KR102303425B1 - Benzimidazolone derivatives organic light emitting compound and organic electroluminescent device including the same - Google Patents

Abstract

상기 벤조 이미다졸론 유도체 유기발광 화합물은 유기 전계발광 소자에 포함시 적절한 에너지 준위, 전기 화학적 안정성 및 열적 안정성등을 모두 우수하게 만족시킬 수 있다.A benzoimidazolone derivative organic light emitting compound represented by the following formula (a) is provided.
[Formula a]

When the benzoimidazolone derivative organic light emitting compound is included in an organic electroluminescent device, it is possible to excellently satisfy all of the appropriate energy level, electrochemical stability and thermal stability.

Description

Benzimidazolone derivatives organic light emitting compound and organic electroluminescent device including the same

It relates to a benzoimidazolone derivative organic light emitting compound and an organic electroluminescent device comprising the same.

BACKGROUND ART An electroluminescence device (EL device) is a self-emission type display device, and has advantages of a fast response speed and a wide viewing angle. In 1987, Eastman Kodak (Eastman Kodak) first developed an organic EL device using a low molecular weight aromatic diamine and aluminum complex as a light emitting layer material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency of an organic EL device is a luminescent material. Among luminescent materials, a phosphorescent material can theoretically improve luminous efficiency by 4 times compared to a fluorescent material. So far, iridium (III) complex-based and carbazole-based materials are widely known as phosphorescent materials, and new phosphorescent materials are being studied recently.

The principle of the organic electroluminescence phenomenon is that when a voltage is applied between the two electrodes when there is an organic thin film layer between the cathode and the anode, electrons and holes are respectively injected into the organic thin film layer from the cathode and the anode. Electrons and holes injected into the organic thin film layer recombine to form excitons, and the excitons fall back to the ground state and emit light. An organic electroluminescent device using this principle may be generally composed of a cathode and an anode and an organic thin film layer positioned therebetween, for example, an organic thin film layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

Materials used in organic electroluminescent devices are mostly pure organic substances or complex compounds formed by complexing organic substances with metals, and can be used as hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. depending on the use. can be distinguished. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable. desirable. Therefore, there is a demand in the art for the development of a new organic material satisfying the above requirements.

One embodiment of the present invention provides a benzoimidazolone derivative organic light emitting compound having an appropriate energy level, electrochemical stability and thermal stability, and an organic electroluminescent device including the same.

In one embodiment of the present invention, there is provided a benzoimidazolone derivative organic light emitting compound represented by the following formula (a).

<Formula a>

In the above formula,

R ₁ is C1~ C30 alkyl group, C2~ C30 alkenyl group, C2~ C30 alkynyl group, substituted or unsubstituted C5~ C30 arylene, substituted or unsubstituted C3~ C30 N, O, S It is one selected from the group consisting of a heteroaryl group, including a C5~ C40 aryloxy group, a C6~ C40 arylalkyl group, a C3~ C40 cycloalkyl group, and combinations thereof,

When R ₁ is substituted, the substituent is hydrogen, deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group , is selected from the group consisting of a C5~ C40 heteroaryl group,

R ₂ is a substituted or unsubstituted C5~ C30 arylene, a substituted or unsubstituted C4~ C30 heteroaryl group including N, a C6~ C40 arylalkyl group, a C3~ C40 cycloalkyl group, and combinations thereof is one selected from the group consisting of,

When R ₂ is substituted, the substituent is selected from the group consisting of hydrogen, halogen, cyano group, and a C1-C40 alkyl group,

L is a substituted or unsubstituted C5~ C30 aryl group, a substituted or unsubstituted C10~ C30 condensed aryl group, a substituted or unsubstituted C5~ C30 heteroaryl group including N, O, S, and their one selected from the group consisting of combinations; When L is substituted, the substituents are hydrogen, deuterium, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group, C5~ C40 heteroaryl group, and It is selected from the group consisting of combinations thereof,

Z is N or C-R, and a plurality of Z are, each independently, the same or different from each other,

Wherein R is the same as the definition of _{Ar 1 below,}

Ar ₁ is a substituted or unsubstituted C6~ C60 aryl group, a substituted or unsubstituted C5~ C60 heteroaryl group including N, O, S, C6~ C60 aryloxy group, C1~ C60 alkylox a group or a C6~ C60 arylalkyl group, a C3~C60 cycloalkyl group; When a plurality of Ar ₁ are present, they are each independently the same as or different from each other,

When Ar ₁ is substituted, the substituent is hydrogen, deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group , is selected from the group consisting of a C5~ C40 heteroaryl group,

m is an integer of 1 to 2,

n is an integer from 1 to 4.

Specifically, R ₁ may be any one compound selected from the group consisting of the following structural formula.

Specifically, R ₂ may be any one compound selected from the group consisting of the following structural formula.

Specifically, the L may be any one compound selected from the group consisting of the following structural formula.

Specifically, Ar ₁ may be any one compound selected from the group consisting of the following structural formula.

The organic light emitting compound may be used as a material for an emission layer, a hole blocking layer, an electron transport layer, or an electron injection layer among materials for an organic light emitting device.

In another embodiment of the present invention, in the organic electroluminescent device in which at least one organic thin film layer is sandwiched between the cathode and the anode, the organic thin film layer has a multilayer structure including at least one light emitting layer and an electron transport region, and the organic At least one layer in the thin film layer provides an organic electroluminescent device comprising the benzoimidazolone derivative organic light emitting compound alone or a mixture of two or more.

One or more layers selected from the layers formed between the cathode and the anode provide an organic electroluminescent device, characterized in that formed by a vacuum deposition process or a solution process.

The organic electroluminescent device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; devices for flexible lighting of monochromatic or white color; It provides an organic electroluminescent device comprising that used in any one device selected from the group consisting of.

The benzoimidazolone derivative organic light emitting compound can excellently satisfy all of the conditions required for materials usable in an organic electroluminescent device, such as an appropriate energy level, electrochemical stability and thermal stability, and depending on the substituent, organic electroluminescence. It can play various roles required in the device.

1 is a lifespan characteristic evaluation graph showing the measurement results of the organic electroluminescent devices prepared in Examples 1 to 8 and Comparative Examples 1 to 2;
2 is a lifespan characteristic evaluation graph showing measurement results for the organic electroluminescent devices prepared in Examples 9 to 12 and Comparative Examples 1 and 3;

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

In the present specification, "substituted" means, unless otherwise defined, a C1-C12 alkyl group, an amino group, a nitrile group, a C3-C7 cycloalkyl group, a C2-C12 alkenyl group, a C3-C7 cycloalkenyl group, C2 -C50 alkynyl group, C5-C50 cycloalkynyl group, cyano group, C1-C12 alkoxy group, C6-C60 aryl group, and C7-C60 arylalkyl group substituted with a substituent selected from the group consisting of and combinations thereof including cases where

In the present specification, "a combination of these" means that, unless otherwise defined, two or more substituents are bonded to a linking group, or two or more substituents are condensed and bonded.

As used herein, unless otherwise defined, "hetero" means including a hetero atom in one compound or a substituent, and the hetero atom is one selected from the group consisting of N, O, S, P, and combinations thereof. can be For example, it may mean a case in which 1 to 3 hetero atoms are included in the one compound or substituent, and the remainder is carbon.

In one embodiment of the present invention, there is provided a novel benzoimidazolone derivative compound represented by the following formula (a).

<Formula a>

In the above formula,

R ₁ is C1~ C30 alkyl group, C2~ C30 alkenyl group, C2~ C30 alkynyl group, substituted or unsubstituted C5~ C30 arylene, substituted or unsubstituted C3~ C30 N, O, S It is one selected from the group consisting of a heteroaryl group, including a C5~ C40 aryloxy group, a C6~ C40 arylalkyl group, a C3~ C40 cycloalkyl group, and combinations thereof,

When R ₁ is substituted, the substituent is hydrogen, deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group , is selected from the group consisting of a C5~ C40 heteroaryl group,

R ₂ is a substituted or unsubstituted C5~ C30 arylene, a substituted or unsubstituted C4~ C30 heteroaryl group including N, a C6~ C40 arylalkyl group, a C3~ C40 cycloalkyl group, and combinations thereof is one selected from the group consisting of,

When R ₂ is substituted, the substituent is selected from the group consisting of hydrogen, halogen, cyano group, and a C1-C40 alkyl group,

L is a substituted or unsubstituted C5~ C30 aryl group, a substituted or unsubstituted C10~ C30 condensed aryl group, a substituted or unsubstituted C5~ C30 heteroaryl group including N, O, S, and their one selected from the group consisting of combinations; When L is substituted, the substituents are hydrogen, deuterium, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group, C5~ C40 heteroaryl group, and It is selected from the group consisting of combinations thereof,

Z is N or C-R, and a plurality of Z are, each independently, the same or different from each other,

Wherein R is the same as the definition of _{Ar 1 below,}

Ar ₁ is a substituted or unsubstituted C6~ C60 aryl group, a substituted or unsubstituted C5~ C60 heteroaryl group including N, O, S, C6~ C60 aryloxy group, C1~ C60 alkylox a group or a C6~ C60 arylalkyl group, a C3~C60 cycloalkyl group; When a plurality of Ar ₁ are present, they are each independently the same as or different from each other,

When Ar ₁ is substituted, the substituent is hydrogen, deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C5~ C40 aryloxy group, C1~ C40 alkyloxy group, C6~ C40 aryl group , is selected from the group consisting of a C5~ C40 heteroaryl group,

m is an integer of 1 to 2,

n is an integer from 1 to 4.

Specifically, Formula R ₁ may be any one compound selected from the group consisting of the following structural formula.

Specifically, R ₂ may be any one compound selected from the group consisting of the following structural formula.

Specifically, the L may be any one compound selected from the group consisting of the following structural formula.

Specifically, Ar ₁ may be any one compound selected from the group consisting of the following structural formula.

For example, the benzoimidazolone derivative organic light emitting compound may be any one of compounds 1 to 345 described in Table 1 below.

[Table 1]

The organic light emitting compound may be used as a material for an emission layer, a hole blocking layer, an electron transport layer, or an electron injection layer among materials for an organic light emitting device.

In another embodiment of the present invention, in the organic electroluminescent device in which at least one organic thin film layer is sandwiched between the cathode and the anode, the organic thin film layer comprises a benzoimidazolone derivative organic light emitting compound alone or in two or more types.

More specifically, the organic thin film layer has a multilayer structure including at least one light emitting layer and an electron transport region, and at least one of the light emitting layer and the electron transport region in the organic thin film layer contains the benzoimidazolone derivative organic compound alone or two An organic electroluminescent device comprising a mixture of more than one species is provided.

At least one layer selected from the organic thin film layer formed between the cathode and the anode provides an organic electroluminescent device, characterized in that formed by a vacuum deposition process or a solution process.

The organic electroluminescent device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; devices for flexible lighting of monochromatic or white color; It provides an organic electroluminescent device comprising that used in any one device selected from the group consisting of.

A detailed description of the benzoimidazolone derivative organic light emitting compound represented by Formula (a) included in the organic thin film layer is the same as described above.

Hereinafter, Examples and Comparative Examples of the present invention will be described. The following examples are only examples of the present invention, and the present invention is not limited to the following examples.

(Example)

Hereinafter, reaction examples and comparative examples are specifically exemplified, but the present invention is not limited to the following reaction examples and examples. In the following reaction examples, the intermediate compound is indicated by adding a serial number to the number of the final product. For example, compound 1 is denoted as compound [1], and an intermediate compound of the compound is denoted as [1-1] or the like. In the present specification, the number of the compound is indicated by the compound number described in Table 1 above. For example, a compound denoted by '1' in Table 1 is denoted as 'Compound 1'.

[Synthesis Example 1] Preparation of compound [21]

[Scheme 1]

Preparation of intermediate compound [21-1]

In a 500 mL reaction flask under a nitrogen atmosphere, 50 g (354.36 mmol) of 1-fluoro-2-nitrobenzene, 119.52 g (708.72 mmol) of 4-bromoaniline, and 150 ml of dimethyl sulfoxide were added and stirred under reflux for 18 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using ethyl acetate and hexane, and recrystallized from ethanol to prepare 94.21 g (90.7%) of the intermediate compound [21-1] as a red solid.

Preparation of intermediate compound [21-2]

In a 3L reaction flask under a nitrogen atmosphere, 90 g (307.04 mmol) of the intermediate compound [21-1], 100.39 g (1535.21 mmol) of zinc powder, and 900 mL of ethanol were added and stirred at 0°C. 450 mL of a solution obtained by mixing ethanol, acetic acid and distilled water in a ratio of 2: 1 : 1 is added dropwise at the same temperature and stirred at room temperature for 2 hours. After completion of the reaction, the reactant was slowly added dropwise to 1 L of saturated sodium hydrogen carbonate aqueous solution, stirred for 2 hours, filtered through celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using ethyl acetate and hexane, and then recrystallized from dichloromethane and hexane to prepare 61.24 g (75.8%) of the intermediate compound [21-2] as a yellow solid.

Preparation of intermediate compound [21-3]

In a 1L reaction flask under a nitrogen atmosphere, 60 g (228.02 mmol) of the intermediate compound [21-2] and 63.56 mL (456.05 mmol) of triethylamine were dissolved in 360 mL of chloroform and stirred at 0°C. Ethyl chloroformate 43.41 mL (465.05 mmol) was added dropwise at the same temperature and stirred at room temperature for 2 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and separated and purified by silica gel chromatography using ethyl acetate and hexane to prepare 27.67 g (36.2%) of the intermediate compound [21-3] as a light purple liquid.

Preparation of intermediate compound [21-4]

25 g (74.58 mmol) of the intermediate compound [21-3], 25.54 g (372.91 mmol) of sodium ethoxide, and 2.5 L of ethanol were added to a 5 L reaction flask under a nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was filtered through celite, concentrated under reduced pressure, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and recrystallized with dichloromethane and hexane to prepare 19.56 g (90.7%) of the intermediate compound [21-4] as a white solid.

Preparation of intermediate compound [21-5]

In a 1 L reaction flask under air, 18 g (62.26 mmol) of intermediate compound [21-4], 26.03 mL (186.77 mmol) of triethylamine, 33.92 g (186.77 mmol) of copper(II) acetate, and 540 mL of chloroform in 540 mL of 4-biphenyl While slowly adding 61.64 g (311.28 mmol) of boronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 135 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 23 g (83.7%) of the intermediate compound [21-5] as a white solid.

Preparation of intermediate compound [21-6]

In a 500 mL reaction flask under nitrogen atmosphere, 20 g (45.32 mmol) of intermediate compound [21-5], 17.26 g (67.98 mmol) of bispinacolatodiboron, 6.67 g (67.98 mmol) of potassium acetate, [1,1'-bis(di) Phenylphosphino) ferrocene] dichloropalladium (II) 0.99 g (1.36 mmol) and 1,4-dioxane 200 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 20.76 g (93.8%) of the intermediate compound [21-6] as a white solid.

Preparation of compound [21]

Intermediate compound [21-6] 18g (36.86mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 9.87g (36.86mmol), potassium carbonate 7.64g in a 1L reaction flask under nitrogen atmosphere (55.28mmol), tetrakis(triphenylphosphine)palladium 1.28g (1.11mmol), 1,4-dioxane 360mL, and distilled water 36mL were added and stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 16.15 g (73.8%) of the target compound [21] as a white solid.

[Synthesis Example 2] Preparation of compound 207

[Scheme 2]

Preparation of intermediate compound [207-1]

In the same manner as in [Synthesis Example 1], 1-fluoro-2-nitrobenzene and 3-bromoaniline were used to prepare the intermediate compound [207-1] in a yield of 24.8%.

Preparation of intermediate compound [207-2]

In a 1L reaction flask under air, 15 g (51.88 mmol) of intermediate compound [207-1], 21.69 mL (155.64 mmol) of triethylamine, 28.27 g (155.64 mmol) of copper(II) acetate, and 450 mL of chloroform were placed at room temperature with 3-bromo While slowly adding 44.61 g (259.40 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 115 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 16.40 g (76.1%) of an intermediate compound [207-2] as a white solid.

Preparation of intermediate compound [207-3]

In a 500 mL reaction flask under nitrogen atmosphere, 15 g (36.12 mmol) of intermediate compound [207-2], 13.76 g (54.18 mmol) of bispinacolatodiboron, 5.32 g (54.18 mmol) of potassium acetate, [1,1'-bis(di) Phenylphosphino) ferrocene] dichloropalladium (II) 0.79 g (1.08 mmol) and 1,4-dioxane 150 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 15.15 g (90.7%) of the intermediate compound [207-3] as a white solid.

Preparation of compound [207]

Intermediate compound [207-3] 14g (30.28mmol), 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1] in a 500mL reaction flask under nitrogen atmosphere '-biphenyl]-4-carbonitrile 11.17 g (30.28 mmol), potassium carbonate 6.28 g (45.42 mmol), tetrakis (triphenylphosphine) palladium 1.05 g (0.91 mmol), 1,4-dioxane 280 mL, Add 28 mL of distilled water and stir under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 13.91 g (66.7%) of the target compound [207] as a white solid.

[Synthesis Example 3] Preparation of compound 39

[Scheme 3]

Preparation of intermediate compound [39-1]

In a 1L reaction flask under a nitrogen atmosphere, 80 g (363.64 mmol) of 4-bromo-2-fluoro-1-nitrobenzene, 66.40 ml (727.27 mmol) of aniline, and 240 ml of dimethyl sulfoxide were added and stirred under reflux for 18 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using ethyl acetate and hexane, and then recrystallized from ethanol to prepare 93.9 g (88.1%) of the intermediate compound [39-1] as a red solid.

Preparation of intermediate compound [39-2]

In a 3L reaction flask under a nitrogen atmosphere, 90 g (307.04 mmol) of intermediate compound [39-1], 100.39 g (1535.21 mmol) of zinc powder, and 900 mL of ethanol were added and stirred at 0°C. 450 mL of a solution obtained by mixing ethanol, acetic acid and distilled water in a ratio of 2: 1 : 1 is added dropwise at the same temperature and stirred at room temperature for 2 hours. After completion of the reaction, the reactant was slowly added dropwise to 1 L of saturated sodium hydrogen carbonate aqueous solution, stirred for 2 hours, filtered through celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using ethyl acetate and hexane, and then recrystallized from dichloromethane and hexane to prepare an intermediate compound [39-2] 62.05 g (76.8%) as a yellow solid.

Preparation of intermediate compound [39-3]

In a 1L reaction flask under a nitrogen atmosphere, 62 g (235.62 mmol) of the intermediate compound [39-2] and 65.68 mL (471.25 mmol) of triethylamine were dissolved in 372 mL of chloroform and stirred at 0°C. Ethyl chloroformate 44.86 mL (471.25 mmol) was added dropwise at the same temperature and stirred at room temperature for 2 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and separated and purified by silica gel chromatography using ethyl acetate and hexane to prepare 29.3 g (37.1%) of the intermediate compound [39-3] as a light purple liquid.

Preparation of intermediate compound [39-4]

28 g (83.53 mmol) of the intermediate compound [39-3], 28.61 g (417.66 mmol) of sodium ethoxide, and 2.8 L of ethanol were added to a 5 L reaction flask under a nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was filtered through celite, concentrated under reduced pressure, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then recrystallized from dichloromethane and hexane to prepare 22.03 g (91.2%) of the intermediate compound [39-4] as a white solid.

Preparation of intermediate compound [39-5]

Intermediate compound [39-4] 20g (69.17mmol), phenylboronic acid 12.65g (103.76mmol), potassium carbonate 14.34g (103.76mmol), tetrakis(triphenylphosphine)palladium in a 1L reaction flask under nitrogen atmosphere 2.4 g (2.08 mmol), 400 mL of tetrahydrofuran, and 80 mL of distilled water are added, and the mixture is stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 13.51 g (68.2%) of the intermediate compound [39-5] as a white solid.

Preparation of intermediate compound [39-6]

In a 1 L reaction flask under air, 13 g (45.40 mmol) of intermediate compound [39-5], 18.98 mL (136.21 mmol) of triethylamine, 24.74 g (136.21 mmol) of copper(II) acetate, and 390 mL of chloroform were dissolved in 4-bromo at room temperature. While slowly adding 45.59 g (227.01 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 100 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 16.97 g (84.7%) of the intermediate compound [36-6] as a white solid.

Preparation of intermediate compound [39-7]

15g (33.99mmol) of intermediate compound [39-6], 12.95g (50.98mmol) of bispinacolatodiboron, 5g (50.98mmol) of potassium acetate, [1,1'-bis(diphenyl) in a 500mL reaction flask under nitrogen atmosphere. Phosphino) ferrocene] dichloropalladium (II) 0.75 g (1.02 mmol) and 1,4-dioxane 150 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 15.39 g (92.7%) of the intermediate compound [39-7] as a white solid.

Preparation of compound [39]

15 g (30.71 mmol) of intermediate compound [39-7], 8.22 g (30.71 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 6.37 g of potassium carbonate in a 1L reaction flask under nitrogen atmosphere (46.07 mmol), 1.06 g (0.92 mmol) of tetrakis (triphenylphosphine) palladium, 300 mL of 1,4-dioxane, and 30 mL of distilled water were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the reaction was filtered and recrystallized using acetone, methanol, and toluene to prepare 12.73 g (69.8%) of the target compound [39] as a white solid.

[Synthesis Example 4] Preparation of compound 54

[Scheme 4]

Preparation of intermediate compound [54-1]

In the same manner as in [Synthesis Example 3], the intermediate compound [54-1] was prepared in a yield of 22.8% using 4-bromo-1-fluoro-2-nitrobenzene.

Preparation of intermediate compound [54-2]

Intermediate compound [54-1] 18g (62.26mmol), 3-(dibenzofuranyl)boronic acid 19.8g (93.38mmol), potassium carbonate 12.91g (93.38mmol), tetrakis ( 2.16 g (1.87 mmol) of triphenylphosphine) palladium, 360 mL of tetrahydrofuran, and 72 mL of distilled water were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 15.96 g (68.1%) of the intermediate compound [54-2] as a white solid.

Preparation of intermediate compound [54-3]

In a 1 L reaction flask under air, 15 g (39.85 mmol) of the intermediate compound [54-2], 16.66 mL (119.55 mmol) of triethylamine, 21.71 g (119.55 mmol) of copper(II) acetate, and 450 mL of chloroform in 450 mL of chloroform at room temperature While slowly adding 40.02 g (199.25 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 110 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 16.77 g (79.2%) of the intermediate compound [54-3] as a white solid.

Preparation of intermediate compound [54-4]

In a 500 mL reaction flask under nitrogen atmosphere, 15 g (28.23 mmol) of intermediate compound [54-3], 10.75 g (42.34 mmol) of bispinacolatodiboron, 4.16 g (42.34 mmol) of potassium acetate, [1,1'-bis (di) Phenylphosphino) ferrocene] dichloropalladium (II) 0.62 g (0.85 mmol) and 1,4-dioxane 150 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 14.39 g (88.1%) of the intermediate compound [54-4] as a white solid.

Preparation of compound [54]

13 g (22.47 mmol) of intermediate compound [54-4], 6.02 g (22.47 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 4.66 g of potassium carbonate in a 1L reaction flask under nitrogen atmosphere (33.71 mmol), tetrakis (triphenylphosphine) palladium 0.78 g (0.67 mmol), 1,4-dioxane 260 mL, and distilled water 26 mL were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the reaction was filtered and recrystallized using acetone, methanol, and toluene to prepare 10.89 g (70.9%) of the target compound [54] as a white solid.

[Synthesis Example 5] Preparation of compound 243

[Scheme 5]

Preparation of compound [243-1]

In the same manner as in [Synthesis Example 3], the intermediate compound [243-1] was prepared in a yield of 15.6% using 4-bromo-1-fluoro-2-nitrobenzene.

Preparation of intermediate compound [243-2]

In a 1 L reaction flask under air, 15 g (52.39 mmol) of the intermediate compound [243-1], 21.91 mL (157.16 mmol) of triethylamine, 28.55 g (157.16 mmol) of copper(II) acetate, and 450 mL of chloroform were dissolved in 3-bromo at room temperature. While slowly adding 52.6 g (261.94 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 110 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 18.45 g (79.8%) of the intermediate compound [243-2] as a white solid.

Preparation of intermediate compound [243-3]

Intermediate compound [243-2] 18g (40.79mmol), bispinacolatodiboron 15.54g (61.18mmol), potassium acetate 6g (61.18mmol), [1,1'-bis(diphenyl) in a 500mL reaction flask under nitrogen atmosphere Phosphino) ferrocene] dichloropalladium (II) 0.9 g (1.22 mmol) and 1,4-dioxane 180 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 17.87 g (89.7%) of the intermediate compound [243-3] as a white solid.

Preparation of compound [243]

Intermediate compound [243-3] 15g (30.71mmol), 2-chloro-4-(4-(dibenzo[b,d]furan)4-yl)phenyl)-6-phenyl- in a 1L reaction flask under nitrogen atmosphere 1,3,5-triazine 13.33 g (30.71 mmol), potassium carbonate 6.37 g (46.07 mmol), tetrakis (triphenylphosphine) palladium 1.06 g (0.92 mmol), 1,4-dioxane 300 mL, distilled water 30 mL was added and stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 16.57 g (71%) of the target compound [243] as a white solid.

* [Synthesis Example 6] Preparation of compound 76

[Scheme 6]

Preparation of intermediate compound [76-1]

In a 500 mL reaction flask under a nitrogen atmosphere, 30 g (162.83 mmol) of the compound N-phenyl-o-phenylenediamine and 45.39 mL (325.66 mmol) of triethylamine were dissolved in 180 mL of chloroform and stirred at 0°C. 31 mL (325.66 mmol) of ethyl chloroformate was added dropwise at the same temperature and stirred at room temperature for 2 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and separated and purified by silica gel chromatography using ethyl acetate and hexane to prepare 15.11 g (36.2%) of the intermediate compound [76-1] as a pale purple liquid.

Preparation of intermediate compound [76-2]

15 g (58.53 mmol) of intermediate compound [76-1], 20.04 g (292.63 mmol) of sodium ethoxide, and 1.5 L of ethanol were added to a 3L reaction flask under a nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was filtered through celite, concentrated under reduced pressure, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then recrystallized from dichloromethane and hexane to prepare 11.05 g (89.8%) of the intermediate compound [76-2] as a white solid.

Preparation of intermediate compound [76-3]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.7 mmol) of copper(II) acetate, and 300 mL of chloroform were placed at room temperature with 4-bromo While slowly adding 47.76 g (237.83 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 14.61 g (84.1%) of the intermediate compound [76-3] as a white solid.

Preparation of intermediate compound [76-4]

13g (35.59mmol) of intermediate compound [76-3], 13.56g (53.39mmol) of bispinacolatodiboron, 5.24g (53.39mmol) of potassium acetate, [1,1'-bis(di) in a 500mL reaction flask under nitrogen atmosphere. Phenylphosphino) ferrocene] dichloropalladium (II) 0.78 g (1.07 mmol) and 1,4-dioxane 130 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 13.02 g (88.7%) of the intermediate compound [76-4] as a white solid.

Preparation of compound [76]

Intermediate compound [76-4] 12g (29.11mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine 10.01g ( 29.11 mmol), potassium carbonate 6.03 g (43.66 mmol), tetrakis (triphenylphosphine) palladium 1.01 g (0.87 mmol), 1,4-dioxane 240 mL, and distilled water 24 mL were added and stirred under reflux for 8 hours. After completion of the reaction, the reaction was filtered and recrystallized using acetone, methanol, and toluene to prepare 12.89 g (74.6%) of the target compound [76] as a white solid.

[Synthesis Example 7] Preparation of compound 121

[Scheme 7]

Preparation of intermediate compound [121-1]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.7 mmol) of copper(II) acetate, and 300 mL of chloroform were placed at room temperature with 3-bromo While slowly adding 47.76 g (237.83 mmol) of phenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 14.35 g (82.6%) of the intermediate compound [121-1] as a white solid.

Preparation of intermediate compound [121-2]

In a 500 mL reaction flask under nitrogen atmosphere, 12 g (32.86 mmol) of intermediate compound [121-1], 12.52 g (49.29 mmol) of bispinacolatodiboron, 4.84 g (49.29 mmol) of potassium acetate, [1,1'-bis (di) Phenylphosphino) ferrocene] dichloropalladium (II) 0.72 g (0.99 mmol) and 1,4-dioxane 120 mL were added, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and then separated and purified by silica gel chromatography using dichloromethane and hexane to prepare 12.15 g (89.7%) of the intermediate compound [121-2] as a white solid.

Preparation of compound [121]

10 g (24.25 mmol) of intermediate compound [121-2], 8.34 g of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine ( 24.25 mmol), potassium carbonate 5.03 g (36.38 mmol), tetrakis (triphenylphosphine) palladium 0.84 g (0.73 mmol), 1,4-dioxane 200 mL, and distilled water 20 mL were added and stirred under reflux for 8 hours. After completion of the reaction, the reaction was filtered and recrystallized using acetone, methanol, and toluene to prepare 11.03 g (76.6%) of the target compound [121] as a white solid.

[Synthesis Example 8] Preparation of compound 147

[Scheme 8]

Preparation of compound [147]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.70 mmol) of copper(II) acetate, and 300 mL of chloroform (5-phenyl) at room temperature Pyrazin-2-yl) boronic acid 47.57 g (237.83 mmol) was slowly added thereto and stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 13.38 g (77.2%) of the target compound [147] as a white solid.

[Synthesis Example 9] Preparation of compound 166

[Scheme 9]

Preparation of intermediate compound [166-1]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of the intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.7 mmol) of copper(II) acetate, and 3,5- at room temperature in 300 mL of chloroform While gradually adding 66.53 g (237.83 mmol) of dibromophenylboronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 17.24 g (81.6%) of the intermediate compound [166-1] as a white solid.

Preparation of compound [166]

Intermediate compound [166-1] 15g (33.77mmol), (5-phenylpyrazin-2-yl)boronyl acid 16.89g (84.44mmol), potassium carbonate 7g (50.66mmol), tetrakis in a 1L reaction flask under nitrogen atmosphere 1.17 g (1.01 mmol) of (triphenylphosphine) palladium, 300 mL of tetrahydrofuran, and 60 mL of distilled water were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 13.40 g (66.7%) of the target compound [166] as a white solid.

[Synthesis Example 10] Preparation of compound 340

[Scheme 10]

Preparation of intermediate compound [340-1]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.7 mmol) of copper (II) acetate, and 300 mL of chloroform were dissolved in 6-bromo at room temperature. -3-Pyridinylboronic acid 48g (237.83mmol) was slowly added and stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 12.7 g (72.9%) of the intermediate compound [340-1] as a white solid.

Preparation of compound [340]

Intermediate compound [340-1] 12g (32.77mmol), 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,4-tetramethyl-1,3,2-) in a 500mL reaction flask under nitrogen atmosphere Dioxaborolan-2-yl)phenyl]-1,3,5-triazine 15.69g (36.04mmol), potassium carbonate 6.79g (49.15mmol), tetrakis(triphenylphosphine)palladium 1.14g (0.98mmol) , Add 120 mL of 1,4-dioxane and 12 mL of distilled water, and stir under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 11.44 g (58.7%) of the target compound [340] as a white solid.

[Synthesis Example 11] Preparation of compound 341

[Scheme 11]

Preparation of intermediate compound [341-1]

In a 1 L reaction flask under air, 10 g (47.57 mmol) of intermediate compound [76-2], 19.89 mL (142.7 mmol) of triethylamine, 25.92 g (142.7 mmol) of copper (II) acetate, and 300 mL of chloroform were placed at room temperature with 3-bromobo While gradually adding 47.76 g (237.83 mmol) of ronic acid, the mixture was stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 14.26 g (82.1%) of the intermediate compound [341-1] as a white solid.

Preparation of compound [341]

Intermediate compound [341-1] 10g (27.38mmol), 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-) in a 250mL reaction flask under nitrogen atmosphere Dioxaborolan-2-yl)phenyl]-1,3,5-triazine 13.11g (30.12mmol), potassium carbonate 5.68g (41.07mmol), tetrakis(triphenylphosphine)palladium 0.95g (0.82mmol) , Add 100 mL of 1,4-dioxane and 10 mL of distilled water, and stir under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 11.35 g (69.8%) of the target compound [341] as a white solid.

[Synthesis Example 12] Preparation of comparative compound b

[Scheme 12]

Preparation of comparative compound b

Intermediate compound [76-4] 15g (36.38mmol), 9-bromo-10-phenylanthracene 12.12g (36.38mmol), potassium carbonate 7.54g (54.57mmol), tetrakis(triphenyl) in a 1L reaction flask under nitrogen atmosphere Phosphine) palladium 1.26 g (1.09 mmol), 1,4-dioxane 300 mL, and distilled water 30 mL were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, it was filtered and recrystallized using acetone, methanol, and toluene to prepare 14.08 g (71.9%) of the target compound [Compound b] as a white solid.

Compounds 1 to 345 were prepared according to the preparation methods of Synthesis Examples 1 to 11, and ^{the results of 1} H NMR analysis and mass spectrometry (MS analysis) of each prepared compound are shown in Table 2 below.

compound number ^One H NMR (400 MHz, THF-d ₈ ): δ MS/
Q-TOF(M+) One 8.88 (d, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 to 7.89 (m, 4H), 7.61 to 7.51 (m, 6H), 7.27 (t, 1H), 4.27 (t, 2H), 1.62 (m, 2H), 1.41 to 1.39 (m, 6H), 0.98 (m, 3H) 525 2 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 517 3 8.38 (dd, 4H), 8.23 (d, 2H), 8.09 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.72 (d, 2H), 7.61 (t, 4H), 7.51 (m, 2H), 7.27 (m, 2H) 542 4 8.38 (dd, 4H), 8.23 (d, 2H), 8.0 to 7.85 (m, 6H), 7.76 (dd, 1H), 7.61 to 7.51 (m, 7H), 7.27 (m, 2H) 542 5 8.18 (dd, 4H), 8.03 (d, 2H), 7.89 (d, 1H), 7.77 (d, 2H), 7.69 (m, 2H), 7.61 (t, 1H), 7.52 (dd, 1H), 7.41 ~7.27 (m, 7H), 7.07 (m, 2H) 542 6 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.79 (d, 2H), 7.61 (t, 4H), 7.51 (m, 2H), 7.31 ~7.27 (m, 4H), 2.44 (s, 3H) 531 7 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.83 (t, 1H), 7.61 (t, 4H), 7.51 to 7.38 (m, 4H) , 7.27 (m, 2H), 7.07 (m, 1H), 2.44 (s, 3H) 531 8 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.79 (dd, 1H), 7.61 (t, 4H), 7.51 to 7.48 (m, 3H) , 7.34(t, 1H), 7.27(m, 2H), 7.17(t, 1H), 2.22(s, 3H) 531 9 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.61 (t, 4H), 7.51 (m, 2H), 7.27 (m, 4H), 7.07 (d, 2H), 3.93 (s, 3H) 547 10 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.83 (d, 2H), 7.61 (t, 4H), 7.51 (m, 2H), 7.34 (d, 2H), 7.27 (m, 2H), 1.45 (m, 9H) 573 11 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 4H), 7.61 (t, 4H), 7.51 (m, 2H), 7.32 to 7.27 (m, 4H) 535 12 8.56(d, 2H), 8.38(d, 4H), 8.23(d, 2H), 7.97(d, 2H), 7.89(m, 2H), 7.61(t, 4H), 7.51(m, 2H), 7.27 (m, 2H), 7.09 (d, 2H) 518 13 8.38 (dd, 4H), 8.23 to 8.14 (m, 4H), 7.97 (d, 2H), 7.89 (m, 2H), 7.61 (t, 4H), 7.51 to 7.46 (m, 3H), 7.37 (m, 1H), 7.27 (m, 2H) 518 14 8.38 (dd, 4H), 8.23 (d, 2H), 8.17 (dd, 1H), 7.97 (d, 2H), 7.89 (m, 2H), 7.65 to 7.51 (m, 7H), 7.27 (m, 2H) , 6.80 (dd, 1H), 6.72 (m, 1H) 518 15 8.38 (dd, 4H), 8.23 (d, 2H), 8.17 to 8.12 (m, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.67 to 7.48 (m, 10H), 7.27 (m, 2H), 7.08 (dd, 1H) 567 16 8.38 (d, 5H), 8.27 to 8.23 (m, 3H), 7.97 (d, 2H), 7.89 (m, 2H), 7.67 to 7.51 (m, 9H), 7.27 (m, 2H), 7.09 (dd, 1H) 568 17 8.92 (dd, 1H), 8.78 (dd, 1H), 8.42 to 8.38 (m, 5H), 8.23 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.66 to 7.51 (m, 9H), 7.27 (m, 2H) 568 18 8.38 (dd, 4H), 8.23 (d, 2H), 7.98 to 7.84 (m, 8H), 7.61 to 7.46 (m, 9H), 7.27 (m, 2H) 567 19 8.38 (dd, 4H), 8.32 (dd, 1H), 8.23 (d, 2H), 8.04 to 7.79 (m, 7H), 7.67 to 7.47 (m, 8H), 7.27 (m, 2H) 568 20 9.03 (dd, 2H), 8.38 (dd, 4H), 8.23 to 8.19 (m, 5H), 7.98 to 7.89 (m, 8H), 7.61 to .51 (m, 6H), 7.27 (m, 2H) 617 21 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 4H), 7.89 to 7.87 (m, 4H), 7.62 to 7.51 (m, 11H), 7.27 (m, 2H) 593 22 8.38 (dd, 4H), 8.23 (d, 2H), 8.17 (t, 1H), 7.97 (d, 2H), 7.89 (m, 2H), 7.77 (t, 1H), 7.62 to 7.51 (m, 12H) , 7.36 (m, 1H), 7.27 (m, 2H) 593 23 8.38 (dd, 4H), 8.29 to 7.18 (m, 4H), 8.01 to 7.85 (m, 7H), 7.61 (t, 4H), 7.51 to 7.49 (m, 4H), 7.27 (m, 2H), 7.13 ( t, 1H), 6.93 (dd, 1H) 617 24 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 4H), 7.89 to 7.87 (m, 4H), 7.62 to 7.51 (m, 11H), 7.35 to 7.27 (m, 6H) 669 25 8.38 (dd, 4H), 8.23 (d, 2H), 8.10 to 7.83 (m, 12H), 7.69 to 7.51 (m, 9H), 7.27 (m, 2H) 643 26 8.38 (dd, 4H), 8.23 (d, 2H), 8.13 (s, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.62 to 7.51 (m, 17H), 7.27 (m, 2H) 669 27 8.93 (d, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 7.99 to 7.89 (m, 5H), 7.76 to 7.42 (m, 11H), 7.27 (m, 2H) 607 28 8.71 (d, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 7.99 to 7.89 (m, 6H), 7.76 (dd, 1H), 7.61 to 7.42 (m, 9H), 7.27 (m, 2H) 607 29 8.68 (d, 1H), 8.55 (m, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 8.14 to 8.06 (m, 3H), 7.97 to 7.89 (m, 4H), 7.62 to 7.51 ( m, 8H), 7.27 (m, 2H) 623 30 8.38 to 8.32 (m, 5H), 8.23 (s, 2H), 7.97 (d, 3H), 7.89 (m, 2H), 7.76 (dd, 1H), 7.65 to 7.48 (m, 9H), 7.38 (m, 1H), 7.27 (m, 2H), 1.82 (s, 6H) 633 31 8.38 (dd, 4H), 8.23 (d, 2H), 8.03 to 7.86 (m, 8H), 7.65 to 7.48 (m, 8H), 7.38 (m, 1H), 7.27 (m, 2H), 1.82 (s, 6H) 633 32 8.38 (dd, 4H), 8.23 (d, 2H), 8.03 to 7.85 (m, 10H), 7.61 to 7.6 (m, 17H) 755 33 8.38 (dd, 4H), 8.23 (d, 2H), 8.03 to 7.89 (m, 8H), 7.61 to 7.21 (m, 21H) 757 34 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 5H), 7.62 to 7.51 (m, 18H), 7.35 to 7.29 (m, 3H) 669 35 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.95 (m, 9H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 16H), 7.35 to 7.29 (m, 3H) 719 36 8.38 (dd, 4H), 8.23 (d, 2H), 8.07 (d, 1H), 7.98 to 7.97 (m, 3H), 7.61 to 7.46 (m, 11H), 7.29 (m, 1H) 542 37 8.38 (dd, 4H), 8.23 (d, 2H), 7.97 (d, 2H), 7.78 (d, 1H), 7.61 to 7.44 (m, 11H), 7.29 (m, 1H), 6.81 (dd, 1H) , 3.93(s, 3H) 547 38 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H), 7.62 to 7.51 (m, 16H), 7.29 (m, 1H) 593 39 8.18 (dd, 4H), 8.03 (d, 2H), 7.95 (d, 1H), 7.77 to 7.75 (m, 3H), 7.42 to 7.31 (m, 16H), 7.09 (m, 1H) 593 40 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H) , 7.67~7.51(m, 12H), 7.29(m, 1H) 594 41 8.85 (d, 2H), 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 to 8.09 (m, 3H), 7.97 to 7.95 (m, 3H), 7.61 to 7.51 (m, 11H), 7.29 ( m, 1H) 594 42 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H), 7.62 to 7.51 (m, 16H), 7.35 to 7.29 (m, 5H) 669 43 8.38 (m, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H), 7.80 (t, 1H), 7.67 to 7.51 (m, 19H), 7.29 (m, 1H) 669 44 9.09 (d, 1H), 9.03 (dd, 1H), 8.44 (s, 1H), 8.38 (dd, 4H), 8.23 to 8.15 (m, 5H), 7.98 to 7.92 (m, 5H), 7.81 (s, 2H), 7.61 to 7.51 (m, 11H), 7.29 (m, 1H) 693 45 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 4H), 8.23 to 8.14 (m, 5H), 7.97 to 7.95 (m, 3H), 7.71 to 7.51 (m, 14H), 7.29 ( m, 1H) 643 46 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 to 7.95 (m, 7H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 14H), 7.29 (m, 1H) 643 47 8.66 (d, 1H), 8.52 (d, 1H), 8.38 (dd, 4H), 8.23 (dd, 2H), 8.12 (dd, 1H), 8.02 to 7.97 (m, 4H), 7.73 (m, 1H) , 7.61 to 7.51 (m, 12H), 7.29 (m, 1H), 7.20 (dd, 1H) 644 48 8.93 (dd, 1H), 8.48 (m, 1H), 8.38 to 8.23 (m, 7H), 8.15 to 8.12 (m, 2H), 7.97 to 7.95 (m, 3H), 7.76 to 7.51 (m, 13H), 7.29 (m, 1H) 644 49 8.66 (d, 1H), 8.38 (dd, 4H), 8.23 to 8.08 (m, 6H), 7.98 to 7.88 (m, 4H), 7.70 to 7.45 (m, 12H), 7.29 (m, 1H) 644 50 9.01 (d, 1H), 8.55 (d, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 8.08 to 7.95 (m, 5H), 7.87 (dd, 1H) , 7.61~7.51(m, 12H), 7.29(m, 1H) 644 51 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.95 (m, 4H), 7.85 (dd, 1H), 7.76 to 7.72 (m, 2H), 7.61 to 7.42 ( m, 14H), 7.29 (m, 1H) 683 52 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.91 (m, 5H), 7.82 to 7.76 (m, 3H), 7.61 to 7.42 (m, 13H), 7.29 ( m, 1H) 683 53 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 8.05 to 7.95 (m, 5H), 7.85 (dd, 1H), 7.76 to 7.74 (m, 2H), 7.61 to 7.42 ( m, 13H), 7.29 (m, 1H) 683 54 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.91 (m, 6H), 7.76 (dd, 1H), 7.61 to 7.42 (m, 14H), 7.29 (m, 1H) 683 55 8.55 (m, 1H), 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 8.08 to 7.92 (m, 6H), 7.66 to 7.51 (m, 14H), 7.29 (m, 1H) 699 56 8.55 (m, 1H), 8.38 (dd, 4H), 8.23 to 8.08 (m, 7H), 7.97 to 7.95 (m, 3H), 7.62 to 7.51 (m, 13H), 7.29 (m, 1H) 699 57 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 4H), 7.73 (dd, 1H), 7.65 to 7.29 (m, 17H), 1.82 (s, 6H) 709 58 8.38 (dd, 4H), 8.23 (d, 2H), 8.16 to 8.15 (m, 2H), 7.97 to 7.95 (m, 4H), 7.71 to 7.48 (m, 15H), 7.38 to 7.29 (m, 2H), 1.82(s, 6H) 709 59 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 8.03 to 7.95 (m, 5H), 7.87 (d, 1H), 7.73 (dd, 1H), 7.65 to 7.48 (m, 13H), 7.38~7.29(m, 2H), 1.82(s, 6H) 709 60 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.93 (m, 5H), 7.65 to 7.48 (m, 15H), 7.38 to 7.29 (m, 2H), 1.82 ( s, 6H) 709 61 8.40 to 8.38 (m, 4H), 8.00 (d, 2H), 7.89 (m, 2H), 7.64 to 7.53 (m, 8H), 7.29 to 7.27 (m, 3H), 6.96 (d, 2H) 439 62 8.40 to 8.38 (m, 4H), 8.30 (s, 2H), 8.00 (d, 2H), 7.89 (m, 2H), 7.64 to 7.51 (m, 12H), 7.29 to 7.27 (m, 3H) 515 63 8.33 (s, 1H), 8.23 (d, 2H), 7.97 to 7.89 (m, 8H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 516 64 8.38 (dd, 2H), 8.33 (s, 1H), 7.97 to 7.89 (m, 8H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 516 65 8.33 (s, 1H), 7.97 to 7.89 (m, 10H), 7.62 to 7.51 (m, 12H), 7.35 to 7.27 (m, 5H) 592 66 8.38 (dd, 2H), 8.33 (s, 1H), 7.97 to 7.80 (m, 8H), 7.67 to 7.51 (m, 14H), 7.29 to 7.27 (m, 3H) 592 67 8.40 to 8.38 (m, 5H), 7.97 to 7.87 (m, 8H), 7.62 to 7.51 (m, 12H), 7.29 to 7.27 (m, 3H) 592 68 9.29 (s, 1H), 8.69 (dd, 1H), 8.50 (dd, 1H), 8.23 (d, 2H), 7.97 to 7.89 (m, 7H), 7.61 to 7.46 (m, 8H), 7.29 to 7.27 ( m, 3H) 517 69 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.39 (s, 1H), 8.23 (d, 2H), 7.97 to 7.89 (m, 6H), 7.67 to 7.51 (m, 8H), 7.29 to 7.27 (m, 3H) 517 70 8.85 (d, 2H), 8.39 (s, 1H), 8.23 (d, 2H), 8.09 (d, 2H), 7.97 to 7.89 (m, 6H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 ( m, 3H) 517 71 9.34 (d, 1H), 8.80 (dd, 1H), 8.69 (s, 1H), 8.52 (m, 1H), 7.97 to 7.87 (m, 8H), 7.67 to 7.51 (m, 8H), 7.29 to 7.27 ( m, 3H) 517 72 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.33 (s, 1H), 7.97 to 7.87 (m, 10H), 7.67 to 7.51 (m, 8H), 7.35 to 7.27 ( m, 5H) 593 73 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.40 to 8.33 (m, 5H), 7.97 to 7.87 (m, 6H), 7.67 to 7.51 (m, 8H), 7.35 to 7.27 (m, 5H) 593 74 8.38 (dd, 2H), 8.33 (s, 1H), 7.97 to 7.80 (m, 8H), 7.67 to 7.51 (m, 14H), 7.29 to 7.27 (m, 3H) 592 75 8.34 to 8.33 (m, 2H), 7.97 (d, 2H), 7.89 to 7.80 (m, 7H), 7.67 to 7.51 (m, 18H), 7.29 to 7.27 (m, 3H) 668 76 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.89 (m, 6H), 7.62 to 7.51 (m, 12H), 7.35 to 7.27 (m, 5H) 593 77 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.89 (m, 6H), 7.67 to 7.51 (m, 8H), 7.35~7.27(m, 5H) 594 78 8.91 (d, 2H), 8.60 (dd, 1H), 8.38 (dd, 2H), 8.23 (dd, 2H), 7.98 to 7.89 (m, 6H), 7.61 to 7.51 (m, 8H), 7.36 to 7.27 ( m, 4H), 7.10 (m, 1H) 594 79 8.85 (d, 2H), 8.38 (dd, 2H), 8.23 (dd, 2H), 8.09 (d, 2H), 7.97 to 7.89 (m, 6H), 7.61 to 7.51 (m, 7H), 7.35 to 7.27 ( m, 5H) 594 80 8.23 (d, 2H), 7.97 to 7.89 (m, 8H), 7.62 to 7.51 (m, 14H), 7.35 to 7.27 (m, 7H) 669 81 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.89 (m, 6H), 7.62 to 7.51 (m, 12H), 7.35 to 7.27 (m, 9H) 669 82 8.38 (dd, 2H), 8.23 (d, 2H), 8.07 (d, 2H), 7.97 to 7.89 (m, 6H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 (m, 3H) 542 83 8.66 (m, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 7.98 to 7.79 (m, 7H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 (m, 3H) 542 84 8.38 (dd, 2H), 8.23 (d, 2H), 8.07 (dd, 1H), 7.97 to 7.80 (m, 6H), 7.69 to 7.51 (m, 8H), 7.29 to 7.27 (m, 3H) 542 85 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.89 (m, 10H), 7.61 to 7.51 (m, 7H), 7.35 to 7.27 (m, 5H) 618 86 8.18 (dd, 2H), 8.03 (d, 2H), 7.78 to 7.59 (m, 10H), 7.41 to 7.31 (m, 7H), 7.15 to 7.07 (m, 5H) 618 87 8.38 to 8.34 (m, 3H), 8.23 (d, 2H), 7.97 to 7.89 (m, 8H), 7.80 (m, 1H), 7.67 to 7.51 (m, 9H), 7.29 to 7.27 (m, 3H) 618 88 8.38~8.34(m, 3H), 8.23(d, 2H), 7.98~7.79(m, 9H), 7.67~7.51(m, 9H), 7.29~7.27(m, 3H) 618 89 8.23 to 8.19 (m, 4H), 7.97 to 7.89 (m, 6H), 7.57 to 7.49 (m, 6H), 7.29 to 7.27 (m, 5H), 2.44 (s, 6H) 545 90 8.38 (dd, 2H), 8.23 (d, 2H), 8.07 (d, 2H), 7.97 (d, 2H), 7.89 (m, 2H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 (m, 3H), 7.15 (d, 2H), 3.93 (s, 3H) 547 91 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 8.05 (dd, 1H), 7.97 (d, 2H), 7.89 (m, 2H), 7.71 to 7.51 (m, 10H), 7.29~7.27(m, 3H) 567 92 8.93 (dd, 1H), 8.48 (m, 1H), 8.38 to 8.23 (m, 5H), 8.12 (m, 1H), 7.97 to 7.89 (m, 4H), 7.76 to 7.51 (m, 9H), 7.29 to 7.27 (m, 3H) 568 93 8.61 (d, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.02 to 7.89 (m, 5H), 7.73 (m, 1H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 ( m, 3H) 568 94 9.19 (m, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.89 (m, 7H), 7.69 to 7.51 (m, 9H), 7.29 to 7.27 ( m, 3H) 567 95 8.54 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.08 (m, 4H), 7.97 to 7.88 (m, 5H), 7.70 to 7.51 (m, 9H), 7.29 to 7.27 (m, 3H) 568 96 9.01 (d, 1H), 8.55 (d, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.08 to 7.87 (m, 7H), 7.61 to 7.51 (m, 8H), 7.29 to 7.27 ( m, 3H) 568 97 8.65 (m, 2H), 8.18 to 7.89 (m, 12H), 7.71 to 7.53 (m, 10H), 7.29 to 7.27 (m, 3H) 617 98 9.19 (t, 2H), 8.59 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.89 (m, 10H), 7.69 (m, 4H), 7.57 to 7.53 (m, 4H), 7.29 to 7.27 ( m, 3H) 617 99 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 7.97 to 7.89 (m, 6H), 7.71 to 7.51 (m, 10H), 7.35 to 7.27 (m, 5H) 643 100 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.89 (m, 10H), 7.69 to 7.51 (m, 10H), 7.35 to 7.27 (m, 5H) 643 101 8.38 (dd, 2H), 8.23 (d, 2H), 8.03 to 7.87 (m, 7H), 7.73 (dd, 1H), 7.65 to 7.48 (m, 9H), 7.38 to 7.27 (m, 4H), 1.82 ( s, 6H) 633 102 8.38 (dd, 2H), 8.23 (d, 2H), 8.05 to 7.89 (m, 7H), 7.76 to 7.74 (m, 2H), 7.61 to 7.42 (m, 9H), 7.29 to 7.27 (m, 3H) 607 103 8.55 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.18 (m, 4H), 8.08 (m, 1H), 7.97 to 7.89 (m, 5H), 7.62 to 7.51 (m, 9H), 7.29 to 7.27 (m, 3H) 623 104 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.89 (m, 8H), 7.65 to 7.48 (m, 11H), 7.38 to 7.27 (m, 6H), 1.82 (s, 6H) 709 105 8.38 (dd, 2H), 8.23 (d, 2H), 7.99 to 7.89 (m, 9H), 7.76 (dd, 1H), 7.61 to 7.27 (m, 15H) 683 106 8.68 (m, 1H), 8.40 (dd, 2H), 8.14 (m, 1H), 7.89 to 7.80 (m, 3H), 7.64 to 7.53 (m, 9H), 7.29 to 7.27 (m, 3H), 6.96 ( d, 2H) 439 107 8.68 (m, 1H), 8.40 (dd, 2H), 8.30 (s, 2H), 8.14 (m, 1H), 7.89 to 7.80 (m, 3H), 7.64 to 7.51 (m, 13H), 7.29 to 7.27 ( m, 3H) 515 108 8.33 (s, 1H), 8.17 to 8.12 (m, 2H), 7.89 (m, 6H), 7.77 (t, 1H), 7.61 to 7.51 (m, 11H), 7.29 to 7.27 (m, 3H) 516 109 8.68 (t, 1H), 8.40 (dd, 2H), 8.14 (m, 1H), 7.89 to 7.80 (m, 3H), 7.64 to 7.53 (m, 9H), 7.29 to 7.27 (m, 3H), 6.96 ( d, 2H) 439 110 8.68 (t, 1H), 8.40 (dd, 2H), 8.30 (s, 2H), 8.14 (m, 1H), 7.89 to 7.80 (m, 3H), 7.64 to 7.51 (m, 13H), 7.29 to 7.27 ( m, 3H) 515 111 8.33 (s, 1H), 8.17 to 8.12 (m, 2H), 7.89 (m, 6H), 7.77 (t, 1H), 7.61 to 7.51 (m, 11H), 7.29 to 7.27 (m, 3H) 516 112 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.39 (s, 1H), 8.17 to 8.12 (m, 2H), 7.89 (m, 4H), 7.77 (t, 1H) , 7.67~7.51(m, 9H), 7.29~7.27(m, 3H) 517 113 8.96 (s, 1H), 8.38 (dd, 2H), 8.17 (t, 1H), 7.89 (m, 4H), 7.77 (t, 1H), 7.61 to 7.51 (m, 11H), 7.36 to 7.27 (m, 4H) 516 114 8.33 (s, 1H), 8.17 (t, 1H), 7.95 to 7.89 (m, 6H), 7.77 (t, 1H), 7.63 to 7.51 (m, 14H), 7.35 to 7.27 (m, 5H) 592 115 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.33 (s, 1H), 8.17 (t, 1H), 7.95 to 7.89 (m, 6H), 7.77 (t, 1H) , 7.67~7.51(m, 10H), 7.35~7.27(m, 5H) 593 116 8.38 (dd, 2H), 8.33 (s, 1H), 8.17 (t, 1H), 7.89 to 7.77 (m, 5H), 7.67 to 7.51 (m, 16H), 7.29 to 7.27 (m, 3H) 592 117 9.11 (s, 1H), 8.92 (d, 3H), 8.86 (dd, 2H), 7.98 (d, 1H), 7.92 to 7.72 (m, 8H), 7.66 to 7.59 (m, 5H), 7.51 to 7.41 ( m, 4H), 7.32 (m, 1H), 7.23 (m, 1H), 7.16 (m, 2H) 592 118 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.40 to 8.33 (m, 5H), 8.17 (t, 1H), 7.89 (m, 2H), 7.77 (t, 1H) , 7.67~7.51(m, 10H), 7.35~7.27(m, 5H) 593 119 8.38 (dd, 4H), 8.17 to 8.12 (m, 2H), 7.89 (m, 2H), 7.77 (t, 1H), 7.61 to 7.51 (m, 11H), 7.29 to 7.27 (m, 3H) 517 120 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.89 to 7.87 (m, 4H), 7.77 (t, 1H), 7.61 to 7.51 (m, 8H), 7.40 (t, 2H), 7.29 to 7.27 (m, 3H) 535 121 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.95 to 7.89 (m, 4H), 7.77 (t, 1H), 7.62 to 7.51 (m, 13H), 7.35 to 7.27 (m, 5H) 593 122 8.91 (d, 2H), 8.60 (dd, 1H), 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.98 to 7.89 (m, 4H), 7.77 (t, 1H), 7.61 to 7.51 ( m, 9H), 7.36 to 7.27 (m, 4H), 7.10 (m, 1H) 594 123 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.95 to 7.89 (m, 4H), 7.77 (t, 1H), 7.67 to 7.51 (m, 9H), 7.35 to 7.27 (m, 5H) 594 124 8.85 (d, 2H), 8.38 (dd, 2H), 8.17 to 8.09 (m, 4H), 7.95 to 7.89 (m, 4H), 7.77 (t, 1H), 7.61 to 7.51 (m, 8H), 7.35 to 7.27 (m, 5H) 594 125 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.95 to 7.89 (m, 4H), 7.77 (t, 1H), 7.62 to 7.51 (m, 13H), 7.35 to 7.27 (m, 9H) 669 126 8.38 (dd, 2H), 8.17 to 8.07 (m, 4H), 7.92 to 7.89 (m, 4H), 7.77 (t, 1H), 7.61 to 7.51 (m, 8H), 7.29 to 7.27 (m, 3H) 542 127 8.66 (m, 1H), 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.98 (dd, 1H), 7.89 to 7.77 (m, 5H), 7.61 to 7.51 (m, 8H), 7.29 to 7.27 (m, 3H) 542 128 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.95 to 7.89 (m, 8H), 7.77 (t, 1H), 7.61 to 7.51 (m, 8H), 7.35 to 7.27 (m, 5H) 618 129 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.98 to 7.77 (m, 9H), 7.61 to 7.51 (m, 8H), 7.35 to 7.27 (m, 5H) 618 130 8.38~8.34(m, 3H), 8.17~8.12(m, 2H), 7.94~7.89(m, 6H), 7.80~7.77(m, 2H), 7.67~7.51(m, 10H), 7.29~7.27(m) , 3H) 618 131 8.38 to 8.34 (m, 3H), 8.17 to 8.12 (m, 2H), 7.98 to 7.77 (m, 8H), 7.67 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 618 132 8.19~8.12(m, 4H), 7.89(m, 4H), 7.77(t, 1H), 7.53~7.49(m, 7H), 7.29~7.27(m, 5H), 2.44(s, 6H) 545 133 8.38 (dd, 2H), 8.17 to 8.07 (m, 4H), 7.89 (m, 2H), 7.77 (t, 1H), 7.61 to 7.51 (m, 8H), 7.29 to 7.27 (m, 3H), 7.15 ( d, 2H), 3.93 (s, 3H) 547 134 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 8.05 (m, 5H), 7.89 (m, 2H), 7.77 to 7.51 (m, 12H), 7.29 to 7.27 (m, 3H) 567 135 8.93 (d, 1H), 8.48 (m, 1H), 8.38 (dd, 2H), 8.31 (dd, 1H), 8.17 to 8.12 (m, 3H), 7.89 (m, 2H), 7.77 to 7.51 (m, 11H), 7.29~7.27(m, 3H) 568 136 8.61 (d, 1H), 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 8.02 (dd, 1H), 7.89 (m, 2H), 7.77 to 7.73 (m, 2H), 7.61 to 7.51 ( m, 11H), 7.29 to 7.27 (m, 3H) 568 137 9.19 (s, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 8.02 (m, 5H), 7.89 (m, 2H), 7.77 to 7.61 (m, 11H), 7.29 to 7.27 ( m, 3H) 567 138 8.54 (dd, 1H), 8.38 (dd, 2H), 8.17 to 8.08 (m, 4H), 7.89 to 7.88 (m, 3H), 7.77 to 7.61 (m, 11H), 7.29 to 7.27 (m, 3H) 568 139 9.01 (s, 1H), 8.55 (d, 1H), 8.38 (dd, 2H), 8.17 to 8.03 (m, 4H), 7.89 to 7.87 (m, 3H), 7.77 (t, 1H), 7.61 to 7.51 ( m, 9H), 7.29 to 7.27 (m, 3H) 568 140 8.38 (dd, 2H), 8.17 to 7.61 (m, 22H), 7.35 to 7.27 (m, 5H) 643 141 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 8.03 (d, 1H), 7.97 (dd, 1H), 7.89 to 7.87 (m, 3H), 7.77 to 7.73 (m, 2H), 7.65 to 7.48(m, 10H), 7.38~7.27(m, 4H), 1.82(s, 6H) 633 142 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.97 (dd, 1H), 7.89 (m, 2H), 7.77 to 7.73 (m, 2H), 7.65 to 7.27 (m, 16H), 1.82 ( s, 6H) 633 143 8.38 (dd, 2H), 8.17 to 7.99 (m, 4H), 7.89 to 7.74 (m, 6H), 7.61 to 7.42 (m, 10H), 7.29 to 7.27 (m, 3H) 607 144 8.55 (m, 1H), 8.38 (dd, 2H), 8.21 to 8.08 (m, 5H), 7.92 to 7.89 (m, 3H), 7.77 (t, 1H), 7.62 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 623 145 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.97 to 7.89 (m, 6H), 7.77 (t, 1H), 7.65 to 7.48 (m, 12H), 7.38 to 7.27 (m, 6H), 1.82(s, 6H) 709 146 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.99 to 7.89 (m, 7H), 7.77 to 7.76 (m, 2H), 7.61 to 7.27 (m, 16H) 683 147 8.46 (s, 1H), 8.23 (dd, 2H), 8.16 (s, 1H), 7.89 (m, 2H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 (m, 3H) 364 148 8.46(s, 1H), 8.16(s, 1H), 8.07(d, 2H), 7.92~7.89(m, 4H), 7.57~7.53(m, 4H), 7.29~7.27(m, 3H) 389 149 8.46 (s, 1H), 8.17 to 8.16 (m, 2H), 7.89 to 7.79 (m, 5H), 7.57 to 7.53 (m, 4H), 7.29 to 7.27 (m, 3H) 389 150 8.69 (dd, 1H), 8.50 (dd, 1H), 8.46 (s, 1H), 8.16 (s, 1H), 7.95 to 7.89 (m, 3H), 7.57 to 7.46 (m, 5H), 7.29 to 7.27 ( m, 3H) 365 151 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 to 8.46 (m, 2H), 8.16 (s, 1H), 7.89 (m, 2H), 7.67 (t, 1H), 7.57 to .53 (m) , 4H), 7.29~7.27 (m, 3H) 365 152 8.85 (d, 2H), 8.46 (s, 1H), 8.16 to 8.09 (m, 3H), 7.89 (m, 2H), 7.57 to 7.53 (m, 4H), 7.29 to 7.27 (m, 3H) 365 153 8.46(s, 1H), 8.25(m, 2H), 8.16(s, 1H), 7.89(m, 2H), 7.57~7.53(m, 4H), 7.40~7.27(m, 5H) 382 154 8.89 (s, 2H), 8.23 (dd, 2H), 7.97 to 7.87 (m, 6H), 7.61 to 7.51 (m, 7H), 7.29 to 7.27 (m, 3H) 440 155 8.89 (s, 2H), 8.07 (d, 2H), 7.92 to 7.87 (m, 8H), 7.57 to 7.53 (m, 4H), 7.29 to 7.27 (m, 3H) 465 156 8.89 (s, 2H), 8.17 (m, 1H), 7.98 to 7.79 (m, 9H), 7.57 to 7.53 (m, 4H), 7.29 to 7.27 (m, 3H) 465 157 8.89 (s, 2H), 8.69 (dd, 1H), 8.50 (dd, 1H), 7.97 to 7.87 (m, 7H), 7.57 to 7.46 (m, 5H), 7.29 to 7.27 (m, 3H) 441 158 9.34 (d, 1H), 8.89 (s, 2H), 8.80 (dd, 1H), 7.52 (m, 1H), 7.97 to 7.87 (m, 6H), 7.67 (t, 1H), 7.57 to 7.53 (m, 4H), 7.29~7.27(m, 3H) 441 159 8.89 (s, 2H), 8.25 (m, 2H), 7.97 to 7.87 (m, 6H), 7.57 to 7.53 (m, 4H), 7.40 (t, 2H), 7.29 to 7.27 (m, 3H) 458 160 8.89 (s, 2H), 8.23 to 8.17 (m, 3H), 7.89 (m, 2H), 7.77 (t, 1H), 7.63 to 7.51 (m, 9H), 7.29 to 7.27 (m, 3H) 440 161 8.89(s, 2H), 8.17(t, 1H), 8.07(d, 2H), 7.92~7.89(m, 4H), 7.77(t, 1H), 7.63~7.53(m, 6H), 7.29~7.27( m, 3H) 465 162 8.89 (s, 2H), 8.17 (m, 2H), 7.98 to 7.77 (m, 6H), 7.63 to 7.53 (m, 6H), 7.29 to 7.27 (m, 3H) 465 163 8.89 (s, 2H), 8.69 (dd, 1H), 8.50 (dd, 1H), 8.17 (m, 1H), 7.95 to 7.89 (m, 3H), 7.77 (t, 1H), 7.63 to 7.46 (m, 7H), 7.29~7.27(m, 3H) 441 164 9.34(d, 1H), 8.89(s, 2H), 8.80(dd, 1H), 8.52(m, 1H), 8.17(m, 1H), 7.89(m, 2H), 7.77(t, 1H), 7.67 ~7.53(m, 7H), 7.29~7.27(m, 3H) 441 165 8.89(s, 2H), 8.25~8.17(m, 3H), 7.89(m, 2H), 7.77(t, 1H), 7.63~7.53(m, 6H), 7.40(t, 2H), 7.29~7.27( m, 3H) 458 166 8.89 (s, 4H), 8.23 (dd, 4H), 8.13 (d, 2H), 7.89 (m, 2H), 7.61 to 7.51 (m, 11H), 7.29 to 7.27 (m, 3H) 594 167 8.89 (s, 4H), 8.13 to 8.07 (m, 6H), 7.92 to 7.89 (m, 6H), 7.57 to 7.53 (m, 5H), 7.29 to 7.27 (m, 3H) 644 168 8.89 (s, 4H), 8.69 (dd, 2H), 8.50 (dd, 2H), 8.13 (d, 2H), 7.95 to 7.89 (m, 4H), 7.57 to 7.46 (m, 7H), 7.29 to 7.27 ( m, 3H) 596 169 8.89 (s, 4H), 8.23 (dd, 4H), 7.97 to 7.87 (m, 6H), 7.76 (s, 3H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 670 170 8.89 (s, 4H), 8.23 to 8.17 (m, 5H), 7.89 (m, 2H), 7.77 to 7.76 (m, 4H), 7.61 to 7.51 (m, 11H), 7.36 to 7.27 (m, 4H) 670 171 8.38 (dd, 2H), 8.23 to 8.12 (m, 4H), 7.97 to 7.89 (m, 6H), 7.67 to 7.48 (m, 12H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 643 172 8.23 (m, 1H), 8.38 (dd, 2H), 8.23 to 7.89 (m, 11H), 7.71 to 7.51 (m, 8H), 7.51 to 7.48 (m, 2H), 7.27 (m, 2H), 7.08 ( dd, 1H) 617 173 9.19 (s, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 to 7.89 (m, 11H), 7.69 to 7.48 (m, 9H), 7.27 (m, 2H), 7.08 (dd, 1H) 617 174 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.12 (m, 6H), 7.97 to 7.89 (m, 6H), 7.71 to 7.61 (m, 8H), 7.51 to 7.48 (m, 2H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 693 175 8.38 (dd, 2H), 8.23 to 7.83 (m, 14H), 7.69 to 7.48 (m, 10H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 693 176 8.38 (dd, 2H), 8.23 to 7.89 (m, 11H), 7.74 to 7.42 (m, 11H), 7.27 (m, 2H), 7.08 (dd, 1H) 657 177 8.38 (dd, 2H), 8.23 to 8.12 (m, 4H), 7.99 to 7.89 (m, 9H), 7.76 (dd, 1H), 7.67 to 7.27 (m, 14H), 7.08 (dd, 1H) 733 178 8.38 (dd, 2H), 8.23 to 8.12 (m, 4H), 7.97 to 7.89 (m, 10H), 7.67 to 7.51 (m, 5H), 7.51 to 7.48 (m, 2H), 7.35 to 7.27 (m, 4H) ), 7.08 (dd, 1H) 668 179 8.38~8.34(m, 3H), 8.23~7.12(m, 4H), 7.97~7.89(m, 8H), 7.80(t, 1H), 7.67~7.48(m, 9H), 7.27(m, 2H), 7.08 (dd, 1H) 668 180 8.38 (dd, 4H), 8.17 to 8.12 (m, 4H), 7.89 (m, 2H), 7.77 (t, 1H), 7.67 to 7.48 (m, 11H), 7.27 (m, 2H), 7.08 (dd, 1H) 567 181 8.38 (dd, 2H), 8.17 to 8.12 (m, 4H), 7.95 to 7.89 (m, 4H), 7.77 (t, 1H), 7.67 to 7.48 (m, 13H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 643 182 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 8.05 (m, 7H), 7.89 (m, 2H), 7.71 to 7.48 (m, 12H), 7.27 (m, 2H), 7.08 (dd, 1H) 617 183 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 8.02 (m, 7H), 7.89 (m, 2H), 7.77 to 7.48 (m, 11H), 7.27 (m, 2H), 7.08 (dd, 1H) 617 184 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 6H), 7.95 to 7.89 (m, 4H), 7.77 to 7.48 (m, 12H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 693 185 8.38 (dd, 2H), 8.17 to 7.48 (m, 24H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 693 186 8.38 (dd, 2H), 8.17 to 7.89 (m, 6H), 7.77 to 7.42 (m, 16H), 7.27 (m, 2H), 7.08 (dd, 1H) 657 187 8.38 (dd, 2H), 8.17 to 8.12 (m, 4H), 7.99 to 7.89 (m, 7H), 7.77 to 7.76 (m, 2H), 7.67 to 7.35 (m, 15H), 7.08 (dd, 1H) 733 188 8.38 (dd, 2H), 8.17 to 8.12 (m, 4H), 7.95 to 7.89 (m, 8H), 7.77 (t, 1H), 7.67 to 7.48 (m, 8H), 7.35 to 7.27 (m, 4H), 7.08 (dd, 1H) 668 189 8.38~8.34(m, 3H), 8.17~8.12(m, 4H), 7.94~7.89(m, 6H), 7.80~7.77(m, 2H), 7.67~7.48(m, 10H), 7.27(m, 2H) ), 7.08 (dd, 1H) 668 190 8.38 (dd, 2H), 8.23 (d, 2H), 7.98 to 7.84 (m, 10H), 7.62 to 7.46 (m, 11H), 7.35 to 7.27 (m, 4H) 643 191 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 8.05 to 7.84 (m, 9H), 7.71 to 7.46 (m, 9H), 7.27 (m, 2H) 617 192 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.84 (m, 11H), 7.69 to 7.46 (m, 8H), 7.27 (m, 2H) 617 193 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 7.98 to 7.87 (m, 10H), 7.71 to 7.46 (m, 9H), 7.35 to 7.27 (m, 4H) 693 194 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.83 (m, 14H), 7.69 to 7.46 (m, 9H), 7.35 to 7.27 (m, 4H) 693 195 8.38 (dd, 2H), 8.23 (d, 2H), 8.05 to 7.85 (m, 11H), 7.76 to 7.74 (m, 2H), 7.61 to 7.42 (m, 8H), 7.27 (m, 2H) 657 196 8.38 (dd, 2H), 8.23 (d, 2H), 7.99 to 7.84 (m, 13H), 7.76 (dd, 1H), 7.61 to 7.27 (m, 13H) 733 197 8.38 (dd, 2H), 8.23 (d, 2H), 7.98 to 7.89 (m, 14H), 7.61 to 7.46 (m, 6H), 7.35 to 7.27 (m, 4H) 668 198 8.38~8.34(m, 3H), 8.23(d, 2H), 7.98~7.80(m, 13H), 7.67~7.46(m, 8H), 7.27(m, 2H) 668 199 8.38 (dd, 4H), 8.17 to 8.12 (m, 2H), 7.98 to 7.77 (m, 7H), 7.61 to 7.46 (m, 10H), 7.27 (m, 2H) 567 200 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.98 to 7.77 (m, 9H), 7.61 to 7.46 (m, 12H), 7.35 to 7.27 (m, 4H) 643 201 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 7.46 (m, 21H), 7.27 (m, 2H) 617 202 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 7.12 (m, 4H), 7.98 to 7.46 (m, 19H), 7.35 to 7.27 (m, 4H) 693 203 8.38 (dd, 2H), 8.17 to 7.46 (m, 25H), 7.35 to 7.27 (m, 4H) 693 204 8.38 (dd, 2H), 8.17 to 7.74 (m, 14H), 7.61 to 7.46 (m, 9H), 7.27 (m, 2H) 657 205 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.99 to 7.77 (m, 13H), 7.61 to 7.27 (m, 14H) 733 206 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.98 to 7.84 (m, 12H), 7.77 (t, 1H), 7.61 to 7.46 (m, 7H), 7.35 to 7.27 (m, 4H) 668 207 8.38~8.34(m, 3H), 8.17~8.12(m, 2H), 7.98~7.77(m, 12H), 7.67~7.46(m, 9H), 7.27(m, 2H) 668 208 8.89 (s, 2H), 8.23 (dd, 2H), 7.98 to 7.87 (m, 10H), 7.61 to 7.46 (m, 6H), 7.27 (m, 2H) 490 209 8.89 (s, 2H), 8.23 to 8.17 (m, 3H), 7.98 to 7.77 (m, 7H), 7.63 to 7.46 (m, 8H), 7.27 (m, 2H) 490 210 8.89 (s, 4H), 8.23 to 8.12 (m, 8H), 7.89 (m, 2H), 7.67 to 7.48 (m, 11H), 7.27 (m, 2H), 7.08 (dd, 1H) 644 211 8.89 (s, 4H), 8.23 (dd, 4H), 8.13 (d, 2H), 7.98 to 7.84 (m, 6H), 7.61 to 7.46 (m, 10H), 7.27 (m, 2H) 644 212 8.89 (s, 4H), 8.23 to 8.17 (m, 5H), 7.98 to 7.76 (m, 10H), 7.61 to 7.46 (m, 10H), 7.36 (m, 1H), 7.27 (m, 2H) 720 213 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.87 (m, 10H), 7.62 to 7.51 (m, 13H), 7.35 (d, 2H), 7.27 (m, 2H) 669 214 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 8.05 to 7.87 (m, 9H), 7.71 to 7.51 (m, 11H), 7.27 (m, 2H) 643 215 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.87 (m, 11H), 7.69 to 7.51 (m, 10H), 7.27 (m, 2H) 643 216 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 4H), 7.97 to 7.87 (m, 10H), 7.71 to 7.51 (m, 11H), 7.35 to 7.27 (m, 4H) 719 217 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.83 (m, 14H), 7.69 to 7.51 (m, 11H), 7.35 to 7.27 (m, 4H) 719 218 8.38 (dd, 2H), 8.23 (d, 2H), 8.05 to 7.85 (m, 11H), 7.76 to 7.74 (m, 2H), 7.62 to 7.42 (m, 10H), 7.27 (m, 2H) 683 219 8.38 (dd, 2H), 8.23 (d, 2H), 7.99 to 7.87 (m, 13H), 7.76 (dd, 1H), 7.62 to 7.27 (m, 15H) 759 220 8.38 (dd, 2H), 8.23 (d, 2H), 7.97 to 7.87 (m, 14H), 7.62 to 7.51 (m, 8H), 7.35 to 7.27 (m, 4H) 694 221 8.38~8.34(m, 3H), 8.23(d, 2H), 7.97~7.80(m, 13H), 7.67~7.51(m, 10H), 7.27(m, 2H) 694 222 8.38 (dd, 4H), 8.17 to 8.12 (m, 2H), 7.97 to 7.87 (m, 6H), 7.77 (t, 1H), 7.62 to 7.51 (m, 12H), 7.27 (m, 2H) 593 223 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.97 to 7.87 (m, 8H), 7.77 (t, 1H), 7.62 to 7.51 (m, 14H), 7.35 (d, 2H), 7.27 ( m, 2H) 669 224 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 8.05 (m, 5H), 7.97 to 7.87 (m, 6H), 7.77 to 7.51 (m, 13H), 7.27 (m, 2H) 643 225 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 7.87 (m, 11H), 7.77 to 7.51 (m, 12H), 7.27 (m, 2H) 643 226 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 4H), 7.97 to 7.87 (m, 8H), 7.77 to 7.51 (m, 13H), 7.35 to 7.27 (m, 4H) 719 227 8.38 (dd, 2H), 8.17 to 7.61 (m, 27H), 7.35 to 7.27 (m, 4H) 719 228 8.38 (dd, 2H), 8.17 to 7.74 (m, 14H), 7.61 to 7.42 (m, 11H), 7.27 (m, 2H) 683 229 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.99 to 7.87 (m, 11H), 7.77 to 7.76 (m, 2H), 7.61 to 7.27 (m, 16H) 759 230 8.38 (dd, 2H), 8.17 to 8.12 (m, 2H), 7.97 to 7.87 (m, 12H), 7.77 (t, 1H), 7.61 to 7.51 (m, 9H), 7.35 to 7.27 (m, 4H) 694 231 8.38~8.34(m, 3H), 8.17~8.12(m, 2H), 7.97~7.77(m, 12H), 7.67~7.51(m, 11H), 7.27(m, 2H) 694 232 8.89 (s, 2H), 8.23 (dd, 2H), 7.97 to 7.87 (m, 10H), 7.62 to 7.51 (m, 8H), 7.27 (m, 2H) 516 233 8.89 (s, 2H), 8.23 to 8.17 (m, 3H), 7.97 to 7.87 (m, 6H), 7.77 (t, 1H), 7.63 to 7.51 (m, 10H), 7.27 (m, 2H) 516 234 8.89 (s, 4H), 8.23 (dd, 4H), 8.13 (d, 2H), 7.97 to 7.87 (m, 6H), 7.62 to 7.51 (m, 12H), 7.27 (m, 2H) 670 235 8.89 (s, 4H), 8.23 (dd, 4H), 7.97 to 7.87 (m, 10H), 7.76 (s, 3H), 7.62 to 7.51 (m, 11H), 7.27 (m, 2H) 746 236 8.89 (s, 4H), 8.23 to 8.17 (m, 5H), 7.97 to 7.87 (m, 6H), 7.77 to 7.76 (m, 4H), 7.62 to 7.51 (m, 12H), 7.36 (m, 1H), 7.27 (m, 2H) 746 237 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 5H), 7.62 to 7.51 (m, 18H), 7.35 to 7.29 (m, 3H) 669 238 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 8.05 (dd, 1H), 7.97 to 7.95 (m, 3H), 7.71 to 7.51 (m, 16H), 7.29 ( m, 1H) 643 239 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.95 (m, 7H), 7.69 to 7.51 (m, 15H), 7.29 (m, 1H) 643 240 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 7.97 to 7.95 (m, 5H), 7.71 to 7.51 (m, 16H), 7.35 to 7.29 (m, 3H) 719 241 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.95 (m, 9H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 16H), 7.35 to 7.29 (m, 3H) 719 242 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 8.05 to 7.95 (m, 5H), 7.85 (dd, 1H), 7.76 to 7.74 (m, 2H), 7.62 to 7.42 ( m, 15H), 7.29 (m, 1H) 683 243 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.91 (m, 8H), 7.76 (dd, 1H), 7.62 to 7.29 (m, 19H) 759 244 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.92 (m, 9H), 7.62 to 7.51 (m, 13H), 7.35 to 7.29 (m, 3H) 694 245 8.38~8.34(m, 3H), 8.23(d, 2H), 8.15(d, 1H), 7.97~7.92(m, 7H), 7.80(t, 1H), 7.67~7.51(m, 15H), 7.29( m, 1H) 694 246 8.38 (dd, 4H), 8.17 to 8.12 (m, 3H), 7.95 (d, 1H), 7.77 (t, 1H), 7.62 to 7.51 (m, 17H), 7.29 (m, 1H) 593 247 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.95 (d, 3H), 7.77 (t, 1H), 7.62 to 7.51 (m, 19H), 7.35 to 7.29 (m, 3H) 669 248 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 8.05 (m, 6H), 7.95 (d, 1H), 7.71 to 7.51 (m, 18H), 7.29 (m, 1H) 643 249 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 7.95 (m, 7H), 7.77 to 7.51 (m, 17H), 7.29 (m, 1H) 643 250 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 5H), 7.95 (d, 3H), 7.71 to 7.51 (m, 18H), 7.35 to 7.29 ( m, 3H) 719 251 8.38 (dd, 2H), 8.17 to 7.95 (m, 9H), 7.83 to 7.51 (m, 19H), 7.35 to 7.29 (m, 3H) 719 252 8.38 (dd, 2H), 8.17 to 7.95 (m, 6H), 7.85 to 7.74 (m, 4H), 7.62 to 7.42 (m, 16H), 7.29 (m, 1H) 683 253 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.99 to 7.91 (m, 6H), 7.77 to 7.76 (m, 2H), 7.62 to 7.29 (m, 20H) 759 254 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.95 to 7.92 (m, 7H), 7.77 (t, 1H), 7.62 to 7.51 (m, 14H), 7.35 to 7.29 (m, 3H) 694 255 8.38~8.34(m, 3H), 8.17~8.12(m, 3H), 7.95~7.92(m, 5H), 7.80~7.77(m, 2H), 7.67~7.51(m, 16H), 7.29(m, 1H) ) 694 256 8.89 (s, 2H), 8.23 (dd, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.62 to 7.51 (m, 13H), 7.29 (m, 1H) 516 257 8.89 (s, 2H), 8.23 to 8.15 (m, 4H), 7.95 (d, 1H), 7.77 (t, 1H), 7.62 to 7.51 (m, 15H), 7.29 (m, 1H) 516 258 8.89 (s, 4H), 8.23 (dd, 4H), 8.15 to 8.13 (m, 3H), 7.95 (d, 1H), 7.62 to 7.51 (m, 17H), 7.29 (m, 1H) 670 259 8.89 (s, 4H), 8.23 (dd, 4H), 8.15 (d, 1H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.76 (s, 3H), 7.62 to 7.51 (m, 16H), 7.29 (m, 1H) 746 260 8.89 (s, 4H), 8.23 to 8.15 (m, 6H), 7.95 (d, 1H), 7.77 to 7.76 (m, 4H), 7.62 to 7.51 (m, 17H), 7.36 to 7.29 (m, 2H) 746 261 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 7.97 to 7.95 (m, 5H), 7.71 to 7.51 (m, 16H), 7.35 to 7.29 (m, 3H) 719 262 8.65 (m, 2H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 7H), 8.05 to 7.95 (m, 4H), 7.71 to 7.51 (m, 14H), 7.29 ( m, 1H) 693 263 9.19 (t, 1H), 8.65 to 8.52 (m, 3H), 8.38 (dd, 2H), 8.23 to 7.95 (m, 11H), 7.71 to 7.51 (m, 13H), 7.29 (m, 1H) 693 264 8.65 (m, 2H), 8.52 (dd, 2H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 7H), 7.97 to 7.95 (m, 5H), 7.71 to 7.51 (m, 14H), 7.35 to 7.29 (m, 3H) 769 265 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 7.95 (m, 13H), 7.83 (dd, 1H), 7.71 to 7.51 (m, 14H), 7.35 to 7.29 ( m, 3H) 769 266 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 8.05 to 7.95 (m, 5H), 7.85 (dd, 1H), 7.76 to 7.42 ( m, 15H), 7.29 (m, 1H) 733 267 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 7.99 to 7.91 (m, 8H), 7.76 to 7.29 (m, 18H) 809 268 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 7.97 to 7.92 (m, 9H), 7.71 to 7.51 (m, 11H), 7.35 to 7.29 (m, 3H) 744 269 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 to 8.34 (m, 3H), 8.23 to 8.14 (m, 5H), 7.97 to 7.92 (m, 7H), 7.80 (t, 1H), 7.71 to 7.51 (m, 13H), 7.29 (m, 1H) 744 270 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 4H), 8.18 to 8.12 (m, 5H), 7.95 (d, 1H), 7.71 to 7.51 (m, 16H), 7.29 (m, 1H) 643 271 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 5H), 7.95 (d, 3H), 7.77 to 7.51 (m, 18H), 7.35 to 7.29 ( m, 3H) 719 272 8.65 (m, 2H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 8H), 7.95 (d, 1H), 7.77 to 7.51 (m, 16H), 7.29 (m, 1H) 693 273 9.19 (t, 1H), 8.65 to 8.52 (m, 3H), 8.38 (dd, 2H), 8.18 to 7.95 (m, 9H), 7.77 to 7.51 (m, 15H), 7.29 (m, 1H) 693 274 8.65 (m, 2H), 8.52 (dd, 2H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 7H), 7.95 (d, 3H), 7.77 to 7.51 (m, 16H), 7.35 to 7.29 ( m, 3H) 769 275 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 7.95 (m, 11H), 7.77 to 7.51 (m, 17H), 7.35 to 7.29 (m, 3H) 769 276 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 7.95 (m, 8H), 7.85 to 7.42 (m, 18H), 7.29 (m, 1H) 733 277 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 5H), 7.99 to 7.91 (m, 6H), 7.77 to 7.29 (m, 20H) 809 278 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 5H), 7.95 to 7.92 (m, 7H), 7.77 to 7.51 (m, 13H), 7.35 to 7.29 (m, 3H) 744 279 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 to 8.34 (m, 3H), 8.18 to 8.12 (m, 5H), 7.95 to 7.92 (m, 5H), 7.77 to 7.51 (m, 16H), 7.29 (m, 1H) 744 280 8.89 (s, 2H), 8.65 (m, 1H), 8.52 (dd, 1H), 8.23 to 8.14 (m, 5H), 7.97 to 7.87 (m, 5H), 7.71 to 7.51 (m, 11H), 7.29 ( m, 1H) 566 281 8.89 (s, 2H), 8.65 (m, 1H), 8.52 (dd, 1H), 8.23 to 8.14 (m, 6H), 7.95 (d, 1H), 7.77 to 7.51 (m, 14H), 7.29 (m, 1H) 566 282 8.89 (s, 4H), 8.65 (m, 1H), 8.52 (dd, 1H), 8.23 to 8.14 (m, 9H), 7.95 (d, 1H), 7.71 to 7.51 (m, 15H), 7.29 (m, 1H) 720 283 8.89 (s, 4H), 8.65 (m, 1H), 8.52 (dd, 1H), 8.23 to 8.14 (m, 7H), 7.97 to 7.87 (m, 5H), 7.76 to 7.51 (m, 17H), 7.29 ( m, 1H) 796 284 8.89 (s, 4H), 8.65 (m, 1H), 8.52 (dd, 1H), 8.23 to 8.14 (m, 8H), 7.95 (d, 1H), 7.77 to 7.51 (m, 19H), 7.36 to 7.29 ( m, 2H) 796 285 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.95 (m, 9H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 16H), 7.35 to 7.29 (m, 3H) 719 286 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 7.95 (m, 12H), 7.83 (dd, 1H), 7.71 to 7.51 (m, 14H), 7.29 (m, 1H) 693 287 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.95 (m, 10H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 13H), 7.29 (m, 1H) 693 288 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 7.95 (m, 13H), 7.83 (dd, 1H), 7.71 to 7.51 (m, 14H), 7.35 to 7.29 ( m, 3H) 769 289 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.95 (m, 12H), 7.83 (dd, 2H), 7.69 to 7.51 (m, 14H), 7.35 to 7.29 (m, 3H) 769 290 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.95 (m, 9H), 7.76 to 7.42 (m, 17H), 7.29 (m, 1H) 733 291 8.38 (dd, 2H), 8.23 (d, 2H), 8.10 to 7.91 (m, 12H), 7.83 to 7.29 (m, 19H) 809 292 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 7.92 (m, 13H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 11H), 7.35 to 7.29 (m, 3H) 744 293 8.38~8.34(m, 3H), 8.23(d, 2H), 8.15~7.92(m, 11H), 7.83~7.80(m, 2H), 7.69~7.51(m, 13H), 7.29(m, 1H) 744 294 8.38 (dd, 4H), 8.17 to 7.95 (m, 7H), 7.83 to 7.51 (m, 17H), 7.29 (m, 1H) 643 295 8.38 (dd, 2H), 8.17 to 7.95 (m, 9H), 7.83 to 7.51 (m, 19H), 7.35 to 7.29 (m, 3H) 719 296 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 7.95 (m, 10H), 7.83 to 7.51 (m, 17H), 7.29 (m, 1H) 693 297 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 7.95 (m, 10H), 7.83 to 7.51 (m, 16H), 7.29 (m, 1H) 693 298 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 7.95 (m, 11H), 7.83 to 7.51 (m, 17H), 7.35 to 7.29 (m, 3H) 769 299 8.38 (dd, 2H), 8.17 to 7.95 (m, 12H), 7.83 to 7.51 (m, 18H), 7.35 to 7.29 (m, 3H) 769 300 8.38 (dd, 2H), 8.17 to 7.95 (m, 9H), 7.85 to 7.42 (m, 19H), 7.29 (m, 1H) 733 301 8.38 (dd, 2H), 8.17 to 7.91 (m, 12H), 7.83 to 7.29 (m, 21H) 809 302 8.38 (dd, 2H), 8.17 to 7.92 (m, 13H), 7.83 to 7.51 (m, 14H), 7.35 to 7.29 (m, 3H) 744 303 8.38~8.24(m, 3H), 8.17~7.92(m, 11H), 7.83~7.51(m, 17H), 7.29(m, 1H) 744 304 8.89 (s, 2H), 8.23 to 7.95 (m, 12H), 7.69 to 7.51 (m, 11H), 7.29 (m, 1H) 566 305 8.89 (s, 2H), 8.23 to 7.95 (m, 8H), 7.83 to 7.51 (m, 15H), 7.29 (m, 1H) 566 306 8.89 (s, 4H), 8.23 to 7.95 (m, 11H), 7.83 (dd, 1H), 7.69 to 7.51 (m, 15H), 7.29 (m, 1H) 720 307 8.89 (s, 4H), 8.23 (dd, 2H), 8.15 to 7.51 (m, 29H), 7.29 (m, 1H) 796 308 8.89 (s, 4H), 8.23 to 7.95 (m, 10H), 7.83 to 7.51 (m, 20H), 7.36 to 7.29 (m, 2H) 796 309 8.38 (dd, 4H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 5H), 7.87 (d, 2H), 7.62 to 7.51 (m, 17H) 669 310 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 7H), 7.87 (d, 2H), 7.62 to 7.51 (m, 19H), 7.35 (d, 2H) 745 311 8.65 (m, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 8.05 (dd, 1H), 7.97 to 7.95 (m, 5H), 7.87 (d, 2H), 7.71 to 7.51 ( m, 17H) 719 312 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 8.10 (m, 3H), 8.02 to 7.95 (m, 6H), 7.87 (d, 2H), 7.69~7.51(m, 16H) 719 313 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.23 to 8.14 (m, 5H), 7.97 to 7.95 (m, 7H), 7.87 (d, 2H), 7.71 to 7.51 ( m, 17H), 7.35 (d, 2H) 795 314 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 to 8.10 (m, 3H), 8.02 to 7.95 (m, 8H), 7.87 to 7.83 (m, 3H), 7.69 to 7.51 (m, 17H), 7.35 (d, 2H) 795 315 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.95 (m, 7H), 7.87 to 7.85 (m, 3H), 7.76 to 7.74 (m, 2H), 7.62 to 7.41 (m, 16H) 759 316 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.99 to 7.87 (m, 12H), 7.76 (dd, 1H), 7.62 to 7.42 (m, 19H) 835 317 8.38 (dd, 2H), 8.23 (d, 2H), 8.15 (d, 1H), 7.97 to 7.87 (m, 13H), 7.62 to 7.51 (m, 14H), 7.35 (d, 2H) 770 318 8.38~8.34(m, 3H), 8.23(d, 2H), 8.15(d, 1H), 7.97~7.87(m, 11H), 7.80(t, 1H), 7.67~7.51(m, 16H) 770 319 8.38 (dd, 4H), 8.15 to 8.12 (m, 3H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.77 (t, 1H), 7.62 to 7.51 (m, 18H) 669 320 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.97 to 7.95 (m, 5H), 7.87 (d, 2H), 7.77 (t, 1H), 7.62 to 7.51 (m, 20H), 7.35 ( d, 2H) 745 321 8.65 (m, 1H), 8.38 (dd, 2H), 8.18 to 8.05 (m, 6H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.7 to 7.51 (m, 19H) 719 322 9.19 (t, 1H), 8.59 (dd, 1H), 8.38 (dd, 2H), 8.17 to 8.10 (m, 5H), 8.02 to 7.95 (m, 4H), 7.87 (d, 2H), 7.77 to 7.51 ( m, 18H) 719 323 8.65 (m, 1H), 8.52 (dd, 1H), 8.38 (dd, 2H), 8.18 to 8.12 (m, 5H), 7.95 (d, 3H), 7.77 to 7.51 (m, 18H), 7.35 to 7.29 ( m, 3H) 719 324 8.38 (dd, 2H), 8.17 to 8.10 (m, 5H), 8.02 to 7.95 (m, 6H), 7.87 to 7.51 (m, 22H), 7.35 (d, 2H) 795 325 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 8.05 to 7.95 (m, 5H), 7.87 to 7.85 (m, 3H), 7.77 to 7.74 (m, 3H), 7.62 to 7.42 (m, 17H) ) 759 326 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.99 to 7.87 (m, 10H), 7.77 to 7.76 (m, 2H), 7.62 to 7.35 (m, 20H) 835 327 8.38 (dd, 2H), 8.17 to 8.12 (m, 3H), 7.97 to 7.87 (m, 11H), 7.77 (t, 1H), 7.62 to 7.51 (m, 15H), 7.35 (d, 2H) 770 328 8.38~8.34(m, 3H), 8.17~8.12(m, 3H), 7.97~7.87(m, 9H), 7.80~7.77(m, 2H), 7.67~7.51(m, 17H) 770 329 8.89 (s, 2H), 8.23 (dd, 2H), 8.15 (d, 1H), 7.97 to 7.95 (m, 5H), 7.87 (d, 4H), 7.62 to 7.51 (m, 14H) 592 330 8.89 (s, 2H), 8.23 to 8.15 (m, 4H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.77 (t, 1H), 7.63 to 7.51 (m, 16H) 592 331 8.89 (s, 4H), 8.23 (dd, 4H), 8.15 to 8.13 (m, 3H), 7.97 to 7.95 (m, 3H), 7.87 (d, 2H), 7.62 to 7.51 (m, 18H) 746 332 8.89 (s, 4H), 8.23 (dd, 4H), 8.15 (d, 1H), 7.97 to 7.95 (m, 5H), 7.87 (d, 4H), 7.76 (s, 3H), 7.62 to 7.51 (m, 17H) 822 333 8.89 (s, 4H), 7.23 to 7.15 (m, 6H), 7.95 (d, 1H), 7.77 to 7.76 (m, 4H), 7.62 to 7.51 (m, 17H), 7.36 to 7.29 (m, 2H) 746 334 8.33 (s, 1H), 7.97 to 7.87 (m, 12H), 7.61 to 7.51 (m, 10H), 7.35 to 7.27 (m, 5H) 592 335 8.40 to 8.38 (m, 5H), 7.97 to 7.87 (m, 10H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 (m, 3H) 592 336 8.38 (dd, 4H), 7.97 to 7.87 (m, 8H), 7.61 to 7.51 (m, 10H), 7.35 to 7.27 (m, 5H) 593 337 8.38 (dd, 2H), 7.97 to 7.87 (m, 10H), 7.62 to 7.51 (m, 12H), 7.35 to 7.27 (m, 7H) 669 338 8.38 (dd, 4H), 8.13 (d, 2H), 7.89 (m, 2H), 7.61 to 7.51 (m, 16H), 7.29 to 7.27 (m, 3H) 593 339 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.38 (dd, 2H), 7.97 to 7.87 (m, 8H), 7.67 to 7.51 (m, 8H), 7.35 to 7.27 ( m, 5H) 594 340 8.91 (d, 2H), 8.38 (dd, 4H), 8.09 (d, 1H), 7.98 to 7.89 (m, 4H), 7.72 (d, 1H), 7.61 to 7.51 (m, 10H), 7.29 to 7.27 ( m, 3H), 6.92 (dd, 1H) 594 341 8.34~8.33(m, 2H), 8.17(t, 1H), 7.89(m, 6H), 7.80~7.77(m, 2H), 7.67~7.51(m, 13H), 7.36~7.27(m, 4H) 592 342 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.39 to 8.34 (m, 2H), 8.17 (t, 1H), 7.89 (m, 4H), 7.80 to 7.51 (m, 13H), 7.36~7.27(m, 4H) 593 343 8.38~8.34(m, 5H), 8.17(t, 1H), 7.89(m, 2H), 7.80~7.77(m, 2H), 7.67~7.51(m, 13H), 7.36~7.27(m, 4H) 593 344 8.38~8.34(m, 3H), 8.17(t, 1H), 7.95~7.89(m, 4H), 7.80~7.77(m, 2H), 7.67~7.51(m, 15H), 7.36~7.27(m, 6H) ) 669 345 9.34 (d, 1H), 8.80 (dd, 1H), 8.52 (m, 1H), 8.38 to 8.34 (m, 3H), 8.17 (t, 1H), 7.95 to 7.89 (m, 4H), 7.80 to 7.51 ( m, 13H), 7.36 to 7.27 (m, 6H) 670

Comparative Example compound

<Formula b>

<Formula c>

<Formula d>

<BCP>

<Alq3>

<2-TNATA>

<α-NPD>

Comparative Example 1

* Compound c represented by Formula c is used as a fluorescent blue host, Compound d represented by Formula d is used as a fluorescent blue dopant, and 2-TNATA (4,4',4”-tris(N- naphthalen-2-yl)-N-phenylamino)-triphenylamine) was used as the hole injection layer material, and the α-NPD (N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine) was An organic electroluminescent device having the following structure was prepared using the hole transport layer material: ITO/2-TNATA (60 nm)/ (30 nm)/ Compound c + Compound d (30 nm)/Alq ₃ (25 nm) )/Liq (1 nm)/Al (100 nm).

For the anode, a 15Ω/cm ² (1000Å) ITO glass substrate from Corning was cut into a size of 25 mm x 25 mm x 0.7 mm and ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, followed by 30 minutes. It was used after washing with UV ozone. A hole injection layer having a thickness of 60 nm was formed by vacuum deposition of 2-TNATA on the substrate. On the hole injection layer, α-NPD was vacuum-deposited to form a hole transport layer with a thickness of 30 nm. A compound represented by Formula c and a compound represented by Formula d (doping rate: 4wt%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, the Alq ₃ compound was vacuum-deposited to a thickness of 25 nm on the light emitting layer to form an electron transport layer. 1 nm of Liq (electron injection layer) and 100 nm of Al (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic electroluminescent device as shown in Table 3. This is referred to as Comparative Example 1.

Comparative Example 2

In Comparative Example 1, by using the compound b instead of Alq3 for the electron transport layer, an organic electroluminescent device having the following structure was prepared: ITO/2-TNATA (60 nm)/α-NPD (30 nm)/ Compound c + Compound d (30 nm)/Comparative compound b (25 nm)/Liq (1 nm)/Al (100 nm). This is referred to as Comparative Example 2.

Comparative Example 3

An organic electroluminescent device was prepared in the same manner as in Comparative Example 1, except that the electron transport layer was used as the compound Alq3 and the BCP 5 nm was deposited as the hole blocking layer compound. This is referred to as Comparative Example 3.

Examples 1 to 8

Compound 21, 39, 54, 76, 147, 166, 243 or 340 synthesized as shown in Table 1 instead of Alq3 used as the electron transport layer was subjected to sublimation purification process as shown in Table 3 Except that each was used as the electron transport layer prepared an organic electroluminescent device in the same manner as in Comparative Example 1. These are referred to as Examples 1 to 8, respectively.

Examples 9-11

The organic electric field in the same manner as in Comparative Example 3, except that the compound BCP used as the hole blocking layer was used as the hole blocking layer as shown in Table 3 through the sublimation purification process of the compound 121, 207 or 341 disclosed in Table 1 above. A light emitting device was manufactured. These are referred to as Examples 9 to 11, respectively.

Example 12

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 3, except that Compound 21 disclosed in Table 1 was used instead of Compound BCP used as a hole blocking layer, and Compound 21 was used instead of Alq3 as an electron transport layer as a hole blocking layer. did. This is referred to as Example 12.

Evaluation Example 1: Evaluation of luminescence characteristics and lifetime of Comparative Examples 1 to 3 and Examples 1 to 12

For Comparative Examples 1 to 3 and Examples 1 to 12, the luminous peak and luminous efficiency were evaluated using Keithley sourcemeter “2400” and KONIKA MINOLTA “CS-2000”,

The time (LT98) for the luminance (L) to reach 98% based on _{the initial luminance (L 0} ) 1000 nit was measured using the M6000S life measuring device of McScience, and the results are shown in Table 3 and Figures 1 to 2 is shown.

sample No. hole blocking
compound
No. electronic transport
compound
No. Voltage
OP. V efficiency
[cd/A] luminescence peak
[nm] life span
[LT98] Comparative Example 1 - Alq3 5.53 4.90 459 30.3 Comparative Example 2 - b 5.67 4.62 456 17.1 Example 1 - 21 4.55 6.01 457 93.4 Example 2 - 39 5.10 5.51 455 53.4 Example 3 - 54 5.30 5.47 460 51.1 Example 4 - 76 5.27 5.58 455 55.0 Example 5 - 147 5.23 5.60 460 55.7 Example 6 - 166 5.36 5.32 461 48.0 Example 7 - 243 5.22 5.63 461 57.3 Example 8 - 340 5.19 5.68 458 60.9 Comparative Example 3 BCP Alq3 5.40 5.22 459 45.7 Example 9 121 Alq3 4.65 5.95 458 88.0 Example 10 207 Alq3 4.96 5.79 456 69.1 Example 11 341 Alq3 4.90 5.85 460 75.6 Example 12 121 21 4.41 6.90 459 128.7

As shown in Table 3, Examples 1 to 12 exhibited lower voltage driving and improved light emission characteristics compared to Comparative Examples 1 to 3. In addition, even when the hole blocking layer was included, low voltage driving and improved light emitting characteristics and lifespan characteristics were exhibited.

1 is a lifespan characteristic evaluation graph showing the measurement results of the organic electroluminescent devices prepared in Examples 1 to 8 and Comparative Examples 1 to 2;

2 is a lifespan characteristic evaluation graph showing measurement results for the organic electroluminescent devices prepared in Examples 9 to 12 and Comparative Examples 1 and 3;

As shown in Table 3, Examples 1 to 12 exhibited improved lifespan characteristics compared to Comparative Examples 1 to 3. In particular, the benzoimidazolone derivatives improved the electron transport ability in combination with the nitrogen-containing aryl group, so that the organic light emitting compounds exhibited excellent performance and lifespan.

Although preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present. It belongs to the scope of the invention.

Claims (10)

delete delete delete delete delete 1, 3, 4, 5, 11 to 14, 16, 17, 19, 29 to 33, 36, 37, 40, 41, 47 to 50, 55 to 75, 77 to 79, 82 to 88, 92, 93 , 95, 96, 101-118, 120, 122-124, 126-131, 135, 136, 138, 139, 141-170, 176-179, 186-189, 195-198, 204-212, 218-221 , 228 to 236, 242 to 245, 252 to 260, 266 to 269, 276 to 284, 290 to 293, 300 to 308, 315 to 318, 325 to 335, 339 to 342, or 345. A benzoimidazolone derivative organic light emitting compound.

7. The method of claim 6,
The benzoimidazolone derivative organic light emitting compound is a benzoimidazolone derivative organic light emitting compound, characterized in that it is used as a material for a light emitting layer, a hole blocking layer, an electron transport layer or an electron injection layer among organic electroluminescent devices. An organic electroluminescent device in which at least one organic thin film layer is sandwiched between a cathode and an anode, wherein the organic thin film layer has a multilayer structure including at least one light emitting layer and an electron transport region, and at least one layer in the organic thin film layer is An organic electroluminescent device comprising the benzoimidazolone derivative organic light emitting compound according to claim 6 alone or in a mixture of two or more. 9. The method of claim 8,
At least one layer selected from the organic thin film layer formed between the cathode and the anode is an organic electroluminescent device, characterized in that formed by a vacuum deposition process or a solution process. 9. The method of claim 8,
The organic electroluminescent device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; devices for flexible lighting of monochromatic or white color; An organic electroluminescent device, characterized in that it is used in any one device selected from the group consisting of.

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