethane. In addition, POCL3 is dissolved in DMF and then added to the solution of compound 3 at 0 °C. After reacting at 90 °C for 50 hours, Compound 14, the spectral data is as follows: mp > 380 ° C; Ή NMR (400 MHz, CDCh) (5 6. 85-7. 09 (m, 29H), 7. 94 (d, 2H), 8.64 ( d, 2H), 10. ll(s, 2H) ; 13C NMR (400 MHz, CDCh) 5 88. 38 1358412

Scheme 7

Example 9 Referring to Scheme 8, compound 4 is reacted with n-butyllithium reagent at -78 °C in THF and then reacted with 2_isoproxy_4,4,5,5-tetrametyl-l,3,2-dioxaborolan, ie A diboron compound 7 can be obtained.

Scheme 8 39 1358412

Example 10 Referring to Scheme 9, compound 4 is subjected to a Suzuki Coupling reaction with 1-boronic acid 4-methoxy-benzene, followed by hydrolysis to obtain a bishydroxy compound.

Scheme 9 1358412

Example 11 Referring to Scheme 10, the diboron compound 7 is reacted with l-Ch1〇ro_4_viny]benzene to obtain a compound having a double bond. Such a compound having a double bond does not need to add a reagent in the subsequent consideration, so it does not cause harm to the environment and causes air pollution, and the reaction condition is mild (normal temperature and normal pressure), the reaction rate is fast, the conversion rate is high, and the saving can be achieved. manufacturing cost. Accordingly, the products of this example are of high commercial value.

Scheme 10 A fourth embodiment of the present invention discloses a compound having a 2-(pentaphenylbenzene)biphenyl core structure, the general formula of which is as follows:

1358412 G1 and G2 may be the same or different, and G1 and G2 are independently selected from one of the following groups: a hydrogen atom, a tick acid group, a trans group, an amine group, a double bond group or a triple bond group,

-K JH P(〇R) 2 halogen atom, 〇=>, -B(0R)2, d, -Ar-G3, wherein R is a hydrogen atom, an alkyl group or an aromatic group, and Ar is an aromatic A group of groups, G3 is a hydrogen atom, a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group. The compound of the 2-(pentaphenylene) biphenyl core structure provided by the present embodiment can form a polymer derived from a core structure of 2(penta-phenylene) biphenyl, which has 2_ by the above The compound of the (pentaphenyl) stannene core structure is formed by reacting with at least a fox monomer, and the anti-nuclear system is selected from one of the following groups:

42 丄 丄 2

Burning base and aromatic base®, G4 is a money atom, _B(0R)2, —,

'K 〇=> ί , P(〇R) 2 , a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, wherein R is a hydrogen atom, an alkyl group or an aromatic group . In addition, the polymer derived from the above 2_(pentaphenyl)biphenyl core structure can be applied to an organic solar cell element or to an organic electroluminescence element and/or a phosphorescence element. A hole injection material, a hole transport material, an emitting material, or a host material.

Example 12 43 1358412

The compound 1 and phenylacetylene were subjected to Sonogashira coupling to obtain the compound 3 of the triple bond, and the Diels-Alder reaction with the tetraphenylcyclopentadienone was carried out, and the compound 6 of the benzene ring was used, and then the lithium ester was used to reduce the ester to the alcohol group, and the mixture was successfully obtained. Compound 7 is further oxidized by PCC (pyridinium chlorochromate) to obtain compound 8, and compound 7 can also react with SOC12 to replace hydroxyl group with chlorine to obtain compound 9, and finally react with triethyl phosphite and compound 9 to form Phosphate compound 10, it is worth mentioning that the reaction rate is slower than that of the general compound, and it takes 5 days to complete.

44

Scheme 11 1358412 Compound 8:

Mp 325〇C-326〇C; 'H NMR (400 MHz, CDC13) δ 6.12 (d, J= 7.7 Hz, 2H), 6.57 (t, J= 7.5 Hz, 2H), 6.68-6.72 (m, 3H ), 6.74-6.87 (m, 18H), 7.21 (d, J = 8.1 Hz, 3H), 7.55 (d, J = 1.4 Hz, 1H), 7.53 (dd, 8.0, 1.8 Hz, 1H), 7.75 (d , J = 8.4 Hz, 2H), 9.71 (s, 1H), 10.03 (s, 1H); 13C NMR (100 MHz, CDC13) δ 125.35, 125.37, 125.54, 126.63, 126.75, 126.92, 128.99, 129.98, 130.31, 131.07, 131.14, 131.42, 131.49, 131.88, 134.27, 134.98, 136.26, 137.17, 139.43, 140.00, 140.07, 140.13, 140.16, 141.22, 141.83, 144.40, 45 1358412 146.03, 191.64, 191.96 ; MS m/z FAB (NBA) 666.2; HRMS (Μ4-) calcd for C50H34〇2 666.2559, found 666.2566; IR (KBr) 3084, 3059, 3018, 2833, 2737, 1700, 1602, 1498, 1442cm·1.

Mp 188〇C-189〇C; *H NMR (400 MHz, CDC13) δ 1.24 (t,J= 7.1 Hz, 6H), 1.26 (t, J= 7.1 Hz, 6H), 2.79 (d, J= 21.6 Hz, 2H), 3.13 (d, J = 21.6 Hz, 2H), 3.86-4.08 (m, 8H), 6.18 (d, J = 7.6 Hz, 2H), 6.57 (t, J = 6.8 Hz, 2H), 6.68-6.91 (m, 22H), 6.97 (d, J = 8.1 Hz, 4H), 7.13 (dd, 7 = 6.4, 2.3 Hz, 2H); , 3C NMR (100 MHz, CDC13) δ 16.47, 16.50, 16.52 , 32.62, 32.57, 61.98, 62.05, 62.07, 62.14, 125.00, 125.03, 125.11, 126.10, 126.37, 126.43, 126.49, 126.52, 127.91, 127.98, 128.74, 128.85, 128.92, 129.31, 129.42, 129.71, 129.80, 130.53, 131.28 , 131.33, 131.54, 131.86, 135.20, 135.27, 138.57, 138.67, 140.06, 140.13, 140.57, 140.58, 140.72, 140.82; MS m/z FAB (NBA) 910.5; HRMS (M+) calcd for C58H5606P2 910.3552, found 910.3541; IR (KBr) 3453(B), 3059, 3027, 2986, 2898, 1602, 1498, 1442, 1249(S), 1023(8)011-1.

Example 13 Synthetic Polymer PI 46 1358412

Compound 8 (1.20 g, 1.80 mmol) and 1,4-bis-diethyl-2,5-bistrimethylphosphinosyl-phenyl-1,4-dimercaptophosphate (0.95 g, 1.8 mmol) and gasification were taken. The inside (0.17 g, 4.0 mm〇i) was placed in a double-necked flask with nitrogen at one end and a sero-plug at the other end. Inject DMF (5 ml) and THF (5 ml) to

The magnet stirrer was stirred for 30 minutes. After adding t-BuOK (0.81 g, 7.2 mmol), continue to stir for 36 hours, then inject 4-methyibenzaidehyde (0.1 ml) and continue to disturb for 24 hours. Under ice bath, add 5 % sulfur g pulse solution (15 ml) and stroke: L reverse, suction filtration to collect yellow solid. The initial product was dissolved in a gas-like, Ultff heart-shaped sterol towel, and the yellow solid was immediately precipitated. The mixture was evacuated; the yellow solid was collected, vacuum-dried, and the reprecipitation step was repeated 6 times. A yellow solid (1. 15 g) was obtained in a yield. (1) LiCl? t-BuOK, DMF? THF, rt, 36hr —------- (2) 4-MeC6H4CHO, 24hr, 73%

11

Scheme 12 47 1358412

Example 14 Synthesis of Polymer P2 Take Compound 10 (1.50 g, 1.65 mmol) and 4,4'-Dimethyl-2,2,-dinaphthylbiphenyl (0.75 g, 1.6 mmol) and Chlorinated (0.15 g) , 3.6 mmol) placed in a double-necked flask with nitrogen in one end and sero-seal in the other end

live. DMF (4.lml) and THF (4.5 ml) were poured and stirred with a magnetic stirrer for 3 minutes. Add t_Bu〇K (〇_81 g, 7.2 mmol), continue stirring for 36 hours, then re-inject 4-1116 out>^^1^1(16}1>^(0.11111),",, 1^.. Just for an hour. Add the 5% sulphuric acid aqueous solution (15ml) to quench the reaction under ice bath. Pump the gas to collect the yellow solid. Turn the initial product into chloroform and slowly add an equal volume of sterol with a dropper. In the middle, the yellow solid precipitated immediately. The residue was dried in vacuo to dryness. <RTI ID=0.0>>

48 1358412

(1) LiCl, t-BuOK, DMF, THF, rts 36hr (2) 4-MeC6H4CHO, 24hr, 61%

Scheme 13

Example 15 PI single-layer component preparation Lu is in the fabrication of components. 'We use the simplest single-layer structure, which is the anode, the cathode is magnesium metal or calcium metal and then a layer of silver protection, in addition to reduce the energy of hole injection. Barrier, first spin-coat a layer of PEDOT/PSS aqueous solution on the rammed glass as a hole injection layer, bake at 13 〇〇c for 3 minutes, then dispose the polymer solution in a suitable solvent, and smash the mpvDF ^ Membrane filtration, spin coating on the rib glass as an electroluminescent layer, baking with true = (10_2-10·3 torr) and 5 °C to 5, such as eight...m to J 30 After the clock, the cathode metal is evaporated and the component can be measured. The component size is 5_3. 49 1358412 Using Mg (Ag) as the cathode metal, the electroluminescent element of ρι was prepared under the above conditions, and the composition of several different formulations was prepared by using the mouse imitation solvent as the solvent and the thickness was about 7 〇nm. Pi/bnd : 1〇〇/2〇; (yjii) blended PI / PBD : 100/40 ; (VIIII) blended P1 / NTpD : 1〇〇 / 3〇 (The above formula concentration is (4) Experimental test to find out The most efficient wire is the weight percent). The το formulation (3) and (4) add electron-conducting materials, and the component formula (5) adds a conductive material to make the component emit blue-green light, as shown in Figures 12 to 14. The characteristics of elements VII (), VIII (·) andVIIII (Δ) are shown in Table 7. Table 7

VII VIII VIIII Starting voltage (V) 7.5 8 12 Maximum brightness (cd/m2) 320 400 24 Maximum efficiency (cd/A) 1.2(140) 1.6(115) 0.1(167)

BND

PBD 50 Obviously, many modifications and differences are possible in the present invention in light of the above description of the embodiments. It is therefore to be understood that within the scope of the appended claims, the invention may be The above is only the preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. All other equivalent changes or modifications which are not departing from the spirit of the present invention should be included in the following application. Patent Description [First Description of the Drawings] The first figure is a 'component η 冚 and current-voltage diagram according to the third example of the present invention; ~ The second figure is a third example according to the present invention, the element L n亮度和 luminance-voltage diagram; ~ The third diagram is an efficiency-voltage diagram of the elements L nm and W according to the third example of the present invention; the fourth diagram is a component according to the third example of the present invention! , an electroluminescence spectrum of n m and W;

The fifth picture is the sixth standard of the invention of the county, the current diagram of the component v; <L sixth figure is the sixth method according to the invention, the brightness of the component V_voltage 1358412; the seventh picture is according to the present In the sixth example of the invention, the efficiency-voltage diagram of the component v; the eighth diagram is the current-voltage diagram of the component VI in the sixth example of the invention, and the ninth diagram is the component in the sixth example according to the invention. The luminance-voltage diagram of VI; the tenth diagram is the efficiency-voltage diagram of the component VI in the sixth example of the present invention; and the eleventh diagram is the electroluminescence of the components V and VI in the sixth example according to the present invention. Figure 12 is a current-voltage diagram of elements VII (), VIII (v) and ν ΐΙΙΙ (Δ) in accordance with a sixth example of the present invention; and a thirteenth diagram in accordance with a sixth example of the present invention , luminance-voltage diagrams of elements VII (), VIII (parameter) and VIIII (Δ); and fourteenth diagram, in accordance with the sixth example of the invention, elements VII (), VIII (parameter) andVIIII (△) Efficiency - current density map. 52

Claims (1)

1358412 Patent Application Range: 1. A ruthenium complex having a pentacene benzene ligand, the general formula of the ruthenium complex having a pentacene benzene ligand is as follows: , R_ where G contains one of the following groups: 丨< >< :丨< < R45 R4e R10 R1 :< 丨< R26 :丨< 丨< R14 丨< R30 R54 R55- 丨<:|< < R59 53 1358412 Wherein R and R" are auxiliary ligands, and the scales 1 to 11117 may be the same or different, and are independently selected from the group consisting of: a hydrogen atom and an electron-withdrawing group. A fissile complex having a fibrew benzene ligand, wherein R' and R" are selected from one of the following groups: i-〇 = < -\-Q ' -|- 〇Λ〇〇3. As stated in the patent, the pentadyl ligand complex complex, wherein the above-mentioned electron withdrawing group comprises the lower group: the fluorine group and the trimethyl group . "If you apply for a pentadyl benzene ligand complex, it contains one of the following groups: 54 1358412 5. A ruthenium complex having a pentacene benzene ligand as claimed in claim 1 is applied to a phosphorescence element. 6. A ruthenium complex having a pentacene benzene ligand as in claim 5 of the patent application is applied to a guest material in a dish member. 7. A method for forming a ruthenium complex having a pentaphenylene ligand, the method for forming a ruthenium complex having a pentacene benzene ligand comprising: providing a first reagent, the first reagent The general formula is as follows: X1 Wherein, the Z system is a Group 5A element 'X and X2 are independently selected from one of the following groups: chlorine (C1), bromine (Br) and exchange (I), and X1 is different from X2; 55 provides a second reagent The general formula of the second reagent is as follows: R3: female b(or)2 ", medium, R is a hydrogen atom, an alkyl group or an aromatic group, and R1, R2, R3 and R4 may be the same or different' And R1, R2, R3 and R4 are independently selected from one of the following groups: a hydrogen atom and an electron withdrawing group; a Suzukl couphg reaction is made to form the first reagent and the second test sword - the middle The structure of the object is as follows: The Sonogashira coupling reaction is carried out by the acetylene group with the first intermediate to form a second intermediate having the general formula of the following: The Diels-Alder reaction is carried out with the first intermediate by tetraphenylcyclopentadienone (〇) to form a third article. The second intermediate is of the general formula: 56 1358412 The addition reaction of the ruthenium halide with the third intermediate is carried out to form a halo bridged bismuth complex, and the general formula of the bridge bismuth complex is as follows: Wherein X3 is selected from one of the group consisting of chlorine (C1), bromine (Br) and iodine (I); and a mono-substitution reaction with the halobridged bismuth complex by a chelating agent, Forming the ruthenium complex having a pentacene benzene ligand, the general formula of the ruthenium complex having a pentacene benzene ligand is as follows: 57 丄 8 of the species R6 _ from " one of the scales: • species, compounds with 9-(pentaphenylene) carbene structure The general formula of the compound of the carbazole structure is as follows: , which has 9-(pentabenzobenzene) G1 and G2 may be the same or different 'and G and G2 are independently selected from one of the following groups: a hydrogen atom, a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, .. < , corpse (〇r) 2 4-halogen atom, hydrazine, -B(〇R)2, -Ar-G3, wherein R is a hydrogen atom, a burnt group or an aromatic group, and Ar is an aromatic group. The group G3 is a gas atom, a decanoic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group. 58 1358412 9. A compound having a 9-(pentabenzophene)carbazole structure as claimed in Article 8 of the patent application, is applied to organic solar cell components. 10. A compound having a 9-(pentabenzophene)carbazole structure as claimed in item 8 of the patent application is applied to an organic electroluminescence element and/or structure. 11. A compound having a 9-(pentabenzophene)carbazole structure as claimed in claim 10 is applied to an electric electrification element and/or a phosphorescence element. A hole inject material, a hole transport material, an emitting material, or a host material. 12. A polymer derived from a 9-(pentaphenylene)carbazole structure, which comprises at least one compound having a 9-(pentaphenylbenzene) catalyzed structure as in claim 8 The reactive monomers are formed by mutual reaction, and the reactive single system is selected from one of the following groups: 59 1358412 Wherein 'R1::^^ and "" are independently selected from one of the following groups: alkyl and aromatic groups, G4 is a halogen atom, -B(〇R)2, B, 〇^\Q=^ , 'K dp(〇R) 2 , a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, wherein R is a halogen atom, a hospital group or an aromatic group. The polymer derived from the 9th (pentaphenylbenzene) carbazole structure of the 12th item is applied to organic solar cell elements. 14. 9-(pentaphenylene) card as in the 12th item of the application The polymer derived from the ruthenium structure is applied to a dectr luminescence element and/or a phosphorescence element. 15. 9-(pentabenzobenzene) as claimed in claim 14 The polymer derived from the card saliva structure is applied to a hole injecting material (hole injecting material) and a hole conducting material in an organic electroluminescence element and/or a phosphorescence element. Material), luminescent material or main illuminant material (h〇stmaterial) 16. The method for forming 9-(pentaphenyl)carazole comprises the steps of: providing a carbomer compound and a bis-carbyl compound, a ruthenium compound and the bis-halogen compound As follows: Wherein X1 and X2 may be the same or different, and χ^χ2 is independently selected from one of the following groups: gas (C1), bromine (Br) and iodine (1); and enthalpy-displacement reaction to make the card Forming a first intermediate with the bis-based compound, the structural formula is as follows: - 中 'X is independently selected from one of the following groups: chlorine (C1), spot iodine (I); s〇n〇gashira Cqingling anti-heart 乂 by epi-acetylene with the first intermediate Forming a second intermediate - the second intermediate is of the general formula: The Diels_Alder reaction is carried out with the second intermediate by tetraphenylcyclopentadienone (1358412 TPCDO) to form 9-(pentaphenyl)carazole, and the structural formula is as follows: 17. A compound having a core structure of 2-(pentaphenylbenzene)biphenyl having the general formula of a compound having a core structure of 2_(penta-phenylene)biphenyl as follows: G1 and G2 may be the same or different, and Gi and g2 are independently selected from one of the following groups: a hydrogen atom, a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, a halogen atom, 〇&gt ;,_B(〇r)2 ύ尸(〇R)2 -Ar-G3, wherein R is a hydrogen atom, an alkyl group or an aromatic group, Ar is an aromatic group, and g3 is a hydrogen atom, a decanoic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond. Group. 18. A polymer derived from the core structure of 2-(pentaphenylbenzene)biphenyl, which is obtained by the use of . 62 1358412 » φ · • i patent!_ Item 17 has 2 (pentabenzene) The chemical constituents of the biphenyl core structure are formed by reacting with at least one reactive monomer, and the reactive single system is selected from one of the following groups: —V G4 Si- ', RR, R, R and R5 are independently selected from one of the following groups: calcined / B group and aromatic group, G4 is i atom, -b(or) 2 丨 (〇r a carboxylic acid group, a hydroxyl group, an amine group, a double bond group or a triple bond group, wherein R is a hydrogen atom, a thief or an aromatic group. The 19th tree invites the southern molecule derived from the 2-(pentaphenyl)biphenyl core structure of the 18th patent range, which is applied to organic solar cell components. 63 1358412 20. The knife is derived from the organic electroluminescence (electr〇iuininescence) element and/or the phosphorescence (2) of the biphenyl core structure of the 2_ (five stupid) biphenyls. ) in the component. 21. The polymer derived from the core structure of 2-(pentaphenyl)biphenyl according to item 20 of the patent application is applied to an organic electroluminescence element and/or a phosphorescence element. A hole injection material, a hole transport material, an emitting material, or a host material. 64