KR20140043224A - Novel compounds and organic light emitting device display comprising the same - Google Patents

Abstract

The present invention is a compound represented as chemical formula 1 and an organic electroluminescent device comprising the same.

Description

Novel compounds and organic light emitting device comprising the same {NOVEL COMPOUNDS AND ORGANIC LIGHT EMITTING DEVICE DISPLAY COMPRISING THE SAME}

The present invention relates to a novel compound and an organic electroluminescent device comprising the same.

Since 1987, Eastman Kodak's Tang et al. Announced the organic thin film electroluminescent device having a laminated structure having an amorphous light emitting layer capable of low voltage driving and high luminance light emission, and has replaced the CRT as an organic light emitting display device. The research and development of the used display device is actively performed. An organic light emitting display device is a self-luminous display device including an anode, a cathode, and an organic light emitting layer positioned between them, and the display device using the organic light emitting device can be driven with low power consumption.

In realizing a full-color display in such a display device, it is necessary to use three primary colors (red, green, blue) light emitting materials having high luminous efficiency, color purity, and reliability. Among them, the green light emitting material has been studied for the longest time since the publication of Tang et al., And various methods have been proposed to improve the light emitting efficiency. For example, a device structure constituting the light emitting layer using a light emitting material in which a coumarin derivative, a quinacridone derivative, or a pyran derivative is added as a dopant to a host material composed of Alq ₃ has been proposed (J. Appl. Phys. ( 1989), vol. 65, p. 3610). In the device structure in which Alq ₃ was doped with DMQA (N, N'-dimethyl-quinacridone) and used as a light emitting layer, the light emitting efficiency of 6 to 8 Cd / A, half-life of 7000 to 8000 h (initial luminance of about 1400 Cd / m 2) Has been reported (see App1. Phys. Lett. (1997), Vol. 70, p. 1665).

However, in the conventional organic EL device, the half life (100,000 hours or more (initial luminance of 1000 to 150 Cd / m 2)) required for the realization of the display device has not been satisfied, and the light emitting efficiency and reliability are still insufficient. .

SUMMARY OF THE INVENTION An object of the present invention is to provide a compound which can be applied to an organic light emitting device to lower the driving voltage and improve luminous efficiency, brightness, thermal stability, and device life.

An object of the present invention to provide an organic light emitting device using the compound.

The present invention provides a compound represented by the following formula (1): < EMI ID =

≪ Formula 1 >

In Formula 1,

R ₁ , R ₂ and R ₃ may be the same as or different from each other, and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; A substituted or unsubstituted (C1-C60) alkyl group; A substituted or unsubstituted (C6-C60) aryl group; A substituted or unsubstituted (C5-C60) heteroaryl group; 5- or 6-membered heterocycloalkyl groups containing one or two or more selected from N, O, S and Si; Substituted or unsubstituted (C3-C60) cycloalkyl; Substituted or unsubstituted tri (C1-C60) alkylsilyl group; A substituted or unsubstituted di (C1-C60) alkyl (C6-C60) arylsilyl group; A substituted or unsubstituted tri (C6-C60) arylsilyl group; A substituted or unsubstituted (C7-C60) bicycloalkyl group; Substituted or unsubstituted (C2-C60) alkenyl group; Substituted or unsubstituted (C2-C60) alkynyl group; A substituted or unsubstituted (C1-C60) alkoxy group; A substituted or unsubstituted (C1-C60) alkylamino group; A substituted or unsubstituted (C6-C60) arylamino group; A substituted or unsubstituted (C6-C60) ar (C1-C60) alkyl group; Substituted or unsubstituted (C6-C60) aryloxy group; Substituted or unsubstituted (C6-C60) arylthio group; Substituted or unsubstituted (C1-C60) Alkylthio group; A substituted or unsubstituted (C1-C60) alkoxycarbonyl group; A substituted or unsubstituted (C1-C60) alkylcarbonyl group; Or a (C6-C60) arylcarbonyl group,

R ₁ , R _2, and R ₃ may be linked to a substituted or unsubstituted (C2-C60) alkylene or (C2-C60) alkenylene containing or not containing a fused ring with an adjacent element to form an alicyclic ring, a monocyclic ring, or Polycyclic aromatic rings can be formed.

In addition, the present invention is a first electrode; An organic material layer including a compound represented by Chemical Formula 1; And it provides an organic electroluminescent device comprising a second electrode.

When the compound of the present invention is applied to an organic light emitting device, the driving voltage is lowered, and the luminous efficiency, brightness, thermal stability and device life are improved.

The compound of the present invention partially introduces an orbital by introducing a substituent at the position 2 of the core of the compound of the present invention (hereinafter referred to as carbazole), which results in an energy bandgap larger than that of the carbazole. Big. In addition, the compounds of the present invention have a larger energy bandgap than compounds in which substituents are introduced at positions other than position 2 of carbazole. Accordingly, the compound of the present invention can be used as a hole transport layer material. And when the compound of the present invention is used as a hole transport layer material, it is more suitable for phosphorescent organic electroluminescent devices.

Hereinafter, for the detailed understanding of the present invention, for example, a compound according to the present invention, a method for preparing the same, and an organic light emitting display device according to the present invention will be described. It does not limit the scope of the invention.

Ⅰ. compound

The present invention provides a compound represented by the following formula (1).

≪ Formula 1 >

In Formula 1,

R ₁ , R ₂ and R ₃ may be the same as or different from each other, and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; A substituted or unsubstituted (C1-C60) alkyl group; A substituted or unsubstituted (C6-C60) aryl group; A substituted or unsubstituted (C5-C60) heteroaryl group; 5- or 6-membered heterocycloalkyl groups containing one or two or more selected from N, O, S and Si; Substituted or unsubstituted (C3-C60) cycloalkyl; Substituted or unsubstituted tri (C1-C60) alkylsilyl group; A substituted or unsubstituted di (C1-C60) alkyl (C6-C60) arylsilyl group; A substituted or unsubstituted tri (C6-C60) arylsilyl group; A substituted or unsubstituted (C7-C60) bicycloalkyl group; Substituted or unsubstituted (C2-C60) alkenyl group; Substituted or unsubstituted (C2-C60) alkynyl group; A substituted or unsubstituted (C1-C60) alkoxy group; A substituted or unsubstituted (C1-C60) alkylamino group; A substituted or unsubstituted (C6-C60) arylamino group; A substituted or unsubstituted (C6-C60) ar (C1-C60) alkyl group; Substituted or unsubstituted (C6-C60) aryloxy group; Substituted or unsubstituted (C6-C60) arylthio group; Substituted or unsubstituted (C1-C60) Alkylthio group; A substituted or unsubstituted (C1-C60) alkoxycarbonyl group; A substituted or unsubstituted (C1-C60) alkylcarbonyl group; Or a (C6-C60) arylcarbonyl group,

R ₁ , R _2, and R ₃ may be linked to a substituted or unsubstituted (C2-C60) alkylene or (C2-C60) alkenylene containing or not containing a fused ring with an adjacent element to form an alicyclic ring, a monocyclic ring, or Polycyclic aromatic rings can be formed.

,

,

,

,

,

,

또는

이고,Preferably, R ₁ , R ₂ and R ₃ may be the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted (C1-C60) alkyl group, a substituted or unsubstituted (C1-C60) aryl Groups, substituted or unsubstituted (C5-C60) heteroaryl groups, substituted or unsubstituted (C1-C60) alkylamino, substituted or unsubstituted (C6-C60) arylamino,

,

,

,

,

,

,

or

ego,

X ₄ to X ₁₂ may be the same as or different from each other, and each independently C, N, O, unsubstituted or substituted with (C1-C10) alkyl, (C1-C10) aryl or (C1-C10) aralkyl S or Si,

R ₄ to R ₇ may be the same as or different from each other, and each independently hydrogen, a (C1-C60) alkyl group, a (C1-C60) alkoxy group or a (C6-C60) aryl group,

Each of R ₄ to R ₇ may be independently connected to an adjacent element to form an alicyclic ring, a monocyclic ring, or a polycyclic aromatic ring.

When the substituents associated with the compound represented by Formula 1 are substituted, each independently, hydrogen; (C1-C60) alkyl group; (C6-C60) aryl group; (C1-C60) alkylsilyl group; (C1-C60) arylsilyl group; (C7-C60) arylalkyl group; (C7-C60) alkylaryl group; (C6-C60) aryloxy group; 5- or 6-membered heterocycloalkyl groups including one or two selected from N, O, S and Si; Or a (C4-C60) condensed polycyclic group. Here, each substituent may be the same or different from each other.

로 치환된 것이 보다 바람직하다. 여기서, X₁₃는 (C1-C10)알킬, (C1-C10)아릴 또는 (C1-C10)아르알킬로 치환 또는 비치환된 C, N, O, S 또는 Si일 수 있다.
Among these, when the (C1-C60) alkyl group, (C1-C60) aryl group, (C5-C60) heteroaryl group or (C6-C60) arylamino is substituted, CF ₃ , halogen atom, cyano, ( C1-C60) alkyl group, (C1-C60) alkoxy group, substituted or unsubstituted (C6-C60) aryl group, or

It is more preferable to substitute by. Here, X ₁₃ may be C, N, O, S or Si unsubstituted or substituted with (C1-C10) alkyl, (C1-C10) aryl or (C1-C10) aralkyl.

Meanwhile, in the present invention, alkyl, alkoxy and other alkyl-related substituents mean a straight or branched chain form.

In the present invention, aryl is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring system containing 4 to 7, preferably 5 or 6 ring atoms in each ring is appropriate. Include. Preferably phenyl, biphenyl, terphenyl, naphthalenyl, binapthyl, anthracenyl, phenanthrenyl, chrysenyl, naphthacenyl, indenyl, fluorenyl, acenaphthylyl, fluoanthenyl, triphenylenyl , Penalenyl, pyrenyl, peryleneyl, naphthacenyl, indenophenanthrenyl, and the like, but are not limited thereto.

The aryl may be one part of a double bond to form a ring is reduced to a single bond. For example, dihydroacenaphthylyl, tetrahydronaphthyl, dihydroanthracenyl, dihydropyrenyl, etc. can be mentioned, It is not limited to this.

In the present invention, heteroaryl means an aryl group containing one or two or more heteroatoms selected from N, O, S and Si as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It is a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group condensed with one or more benzene rings, and may be partially saturated. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, pyranyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, tri Monocyclic heteroaryl such as aziyl, tetrazinyl, triazolyl, terterzolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, isobenzofuranyl, benzoimidazolyl, benzo Thiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, dibenzofuranyl, dibenzothiophenyl, isoindoleyl, indolyl, indazolyl, benzothiadiazole, quinolyl, isoquinolyl, cinnoline Polycyclic heteroaryls such as nil, quinazolinyl, quinolizinyl, quinoxalinyl, carbazolyl, phenantridinyl, benzodioxolyl and their corresponding N-oxide quaternary salts thereof, and the like, and the like It doesn't work.

The aryl or heteroaryl substituents exemplified above may be applied as R1, R2, R3 substituents of the present invention by forming a compound compound in which two or more of them are bonded by a single bond. Substituents in the form of the complex ring compound include, for example, phenylnaphthalenyl, phenylphenanthrenyl, phenylanthracenyl, naphthalenylanthracenyl, phenylfluorenyl, naphthalenylfluorenyl, phenylcarbazolyl, naphthalenylcarba Sleepy, and the like.

More preferably, R ₁ , R ₂ and R ₃ may be the same as or different from each other, and may each independently be one of substituents represented by the following structural formulas:

More specific examples of the compound represented by Formula 1 may be as follows. However, the present invention is not limited thereto.

The compound of the present invention partially introduces an orbital by introducing a substituent at the position 2 of the core of the compound of the present invention (hereinafter referred to as carbazole), which results in an energy bandgap larger than that of the carbazole. Big. In addition, the compounds of the present invention have a larger energy bandgap than compounds in which substituents are introduced at positions other than position 2 of carbazole. Accordingly, the compound of the present invention can be used as a hole transport layer material. And when the compound of the present invention is used as a hole transport layer material, it is more suitable for phosphorescent organic electroluminescent devices.

Ⅱ. Organic electroluminescent device

The organic light emitting display device of the present invention comprises: a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including the compound represented by Chemical Formula 1.

The organic layer preferably includes a light emitting layer and a hole transport layer comprising a compound represented by the formula (1). The hole transport layer including the compound represented by Chemical Formula 1 is more suitable for phosphorescent organic light emitting devices.

The organic layer may further include one selected from the group consisting of arylamine-based compounds, styrylarylamine-based compounds, and mixtures thereof.

The organic material layer may further include one or two or more selected from the group consisting of group 1, group 2, 4 cycles, 5 cycle transition metals, lanthanide-based metals and organic metals of d-transition elements.

The organic light emitting device may further include one or more layers of a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, if necessary, the organic layers of the two layers if necessary It is also possible to form.

For example, the organic light emitting display device according to the present invention may include a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode or first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron. It may have an injection layer / second electrode structure. Alternatively, the organic light emitting display device may have a single film / light emitting layer / electron transport layer / second electrode or a first electrode / hole injection function and a hole transport function and a single film / having a hole transport function. It may have a light emitting layer / electron transport layer / electron injection layer / second electrode structure.

The organic light emitting display device according to the present invention can be applied in various structures such as a top emission type and a bottom emission type.

The manufacturing method of the organic electroluminescent device according to the present invention will be described below by taking an organic electroluminescent device having a structure of a first electrode / hole injection layer / hole transport layer / electron transport layer / sperm transport layer / second electrode as an example.

First, a first electrode material having a high work function on the substrate is formed by a deposition method, a sputtering method, or the like to form a first electrode. The first electrode may be an anode or a cathode. Herein, a substrate used in a conventional organic electroluminescent device is used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), Al, Ag, mg, etc. having excellent conductivity may be used. Or a reflective electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are usually appropriately selected in the range of 10 to 5 mu m.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. What is the heat treatment temperature for removing solvent after coating? It is preferable to select suitably from the temperature range of 200-200 degree.

As the hole injection layer material, a well-known hole injection layer material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429, or Advanced Material, 6, p.677 (1994). TCTA, m-MTDATA, m-MTDAPB, starburst amine derivatives, and polyaniline / dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4) -ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline) / Poly (4-styrene-sulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like can be used.

The hole injection layer may have a thickness of about 100 to 10000 mm 3, preferably 100 to 1000 mm 3. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Next, a hole transport layer (HTL) is formed on the hole injection layer by using the compounds of the present invention by various methods such as vacuum deposition, spin coating, casting, and LB. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may further use a known hole transport layer material. For example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, 4,4'-bis [N- (1-naphthyl) ) -N-phenylamino] biphenyl (NPB), N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD And the formation of an injection layer in which a conventional amine derivative having an aromatic condensed ring such as N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) is used. It is selected from the same condition range.

Next, a light emitting layer is formed on the hole transport layer. Formation of the organic film is usually carried out by a vacuum deposition method. In this case, the organic layer may be a light emitting layer of a host-dopant system. As a representative example of the host-dopant system, a tris (8-hydroxyquinoline) aluminum (III): Alq) exemplified in the embodiment of the present invention may be a host-C545T system. It is not limited to this. The thickness of the light emitting layer to be deposited may be adjusted within the range of 100 to 1,000Å.

An electron transport layer and an electron injection layer may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

The electron transport layer may also use a known material. Examples of the electron transport layer material known in the art include, but are not limited to, Balq, Alq, Liq, and the like. The thickness of the electron transport layer is typically 10 to 500Å, the thickness can be adjusted.

As the material of the electron injection layer, for example, LiF is representatively used in the art, but the present invention is not limited thereto.

The electron injection layer may have a thickness of about 1 to 100 kPa, preferably 5 to 90 kPa. This is because, when the thickness of the electron injection layer is less than 1 kV, the electron injection characteristic may be degraded, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a method such as vacuum deposition or sputtering. The second electrode may be used as a cathode or an anode. As the material for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples include lithium (Li), magnesium (mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (mg-In), magnesium-silver (mg-Ag), and the like. Can be mentioned. In addition, a transparent cathode using ITO and IZO may be used to obtain a top light emitting device.

The organic light emitting display device according to the present invention may be provided in various types of flat panel display devices, for example, passive matrix organic light emitting display devices and active matrix organic light emitting display devices. In particular, when provided in the active matrix organic light emitting display device, the first electrode provided on the substrate side may be electrically connected to the source electrode or the drain electrode of the thin film transistor as the pixel electrode. In addition, the organic light emitting display device may be provided in a flat panel display that can display a screen on both sides.

When the compound of the present invention is applied to an organic light emitting device, the driving voltage is lowered, and the luminous efficiency, brightness, thermal stability and device life are improved.

Ⅲ. Organic solar cell

The organic solar cell of the present invention includes a compound represented by Chemical Formula 1. Except for including the compound represented by the formula (1) has the same structure as a known organic solar cell.

Hereinafter, the synthesis examples and examples of the compound represented by the formula (1) of the present invention will be specifically illustrated, but the present invention is not limited to the following examples.

Synthetic example  1: Preparation of compound 1

Compound 1 was synthesized through the reaction route of Chemical Scheme 1 below.

<Reaction Scheme 1>

(1) Preparation of Compound 1-1

)(72%, 7.85g)을 얻었다.
2-bromocarbazole (6 g, 24.38 mmol), 2-bromopyrene (12 g, 36.57 mmol), K ₂ CO ₃ (250 ml in a round bottom flask in nitrogen atmosphere) 10.11 g, 73.14 mmol), Cu powder (1.55 g, 24.39 mmol) and 18-crown-6 (3.22 g, 12.19 mmol) were added to o-dichlorobenzene (o -dichlorobenzene) and refluxed for 24 hours. After the reaction was completed, the organic layer obtained by extraction with methylene chloride and water was washed with 10% hydrochloric acid and brine. The reaction mixture was dried over MgSO ₄ , concentrated under reduced pressure, separated by column chromatography, and the compound 1-1 (R ₁ :

) (72%, 7.85 g).

(2) Preparation of Compound 1-2

)(80%, 5.61g)을 얻었다.
In 250 ml of two necked round bottom flasks Compound 1-1 (7 g, 15.73 mmol) was diluted in THF and lowered to -78? And n-BuLi (14.7 ml, 1.6 M in hexane solution) was slowly dropped. After stirring for 1 hour, trimethyl borate (2.63 ml, 23.6 mmol) was added thereto, followed by stirring at room temperature for 24 hours. After the reaction was completed, the reaction was terminated with distilled water at 0 ℃ and 6M HCl was dropped. After extraction of the reaction product with dichloromethane (3x20ml), the organic layer obtained was dried over MgSO ₄ , concentrated under reduced pressure and separated by column chromatography to give the compound 1-2 (R ₁ :

) (80%, 5.61 g).

(3) Preparation of Compound 1-3

)(83%, 5.91g)을 얻었다.
In a 250 mL round bottom flask, compound 1-2 (5.61 g, 13.64 mmol), 1-bromo-4-iodobenzene (3.86 g, 13.64 mmol), Pd (PPh ₃ ) ₄ (785 mg, 0.68 mmol, 5 mol%) and Na ₂ SO ₄ (2.89 g, 27.28 mmol) were dissolved in toluene / distilled water (60 mL / 15 mL) and refluxed at 100 ° C. for 24 hours. After the reaction was completed, the organic layer was separated, and the water layer was extracted with dichloromethane (3 × 15 mL). The reaction mixture was dried over MgSO ₄ , concentrated under reduced pressure, separated by column chromatography, and the compound 1-3 (R ₁ :

) (83%, 5.91 g).

(4) Preparation of Final Compound

, R₂:

, R₃:

)(74%, 4.89g)을 얻었다.
In a nitrogen atmosphere, 250 ml of a round bottom flask was placed compound 1-3 (5.61 g, 10.74 mmol), diphenylamine (1.78 g, 10.74 mmol), Pd ₂ (dba) ₃ (979 mg, 1.07 m). Mol), PPh ₃ (561 mg, 2.14 mmol), NaOt-bu (5.1 g, 53.7 mmol) and toluene (80 mL) were added and refluxed at 100 ° C for 24 hours. After the reaction was completed, the organic layer was separated, and the water layer was extracted with dichloromethane (3 × 15 mL). The reaction mixture was dried over MgSO ₄ , concentrated under reduced pressure, separated by column chromatography to obtain Compound 1 (R ₁ :

, R ₂ :

, R ₃ :

) (74%, 4.89 g).

Synthetic example  2: Preparation of compound 5

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 5의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) was carried out in the same manner except that N-phenylphenanthren-3-amine was used instead of diphenylamine. Proceeded. Accordingly, Compound 5 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 5 is shown in Table 1 below.

Synthetic example  3: Preparation of Compound 10

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 10의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, `(4) Preparation of Final Compound`, 4- (9,9-dimethyl-9H-fluoren-1-yl) -N-phenylamine (4- (instead of diphenylamine) Synthesis was carried out in the same manner except for using 9,9-dimethyl-9H-fluoren-1-yl) -N-phenylamine). Accordingly, Compound 10 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 10 is shown in Table 1 below.

Synthetic example  4: Preparation of Compound 15

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 15의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, `(4) Preparation of Final Compound`, instead of diphenylamine, N, 9-diphenyl-9H-carbazole-3-amine (N, 9-diphenyl-9H-carbazol-3 Synthesis was performed in the same manner except for using -amine). Accordingly, Compound 15 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 15 is shown in Table 1 below.

Synthetic example  5: Preparation of Compound 20

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 20의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, in Preparation of Final Compound (4), synthesis was carried out in the same manner except for using N-phenylnaphthalen-1-amine instead of diphenylamine. It was. Accordingly, Compound 20 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 20 is shown in Table 1 below.

Synthetic example  6: Preparation of Compound 25

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 25의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, in Preparation of Final Compound (4), 11,11-dimethyl-N-phenyl-11H-benzo [b] fluorene-1-amine (11,11- Synthesis was performed in the same manner except for using dimethyl-N-phenyl-11H-benzo [b] fluoren-1-amine). Accordingly, Compound 25 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 25 is shown in Table 1 below.

Synthetic example  7: Preparation of Compound 30

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 30의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1 in Preparation of Final Compound (4), N- (naphthalen-2-yl) anthracene-2-amine (N- (naphthalen-2-yl) anthracen-2 instead of diphenylamine) Synthesis was performed in the same manner except for using -amine). Accordingly, Compound 30 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 30 is shown in Table 1 below.

Synthetic example  8: Preparation of Compound 35

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 35의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1 in Preparation of Final Compound (4), 9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluorene-3-amine (9, Synthesis was carried out in the same manner except for using 9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-3-amine). Accordingly, Compound 35 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 35 is shown in Table 1 below.

Synthetic example  9: Preparation of Compound 40

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 40의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) 9,9-dimethyl-N- (naphthalen-2-yl) -9,10-dihydroanthracene-2-amine instead of diphenylamine Synthesis was carried out in the same manner except for using (9,9-dimethyl-N- (naphthalen-2-yl) -9,10-dihydroanthracen-2-amine). Accordingly, Compound 40 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 40 is shown in Table 1 below.

Synthetic example  10: Preparation of Compound 45

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 45의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) Instead of diphenylamine, N- (naphthalen-2-yl) phenanthrene-9-amine (N- (naphthalen-2-yl) phenanthren- Synthesis was performed in the same manner except for using 9-amine). Accordingly, Compound 45 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 45 is shown in Table 1 below.

Synthetic example  11: Preparation of Compound 50

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 50의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) 13,13-dimethyl-N- (naphthalen-2-yl) -13H-indeno [1,2-l] instead of diphenylamine Synthesis was performed in the same manner except for using phenanthrene-10-amine (13,13-dimethyl-N- (naphthalen-2-yl) -13H-indeno [1,2-l] phenanthren-10-amine). . Accordingly, Compound 50 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 50 is shown in Table 1 below.

Synthetic example  12: Preparation of Compound 55

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 55의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 13,13-dimethyl-N- (naphthalen-2-yl) -13H-indeno [1,2- instead of diphenylamine l] Synthesis was carried out in the same manner except for using phenanthrene-10-amine (13,13-dimethyl-N- (naphthalen-2-yl) -13H-indeno [1,2-l] phenanthren-10-amine). Proceeded. Accordingly, Compound 55 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 55 is shown in Table 1 below.

Synthetic example  13: Preparation of Compound 60

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 60의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H instead of diphenylamine Synthesis was carried out in the same manner except for using -fluorene-3-amine (N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-3-amine). . Accordingly, Compound 60 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 60 is shown in Table 1 below.

Synthetic example  14: Preparation of Compound 65

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 65의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) Instead of diphenylamine, N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9,10 Synthesis by the same method, except that dihydroanthracene-2-amine (N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9,10-dihydroanthracen-2-amine) was used. Proceeded. Accordingly, Compound 65 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 65 is shown in Table 1 below.

Synthetic example  15: Preparation of Compound 70

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 70의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, Preparation of Final Compound (4) was carried out in the same manner except for using di (anthracen-2-yl) amine instead of diphenylamine. Synthesis was performed. Accordingly, Compound 70 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 70 is shown in Table 1 below.

Synthetic example  16: Preparation of Compound 75

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 75의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (9,9-dimethyl-9H-fluoren-3-yl) anthracene-2-amine (N Synthesis was performed in the same manner except that-(9,9-dimethyl-9H-fluoren-3-yl) anthracen-2-amine) was used. Accordingly, compound 75 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 75 is shown in Table 1 below.

Synthetic example  17: Preparation of Compound 80

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 80의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9,10-dihydroanthransen-2-yl) anthracene- in place of diphenylamine Synthesis was performed in the same manner except that 2-amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) anthracen-2-amine) was used. Accordingly, Compound 80 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 80 is shown in Table 1 below.

Synthetic example  18: Preparation of Compound 85

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 85의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of final compound`, N- (phenanthren-9-yl) anthracene-2-amine (N- (phenanthren-9-yl) instead of diphenylamine Synthesis was performed in the same manner except for using anthracen-2-amine. Accordingly, Compound 85 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 85 is shown in Table 1 below.

Synthetic example  19: Preparation of Compound 90

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 90의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (anthracen-2-yl) -13,13-dimethyl-13H-indeno [1,2- l] Synthesis was carried out in the same manner except for using phenanthrene-10-amine (N- (anthracen-2-yl) -13,13-dimethyl-13H-indeno [1,2-l] phenanthren-10-amine). Proceeded. Accordingly, Compound 90 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 90 is shown in Table 1 below.

Synthetic example  20: Preparation of Compound 95

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 95의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (phenanthren-3-yl) pyren-2-amine (N- (phenanthren-3-yl) instead of diphenylamine Synthesis was performed in the same manner except that pyren-2-amine) was used. Accordingly, Compound 95 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 95 is shown in Table 1 below.

Synthetic example  21: Preparation of Compound 100

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 100의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (phenanthren-3-yl) dibenzo [b, d] thiophen-4-amine (N instead of diphenylamine) Synthesis was performed in the same manner except that-(phenanthren-3-yl) dibenzo [b, d] thiophen-4-amine) was used. Accordingly, Compound 100 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 100 is shown in Table 1 below.

Synthetic example  22: Preparation of Compound 105

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 105의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (8-phenylnaphthalen-2-yl) phenanthrene-3-amine (N- (8-phenylnaphthalen) instead of diphenylamine -2-yl) phenanthren-3-amine) was synthesized in the same manner. Accordingly, Compound 105 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 105 is shown in Table 1 below.

Synthetic example  23: Preparation of Compound 110

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 110의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-([1,1'-biphenyl] -3-yl) phenanthrene-3-amine (N instead of diphenylamine) Synthesis was performed in the same manner except that-([1,1'-biphenyl] -3-yl) phenanthren-3-amine) was used. Accordingly, Compound 110 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 110 is shown in Table 1 below.

Synthetic example  24: Preparation of Compound 115

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 115의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (3- (naphthalen-2-yl) phenyl) phenanthrene-3-amine (N- (3) instead of diphenylamine Synthesis was performed in the same manner except that-(naphthalen-2-yl) phenyl) phenanthren-3-amine) was used. Accordingly, Compound 115 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 115 is shown in Table 1 below.

Synthetic example  25: Preparation of Compound 120

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 120의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9H-fluoren-3-yl) pyren-2-amine (N instead of diphenylamine) Synthesis was performed in the same manner except that-(9,9-dimethyl-9H-fluoren-3-yl) pyren-2-amine) was used. Accordingly, Compound 120 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 120 is shown in Table 1 below.

Synthetic example  26: Preparation of Compound 125

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 125의 NMR은 하기 표 1에 기재하였다.
In the preparation method of (4) the final compound in the synthesis method of Synthesis Example 1, N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) pyrene-2- instead of diphenylamine Synthesis was performed in the same manner except that amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) pyren-2-amine) was used. Accordingly, Compound 125 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 125 is shown in Table 1 below.

Synthetic example  27: Preparation of Compound 130

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 130의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (phenanthren-9-yl) pyren-2-amine (N- (phenanthren-9-yl) instead of diphenylamine Synthesis was performed in the same manner except that pyren-2-amine) was used. Accordingly, Compound 130 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 130 is shown in Table 1 below.

Synthetic example  28: Preparation of Compound 135

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 135의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 13,13-dimethyl-N- (pyren-2-yl) -13H-indeno [1,2- instead of diphenylamine l] Synthesis was performed in the same manner except for using phenanthrene-10-amine (13,13-dimethyl-N- (pyren-2-yl) -13H-indeno [1,2-l] phenanthren-10-amine). Proceeded. Accordingly, Compound 135 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 135 is shown in Table 1 below.

Synthetic example  29: Preparation of Compound 140

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 140의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (4- (naphthalen-1-yl) phenyl) -7-phenylnaphthalen-2-amine (N Synthesis was performed in the same manner except that-(4- (naphthalen-1-yl) phenyl) -7-phenylnaphthalen-2-amine) was used. Accordingly, Compound 140 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 140 is shown in Table 1 below.

Synthetic example  30: Preparation of Compound 145

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 145의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 9,9-dimethyl-N- (4- (naphthalen-1-yl) phenyl) -7-phenyl- instead of diphenylamine Synthesis was carried out in the same manner except for using 9H-fluorene-3-amine (9,9-dimethyl-N- (4- (naphthalen-1-yl) phenyl) -7-phenyl-9H-fluoren-3-amine) Proceeded. Accordingly, Compound 145 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 145 is shown in Table 1 below.

Synthetic example  31: Preparation of Compound 150

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 150의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 9- (naphthalen-1-yl) -N- (4- (naphthalen-1-yl) phenyl)-instead of diphenylamine Synthesis was carried out in the same manner, except that 9H-carbazole-3-amine (9- (naphthalen-1-yl) -N- (4- (naphthalen-1-yl) phenyl) -9H-carbazol-3-amine) was used. Proceeded. Accordingly, Compound 150 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 150 is shown in Table 1 below.

Synthetic example  32: Preparation of Compound 155

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 155의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl) pyren-1-amine (N- (4- Synthesis was performed in the same manner except that (naphthalen-1-yl) phenyl) pyren-1-amine) was used. Accordingly, Compound 155 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 155 is shown in Table 1 below.

Synthetic example  33: Preparation of Compound 160

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 160의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, bis (7-phenylnaphthalen-2-yl) amine (bis (7-phenylnaphthalen-2-yl) amine) instead of diphenylamine Synthesis was carried out in the same manner except using. Accordingly, Compound 160 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 160 is shown in Table 1 below.

Synthetic example  34: Preparation of Compound 165

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out by the same method except that 1-bromophenanthrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 165의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N, 9,9-trimethyl-7-phenyl-N- (7-phenylnaphthalen-2-yl)- Synthesis was carried out in the same manner except for using 9H-fluorene-3-amine (N, 9,9-trimethyl-7-phenyl-N- (7-phenylnaphthalen-2-yl) -9H-fluoren-3-amine). Proceeded. Accordingly, Compound 165 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 165 is shown in Table 1 below.

Synthetic example  35: Preparation of Compound 170

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 170의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 9- (naphthalen-1-yl) -N- (7-phenylnaphthalen-2-yl) -9H- instead of diphenylamine Carbazole-3-amine (9- (naphthalen-1-yl) -N- (7-phenylnaphthalen-2-yl) -9H-carbazol-3-amine) was synthesized in the same manner. Accordingly, compound 170 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 170 is shown in Table 1 below.

Synthetic example  36: Preparation of Compound 175

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 175의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (7-phenylnaphthalen-2-yl) pyren-1-amine (N- (7-phenylnaphthalen- Synthesis was performed in the same manner except that 2-yl) pyren-1-amine) was used. Accordingly, Compound 175 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 175 is shown in Table 1 below.

Synthetic example  37: Preparation of Compound 180

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 180의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, bis (9,9-dimethyl-9H-fluoren-3-yl) amine (bis (9,9- Synthesis was performed in the same manner except that dimethyl-9H-fluoren-3-yl) amine) was used. Accordingly, Compound 180 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 180 is shown in Table 1 below.

Synthetic example  38: Preparation of Compound 185

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 185의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (9,9-dimethyl-9H-fluoren-3-yl) -9,9-dimethyl- Except for using 9,10-dihydroanthracene-2-amine (N- (9,9-dimethyl-9H-fluoren-3-yl) -9,9-dimethyl-9,10-dihydroanthracen-2-amine) Synthesis was carried out in the same manner. Accordingly, Compound 185 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 185 is shown in Table 1 below.

Synthetic example  39: Preparation of Compound 190

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 190의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9H-fluoren-3-yl) phenanthrene-9-amine (instead of diphenylamine) Synthesis was performed in the same manner except that N- (9,9-dimethyl-9H-fluoren-3-yl) phenanthren-9-amine) was used. Accordingly, Compound 190 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 190 is shown in Table 1 below.

Synthetic example  40: Preparation of Compound 195

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 195의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (9,9-dimethyl-9H-fluoren-3-yl) -13,13-dimethyl- 13H-indeno [1,2-l] phenanthrene-10-amine (N- (9,9-dimethyl-9H-fluoren-3-yl) -13,13-dimethyl-13H-indeno [1,2- l] phenanthren-10-amine) was synthesized in the same manner except for using. Accordingly, Compound 195 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 195 is shown in Table 1 below.

Synthetic example  41: Preparation of Compound 200

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 200의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (dibenzo [b, d] thiophen-4-yl) dibenzo [b, d] furan instead of diphenylamine Synthesis was carried out in the same manner except that 4-amine (N- (dibenzo [b, d] thiophen-4-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 200 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 200 is shown in Table 1 below.

Synthetic example  42: Preparation of Compound 205

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 205의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Phenyl) dibenzo [b, d] thiophen-4-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) dibenzo [b, d] thiophen- Synthesis was performed in the same manner except using 4-amine). Accordingly, Compound 205 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 205 is shown in Table 1 below.

Synthetic example  43: Preparation of Compound 210

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromopyrene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 210의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of final compound`, N- (anthracen-1-yl) dibenzo [b, d] thiophen-4-amine (N- Synthesis was performed in the same manner except that (anthracen-1-yl) dibenzo [b, d] thiophen-4-amine) was used. Accordingly, Compound 210 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 210 is shown in Table 1 below.

Synthetic example  44: Preparation of Compound 215

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 215의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (5-phenylnaphthalen-2-yl) dibenzo [b, d] thiophen-4-amine instead of diphenylamine Synthesis was carried out in the same manner except that (N- (5-phenylnaphthalen-2-yl) dibenzo [b, d] thiophen-4-amine) was used. Accordingly, Compound 215 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 215 is shown in Table 1 below.

Synthetic example  45: Preparation of Compound 220

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 220의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (8-phenylnaphthalen-2-yl) dibenzo [b, d] furan-4-amine (instead of diphenylamine) Synthesis was performed in the same manner except that N- (8-phenylnaphthalen-2-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 220 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 220 is shown in Table 1 below.

Synthetic example  46: Preparation of Compound 225

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 225의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-([1,1'-biphenyl] -3-yl) dibenzo [b, d] furan instead of diphenylamine Synthesis was carried out in the same manner except that 4-amine (N-([1,1'-biphenyl] -3-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 225 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 225 is shown in Table 1 below.

Synthetic example  47: Preparation of Compound 230

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 230의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (3- (naphthalen-2-yl) phenyl) dibenzo [b, d] furan-4- instead of diphenylamine Synthesis was carried out in the same manner except for using amine (N- (3- (naphthalen-2-yl) phenyl) dibenzo [b, d] furan-4-amine). Accordingly, Compound 230 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 230 is shown in Table 1 below.

Synthetic example  48: Preparation of Compound 235

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 235의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Phenyl) -9,9-dimethyl-9,10-dihydroanthracene-2-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) -9, 9-dimethyl-9,10-dihydroanthracen-2-amine) was synthesized in the same manner except for using. Accordingly, Compound 235 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 235 is shown in Table 1 below.

Synthetic example  49: Preparation of Compound 240

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 240의 NMR은 하기 표 1에 기재하였다.
In the preparation method of (4) the final compound in the synthesis method of Synthesis Example 1, N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) anthracene-1- instead of diphenylamine Synthesis was performed in the same manner except for using amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) anthracen-1-amine). Accordingly, Compound 240 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 240 is shown in Table 1 below.

Synthetic example  50: Preparation of Compound 245

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 245의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 9,9-dimethyl-N- (5-phenylnaphthalen-2-yl) -9,10-dihydro instead of diphenylamine Synthesis was carried out in the same manner except that anthracene-2-amine (9,9-dimethyl-N- (5-phenylnaphthalen-2-yl) -9,10-dihydroanthracen-2-amine) was used. Accordingly, Compound 245 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 245 is shown in Table 1 below.

Synthetic example  51: Preparation of Compound 250

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 250의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (phenanthrene-9-yl) -9-phenyl-9H-carbazol-3-amine (N Synthesis was performed in the same manner except that-(phenanthren-9-yl) -9-phenyl-9H-carbazol-3-amine) was used. Accordingly, Compound 250 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 250 is shown in Table 1 below.

Synthetic example  52: Preparation of Compound 255

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 255의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthrene-10- Yl) -9-phenyl-9H-carbazole-3-amine (N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-10-yl) -9-phenyl-9H-carbazol- Synthesis was performed in the same manner except using 3-amine). Accordingly, Compound 255 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 255 is shown in Table 1 below.

Synthetic example  53: Preparation of Compound 260

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 260의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 9- (naphthalen-1-yl) -N- (phenanthrene-9-yl) -9H-carbazole instead of diphenylamine Synthesis was carried out in the same manner except that 3-amine (9- (naphthalen-1-yl) -N- (phenanthren-9-yl) -9H-carbazol-3-amine) was used. Accordingly, Compound 260 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 260 is shown in Table 1 below.

Synthetic example  54: Preparation of Compound 265

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 265의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthrene-10- Yl) -9- (naphthalen-1-yl) -9H-carbazole-3-amine (N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-10-yl) -9- Synthesis was performed in the same manner except that (naphthalen-1-yl) -9H-carbazol-3-amine) was used. Accordingly, Compound 265 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 265 is shown in Table 1 below.

Synthetic example  55: Preparation of Compound 270

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 270의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (naphthalen-1-yl) phenanthrene-9-amine (N- (naphthalen-1-yl) instead of diphenylamine Synthesis was performed in the same manner except for using phenanthren-9-amine). Accordingly, Compound 270 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 270 is shown in Table 1 below.

Synthetic example  56: Preparation of Compound 275

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 275의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 11,11-dimethyl-N- (phenanthrene-9-yl) -11H-benzo [b] fluorene instead of diphenylamine Synthesis was performed in the same manner except for using -1-amine (11,11-dimethyl-N- (phenanthren-9-yl) -11H-benzo [b] fluoren-1-amine). Accordingly, Compound 275 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 275 is shown in Table 1 below.

Synthetic example  57: Preparation of Compound 280

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromoanthracene (1-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 280의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, 11,11-dimethyl-N- (pyren-1-yl) -11H-benzo [b] fluorene- Synthesis was carried out in the same manner except that 1-amine (11,11-dimethyl-N- (pyren-1-yl) -11H-benzo [b] fluoren-1-amine) was used. Accordingly, Compound 280 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 280 is shown in Table 1 below.

Synthetic example  58: Preparation of Compound 285

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 285의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-phenyl- [1,1'-biphenyl] -4-amine (N-phenyl- [1, Synthesis was performed in the same manner except that 1'-biphenyl] -4-amine) was used. Accordingly, Compound 285 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 285 is shown in Table 1 below.

Synthetic example  59: Preparation of Compound 290

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 290의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, '(4) Preparation of the final compound', using N, 7-diphenylnaphthalen-2-amine (N, 7-diphenylnaphthalen-2-amine) instead of diphenylamine. Other synthesis was carried out in the same manner. Accordingly, Compound 290 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 290 is shown in Table 1 below.

Synthetic example  60: Preparation of Compound 295

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 295의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, instead of diphenylamine 9,9-dimethyl-N, 7-diphenyl-9H-fluorene-3-amine (9,9 -dimethyl-N, 7-diphenyl-9H-fluoren-3-amine) was synthesized in the same manner except for using. Accordingly, Compound 295 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 295 is shown in Table 1 below.

Synthetic example  61: Preparation of Compound 300

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 300의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, 9- (naphthalen-1-yl) -N-phenyl-9H-carbazol-3-amine (9- Synthesis was performed in the same manner except that (naphthalen-1-yl) -N-phenyl-9H-carbazol-3-amine) was used. Accordingly, Compound 300 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 300 is shown in Table 1 below.

Synthetic example  62: Preparation of Compound 305

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 305의 NMR은 하기 표 1에 기재하였다.
In Synthesis of Synthesis Example 1, in Preparation of Final Compound (4), synthesis was carried out in the same manner except for using N-phenylpyren-1-amine instead of diphenylamine. Proceeded. Thus, Compound 305 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 305 is shown in Table 1 below.

Synthetic example  63: Preparation of Compound 310

)를 수득하였다. In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 310의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, in the preparation of the final compound (4), the same procedure was used except that di (naphthalen-2-yl) amine was used instead of diphenylamine. Synthesis was carried out by the method. Accordingly, compound 310 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 310 is shown in Table 1 below.

Synthetic example  64: Preparation of Compound 315

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 315의 NMR은 하기 표 1에 기재하였다.
In the preparation method of (4) the final compound in the synthesis method of Synthesis Example 1, N- (4- (naphthalen-1-yl) phenyl) naphthalen-2-amine (N- (4- Synthesis was carried out in the same manner except for using (naphthalen-1-yl) phenyl) naphthalen-2-amine). Accordingly, Compound 315 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 315 is shown in Table 1 below.

Synthetic example  65: Preparation of Compound 320

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 320의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (naphthalen-2-yl) dibenzo [b, d] furan-4-amine (N- ( Synthesis was performed in the same manner except that naphthalen-2-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 320 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 320 is shown in Table 1 below.

Synthetic example  66: Preparation of Compound 325

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 325의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Synthesis was carried out in the same manner except for using phenyl) naphthalen-2-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) naphthalen-2-amine). It was. Thus, Compound 325 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 325 is shown in Table 1 below.

Synthetic example  67: Preparation of Compound 330

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 330의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (naphthalen-2-yl) anthracene-1-amine (N- (naphthalen-2-yl) anthracen instead of diphenylamine) Synthesis was performed in the same manner except for using -1-amine). Accordingly, Compound 330 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 330 is shown in Table 1 below.

Synthetic example  68: Preparation of Compound 335

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 335의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, in the preparation of the final compound (4), N- (naphthalen-2-yl) -5-phenylnaphthalen-2-amine (N- (naphthalen-2) was used instead of diphenylamine. -yl) -5-phenylnaphthalen-2-amine) was synthesized in the same manner. Accordingly, Compound 335 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 335 is shown in Table 1 below.

Synthetic example  69: Preparation of Compound 340

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 340의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl)-[1,1'-biphenyl]-instead of diphenylamine Synthesis was conducted in the same manner except that 4-amine (N- (4- (naphthalen-1-yl) phenyl)-[1,1'-biphenyl] -4-amine) was used. Accordingly, Compound 340 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 340 is shown in Table 1 below.

Synthetic example  70: Preparation of Compound 345

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 1-bromonaphthalene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 345의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-([1,1'-biphenyl] -4-yl) dibenzo [b, d] furan instead of diphenylamine Synthesis was carried out in the same manner except that 4-amine (N-([1,1'-biphenyl] -4-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 345 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 345 is shown in Table 1 below.

Synthetic example  71: Preparation of Compound 350

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 350의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Phenyl)-[1,1'-biphenyl] -4-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl)-[1,1'- Synthesis was performed in the same manner except for using biphenyl] -4-amine). Accordingly, Compound 350 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 350 is shown in Table 1 below.

Synthetic example  72: Preparation of Compound 355

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 355의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl) anthracene-2-amine (N- (4- Synthesis was performed in the same manner except that (naphthalen-1-yl) phenyl) anthracen-2-amine) was used. Accordingly, Compound 355 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 355 is shown in Table 1 below.

Synthetic example  73: Preparation of Compound 360

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 360의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (anthracen-2-yl) dibenzo [b, d] furan-4-amine (N- ( Synthesis was performed in the same manner except for using anthracen-2-yl) dibenzo [b, d] furan-4-amine). Accordingly, Compound 360 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 360 is shown in Table 1 below.

Synthetic example  74: Preparation of Compound 365

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 365의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Synthesis was carried out in the same manner except for using phenyl) anthracene-2-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) anthracen-2-amine). It was. Accordingly, Compound 365 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 365 is shown in Table 1 below.

Synthetic example  75: Preparation of Compound 370

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 370의 NMR은 하기 표 1에 기재하였다.
And, in the preparation of the final compound (4) in the synthesis method of Synthesis Example 1, instead of diphenylamine N- (anthracen-2-yl) anthracene-1-amine (N- (anthracen-2-yl) anthracen Synthesis was performed in the same manner except for using -1-amine). Accordingly, Compound 370 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 370 is shown in Table 1 below.

Synthetic example  76: Preparation of Compound 375

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 375의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (5-phenylnaphthalen-2-yl) anthracene-2-amine (N- (5-phenylnaphthalen-) instead of diphenylamine Synthesis was performed in the same manner except that 2-yl) anthracen-2-amine) was used. Accordingly, Compound 375 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 375 is shown in Table 1 below.

Synthetic example  77: Preparation of Compound 380

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 380의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9H-fluoren-3-yl) phenanthrene-3-amine (instead of diphenylamine) Synthesis was performed in the same manner except for using N- (9,9-dimethyl-9H-fluoren-3-yl) phenanthren-3-amine). Accordingly, Compound 380 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 380 is shown in Table 1 below.

Synthetic example  78: Preparation of Compound 385

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 385의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) phenanthrene-3 instead of diphenylamine Synthesis was carried out in the same manner except that -amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) phenanthren-3-amine) was used. Accordingly, Compound 385 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 385 is shown in Table 1 below.

Synthetic example  79: Preparation of Compound 390

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 390의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (phenanthren-9-yl) phenanthren-3-amine (N- (phenanthren-9-yl) instead of diphenylamine Synthesis was performed in the same manner except for using phenanthren-3-amine. Accordingly, Compound 390 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 390 is shown in Table 1 below.

Synthetic example  80: Preparation of Compound 395

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 395의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 13,13-dimethyl-N- (phenanthren-3-yl) -13H-indeno [1,2 instead of diphenylamine -l] phenanthrene-10-amine (13,13-dimethyl-N- (phenanthren-3-yl) -13H-indeno [1,2-l] phenanthren-10-amine) except that Proceeded. Accordingly, compound 395 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 395 is shown in Table 1 below.

Synthetic example  81: Preparation of Compound 400

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 400의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (4- (naphthalen-1-yl) phenyl) pyren-2-amine (N- (4- Synthesis was performed in the same manner except that (naphthalen-1-yl) phenyl) pyren-2-amine) was used. Accordingly, Compound 400 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 400 is shown in Table 1 below.

Synthetic example  82: Preparation of Compound 405

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 405의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (pyren-2-yl) dibenzo [b, d] furan-4-amine (N- ( Synthesis was performed in the same manner except that pyren-2-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 405 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 405 is shown in Table 1 below.

Synthetic example  83: Preparation of Compound 410

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 410의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Synthesis was carried out in the same manner except for using phenyl) pyren-2-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) pyren-2-amine). It was. Accordingly, Compound 410 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 410 is shown in Table 1 below.

Synthetic example  84: Preparation of Compound 415

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that bromobenzene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 415의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (anthracen-1-yl) pyren-2-amine (N- (anthracen-1-yl) pyren instead of diphenylamine) Synthesis was performed in the same manner except for using -2-amine). Accordingly, Compound 415 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 415 is shown in Table 1 below.

Synthetic example  85: Preparation of Compound 420

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 420의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (anthracen-1-yl) pyren-2-amine (N- (anthracen-1-yl) pyren instead of diphenylamine) Synthesis was performed in the same manner except for using -2-amine). Accordingly, Compound 420 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 420 is shown in Table 1 below.

Synthetic example  86: Preparation of Compound 425

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 425의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl) dibenzo [b, d] thiophene-4 instead of diphenylamine Synthesis was carried out in the same manner except that -amine (N- (4- (naphthalen-1-yl) phenyl) dibenzo [b, d] thiophen-4-amine) was used. Thus, Compound 425 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 425 is shown in Table 1 below.

Synthetic example  87: Preparation of Compound 430

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 430의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (4- (naphthalen-1-yl) phenyl) -8-phenylnaphthalen-2-amine (N Synthesis was performed in the same manner except that-(4- (naphthalen-1-yl) phenyl) -8-phenylnaphthalen-2-amine) was used. Accordingly, Compound 430 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 430 is shown in Table 1 below.

Synthetic example  88: Preparation of Compound 435

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 435의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl)-[1,1'-biphenyl]-instead of diphenylamine Synthesis was carried out in the same manner except that 3-amine (N- (4- (naphthalen-1-yl) phenyl)-[1,1'-biphenyl] -3-amine) was used. Thus, Compound 435 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 435 is shown in Table 1 below.

Synthetic example  89: Preparation of Compound 440

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 440의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (naphthalen-1-yl) phenyl) -3- (naphthalen-2-yl) amine instead of diphenylamine Synthesis was carried out in the same manner except that (N- (4- (naphthalen-1-yl) phenyl) -3- (naphthalen-2-yl) amine) was used. Accordingly, Compound 440 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 440 is shown in Table 1 below.

Synthetic example  90: Preparation of Compound 445

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 445의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (7-phenylnaphthalen-2-yl) dibenzo [b, d] thiophen-4-amine instead of diphenylamine Synthesis was carried out in the same manner except for using (N- (7-phenylnaphthalen-2-yl) dibenzo [b, d] thiophen-4-amine). Accordingly, Compound 445 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 445 is shown in Table 1 below.

Synthetic example  91: Preparation of Compound 450

)를 수득하였다.In Synthesis of Synthesis Example 1, `` (4) Preparation of Compound 1-1`, except that 6-bromo-1H-phenene was used instead of 2-bromopyrene, was used. Synthesis was carried out by the method. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 450의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, instead of diphenylamine 8-phenyl-N- (7-phenylnaphthalen-2-yl) naphthalen-2-amine (8-phenyl Synthesis was performed in the same manner except that -N- (7-phenylnaphthalen-2-yl) naphthalen-2-amine) was used. Accordingly, Compound 450 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 450 is shown in Table 1 below.

Synthetic example  92: Preparation of Compound 455

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 455의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N-([1,1'-biphenyl] -3-yl) -7-phenylnaphthalene-2- instead of diphenylamine Synthesis was carried out in the same manner except that amine (N-([1,1'-biphenyl] -3-yl) -7-phenylnaphthalen-2-amine) was used. Accordingly, Compound 455 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 455 is shown in Table 1 below.

Synthetic example  93: Preparation of Compound 460

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 460의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (3- (naphthalen-2-yl) phenyl) -7-phenylnaphthalen-2-amine (N Synthesis was performed in the same manner except that-(3- (naphthalen-2-yl) phenyl) -7-phenylnaphthalen-2-amine) was used. Accordingly, Compound 460 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 460 is shown in Table 1 below.

Synthetic example  94: Preparation of Compound 465

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 465의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9H-fluoren-3-yl) dibenzo [b, d] instead of diphenylamine Synthesis was performed in the same manner except using furan-4-amine (N- (9,9-dimethyl-9H-fluoren-3-yl) dibenzo [b, d] furan-4-amine). Accordingly, Compound 465 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 465 is shown in Table 1 below.

Synthetic example  95: Preparation of Compound 470

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 470의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Phenyl) -9,9-dimethyl-9H-fluorene-3-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) -9,9-dimethyl -9H-fluoren-3-amine) was synthesized in the same manner except for using. Accordingly, Compound 470 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 470 is shown in Table 1 below.

Synthetic example  96: Preparation of Compound 475

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 475의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9H-fluoren-3-yl) anthracene-1-amine (N instead of diphenylamine) Synthesis was performed in the same manner except that-(9,9-dimethyl-9H-fluoren-3-yl) anthracen-1-amine) was used. Accordingly, Compound 475 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 475 is shown in Table 1 below.

Synthetic example  97: Preparation of Compound 480

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 480의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, 9,9-dimethyl-N- (5-phenylnaphthalen-2-yl) -9H-fluorene-3 instead of diphenylamine Synthesis was performed in the same manner except that -amine (9,9-dimethyl-N- (5-phenylnaphthalen-2-yl) -9H-fluoren-3-amine) was used. Accordingly, Compound 480 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 480 is shown in Table 1 below.

Synthetic example  98: Preparation of Compound 485

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1) 4-1, 4-bromo-1,1'-biphenyl instead of 2-bromopyrene (4-bromo-1,1'-biphenyl The synthesis was carried out in the same manner except for using). Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 485의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (dibenzo [b, d] thiophen-4-yl) -9-phenyl-9H-carba instead of diphenylamine Synthesis was performed in the same manner except that sol-3-amine (N- (dibenzo [b, d] thiophen-4-yl) -9-phenyl-9H-carbazol-3-amine) was used. Accordingly, Compound 485 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 485 is shown in Table 1 below.

Synthetic example  99: Preparation of Compound 490

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 490의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (naphthalen-1-yl) dibenzo [b, d] thiophen-4-amine (N- Synthesis was performed in the same manner except that (naphthalen-1-yl) dibenzo [b, d] thiophen-4-amine) was used. Accordingly, Compound 490 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 490 is shown in Table 1 below.

Synthetic example  100: Preparation of Compound 495

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 495의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (11,11-dimethyl-11H-benzo [b] fluoren-1-yl) dibenzo [ same method except for using b, d] thiophen-4-amine (N- (11,11-dimethyl-11H-benzo [b] fluoren-1-yl) dibenzo [b, d] thiophen-4-amine) Synthesis was carried out. Accordingly, Compound 495 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 495 is shown in Table 1 below.

Synthetic example  101: Preparation of Compound 500

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 500의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) dibenzo [b instead of diphenylamine , d] furan-4-amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) dibenzo [b, d] furan-4-amine) was synthesized in the same manner. It was. Accordingly, Compound 500 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 500 is shown in Table 1 below.

Synthetic example  102: Preparation of Compound 505

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 505의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (phenanthren-9-yl) dibenzo [b, d] furan-4-amine (N- Synthesis was carried out in the same manner, except that (phenanthren-9-yl) dibenzo [b, d] furan-4-amine) was used. Accordingly, Compound 505 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 505 is shown in Table 1 below.

Synthetic example  103: Preparation of Compound 510

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 510의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthrene-10- I) dibenzo [b, d] furan-4-amine (N- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-10-yl) dibenzo [b, d] furan-4- Synthesis was performed in the same manner except for using amine). Accordingly, Compound 510 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 510 is shown in Table 1 below.

Synthetic example  104: Preparation of Compound 515

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 9-bromoanthracene (9-bromoanthracene) was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 515의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) -9-phenyl instead of diphenylamine Synthesis by the same method except for using -9H-carbazole-3-amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) -9-phenyl-9H-carbazol-3-amine) Proceeded. Accordingly, Compound 515 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 515 is shown in Table 1 below.

Synthetic example  105: Preparation of Compound 520

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 520의 NMR은 하기 표 1에 기재하였다.
And, in the '(4) Preparation of the final compound` in the synthesis method of Synthesis Example 1, instead of diphenylamine 9,9-dimethyl-N- (naphthalen-1-yl) -9,10-dihydroanthracene-2 Synthesis was carried out in the same manner except that -amine (9,9-dimethyl-N- (naphthalen-1-yl) -9,10-dihydroanthracen-2-amine) was used. Accordingly, Compound 520 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 520 is shown in Table 1 below.

Synthetic example  106: Preparation of Compound 525

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 525의 NMR은 하기 표 1에 기재하였다.
And, in the preparation of the final compound (4) in the synthesis method of Synthesis Example 1, instead of diphenylamine N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) -11,11 Dimethyl-11H-benzo [b] fluoren-1-amine (N- (9,9-dimethyl-9,10-dihydroanthracen-2-yl) -11,11-dimethyl-11H-benzo [b] fluoren- Synthesis was performed in the same manner except for using 1-amine). Accordingly, Compound 525 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 525 is shown in Table 1 below.

Synthetic example  107: Preparation of the compound 530

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 530의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) instead of diphenylamine Phenyl) -9-phenyl-9H-carbazole-3-amine (N- (4- (9,9-dimethyl-7-phenyl-9H-fluoren-1-yl) phenyl) -9-phenyl-9H-carbazol Synthesis was carried out in the same manner except for using -3-amine). Accordingly, Compound 530 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 530 is shown in Table 1 below.

Synthetic example  108: Preparation of Compound 535

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 535의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, instead of diphenylamine, N- (anthracen-1-yl) -9-phenyl-9H-carbazole-3-amine (N- Synthesis was carried out in the same manner except that (anthracen-1-yl) -9-phenyl-9H-carbazol-3-amine) was used. Accordingly, Compound 535 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 535 is shown in Table 1 below.

Synthetic example  109: Preparation of Compound 540

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 540의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 9-phenyl-N- (5-phenylnaphthalen-2-yl) -9H-carbazole-3-amine instead of diphenylamine Synthesis was carried out in the same manner except that (9-phenyl-N- (5-phenylnaphthalen-2-yl) -9H-carbazol-3-amine) was used. Accordingly, Compound 540 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 540 is shown in Table 1 below.

Synthetic example  110: Preparation of Compound 545

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 545의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of Final Compound`, N- (anthracen-1-yl) -9- (naphthalen-1-yl) -9H-carbazole- instead of diphenylamine Synthesis was performed in the same manner except that 3-amine (N- (anthracen-1-yl) -9- (naphthalen-1-yl) -9H-carbazol-3-amine) was used. Accordingly, Compound 545 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 545 is shown in Table 1 below.

Synthetic example  111: Preparation of Compound 550

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 550의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of the final compound`, 9- (naphthalen-1-yl) -N- (5-phenylnaphthalen-2-yl) -9H- instead of diphenylamine Carbazole-3-amine (9- (naphthalen-1-yl) -N- (5-phenylnaphthalen-2-yl) -9H-carbazol-3-amine) was synthesized in the same manner. Thus, Compound 550 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 550 is shown in Table 1 below.

Synthetic example  112: Preparation of Compound 555

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 555의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, `(4) Preparation of final compound`, N- (phenanthren-9-yl) pyren-1-amine (N- (phenanthren-9-yl) instead of diphenylamine Synthesis was performed in the same manner except using pyren-1-amine). Accordingly, Compound 555 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 555 is shown in Table 1 below.

Synthetic example  113: Preparation of Compound 560

)를 수득하였다.In Synthesis of Synthesis Example 1, Preparation of Compound (1-1) was carried out in the same manner except that 2-bromoanthracene was used instead of 2-bromopyrene. Thus, compound 1-1 (R ₁ :

).

, R₂:

, R₃:

)를 수득하였다. 상기 화합물 560의 NMR은 하기 표 1에 기재하였다.
In the synthesis method of Synthesis Example 1, in the `preparation of the final compound (4)`, except that di (pyren-1-yl) amine (di (pyren-1-yl) amine) was used instead of diphenylamine, Synthesis was carried out by the method. Accordingly, Compound 560 (R ₁ :

, R ₂ :

, R ₃ :

). NMR of the compound 560 is shown in Table 1 below.

compound _{^{1 H NMR (CDCl 3, 200Mz}} ) MS / FAB found calculated One δ = 8.55 (1H, dd), 8.18 (1H, d), 8.0 (4H, m), 7.94 (1H, dd), 7.8-7.79 (2H, m), 7.7 (4H, s), 7.62 (1H, s), 7.54 (2H, d), 7.2 to 7.33 (6H, m), 6.81 (2H, m), 6.81 (2H, t), 6.69 (2H, d), 6.63 (4H, d) 610.74 610.44 5 8.93 (1H, dd), 8.55 (1H, dd), 8.18-8.12 (3H, m), 8.0-7.71 (11H, m), 7.7 (4H, s), 7.54 (2H, dd), 7.33-7.2 ( 4H, m), 7.02 (1H, d), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d) 710.86 710.27 10 8.55 (1H, dd), 8.18 (1H, d), 7.79-8.00 (9H, m), 7.70-7.71 (4H, s), 7.62 (1H, s), 7.53-7.55 (6H, m), 7.20- 7.44 (7H, m), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 1.72 (6H, s) 803.00 802.33 15 8.55 (1H, dd), 8.18 (1H, d), 8.0 (4H, m), 7.94 (2H, dd), 7.8-7.79 (2H, m), 7.71 (4H, s), 7.58-7.29 (15H, m), 6.81-6.75 (3H, m), 6.69 (2H, d), 6.63 (2H, d) 775.93 775.30 20 8.55 (1H, dd), 8.18 (1H, d), 7.94 ~ 8.07 (7H, m), 7.70 ~ 7.79 (6H, m), 7.53 ~ 7.62 (6H, m), 7.20 ~ 7.38 (5H, m), 6.98 (1H, d), 6.81 (1H, m), 6.69 (2H, d), 6.63 (2H, d) 660.80 660.26 25 8.55 (1H, dd), 8.28 (1H, s), 8.18 (1H, d), 7.94-8.01 (7H, m), 7.79-7.80 (2H, m), 770-7.71 (4H, m), 7.52- 7.62 (6H, m), 7.45 (1H, m), 7.19-7.33 (5H, m), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d) , 1.78 (6H, s) 776.96 776.32 30 8.55 (1H, dd), 8.19 (2H, dd), 8.08 (1H, t), 8.0-7.74 (14H, m), 7.71 (4H, s), 7.62 (1H, s), 7.54-7.49 (4H, m), 7.39 to 7.25 (5H, m), 7.03 (1H, s), 6.83 (1H, d), 6.69 (2H, d), 760.92 760.29 35 8.55 (1H, dd), 8.18 (1H, d), 8.0-7.74 (12H, m), 7.7 (4H, s), 7.62 (1H, s), 7.55-7.49 (4H, m), 7.38-7.25 ( 6H, m), 7.04 (1H, s), 6.69 (2H, d), 6.48 (1H, d), 1.72 (6H, s) 776.96 776.32 40 8.56 (1H, dd), 8.18 (1H, d), 8.0-7.74 (11H, m), 7.71 (4H, s), 7.62 (1H, s), 7.54-7.49 (4H, m), 7.36-7.19 ( 7H, m), 7.06 (1H, d), 6.69 (2H, d), 6.51 (1H, s), 6.39 (1H, d), 3.91 (2H, s), 1.72 (6H, s) 790.99 790.33 45 8.93 (2H, dd), 8.55 (1H, dd), 8.18 (1H, d), 8.12 (2H.d) 7.71-8.00 (19H, m), 7.62 (1H, s), 7.49-7.54 (4H, m ), 7.25-7.36 (3H, m), 6.91 (1H, s), 6.69 (2H, d) 760.92 760.29 50 8.93 (2H, dd), 8.55 (1H, dd), 8.18 (1H, d), 8.12 (2H.d) 7.71-8.00 (19H, m), 7.62 (1H, s), 7.49-7.54 (4H, m ), 7.25-7.36 (5H, m), 6.69 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 877.08 876.35 55 8.55 (1H, dd), 8.18 ~ 8.19 (2H, d), 8.08 (1H, t), 7.91 ~ 7.94 (3H, m), 7.75 ~ 7.79 (2H, m), 7.25 ~ 7.58 (18H, m), 7.03 (1H, t), 6.83 (1H, d), 6.69 (4H, d) 662.82 662.27 60 8.56 (1H, dd), 8.18 (1H, d), 7.94 (1H, dd), 7.87 (1H, dd), 7.79 (1H, dd), 7.62-7.25 (21H, m), 7.04 (1H, s) , 6.69 (4H, d), 6.48 (1H, d), 1.72 (6H, s) 678.86 678.3 65 8.55 (1H, dd), 8.18 (1H, d), 8.00 (4H, m), 7.94 (1H, dd), 7.79-7.78 (2H, m), 7.70-7.71 (4H, s), 7.62 (1H, s), 7.19-7.54 (15H, m), 7.06 (1H, d), 6.69 (4H, d), 6.51 (1H, s), 6.39 (1H, d), 1.72 (6H, s) 817.03 816.35 70 8.55 (1H, dd), 8.18-8.19 (3H, m), 7.70-8.08 (19H, m), 7.62 (1H, s), 7.54 (2H, dd), 7.25-7.39 (6H, m), 7.03 ( 2H, s), 6.83 (2H, dd), 6.69 (2H, dd) 810.98 810.30 75 8.9 (2H, d), 8.55 (1H, dd), 8.19 ~ 8.1 (4H, m), 7.94 ~ 7.7 (12H, m), 7.39 ~ 7.25 (7H, m), 7.04 ~ 7.03 (2H, m), 6.83 (1H, d), 6.69 (2H, d), 6.48 (1H, d), 1.72 (6H, s) 803.00 802.33 80 8.9 (2H, d), 8.55 (1H, dd), 7.94 ~ 7.75 (11H, m), 7.62 (1H, s), 7.54 (2H, d), 7.39 ~ 7.19 (8H, m), 7.06 (1H, d), 7.03 (1H, d), 6.83 (1H, d), 6.69 (2H, d), 6.51 (1H, s), 3.91 (2H, s), 1.72 (6H, s) 817.03 816.35 85 8.90 ~ 8.93 (4H, dd), 8.55 (1H, dd), 8.08 ~ 8.19 (6H, m), 7.70 ~ 7.94 (15H, m), 7.62 (1H, s), 7.54 (2H, dd), 7.25 ~ 7.39 (4H, m), 7.03 (1H, s), 6.91 (1H, s), 6.83 (2H, dd), 6.69 (2H, dd) 786.96 786.30 90 8.93 (2H, dd), 8.55 (1H, dd), 8.08-8.18 (6H, m), 7.70-7.94 (15H, m), 7.62 (1H, s), 7.54 (2H, dd), 7.25-7.39 ( 6H, m), 7.03 (1H, s), 6.83 (1H, dd), 6.69 (2H, d), 6.44 (1H, d) 903.12 902.37 95 8.90-8.83 (3H, dd), 8.55 (1H, dd), 8.10-8.18 (4H, m), 7.70-8.00 (20H, m), 7.62 (1H, s), 7.54 (2H, d), 7.20- 7.33 (4H, m), 7.02 (1H, d), 6.69 (2H, d) 810.98 810.98 100 8.9 (2H, d), 8.55 (1H, dd), 8.45 (1H, d), 8.18-8.1 (4H, m), 7.98-7.7 (11H, m), 7.71 (4H, s), 7.62 (1H, s), 7.54 ~ 7.5 (4H, m), 7.33 ~ 7.25 (3H, m), 7.02 (1H, d), 6.86 (1H, m), 6.69 (2H, d) 792.98 792.26 105 8.90 ~ 8.93 (3H, dd), 8.55 (1H, dd), 8.33 (1H, d), 8.10 ~ 8.18 (4H, m), 7.70 ~ 7.94 (17H, m), 7.62 (1H, s), 7.19 ~ 7.54 (9H, m), 7.02 (1H, d), 6.80 (1H, s), 6.69 (2H, d) 812.99 812.32 110 8.90-8.83 (3H, dd), 8.55 (1H, dd), 8.10-8.18 (4H, m), 7.70-7.94 (13H, m), 7.62 (1H, s), 7.25-7.54 (10H, m), 7.02 (1H, d), 6.88-6.89 (2H, m), 6.69 (2H, d), 6.59 (1H, d) 762.94 762.30 115 8.90-8.83 (3H, dd), 8.55 (1H, dd), 8.10-8.18 (4H, m), 7.70-8.00 (17H, m), 7.54-7.82 (6H, m), 7.44 (1H, t), 7.25-7.33 (2H, m), 7.02 (1H, dd), 6.88-6.89 (2H, t), 6.69 (2H, d), 6.59 (1H, d) 812.99 812.32 120 8.9 (2H, dd), 8.55 (1H, dd), 8.18 (1H, d), 8.1 (1H, d), 8.0 (2H, d), 7.94-7.79 (8H, m), 7.7 (6H, s) , 7.62 (1H, s), 7.55 ~ 7.54 (3H, m), 7.38 ~ 7.25 (5H, m), 7.20 (2H, s), 7.04 (1H, m), 6.69 (2H, d), 6.48 (1H , dd), 1.72 (6H, s) 827.02 826.33 125 8.9 (2H, dd), 8.55 (1H, dd), 8.10-8.18 (2H, m), 7.70-8.00 (15H, m), 7.62 (1H, s), 7.54 (2H, m), 7.19-7.33 ( 8H, m), 7.06 (1H, dd), 6.69 (2H, dd), 6.51 (1H, s), 6.39 (1H, dd), 3.91 (2H, s), 1.72 (6H, s) 841.05 840.35 130 8.9 ~ 8.93 (4H, dd), 8.55 (1H, dd), 8.1 ~ 8.12 (4H, m), 7.7 ~ 8.00 (19H, m), 7.62 (1H, s), 7.54 (2H, m), 7.33 ~ 7.25 (2H, m), 7.20 (2H, s), 6.91 (1H, s), 6.69 (2H, d) 810.98 810.30 135 8.9 ~ 8.93 (4H, dd), 8.55 (1H, dd), 8.1 ~ 8.18 (4H, m), 7.7 ~ 8.00 (19H, m), 7.62 (1H, s), 7.54 (2H, d), 7.33 ~ 7.25 (2H, m), 7.20 (2H, s), 6.69 (2H, d), 6.44 (1H, d) 927.14 926.37 140 8.9 (2H, dd), 8.55 (2H, m), 8.42 (1H, dd), 8.1-8.18 (4H, m), 7.7-7.74 (11H, m), 7.25-7.82 (18H, m), 6.69 ( 4H, dd) 839.03 838.33 145 8.9 (2H, dd), 8.55 (1H, m), 8.42 (1H, dd), 8.04 ~ 8.18 (4H, m), 7.77 ~ 7.94 (8H, m), 7.7 (2H, s), 7.25 ~ 7.62 ( 17H, m), 7.04 (1H, s), 6.69 (4H, dd), 6.48 (1H, d) 905.13 904.38 150 8.9 (2H, dd), 8.56 (3H, m), 8.42 (1H, d), 8.18-8.04 (7H, m), 7.94-7.8 (7H, m), 7.71 (2H, s), 7.62-7.53 ( 12H, m), 7.39-7.25 (5H, m), 6.77 (1H, d), 6.75 (1H, s), 6.69 (4H, d), 928.13 927.36 155 8.9 (2H, dd), 8.55 (2H, m), 8.42 (1H, dd), 8.04 ~ 8.18 (5H, m), 7.7 ~ 7.94 (15H, m), 7.54 ~ 7.62 (8H, m), 7.25 ~ 7.33 (2H, m), 7.02 (1H, d), 6.69 (4H, d) 837.02 836.32 160 8.9 (2H, dd), 8.55 (1H, dd), 8.18 (1H, d), 8.1 (1H, d), 7.94-7.74 (14H, m), 7.62 (1H, s), 7.54-7.25 (20H, m), 6.69 (2H, d) 839.09 838.33 165 8.91 (2H, dd), 8.56 (1H, dd), 8.18 (1H, d), 8.1 (1H, d), 7.94-7.74 (11H, m), 7.7 (2H, s), 7.62 (1H, s) , 7.54 ~ 7.25 (18H, m), 7.04 (1H, s), 6.69 (2H, d), 6.48 (1H, d), 1.72 (6H, s) 905.14 904.38 170 8.55 (2H, dd), 8.18 (1H, d), 8.1 ~ 8.08 (5H, m), 7.94 (2H, m), 7.9 ~ 7.74 (7H, m), 7.7 (4H, s), 7.55 ~ 7.25 ( 20H, m), 6.77 (1H, d), 6.75 (1H, s), 6.69 (2H, d) 952.15 951.36 175 8.55 (1H, dd), 8.1-8.18 (4H, m), 7.7-7.74 (19H, m), 7.62 (1H, s), 7.25-7.54 (12H, m), 7.02 (1H, d), 6.69 ( 1H, d) 861.04 860.32 180 8.55 (1H, dd), 8.18 (1H, d), 8.1 (2H, d), 7.94-7.79 (7H, m), 7.7 (4H, s), 7.62 (1H, s), 7.55-7.54 (4H, ddd), 7.38-7.25 (8H, m), 7.04 (2H, s), 6.69 (2H, d), 6.48 (2H, d), 1.72 (6H, s) 843.06 842.37 185 8.55 (1H, dd), 8.18 (1H, d), 8.1 (2H, d), 7.94-7.74 (6H, m), 7.7 (4H, s), 7.62 (1H, s), 7.55-7.54 (3H, m), 7.38-7.25 (9H, m), 7.06 (1H, dd), 7.04 (1H, s), 6.69 (2H, d), 6.51-6.68 (2H, m), 6.39 (1H, d), 3.91 (2H, s), 1.72 (6H, s) 857.09 856.38 190 8.93 (2H, dd), 8.55 (1H, dd), 8.1 ~ 8.18 (5H, m), 7.7 ~ 7.94 (14H, m), 7.62 (1H, s), 7.54 ~ 7.55 (3H, m), 7.25 ~ 7.38 (5H, m), 7.04 (1H, s), 6.91 (1H, s), 6.69 (2H, d), 6.48 (1H, dd), 1.72 (6H, s) 827.02 826.33 195 8.93 (2H, dd), 8.55 (1H, dd), 8.1 ~ 8.18 (5H, m), 7.7 ~ 7.94 (14H, m), 7.62 (1H, s), 7.54 ~ 7.55 (3H, m), 7.25 ~ 7.38 (7H, m), 7.04 (1H, s), 6.69 (2H, d), 6.44-6.68 (2H, m), 1.85 (6H, s), 1.72 (6H, s) 943.18 942.40 200 8.55 (1H, dd), 8.45 (1H, m), 8.18 (1H, d), 8.1 (2H, d), 7.98-7.79 (8H, m), 7.71-7.7 (4H, s), 7.66-7.72 ( 2H, m), 7.5-7.54 (2H, m), 7.38-7.25 (6H, m), 7.07 (1H, t), 6.86 (1H, dd), 6.69 (2H, d), 6.39 (1H, dd) 806.97 806.24 210 8.55 (1H, dd), 8.45 (1H, m), 8.30 (1H, s), 8.25 (1H, s), 8.18 (1H, d), 8.1 (2H, d), 7.98-7.79 (9H, m) , 7.71 (4H, s), 7.62 (1H, s), 7.54 ~ 7.5 (4H, m), 7.4 ~ 7.22 (7H, m), 6.86 (1H, dd), 6.69 (2H, d), 6.62 (1H , d) 817.01 816.26 215 8.55 (1H, dd), 8.45 (1H, m), 8.3 (2H, s), 8.19-8.18 (2H, m), 7.98-7.9 (6H, m), 7.79-7.81 (5H, m), 7.62 ( 1H, s), 7.54-7.19 (16H, m), 6.86 (1H, d), 6.80 (1H, s), 6.69 (2H, d) 819.02 818.28 220 8.55 (1H, dd), 8.3 ~ 8.33 (3H, m), 8.18 (1H, d), 7.89 ~ 7.94 (6H, m), 7.77 ~ 7.79 (4H, m), 7.62 ~ 7.66 (2H, m), 7.51 to 7.54 (4H, m), 7.19 to 7.41 (12H, m), 7.07 (1H, t), 6.80 (1H, s), 6.69 (2H, d), 6.39 (1H, dd) 802.96 802.30 225 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 7.89 ~ 7.94 (5H, m), 7.79 (1H, d), 7.62 ~ 7.66 (2H, m), 7.25 ~ 7.54 ( 17H, m), 7.07 (1H, t), 6.88-6.89 (2H, d), 6.69 (2H, d), 6.59 (1H, dd), 6.39 (1H, dd) 752.90 752.28 230 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 8.00-7.89 (8H, m), 7.79-7.54 (9H, m), 7.44-7.25 (10H, m), 7.07 ( 1H, t), 6.89 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.59 (1H, d), 6.39 (1H, dd) 802.96 802.30 235 8.55 (1H, dd), 8.33 (2H, s), 8.18 (1H, d), 7.9 ~ 7.94 (5H, m), 7.77 ~ 7.83 (3H, m), 7.62 ~ 7.63 (2H, d), 7.19 ~ 7.54 (21H, m), 7.06 (1H, d), 6.69 (4H, d), 6.51 (1H, s), 6.39 (1H, dd), 3.91 (2H, s), 1.72 (6H, s) 985.26 984.44 240 8.55 (1H, dd), 8.25-8.30 (4H, m), 8.18 (1H, d), 7.9-7.94 (6H, m), 7.79 (1H, dd), 7.62 (1H, s), 7.54 (2H, d), 7.19-7.40 (14H, m), 7.06 (1H, d), 6.69 (2H, d), 6.62 (1H, d). 6.51 (1H, s), 6.39 (1H, d), 3.91 (2H, s), 1.72 (6H, s) 817.03 816.35 245 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 7.94-7.9 (5H, m), 7.79-7.81 (4H, m), 7.62 (1H, s), 7.54-7.51 ( 5H, m), 7.41-7.19 (12H, m), 7.06 (1H, d), 6.8 (1H, s), 6.69 (2H, d), 6.51 (1H, s), 6.39 (2H, d), 3.91 (2H, s), 1.72 (6H, s) 843.06 842.37 250 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 8.12-8.18 (4H, m), 7.79-7.74 (9H, m), 7.25-7.69 (19H, m), 6.91 ( 1H, s), 6.69 (2H, d), 5.93 (1H, d) 852.03 851.33 255 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 8.12-8.18 (4H, m), 7.79-7.74 (9H, m), 7.25-7.69 (21H, m), 6.69 ( 2H, d), 6.44 (1H, dd), 5.93 (1H, dd) 968.19 967.39 260 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 8.08 ~ 8.18 (7H, m), 7.79 ~ 7.94 (9H, m), 7.50 ~ 7.69 (11H, m), 7.25 ~ 7.4 (7H, m), 6.91 (1H, s), 6.69 (2H, d), 5.93 (1H, dd) 902.09 901.35 265 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 8.08 ~ 8.18 (7H, m), 7.79 ~ 7.94 (9H, m), 7.50 ~ 7.69 (11H, m), 7.25 ~ 7.4 (9H, m), 6.69 (2H, d), 6.44 (1H, dd), 5.93 (1H, dd), 1.85 (6H, s) 1018.25 1017.41 270 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 7.82-8.18 (14H, m), 7.53-7.82 (6H, m), 7.25-7.4 (7H, m), 6.98 ( 1H, dd), 6.91 (1H, s), 6.69 (2H, d) 736.90 736.29 275 8.93 (2H, dd), 8.55 (1H, dd), 8.28-8.3 (3H, m), 8.12-8.18 (3H, m), 7.79-8.01 (11H, m), 7.52-7.82 (6H, m), 7.19-7.45 (8H, m), 6.91 (1H, s), 6.69 (2H, d), 6.44 (1H, dd), 1.78 (6H, s) 853.06 852.35 280 8.55 (1H, dd), 8.3 (2H, s), 8.28 (1H, s), 8.18 (1H, d), 8.12 (1H, d), 7.97-7.79 (10H, m), 7.71 (4H, s) , 7.62 (1H, s), 7.58 ~ 7.54 (5H, m), 7.45 (1H, d), 7.4 ~ 7.19 (7H, m), 7.02 (1H, d), 6.69 (2H, d), 6.44 (1H , dd), 1.78 (6H, s) 877.08 876.35 285 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.94 (1H, d), 7.79 (1H, d), 7.62 (1H, s), 7.60-7.51 (15H, m) , 7.41-7.20 (5H, m), 6.81 (1H, t), 6.69 (4H, d), 6.63 (2H, d) 612.78 612.26 290 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.94 (1H, d), 7.74-7.84 (4H, m), 7.20-7.82 (19H, m), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, dd) 662.82 662.27 295 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.93-7.74 (2H, m), 7.77-7.79 (2H, m), 7.20-7.63 (18H, m), 7.04 ( 1H, s), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, dd), 6.48 (1H, dd), 1.72 (6H, s) 728.92 728.32 300 8.55 (2H, dd), 8.18 (1H, d), 8.08 (6H, m), 7.94 (2H, dd), 7.79 (1H, dd), 7.54-7.82 (11H, m), 7.20-7.38 (7H, m), 6.81-6.75 (3H, m), 6.69 (2H, d), 6.63 (2H, dd) 751.91 751.30 305 8.55 (1H, dd), 8.18 (1H, d), 8.12-8.08 (4H, m), 7.94 (1H, d), 7.88-7.79 (4H, m), 7.71 (4H, s), 7.62 (1H, s), 7.60-7.54 (6H, m), 7.33-7.20 (4H, m), 7.02 (1H, d), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d) 660.80 660.26 310 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.74-7.74 (10H, m), 7.49-7.82 (11H, m), 7.25-7.36 (4H, m), 6.69 ( 2H, d) 636.78 636.26 315 8.55 (2H, m), 8.42 (1H, dd), 8.18 (1H, d), 8.04 ~ 8.08 (5H, m), 7.74 ~ 7.94 (6H, m), 7.49 ~ 7.62 (14H, m), 7.25 ~ 7.36 (3H, m), 6.69 (4H, d) 712.88 712.39 320 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.89-7.74 (7H, m), 7.62-7.49 (10H, m), 7.36-7.25 (6H, m), 7.07 ( 1H, t), 6.69 (2H, d), 6.39 (1H, d) 676.80 676.25 325 8.55 (1H, dd), 8.18 (1H, d), 8.08 (3H, m), 7.74-7.94 (9H, m), 7.25-7.63 (22H, m), 6.69 (4H, d), 1.72 (6H, s) 855.07 854.37 330 8.55 (1H, dd), 8.30 (1H, s), 8.25 (1H, s), 8.08 (3H, m), 7.74-7.74 (8H, m), 7.49-7.82 (9H, m), 7.22-7.40 ( 7H, m), 6.69 (2H, d), 6.62 (1H, dd) 686.84 686.27 335 8.55 (1H, dd), 8.18 ~ 8.19 (2H, m), 8.08 (3H, m), 7.74 ~ 7.94 (10H, m), 7.19 ~ 7.60 (17H, m), 6.80 (1H, t), 6.69 ( 2H, d) 712.88 712.29 340 8.55 (2H, m), 8.42 (1H, dd), 8.18 (1H, d), 8.04-8.08 (5H, m), 7.94 (1H, dd), 7.79 (1H, dd), 7.51-7.82 (18H, m), 7.25-7.41 (3H, m), 6.69 (6H, d) 738.91 738.30 345 8.55 (2H, doublet), 8.18 (2H, d), 8.08 (3H, m). 7.89 ~ 7.94 (2H, m), 7.79 (1H, dd), 7.25 ~ 7.66 (20H, m), 7.07 (1H, t), 6.69 (4H, d), 6.39 (1H, dd) 702.84 702.27 350 8.55 (1H, dd), 8.18 (1H, d), 7.93-7.74 (2H, m), 7.77-7.83 (3H, m), 7.25-7.63 (27H, m), 6.69 (6H, d), 1.72 ( 6H, s) 831.05 830.37 355 8.55 (2H, m), 8.42 (1H, dd), 8.18-8.19 (2H, d), 8.04-8.08 (3H, m), 7.91-7.94 (3H, m), 7.75-7.79 (2H, m), 7.25 to 7.72 (17H, m), 7.03 (1H, t), 6.83 (2H, dd), 6.69 (4H, d) 712.88 712.29 360 8.55 (1H, dd), 8.19-8.18 (2H, d), 8.08 (1H, s), 7.94-7.89 (4H, m), 7.79-7.75 (2H, dd), 7.62-7.25 (16H, m), 7.07 (1H, t), 7.03 (1H, s), 6.83 (1H, d), 6.69 (2H, d), 6.39 (1H, d) 676.80 676.25 365 8.55 (1H, dd), 8.18 ~ 8.19 (2H, d), 8.08 (1H, t), 7.91 ~ 7.94 (4H, m), 7.75 ~ 7.83 (4H, m), 7.25 ~ 7.62 (22H, m), 7.03 (1H, t), 6.83 (1H, dd), 6.69 (4H, d), 1.72 (6H, s) 855.07 854.37 370 8.55 (1H, dd), 8.18-8.30 (4H, m), 8.08 (1H, s), 7.91-7.94 (5H, m), 7.75-7.79 (2H, m), 7.22-7.82 (16H, m), 7.03 (1H, s), 6.83 (1H, dd), 6.69 (3H, d), 6.62 (1H, dd) 686.84 686.27 375 8.55 (1H, dd), 8.18 ~ 8.19 (3H, m), 8.08 (1H, s), 7.91 ~ 7.94 (4H, m), 7.75 ~ 7.81 (5H, m), 7.19 ~ 7.62 (17H, m), 7.03 (1H, s), 6.80 ~ 6.83 (2H, m), 6.69 (2H, d) 712.88 712.29 380 8.93 (1H, dd), 8.55 (1H, dd), 8.12 ~ 8.18 (3H, m), 7.79 ~ 7.94 (6H, m), 7.71 (2H, s), 7.25 ~ 7.62 (14H, m), 7.02 ~ 7.04
(2H, d), 6.69 (2H, d), 6.48 (1H, dd), 1.72 (6H, s) 702.88 702.30 385 8.93 (1H, dd), 8.55 (1H, dd), 8.12 ~ 8.18 (3H, m), 7.79 ~ 7.94 (5H, m), 7.71 (2H, s), 7.50 ~ 7.62 (8H, m), 7.19 ~ 7.33 (7H, m), 7.02-7.06 (2H, m), 6.69 (2H, d), 6.51 (1H, s), 6.39 (1H, dd), 3.91 (2H, s), 1.72 (6H, s) 716.91 716.32 390 8.93 (3H, d), 8.55 (1H, dd), 8.33 (1H, d), 8.18 (1H, d), 8.13 (1H, s), 8.12 (3H, d), 7.94 (1H, d), 7.88 ~ 7.79 (8H, m), 7.71 (2H, s), 7.62-7.45 (8H, m), 7.33-7.25 (2H, m), 7.02 (1H, d), 6.91 (1H, s), 6.69 (2H , d), 686.84 686.27 395 8.93 (3H, dd), 8.55 (1H, dd), 8.12 ~ 8.18 (5H, m), 7.79 ~ 7.94 (9H, m), 7.71 (2H, s), 7.45 ~ 7.62 (8H, m), 7.25 ~ 7.36 (4H, m), 7.02 (1H, dd), 6.69 (2H, d), 6.44 (1H, dd), 1.85 (6H, s) 803.00 802.33 400 8.55 (2H, dd), 8.45 (1H, d), 8.18 (1H, d), 8.08-8.0 (4H, m), 7.79 (1H, d), 7.82-7.79 (2H, dd), 7.71 (4H, s), 7.62-7.5 (13H, m), 7.33-7.25 (2H, m), 7.20 (2H, s), 6.69 (4H, d) 736.90 736.29 405 8.55 (1H, dd), 8.18 (1H, d), 7.25-8.00 (26H, m), 7.07 (1H, t), 6.69 (2H, d), 6.39 (1H, dd) 700.82 700.25 410 8.55 (1H, dd), 8.18 (1H, d), 7.93-8.00 (4H, m), 7.71-7.83 (8H, m), 7.20-7.63 (22H, m), 6.69 (4H, d), 1.72 ( 6H, s) 879.10 878.37 415 8.55 (1H, dd), 8.30 (1H, s), 8.25 (1H, s), 8.18 (1H, d), 8.0 (2H, d), 7.94-7.81 (4H, m), 7.79 (1H, dd) , 7.71 (4H, s), 7.62 ~ 7.22 (14H, m), 7.20 (2H, s), 6.69 (2H, d), 6.62 (1H, d) 710.86 710.27 420 8.55 (1H, dd), 8.18-8.19 (2H, m), 7.92-8.00 (5H, m), 7.71-7.82 (10H, m), 7.62 (1H, s), 7.20-7.54 (13H, m), 7.00 (1H, d), 6.80 (1H, s), 6.69 (2H, d), 6.23-6.31 (2H, m), 3.66 (2H, d) 825.01 824.32 425 8.55 (2H, m), 8.42-8.45 (2H, m), 8.18 (1H, d), 7.92-8.08 (5H, m), 7.77-7.81 (3H, m), 7.25-7.82 (15H, m), 7.00 (1H, d), 6.86 (1H, d), 6.69 (4H, d), 6.23-6.31 (2H, m), 3.66 (2H, d) 807.01 806.28 430 8.55 (2H, m), 8.42 (1H, d), 8.33 (1H, d), 8.18 (1H, d), 8.08-8.04 (2H, m), 7.94-7.72 (3H, m), 7.79-7.77 ( 5H, m), 7.62-7.19 (17H, m), 7.0 (1H, dd), 6.80 (1H, s), 6.69 (4H, d), 6.31-6.23 (2H, m), 3.66 (2H, d) , 827.02 826.33 435 8.55 (2H, m), 8.42 (1H, dd), 8.18 (1H, d), 8.04-8.08 (2H, m), 7.92-7.74 (2H, m), 7.77-7.79 (2H, m), 7.25- 7.62 (18H, m), 7.00 (1H, d), 6.88-6.89 (2H, d), 6.69 (4H, d), 6.59 (1H, dd), 6.23-6.31 (2H, m), 3.66 (2H, d) 776.96 776.32 440 8.55 (2H, m), 8.42 (1H, dd), 8.18 (1H, d), 7.92-8.08 (7H, m), 7.73-7.79 (3H, m), 7.25-7.82 (16H, m), 7.00 ( 1H, dd), 6.88-6.89 (2H, dd), 6.69 (4H, d), 6.59 (1H, dd), 6.23-6.31 (2H, m), 3.66 (2H, d) 827.02 826.33 445 8.55 (1H, dd), 8.45 (1H, m), 8.18 (1H, d), 7.98-7.92 (3H, m), 7.84-7.74 (6H, m), 7.62 (1H, s), 7.54-7.25 ( 17H, m), 7.0 (1H, dd), 6.86 (1H, dd), 6.69 (2H, d), 6.31-6.23 (2H, m), 3.66 (2H, d) 807.01 806.28 450 8.55 (1H, dd), 8.33 (1H, dd), 8.18 (1H, d), 7.92-7.74 (3H, m), 7.74-7.84 (8H, m), 7.62 (1H, s), 7.19-7.54 ( 19H, m), 7.00 (1H, dd), 6.80 (1H, s), 6.69 (2H, d), 6.23-6.31 (2H, m), 3.66 (2H, d) 827.02 826.33 455 8.55 (1H, dd), 8.18 (1H, d), 7.94 (1H, d), 7.80 ~ 7.68 (8H, m), 7.62 (1H, s), 7.54 ~ 7.25 (23H, m), 6.89 (1H, s), 6.88 (1H, d), 6.69 (4H, d), 6.59 (1H, dd) 764.95 764.32 460 8.55 (1H, dd), 8.18 (1H, d), 7.92-8.00 (4H, m), 7.25-7.84 (31H, m), 6.88-6.89 (2H, dd), 6.69 (2H, d), 6.59 ( 1H, dd) 815.01 814.33 465 8.55 (1H, dd), 8.18 (1H, d), 7.87 ~ 7.94 (3H, m), 7.79 (3H, dd), 7.62 ~ 7.68 (4H, m), 7.25 ~ 7.54 (16H, m), 7.04 ~ 7.07 (2H, m), 6.69 (2H, d), 6.48 (1H, dd), 6.39 (1H, dd) 768.94 768.31 470 8.55 (1H, dd), 8.18 (1H, d), 7.77 ~ 7.94 (8H, m), 7.62 ~ 7.68 (4H, m), 7.25 ~ 7.55 (22H, m), 7.04 (1H, s), 6.69 ( 4H, d), 6.48 (1H, dd), 1.72 (12H, s) 947.21 946.23 475 8.55 (1H, dd), 8.30 (1H, s), 8.25 (1H, t), 8.18 (1H, d), 7.87 ~ 7.94 (4H, m), 7.79 (3H, d), 7.62 ~ 7.68 (3H, m), 7.22 to 7.55 (17H, m), 7.04 (1H, s), 6.69 (2H, d), 6.62 (1H, dd), 6.48 (1H, dd), 1.72 (6H, s) 778.98 778.33 480 8.55 (1H, dd), 8.19-8.18 (2H, m), 7.94-7.79 (9H, m), 7.68 (2H, d), 7.62 (1H, s), 7.55-7.19 (18H, m), 7.04 ( 1H, s), 6.80 (1H, s), 6.69 (2H, s), 6.48 (1H, d), 1.72 (6H, s) 805.02 804.35 485 8.55 (2H, dd), 8.45 (1H, m), 8.18 (1H, d), 7.79-7.81 (4H, m), 7.25-7.68 (23H, m), 6.86 (1H, dd), 6.77 (1H, d), 6.75 (1 H, s), 6.69 (2 H, d) 834.04 833.29 490 8.55 (1H, dd), 8.45 (1H, m), 8.3 (1H, s), 8.18 (1H, d), 7.9-8.07 (8H, m), 7.79-7.81 (2H, td), 7.50-7.82 ( 8H, m), 7.25-7.4 (8H, m), 6.98 (1H, dd), 6.86 (1H, dd), 6.69 (2H, d) 742.93 742.24 495 8.55 (1H, dd), 8.45 (1H, m), 8.28-8.3 (2H, dd), 8.18 (1H, d), 7.9-8.01 (8H, m), 7.79-7.81 (2H, td), 7.19- 7.62 (17H, m), 6.86 (1H, dd), 6.69 (2H, d), 6.44 (1H, dd), 1.78 (6H, s) 859.09 858.31 500 8.55 (1H, dd), 8.3 (1H, s), 8.18 (1H, d), 7.94-7.89 (6H, m), 7.79 (1H, d), 7.66 (1H, d), 7.62 (1H, s) , 7.54 (2H, d), 7.4 ~ 7.19 (13H, m), 7.07 (1H, d), 7.06 (1H, d), 6.69 (2H, d), 6.51 (1H, s), 6.39 (1H, d ), 3.91 (2H, s), 1.72 (6H, s) 806.99 806.33 505 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (1H, s), 8.18 (1H, d),
8.12 (2H, dd), 7.82-7.74 (11H, m), 7.62-7.72 (2H, m), 7.54 (2H, m), 7.25-7.4 (9H, m), 7.07 (1H, t), 6.91 ( 1H, s), 6.69 (2H, d), 6.39 (1H, dd) 776.92 776.28 510 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (1H, s), 8.18 (1H, d),
8.12 (2H, dd), 7.79 ~ 7.94 (11H, m), 7.62 ~ 7.66 (2H, m), 7.54 (2H, d), 7.5 ~ 7.4 (11H, m), 7.07 (1H, t), 6.69 ( 2H, d), 6.39-6.44 (2H, qd), 1.85 (6H, s) 893.08 892.35 515 8.55 (2H, dd), 8.3 (1H, s), 8.18 (1H, d), 7.94-7.9 (6H, m), 7.79 (1H, d), 7.62-7.19 (21H, m), 7.06 (1H, d), 6.77 (1H, d), 6.75 (1H, d), 6.69 (2H, d), 6.51 (1H, s), 6.39 (1H, d), 3.91 (2H, s), 1.72 (6H, s ) 882.10 881.38 520 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 8.02 ~ 8.07 (2H, m), 7.9 ~ 7.94 (5H, m), 7.79 (1H, dd), 7.53 ~ 7.62 ( 6H, m), 7.19-7.4 (10H, m), 7.06 (1H, d), 6.98 (1H, dd), 6.69 (2H, d), 6.51 (1H, s), 6.39 (1H, dd) 766.97 766.33 525 8.55 (1H, dd), 8.3 (2H, s), 8.28 (1H, s), 8.18 (1H, d), 8.01-7.9 (7H, m), 7.79 (1H, d), 7.62 (1H, s) , 7.58-7.52 (5H, m), 7.45 (1H, d), 7.4-7.19 (10H, m), 7.06 (1H, d), 6.69 (2H, d), 6.51 (1H, s), 7.44-7.39 (2H, qd), 3.91 (2H, s), 1.78 (6H, s), 1.72 (6H, s) 883.13 882.40 530 8.55 (1H, dd), 8.33 (2H, s), 8.18 (1H, d),
8.12 (2H, dd), 7.77-7.74 (9H, m), 7.25-7.69 (28H, m), 6.69 (4H, d), 5.93 (1H, dd), 1.72 (6H, s) 1020.26 1019.42 535 8.55 (1H, dd), 8.3 (2H, s), 8.30-8.25 (2H, s), 7.79 (1H, d), 7.69 (1H, d), 7.63-7.72 (21H, m), 6.69 (2H, d), 6.62 (1 H, d), 5.93 (1 H, d) 852.03 851.33 540 8.55 (1H, dd), 8.3 (2H, s), 8.12-8.19 (3H, m), 7.9-7.94 (6H, m), 7.79-7.81 (4H, m), 7.19-7.63 (23H, m), 6.80 (1H, s), 6.69 (2H, d), 5.93 (1H, dd) 878.07 877.35 545 8.55 (1H, dd), 8.3 (2H, s), 8.30-8.25 (2H, dd), 8.18 (1H, d), 8.12-8.08 (4H, m), 7.94-7.9 (7H, m), 7.79 ( 1H, d), 7.69 (1H, d), 7.64-7.5 (10H, m), 7.4-7.25 (10H, m), 6.69 (2H, d), 6.62 (1H, d), 5.93 (1H, d) 902.09 901.35 550 8.55 (1H, dd), 8.3 (2H, s), 8.08 ~ 8.19 (6H, m), 7.9 ~ 7.94 (6H, m), 7.79 ~ 7.81 (4H, m), 7.19 ~ 7.69 (22H, m), 6.80 (1H, s), 6.69 (2H, d), 5.93 (1H, dd) 928.13 927.36 555 8.93 (2H, dd), 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 8.12 (3H, d), 7.94-7.79 (13H, m), 7.71 (4H, s) , 7.62 (1H, s), 7.54 (2H, d), 7.4 ~ 7.25 (5H, m), 7.01 (1H, d), 6.91 (1H, s), 6.69 (2H, d) 810.98 810.30 560 8.55 (1H, dd), 8.3 (2H, s), 8.18 (1H, d), 8.12 (2H, dd)
, 7.71 ~ 7.94 (20H, m), 7.62 (1H, s), 7.54 (2H, d), 7.25 ~ 7.4 (5H, m), 7.02 (2H, s), 6.69 (2H, d) 835.00 834.30

Manufacturing example  1 to 101, Comparative Manufacturing Example  1: using the compound of the present invention The organic electroluminescent device  Produce

First, the transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning Co., Ltd.) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water in sequence, and then stored in isopropanol and used.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition equipment, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA).

Subsequently, after evacuating the chamber until the vacuum reached 10 ⁻⁶ torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 200 Å thick hole injection layer on the ITO substrate. The compound shown in Table 3 below was placed in another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to the cell to deposit a 600 Å thick hole transport layer on the hole injection layer.

After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. In one cell of the vacuum deposition equipment, tris (8-hydroxyquinoline) aluminum (III): Alq was added as a luminescent material as a host, and in the other cell, C545T was used as a dopant. Put in.

Subsequently, the two cells were heated together, and the light emitting layer was deposited to a thickness of 400 kPa on the hole transport layer by depositing the deposition rate ratio of the dopant at 5 wt% (host: dopant = 95: 5). Subsequently, tris (8-hydroxyquinoline) aluminum (III): Alq was deposited to a thickness of 200 kV as an electron transport layer.

Thereafter, the following compound lithium fluoride (LiF) was deposited as an electron injecting layer to a thickness of 10 Å. And an Al cathode was deposited to a thickness of 1000 Å to produce an OLED.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

Hole transport layer material Production Example 1 Synthesis Example 1 Production Example 2 Synthesis Example 2 Production Example 3 Synthesis Example 3 Production Example 4 Synthesis Example 4 Production Example 5 Synthesis Example 5 Production Example 6 Synthesis Example 6 Production Example 7 Synthesis Example 7 Production Example 8 Synthesis Example 8 Production Example 9 Synthesis Example 9 Production Example 10 Synthesis Example 10 Production Example 11 Synthesis Example 11 Production Example 12 Synthesis Example 12 Production Example 13 Synthesis Example 13 Production Example 14 Synthesis Example 14 Production Example 15 Synthesis Example 15 Production Example 16 Synthesis Example 16 Production Example 17 Synthesis Example 17 Production Example 18 Synthesis Example 18 Production Example 19 Synthesis Example 19 Production example 20 Synthesis Example 20 Production Example 21 Synthesis Example 21 Production Example 22 Synthesis Example 22 Production Example 23 Synthesis Example 23 Production Example 24 Synthesis Example 24 Production example 25 Synthesis Example 25 Production Example 26 Synthesis Example 26 Production Example 27 Synthesis Example 27 Production Example 28 Synthesis Example 28 Production Example 29 Synthesis Example 29 Production Example 30 Synthesis Example 30 Production Example 31 Synthesis Example 31 Production example 32 Synthesis Example 32 Production Example 33 Synthesis Example 33 Production example 34 Synthesis Example 34 Production example 35 Synthesis Example 35 Production Example 36 Synthesis Example 36 Production example 37 Synthesis Example 37 Production Example 38 Synthesis Example 38 Production example 39 Synthesis Example 39 Production example 40 Synthesis Example 40 Production example 41 Synthesis Example 41 Production example 42 Synthesis Example 42 Production Example 43 Synthesis Example 43 Production example 44 Synthesis Example 44 Production example 45 Synthesis Example 45 Production example 46 Synthesis Example 46 Production example 47 Synthesis Example 47 Production Example 48 Synthesis Example 48 Production Example 49 Synthesis Example 49 Production Example 50 Synthesis Example 50 Production example 51 Synthesis Example 51 Production example 52 Synthesis Example 52 Production Example 53 Synthesis Example 53 Production example 54 Synthesis Example 54 Production example 55 Synthesis Example 55 Production example 56 Synthesis Example 56 Production Example 57 Synthesis Example 57 Production Example 58 Synthesis Example 58 Production example 59 Synthesis Example 59 Production example 60 Synthesis Example 60 Production example 61 Synthesis Example 61 Production example 62 Synthesis Example 62 Production Example 63 Synthesis Example 63 Production example 64 Synthesis Example 64 Production example 65 Synthesis Example 65 Production example 66 Synthesis Example 66 Production example 67 Synthesis Example 67 Production example 68 Synthesis Example 68 Production Example 69 Synthesis Example 69 Production example 70 Synthesis Example 70 Preparation Example 71 Synthesis Example 71 Preparation Example 72 Synthesis Example 72 Preparation Example 73 Synthesis Example 73 Production example 74 Synthesis Example 74 Preparation 75 Synthesis Example 75 Production Example 76 Synthesis Example 76 Production Example 77 Synthesis Example 77 Production Example 78 Synthesis Example 78 Production Example 79 Synthesis Example 79 Production example 80 Synthesis Example 80 Production example 81 Synthesis Example 81 Production example 82 Synthesis Example 82 Production Example 83 Synthesis Example 83 Production Example 84 Synthesis Example 84 Production Example 85 Synthesis Example 85 Production example 86 Synthesis Example 86 Production Example 87 Synthesis Example 87 Production example 88 Synthesis Example 88 Production example 89 Synthesis Example 89 Production Example 90 Synthesis Example 90 Production example 91 Synthesis Example 91 Production Example 92 Synthesis Example 92 Production example 93 Synthesis Example 93 Preparation 94 Synthesis Example 94 Preparation Example 95 Synthesis Example 95 Preparation Example 96 Synthesis Example 96 Production example 97 Synthesis Example 97 Preparation Example 98 Synthesis Example 98 Preparation Example 99 Synthesis Example 99 Preparation Example 100 Synthesis Example 100 Preparation Example 101 Synthesis Example 101 Production Example 102 Synthesis Example 102 Production example 103 Synthesis Example 103 Production example 104 Synthesis Example 104 Production example 105 Synthesis Example 105 Preparation Example 106 Synthesis Example 106 Preparation Example 107 Synthesis Example 107 Preparation Example 108 Synthesis Example 108 Preparation Example 109 Synthesis Example 109 Preparation Example 110 Synthesis Example 110 Preparation Example 111 Synthesis Example 111 Preparation Example 112 Synthesis Example 112 Preparation Example 113 Synthesis Example 113 Comparative Preparation Example 1

N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4 '-diamine: NPB)

Test Example  One: OLED Characterization of

The power efficiency and driving life of the OLED devices of Preparation Examples 1 to 113 and Comparative Production Example 1 are shown in Table 4 below at 1,000 cd / m ² and the time until the efficiency drops to 50%.

Cd / A @ 1000 cd / m ² Life (T ₅₀ ) Production Example 1 13.2 710 Production Example 2 13.1 680 Production Example 3 13.3 750 Production Example 4 13.2 730 Production Example 5 13.0 710 Production Example 6 13.2 750 Production Example 7 13.0 690 Production Example 8 13.4 740 Production Example 9 14.8 410 Production Example 10 13.2 690 Production Example 11 13.3 700 Production Example 12 13.2 710 Production Example 13 13.3 750 Production Example 14 15.0 430 Production Example 15 13.3 680 Production Example 16 13.2 710 Production Example 17 14.9 420 Production Example 18 13.2 690 Production Example 19 13.3 710 Production example 20 12.1 400 Production Example 21 12.5 550 Production Example 22 12.3 500 Production Example 23 12.8 480 Production Example 24 12.7 490 Production example 25 12.3 530 Production Example 26 14.1 390 Production Example 27 12.6 500 Production Example 28 12.5 530 Production Example 29 13.4 700 Production Example 30 13.4 720 Production Example 31 13.2 700 Production example 32 12.9 580 Production Example 33 13.4 710 Production example 34 13.3 720 Production example 35 12.9 650 Production Example 36 12.8 600 Production example 37 13.1 750 Production Example 38 15.0 410 Production example 39 13.2 700 Production example 40 12.9 710 Production example 41 13.4 420 Production example 42 13.2 680 Production Example 43 12.9 650 Production example 44 13.5 690 Production example 45 13.4 430 Production example 46 13.3 410 Production example 47 13.4 450 Production Example 48 12.8 420 Production Example 49 12.6 390 Production Example 50 12.9 410 Production example 51 12.6 540 Production example 52 12.7 560 Production Example 53 12.7 550 Production example 54 12.6 580 Production example 55 12.9 570 Production example 56 13.0 610 Production Example 57 13.1 590 Production Example 58 13.2 680 Production example 59 13.5 710 Production example 60 13.4 760 Production example 61 13.3 690 Production example 62 13.2 590 Production Example 63 13.4 680 Production example 64 13.4 690 Production example 65 13.7 480 Production example 66 13.3 750 Production example 67 13.3 670 Production example 68 13.4 610 Production Example 69 13.3 650 Production example 70 13.8 450 Preparation Example 71 13.2 710 Preparation Example 72 13.5 650 Preparation Example 73 13.9 410 Production example 74 13.3 690 Preparation 75 13.2 590 Production Example 76 13.4 610 Production Example 77 12.9 510 Production Example 78 13.5 410 Production Example 79 13.0 590 Production example 80 13.0 620 Production example 81 13.1 520 Production example 82 13.6 390 Production Example 83 13.5 610 Production Example 84 12.4 450 Production Example 85 12.9 510 Production example 86 13.0 590 Production Example 87 12.9 530 Production example 88 13.1 550 Production example 89 13.0 620 Production Example 90 13.5 650 Production example 91 13.2 590 Production Example 92 13.4 600 Production example 93 13.3 670 Preparation 94 13.8 420 Preparation Example 95 13.5 680 Preparation Example 96 13.3 590 Production example 97 13.3 630 Preparation Example 98 13.3 610 Preparation Example 99 13.3 510 Preparation Example 100 13.4 580 Preparation Example 101 14.0 380 Production Example 102 13.5 470 Production example 103 13.4 500 Production example 104 14.8 450 Production example 105 14.5 480 Preparation Example 106 14.5 490 Preparation Example 107 13.4 620 Preparation Example 108 13.3 530 Preparation Example 109 13.3 580 Preparation Example 110 13.0 510 Preparation Example 111 13.3 590 Preparation Example 112 13.3 530 Preparation Example 113 12.9 490 Comparative Preparation Example 1 11.4 350

As shown in Table 3, when the compound according to the present invention is used as a hole transport layer material, it can be seen that the power efficiency and lifespan of the organic light emitting display device are excellent.

Claims (8)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
R ₁ , R ₂ and R ₃ may be the same as or different from each other, and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; A substituted or unsubstituted (C1-C60) alkyl group; A substituted or unsubstituted (C6-C60) aryl group; A substituted or unsubstituted (C5-C60) heteroaryl group; 5- or 6-membered heterocycloalkyl groups containing one or two or more selected from N, O, S and Si; Substituted or unsubstituted (C3-C60) cycloalkyl; Substituted or unsubstituted tri (C1-C60) alkylsilyl group; A substituted or unsubstituted di (C1-C60) alkyl (C6-C60) arylsilyl group; A substituted or unsubstituted tri (C6-C60) arylsilyl group; A substituted or unsubstituted (C7-C60) bicycloalkyl group; Substituted or unsubstituted (C2-C60) alkenyl group; Substituted or unsubstituted (C2-C60) alkynyl group; A substituted or unsubstituted (C1-C60) alkoxy group; A substituted or unsubstituted (C1-C60) alkylamino group; A substituted or unsubstituted (C6-C60) arylamino group; A substituted or unsubstituted (C6-C60) ar (C1-C60) alkyl group; Substituted or unsubstituted (C6-C60) aryloxy group; Substituted or unsubstituted (C6-C60) arylthio group; Substituted or unsubstituted (C1-C60) Alkylthio group; Substituted or unsubstituted (C1-C60) alkoxycarbonyl group; A substituted or unsubstituted (C1-C60) alkylcarbonyl group; Or a (C6-C60) arylcarbonyl group,
R ₁ , R _2, and R ₃ may be linked to a substituted or unsubstituted (C2-C60) alkylene or (C2-C60) alkenylene containing or not containing a fused ring with an adjacent element to form an alicyclic ring, a monocyclic ring, or Polycyclic aromatic rings can be formed. The method according to claim 1,
R ₁ , R ₂ and R ₃ may be the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted (C1-C60) alkyl group, a substituted or unsubstituted (C1-C60) aryl group, a substituted or Unsubstituted (C5-C60) heteroaryl group, substituted or unsubstituted (C1-C60) alkylamino, substituted or unsubstituted (C6-C60) arylamino,

,

,

,

,

,

,

or

ego,
X ₄ to X ₁₂ may be the same as or different from each other, and each independently C, N, O, unsubstituted or substituted with (C1-C10) alkyl, (C1-C10) aryl or (C1-C10) aralkyl S or Si,
R ₄ to R ₇ may be the same as or different from each other, and each independently hydrogen, a (C1-C60) alkyl group, a (C1-C60) alkoxy group or a (C6-C60) aryl group,
R ₄ to R ₇ are each independently connected to an adjacent element to form an alicyclic ring, a monocyclic or polycyclic aromatic ring, characterized in that. The method according to claim 1,
The (C1-C60) alkyl group, (C1-C60) aryl group, (C5-C60) heteroaryl group or (C6-C60) arylamino is CF ₃ , halogen atom, cyano, (C1-C60) alkyl group, ( C1-C60) alkoxy group, (C6-C60) aryl group or

Substituted with
X ₁₃ is C, N, O, S or Si unsubstituted or substituted with (C1-C10) alkyl, (C1-C10) aryl or (C1-C10) aralkyl. The method according to claim 2,
The R ₁ , R ₂ and R ₃ may be the same as or different from each other, each independently characterized in that one of the following substituents:

A first electrode; A second electrode; And an organic film disposed between the first electrode and the second electrode, the organic film comprising the compound of claim 1. The method of claim 5,
The organic film includes an emission layer and a hole transport layer comprising the compound. The method of claim 5,
The organic layer is an organic light emitting display device further comprises one or two or more selected from the group consisting of a hole injection layer, an electron transport layer and an electron injection layer. An organic solar cell comprising the compound of claim 1.