TW202024300A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

Description

Heterocyclic compound and organic light emitting device containing the same

The present invention relates to a heterocyclic compound and an organic light-emitting device including it.

The electroluminescent device is an automatic light-emitting display device and has advantages such as wide viewing angles, fast response speed, and excellent contrast.

The organic light-emitting device has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from two electrodes are combined and paired in the organic thin film, and emit light when the electrons and holes are annihilated. A single-layer or multilayer organic film can be formed as needed.

If necessary, the material of the organic film can have a light-emitting function. For example, a compound capable of forming a light-emitting layer by itself can be used as the material of the organic thin film, or a compound capable of being a host or dopant of a host-dopant-based light-emitting layer can also be used. In addition, compounds capable of hole injection, hole transfer, electron blocking, hole blocking, electron transfer, electron injection, and the like can also be used as the material of the organic thin film.

The development of organic thin-film materials continues to require improvement in the performance, lifetime or efficiency of organic light-emitting devices.

[Prior Technical Document]

[Patent Document]

U.S. Patent No. 4,356,429

[ technical problem ]

The present invention relates to providing a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

[ Technical solutions ]

在化學式1中， X為O或S， L₁ 及L₂ 為經取代或未經取代之伸芳基；或經取代或未經取代之伸雜芳基， Z₂ 為氫；經取代或未經取代之烷基；經取代或未經取代之芳基；經取代或未經取代之雜芳基；-SiRR’R”；或-P(=O)RR’， X₁ 至X₃ 彼此相同或不同，且各自獨立地為N；CR₃ ；或P， R₁ 及R₂ 彼此相同或不同，且各自獨立地為氫；氘；經取代或未經取代之烷基；經取代或未經取代之芳基；經取代或未經取代之雜芳基；或P(=O)RR’， R₃ 為氫；鹵素基；經取代或未經取代之烷基；經取代或未經取代之芳基；經取代或未經取代之雜芳基；或P(=O)RR’， R_a 及R_b 彼此相同或不同，且各自獨立地為氫；氘；鹵素基；-CN；經取代或未經取代之烷基；經取代或未經取代之烯基；經取代或未經取代之炔基；經取代或未經取代之烷氧基；經取代或未經取代之環烷基；經取代或未經取代之雜環烷基；經取代或未經取代之芳基；經取代或未經取代之雜芳基；-SiRR’R”；-P(=O)RR’；以及未經取代或被經取代或未經取代之烷基、經取代或未經取代之芳基、或者經取代或未經取代之雜芳基取代的胺基，或彼此相鄰的兩個或更多個基團彼此鍵結形成經取代或未經取代之脂族或芳族烴環， R、R’及R”彼此相同或不同，且各自獨立地為氫；氘；-CN；經取代或未經取代之烷基；經取代或未經取代之環烷基；經取代或未經取代之芳基；或經取代或未經取代之雜芳基， m為0至4的整數， p及n為0至3的整數， q為0至3的整數， s為1至4的整數，且 當q為0的整數且Z₂ 為氫時，n為2或3的整數，且R_b 為經取代或未經取代之芳基；或經取代或未經取代之雜芳基，或彼此相鄰的兩個或更多個基團彼此鍵結以形成經取代或未經取代之脂族或芳族烴環。An example of this application provides a heterocyclic compound represented by the following Chemical Formula 1. [Chemical formula 1]

In chemical formula 1, X is O or S, L ₁ and L ₂ are substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroaryl groups, Z ₂ is hydrogen; substituted or unsubstituted Substituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R"; or -P(=O)RR', X ₁ to X ₃ are the same as each other Or different and each independently N; CR ₃ ; or P, R ₁ and R ₂ are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted Substituted aryl; substituted or unsubstituted heteroaryl; or P(=O)RR', R ₃ is hydrogen; halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted Aryl; substituted or unsubstituted heteroaryl; or P(=O)RR', R _a and R _b are the same or different from each other, and are each independently hydrogen; deuterium; halogen; -CN; substituted Or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; Substituted or unsubstituted heterocycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R";-P(=O)RR'; and unsubstituted A substituted or substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group substituted amine group, or two or more adjacent to each other The two groups are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, R, R'and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted Substituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, m is an integer from 0 to 4, p and n Is an integer of 0 to 3, q is an integer of 0 to 3, s is an integer of 1 to 4, and when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2 or 3, and R _b is A substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic group Group hydrocarbon ring.

Another embodiment of the present application provides an organic light-emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on the first electrode Between the second electrode and the second electrode, one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[ Beneficial effect ]

The compound described in the present invention can be used as an organic material layer material of an organic light emitting device. The compound can function as a hole injection material, a hole transfer material, a light emitting material, an electron transfer material, an electron injection material, and the like in an organic light emitting device. In particular, the heterocyclic compound represented by Chemical Formula 1 can be used as an electron transfer layer material, a hole blocking layer material, or a charge generation layer material of an organic light-emitting device. In addition, when the compound represented by Chemical Formula 1 is used in the organic material layer, the driving voltage is reduced and the light efficiency in the device is improved, and the device life characteristics can be improved by the thermal stability of the compound.

In addition, the compound of Chemical Formula 1 is a bipolar compound having both P-type and N-type substituents in the core structure, and when later used as an organic material layer of an organic light-emitting device, it can block hole leakage and effectively excitons Ground is trapped in the light-emitting layer. In addition, in a specific device structure, the hole properties are enhanced, and the electron mobility changes relatively slowly, which balances the electrons and holes in the light-emitting layer, thereby appropriately forming the exciton recombination region, thus increasing the efficiency and lifetime .

Hereinafter, this application will be described in detail.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound becomes another substituent, and the substitution position is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In the present invention, halogen may be fluorine, chlorine, bromine or iodine.

In the present invention, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, second butyl, 1-methyl-butyl , 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4- Methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl Base, n-octyl, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- Propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but not limited thereto.

In the present invention, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2 ,2-Diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)ethylene -1-yl, stilbene, styryl and similar groups, but not limited thereto.

In the present invention, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group can be 2 to 60, specifically 2 to 40 and more specifically 2 to 20.

In the present invention, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1-20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, third butoxy, second butoxy, n-pentoxy, Neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyl An oxy group, a p-methylbenzyloxy group and the like, but not limited thereto.

In the present invention, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another cyclic group. Here, other cyclic groups may be cycloalkyl groups, but may also be different types of cyclic groups such as heterocycloalkyl groups, aryl groups, and heteroaryl groups. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40 and more specifically 5 to 20. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methyl Cyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups, but not limited to these .

In the present invention, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or fused with other cyclic groups. Here, other cyclic groups may be heterocycloalkyl groups, but may also be different types of cyclic groups, such as cycloalkyl groups, aryl groups, and heteroaryl groups. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40 and more specifically 3 to 20.

In the present invention, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the aryl group is directly connected to or fused with other cyclic groups. Here, other cyclic groups may be aryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include spirocyclic groups. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40 and more specifically 6 to 25. Specific examples of aryl groups may include phenyl, biphenyl, triphenyl, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylene group ( perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, pentaphenyl (Pentacenyl group), fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro -1H-indenyl, its fused ring and similar groups, but not limited thereto.

In the present invention, the silyl group is a substituent containing Si, has a Si atom directly connected as a group, and is represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ . R ₁₀₄ to R ₁₀₆ are the same or different from each other, and may each independently be a substituent formed by at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and Heterocyclic group. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl , Diphenylsilyl, phenylsilyl and the like, but not limited to these.

In the present invention, the stilbene group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

、

、

、

、

、

以及類似者。然而，所述結構不限於此。When the tungsten group is substituted, it can include

,

,

,

,

,

And the like. However, the structure is not limited to this.

In the present invention, the heteroaryl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which the heteroaryl group is directly connected to or fused with other cyclic groups. Here, other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and aryl groups. The number of carbon atoms of the heteroaryl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups can include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group , Imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazole Triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, piperan Group (pyranyl group), thiopyranyl group (thiopyranyl group), diazinyl group (diazinyl group), oxazinyl group (oxazinyl group), thiazinyl group (thiazinyl group), dioxynyl group (dioxynyl group), three Triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group , Quinazolinyl (qninozolinyl group), naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group), triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzoxazolyl group Imidazole group (benzimidazolyl group), benzothiophene group (benzothiophene group), benzofuran group (benzofuran group), dibenzothiophene group (dibenzothiophene group), dibenzofuran group (dibenzofuran group), carbazolyl group, benzocarbazolyl group, Dibenzocarbazolyl group, phenazinyl, dibenzosilole group, spirobi(dibenzosilole) group )), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[ 2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-Dihydroacridinyl, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group ), benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilolinyl (5,10-dihydrobenzo[b ,e][1,4]azasilinyl), pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo [1,2-e] Indoline, 5,11-dihydroindeno[1,2-b]carbazolyl (5,11-dihydroindeno[1,2-b]carbazolyl group) and similar groups Group, but not limited to this.

In the present invention, the amine group can be selected from the following groups: monoalkylamino group; monoarylamino group; monoheteroarylamino group; -NH ₂ ; dialkylamino group; diarylamino group ; Diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and although the number of carbon atoms is not specifically limited, it is preferably 1 to 30 . Specific examples of amine groups may include methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamine group, biphenylamine group, dibiphenylamine group group), anthracenylamine group, 9-methyl-anthrylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group group), triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorenylamine group, phenyltriphenylenylamine group, Biphenyltriphenylenylamine group and similar groups, but not limited thereto.

In the present invention, an aryl group means an aryl group having two bonding sites, that is, a divalent group. Except for each being a divalent group, the description of the aryl group provided above can be applied here. In addition, the heteroaryl group means a heteroaryl group having two bonding sites, that is, a divalent group. Except for each being a divalent group, the description of heteroaryl groups provided above can be applied here.

In the present invention, specific examples of the phosphine oxide group may include diphenyl phosphine oxide, dinaphthyl phosphine oxide, and the like, but are not limited thereto.

In the present invention, the "adjacent" group may mean a substituent that replaces the atom directly connected to the atom substituted by the corresponding substituent, the substituent whose steric position is closest to the corresponding substituent, or the substituent substituted by the corresponding substituent Another substituent of the atom. For example, two substituents substituted for the ortho position in the benzene ring and two substituents substituted for the same carbon in the aliphatic ring can be interpreted as groups "adjacent" to each other.

In the present invention, the term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the substitution position is not limited, as long as it is the position where the hydrogen atom is substituted, that is, the substituent may be The position of substitution, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In the present invention, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: C1-C60 linear or branched chain alkyl; C2 to C60 linear Or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic Aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and The C2 to C60 monocyclic or polycyclic heteroarylamine is either unsubstituted, or substituted with a substituent connecting two or more substituents selected from the above-mentioned substituents, or unsubstituted.

An example of this application provides a compound represented by Chemical Formula 1.

In an embodiment of the present application, X in Chemical Formula 1 may be O or S.

In an embodiment of the present application, X in Chemical Formula 1 may be O.

In an embodiment of the present application, X in Chemical Formula 1 may be S.

In an embodiment of the present application, X ₁ to X _{3 of} Chemical Formula 1 are the same as or different from each other, and may each independently be N; CR ₃ ; or P.

In another embodiment, X ₁ to X _{3 of} Chemical Formula 1 are the same or different from each other, and may each independently be N; or CR ₃ .

In an embodiment of the present application, X ₁ to X _{3 of} Chemical Formula 1 may be N.

In an embodiment of the present application, one of X ₁ to X ₃ of Chemical Formula 1 is N, and the rest may be CR ₃ .

In an embodiment of the present application, two of X ₁ to X ₃ of Chemical Formula 1 are N, and the rest may be CR ₃ .

In an embodiment of the present application, X ₁ to X _{3 of} Chemical Formula 1 may be CR ₃ .

In one embodiment of the present application, R ₃ may be hydrogen; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; Or P(=O)RR'.

In another embodiment, R ₃ can be hydrogen; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or P(=0)RR'.

In another embodiment, R ₃ can be hydrogen; C6 to C60 aryl; C2 to C60 heteroaryl; or P(=0)RR'.

In another embodiment, R ₃ can be hydrogen; or P(=0)RR'.

In an embodiment of the present application, _Ra and R _{b of} Chemical Formula 1 are the same or different from each other, and can be independently selected from the following groups: hydrogen; deuterium; halogen; -CN; substituted or Unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; Substituted or unsubstituted heterocycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R";-P(=O)RR'; and unsubstituted Substituted or substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl substituted amine group, or two or more adjacent to each other The groups can be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R _a and R _{b of} Chemical Formula 1 are the same or different from each other, and can be independently selected from the group consisting of: hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted A substituted aryl group; and a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, R _a and R _{b of} Chemical Formula 1 are the same or different from each other, and each can be independently selected from the group consisting of: hydrogen; substituted or unsubstituted C6 to C60 aryl groups; and The substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another embodiment, R _a and R _{b of} Chemical Formula 1 are the same or different from each other, and can be independently selected from the following group consisting of: hydrogen; C6 to C40 aryl; and C2 to C60 heteroaryl, Or two or more groups adjacent to each other may be bonded to each other to form a C3 to C60 aromatic hydrocarbon ring.

In another embodiment, the chemical formula R _a 1 may be hydrogen.

In an embodiment of the present application, R ₁ and R _{2 of} Chemical Formula 1 are the same or different from each other, and can each independently be hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted Aryl; substituted or unsubstituted heteroaryl; or P(=0)RR'.

In another embodiment, R ₁ and R _{2 of} Chemical Formula 1 are the same or different from each other, and can be each independently hydrogen; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or P(=O)RR'.

In another embodiment, R ₁ and R _{2 of} Formula 1 are the same or different from each other, and can be each independently hydrogen; substituted or unsubstituted C6 to C40 aryl groups; substituted or unsubstituted C2 to C40 heteroaryl; or P(=O)RR'.

In another embodiment, R ₁ and R _{2 of} Formula 1 are the same or different from each other, and can each independently be hydrogen; unsubstituted or grouped by a C1 to C40 alkyl group and a C2 to C40 heteroaryl group C6 to C40 aryl groups substituted by one or more substituents selected from among them; C2 to C40 N-containing heteroaryl groups; or P(=O)RR'.

In another embodiment, R ₁ and R _{2 of} Chemical Formula 1 are the same or different from each other, and can each independently be hydrogen; unsubstituted or substituted with carbazolyl, dibenzofuranyl or dibenzothienyl Phenyl; biphenyl; unsubstituted or substituted with methyl; carbazolyl; -P(=O)RR' or pyridyl.

In an embodiment of the present application, L ₁ and L _{2 of} Chemical Formula 1 may be substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroaryl groups.

In another embodiment, L ₁ and L _{2 of} Chemical Formula 1 may be substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

In another embodiment, L ₁ and L _{2 of} Chemical Formula 1 may be substituted or unsubstituted C6 to C40 arylene groups; or substituted or unsubstituted C2 to C40 heteroaryl groups.

In another embodiment, L ₁ and L _{2 of} Chemical Formula 1 may be C6 to C40 arylene groups; or C2 to C40 heteroarylene groups.

In another embodiment, L ₁ and L _{2 of} Chemical Formula 1 may be C6 to C30 arylene groups; or C2 to C30 heteroarylene groups.

In another embodiment, L ₁ and L _{2 of} Chemical Formula 1 may be phenylene; biphenylene; naphthylene; phenanthryl; triphenylene; divalent dibenzofuranyl; divalent Phenolinyl or divalent dibenzothienyl.

In an embodiment of the present application, L _{1 of} Chemical Formula ₁ may be a substituted or unsubstituted arylene group.

In another embodiment, L _{1 of} Chemical Formula 1 may be a substituted or unsubstituted C6 to C60 arylene group.

In another embodiment, L _{1 of} Chemical Formula 1 may be a substituted or unsubstituted C6 to C40 arylene group.

In another embodiment, L _{1 of} Chemical Formula ₁ may be a C6 to C40 arylene group.

In another embodiment, L _{1 of} Chemical Formula ₁ may be phenylene; or biphenylene.

In an embodiment of the present application, L _{2 of} Chemical Formula 1 may be a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroaryl group.

In another embodiment, L _{2 of} Chemical Formula 1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, L _{2 of} Chemical Formula 1 may be a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, L _{2 of} Chemical Formula 1 may be a C6 to C40 arylene group; or a C2 to C40 heteroarylene group.

In another embodiment, L _{2 of} Chemical Formula 1 may be phenylene; naphthylene; phenanthrenyl; triphenylene; divalent dibenzofuranyl; or divalent dibenzothienyl.

In an embodiment of the present application, Z _{2 of} Chemical Formula 1 may be hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R"; or -P(=O)RR'.

In another embodiment, Z _{2 of} Chemical Formula 1 may be hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, Z _{2 of} Chemical Formula 1 may be hydrogen; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, Z _{2 of} Chemical Formula 1 may be hydrogen; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

In another embodiment, Z _{2 of} Chemical Formula 1 may be hydrogen; phenyl; naphthyl; phenanthryl; dibenzofuranyl; or dibenzothienyl.

In an embodiment of the present application, p of Chemical Formula 1 may be 0.

In an embodiment of the present application, p of Chemical Formula 1 may be 1.

In an embodiment of the present application, q of Chemical Formula 1 may be 0.

In an embodiment of the present application, q of Chemical Formula 1 may be 1.

In an embodiment of the present application, q of Chemical Formula 1 may be 2.

In an embodiment of the present application, s of Chemical Formula 1 may be 1.

In an embodiment of the present application, s of Chemical Formula 1 may be 2.

In an embodiment of the present application, s of Chemical Formula 1 may be 3.

In an embodiment of the present application, s of Chemical Formula 1 may be 4.

In an embodiment of the present application, when q in Chemical Formula 1 is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2 or 3, and R _b may be a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other may bond to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b can be bonded to each other to form a substituted or unsubstituted aliphatic or Aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b can be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b may be bonded to each other to form substituted or unsubstituted C3 to C60 Aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b may be bonded to each other to form substituted or unsubstituted C3 to C30 Aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b may be bonded to each other to form a C3 to C30 aromatic hydrocarbon ring.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b may be bonded to each other to form a benzene ring.

In an embodiment of the present application, R, R'and R" are the same or different from each other, and can each independently be hydrogen; deuterium; -CN; substituted or unsubstituted alkyl; substituted or unsubstituted Substituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

In another embodiment, R, R'and R" are the same or different from each other, and can each independently be hydrogen; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

In another embodiment, R, R', and R" are the same or different from each other, and can be each independently hydrogen; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment, R, R'and R" are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, R, R'and R" are the same or different from each other, and may each independently be a C6 to C60 aryl group.

In another embodiment, R, R'and R" are the same or different from each other, and may each independently be a C6 to C40 aryl group.

In another embodiment, R, R'and R" are the same or different from each other, and may each independently be a phenyl group.

The compound of Chemical Formula 1 is a bipolar compound having both P-type and N-type substituents in the core structure, and when used later as an organic material layer of an organic light-emitting device, it can block hole leakage and effectively trap excitons In the light-emitting layer. In addition, in a specific device structure, the hole properties are enhanced, and the electron mobility changes relatively slowly, which balances the electrons and holes in the light-emitting layer, thereby appropriately forming the exciton recombination region, thus increasing the efficiency and lifetime .

In addition, when a single substitution is made with a substituent having a small molecular weight, the molecular weight is small, and when it is later used as an organic material layer after an organic light-emitting device, the structural thermal stability is reduced. When double-substituted as in the chemical formula 1 of this application, the thermal stability is better than that of a single-substituted compound.

[化學式3]

[化學式4]

[化學式5]

在化學式2至化學式5中， X₁ 至X₃ 、R₁ 、R₂ 、L₁ 、L₂ 、Z₂ 及p具有與化學式1中相同的定義，且 q及s各自為1至3的整數。In the heterocyclic compound provided in an embodiment of the present application, Chemical Formula 1 is represented by any of the following Chemical Formula 2 to Chemical Formula 5. [Chemical formula 2]

[Chemical formula 3]

[Chemical formula 4]

[Chemical formula 5]

In Chemical Formula 2 to Chemical Formula 5, X ₁ to X ₃ , R ₁ , R ₂ , L ₁ , L ₂ , Z ₂ and p have the same definitions as in Chemical Formula 1, and q and s are each an integer from 1 to 3 .

[化學式7]

[化學式8]

[化學式9]

[化學式10]

[化學式11]

在化學式6至化學式11中， X₁ 至X₃ 、R₁ 、R₂ 、L₁ 及p具有與化學式1中相同的定義。In the heterocyclic compound provided in one embodiment of the present application, Chemical Formula 1 is represented by any one of Chemical Formula 6 to Chemical Formula 11 below. [Chemical formula 6]

[Chemical formula 7]

[Chemical formula 8]

[Chemical formula 9]

[Chemical formula 10]

[Chemical formula 11]

In Chemical Formula 6 to Chemical Formula 11, X ₁ to X ₃ , R ₁ , R ₂ , L ₁ and p have the same definitions as in Chemical Formula 1.

In the heterocyclic compound provided in one embodiment of the present application, Chemical Formula 1 is represented by any one of the following compounds.

The compound according to an embodiment of the present application can be prepared according to the following general formula 1. [General formula 1]

或

。In the general formula 1, Rm or Rn is the formula 1

or

.

In addition, by introducing various substituents into the structures of Chemical Formula 1 to Chemical Formula 11, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents (usually used as hole injection layer materials, hole transfer layer materials, light emitting layer materials, electron transfer layer materials, and charge generation layer materials for the manufacture of organic light-emitting devices) into the core structure, It can synthesize materials that meet the requirements of each organic material layer.

In addition, by introducing various substituents into the structures of Chemical Formula 1 to Chemical Formula 11, the energy band gap can be finely controlled, and at the same time, the characteristics at the interface between organic materials can be enhanced, and the material application can become diversified.

At the same time, the compound has a high glass transition temperature (Tg) and has excellent thermal stability. This increase in thermal stability becomes an important factor in providing the driving stability of the device.

Another embodiment of the present application provides an organic light-emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on the first electrode Between the second electrode and the second electrode, one or more of the organic material layers include heterocyclic compounds.

In an embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In an embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for the green organic light-emitting device.

In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for the red organic light-emitting device.

The specific description about the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

In addition to using the heterocyclic compound described above to form one or more organic material layers, common organic light-emitting device manufacturing methods and materials can be used to manufacture the organic light-emitting device of the present invention.

When manufacturing an organic light-emitting device, the heterocyclic compound may be formed into an organic material layer through a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating method, and the like, but is not limited thereto.

The organic material layer of the organic light-emitting device of the present invention may be formed in a single-layer structure, or may also be formed in a multilayer structure in which two or more than two organic material layers are laminated. For example, an organic light-emitting device according to an embodiment of the present disclosure may have a structure including the following as organic material layers: a hole injection layer, a hole transfer layer, a hole blocking layer, a light-emitting layer, an electron transfer layer, an electron Injection layer and the like. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound represented by Chemical Formula 1.

In another organic light emitting device, the organic material layer includes a light emitting layer, and the light emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Chemical Formula 1.

In another embodiment, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used with a phosphorescent dopant.

In another embodiment, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and may be used with an iridium-based dopant.

As the material of the phosphorescent dopant, those known in the art can be used.

For example, phosphorescent dopant materials represented by LL'MX, LL'L"M, LMXX', L2MX, and L3M may be used, however, the scope of the present disclosure is not limited to these examples.

Here, L, L', L", X, and X'are bidentate ligands different from each other, and M is a metal forming an octahedral complex.

M may include iridium, platinum, osmium, and the like.

L is an anionic bidentate ligand coordinated with M using sp2 carbon and heteroatoms as iridium-based dopants, and X can perform the function of trapping electrons or holes. Non-limiting examples of L may include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) ), (7,8-benzoquinoline), (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and similar By. Non-limiting examples of X may include acetone (acac), hexafluoroacetone, salicylidene, picolinate, 8-hydroxyquinoline, and the like.

More specific examples thereof are given below, however, the phosphorescent dopant is not limited to these examples.

In an embodiment of the present application, as an iridium-based dopant, Ir(ppy) ₃ can be used as a green phosphorescent dopant.

In an embodiment of the present application, based on the entire light-emitting layer, the dopant content may be 1% to 15%, preferably 3% to 10%, more preferably 5% to 10%.

In the organic light-emitting device of the present invention, the organic material layer includes an electron injection layer or an electron transfer layer, and the electron injection layer or the electron transfer layer may include a heterocyclic compound.

In another organic light-emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound.

In another organic light-emitting device, the organic material layer includes an electron transfer layer or a hole blocking layer, and the electron transfer layer or the hole blocking layer may include a heterocyclic compound.

The organic light-emitting device of the present invention may further include one, two or more than two layers selected from the following groups: light-emitting layer, hole injection layer, hole transfer layer, electron injection layer, electron transfer layer, electron Barrier layer and hole barrier layer.

1 to 3 illustrate the lamination sequence of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present application. However, the scope of the application is not limited to these drawings, and the structure of the organic light-emitting device known in the art can also be used in the application.

Fig. 1 illustrates an organic light-emitting device in which an anode (200), an organic material layer (300), and a cathode (400) are continuously laminated on a substrate (100). However, the structure is not limited to this structure, and as illustrated in FIG. 2, an organic light-emitting device can also be obtained in which a cathode, an organic material layer, and an anode are continuously laminated on a substrate.

Figure 3 illustrates a case where the organic material layer is multilayered. The organic light emitting device according to FIG. 3 includes a hole injection layer (301), a hole transfer layer (302), a light emitting layer (303), a hole blocking layer (304), an electron transfer layer (305), and an electron injection layer (306) ). However, the scope of the present application is not limited to this laminated structure, and if necessary, it may not include other layers except the light-emitting layer, and may further include other necessary functional layers.

In addition, an organic light-emitting device according to an embodiment of the present application includes a first electrode, a second electrode, and two or more stacks disposed between the first electrode and the second electrode, wherein the two or The more stacks each independently include a light emitting layer, a charge generation layer is included between the two or more stacks, and the charge generation layer includes a heterocyclic compound represented by Chemical Formula 1.

In addition, the organic light emitting device according to an embodiment of the present application may include a first electrode, a first stack provided on the first electrode and including a first light emitting layer, a charge generation layer provided on the first stack, A second stack on the charge generation layer and including a second light-emitting layer, and a second electrode provided on the second stack. Among them, the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1. In addition, the first stack and the second stack may each independently further include one or more of the above-mentioned hole injection layer, hole transfer layer, hole blocking layer, electron transfer layer, electron injection layer, and the like.

The charge generation layer may be an N-type charge generation layer, and in addition to the heterocyclic compound represented by Chemical Formula 1, the charge generation layer may include a dopant known in the art.

As an organic light-emitting device according to an embodiment of the present application, an organic light-emitting device having a 2-stack tandem structure is schematically illustrated in FIG. 4.

The organic material layer including Chemical Formula 1 may further include other materials as needed.

In the organic light-emitting device according to an embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are described below. However, these materials are only for the purpose of illustration and are not used to limit the scope of the present application, and may Replace with materials known in the art.

Materials with relatively large work functions can be used as anode materials, and transparent conductive oxides, metals, conductive polymers or similar materials can be used. Specific examples of the anode material include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO) ; Combinations of metals and oxides, such as ZnO: Al or SnO ₂ : Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy) )Thiophene] (PEDOT), polypyrrole, polyaniline and the like, but not limited thereto.

A material with a relatively small work function can be used as the cathode material, and metal, metal oxide, conductive polymer, or the like can be used. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gamma, aluminum, silver, tin, and lead or alloys thereof; multilayer structure materials such as LiF/Al or LiO ₂ /Al and similar, but not limited to this.

Known hole injection materials can be used as hole injection materials, and for example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst amine derivatives, can be used. -type amine derivatives), such as the third (4-hydrazino-9-ylphenyl)amine (TCTA) described in the literature [Advanced Material, 6, p. 677 (1994)], 4 ,4',4”-Tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl ]Benzene (m-MTDAPB); conductive polymer with solubility, polyaniline/dodecylbenzene sulfonic acid, poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate), Polyaniline/camphorsulfonic acid or polyaniline/poly(4-styrene-sulfonate); and similar materials.

Pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives and similar materials can be used as hole transfer materials, and low molecular or high molecular materials can also be used.

Metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, four Cyanoanthraquinone dimethane and its derivatives, quinone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, and similar materials, and can also be used High molecular materials and low molecular materials are used as electron transfer materials.

As an example of the electron injection material, LiF is generally used in this field, however, the application is not limited to this.

Materials that emit red, green, or blue light can be used, and two or more luminescent materials can be mixed and used as luminescent materials as needed. Here, two or more luminescent materials can be used by deposition as a separate supply source or by pre-mixing and deposition as one supply source. In addition, fluorescent materials can also be used as luminescent materials, however, phosphorescent materials can also be used. A material that emits light by bonding electrons and holes respectively injected from the anode and the cathode can be used alone as the light-emitting material. However, a material having a host material and a dopant material (participating in light emission at the same time) can also be used.

When mixing luminescent material hosts, the same series of hosts can be mixed, or different series of hosts can be mixed. For example, any two or more types of n-type host materials or p-type host materials can be selected and used as the host material of the light-emitting layer.

Depending on the material used, the organic light-emitting device according to an embodiment of the present application may be a top emission type, a bottom emission type, or a double-side emission type.

The heterocyclic compound according to an embodiment of the present application can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like under similar principles for organic light-emitting devices.

Hereinafter, the present invention will be described in more detail with reference to examples, however, these are only for the purpose of illustration, and the scope of the application is not limited thereto. ＜ Preparation example ＞

< Preparation Example 1> Preparation of Compound 1

1) Preparation compound 1-1

Dissolve (1H-indol-2-yl)boronic acid (100 g, 0.621 mol) and 2-bromo-5-chloroaniline (115 g, 0.558 mol) in toluene, EtOH and H ₂ O (1000 ml: 200 ml: 200 ml), Pd(PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added thereto, and the result was stirred at 100° C. for 3 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ , and then the solvent was removed using a rotary evaporator to obtain compound 1-1 (110 g, 74%) in liquid form.

2) Preparation compound 1-2

Compound 1-1 (110 g, 0.428 mol) and triethylamine (89 mL, 0.642 mol) were introduced into dichloromethane (MC) (1200 mL) and dissolved in it. At 0°C, benzyl chloride (90.24 g, 0.642 mol) dissolved in MC (300 ml) was slowly added dropwise to the mixture. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 1-2 (129 g, 83%) in liquid form.

3) Preparation compound 1-3

After dissolving compound 1-2 (129 g, 0.355 mol) in nitrobenzene (1500 ml), POCl ₃ (50 ml, 0.533 mol) was slowly added dropwise thereto. The result was reacted at 140°C for 15 hours. After the reaction is completed, a distilled aqueous solution with NaHCO ₃ dissolved in it is slowly added to the reaction solution, and the result is stirred. Filter and collect the resulting solid. The collected solid was recrystallized with MC and MeOH to obtain compound 1-3 (65 g, 53%) in solid form.

4) Preparation compound 1-4

In compound 1-3 (10 g, 0.029 mol), bis(pinacol) diboron (8.8 g, 0.035 mol), KOAc (8.5 g, 0.087 mol), Sphos (2.4 g, 0.0058 mol) And Pd(dba) ₂ (1.7 g, 0.0029 mol) was dissolved in 1,4-dioxane (200 ml) solution, and the result was reacted at 90°C for 5 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 1-4 (11.4 g, 90%).

5) Preparation compound 1

Compound 1-4 (11.4 g, 0.026 mol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 0.024 mol) were dissolved in toluene, EtOH and H ₂ O (100 ml: 20 ml: 20 ml), add Pd(PPh ₃ ) ₄ (1.4 g, 0.0012 mol) and K ₂ CO ₃ (9.2 g, 0.072 mol) to it, and put the result at 100 Stir for 5 hours at °C. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ , and then the solvent was removed using a rotary evaporator to obtain compound 1 (9.4 g, 72%).

The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate A of Table 1 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

72% 4

67% 5

66% 9

75% 206

72% 210

77% 217

67% 255

66% 368

75% 370

74% 372

69% 542

70% 543

79% 998

69% [Table 1] Compound number Intermediate A Target compound Yield 1

72% 4

67% 5

66% 9

75% 206

72% 210

77% 217

67% 255

66% 368

75% 370

74% 372

69% 542

70% 543

79% 998

69%

The target compound was synthesized in the same manner as Preparation Example 1, except that 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline, and Intermediate B of Table 2 below was used instead of 2-bromo- 4,6-Diphenyl-1,3,5-triazine.

72% [Table 2] Compound number Intermediate B Target compound Yield 13

72%

The target compound was synthesized in the same manner as Preparation Example 1, except that 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and Intermediate C in Table 3 below was used instead of 2-bromo- 4,6-Diphenyl-1,3,5-triazine.

68% 34

66% 235

66% 238

67% [table 3] Compound number Intermediate C Target compound Yield twenty four

68% 34

66% 235

66% 238

67%

The target compound was synthesized in the same manner as Preparation Example 1, except that 2-bromo-3-chloroaniline was used instead of 2-bromo-5-chloroaniline, and Intermediate D of Table 4 below was used instead of 2-bromo- 4,6-Diphenyl-1,3,5-triazine.

75% [Table 4] Compound number Intermediate D Target compound Yield 248

75%

The target compound was synthesized in the same manner as Preparation Example 1, except that 1-naphthoyl chloride was used instead of benzyl chloride, and Intermediate E of Table 5 below was used instead of 2-bromo-4,6-diphenyl Base-1,3,5-triazine.

69% 264

68% 547

70% [table 5] Compound number Intermediate E Target compound Yield 260

69% 264

68% 547

70%

The target compound was synthesized in the same manner as Preparation Example 1, except that 1-naphthoyl chloride was used instead of benzyl chloride, 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline, and The intermediate F of Table 6 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

76% 272

77%   275

67% 277

64% 999

62% [Table 6] Compound number Intermediate F Target compound Yield 44

76% 272

77% 275

67% 277

64% 999

62%

The target compound was synthesized in the same manner as in Preparation Example 1, except that 1-naphthoyl chloride was used instead of benzyl chloride, and 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and The intermediate G of Table 7 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

70% 285

76% 287

80% [Table 7] Compound number Intermediate G Target compound Yield 283

70% 285

76% 287

80%

The target compound was synthesized in the same manner as Preparation Example 1, except that 1-naphthoyl chloride was used instead of benzyl chloride, 2-bromo-3-chloroaniline was used instead of 2-bromo-5-chloroaniline, and The intermediate H of Table 8 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

79% [Table 8] Compound number Intermediate H Target compound Yield 57

79%

The target compound was synthesized in the same manner as Preparation Example 1, except that 9-chlorophenanthrene was used instead of benzyl chloride, and Intermediate I of Table 9 below was used instead of 2-bromo-4,6-diphenyl- 1,3,5-Triazine.

74% 65

66% 312

68% 551

71% [Table 9] Compound number Intermediate I Target compound Yield 64

74% 65

66% 312

68% 551

71%

The target compound was synthesized in the same manner as Preparation Example 1, except that 9-chlorophenanthrene was used instead of benzyl chloride, 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the following Intermediate J of Table 10 replaces 2-bromo-4,6-diphenyl-1,3,5-triazine.

62% [Table 10] Compound number Intermediate J Target compound Yield 318

62%

The target compound was synthesized in the same manner as Preparation Example 1, except that 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline and 4-(naphthalene-1-yl)benzyl chloride was used Instead of benzyl chloride, the intermediate K of Table 11 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% [Table 11] Compound number Intermediate K Target compound Yield 1003

71%

The target compound was synthesized in the same manner as in Preparation Example 1, except that 9-chlorophenanthrene was used instead of benzyl chloride, 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the following Intermediate L in Table 12 replaces 2-bromo-4,6-diphenyl-1,3,5-triazine.

67% 332

70% [Table 12] Compound number Intermediate L Target compound Yield 328

67% 332

70%

The target compound was synthesized in the same manner as in Preparation Example 1, except that 9-chlorophenanthrene was used instead of benzyl chloride, 2-bromo-3-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the following Intermediate M in Table 13 replaces 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% [Table 13] Compound number Intermediate M Target compound Yield 78

71%

The target compound was synthesized in the same manner as Preparation Example 1, except that 2-chlorotriphenylene chloride was used instead of benzyl chloride, and Intermediate N of Table 14 below was used instead of 2-bromo-4,6-diphenyl Base-1,3,5-triazine.

68% 100

70% 101

64% 346

78% 348

76% 555

77% [Table 14] Compound number Intermediate N Target compound Yield 84

68% 100

70% 101

64% 346

78% 348

76% 555

77%

The target compound was synthesized in the same manner as in Preparation Example 1, except that [1,1'-biphenyl]-4-carbazide chloride was used instead of benzyl chloride, and the intermediate O of Table 15 below was used instead 2-Bromo-4,6-diphenyl-1,3,5-triazine.

68% [Table 15] Compound number Intermediate O Target compound Yield 1002

68%

The target compound was synthesized in the same manner as in Preparation Example 1, except that 2-chlorotriphenylene was used instead of benzoyl chloride, 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and The intermediate P of Table 16 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

72% 355

68% 358

70% 359

73% [Table 16] Compound number Intermediate P Target compound Yield 92

72% 355

68% 358

70% 359

73%

The target compound was synthesized in the same manner as Preparation Example 1, except that 4-(naphthalen-1-yl)benzyl chloride was used instead of benzyl chloride, and Intermediate Q in Table 17 below was used instead of 2-bromo -4,6-Diphenyl-1,3,5-triazine.

69% [Table 17] Compound number Intermediate Q Target compound Yield 302

69%

The target compound was synthesized in the same manner as Preparation Example 1, except that 4-(naphthalene-9-yl)benzyl chloride was used instead of benzyl chloride, and the intermediate R of Table 18 below was used instead of 2-bromo -4,6-Diphenyl-1,3,5-triazine.

70% [Table 18] Compound number Intermediate R Target compound Yield 342

70%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and the intermediate S of Table 19 below was used instead of 2. -Bromo-4,6-diphenyl-1,3,5-triazine.

79% 105

71% 106

74% 198

68% 202

69% 387

74% 536

70% 537

77% 539

74% [Table 19] Compound number Intermediate S Target compound Yield 102

79% 105

71% 106

74% 198

68% 202

69% 387

74% 536

70% 537

77% 539

74%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-6-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, and use the intermediate T of Table 20 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

67% 561

66% [Table 20] Compound number Intermediate T Target compound Yield 394

67% 561

66%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-4-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, and use the intermediate U of Table 21 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

70% 122

71% 124

74% 135

80% 403

79% 406

69% [Table 21] Compound number Intermediate U Target compound Yield 119

70% 122

71% 124

74% 135

80% 403

79% 406

69%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-4-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, using 9-chlorophenanthrene instead of benzyl chloride, and using intermediate V of Table 22 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

70% [Table 22] Compound number Intermediate V Target compound Yield 1008

70%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-4-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, using [1,1'-biphenyl]-3-carbazide chloride instead of benzyl chloride, and using the intermediate W of Table 23 below instead of 2-bromo-4,6-di Phenyl-1,3,5-triazine.

70% [Table 23] Compound number Intermediate W Target compound Yield 1012

70%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-3-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, and use intermediate X of Table 24 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

67% 561

73% [Table 24] Compound number Intermediate X Target compound Yield 415

67% 561

73%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-3-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, using 4-(naphthalene-1-yl)benzyl chloride instead of benzyl chloride, and using the intermediate Y of Table 25 below instead of 2-bromo-4,6-diphenyl- 1,3,5-Triazine.

68% [Table 25] Compound number Intermediate Y Target compound Yield 1013

68%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 1-naphthomethacrylate chloride was used instead of benzoic acid. Chlorine, and the intermediate Z of Table 26 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

74% 427

67% 432

69% [Table 26] Compound number Intermediate Z Target compound Yield 138

74% 427

67% 432

69%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 1-naphthomethacrylate chloride was used instead of benzoic acid. Chlorine, use 2-bromo-4-chloroaniline instead of 2-bromo-5-chloroaniline, and use intermediate A-1 of Table 27 below instead of 2-bromo-4,6-diphenyl-1,3,5 -Triazine.

70% 447

71% 453

77% 458

72% [Table 27] Compound number Intermediate A-1 Target compound Yield 152

70% 447

71% 453

77% 458

72%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 1-naphthomethacrylate chloride was used instead of benzoic acid. Chlorine, use 2-bromo-3-chloroaniline instead of 2-bromo-5-chloroaniline, and use intermediate B-1 of Table 28 below instead of 2-bromo-4,6-diphenyl-1,3,5 -Triazine.

80% 464

81% [Table 28] Compound number Intermediate B-1 Target compound Yield 159

80% 464

81%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 9-chlorophenanthrene was used instead of benzyl chloride, And use the intermediate C-1 of Table 29 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

76% 476

73% 567

77% [Table 29] Compound number Intermediate C-1 Target compound Yield 473

76% 476

73% 567

77%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 9-chlorophenanthrene was used instead of benzyl chloride, Use 2-bromo-4-chloroaniline instead of 2-bromo-5-chloroaniline, and use Intermediate D-1 in Table 30 below instead of 2-bromo-4,6-diphenyl-1,3,5-tri Azine.

76% 497

69% 1008

68% [Table 30] Compound number Intermediate D-1 Target compound Yield 490

76% 497

69% 1008

68%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 9-chlorophenanthrene was used instead of benzyl chloride, Use 2-bromo-3-chloroaniline instead of 2-bromo-5-chloroaniline, and use the intermediate E-1 of Table 31 below instead of 2-bromo-4,6-diphenyl-1,3,5-tri Azine.

68% 505

70% 509

73% [Table 31] Compound number Intermediate E-1 Target compound Yield 175

68% 505

70% 509

73%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-chlorotriphenylene was used instead of benzoic acid. Chloro, and use intermediate F-1 of Table 32 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% 195

70% 196

66% 197

69% 517

74% 534

68% 571

70% [Table 32] Compound number Intermediate F-1 Target compound Yield 181

71% 195

70% 196

66% 197

69% 517

74% 534

68% 571

70%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-chlorotriphenylene was used instead of benzoic acid. Chlorine, use 2-bromo-4-chloroaniline instead of 2-bromo-5-chloroaniline, and use Intermediate G-1 in Table 33 below instead of 2-bromo-4,6-diphenyl-1,3,5 -Triazine.

69% [Table 33] Compound number Intermediate G-1 Target compound Yield 527

69%

The target compound was synthesized in the same manner as in Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-chlorotriphenylene was used instead of benzoic acid. Chlorine, use 2-bromo-3-chloroaniline instead of 2-bromo-5-chloroaniline, and use intermediate H-1 in Table 34 below instead of 2-bromo-4,6-diphenyl-1,3,5 -Triazine.

73% [Table 34] Compound number Intermediate H-1 Target compound Yield 192

73%

The target compound was synthesized in the same manner as Preparation Example 1, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 4-(naphthalene-1-yl)benzene was used. Formyl chloride was substituted for benzyl chloride, and the intermediate C-1 of Table 35 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

69% [Table 35] Compound number Intermediate I-1 Target compound Yield 161

69%

< Preparation Example 2> Preparation of compound 574

1) Preparation compound 574-1

Dissolve (1H-indol-2-yl)boronic acid (100 g, 0.621 mol) and 2-bromo-5-chloroaniline (115 g, 0.558 mol) in toluene, EtOH and H ₂ O (1000 ml: 200 ml: 200 ml), Pd(PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added thereto, and the result was stirred at 100° C. for 3 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 574-1 (110 g, 74%) in liquid form.

2) Preparation compound 574-2

After dissolving compound 574-1 (110 g, 0.428 mol) and phenylboronic acid (89 ml, 0.574 mol) in THF and H ₂ O (1000 ml: 200 ml), Pd(PPh ₃ ) was introduced into it ₄ (24.7 g, 0.021 mol) and K ₂ CO ₃ (170 g, 1.284 mol), and stir the result at 66°C for 3 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ , and then the solvent was removed using a rotary evaporator to obtain compound 574-2 (112 g, 87%) in liquid form.

3) Preparation compound 574-3

Compound 574-2 (112 g, 0.372 mol) and triethylamine (78 mL, 0.558 mol) were introduced into MC (1200 mL) and dissolved in it. At 0°C, 4-chlorobenzyl chloride (78.12 g, 0.446 mol) dissolved in MC (300 ml) was slowly added dropwise to the mixture. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ , and then the solvent was removed using a rotary evaporator to obtain compound 574-3 (130 g, 79%) in liquid form.

4) Preparation compound 574-4

After dissolving compound 574-3 (130 g, 0.295 mol) in nitrobenzene (1500 ml), POCl ₃ (50 ml, 0.443 mol) was slowly added dropwise thereto. The result was reacted at 140°C for 15 hours. After the reaction is completed, a distilled aqueous solution with NaHCO ₃ dissolved in it is slowly added to the reaction solution, and the result is stirred. Filter and collect the resulting solid. The collected solid was recrystallized with MC and MeOH to obtain compound 574-4 (68 g, 53%) in solid form.

5) Preparation compound 574-5

In compound 574-4 (10 g, 0.023 mol), bis(pinacol) diboron (8.8 g, 0.035 mol), KOAc (6.7 g, 0.069 mol), Sphos (1.8 g, 0.0046 mol) And Pd(dba) ₂ (1.3 g, 0.0023 mol) was dissolved in 1,4-dioxane (200 ml) solution, and the result was reacted at 90°C for 5 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 574-5 (10.6 g, 90%).

6) Compound 574 Preparation

Compound 574-5 (10.6 g, 0.021 mol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 0.024 mol) were dissolved in toluene, EtOH and H ₂ O (100 ml: 20 ml: 20 ml), add Pd(PPh ₃ ) ₄ (1.2 g, 0.0010 mol) and K ₂ CO ₃ (8.1 g, 0.063 mol) to it, and set the result at 100 Stir for 5 hours at °C. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ , and then the solvent was removed using a rotary evaporator to obtain compound 574 (9.7 g, 75%).

The target compound was synthesized in the same manner as Preparation Example 2, except that Intermediate J-1 of Table 36 below was used instead of phenylboronic acid, and Intermediate K-1 of Table 36 below was used instead of 2-bromo-4, 6-Diphenyl-1,3,5-triazine.

77% 575

79% 594

67% 610

77% 618

79% 634

80% 650

74% 652

79% 744

69% 746

70% 768

74% 789

71% 807

71% 813

78% 818

69% 824

64% 826

77% 1014

72% 1018

  [Table 36] Compound number Intermediate J-1 Intermediate K-1 Compound Yield 574

77% 575

79% 594

67% 610

77% 618

79% 634

80% 650

74% 652

79% 744

69% 746

70% 768

74% 789

71% 807

71% 813

78% 818

69% 824

64% 826

77% 1014

72% 1018

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the intermediate L-1 of Table 37 below was used instead of phenylboronic acid , And use the intermediate M-1 of Table 37 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

79% 621

77% [Table 37] Compound number Intermediate L-1 Intermediate M-1 Compound Yield 607

79% 621

77%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-6-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the intermediate N-1 of Table 38 below was used instead of phenylboronic acid , And use the intermediate O-1 of Table 38 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% [Table 38] Compound number Intermediate N-1 Intermediate O-1 Compound Yield 1019

71%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the intermediate P-1 of Table 39 below was used instead of phenylboronic acid , And use the intermediate Q-1 of Table 39 below to replace 2-bromo-4,6-diphenyl-1,3,5-triazine.

79% 758

81% 796

78% [Table 39] Compound number Intermediate P-1 Intermediate Q-1 Compound Yield 614

79% 758

81% 796

78%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the intermediate R-1 of Table 40 below was used instead of phenylboronic acid , And use the intermediate S-1 of Table 40 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

79% [Table 40] Compound number Intermediate R-1 Intermediate S-1 Compound Yield 1016

79%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-3-chloroaniline was used instead of 2-bromo-5-chloroaniline, and the intermediate T-1 of Table 41 below was used instead of phenylboronic acid , And use intermediate U-1 in Table 41 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

78% 627

67% 643

66% 781

69% 802

70% [Table 41] Compound number Intermediate T-1 Intermediate U-1 Compound Yield 591

78% 627

67% 643

66% 781

69% 802

70%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and the intermediate V-1 of Table 42 below was used instead Phenylboronic acid, and the intermediate W-1 of Table 42 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% 674

73% 687

76% 723

80% 734

79% 737

80% 739

71% 741

74% 830

73% 831

71% 855

66% 877

67% 894

67% 902

70% 910

71% 920

71% 923

79% 925

78% [Table 42] Compound number Intermediate V-1 Intermediate W-1 Compound Yield 657

71% 674

73% 687

76% 723

80% 734

79% 737

80% 739

71% 741

74% 830

73% 831

71% 855

66% 877

67% 894

67% 902

70% 910

71% 920

71% 923

79% 925

78%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and the intermediate X-1 of Table 43 below was used instead Phenylboronic acid, and the intermediate Y-1 of Table 43 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

69% 861

69% 907

71% 1024

68% [Table 43] Compound number Intermediate X-1 Intermediate Y-1 Compound Yield 700

69% 861

69% 907

71% 1024

68%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and the intermediate Z-1 of Table 44 below was used instead Phenylboronic acid, and intermediate A-2 of Table 44 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

72% 844

79% 883

71% [Table 44] Compound number Intermediate Z-1 Intermediate A-2 Compound Yield 692

72% 844

79% 883

71%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-3-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, using intermediate B-2 of Table 45 below instead of phenylboronic acid, and using intermediate C-2 of Table 45 below instead of 2-bromo-4,6-diphenyl-1,3 ,5-Triazine.

66% 695

67% 918

67% 919

70% 1026

73% [Table 45] Compound number Intermediate B-2 Intermediate C-2 Compound Yield 684

66% 695

67% 918

67% 919

70% 1026

73%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline, and 3-chlorobenzyl chloride was used instead of 4-chlorobenzyl As for the chlorine, use the intermediate D-2 of the following table 46 instead of phenylboronic acid, and use the intermediate E-2 of the following table 46 instead of 2-bromo-4,6-diphenyl-1,3,5-triazine .

70% [Table 46] Compound number Intermediate D-2 Intermediate E-2 Compound Yield 585

70%

The target compound was synthesized in the same manner as Preparation Example 2, except that 2-bromo-3-chloroaniline was used instead of 2-bromo-5-chloroaniline, and 3-chlorobenzyl chloride was used instead of 4-chlorobenzyl For chlorin, use the intermediate F-2 of the following table 47 instead of phenylboronic acid, and use the intermediate G-2 of the following table 47 instead of 2-bromo-4,6-diphenyl-1,3,5-triazine .

76% [Table 47] Compound number Intermediate F-2 Intermediate G-2 Compound Yield 804

76%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 3-chlorobenzoyl chloride was used instead of 4- Chlorobenzoyl chloride, use the intermediate H-2 of the following table 48 instead of phenylboronic acid, and use the intermediate 1-2 of the following table 48 instead of 2-bromo-4,6-diphenyl-1,3,5 -Triazine.

75% [Table 48] Compound number Intermediate H-2 Intermediate I-2 Compound Yield 708

75%

The target compound was synthesized in the same manner as Preparation Example 2, except that benzofuran-2-ylboronic acid was used instead of (1H-indol-2-yl)boronic acid, and 2-bromo-4-chloroaniline was used instead of 2. -Bromo-5-chloroaniline, using 3-chlorobenzyl chloride instead of 4-chlorobenzyl chloride, using intermediate J-2 of Table 49 below instead of phenylboronic acid, and using intermediate K- of Table 49 below 2 replaces 2-bromo-4,6-diphenyl-1,3,5-triazine.

70% 729

79% [Table 49] Compound number Intermediate J-2 Intermediate K-2 Compound Yield 667

70% 729

79%

< Preparation Example 3> Preparation of compound 926

1) Preparation compound 926-1

Dissolve benzo[b]thiophen-2-ylboronic acid (100 g, 0.562 mol) and 2-bromonaphthalene-1-amine (125 g, 0.562 mol) in toluene, EtOH and H ₂ O (1000 ml: 200 ml: 200 ml), Pd(PPh ₃ ) ₄ (32.4 g, 0.028 mol) and NaHCO ₃ (141.6 g, 1.686 mol) were added thereto, and the result was stirred at 100° C. for 3 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 926-1 (106 g, 68%) in liquid form.

2) Preparation compound 926-2

Compound 926-1 (106 g, 0.385 mol) and triethylamine (64 mL, 0.462 mol) were introduced into MC (1200 mL) and dissolved in it. At 0°C, 4-chlorobenzyl chloride (67.38 g, 0.385 mol) dissolved in MC (300 ml) was slowly added dropwise to the mixture. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 926-2 (120 g, 75%) in liquid form.

4) Preparation compound 926-3

After dissolving compound 926-2 (120 g, 0.290 mol) in nitrobenzene (1500 ml), POCl ₃ (50 ml, 0.443 mol) was slowly added dropwise thereto. The result was reacted at 140°C for 15 hours. After the reaction is completed, a distilled aqueous solution with NaHCO ₃ dissolved in it is slowly added to the reaction solution, and the result is stirred. Filter and collect the resulting solid. The collected solid was recrystallized with MC and MeOH to obtain compound 926-3 (71 g, 61%) in solid form.

5) Preparation compound 926-4

In compound 926-3 (10 g, 0.025 mol), bis(pinacol) diboron (8.8 g, 0.035 mol), KOAc (6.7 g, 0.069 mol), Sphos (1.8 g, 0.0046 mol) And Pd(dba) ₂ (1.3 g, 0.0023 mol) was dissolved in 1,4-dioxane (200 ml) solution, and the result was reacted at 90°C for 5 hours. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 926-4 (9.8 g, 80%).

6) Compound 926 Preparation

Compound 926-4 (9.8 g, 0.020 mol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 0.024 mol) were dissolved in toluene, EtOH and H ₂ O (100 ml: 20 ml: 20 ml), add Pd(PPh ₃ ) ₄ (1.2 g, 0.0010 mol) and K ₂ CO ₃ (8.1 g, 0.063 mol) to it, and set the result at 100 Stir for 5 hours at °C. After the reaction is completed, MC and distilled water are added to the reaction solution for extraction. After that, the result was dried with anhydrous MgSO ₄ and then the solvent was removed using a rotary evaporator to obtain compound 926 (9.5 g, 80%).

The target compound was synthesized in the same manner as Preparation Example 3 except that the intermediate L-2 of Table 50 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

62% 928

67% 932

65% 936

71% 937

68% 1020

70% [Table 50] Compound number Intermediate L-2 Target compound Yield 926

62% 928

67% 932

65% 936

71% 937

68% 1020

70%

The target compound was synthesized in the same manner as Preparation Example 3, except that 3-chlorobenzyl chloride was used instead of 4-chlorobenzyl chloride, and the intermediate M-2 of Table 51 below was used instead of 2-bromo- 4,6-Diphenyl-1,3,5-triazine.

62% [Table 51] Compound number Intermediate M-2 Target compound Yield 927

62%

The target compound was synthesized in the same manner as Preparation Example 3, except that benzofuran-2-ylboronic acid was used instead of benzo[b]thiophen-2-ylboronic acid, and 3-chlorobenzoyl chloride was used instead of 4- Chlorobenzoyl chloride, and intermediate N-2 of Table 52 below was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

62% 945

74% [Table 52] Compound number Intermediate N-2 Target compound Yield 943

62% 945

74%

The target compound was synthesized in the same manner as Preparation Example 3, except that 3-bromonaphthalene-2-amine was used instead of 2-bromonaphthalene-1-amine, and the intermediate O-2 of Table 53 below was used instead of 2- Bromo-4,6-diphenyl-1,3,5-triazine.

63% 952

66% 954

67% 956

70% 959

69% 961

65% [Table 53] Compound number Intermediate O-2 Target compound Yield 950

63% 952

66% 954

67% 956

70% 959

69% 961

65%

The target compound was synthesized in the same manner as in Preparation Example 3, except that benzofuran-2-ylboronic acid was used instead of benzo[b]thiophen-2-ylboronic acid, and 3-bromonaphthalene-2-amine was used instead of 2. -Bromonaphthalene-1-amine, and use intermediate P-2 of Table 54 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

69% 969

72% 971

71% [Table 54] Compound number Intermediate P-2 Target compound Yield 962

69% 969

72% 971

71%

The target compound was synthesized in the same manner as Preparation Example 3, except that 1-bromonaphthalene-2-amine was used instead of 2-bromonaphthalene-1-amine, and the intermediate Q-2 of Table 55 below was used instead of 2- Bromo-4,6-diphenyl-1,3,5-triazine.

76% 980

76% 1022

70% [Table 55] Compound number Intermediate Q-2 Target compound Yield 978

76% 980

76% 1022

70%

The target compound was synthesized in the same manner as in Preparation Example 3, except that 1-bromonaphthalene-2-amine was used instead of 2-bromonaphthalene-1-amine, and 3-chlorobenzyl chloride was used instead of 4-chlorobenzyl And use the intermediate R-2 of Table 56 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

71% [Table 56] Compound number Intermediate R-2 Target compound Yield 977

71%

The target compound was synthesized in the same manner as Preparation Example 3, except that benzofuran-2-ylboronic acid was used instead of benzo[b]thiophen-2-ylboronic acid, and 1-bromonaphthalene-2-amine was used instead of 2. -Bromonaphthalene-1-amine, and use the intermediate S-2 of Table 57 below instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

74% 990

73% 996

78% [Table 57] Compound number Intermediate S-2 Target compound Yield 986

74% 990

73% 996

78%

Table 58 and Table 59 below give the 1H NMR data and FD-MS data of the synthesized compounds, and the synthesis of the target compound can be identified through the following data.

[Table 58] NO ¹ H NMR (CDCl ₃ , 300 Mz) 1 δ=8.45(1H, m), 8.30~8.27(7H, m), 8.12(1H, d), 8.03~7.98(2H, m), 7.54~7.41(12H, m) 4 δ=8.45(1H, t), 8.27~8.30(7H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.85(2H, d), 7.41~7.54(11H, m), 7.25(2H, d) 5 δ=8.45(1H, m), 8.26~8.30(7H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.85(2H, d), 7.41~7.54(11H, m) 9 δ=8.45(2H, d), 8.27~8.30(3H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.85(6H, d), 7.41~7.54(15H, m), 7.25(6H, d) 13 δ=8.45(1H, m), 8.21~8.30(7H, m), 7.98~8.02(2H, m), 7.85(2H, d), 7.66(1H, t), 7.41~7.54(11H, m), 7.25(2H, d) twenty four δ=8.45(1H, m), 8.21~8.30(8H, m), 8.04(1H, d), 7.98(1H, m), 7.90(1H, s), 7.70 (1H, s), 7.41~7.54( 13H, m) 34 δ=8.97(2H, d), 8.30(2H, d), 8.21(1H, d), 7.98(1H, d), 8.04(1H, m), 7.90(1H, s), 7.45~7.83(8H, m), 7.45~7.52(11H, m), 7.25(4H, s) 44 δ=8.45(1H, m), 8.46~8.55(2H, m), 8.28(4H, d), 8.21(1H, d), 7.98~8.10(4H, m), 7.85(2H, d), 7.41~ 7.55(12H, m), 7.25 (2H, d) 57 δ=8.66(1H, m), 8.46(2H, m), 8.28(2H, d), 7.94~8.10(6H, m), 7.85(4H, d), 7.41~7.64(13H, m), 7.25( 4H, d) 64 δ=8.93(2H, d), 8.44(2H, d), 8.27~8.28(5H, m), 8.12(3H, d), 7.98~8.03(2H, m), 7.82~7.88(6H, m), 7.41~7.52(8H, m), 7.25(2H, d) 65 δ=8.69(2H, d), 8.55(2H, d), 8.24~8.68(6H, m), 8.12(3H, d), 7.98~8.03(2H, m), 7.82~7.88(4H, m), 7.70(1H, s), 7.41~7.57(10H, m) 78 δ=8.93(2H, d), 8.44(2H, d), 8.24~8.28(5H, m), 8.12(2H, d), 7.82~7.98(10H, m), 7.70(1H, s), 7.41~ 7.57(10H, m) 84 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, m), 8.21~8.28(6H, m), 8.12(3H, d), 7.98~8.03( 2H, m), 7.82~7.88(6H, m), 7.41~7.51(8H, m), 7.25(2H, d) 92 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 9.66(1H, m), 8.21~8.68(6H, m), 8.12(2H, d), 8.04(1H, d), 7.98(1H, m), 7.82~7.90(7H, m), 7.42~7.51(8H, m), 7.25(2H, d) 100 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 9.66(1H, m), 8.28(2H, d), 8.27(1H, s), 8.21(1H, s) , 8.12(3H, d), 7.98~8.06(3H, m), 7.82~7.88(5H, m), 7.38~7.61(9H, m), 7.28(1H, m) 101 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, m), 8.27(1H, s), 8.21(1H, s), 8.12(3H, d) , 7.98~8.03(2H, m), 7.77~7.88(12H, m), 7.45~7.52(8H, m) 102 δ=8.27~8.30(7H, m), 8.12(1H, d), 8.03(1H, d), 7.89(1H, d), 7.66(1H, d), 7.41~7.54(11H, m) 105 δ=8.27~8.30(7H, m), 8.12(1H, d), 8.03(1H, d), 7.85~7.89(3H, d), 7.66(1H, d), 7.32~7.54(13H, m) 106 δ=8.27~8.30(7H, m), 8.12(1H, d), 8.03(1H, d), 7.85~7.89(3H, m), 7.66(1H, d), 7.32~7.54(11H, m), 7.25(6H, t) 119 δ=8.28~8.30(6H, m), 8.21(1H, d), 8.04(1H, d), 7.89~7.90(2H, d), 7.66(1H, d), 7.32~7.54(11H, m) 122 δ=8.28~8.30(6H, m), 8.21(1H, d), 8.04(1H, d), 7.85~7.90(4H, m), 7.66(1H, d), 7.32~7.54(11H, m), 7.25(2H, d) 124 δ=8.30 (2H, d), 8.21(1H, d), 8.04(1H, d), 7.85~7.90(8H, m), 7.66(1H, d), 7.32~7.54(15H, m), 7.25( 6H, d) 135 δ=8.30(2H, d), 8.21(1H, d), 8.04(1H, d), 7.77~7.89(10H, m), 7.66(1H, d), 7.32~7.54(11H, m), 7.25( 4H, s) 138 δ=8.55(1H, m), 8.16(1H, d), 8.27~8.28(5H, d), 8.03~8.12(4H, m), 7.85~7.89(3H, m), 7.32~7.66(12H, m) ), 7.25(2H, d) 152 δ=8.55(1H, m), 8.46(1H, d), 8.28(2H, d), 8.21(1H, d), 8.04~8.10(3H, m), 7.85~7.90(6H, m), 7.32~ 7.66(14H, m), 7.25(4H, d) 159 δ=8.55(1H, m), 8.46(1H, d), 8.24~8.28(5H, m), 7.89~8.10(6H, m), 7.32~7.66(15H, m) 161 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 8.27~8.28(5H, m), 8.03~8.12(4H, m), 7.85~7.89(3H, m), 7.25~7.66(16H, m) 175 δ=8.93(2H, d), 8.44(1H, s), 8.28(4H, d), 8.12(2H, d), 7.82~8.03(10H, m), 7.66(1H, d), 7.32~7.51( 10H, m) 181 δ=9.66(1H, s), 8.93(1H, d), 8.55(1H, d), 8.21~8.28(6H, m), 8.12(1H, d), 8.03(1H, d), 7.82~7.89( 7H, m), 7.66(1H, m), 7.25~7.51(10H, m) 192 δ=9.66(1H, s), 8.93(1H, d), 8.55(1H, d), 8.21~8.28(5H, m), 8.12(2H, d), 7.85~8.03(10H, m), 7.66( 1H, d), 7.25~7.51(10H, m) 195 δ=9.66(1H, s), 8.93(1H, d), 8.55(1H, d), 8.28(2H, d), 8.21(1H, 2), 8.12(4H, d), 8.03(1H, d) , 7.82~7.94(6H, m), 7.63~7.66(2H, m), 7.29~7.51(9H, m) 196 δ=9.66(1H, s), 8.93(1H, d), 8.55(1H, d), 8.28(2H, d), 8.27(1H, s), 8.21(1H, s), 8.12(3H, d) , 8.03~8.06(2H, m), 7.82~7.89(6H, m), 7.51~7.66(6H, m), 7.28~7.41(5H, m) 197 δ=9.66(1H, s), 8.93(1H, d), 8.55(1H, d), 8.27(1H, s), 8.21(1H, d), 8.12(3H, d), 8.03(1H, d) , 7.77~7.89(13H, m), 7.66(1H, d), 7.45(6H, m), 7.32~7.38(2H, m) 198 δ=8.55(1H, d), 8.27~8.30(5H, m), 8.12(2H, d), 8.03(1H, d), 7.89~7.94(2H, m), 7.79(2H, d), 7.29~ 7.68(16H, m) 202 δ=8.41~8.45(2H, m), 8.20~8.30(6H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.85~7.89(3H, m), 7.25~7.66(14H , m) 206 δ=8.45(1H, m), 8.27~8.30(5H, m), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.79(2H, d), 7.41~ 7.54(11H, m) 210 δ=8.46(1H, m), 8.27~8.30(3H, m), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.79~7.85(6H, m), 7.41~7.54(11H, m), 7.25(6H, t) 217 δ=8.45(1H, m), 8.27~8.30(9H, m), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.85(4H, d), 7.41~ 7.54(13H, m) 235 δ=8.45(1H, m), 8.21~8.30(8H, m), 8.04(1H, d), 7.98(1H, m), 7.90(1H, s), 7.85(2H, d), 7.41~7.54( 13H, m) 238 δ=8.45(1H, m), 8.30(4H, d), 8.23(1H, s), 8.21(1H, d), 8.04(1H, d), 7.98(1H, m), 7.90(1H, s) , 7.85(6H, d), 7.41~7.54(15H, m), 7.25(2H, d) 248 δ=8.45(1H, m), 8.30(2H, d), 8.23(1H, s), 7.94~8.03(4H, m), 7.79~7.85(6H, m), 7.41~7.54(11H, m), 7.25(2H, d) 255 δ=8.45(1H, d), 8.30(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 7.98~8.06(3H, m), 7.79~7.87( 5H, m), 7.41~7.61(12H, m), 7.25(2H, m) 260 δ=8.55(1H, m), 8.45~8.46(2H, m), 8.27~8.30(5H, m), 8.23(1H, s), 7.98~8.12(5H, m), 7.85(2H, d), 7.64(1H, t), 7.41~7.55(12H, m) 264 δ=8.55(1H, m), 8.46(2H, m), 8.27~8.30(5H, m), 8.23(1H, s), 7.98~8.12(5H, m), 7.85(2H, d), 7.79( 2H, d), 7.64(1H, t), 7.41~7.52(10H, m) 272 δ=8.55(1H, m), 8.46~8.55(2H, m), 8.23(1H, d), 7.98~8.10(4H, m), 7.85(2H, d), 7.79(4H, d), 7.41~ 7.66(12H, m), 7.25(2H, d) 275 δ=8.55(1H, m), 8.46(2H, m), 8.28~8.30(4H, m), 8.23(1H, s), 8.21(1H, d), 7.98~8.10(4H, m), 7.79( 2H, d), 7.41~7.66(12H, m), 7.25(2H, d) 277 δ=8.55(1H, m), 8.46(2H, m), 8.21~8.30(8H, m), 7.98~8.10(4H, m), 7.85(2H, d), 7.41~7.66(14H, m) 283 δ=8.55(1H, m), 8.45(2H, m), 8.21~8.23(2H, d), 7.98~8.10(4H, m), 7.79~7.90(5H, m), 7.41~7.64(13H, m) ) 285 δ=8.55(1H, m), 8.45(2H, m), 8.21~8.23(2H, d), 7.98~8.10(4H, m), 7.79~7.90(7H, m), 7.41~7.64(11H, m) ) 287 δ=8.55(1H, m), 8.45(2H, m), 8.23~8.30(6H, m), 7.98~8.10(4H, m), 7.79~7.90(5H, m), 7.41~7.64(11H, m) ) 302 δ=8.81(2H, d), 8.55(1H, m), 8.42(2H, m), 8.23~8.27(2H, d), 7.98~8.12(5H, m), 7.79~7.85(6H, m), 7.50~7.61(11H, m) 312 δ=8.93(2H, d), 8.44(2H, d), 8.23~8.30(6H, m), 8.12(3H, d), 7.98~8.03(2H, m), 7.79~7.88(8H, m), 7.41~7.52(8H, m) 318 δ=8.93(2H, d), 8.44(2H, d), 8.21~8.23(2H, d), 8.12(2H, d), 7.98~8.02(2H, m), 7.79~7.88(10H, m), 7.66(1H, t), 7.41~7.52(8H, m), 7.25(2H, d) 328 δ=8.93(2H, d), 8.45(2H, d), 8.21~8.23(2H, d), 8.12(2H, d), 8.04(1H, d), 7.79~7.90(12H, m), 7.41~ 7.52(8H, m), 7.25(2H, m) 332 δ=8.93(2H, d), 8.45(2H, d), 8.21~8.30(8H, m), 8.12(2H, d), 8.04(1H, d), 7.98(1H, m), 7.82~7.90( 9H, m), 7.41~7.52(10H, m) 342 δ=8.93(2H, d), 8.81(2H, d), 8.81(1H, m), 8.27(1H, s), 8.23(1H, s), 8.12(3H, d), 7.79~8.03(13H, m), 7.41~7.52(8H, m), 7.25~7.28(4H, t) 346 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, m), 8.21~8.30(7H, m), 8.12(3H, d), 7.98~8.03( 2H, m), 7.82~7.88(6H, m), 7.41~7.52(10H, m) 348 δ=8.93(2H, d), 8.55(1H, d), 8.45(1H, m), 8.23~8.30(7H, m), 8.12(3H, d), 7.98~8.03(2H, m), 7.79~ 7.88(8H, m), 7.41~7.52(8H, m) 355 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, d), 8.23(1H, s), 8.21(2H, d), 8.12(2H, d) , 8.04(1H, d), 7.98(1H, m), 7.79~7.90(11H, m), 7.41~7.52(8H, m) 358 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, d), 8.30(2H, t), 8.28(2H, d), 8.23(1H, d) , 8.21(2H, d), 8.12(2H, d), 8.04(1H, d), 7.98(1H, d), 7.82~7.90(7H, m), 7.41~7.52(10H, m) 359 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, d), 8.21~8.23(3H, t), 8.12(2H, d), 8.04(1H, d), 7.79~7.98(12H, m), 7.41~7.52(8H, m), 7.25(2H, d) 368 δ=8.55(1H, d), 8.45(1H, d), 8.23~8.30(4H, m), 8.12(2H, d), 8.03(1H, d), 7.94~7.98(2H, m), 7.79( 4H, d), 7.25~7.68(15H, m) 370 δ=8.45(1H, d), 8.23~8.30(6H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.79~7.89(5H, m), 7.66(1H, d), 7.25~7.54(13H, m) 372 δ=8.41~8.45(3H, m), 8.20~8.30(7H, m), 8.12(1H, d), 7.98~8.03(3H, m), 7.79(2H, d), 7.41~7.58(11H, m) ), 7.25(2H, d) 387 δ=8.27~8.30(9H, m), 8.23(1H, s), 8.12(1H, d), 8.03(1H, d), 7.85~7.89(5H, m), 7.66(1H, d), 7.41~ 7.54(13H, m) 394 δ=8.30(2H, d), 8.23(1H, s), 8.21(1H, d), 8.02(1H, d), 7.79~7.89(7H, m), 7.66(2H, m), 7.25~7.54( 13H, m) 403 δ=8.28~8.30(4H, m), 8.04(1H, d), 7.89~7.90(2H, d), 7.79(2H, d), 7.66(1H, d), 7.32~7.54(11H, m) 406 δ=8.30(2H, d), 8.21~8.23(2H, d), 8.04(1H, d), 7.79~7.90(8H, m), 7.66(1H, d), 7.41~7.54 (11H, m), 7.25(2H, d) 415 δ=8.28~8.30(4H, m), 8.23(1H, s), 7.89~8.03(4H, m), 7.79(2H, d), 7.66(1H, d), 7.32~7.66(11H, m) 418 δ=8.30(2H, d), 8.23(1H, s), 7.79~8.03(10H, m), 7.66(1H, d), 7.41~7.54(11H, m), 7.25(2H, d) 427 δ=8.55(1H, t), 8.46(1H, d), 8.28(2H, d), 8.27(1H, s), 8.23(1H, s), 8.03~8.12(4H, m), 7.89(1H, d), 7.79(2H, d), 7.32~7.66(12H, m) 432 δ=8.55(1H, t), 8.46(1H, d), 8.27~8.30(5H, m), 8.23(1H, s), 8.03~8.12(4H, m), 7.79~7.85(5H, m), 7.41~7.66(12H, m) 447 δ=8.55(1H, t), 8.46(1H, d), 8.21~8.23(2H, d), 8.04~8.10(3H, m), 7.89~7.90(2H, m), 7.79(3H, d), 7.41~7.66(12H, m) 453 δ=8.55(1H, t), 8.46(1H, d), 8.21~8.23(2H, d), 8.04~8.10(3H, m), 7.79~7.90(8H, m), 7.41~7.66(12H, m) ), 7.25(2H, d) 458 δ=8.55(1H, t), 8.46(1H, d), 8.30(4H, d), 8.21~8.23(2H, d), 8.04~8.10(3H, m), 7.85~7.90(8H, m), 7.64~7.66(2H, m), 7.32~7.55(14H, m), 7.25(2H, d) 473 δ=8.93(2H, d), 8.44(1H, s), 8.23~8.28(4H, m), 8.12(3H, d), 8.03(1H, d), 7.79~7.89(7H, m), 7.66( 1H, d), 7.32~7.51(8H, m) 476 δ=8.93(2H, d), 8.44(1H, s), 8.27(1H, s), 8.23(1H, s), 8.12(3H, d), 8.03(1H, d), 7.79~7.88(11H, m), 7.66(1H, d), 7.32~7.51(8H, m), 7.25(2H, d) 490 δ=8.93(2H, d), 8.44(1H, s), 8.21~8.23(2H, d), 8.12(2H, d), 8.04(1H, d), 7.79~7.90(10H, m), 7.66( 1H,d), 7.32~7.51(8H, m) 497 δ=8.93(2H, d), 8.44(1H, s), 8.21~8.23(2H, d), 8.12(2H, d), 8.04(1H, d), 7.9~7.60(12H, m), 7.66( 1H,d), 7.32~7.51(8H, m), 7.25(2H, d) 505 δ=8.93(2H, d), 8.44(1H, s), 8.30(2H, d), 8.23(1H, s), 8.12(2H, d), 7.82~7.95(12H, m), 7.66(1H, d), 7.32~7.52(12H, m), 7.25(2H, d) 509 δ=8.93(2H, d), 8.44(1H, s), 8.23~8.30(7H, m), 8.12(2H, d), 7.82~7.95(10H, m), 7.66(1H, d), 7.32~ 7.52(10H, m), 7.25(2H, d) 512 δ=8.93(2H, d), 8.81(2H, d), 8.37(1H, d), 8.28(2H, d), 8.23(1H, s), 8.12(2H, d), 8.02(1H, d) , 7.79~7.89(8H, m), 7.66(2H, m), 7.28~7.51(10H, m) 517 δ=8.93(2H, d), 8.55(1H, d), 8.27(1H, s), 8.23(1H, s), 8.21(1H, s), 8.12(2H, d), 8.03(1H, d) , 7.79~7.89(11H, m), 7.66(1H, d), 7.25~7.51(10H, m) 527 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.23(1H, s), 8.21(2H, s), 8.12(2H, d), 8.04(1H, d) , 7.79~7.89(12H, m), 7.66(1H, d), 7.32~7.51(8H, m), 7.25(2H, d) 534 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.27(1H, s), 8.23(1H, s), 8.27(1H, s), 8.12(3H, d) , 8.03~8.06(2H, d), 7.79~7.89(8H, m), 7.51~7.61(6H, m), 7.28~7.41(5H, m) 536 δ=8.55(1H, d), 8.23~8.30(5H, m), 8.03~8.12(4H, m), 7.89~7.94(2H, m), 7.79(2H, d), 7.29~7.66(16H, m) ) 537 δ=8.30(4H, d) 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 8.03(1H, d), 7.79~7.89(6H, m), 7.66(2H, d) ), 7.32~7.54(11H, m), 7.25(2H, d) 539 δ=8.41~8.45(2H, m), 8.30(4H, t), 8.27(1H, s), 8.23(1H, s), 8.20(1H, d), 8.12(1H, d), 7.98~8.03( 2H, m), 7.89(1H, d), 7.79(2H, d), 7.66(1H, d), 7.32~7.58(11H, m), 7.25(2H, d) 542 δ=9.30(2H, d), 9.15(2H, s), 8.53(2H, d), 8.45(1H, d), 8.27~8.30(3H, m), 8.12(1H, d), 7.98~8.03( 2H, m), 7.70(2H, m), 7.47~7.54(5H, m), 7.25(4H, s), 7.14(2H, t) 543 δ=9.30(2H, d), 9.15(2H, s), 8.53(2H, d), 8.45(1H, d), 8.30(2H, d), 8.27(1H, s), 8.12(1H, d) , 7.98~8.03(2H, m), 7.70(2H, m), 7.47~7.54(5H, m), 7.25(8H, s), 7.14(2H, t) 547 δ=9.30(2H, d), 9.15(2H, s), 8.53~8.55(3H, m), 8.45(2H, d), 8.27(1H, s), 7.98~8.12(5H, m), 7.50~ 7.55(4H, m), 7.64~7.70(3H, m), 7.25(4H, s), 7.14(2H, t) 551 δ=9.30(2H, d), 9.15(2H, s), 8.93(2H, d), 8.53(2H, d), 8.12(1H, d), 8.27(1H, s), 8.12(3H, d) , 7.98~8.03(2H, m), 7.82~7.88(4H, m), 7.70(2H, t), 7.50~7.52(2H, m), 7.25(4H, s), 7.14(2H, t) 555 δ=9.66(1H, s), 9.30(2H, d), 9.15(2H, s), 8.93(2H, d), 8.45~8.55(4H, m), 8.271H, s), 8.21(1H, d) ), 8.12(3H, d), 7.98~8.03(2H, m), 7.82~7.88(4H, m), 7.70(2H, t), 7.50~7.52(2H, m), 7.25(4H, s), 7.14(2H, t) 561 δ=9.30(2H, d), 9.15(2H, d), 8.53(2H, d), 8.30(2H, d), 8.21(1H, d), 8.02(1H, d), 7.89(1H, d) , 7.66~7.70(4H, m), 7.32~7.54(5H, m), 7.25(4H, s), 7.14(2H, t) 567 δ=9.30(2H, d), 9.15(2H, s), 8.93(2H, d), 8.53(2H, d), 8.44(1H, s), 8.27(1H, s), 8.12(3H, d) , 8.03(1H, d), 7.82~7.88(5H, m), 7.66~7.70(3H, m), 7.32~7.38(2H, m), 7.25(4H, s), 7.14(2H, t) 571 δ=9.66(1H, s), 9.30(2H, d), 9.15(2H, s), 8.93(2H, d), 8.53~8.55(3H, m), 8.27(1H, s), 8.21(1H, d), 8.12(3H, d), 8.03(1H, d), 7.82~7.89(5H, m), 7.66~7.70(3H, m), 7.32~7.38(2H, m), 7.25(4H, s) , 7.14(2H, t) 574 δ=8.81(2H, d), 8.45(1H, m), 8.27~8.28(5H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.88(2H, d), 7.41~ 7.52(13H, m) 575 δ=8.81(2H, d), 8.45(1H, m), 8.27~8.28(5H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.85~7.88(4H, t), 7.41~7.52(13H, m), 7.25(2H, d) 585 δ=8.45(1H, m), 8.21~8.30(8H, m), 8.04(1H, d), 7.98(1H, m), 7.90(1H, s), 7.60(1H, t), 7.41~7.52( 13H, m) 591 δ=8.81(2H, d), 8.46(1H, m), 8.28(2H, d), 7.87~8.06(8H, m), 7.79(2H, d), 7.38~7.52(12H, m), 7.28( 1H, t), 1.72(6H, s) 594 δ=8.81(2H, d), 8.55(1H, t), 8.42~8.45(2H, m), 8.25~8.28(3H, d), 7.98~8.12(5H, m), 7.85~7.88(4H, t) ), 7.41~7.61(13H, m), 7.25(2H, d) 607 δ=8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.28(4H, d), 8.21(1H, d), 8.12(2H, d), 7.82~8.02(9H, m), 7.66(1H, t), 7.41~7.52(8H, m) 610 δ=9.15(1H, s), 8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.27~8.28(5H, d), 8.18(1H, d), 8.12(3H, d), 7.98~8.04(3H, m), 7.82~7.88(6H, m), 7.41~7.52(8H, m) 614 δ=9.15(1H, s), 8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.28(4H, d), 8.21(1H, d), 8.18(1H, d) , 8.12(2H, d), 7.82~8.04(10H, m), 7.41~7.52(8H, m) 618 δ=8.81(2H, d), 8.45(1H, m), 8.27~8.28(5H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.81~7.89(5H, m), 7.66(1H, d), 7.32~7.52(11H, m) 621 δ=8.81(2H, d), 8.45(1H, m), 8.21~8.28(5H, d), 7.98~8.02(2H, m), 7.81~7.89(5H, m), 7.66(1H, m), 7.32~7.52(11H, m) 627 δ=8.81(2H, d), 8.45(1H, m), 8.28(4H, d), 7.85~7.95(9H, m), 7.66(1H, d), 7.32~7.52(11H, m) 634 δ=8.81(2H, d), 8.41~8.45(3H, m), 8.27~8.28(5H, d), 8.20(1H, d), 7.98~8.03(3H, m), 7.88(2H, d), 7.41~7.58(11H, m) 643 δ=8.81(2H, d), 8.41~8.45(3H, m), 8.28(4H, d), 8.20(1H, d), 7.88~7.98(7H, m), 7.41~7.58(11H, m) 650 δ=8.81(2H, d), 8.55(1H, d), 8.45(1H, m), 8.27~8.28(3H, d), 8.12(2H, d), 7.88~8.03(5H, m), 7.79( 2H, d), 7.63~7.68(3H, m), 7.25~7.52(14H, m) 652 δ=8.81(2H, d), 8.45(1H, m), 8.27~8.28(3H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.81~7.88(7H, m), 7.66(1H, d), 7.25~7.52(15H, m) 657 δ=8.81(2H, d), 8.27~8.28(5H, d), 8.12(1H, d), 8.03(1H, d), 7.85~7.88(5H, m), 7.66(1H, d), 7.32~ 7.52(13H, m), 7.25(2H, d) 667 δ=8.21~8.30(8H, m), 8.04(1H, d), 7.90(2H, d), 7.32~7.60(15H, m) 674 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 8.25~8.28(5H, d), 8.04~8.12(4H, m), 7.88~7.89(3H, d), 7.32~7.66(12H, m) 684 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 7.85~8.08(12H, m), 7.32~7.61(16H, m), 7.25(4H, d) 687 δ=8.93(2H, d), 8.81(2H, d), 8.21(1H, s), 8.12(3H, d), 8.03(1H, d), 7.82~7.93(12H, m), 7.66(1H, d), 7.32~7.52(12H, m), 7.25(4H, d) 692 δ=8.93(2H, d), 8.81(2H, d), 8.28(4H, d), 8.21(1H, d), 8.12(2H, d), 8.04(1H, d), 7.82~7.93(9H, m), 7.66(1H, d), 7.32~7.51(8H, m) 695 δ=8.93(2H, d), 8.81(2H, d), 8.28(4H, d), 8.12(2H, d), 7.82~8.03(11H, m), 7.66(1H, d), 7.32~7.51( 8H, m) 700 δ=9.15(1H, s), 8.93(2H, d), 8.81(2H, d), 8.28(4H, d), 8.18(1H, d), 8.12(2H, d), 8.02~8.04(2H, m), 7.82~7.88(7H, m), 7.66(1H, m), 7.32~7.51(8H, m) 708 δ=8.27~8.30(8H, m), 8.12(1H, d), 8.03(1H, d), 7.81~7.89(4H, m), 7.32~7.66(14H, m) 723 δ=8.81(2H, d), 8.41~8.45(2H, m), 8.27~8.28(3H, d), 8.20(1H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.85~7.88(5H, m), 7.66(1H, d), 7.32~7.58(15H, m) 729 δ=8.41~8.45(2H, m), 8.20~8.28(9H, m), 7.98~8.04(2H, m), 7.89~7.90(2H, d), 7.32~7.66(13H, m) 734 δ=8.81(2H, d), 8.41~8.45(2H, m), 8.28(4H, d), 8.27(1H, s), 8.20(1H, d), 7.98~8.03(2H, m), 7.88( 3H, d), 7.32~7.70(16H, m) 737 δ=8.81(2H, d), 8.55(1H, d), 8.27(3H, d), 8.12(2H, d), 8.03(1H, d), 7.88~7.94(4H, m), 7.79(2H, d), 7.63~7.68(4H, m), 7.29~7.52(14H, m) 739 δ=8.81(2H, d), 8.28(3H, d), 8.12(1H, d), 8.03(1H, d), 7.81~7.88(8H, m), 7.66(2H, d), 7.25~7.52( 15H, m) 741 δ=8.81(2H, d), 8.41~8.45(2H, m), 8.27~8.28(3H, d), 8.20(1H, d), 8.12(1H, d), 7.98~8.03(2H, m), 7.85~7.88(5H, m), 7.25~7.52(16H, m) 744 δ=8.81(2H, d), 8.45(1H, m), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.79~7.88( 8H, m), 7.41~7.52(13H, m), 7.25(2H, d) 746 δ=8.81(2H, d), 8.45(1H, d), 8.30(4H, d), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.85(4H, d), 7.88(2H, d), 7.41~7.52(17H, m) 758 δ=8.81(2H, d), 8.45(1H, m), 8.21~8.33(6H, m), 7.98(1H, d), 8.04(1H, d), 7.90(1H, s), 7.79(2H, d), 7.41~7.52(13H, m) 768 δ=8.81(2H, d), 8.55(1H, m), 8.45(2H, m), 8.23(2H, d), 7.98~8.12(5H, m), 7.88(2H, d), 7.79(4H, d), 7.41~7.61(11H, m) 781 δ=8.81(2H, d), 8.55(1H, m), 8.42(2H, m), 8.23(1H, s), 7.94~8.08(6H, m), 7.88(2H, d), 7.79(4H, d), 7.41~7.61(11H, m) 789 δ=8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.23~8.33(6H, m), 8.12(3H, d), 7.79~8.03(9H, m), 7.41~ 7.52(8H, m) 796 δ=8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.21~8.23(2H, d), 8.12(2H, d), 8.04(1H, d), 7.79~7.93( 13H, m), 7.41~7.52(8H, m) 802 δ=8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 8.23~8.33(5H, m), 8.12(2H, d), 7.79~8.03(11H, m), 7.41~ 7.52(8H, m) 804 δ=8.93(2H, d), 8.46(1H, m), 8.21~8.28(5H, m), 8.12(2H, d), 7.79~7.98(12H, m), 7.41~7.60(9H, m) 807 δ=9.15(1H, s), 8.93(2H, d), 8.81(2H, d), 8.45(1H, m), 7.98~8.33(13H, m), 7.79~7.88(6H, m), 7.41~ 7.52(8H, m) 813 δ=8.81(2H, d), 8.46(1H, m), 8.23~8.33(6H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.79~7.89(5H, m), 7.66(1H, d), 7.32~7.52(11H, m) 818 δ=8.81(2H, d), 8.41~8.81(3H, m), 8.20~8.33(7H, m), 8.12(1H, d), 7.98~8.03(3H, m), 7.79(2H, d), 7.41~7.58(11H, m) 824 δ=8.81(2H, d), 8.55(1H, d), 8.45(1H, m), 8.33(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(2H, d) , 7.94~8.03(3H, m), 7.79(4H, d), 7.63~7.68(3H, m), 7.25~7.52(14H, m) 826 δ=8.81(2H, d), 8.45(1H, m), 8.33(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 7.98~8.03(2H, m), 7.79~7.89(7H, m), 7.66(1H, d), 7.25~7.52(15H, m) 830 δ=8.81(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 8.03(1H, d), 7.88~7.89(3H, m), 7.79(4H, d), 7.66(1H, d), 7.32~7.52(13H, m) 831 δ=8.81(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 8.03(1H, d), 7.79~7.88(9H, m), 7.66(1H, d), 7.32~7.52(13H, m), 7.25(2H, d) 844 δ=8.81 (2H, d), 8.21~8.33(6H, m), 8.04(1H, d), 7.89~7.90(2H, d), 7.79(2H, m), 7.66(1H, d), 7.32~ 7.52(13H, m) 855 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 8.28(1H, s), 8.23(1H, s), 8.03~8.12(4H, m), 7.88(3H, m), 7.79(4H, d), 7.32~7.55(12H, m) 861 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 8.21~8.28(6H, m), 8.02~8.08(3H, m), 7.89(1H, d), 7.79( 2H, d), 7.32~7.66(13H, m) 877 δ=8.93(2H, d), 8.81(2H, d), 8.28~8.33(8H, m), 8.12(3H, d), 8.03(1H, d), 7.82~7.93(8H, m), 7.66( 1H, d), 7.32~7.51(10H, m) 883 δ=8.93(2H, d), 8.81(2H, d), 8.21~8.23(2H, d), 8.12(2H, d), 8.04(1H, d), 7.79~7.93(13H, m), 7.66( 1H, d), 7.32~7.51(8H, m) 894 δ=9.15(1H, s), 8.93(2H, d), 8.81(2H, d), 8.33(2H, m), 8.28(2H, d), 8.27(1H, s), 8.23(1H, s) , 8.03~8.12(6H, m), 7.79~7.88(7H, m), 7.66(1H, d), 7.32~7.51(8H, m) 902 δ=8.81(2H, d), 8.27~8.33(6H, m), 8.12(1H, d), 8.03(1H, d), 7.79~7.89(6H, m), 7.66(2H, d), 7.32~ 7.51(11H, m) 907 δ=8.81(2H, d), 8.21~8.33(6H, m), 8.02(1H, d), 7.79~7.89(6H, m), 7.66(3H, m), 7.32~7.51(11H, m) 910 δ=8.81(2H, d), 8.45(1H, m), 8.20~8.41(8H, m), 8.12(1H, d), 7.98~8.03(2H, m), 7.89(1H, d), 7.79( 2H, d), 7.66(1H, d), 7.32~7.58(11H, m) 917 δ=9.66(1H, s), 8.93(2H, d), 8.55(1H, d), 8.45(1H, m), 8.27(1H, s), 8.21(1H, s), 8.12(3H, d) , 7.98~8.03(2H, m), 7.77~7.88(21H, m), 7.45~7.52(8H, m) 918 δ=8.81(2H, d), 8.55(1H, d), 8.12(1H, d), 7.88~8.03(7H, m), 7.79(4H, d), 7.63~7.66(2H, t), 7.29~ 7.51(13H, m) 919 δ=8.81(2H, d), 8.23(1H, s), 8.06(1H, m), 8.23(1H, d), 7.94~7.95(2H, m), 7.79~7.87(6H, d), 7.28~ 7.66(14H, m), 1.72(6H, s) 920 δ=8.81(2H, d), 8.55(1H, d), 8.33(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(2H, d), 8.03(1H, d) , 7.89~7.94(2H, m), 7.79(4H, d), 7.63~7.68(4H, m), 7.25~7.52(14H, m) 923 δ=8.81(2H, d), 8.27(1H, s), 8.23(1H, s), 8.12(1H, d), 8.03(1H, d), 7.66~7.89(12H, m), 7.32~7.57( 15H, m) 926 δ=8.81(2H, d), 8.51(1H, d), 8.45(1H, d), 8.28(4H, d), 8.16(1H, d), 8.06(1H, d), 7.98(1H, d) , 7.88(2H, d), 7.81(1H, d), 7.67(2H, t), 7.41~7.52(8H, m) 927 δ=8.45~8.55(3H, m), 8.28~8.30(3H, m), 8.12~8.26(4H, m), 8.06(1H, d), 7.94~7.98(2H, m), 7.81~7.79(3H) , m), 7.67~7.68(4H, m), 7.60(1H, m), 7.50~7.52(6H, m), 7.25~7.41(3H, m) 928 δ=8.81(2H, d), 8.51(1H, t), 8.46(1H, m), 8.24~8.28(3H, m), 8.16(1H, d), 8.06(1H, d), 7.98(1H, m), 7.81~7.89(6H, m), 7.66~7.70(4H, m), 7.32~7.57(10H, m) 932 δ=8.81(2H, d), 8.51(1H, d), 8.45(2H, m), 8.41(1H, d), 8.28(2H, d), 8.20(1H, d), 8.16(1H, m) , 8.06(1H, d), 7.98(2H, d), 7.81~7.88(5H, m), 7.67(2H, m), 7.41~7.58(8H, m), 7.25(2H, d) 936 δ=9.30(2H, d), 9.15(2H, s), 8.81(2H, d), 8.45~8.53(4H, m), 8.16(1H, m), 8.06(1H, d), 7.98(1H, m), 7.88(2H, d), 7.81(1H, d), 7.67~7.70(4H, m), 7.50~7.52(2H, m), 7.25(4H, s), 7.14(1H, t) 937 δ=8.81(2H, d), 8.51(1H, m), 8.45(1H, m), 8.15(1H, m), 8.06(1H, d), 7.98(1H, d), 7.88(2H, d) , 7.66~7.81(9H, m), 7.45~7.52(10H, m) 943 δ=8.51~8.55(2H, m), 8.28~8.30(4H, m), 8.26(1H, s), 8.06~8.21(4H, m), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d), 7.66~7.67(3H, m), 7.25~7.63(12H, m) 945 δ=8.51(1H, t), 8.30(2H, d), 8.16~8.26(4H, m), 8.06(1H, d), 7.85~7.89(5H, m), 7.66~7.67(3H, m), 7.54~7.60(3H, m), 7.51~7.52(8H, m), 7.32~7.41(4H, m) 950 δ=8.81(2H, d), 8.45(1H, m), 8.28(4H, t), 8.16(2H, m), 8.05(1H, s), 7.98(1H, m), 7.88(2H, d) , 7.67~7.68(3H, m), 7.50~7.52(6H, m), 7.41(2H, m) 952 δ=8.81(2H, d), 8.45(1H, m), 8.28(2H, m), 8.24(1H, m), 8.16(2H, m), 8.05(1H, s), 7.98(1H, d) , 7.81~7.89(5H, m), 7.70(1H, s), 7.66~7.68(4H, m), 7.50~7.52(4H, m), 7.32~7.48(4H, m) 954 δ=8.81(2H, d), 8.45(1H, m), 8.33(2H, d), 8.23(1H, d), 8.16(2H, m), 8.05(1H, s), 7.98(1H, d) , 7.85(2H, d), 7.79(2H, d), 7.67~7.68(2H, m), 7.50~7.52(8H, m), 7.41(2H, m), 7.25(2H, d) 956 δ=8.81(2H, d), 8.41~8.45(3H, m), 8.28(2H, d), 8.16~8.20(3H, m), 8.05(1H, s), 7.98(2H, d), 7.88( 2H, d), 7.85(2H, d), 7.68(1H, m), 7.67(2H, d), 7.50~7.53(7H, m), 7.41(1H, m), 7.25(2H, d) 959 δ=8.81(2H, d), 8.45(1H, m), 8.23(1H, s), 8.16(2H, m), 8.05(1H, s), 7.79~7.98(6H, m), 7.50~7.75( 9H, m), 7.32~7.48(5H, m) 961 δ=8.81(2H, d), 8.45(1H, m), 8.16(2H, m), 8.05(1H, s), 7.98(1H, m), 7.88(2H, d), 7.66~7.68(4H, m), 7.73~7.77(4H, m), 7.50~7.52(4H, m), 7.45(5H, m) 962 δ=8.81(2H, d), 8.28(4H, m), 8.16(2H, m), 8.05(1H, s), 7.88~7.89(3H, m), 7.67~7.68(3H, m), 7.51( 4H, m), 7.41(2H, m), 7.32~7.38(2H, m) 969 δ=8.30(2H, d), 8.21~8.26(3H, m), 8.05(1H, s), 7.89(1H, d), 7.85(4H, d), 7.32~7.75(22H, m), 7.25( 2H, d) 971 δ=8.81(2H, d), 8.23(1H, s), 8.16(2H, m), 8.05(1H, s), 7.81~7.89(8H, m), 7.66~7.79(9H, m), 7.32~ 7.51(7H, m) 977 δ=8.54(1H, m), 8.45(1H, m), 8.16~8.28(6H, m), 7.98~7.99(3H, m), 7.85(2H, d), 7.41~7.67(17H, m), 7.25(2H, d) 978 δ=8.81(2H, d), 8.54(1H, m), 8.45(1H, m), 8.33(2H, d), 8.23(1H, s), 8.16(1H, m), 7.98~7.99(2H, m), 7.85(2H, d), 7.79(2H, d), 7.67(2H, m), 7.50~7.52(8H, m), 7.41(2H, m), 7.25(2H, d) 980 δ=8.81(2H, d), 8.54(1H, m), 8.41~8.45(3H, m), 8.28(2H, m), 8.16~8.20(2H, d), 7.98~7.99(4H, m), 7.88(2H, d), 7.85(2H, d), 7.67(2H, m), 7.58(1H, s), 7.50~7.52(6H, m), 7.41(1H, m), 7.25(2H, d) 986 δ=8.81(2H, d), 8.54(1H, m), 8.28(4H, m), 8.16(1H, m), 7.89~7.99(2H, s), 7.88~7.89(3H, m), 7.66~ 7.67(3H, m), 7.51(4H, m), 7.41(2H, m), 7.32~7.38(2H, m) 990 δ=8.81(2H, d), 8.54(1H, m), 8.33(2H, d), 8.16(1H, m), 7.89~7.99(2H, s), 7.79~7.89(5H, m), 7.66~ 7.67(3H, m), 7.51~7.52(6H, m), 7.32~7.41(4H, m), 7.25(2H, d) 996 δ=9.30(2H, d), 9.15(2H, s), 8.81(2H, d), 8.53~8.54(3H, m), 8.16(1H, m), 7.98~7.99(2H, s), 7.88~ 7.89(2H, d), 7.66~7.70(5H, m), 7.32~7.38(2H, m), 7.25(4H, s), 7.14(2H, t) 998 δ=8.81(2H, d), 8.45(1H, m), 8.27~8.30(5H, m), 7.98~8.12(6H, m), 7.88(2H, d), 7.81(1H, d), 7.47~ 7.54(8H, m), 7.35(2H, d) 999 δ=8.81(2H, d), 8.55(1H, m), 8.45~8.46(2H, m), 8.30(2H, d), 8.21(1H, d), 7.98~8.10(7H, m), 7.81( 1H, d), 7.64~7.66(2H, m), 7.47~7.55(7H, m), 7.35(2H, d), 7.28(2H, d) 1002 δ=8.81(4H, d), 8.45(1H, d), 8.27~8.30(3H, m), 7.98~8.12(6H, m), 7.88(4H, d), 7.81(1H, d), 7.47~ 7.54(9H, m), 7.35~7.41(3H, m) 1003 δ=8.81(4H, d), 8.55(1H, m), 8.45(2H, m), 8.30(2H, d), 8.21(1H, d), 7.98~8.10(7H, d), 7.81(1H, d), 7.50~7.66(9H, m), 7.35(2H, d), 7.28(4H, d) 1008 δ=8.93(2H, d), 8.81(2H, d), 8.44(1H, s), 8.30(2H, d), 8.21(1H, d), 8.04~8.12(6H, m), 7.81~7.90( 9H, m), 7.66(1H, d), 7.32~7.54(7H, m) 1012 δ=8.81(2H, d), 8.21~8.30(5H, m), 8.04~8.10(4H, m), 7.88~7.90(4H, d), 7.81(1H, d), 7.32~7.66(15H, m) ) 1013 δ=8.81(2H, d), 8.55(1H, m), 8.42(1H, d), 8.24~8.30(4H, m), 7.89~8.10(8H, m), 7.81(1H, d), 7.28~ 7.66(15H, m) 1014 δ=8.84(4H, s), 8.45(1H, m), 8.27~8.30(3H, m), 7.98~8.12(6H, m), 7.81(1H, d), 7.47~7.54(9H, m), 7.35~7.41(3H, d) 1016 δ=8.93(2H, d), 8.84(4H, s), 8.45(1H, m), 8.30(2H, d), 8.21(1H, d), 7.81~8.12(14H, m), 7.47~7.54( 5H, m), 7.35(2H, d) 1018 δ=8.84(4H, s), 8.45(4H, m), 8.27~8.60(3H, m), 7.98~8.12(6H, m), 7.81~7.89(4H, m), 7.66(1H, m), 7.32~7.54(10H, m) 1019 δ=8.84(4H, s), 8.41~8.45(3H, m), 8.30(2H, d), 8.20(1H, m), 7.98~8.10(6H, m), 7.81(1H, d), 7.47~ 7.66(9H, m), 7.35(2H, d) 1020 δ=8.84(4H, s), 8.45(1H, m), 8.51(1H, m), 8.30(2H, d), 7.98~8.10(6H, m), 7.81(2H, d), 7.67(2H, m), 7.47~7.54(5H, m), 7.35(2H, d) 1022 δ=8.84(4H, s), 8.54(1H, m), 8.45(1H, m), 8.30(2H, d), 7.98~8.10(7H, m), 7.81(1H, d), 7.67(2H, m), 7.47~7.54(5H, m), 7.35(2H, d) 1024 δ=8.84(4H, s), 8.55(1H, m), 8.42(1H, d), 8.30(2H, d), 8.21(1H, d), 8.02~8.10(6H, m), 7.89(1H, d), 7.81(1H, d), 7.32~7.66(12H, m) 1026 δ=8.93(2H, d), 8.84(4H, s), 8.30(2H, d), 7.81~8.12(17H, m), 7.68(1H, d), 7.32~7.54(7H, m)

[Table 59] Compound FD-MS Compound FD-MS 1 m/z=542.65 (C36H22N4S=542.16) 2 m/z=618.75 (C42H26N4S=618.19) 3 m/z=694.84 (C48H30N4S=694.22) 4 m/z=618.75 (C42H26N4S=618.19) 5 m/z=694.84 (C48H30N4S=694.22) 6 m/z=694.84 (C48H30N4S=694.22) 7 m/z=770.94 (C54H34N4S=770.25) 8 m/z=694.84 (C48H30N4S=694.22) 9 m/z=770.94 (C54H34N4S=770.25) 10 m/z=618.75 (C42H26N4S=618.19) 11 m/z=542.65 (C36H22N4S=542.16) 12 m/z=694.84 (C48H30N4S=694.22) 13 m/z=618.75 (C42H26N4S=618.19) 14 m/z=694.84 (C48H30N4S=694.22) 15 m/z=770.94 (C54H34N4S=770.25) 16 m/z=618.75 (C42H26N4S=618.19) 17 m/z=770.94 (C54H34N4S=770.25) 18 m/z=542.65 (C36H22N4S=542.16) 19 m/z=618.75 (C42H26N4S=618.19) 20 m/z=694.84 (C48H30N4S=694.22) twenty one m/z=618.75 (C42H26N4S=618.19) twenty two m/z=694.84 (C48H30N4S=694.22) twenty three m/z=770.94 (C54H34N4S=770.25) twenty four m/z=618.75 (C42H26N4S=618.19) 25 m/z=770.94 (C54H34N4S=770.25) 26 m/z=542.65 (C36H22N4S=542.16) 27 m/z=618.75 (C42H26N4S=618.19) 28 m/z=694.84 (C48H30N4S=694.22) 29 m/z=618.75 (C42H26N4S=618.19) 30 m/z=694.84 (C48H30N4S=694.22) 31 m/z=770.94 (C54H34N4S=770.25) 32 m/z=618.75 (C42H26N4S=618.19) 33 m/z=770.94 (C54H34N4S=770.25) 34 m/z=663.76 (C45H30NOPS=663.18) 35 m/z=663.76 (C45H30NOPS=663.18) 36 m/z=592.71 (C40H24N4S=592.17) 37 m/z=668.81 (C46H28N4S=668.20) 38 m/z=668.81 (C46H28N4S=668.20) 39 m/z=744.90 (C52H32N4S=744.23) 40 m/z=668.81 (C46H28N4S=668.20) 41 m/z=821.00 (C58H36N4S=820.27) 42 m/z=592.71 (C40H24N4S=592.17) 43 m/z=668.81 (C46H28N4S=668.20) 44 m/z=668.81 (C46H28N4S=668.20) 45 m/z=744.90 (C52H32N4S=744.23) 46 m/z=668.81 (C46H28N4S=668.20) 47 m/z=821.00 (C58H36N4S=820.27) 48 m/z=592.71 (C40H24N4S=592.17) 49 m/z=668.81 (C46H28N4S=668.20) 50 m/z=668.81 (C46H28N4S=668.20) 51 m/z=744.90 (C52H32N4S=744.23) 52 m/z=821.00 (C58H36N4S=820.27) 53 m/z=668.81 (C46H28N4S=668.20) 54 m/z=542.65 (C36H22N4S=542.16) 55 m/z=618.75 (C42H26N4S=618.19) 56 m/z= 668.81 (C46H28N4S=668.20) 57 m/z=744.90 (C52H32N4S=744.23) 58 m/z=668.81 (C46H28N4S=668.20) 59 m/z=668.81 (C46H28N4S=668.20) 60 m/z=744.90 (C52H32N4S=744.23) 61 m/z=744.90 (C52H32N4S=744.23) 62 m/z=642.77 (C44H26N4S=642.19) 63 m/z=718.87 (C50H30N4S=718.22) 64 m/z=718.87 (C50H30N4S=718.22) 65 m/z=718.87 (C50H30N4S=718.22) 66 m/z=642.77 (C44H26N4S=642.19) 67 m/z=794.96 (C56H34N4S=794.25) 68 m/z=718.87 (C50H30N4S=718.22) 69 m/z=794.96 (C56H34N4S=794.25) 70 m/z=642.77 (C44H26N4S=642.19) 71 m/z=718.87 (C50H30N4S=718.22) 72 m/z=718.87 (C50H30N4S=718.22) 73 m/z=794.96 (C56H34N4S=794.25) 74 m/z=718.87 (C50H30N4S=718.22) 75 m/z=642.77 (C44H26N4S=642.19) 76 m/z=718.87 (C50H30N4S=718.22) 77 m/z=794.96 (C56H34N4S=794.25) 78 m/z=718.87 (C50H30N4S=718.22) 79 m/z=718.87 (C50H30N4S=718.22) 80 m/z=794.96 (C56H34N4S=794.25) 81 m/z=794.96 (C56H34N4S=794.25) 82 m/z=692.83 (C48H28N4S=692.20) 83 m/z=766.91 (C54H30N4S=766.22) 84 m/z=768.92 (C54H32N4S=768.23) 85 m/z=845.02 (C60H36N4S=844.27) 86 m/z=768.92 (C54H32N4S=768.23) 87 m/z=692.83 (C48H28N4S=692.20) 88 m/z=768.92 (C54H32N4S=768.23) 89 m/z=768.92 (C54H32N4S=768.23) 90 m/z=692.83 (C48H28N4S=692.20) 91 m/z=768.92 (C54H32N4S=768.23) 92 m/z=768.92 (C54H32N4S=768.23) 93 m/z=768.92 (C54H32N4S=768.23) 94 m/z=692.83 (C48H28N4S=692.20) 95 m/z=768.92 (C54H32N4S=768.23) 96 m/z=768.92 (C54H32N4S=768.23) 97 m/z=768.92 (C54H32N4S=768.23) 98 m/z=768.92 (C54H32N4S=768.23) 99 m/z=781.92 (C54H31N5S=781.23) 100 m/z=808.99 (C57H36N4S=808.27) 101 m/z=737.84 (C51H32NOPS=737.19) 102 m/z=526.59 (C36H22N4O=526.18) 103 m/z=602.68 (C42H26N4O=602.21) 104 m/z=678.78 (C48H30N4O=678.24) 105 m/z=602.68 (C42H26N4O=602.21) 106 m/z=678.78 (C48H30N4O=678.24) 107 m/z=678.78 (C48H30N4O=678.24) 108 m/z=754.87 (C54H34N4O=754.27) 109 m/z=678.78 (C48H30N4O=678.24) 110 m/z=754.87 (C54H34N4O=754.27) 111 m/z=526.59 (C36H22N4O=526.18) 112 m/z=602.68 (C42H26N4O=602.21) 113 m/z=678.78 (C48H30N4O=678.24) 114 m/z=602.68 (C42H26N4O=602.21) 115 m/z=678.78 (C48H30N4O=678.24) 116 m/z=754.87 (C54H34N4O=754.27) 117 m/z=602.68 (C42H26N4O=602.21) 118 m/z=754.87 (C54H34N4O=754.27) 119 m/z=526.59 (C36H22N4O=526.18) 120 m/z=602.68 (C42H26N4O=602.21) 121 m/z=678.78 (C48H30N4O=678.24) 122 m/z=602.68 (C42H26N4O=602.21) 123 m/z=678.78 (C48H30N4O=678.24) 124 m/z=754.87 (C54H34N4O=754.27) 125 m/z=602.68 (C42H26N4O=602.21) 126 m/z=754.87 (C54H34N4O=754.27) 127 m/z=526.59 (C36H22N4O=526.18) 128 m/z=602.68 (C42H26N4O=602.21) 129 m/z=678.78 (C48H30N4O=678.24) 130 m/z=602.68 (C42H26N4O=602.21) 131 m/z=678.78 (C48H30N4O=678.24) 132 m/z=754.87 (C54H34N4O=754.27) 133 m/z=602.68 (C42H26N4O=602.21) 134 m/z=754.87 (C54H34N4O=754.27) 135 m/z=647.70 (C45H30NO2P=647.20) 136 m/z=576.64 (C40H24N4O=576.20) 137 m/z=652.74 (C46H28N4O=652.23) 138 m/z=652.74 (C46H28N4O=652.23) 139 m/z=728.84 (C52H32N4O=728.26) 140 m/z=652.74 (C46H28N4O=652.23) 141 m/z=804.93 (C58H36N4O=804.29) 142 m/z=576.64 (C40H24N4O=576.20) 143 m/z=652.74 (C46H28N4O=652.23) 144 m/z=728.84 (C52H32N4O=728.26) 145 m/z=804.93 (C58H36N4O=804.29) 146 m/z=652.74 (C46H28N4O=652.23) 147 m/z=804.93 (C58H36N4O=804.29) 148 m/z=576.64 (C40H24N4O=576.20) 149 m/z=652.74 (C46H28N4O=652.23) 150 m/z=728.84 (C52H32N4O=728.26) 151 m/z=652.74 (C46H28N4O=652.23) 152 m/z=728.84 (C52H32N4O=728.26) 153 m/z=804.93 (C58H36N4O=804.29) 154 m/z=652.74 (C46H28N4O=652.23) 155 m/z=576.64 (C40H24N4O=576.20) 156 m/z=652.74 (C46H28N4O=652.23) 157 m/z=728.84 (C52H32N4O=728.26) 158 m/z=804.93 (C58H36N4O=804.29) 159 m/z=652.74 (C46H28N4O=652.23) 160 m/z=652.74 (C46H28N4O=652.23) 161 m/z=728.84 (C52H32N4O=728.26) 162 m/z=728.84 (C52H32N4O=728.26) 163 m/z=626.70 (C44H26N4O=626.21) 164 m/z=702.80 (C50H30N4O=702.24) 165 m/z=702.80 (C50H30N4O=702.24) 166 m/z=626.70 (C44H26N4O=626.21) 167 m/z=702.80 (C50H30N4O=702.24) 168 m/z=702.80 (C50H30N4O=702.24) 169 m/z=626.70 (C44H26N4O=626.21) 170 m/z=702.80 (C50H30N4O=702.24) 171 m/z=702.80 (C50H30N4O=702.24) 172 m/z=778.90 (C56H34N4O=778.27) 173 m/z=702.80 (C50H30N4O=702.24) 174 m/z=626.70 (C44H26N4O=626.21) 175 m/z=702.80 (C50H30N4O=702.24) 176 m/z=778.90 (C56H34N4O=778.27) 177 m/z=702.80 (C50H30N4O=702.24) 178 m/z=778.90 (C56H34N4O=778.27) 179 m/z=676.76 (C48H28N4O=676.23) 180 m/z=752.86 (C54H32N4O=752.26) 181 m/z=752.86 (C54H32N4O=752.26) 182 m/z=676.76 (C48H28N4O=676.23) 183 m/z=752.86 (C54H32N4O=752.26) 184 m/z=752.86 (C54H32N4O=752.26) 185 m/z=752.86 (C54H32N4O=752.26) 186 m/z=676.76 (C48H28N4O=676.23) 187 m/z=752.86 (C54H32N4O=752.26) 188 m/z=752.86 (C54H32N4O=752.26) 189 m/z=752.86 (C54H32N4O=752.26) 190 m/z=676.76 (C48H28N4O=676.23) 191 m/z=752.86 (C54H32N4O=752.26) 192 m/z=752.86 (C54H32N4O=752.26) 193 m/z=752.86 (C54H32N4O=752.26) 194 m/z=752.86 (C54H32N4O=752.26) 195 m/z=765.86 (C54H31N5O=765.25) 196 m/z=792.92 (C57H36N4O=792.29 197 m/z=721.78 (C51H32NO2P=721.22) 198 m/z=691.78 (C48H29N5O=691.24) 199 m/z=691.78 (C48H29N5O=691.24) 200 m/z=692.76 (C48H28N4O2=692.22) 201 m/z=692.76 (C48H28N4O2=692.22) 202 m/z=708.83 (C48H28N4OS=708.20) 203 m/z=708.83 (C48H28N4OS=708.20) 204 m/z=541.66 (C37H23N3S=541.16) 205 m/z=617.76 (C43H27N3S=617.19) 206 m/z=541.66 (C37H23N3S=541.16) 207 m/z=617.76 (C43H27N3S=617.19) 208 m/z=617.76 (C43H27N3S=617.19) 209 m/z=617.76 (C43H27N3S=617.19) 210 m/z=693.86 (C49H31N3S=693.22) 211 m/z=693.86 (C49H31N3S=693.22) 212 m/z=693.86 (C49H31N3S=693.22) 213 m/z=769.95 (C55H35N3S=769.26) 214 m/z=769.95 (C55H35N3S=769.26) 215 m/z=617.76 (C43H27N3S=617.19) 216 m/z=693.86 (C49H31N3S=693.22) 217 m/z=693.86 (C49H31N3S=693.22) 218 m/z=541.66 (C37H23N3S=541.16) 219 m/z=617.76 (C43H27N3S=617.19) 220 m/z=541.66 (C37H23N3S=541.16) 221 m/z=617.76 (C43H27N3S=617.19) 222 m/z=617.76 (C43H27N3S=617.19) 223 m/z=617.76 (C43H27N3S=617.19) 224 m/z=693.86 (C49H31N3S=693.22) 225 m/z=769.95 (C55H35N3S=769.26) 226 m/z=617.76 (C43H27N3S=617.19) 227 m/z=693.86 (C49H31N3S=693.22) 228 m/z=693.86 (C49H31N3S=693.22) 229 m/z=769.95 (C55H35N3S=769.26) 230 m/z=541.66 (C37H23N3S=541.16) 231 m/z=617.76 (C43H27N3S=617.19) 232 m/z=693.86 (C49H31N3S=693.22) 233 m/z=541.66 (C37H23N3S=541.16) 234 m/z=617.76 (C43H27N3S=617.19) 235 m/z=617.76 (C43H27N3S=617.19) 236 m/z=837.06 (C59H36N2S2=836.23) 237 m/z=693.86 (C49H31N3S=693.22) 238 m/z=769.95 (C55H35N3S=769.26) 239 m/z=617.76 (C43H27N3S=617.19) 240 m/z=693.86 (C49H31N3S=693.22) 241 m/z=693.86 (C49H31N3S=693.22) 242 m/z=769.95 (C55H35N3S=769.26) 243 m/z=617.76 (C43H27N3S=617.19) 244 m/z=617.76 (C43H27N3S=617.19) 245 m/z=541.66 (C37H23N3S=541.16) 246 m/z=617.76 (C43H27N3S=617.19) 247 m/z=617.76 (C43H27N3S=617.19) 248 m/z=617.76 (C43H27N3S=617.19) 249 m/z=693.86 (C49H31N3S=693.22) 250 m/z=769.95 (C55H35N3S=769.26) 251 m/z=617.76 (C43H27N3S=617.19) 252 m/z=693.86 (C49H31N3S=693.22) 253 m/z=693.86 (C49H31N3S=693.22) 254 m/z=769.95 (C55H35N3S=769.26) 255 m/z=733.92 (C52H35N3S=733.26) 256 m/z=591.72 (C41H25N3S=591.18) 257 m/z=667.82 (C47H29N3S=667.21) 258 m/z=591.72 (C41H25N3S=591.18) 259 m/z=667.82 (C47H29N3S=667.21) 260 m/z=667.82 (C47H29N3S=667.21) 261 m/z=667.82 (C47H29N3S=667.21) 262 m/z=743.91 (C53H33N3S=743.24) 263 m/z=820.01 (C59H37N3S=819.27) 264 m/z=667.82 (C47H29N3S=667.21) 265 m/z=743.91 (C53H33N3S=743.24) 266 m/z=743.91 (C53H33N3S=743.24) 267 m/z=855.03 (C63H42N4=854.34) 268 m/z=829.00 (C61H40N4=828.33) 269 m/z=591.72 (C41H25N3S=591.18) 270 m/z=667.82 (C47H29N3S=667.21) 271 m/z=667.82 (C47H29N3S=667.21) 272 m/z=667.82 (C47H29N3S=667.21) 273 m/z=743.91 (C53H33N3S=743.24) 274 m/z=820.01 (C59H37N3S=819.27) 275 m/z=667.82 (C47H29N3S=667.21) 276 m/z=743.91 (C53H33N3S=743.24) 277 m/z=743.91 (C53H33N3S=743.24) 278 m/z=820.01 (C59H37N3S=819.27) 279 m/z=591.72 (C41H25N3S=591.18) 280 m/z=667.82 (C47H29N3S=667.21) 281 m/z=743.91 (C53H33N3S=743.24) 282 m/z=591.72 (C41H25N3S=591.18) 283 m/z=667.82 (C47H29N3S=667.21) 284 m/z=667.82 (C47H29N3S=667.21) 285 m/z=667.82 (C47H29N3S=667.21) 286 m/z=743.91 (C53H33N3S=743.24) 287 m/z=667.82 (C47H29N3S=667.21) 288 m/z=743.91 (C53H33N3S=743.24) 289 m/z=743.91 (C53H33N3S=743.24) 290 m/z=591.72 (C41H25N3S=591.18) 291 m/z=667.82 (C47H29N3S=667.21) 292 m/z=591.72 (C41H25N3S=591.18) 293 m/z=667.82 (C47H29N3S=667.21) 294 m/z=667.82 (C47H29N3S=667.21) 295 m/z=743.91 (C53H33N3S=743.24) 296 m/z=820.01 (C59H37N3S=819.27) 297 m/z=667.82 (C47H29N3S=667.21) 298 m/z=743.91 (C53H33N3S=743.24) 299 m/z=743.91 (C53H33N3S=743.24) 300 m/z=820.01 (C59H37N3S=819.27) 301 m/z=667.82 (C47H29N3S=667.21) 302 m/z=743.91 (C53H33N3S=743.24) 303 m/z=667.82 (C47H29N3S=667.21) 304 m/z=667.82 (C47H29N3S=667.21) 305 m/z=641.78 (C45H27N3S=641.19) 306 m/z=717.88 (C51H31N3S=717.22) 307 m/z=641.78 (C45H27N3S=641.19) 308 m/z=717.88 (C51H31N3S=717.22) 309 m/z=717.88 (C51H31N3S=717.22) 310 m/z=717.88 (C51H31N3S=717.22) 311 m/z=793.97 (C57H35N3S=793.26) 312 m/z=717.88 (C51H31N3S=717.22) 313 m/z=793.97 (C57H35N3S=793.26) 314 m/z=641.78 (C45H27N3S=641.19) 315 m/z=717.88 (C51H31N3S=717.22) 316 m/z=641.78 (C45H27N3S=641.19) 317 m/z=717.88 (C51H31N3S=717.22) 318 m/z=717.88 (C51H31N3S=717.22) 319 m/z=793.97 (C57H35N3S=793.26) 320 m/z=717.88 (C51H31N3S=717.22) 321 m/z=793.97 (C57H35N3S=793.26) 322 m/z=793.97 (C57H35N3S=793.26) 323 m/z=641.78 (C45H27N3S=641.19) 324 m/z=717.88 (C51H31N3S=717.22) 325 m/z=641.78 (C45H27N3S=641.19) 326 m/z=717.88 (C51H31N3S=717.22) 327 m/z=717.88 (C51H31N3S=717.22) 328 m/z=717.88 (C51H31N3S=717.22) 329 m/z=793.97 (C57H35N3S=793.26) 330 m/z=717.88 (C51H31N3S=717.22) 331 m/z=793.97 (C57H35N3S=793.26) 332 m/z=793.97 (C57H35N3S=793.26) 333 m/z=641.78 (C45H27N3S=641.19) 334 m/z=717.88 (C51H31N3S=717.22) 335 m/z=641.78 (C45H27N3S=641.19) 336 m/z=717.88 (C51H31N3S=717.22) 337 m/z=793.97 (C57H35N3S=793.26) 338 m/z=717.88 (C51H31N3S=717.22) 339 m/z=717.88 (C51H31N3S=717.22) 340 m/z=793.97 (C57H35N3S=793.26) 341 m/z=717.88 (C51H31N3S=717.22) 342 m/z=793.97 (C57H35N3S=793.26) 343 m/z=717.88 (C51H31N3S=717.22) 344 m/z=691.84 (C49H29N3S=691.21) 345 m/z=691.84 (C49H29N3S=691.21) 346 m/z=767.94 (C55H33N3S=767.24) 347 m/z=767.94 (C55H33N3S=767.24) 348 m/z=767.94 (C55H33N3S=767.24) 349 m/z=691.84 (C49H29N3S=691.21) 350 m/z=691.84 (C49H29N3S=691.21) 351 m/z=767.94 (C55H33N3S=767.24) 352 m/z=767.94 (C55H33N3S=767.24) 353 m/z=767.94 (C55H33N3S=767.24) 354 m/z=767.94 (C55H33N3S=767.24) 355 m/z=691.84 (C49H29N3S=691.21) 356 m/z=691.84 (C49H29N3S=691.21) 357 m/z=767.94 (C55H33N3S=767.24) 358 m/z=767.94 (C55H33N3S=767.24) 359 m/z=767.94 (C55H33N3S=767.24) 360 m/z=767.94 (C55H33N3S=767.24) 361 m/z=691.84 (C49H29N3S=691.21) 362 m/z=767.94 (C55H33N3S=767.24) 363 m/z=767.94 (C55H33N3S=767.24) 364 m/z=767.94 (C55H33N3S=767.24) 365 m/z=767.94 (C55H33N3S=767.24) 366 m/z=780.93 (C55H32N4S=780.23) 367 m/z=808.00 (C58H37N3S=807.27) 368 m/z=706.85 (C49H30N4S=706.22) 369 m/z=706.85 (C49H30N4S=706.22) 370 m/z=707.84 (C49H29N3OS=707.20) 371 m/z=707.84 (C49H29N3OS=707.20) 372 m/z=723.90 (C49H29N3S2=723.18) 373 m/z=723.90 (C49H29N3S2=723.18) 374 m/z=525.60 (C37H23N3O=525.18) 375 m/z=601.69 (C43H27N3O=601.22) 376 m/z=677.79 (C49H31N3O=677.25) 377 m/z=525.60 (C37H23N3O=525.18) 378 m/z=601.69 (C43H27N3O=601.22) 379 m/z=601.69 (C43H27N3O=601.22) 380 m/z=601.69 (C43H27N3O=601.22) 381 m/z=677.79 (C49H31N3O=677.25) 382 m/z=677.79 (C49H31N3O=677.25) 383 m/z=753.89 (C55H35N3O=753.28) 384 m/z=753.89 (C55H35N3O=753.28) 385 m/z=601.69 (C43H27N3O=601.22) 386 m/z=677.79 (C49H31N3O=677.25) 387 m/z=677.79 (C49H31N3O=677.25) 388 m/z=525.60 (C37H23N3O=525.18) 389 m/z=601.69 (C43H27N3O=601.22) 390 m/z=525.60 (C37H23N3O=525.18) 391 m/z=601.69 (C43H27N3O=601.22) 392 m/z=601.69 (C43H27N3O=601.22) 393 m/z=677.79 (C49H31N3O=677.25) 394 m/z=601.69 (C43H27N3O=601.22) 395 m/z=677.79 (C49H31N3O=677.25) 396 m/z=753.89 (C55H35N3O=753.28) 397 m/z=601.69 (C43H27N3O=601.22) 398 m/z=677.79 (C49H31N3O=677.25) 399 m/z=677.79 (C49H31N3O=677.25) 400 m/z=753.89 (C55H35N3O=753.28) 401 m/z=525.60 (C37H23N3O=525.18) 402 m/z=601.69 (C43H27N3O=601.22) 403 m/z=525.60 (C37H23N3O=525.18) 404 m/z=601.69 (C43H27N3O=601.22) 405 m/z=601.69 (C43H27N3O=601.22) 406 m/z=601.69 (C43H27N3O=601.22) 407 m/z=677.79 (C49H31N3O=677.25) 408 m/z=753.89 (C55H35N3O=753.28) 409 m/z=601.69 (C43H27N3O=601.22) 410 m/z=677.79 (C49H31N3O=677.25) 411 m/z=677.79 (C49H31N3O=677.25) 412 m/z=753.89 (C55H35N3O=753.28) 413 m/z=525.60 (C37H23N3O=525.18) 414 m/z=601.69 (C43H27N3O=601.22) 415 m/z=525.60 (C37H23N3O=525.18) 416 m/z=601.69 (C43H27N3O=601.22) 417 m/z=601.69 (C43H27N3O=601.22) 418 m/z=601.69 (C43H27N3O=601.22) 419 m/z=677.79 (C49H31N3O=677.25) 420 m/z=753.89 (C55H35N3O=753.28) 421 m/z=601.69 (C43H27N3O=601.22) 422 m/z=677.79 (C49H31N3O=677.25) 423 m/z=677.79 (C49H31N3O=677.25) 424 m/z=753.89 (C55H35N3O=753.28) 425 m/z=575.66 (C41H25N3O=575.20) 426 m/z=651.75 (C47H29N3O=651.23) 427 m/z=575.66 (C41H25N3O=575.20) 428 m/z=651.75 (C47H29N3O=651.23) 429 m/z=651.75 (C47H29N3O=651.23) 430 m/z=651.75 (C47H29N3O=651.23) 431 m/z=727.85 (C53H33N3O=717.22) 432 m/z=651.75 (C47H29N3O=651.23) 433 m/z=727.85 (C53H33N3O=727.26) 434 m/z=727.85 (C53H33N3O=727.26) 435 m/z=803.94 (C59H37N3O=803.29) 436 m/z=575.66 (C41H25N3O=575.20) 437 m/z=575.66 (C41H25N3O=641.19) 438 m/z=651.75 (C47H29N3O=651.23) 439 m/z=651.75 (C47H29N3O=651.23) 440 m/z=651.75 (C47H29N3O=651.23) 441 m/z=727.85 (C53H33N3O=727.26) 442 m/z=803.94 (C59H37N3O=803.29) 443 m/z=651.75 (C47H29N3O=651.23) 444 m/z=727.85 (C53H33N3O=727.26) 445 m/z=727.85 (C53H33N3O=727.26) 446 m/z=803.94 (C59H37N3O=803.29) 447 m/z=575.66 (C41H25N3O=575.20) 448 m/z=651.75 (C47H29N3O=651.23) 449 m/z=575.66 (C41H25N3O=575.20) 450 m/z=651.75 (C47H29N3O=651.23) 451 m/z=651.75 (C47H29N3O=651.23) 452 m/z=727.85 (C53H33N3O=727.26) 453 m/z=651.75 (C47H29N3O=651.23) 454 m/z=727.85 (C53H33N3O=727.26) 455 m/z=803.94 (C59H37N3O=803.29) 456 m/z=651.75 (C47H29N3O=651.23) 457 m/z=727.85 (C53H33N3O=727.26) 458 m/z=803.94 (C59H37N3O=803.29) 459 m/z=575.66 (C41H25N3O=575.20) 460 m/z=651.75 (C47H29N3O=651.23) 461 m/z=651.75 (C47H29N3O=651.23) 462 m/z=727.85 (C53H33N3O=727.26) 463 m/z=803.94 (C59H37N3O=803.29) 464 m/z=651.75 (C47H29N3O=651.23) 465 m/z=727.85 (C53H33N3O=727.26) 466 m/z=727.85 (C53H33N3O=727.26) 467 m/z=651.75 (C47H29N3O=651.23) 468 m/z=727.85 (C53H33N3O=727.26) 469 m/z=651.75 (C47H29N3O=793.26) 470 m/z=651.75 (C47H29N3O=651.23) 471 m/z=625.72 (C45H27N3O=625.22) 472 m/z=701.81 (C51H31N3O=701.25) 473 m/z=625.72 (C45H27N3O=625.22) 474 m/z=701.81 (C51H31N3O=701.25) 475 m/z=701.81 (C51H31N3O=701.25) 476 m/z=701.81 (C51H31N3O=701.25) 478 m/z=777.91 (C57H35N3O=777.28) 479 m/z=777.91 (C57H35N3O=777.28) 480 m/z=625.72 (C45H27N3O=625.22) 481 m/z=701.81 (C51H31N3O=701.25) 482 m/z=625.72 (C45H27N3O=625.22) 483 m/z=701.81 (C51H31N3O=701.25) 484 m/z=701.81 (C51H31N3O=701.25) 485 m/z=701.81 (C51H31N3O=701.25) 486 m/z=777.91 (C57H35N3O=777.28) 487 m/z=701.81 (C51H31N3O=701.25) 488 m/z=777.91 (C57H35N3O=777.28) 489 m/z=777.91 (C57H35N3O=777.28) 490 m/z=625.72 (C45H27N3O=625.22) 491 m/z=701.81 (C51H31N3O=701.25) 492 m/z=777.91 (C57H35N3O=777.28) 493 m/z=625.72 (C45H27N3O=625.22) 494 m/z=701.81 (C51H31N3O=701.25) 495 m/z=701.81 (C51H31N3O=701.25) 496 m/z=777.91 (C57H35N3O=777.28) 497 m/z=701.81 (C51H31N3O=701.25) 498 m/z=701.81 (C51H31N3O=701.25) 499 m/z=777.91 (C57H35N3O=777.28) 500 m/z=777.91 (C57H35N3O=777.28) 501 m/z=625.72 (C45H27N3O=625.22) 502 m/z=701.81 (C51H31N3O=701.25) 503 m/z=625.72 (C45H27N3O=625.22) 504 m/z=701.81 (C51H31N3O=701.25) 505 m/z=777.91 (C57H35N3O=777.28) 506 m/z=701.81 (C51H31N3O=701.25) 507 m/z=777.91 (C57H35N3O=777.28) 508 m/z=701.81 (C51H31N3O=701.25) 509 m/z=777.91 (C57H35N3O=777.28) 510 m/z=701.81 (C51H31N3O=701.25) 511 m/z=777.91 (C57H35N3O=777.28) 512 m/z=701.81 (C51H31N3O=701.25) 513 m/z=675.77 (C49H29N3O=675.23) 514 m/z=751.87 (C55H33N3O=751.26) 515 m/z=675.77 (C49H29N3O=675.23) 516 m/z=751.87 (C55H33N3O=751.26) 517 m/z=751.87 (C55H33N3O=751.26) 518 m/z=751.87 (C55H33N3O=751.26) 519 m/z=675.77 (C49H29N3O=675.23) 520 m/z=675.77 (C49H29N3O=675.23) 521 m/z=751.87 (C55H33N3O=751.26) 522 m/z=751.87 (C55H33N3O=751.26) 523 m/z=751.87 (C55H33N3O=751.26) 524 m/z=675.77 (C49H29N3O=675.23) 525 m/z=675.77 (C49H29N3O=675.23) 526 m/z=751.87 (C55H33N3O=751.26) 527 m/z=751.87 (C55H33N3O=751.26) 528 m/z=751.87 (C55H33N3O=751.26) 529 m/z = 675.77 (C49H29N3O=675.23) 530 m/z=675.77 (C49H29N3O=675.23) 531 m/z=751.87 (C55H33N3O=751.26) 532 m/z=751.87 (C55H33N3O=751.26) 533 m/z=764.87 (C55H32N4O=764.26) 534 m/z=791.93 (C58H37N3O=791.29) 535 m/z=690.79 (C49H30N4O=690.24) 536 m/z=690.79 (C49H30N4O=690.24) 537 m/z=691.77 (C49H29N3O2=691.23) 538 m/z=691.77 (C49H29N3O2=691.23) 539 m/z=707.84 (C49H29N3OS=707.20) 540 m/z=707.84 (C49H29N3OS=707.20) 541 m/z=542.65 (C36H22N4S=542.16) 542 m/z=618.75 (C42H26N4S=618.19) 543 m/z=694.84 (C48H30N4S=694.22) 544 m/z=542.65 (C36H22N4S=542.16) 545 m/z=618.75 (C42H26N4S=618.19) 546 m/z=592.71 (C40H24N4S=592.17) 547 m/z=668.81 (C46H28N4S=668.20) 548 m/z=592.71 (C40H24N4S=592.17) 549 m/z=668.81 (C46H28N4S=668.20) 550 m/z=642.77 (C44H26N4S=642.19) 551 m/z=718.87 (C50H30N4S=718.22) 552 m/z=642.77 (C44H26N4S=642.19) 553 m/z=718.87 (C50H30N4S=718.22) 554 m/z=692.83 (C48H28N4S=692.20) 555 m/z=768.92 (C54H32N4S=768.23) 556 m/z=692.83 (C48H28N4S=692.20) 557 m/z=768.92 (C54H32N4S=768.23) 558 m/z=526.59 (C36H22N4O=526.18) 559 m/z=602.68 (C42H26N4O=602.21) 560 m/z=526.59 (C36H22N4O=526.18) 561 m/z=602.68 (C42H26N4O=602.21) 562 m/z=576.64 (C40H24N4O=576.20) 563 m/z=652.74 (C46H28N4O=652.23) 564 m/z=576.64 (C40H24N4O=576.20) 565 m/z=652.74 (C46H28N4O=652.23) 566 m/z=626.70 (C44H26N4O=626.21) 567 m/z=702.80 (C50H30N4O=702.24) 568 m/z=626.70 (C44H26N4O=626.21) 569 m/z=702.80 (C50H30N4O=702.24) 570 m/z=676.76 (C48H28N4O=676.23) 571 m/z=752.86 (C54H32N4O=752.26) 572 m/z=676.76 (C48H28N4O=676.23) 573 m/z=752.86 (C54H32N4O=752.26) 574 m/z=618.75 (C42H26N4S=618.19) 575 m/z=694.84 (C48H30N4S=694.22) 576 m/z=694.84 (C48H30N4S=694.22) 577 m/z=770.94 (C54H34N4S=770.25) 578 m/z=770.94 (C54H34N4S=770.25) 579 m/z=618.75 (C42H26N4S=618.19) 580 m/z=618.75 (C42H26N4S=618.19) 581 m/z=694.84 (C48H30N4S=694.22) 582 m/z=618.75 (C42H26N4S=618.19) 583 m/z=618.75 (C42H26N4S=618.19) 584 m/z=694.84 (C48H30N4S=694.22) 585 m/z=618.75 (C42H26N4S=618.19) 586 m/z=618.75 (C42H26N4S=618.19) 587 m/z=618.75 (C42H26N4S=618.19) 588 m/z=770.94 (C54H34N4S=770.25) 589 m/z=618.75 (C42H26N4S=618.19) 590 m/z=707.84 (C48H29N5S=707.21) 591 m/z=734.91 (C51H34N4S=734.25) 592 m/z=663.76 (C45H30NOPS=663.18) 593 m/z=668.81 (C46H28N4S=668.20) 594 m/z=744.90 (C52H32N4S=744.23) 595 m/z=668.81 (C46H28N4S=668.20) 596 m/z=744.90 (C52H32N4S=744.23) 597 m/z=668.81 (C46H28N4S=668.20) 598 m/z=668.81 (C46H28N4S=668.20) 599 m/z=744.90 (C52H32N4S=744.23) 600 m/z=668.81 (C46H28N4S=668.20) 601 m/z=668.81 (C46H28N4S=668.20) 602 m/z=744.90 (C52H32N4S=744.23) 603 m/z=668.81 (C46H28N4S=668.20) 604 m/z=718.87 (C50H30N4S=718.22) 605 m/z=794.96 (C56H34N4S=794.25) 606 m/z=718.87 (C50H30N4S=718.22) 607 m/z=718.87 (C50H30N4S=718.22) 608 m/z=794.96 (C56H34N4S=794.25) 609 m/z=718.87 (C50H30N4S=718.22) 610 m/z=768.92 (C54H32N4S=768.23) 611 m/z=768.92 (C54H32N4S=768.23) 612 m/z=768.92 (C54H32N4S=768.23) 613 m/z=768.92 (C54H32N4S=768.23) 614 m/z=768.92 (C54H32N4S=768.23) 615 m/z=768.92 (C54H32N4S=768.23) 616 m/z=768.92 (C54H32N4S=768.23) 617 m/z=768.92 (C54H32N4S=768.23) 618 m/z=708.83 (C48H28N4OS=708.20) 619 m/z=784.92 (C54H32N4OS=784.23) 620 m/z=708.83 (C48H28N4OS=708.20) 621 m/z=708.83 (C48H28N4OS=708.20) 622 m/z=784.92 (C54H32N4OS=784.23) 623 m/z=708.83 (C48H28N4OS=708.20) 624 m/z=708.83 (C48H28N4OS=708.20) 625 m/z=784.92 (C54H32N4OS=784.23) 626 m/z=708.83 (C48H28N4OS=708.20) 627 m/z=708.83 (C48H28N4OS=708.20) 628 m/z=784.92 (C54H32N4OS=784.23) 629 m/z=708.83 (C48H28N4OS=708.20) 630 m/z=784.92 (C54H32N4OS=784.23) 631 m/z=784.92 (C54H32N4OS=784.23) 632 m/z=784.92 (C54H32N4OS=784.23) 633 m/z=784.92 (C54H32N4OS=784.23) 634 m/z=724.89 (C48H28N4S2=724.18) 635 m/z=800.99 (C54H32N4S2=717.22) 636 m/z=724.89 (C48H28N4S2=724.18) 637 m/z=724.89 (C48H28N4S2=724.18) 638 m/z=800.99 (C54H32N4S2=800.21) 639 m/z=724.89 (C48H28N4S2=717.22) 640 m/z=724.89 (C48H28N4S2=724.18) 641 m/z=800.99 (C51H31N3S=717.22) 642 m/z=723.90 (C49H29N3S2=723.18) 643 m/z=724.89 (C48H28N4S2=724.18) 644 m/z=800.99 (C54H32N4S2=800.21) 645 m/z=724.89 (C48H28N4S2=724.18) 646 m/z=800.99 (C54H32N4S2=800.21) 647 m/z=800.99 (C54H32N4S2=800.21) 648 m/z=800.99 (C54H32N4S2=800.21) 649 m/z=800.99 (C54H32N4S2=717.22) 650 m/z=783.94 (C54H33N5S=783.25) 651 m/z=783.94 (C54H33N5S=783.25) 652 m/z=784.92 (C54H32N4OS=784.23) 653 m/z=784.92 (C54H32N4OS=784.23) 654 m/z=800.99 (C54H32N4S2=800.21) 655 m/z=800.99 (C54H32N4S2=800.21) 656 m/z=602.68 (C42H26N4O=602.21) 657 m/z=678.78 (C48H30N4O=678.24) 658 m/z=678.78 (C48H30N4O=678.24) 659 m/z=754.87 (C54H34N4O=754.27) 660 m/z=602.68 (C42H26N4O=602.21) 661 m/z=602.68 (C42H26N4O=602.21) 662 m/z=602.68 (C42H26N4O=602.21) 663 m/z=691.78 (C48H29N5O=691.24) 664 m/z=718.84 (C51H34N4O=718.27) 665 m/z=602.68 (C42H26N4O=602.21) 666 m/z=678.78 (C48H30N4O=678.24) 667 m/z=602.68 (C42H26N4O=602.21) 668 m/z=678.78 (C48H30N4O=678.24) 669 m/z=602.68 (C42H26N4O=602.21) 670 m/z=602.68 (C42H26N4O=602.21) 671 m/z=678.78 (C48H30N4O=678.24) 672 m/z=602.68 (C42H26N4O=602.21) 673 m/z=647.70 (C45H30NO2P=647.20) 674 m/z=652.74 (C46H28N4O=652.23) 675 m/z=804.93 (C58H36N4O=804.29) 676 m/z=652.74 (C46H28N4O=652.23) 677 m/z=652.74 (C46H28N4O=652.23) 678 m/z=804.93 (C58H36N4O=804.29) 679 m/z=652.74 (C46H28N4O=641.19) 680 m/z=652.74 (C46H28N4O=652.23) 681 m/z=804.93 (C58H36N4O=804.29) 682 m/z=652.74 (C46H28N4O=652.23) 683 m/z=652.74 (C46H28N4O=652.23) 684 m/z=804.93 (C58H36N4O=804.29) 685 m/z=652.74 (C46H28N4O=652.23) 686 m/z=702.80 (C50H30N4O=702.24) 687 m/z=854.99 (C62H38N4O=854.30) 688 m/z=702.80 (C50H30N4O=702.24) 689 m/z=702.80 (C50H30N4O=702.24) 690 m/z=854.99 (C62H38N4O=854.30) 691 m/z=702.80 (C50H30N4O=702.24) 692 m/z=702.80 (C50H30N4O=702.24) 693 m/z=778.90 (C56H34N4O=778.27) 694 m/z=702.80 (C50H30N4O=702.24) 695 m/z=702.80 (C50H30N4O=702.24) 696 m/z=778.90 (C56H34N4O=778.27) 697 m/z=702.80 (C50H30N4O=702.24) 698 m/z=752.86 (C54H32N4O=752.26) 699 m/z=752.86 (C54H32N4O=752.26) 700 m/z=752.86 (C54H32N4O=752.26) 701 m/z=752.86 (C54H32N4O=752.26) 702 m/z=752.86 (C54H32N4O=752.26) 703 m/z=752.86 (C54H32N4O=752.26) 704 m/z=752.86 (C54H32N4O=752.26) 705 m/z=752.86 (C54H32N4O=752.26) 706 m/z=692.76 (C48H28N4O2=692.22) 707 m/z=768.86 (C54H32N4O2=768.25) 708 m/z=692.76 (C48H28N4O2=692.22) 709 m/z=692.76 (C48H28N4O2=692.22) 710 m/z=768.86 (C54H32N4O2=768.25) 711 m/z=692.76 (C48H28N4O2=692.22) 712 m/z=692.76 (C48H28N4O2=692.22) 713 m/z=768.86 (C54H32N4O2=768.25) 714 m/z=692.76 (C48H28N4O2=692.22) 715 m/z=692.76 (C48H28N4O2=692.22) 716 m/z=768.86 (C54H32N4O2=768.25) 717 m/z=692.76 (C48H28N4O2=692.22) 718 m/z=768.86 (C54H32N4O2=768.25) 719 m/z=768.86 (C54H32N4O2=768.25) 720 m/z=768.86 (C54H32N4O2=768.25) 721 m/z=768.86 (C54H32N4O2=768.25) 722 m/z=708.83 (C48H28N4OS=708.20) 723 m/z=784.92 (C54H32N4OS=784.23) 724 m/z=708.83 (C48H28N4OS=708.20) 725 m/z=708.83 (C48H28N4OS=708.20) 726 m/z=708.83 (C48H28N4OS=708.20) 727 m/z=708.83 (C48H28N4OS=708.20) 728 m/z=784.92 (C54H32N4OS=784.23) 729 m/z=708.83 (C48H28N4OS=708.20) 730 m/z=708.83 (C48H28N4OS=708.20) 731 m/z=784.92 (C54H32N4OS=784.23) 732 m/z=708.83 (C48H28N4OS=708.20) 733 m/z=784.92 (C54H32N4OS=784.23) 734 m/z=784.92 (C54H32N4OS=784.23) 735 m/z=784.92 (C54H32N4OS=784.23) 736 m/z=784.92 (C54H32N4OS=784.23) 737 m/z=767.87 (C54H33N5O=767.27) 738 m/z=767.87 (C54H33N5O=767.27) 739 m/z=768.86 (C54H32N4O2=768.25) 740 m/z=768.86 (C54H32N4O2=768.25) 741 m/z=784.92 (C54H32N4OS=784.23) 742 m/z=784.92 (C54H32N4OS=784.23) 743 m/z=617.76 (C43H27N3S=617.19) 744 m/z=693.86 (C49H31N3S=693.22) 745 m/z=693.86 (C49H31N3S=693.22) 746 m/z=769.95 (C55H35N3S=769.26) 747 m/z=617.76 (C43H27N3S=617.19) 748 m/z=693.86 (C49H31N3S=693.22) 749 m/z=769.95 (C55H35N3S=769.26) 750 m/z=617.76 (C43H27N3S=617.19) 751 m/z=769.95 (C55H35N3S=769.26) 752 m/z=617.76 (C43H27N3S=617.19) 753 m/z=693.86 (C49H31N3S=693.22) 754 m/z=693.86 (C49H31N3S=693.22) 755 m/z=618.75 (C42H26N4S=618.19) 756 m/z=617.76 (C43H27N3S=617.19) 757 m/z=693.86 (C49H31N3S=693.22) 758 m/z=617.76 (C43H27N3S=617.19) 759 m/z=693.86 (C49H31N3S=693.22) 760 m/z=769.95 (C55H35N3S=769.26) 761 m/z=617.76 (C43H27N3S=617.19) 762 m/z=693.86 (C49H31N3SS=693.22) 763 m/z=617.76 (C43H27N3S=617.19) 764 m/z=693.86 (C49H31N3S=693.22) 765 m/z=769.95 (C55H35N3S=769.26) 766 m/z=617.76 (C43H27N3S=617.19) 767 m/z=617.76 (C43H27N3S=617.19) 768 m/z=667.82 (C47H29N3S=667.21) 769 m/z=743.91 (C53H33N3S=743.24) 770 m/z=667.82 (C47H29N3S=667.21) 771 m/z=743.91 (C53H33N3S=743.24) 772 m/z=667.82 (C47H29N3S=667.21) 773 m/z=667.82 (C47H29N3S=667.21) 774 m/z=743.91 (C53H33N3S=743.24) 775 m/z=743.91 (C53H33N3S=743.24) 776 m/z=667.82 (C47H29N3S=667.21) 777 m/z=667.82 (C47H29N3S=667.21) 778 m/z=743.24 (C53H33N3S=743.24) 779 m/z=667.82 (C47H29N3S=667.21) 780 m/z=743.91 (C53H33N3S=743.24) 781 m/z=667.21 (C47H29N3S=667.21) 782 m/z=743.91 (C53H33N3S=743.24) 783 m/z=667.82 (C47H29N3S=667.21) 784 m/z=743.91 (C53H33N3S=743.24) 785 m/z=667.82 (C47H29N3S=667.21) 786 m/z=667.82 (C47H29N3S=667.21) 787 m/z=717.88 (C51H31N3S=717.22) 788 m/z=793.97 (C57H35N3S=793.26) 789 m/z=717.88 (C51H31N3S=717.22) 790 m/z=793.97 (C57H35N3S=793.26) 791 m/z=717.88 (C51H31N3S=717.22) 792 m/z=717.88 (C51H31N3S=717.22) 793 m/z=793.97 (C57H35N3S=793.26) 794 m/z=793.97 (C57H35N3S=793.26) 795 m/z=717.88 (C51H31N3S=717.22) 796 m/z=717.88 (C51H31N3S=717.22) 797 m/z=793.97 (C57H35N3S=793.26) 798 m/z=717.88 (C51H31N3S=717.22) 799 m/z=793.97 (C57H35N3S=793.26) 800 m/z=717.88 (C51H31N3S=717.22) 801 m/z=793.97 (C57H35N3S=793.26) 802 m/z=717.88 (C51H31N3S=717.22) 803 m/z=793.97 (C57H35N3S=793.26) 804 m/z=717.88 (C51H31N3S=717.22) 805 m/z=717.88 (C51H31N3S=717.22) 806 m/z=767.94 (C55H33N3S=767.24) 807 m/z=767.94 (C55H33N3S=767.24) 808 m/z=767.94 (C55H33N3S=767.24) 809 m/z=767.94 (C55H33N3S=767.24) 810 m/z=767.94 (C55H33N3S=767.24) 811 m/z=767.94 (C55H33N3S=767.24) 812 m/z=707.84 (C49H29N3OS=707.20) 813 m/z=707.84 (C49H29N3OS=707.20) 814 m/z=707.84 (C49H29N3OS=707.20) 815 m/z=707.84 (C49H29N3OS=707.20) 816 m/z=707.84 (C49H29N3OS=707.20) 817 m/z=723.90 (C49H29N3S2=723.18) 818 m/z=723.90 (C49H29N3S2=723.18) 819 m/z=723.90 (C49H29N3S2=723.18) 820 m/z=723.90 (C49H29N3S2=723.18) 821 m/z=723.90 (C49H29N3S2=723.18) 822 m/z=706.85 (C49H30N4S=706.22) 823 m/z=733.92 (C52H35N3S=733.26) 824 m/z=782.95 (C55H34N4S=782.25) 825 m/z=782.95 (C55H34N4S=782.25) 826 m/z=783.94 (C55H33N3OS=783.23) 827 m/z=783.94 (C55H33N3OS=783.23) 828 m/z=800.00 (C55H33N3S2=799.21) 829 m/z=800.00 (C55H33N3S2=799.21) 830 m/z=601.69 (C43H27N3O=601.22) 831 m/z=677.79 (C49H31N3O=677.25) 832 m/z=753.89 (C55H35N3O=753.28) 833 m/z=601.69 (C43H27N3O=601.22) 834 m/z=677.79 (C49H31N3O=677.25) 835 m/z=677.79 (C49H31N3O=677.25) 836 m/z=601.69 (C43H27N3O=601.22) 837 m/z=677.79 (C49H31N3O=677.25) 838 m/z=601.69 (C43H27N3O=601.22) 839 m/z=677.79 (C49H31N3O=677.25) 840 m/z=753.89 (C55H35N3O=753.28) 841 m/z=602.68 (C42H26N4O=602.21) 842 m/z=601.69 (C43H27N3O=601.22) 843 m/z=677.79 (C49H31N3O=677.25) 844 m/z=601.69 (C43H27N3O=601.22) 845 m/z=677.79 (C49H31N3O=677.25) 846 m/z=753.89 (C55H35N3O=753.28) 847 m/z=601.69 (C43H27N3O=601.22) 848 m/z=677.79 (C49H31N3O=677.25) 849 m/z=601.69 (C43H27N3O=601.22) 850 m/z=677.79 (C49H31N3O=677.25) 851 m/z=677.79 (C49H31N3O=677.25) 852 m/z=753.89 (C55H35N3O=753.28) 853 m/z=601.69 (C43H27N3O=601.22) 854 m/z=601.69 (C43H27N3O=601.22) 855 m/z=651.75 (C47H29N3O=651.23) 856 m/z=651.75 (C47H29N3O=651.23) 857 m/z=727.85 (C53H33N3O=727.26) 858 m/z=727.85 (C53H33N3O=727.26) 859 m/z=651.75 (C47H29N3O=651.23) 860 m/z=727.85 (C53H33N3O=727.26) 861 m/z=651.75 (C47H29N3O=651.23) 862 m/z=727.85 (C53H33N3O=727.26) 863 m/z=651.75 (C47H29N3O=651.23) 864 m/z=651.75 (C47H29N3O=651.23) 865 m/z=727.85 (C53H33N3O=727.26) 866 m/z=651.75 (C47H29N3O=651.23) 867 m/z=727.85 (C53H33N3O=727.26) 868 m/z=651.75 (C47H29N3O=651.23) 869 m/z=727.85 (C53H33N3O=727.26) 870 m/z=651.75 (C47H29N3O=651.23) 871 m/z=727.85 (C53H33N3O=727.26) 872 m/z=651.75 (C47H29N3O=651.23) 873 m/z=651.75 (C47H29N3O=651.23) 874 m/z=701.81 (C51H31N3O=701.25) 875 m/z=701.81 (C51H31N3O=701.25) 876 m/z=777.91 (C57H35N3O=777.28) 877 m/z=777.91 (C57H35N3O=777.28) 878 m/z=701.81 (C51H31N3O=701.25) 879 m/z=777.91 (C57H35N3O=777.28) 880 m/z=701.81 (C51H31N3O=701.25) 881 m/z=777.91 (C57H35N3O=777.28) 882 m/z=701.81 (C51H31N3O=701.25) 883 m/z=701.81 (C51H31N3O=701.25) 884 m/z=777.91 (C57H35N3O=777.28) 885 m/z=701.81 (C51H31N3O=701.25) 886 m/z=777.91 (C57H35N3O=777.28) 887 m/z=701.81 (C51H31N3O=701.25) 888 m/z=777.91 (C57H35N3O=777.28) 889 m/z=701.81 (C51H31N3O=701.25) 890 m/z=777.91 (C57H35N3O=777.28) 891 m/z=701.81 (C51H31N3O=701.25) 892 m/z=701.81 (C51H31N3O=701.25) 893 m/z=751.87 (C55H33N3O=751.26) 894 m/z=751.87 (C55H33N3O=751.26) 895 m/z=827.97 (C61H37N3O=827.29) 896 m/z=827.97 (C61H37N3O=827.29) 897 m/z=751.87 (C55H33N3O=751.26) 898 m/z=827.97 (C61H37N3O=827.29) 899 m/z=751.87 (C55H33N3O=751.26) 900 m/z=751.87 (C55H33N3O=751.26) 901 m/z=691.77 (C49H29N3O2=691.23) 902 m/z=691.77 (C49H29N3O2=691.23) 903 m/z=767.87 (C55H33N3O2=767.26) 904 m/z=767.87 (C55H33N3O2=767.26) 905 m/z=691.77 (C49H29N3O2=691.23) 906 m/z=767.87 (C55H33N3O2=767.26) 907 m/z=691.77 (C49H29N3O2=691.23) 908 m/z=691.77 (C49H29N3O2=691.23) 909 m/z=707.84 (C49H29N3OS=707.20) 910 m/z=707.84 (C49H29N3OS=707.20) 911 m/z=783.94 (C55H33N3OS=783.23) 912 m/z=783.94 (C55H33N3OS=783.23) 913 m/z=707.84 (C49H29N3OS=707.20) 914 m/z=783.94 (C55H33N3OS=783.23) 915 m/z=707.84 (C49H29N3OS=707.20) 916 m/z=707.84 (C49H29N3OS=707.20) 917 m/z=737.84 (C51H32NOPS=737.19) 918 m/z=690.79 (C49H30N4O=690.24) 919 m/z=717.85 (C52H35N3O=717.28) 920 m/z=766.88 (C55H34N4O=766.27) 921 m/z=766.88 (C55H34N4O=766.27) 922 m/z=767.87 (C55H33N3O2=767.26) 923 m/z=767.87 (C55H33N3O2=767.26) 924 m/z=783.94 (C55H33N3OS=783.23) 925 m/z=783.94 (C55H33N3OS=783.23) 926 m/z=592.71 (C40H24N4S=592.17) 927 m/z=757.90 (C52H31N5S=757.23) 928 m/z=758.89 (C52H30N4OS=758.21) 929 m/z=744.90 (C52H32N4S=744.23) 930 m/z=667.82 (C47H29N3S=667.21) 931 m/z=757.90 (C52H31N5S=757.23) 932 m/z=774.95 (C52H30N4S2=774.19) 933 m/z=820.01 (C59H37N3S=819.27) 934 m/z=756.91 (C53H32N4S=756.23) 935 m/z=757.90 (C53H31N3OS=757.22) 936 m/z=668.81 (C46H28N4S=668.20) 937 m/z=637.73 (C43H28NOPS=637.16) 938 m/z=576.64 (C40H24N4O=576.20) 939 m/z=741.84 (C52H31N5O=741.25) 940 m/z=742.82 (C52H30N4O2=742.24) 941 m/z=728.84 (C52H32N4O=728.26) 942 m/z=651.75 (C47H29N3O=651.23) 943 m/z=741.84 (C52H31N5O=741.25) 944 m/z=758.89 (C52H30N4OS=758.21) 945 m/z=803.94 (C59H37N3O=803.29) 946 m/z=740.85 (C53H32N4O=740.26) 947 m/z=741.83 (C53H31N3O2=741.24) 948 m/z=652.74 (C46H28N4O=652.23) 949 m/z=621.66 (C43H28NO2P=621.19) 950 m/z=592.71 (C40H24N4S=592.17) 951 m/z=757.90 (C52H31N5S=757.23) 952 m/z=758.89 (C52H30N4OS=758.21) 953 m/z=744.90 (C52H32N4S=744.23) 954 m/z=667.82 (C47H29N3S=667.21) 955 m/z=757.90 (C52H31N5S=757.23) 956 m/z=774.95 (C52H30N4S2=774.19) 957 m/z=820.01 (C59H37N3S=819.27) 958 m/z=756.91 (C53H32N4S=756.23) 959 m/z=757.90 (C53H31N3OS=757.22) 960 m/z=668.81 (C46H28N4S=668.20) 961 m/z=637.73 (C43H28NOPS=637.16) 962 m/z=576.64 (C40H24N4O=576.20) 963 m/z=741.84 (C52H31N5O=741.25) 964 m/z=742.82 (C52H30N4O2=742.24) 965 m/z=728.84 (C52H32N4O=728.26) 966 m/z=651.75 (C47H29N3O=651.23) 967 m/z=741.84 (C52H31N5O=741.25) 968 m/z=758.89 (C52H30N4OS=758.21) 969 m/z=803.94 (C59H37N3O=803.29) 970 m/z=740.85 (C53H32N4O=740.26) 971 m/z=741.83 (C53H31N3O2=741.24) 972 m/z=652.74 (C46H28N4O=652.23) 973 m/z=621.66 (C43H28NO2P=621.19) 974 m/z=592.71 (C40H24N4S=592.17) 975 m/z=757.90 (C52H31N5S=757.23) 976 m/z=758.89 (C52H30N4OS=758.21) 977 m/z=744.90 (C52H32N4S=744.23) 978 m/z=667.82 (C47H29N3S=667.21) 979 m/z=757.90 (C52H31N5S=757.23) 980 m/z=774.95 (C52H30N4S2=774.19) 981 m/z=820.01 (C59H37N3S=819.27) 982 m/z=756.91 (C53H32N4S=756.23) 983 m/z=757.90 (C53H31N3OS=757.22) 984 m/z=668.81 (C46H28N4S=668.20) 985 m/z=637.73 (C43H28NOPS=637.16) 986 m/z=576.64 (C40H24N4O=576.20) 987 m/z=741.84 (C52H31N5O=741.25) 988 m/z=742.82 (C52H30N4O2=742.24) 989 m/z=728.84 (C52H32N4O=728.26) 990 m/z=651.75 (C47H29N3O=651.23) 991 m/z=741.84 (C52H31N5O=741.25) 992 m/z=758.89 (C52H30N4OS=758.21) 993 m/z=803.94 (C59H37N3O=803.29) 994 m/z=740.85 (C53H32N4O=740.26) 995 m/z=741.83 (C53H31N3O2=741.24) 996 m/z=652.74 (C46H28N4O=652.23) 997 m/z=621.66 (C43H28NO2P=621.19) 998 m/z=641.78 (C45H27N3S=641.19) 999 m/z=691.84 (C49H29N3S=691.21) 1000 m/z=741.90 (C53H31N3S=741.22) 1001 m/z=791.96 (C57H33N3S=791.24) 1002 m/z=717.88 (C51H31N3S=717.22) 1003 m/z=767.94 (C55H33N3S=767.24) 1004 m/z=717.88 (C51H31N3S=717.22) 1005 m/z=767.94 (C55H33N3S=767.24) 1006 m/z=625.72 (C45H27N3O=625.22) 1007 m/z=675.77 (C49H29N3O=675.23) 1008 m/z=725.83 (C53H31N3O=725.25) 1009 m/z=775.89 (C57H33N3O=775.26) 1010 m/z=701.81 (C51H31N3O=701.25) 1011 m/z=751.87 (C55H33N3O=751.26) 1012 m/z=701.81 (C51H31N3O=701.25) 1013 m/z=751.87 (C55H33N3O=751.26) 1014 m/z=641.78 (C45H27N3S=641.19) 1015 m/z=691.84 (C49H29N3S=691.21) 1016 m/z=741.90 (C53H31N3S=741.22) 1017 m/z=791.96 (C57H33N3S=791.24) 1018 m/z=731.86 (C51H29N3OS=731.20) 1019 m/z=747.93 (C51H29N3S2=747.18) 1020 m/z=615.74 (C43H25N3S=615.18) 1021 m/z=615.74 (C43H25N3S=615.18) 1022 m/z=783.94 (C43H25N3S=615.18) 1023 m/z=625.72 (C45H27N3O=625.22) 1024 m/z=675.77 (C49H29N3O=675.23) 1025 m/z=725.83 (C53H31N3O=725.25) 1026 m/z=775.89 (C57H33N3O=775.26) 1027 m/z=715.79 (C51H29N3O2=715.23) 1028 m/z=731.86 (C51H29N3OS=731.20) 1029 m/z=599.68 (C43H25N3O=599.20) 1030 m/z=599.68 (C43H25N3O=599.20) 1031 m/z=599.68 (C43H25N3O=599.20)

＜ Experimental example 1＞- Manufacturing organic light-emitting devices

1) Manufacturing organic light-emitting devices

The transparent ITO electrode film obtained from the glass used for OLED (manufactured by Samsung-Corning Co., Ltd.) was washed with trichloroethylene, acetone, ethanol and distilled water ultrasonically for 5 minutes, and stored in isopropanol, use.

Next, mount the ITO substrate in the substrate holder of the vacuum depositor, and introduce the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2- TNATA) to the chamber in the vacuum depositor.

Subsequently, the chamber was evacuated until the vacuum degree therein reached 10 ^-6 Torr, and then 2-TNATA was evaporated by applying a current to the cell chamber to deposit a hole injection layer with a thickness of 600 angstroms on the ITO substrate.

Introduce the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) into the other chamber of the vacuum depositor, and then A current is applied to the chamber to evaporate to deposit a hole transfer layer with a thickness of 300 angstroms on the hole injection layer.

After forming the hole injection layer and the hole transfer layer as described above, a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, in a side chamber in a vacuum depositor, the blue light-emitting host material H1 is vacuum-deposited to a thickness of 200 angstroms, and the blue light-emitting dopant material D1 is vacuum-deposited on it relative to the host material. 5%.

Subsequently, one of the compounds described in Table 60 below was deposited to a thickness of 300 angstroms as an electron transfer layer.

As the electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to have a thickness of 1,000 angstroms to manufacture an OLED.

At the same time, all the organic compounds needed to manufacture OLEDs are purified by vacuum sublimation of each material used in OLED manufacturing at 10 ^-6 Torr to 10 ^-8 Torr.

The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE) and lifetime of the blue organic light-emitting device manufactured according to the present disclosure are shown in Table 60 below.

[Table 60] Compound Drive voltage (V) Luminous efficiency (cd/A) CIE (x, y) Life (T95) Comparative example 1 E1 5.70 6.00 (0.134, 0.102) 20 Comparative example 2 E2 5.71 5.98 (0.134, 0.100) twenty two Comparative example 3 E3 5.70 6.03 (0.134, 0.101) twenty two Comparative example 4 E4 5.73 6.00 (0.134, 0.102) 20 Example 1 1 5.44 6.11 (0.134, 0.101) 34 Example 2 4 5.46 6.21 (0.134, 0.102) 36 Example 3 5 5.63 5.93 (0.134, 0.103) 40 Example 4 9 4.98 6.45 (0.134, 0.100) 39 Example 5 13 5.61 6.39 (0.134, 0.101) 35 Example 6 twenty four 4.77 6.21 (0.134, 0.102) 37 Example 7 16 5.48 6.40 (0.134, 0.103) 37 Example 8 34 5.46 6.32 (0.134, 0.102) 36 Example 9 44 5.65 6.25 (0.134, 0.102) 40 Example 10 57 5.42 6.20 (0.134, 0.103) 45 Example 11 64 5.61 6.25 (0.134, 0.102) 42 Example 12 65 5.44 6.21 (0.134, 0.101) 38 Example 13 78 4.97 6.33 (0.134, 0.100) 41 Example 14 84 5.63 6.24 (0.134, 0.100) 39 Example 15 92 4.71 6.13 (0.134, 0.100) 44 Example 16 100 4.89 6.20 (0.134, 0.101) 40 Example 17 101 4.99 6.21 (0.134, 0.100) 38 Example 18 102 5.63 5.94 (0.134, 0.100) 35 Example 19 105 5.40 6.11 (0.134, 0.102) twenty two Example 20 106 5.37 6.40 (0.134, 0.101) 40 Example 21 119 5.36 6.22 (0.134, 0.102) 39 Example 22 122 5.38 6.20 (0.134, 0.101) 42 Example 23 124 4.95 6.22 (0.134, 0.101) 39 Example 24 135 4.91 6.25 (0.134, 0.101) 37 Example 25 138 4.91 6.13 (0.134, 0.101) 43 Example 26 152 4.97 6.50 (0.134, 0.101) 38 Example 27 159 5.63 6.22 (0.134, 0.100) 42 Example 28 161 5.40 5.94 (0.134, 0.100) 35 Example 29 175 5.37 5.83 (0.134, 0.101) 37 Example 30 181 5.39 6.35 (0.134, 0.101) 41 Example 31 192 5.38 6.20 (0.134, 0.103) 40 Example 32 195 5.39 6.42 (0.134, 0.102) 43 Example 33 196 4.97 6.20 (0.134, 0.101) 38 Example 34 197 4.94 6.23 (0.134, 0.102) 34 Example 35 198 4.90 6.11 (0.134, 0.101) 38 Example 36 202 5.38 6.38 (0.134, 0.101) 39 Example 37 206 5.37 6.22 (0.134, 0.103) 40 Example 38 210 5.38 6.61 (0.134, 0.102) 41 Example 39 217 4.96 6.21 (0.134, 0.101) 37 Example 40 235 4.91 6.22 (0.134, 0.102) 33 Example 41 238 4.90 6.14 (0.134, 0.101) 40 Example 42 248 4.98 6.51 (0.134, 0.101) 39 Example 43 255 5.61 6.21 (0.134, 0.100) 41 Example 44 260 5.39 5.95 (0.134, 0.101) 35 Example 45 264 5.10 6.88 (0.134, 0.100) 41 Example 46 272 5.38 6.39 (0.134, 0.101) 39 Example 47 275 5.37 6.21 (0.134, 0.103) 40 Example 48 277 5.10 6.62 (0.134, 0.102) 43 Example 49 283 4.96 6.22 (0.134, 0.100) 41 Example 50 285 4.98 6.92 (0.134, 0.100) 43 Example 51 287 5.62 5.97 (0.134, 0.100) 39 Example 52 302 4.74 6.53 (0.134, 0.102) 41 Example 53 312 4.72 6.33 (0.134, 0.102) 42 Example 54 318 4.91 6.92 (0.134, 0.100) 45 Example 55 328 4.91 6.95 (0.134, 0.100) 40 Example 56 332 4.96 6.21 (0.134, 0.100) 40 Example 57 342 5.62 5.99 (0.134, 0.100) 36 Example 58 346 5.31 6.53 (0.134, 0.102) 34 Example 59 348 4.79 6.55 (0.134, 0.102) 47 Example 60 355 5.40 6.12 (0.134, 0.101) 39 Example 61 358 5.44 6.10 (0.134, 0.100) 41 Example 62 359 5.38 6.01 (0.134, 0.101) 34 Example 63 368 4.95 6.86 (0.134, 0.100) 45 Example 64 370 4.95 6.95 (0.134, 0.100) 39 Example 65 372 4.98 6.20 (0.134, 0.100) 40 Example 66 387 5.61 5.98 (0.134, 0.100) 33 Example 67 394 4.75 6.43 (0.134, 0.102) 43 Example 68 403 5.40 6.12 (0.134, 0.101) 39 Example 69 406 5.43 6.21 (0.134, 0.100) 40 Example 70 415 5.39 6.26 (0.134, 0.101) 36 Example 71 418 5.39 6.87 (0.134, 0.100) 45 Example 72 427 5.21 6.93 (0.134, 0.100) 44 Example 73 432 5.13 6.95 (0.134, 0.100) 40 Example 74 447 5.03 6.22 (0.134, 0.100) 40 Example 75 453 4.91 5.88 (0.134, 0.100) 33 Example 76 458 4.72 6.43 (0.134, 0.102) 48 Example 77 464 5.47 6.15 (0.134, 0.101) 39 Example 78 473 5.44 6.53 (0.134, 0.102) 49 Example 79 476 5.33 6.53 (0.134, 0.102) 42 Example 80 490 4.91 6.98 (0.134, 0.100) 43 Example 81 497 4.91 6.11 (0.134, 0.100) 35 Example 82 505 4.92 6.22 (0.134, 0.100) 40 Example 83 509 5.63 5.99 (0.134, 0.100) 38 Example 84 517 4.72 6.54 (0.134, 0.102) 48 Example 85 527 4.72 6.33 (0.134, 0.102) 40 Example 86 534 4.63 6.53 (0.134, 0.102) 43 Example 87 536 4.91 6.82 (0.134, 0.100) 41 Example 88 537 4.99 6.95 (0.134, 0.100) 39 Example 89 539 4.94 6.25 (0.134, 0.100) 40 Example 90 542 5.61 5.98 (0.134, 0.100) 33 Example 91 543 5.44 6.53 (0.134, 0.102) 41 Example 92 547 4.88 6.88 (0.134, 0.102) 42 Example 93 551 5.41 6.12 (0.134, 0.101) 40 Example 94 555 5.41 5.89 (0.134, 0.100) 39 Example 95 561 5.39 6.01 (0.134, 0.101) 31 Example 96 567 4.63 6.54 (0.134, 0.102) 48 Example 97 571 4.90 6.82 (0.134, 0.100) 43 Example 98 574 4.72 6.52 (0.134, 0.102) 38 Example 99 575 4.91 6.78 (0.134, 0.100) 42 Example 100 585 4.90 6.94 (0.134, 0.100) 40 Example 101 591 4.99 6.22 (0.134, 0.100) 40 Example 102 594 5.64 5.97 (0.134, 0.100) 33 Example 103 607 5.22 6.01 (0.134, 0.101) 33 Example 104 610 5.39 6.01 (0.134, 0.101) 36 Example 105 614 5.35 6.04 (0.134, 0.101) 33 Example 106 618 4.91 6.94 (0.134, 0.100) 43 Example 107 621 4.77 6.96 (0.134, 0.100) 41 Example 108 627 4.99 6.22 (0.134, 0.100) 40 Example 109 634 5.03 5.98 (0.134, 0.100) 42 Example 110 643 4.71 6.50 (0.134, 0.102) 41 Example 111 650 4.77 6.53 (0.134, 0.102) 48 Example 112 652 4.73 6.59 (0.134, 0.102) 45 Example 113 657 5.42 6.12 (0.134, 0.101) 39 Example 114 667 4.72 6.53 (0.134, 0.102) 37 Example 115 674 4.91 6.78 (0.134, 0.100) 42 Example 116 684 5.45 5.89 (0.134, 0.100) 41 Example 117 687 5.36 6.03 (0.134, 0.101) 32 Example 118 692 4.96 6.83 (0.134, 0.100) 45 Example 119 695 4.94 6.93 (0.134, 0.100) 43 Example 120 700 4.94 6.95 (0.134, 0.100) 41 Example 121 708 5.34 6.13 (0.134, 0.101) 38 Example 122 723 4.86 6.77 (0.134, 0.100) 45 Example 123 729 4.95 6.73 (0.134, 0.102) 42 Example 124 734 4.91 6.55 (0.134, 0.100) 42 Example 125 737 5.31 6.29 (0.134, 0.100) 44 Example 126 739 5.26 6.10 (0.134, 0.100) 34 Example 127 741 5.34 6.25 (0.134, 0.102) 41 Example 128 744 5.31 6.57 (0.134, 0.102) 44 Example 129 746 4.72 6.53 (0.134, 0.102) 38 Example 130 758 4.79 6.54 (0.134, 0.102) 48 Example 131 768 5.41 6.13 (0.134, 0.101) 39 Example 132 781 5.13 5.89 (0.134, 0.100) 41 Example 133 789 5.31 6.03 (0.134, 0.101) 34 Example 134 796 5.19 6.88 (0.134, 0.100) 47 Example 135 802 5.26 6.71 (0.134, 0.100) 39 Example 136 804 5.21 6.66 (0.134, 0.100) 45 Example 137 807 4.94 6.83 (0.134, 0.100) 38 Example 138 813 5.34 6.53 (0.134, 0.100) 46 Example 139 818 5.33 6.04 (0.134, 0.100) 41 Example 140 824 5.11 6.88 (0.134, 0.100) 45 Example 141 826 5.11 6.88 (0.134, 0.100) 45 Example 142 830 5.61 5.92 (0.134, 0.100) 33 Example 143 831 5.44 6.53 (0.134, 0.102) 40 Example 144 844 4.88 6.88 (0.134, 0.102) 42 Example 145 855 5.40 6.12 (0.134, 0.101) 41 Example 146 861 5.44 5.88 (0.134, 0.100) 39 Example 147 877 5.39 6.02 (0.134, 0.101) 31 Example 148 883 4.66 6.54 (0.134, 0.102) 48 Example 149 894 4.90 6.82 (0.134, 0.100) 40 Example 150 902 4.72 6.52 (0.134, 0.102) 38 Example 151 907 4.91 6.77 (0.134, 0.100) 42 Example 152 910 4.93 6.94 (0.134, 0.100) 40 Example 153 917 4.99 6.22 (0.134, 0.100) 40 Example 154 918 5.44 5.89 (0.134, 0.100) 41 Example 155 919 5.36 6.03 (0.134, 0.101) 38 Example 156 920 4.97 6.83 (0.134, 0.100) 45 Example 157 923 4.94 6.96 (0.134, 0.100) 44 Example 158 925 4.92 6.95 (0.134, 0.100) 39 Example 159 926 5.19 6.88 (0.134, 0.100) 47 Example 160 927 5.49 6.16 (0.134, 0.101) 39 Example 161 928 5.44 6.53 (0.134, 0.102) 48 Example 162 932 5.37 6.53 (0.134, 0.102) 42 Example 163 936 4.91 6.96 (0.134, 0.100) 44 Example 164 937 4.90 6.11 (0.134, 0.100) 35 Example 165 943 4.92 6.22 (0.134, 0.100) 42 Example 166 945 5.64 5.99 (0.134, 0.100) 38 Example 167 950 4.72 6.55 (0.134, 0.102) 48 Example 168 952 4.72 6.33 (0.134, 0.102) 41 Example 169 954 4.64 6.53 (0.134, 0.102) 43 Example 170 956 4.91 6.82 (0.134, 0.100) 43 Example 171 959 4.97 6.95 (0.134, 0.100) 39 Example 172 961 4.94 6.24 (0.134, 0.100) 40 Example 173 962 5.61 5.98 (0.134, 0.100) 34 Example 174 969 5.42 6.53 (0.134, 0.102) 41 Example 175 971 4.88 6.88 (0.134, 0.102) 45 Example 176 977 5.40 6.12 (0.134, 0.101) 40 Example 177 978 5.41 5.89 (0.134, 0.100) 39 Example 178 980 5.38 6.01 (0.134, 0.101) 31 Example 179 986 4.63 6.54 (0.134, 0.102) 46 Example 180 990 4.90 6.81 (0.134, 0.100) 43 Example 181 996 5.48 6.15 (0.134, 0.101) 40 Example 182 998 5.44 6.55 (0.134, 0.102) 49 Example 183 999 5.33 6.53 (0.134, 0.102) 41 Example 184 1002 4.90 6.98 (0.134, 0.100) 43 Example 185 1003 4.91 6.13 (0.134, 0.100) 35 Example 186 1008 4.92 6.22 (0.134, 0.100) 42 Example 187 1012 5.66 5.99 (0.134, 0.100) 38 Example 188 1013 4.72 6.54 (0.134, 0.102) 47 Example 189 1014 4.71 6.33 (0.134, 0.102) 40 Example 190 1016 4.63 6.56 (0.134, 0.102) 43 Example 191 1018 4.91 6.82 (0.134, 0.100) 40 Example 192 1019 4.98 6.95 (0.134, 0.100) 39 Example 193 1020 4.94 6.25 (0.134, 0.100) 42 Example 194 1022 5.64 5.98 (0.134, 0.100) 33 Example 195 1024 5.44 6.53 (0.134, 0.102) 40 Example 196 1026 4.87 6.88 (0.134, 0.102) 42

It can be seen from the results in Table 60 that compared with Comparative Examples 1, 2, 3, and 4, the organic light-emitting device using the electron transfer layer material of the blue organic light-emitting device of the present disclosure has a lower driving voltage and is significantly improved The luminous efficiency and lifetime are improved. This result is believed to be due to the fact that when the disclosed compound of appropriate length and strength is used as the electron transfer layer, the compound in an excited state is produced by receiving electrons under specific conditions, and especially when the compound is When the hetero-skeleton position is formed in an excited state, the excited energy moves to a stable state before the excited hetero-skeleton position undergoes other reactions, and the relatively stable compound can effectively transfer electrons without being decomposed or destroyed. Those that are stable when excited as above are aryl or acene compounds, or polycyclic hetero compounds. Therefore, it is considered that excellent results are obtained in all aspects of drive, efficiency, and life span by the compound of the present disclosure having enhanced electron transfer properties or improved stability.

＜ Experimental example 2＞- Manufacturing organic light-emitting devices

1) Manufacturing organic light-emitting devices

The transparent ITO electrode film obtained from the glass used for OLED (manufactured by Samsung-Corning Co., Ltd.) was washed with trichloroethylene, acetone, ethanol and distilled water ultrasonically for 5 minutes each, and stored in isopropanol, and use.

Next, mount the ITO substrate in the substrate holder of the vacuum depositor, and introduce the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2- TNATA) to the chamber in the vacuum depositor.

Subsequently, the chamber was evacuated until the vacuum degree therein reached 10 ^-6 Torr, and then 2-TNATA was evaporated by applying a current to the cell chamber to deposit a hole injection layer with a thickness of 600 angstroms on the ITO substrate.

Introduce the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) into the other chamber of the vacuum depositor, and then A current is applied to the chamber to evaporate to deposit a hole transfer layer with a thickness of 300 angstroms on the hole injection layer.

After forming the hole injection layer and the hole transfer layer as described above, a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, in a side chamber in a vacuum depositor, the blue light-emitting host material H1 is vacuum-deposited to a thickness of 200 angstroms, and the blue light-emitting dopant material D1 is vacuum-deposited on it relative to the host material. 5%.

Subsequently, the compound of the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transfer layer.

As the electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to have a thickness of 1,000 angstroms to manufacture an OLED.

At the same time, all the organic compounds needed to manufacture OLEDs are purified by vacuum sublimation of each material used in OLED manufacturing at 10 ^-6 Torr to 10 ^-8 Torr.

An organic light-emitting device was manufactured in the same manner as in Experimental Example 2, except that after forming the electron transfer layer E1 with a thickness of 250 angstroms, the compound given in Table 61 below was used to form the electron transfer layer with a thickness of 50 Angstrom barrier layer.

Table 61 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE) and lifetime of the blue organic light-emitting device manufactured according to the present disclosure.

[Table 61] Compound Drive voltage (V) Luminous efficiency (cd/A) CIE (x, y) Life (T95) Comparative example 5 E1 5.70 6.00 (0.134, 0.102) 20 Comparative example 6 E2 5.71 5.98 (0.134, 0.100) twenty two Comparative example 7 E3 5.70 6.03 (0.134, 0.101) twenty two Comparative example 8 E4 5.73 6.00 (0.134, 0.102) 20 Example 197 9 5.45 6.10 (0.134, 0.101) 33 Example 198 16 5.46 6.22 (0.134, 0.102) 36 Example 199 57 5.62 5.93 (0.134, 0.103) 41 Example 200 65 4.98 6.46 (0.134, 0.100) 39 Example 201 78 5.61 6.38 (0.134, 0.101) 35 Example 202 100 4.77 6.21 (0.134, 0.102) 39 Example 203 102 5.47 6.40 (0.134, 0.103) 37 Example 204 119 5.48 6.32 (0.134, 0.102) 39 Example 205 152 5.65 6.26 (0.134, 0.102) 41 Example 206 159 5.41 6.20 (0.134, 0.103) 45 Example 207 181 5.61 6.28 (0.134, 0.102) 41 Example 208 197 5.44 6.21 (0.134, 0.101) 38 Example 209 206 4.97 6.35 (0.134, 0.100) 41 Example 210 210 5.63 6.24 (0.134, 0.100) 38 Example 211 235 4.70 6.13 (0.134, 0.100) 44 Example 212 255 4.89 6.20 (0.134, 0.101) 41 Example 213 277 4.98 6.21 (0.134, 0.100) 38 Example 214 283 5.63 5.94 (0.134, 0.100) 37 Example 215 302 5.41 6.11 (0.134, 0.102) twenty two Example 216 332 5.37 6.43 (0.134, 0.101) 40 Example 217 358 5.36 6.22 (0.134, 0.102) 38 Example 218 372 5.37 6.20 (0.134, 0.101) 42 Example 219 394 4.96 6.22 (0.134, 0.101) 39 Example 220 406 4.91 6.25 (0.134, 0.101) 39 Example 221 415 4.90 6.14 (0.134, 0.101) 43 Example 222 447 4.98 6.50 (0.134, 0.101) 38 Example 223 464 5.63 6.22 (0.134, 0.100) 45 Example 224 527 5.41 5.94 (0.134, 0.100) 35 Example 225 536 5.37 5.84 (0.134, 0.101) 37 Example 226 567 5.39 6.35 (0.134, 0.101) 40 Example 227 591 5.37 6.20 (0.134, 0.103) 40 Example 228 607 5.39 6.43 (0.134, 0.102) 43 Example 229 621 4.97 6.20 (0.134, 0.101) 39 Example 230 643 4.93 6.23 (0.134, 0.102) 34 Example 231 700 4.90 6.13 (0.134, 0.101) 39 Example 232 708 5.38 6.38 (0.134, 0.101) 39 Example 233 734 5.37 6.23 (0.134, 0.103) 40 Example 234 746 5.37 6.61 (0.134, 0.101) 41 Example 235 781 4.96 6.21 (0.134, 0.101) 39 Example 236 826 4.91 6.22 (0.134, 0.102) 33 Example 237 830 4.90 6.14 (0.134, 0.101) 40 Example 238 861 4.98 6.53 (0.134, 0.101) 39 Example 239 883 5.61 6.21 (0.134, 0.100) 43 Example 240 910 5.38 5.95 (0.134, 0.101) 35 Example 241 927 5.10 6.89 (0.134, 0.100) 41 Example 242 936 5.38 6.39 (0.134, 0.101) 38 Example 243 950 5.38 6.21 (0.134, 0.103) 40 Example 244 952 5.10 6.63 (0.134, 0.102) 43 Example 245 959 4.96 6.22 (0.134, 0.100) 40 Example 246 969 4.99 6.92 (0.134, 0.100) 43 Example 247 980 5.62 5.97 (0.134, 0.100) 38 Example 248 990 4.75 6.53 (0.134, 0.102) 41 Example 249 1002 4.72 6.34 (0.134, 0.102) 42 Example 250 1008 4.91 6.92 (0.134, 0.100) 44 Example 251 1014 4.90 6.95 (0.134, 0.100) 40 Example 252 1019 5.37 6.20 (0.134, 0.103) 40 Example 253 1020 5.36 6.22 (0.134, 0.102) 38 Example 254 1026 5.37 5.84 (0.134, 0.101) 37

It can be seen from the results in Table 61 that compared with Comparative Examples 5, 6, 7 and 8, the organic light-emitting device using the hole blocking layer material of the blue organic light-emitting device of the present disclosure has a lower driving voltage and is significantly Improved luminous efficiency and lifetime. The reason for this is that the compound of Chemical Formula 1 of the present application is a bipolar type having both p-type and n-type substituents, and can block hole leakage and effectively trap excitons in the light-emitting layer.

＜ Experimental example 3＞- Manufacturing organic light-emitting devices

1) Manufacturing organic light-emitting devices

The glass substrate was cleaned with distilled water ultrasonic wave, and ITO was applied as a thin film with a thickness of 1500 angstroms on the glass substrate. After cleaning with distilled water, ultrasonically clean the substrate with solvents (such as acetone, methanol, and isopropanol), then dry, and perform UVO treatment in a UV cleaner using UV for 5 minutes. After that, the substrate is transferred to a plasma cleaner (PT), and plasma treatment is performed under vacuum to remove the ITO work function and the remaining thin film, and the substrate is transferred to a thermal deposition device for organic deposition.

On the transparent ITO electrode (anode), an organic material is formed in a 2-stack white organic light emitting device (WOLED) structure. For the first stack, TAPC was first thermally vacuum deposited to a thickness of 300 angstroms to form a hole transfer layer. After forming the hole transfer layer, a light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited by doping FIrpic to TCz1 (host) 8% as a blue phosphorescent dopant. After the electron transfer layer was formed to 400 angstroms using TmPyPB, the charge generation layer was formed to 100 angstroms by doping to 20% of the compound described in Table 62 below.

For the second stack, MoO _{3 was} first thermally vacuum deposited to a thickness of 50 angstroms to form a hole injection layer. The hole transfer layer (common layer) was formed by doping MoO ₃ to TAPC by 20% to 100 angstroms and depositing TAPC to 300 angstroms. By doping the green phosphorescent dopant Ir(ppy) ₃ to TCz1 (host) with 8%, a light-emitting layer was deposited thereon to 300 angstroms, and an electron transfer layer was formed to 600 angstroms using TmPyPB. Finally, by depositing lithium fluoride (LiF) with a thickness of 10 angstroms to form an electron injection layer on the electron transfer layer, and then by depositing an aluminum (Al) cathode with a thickness of 1,200 angstroms to form a cathode on the electron injection layer, To manufacture organic electroluminescence devices.

At the same time, all the organic compounds needed to manufacture OLEDs are purified by vacuum sublimation of each material used in OLED manufacturing at 10 ^-6 Torr to 10 ^-8 Torr.

[Table 62] Compound Drive voltage (V) Luminous efficiency (cd/A) CIE (x, y) Life (T95) Comparative example 9 E1 5.70 6.00 (0.134, 0.102) 20 Comparative example 10 E2 5.71 5.98 (0.134, 0.100) twenty two Comparative example 11 E3 5.70 6.03 (0.134, 0.101) twenty two Comparative example 12 E4 5.73 6.00 (0.134, 0.102) 20 Instance 255 1014 5.45 6.10 (0.134, 0.101) 33 Example 256 1016 5.46 6.22 (0.134, 0.102) 36 Example 257 1018 5.62 5.93 (0.134, 0.103) 41 Example 258 1019 4.98 6.46 (0.134, 0.100) 39 Example 259 1020 5.61 6.38 (0.134, 0.101) 35 Example 260 1022 4.77 6.21 (0.134, 0.102) 39 Example 261 1024 5.47 6.40 (0.134, 0.103) 37 Example 262 1026 5.48 6.32 (0.134, 0.102) 39

It can be seen from the results in Table 62 that, compared with Comparative Examples 9, 10, 11, and 12, the organic electroluminescence device using the charge generation layer material of the 2-stack white organic electroluminescence device of the present disclosure has a lower driving performance. Voltage and improved luminous efficiency.

Such a result is considered to be due to the fact that the compound of the present invention used as an N-type charge generation layer formed from the disclosed framework having appropriate length, strength, and flatness properties and an appropriate hetero compound capable of bonding with metal Doping with alkali metals or alkaline earth metals forms a gap state in the N-type charge generation layer, and electrons generated from the P-type charge generation layer are easily injected into the electron transfer layer through the gap state generated in the N-type charge generation layer. Therefore, it is considered that the P-type charge generation layer advantageously injects and transfers electrons to the N-type charge generation layer, and as a result, the driving voltage is reduced, and the efficiency and lifetime of the organic light-emitting device are improved.

100: substrate 200: anode 300: organic material layer 301: hole injection layer 302: Hole Transfer Layer 303: light-emitting layer 304: hole barrier 305: electron transfer layer 306: electron injection layer 400: Cathode

1 to 4 are diagrams each schematically showing a laminate structure of an organic light emitting device according to an embodiment of the present application.

100: substrate

200: anode

300: organic material layer

400: Cathode

Claims (16)

A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1]

Wherein, in the chemical formula 1, X is O or S; L ₁ and L ₂ are substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroaryl groups; Z ₂ is hydrogen; substituted Or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R"; or -P(=O)RR'; X ₁ to X ₃ Are the same or different from each other, and are each independently N; CR ₃ ; or P; R ₁ and R ₂ are the same or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or Unsubstituted aryl; substituted or unsubstituted heteroaryl; or P(=O)RR'; R ₃ is hydrogen; halogen; substituted or unsubstituted alkyl; substituted or unsubstituted Substituted aryl; substituted or unsubstituted heteroaryl; or P(=O)RR'; R _a and R _b are the same or different from each other and are each independently selected from the group consisting of: hydrogen; Deuterium; halo; -CN; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted alkoxy; Substituted or unsubstituted cycloalkyl; substituted or unsubstituted heterocycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; -SiRR'R";- P(=O)RR'; and unsubstituted or substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl substituted amine group, Or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring; R, R'and R" are the same or different from each other, and are each independently hydrogen Deuterium; -CN; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; m Is an integer from 0 to 4; p and n are an integer from 0 to 3; q is an integer from 0 to 3; s is an integer from 1 to 4; and when q is an integer of 0 and Z ₂ is hydrogen, n is 2 Or an integer of 3, and R _b is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a Substituted or unsubstituted aliphatic or aromatic hydrocarbon ring. The heterocyclic compound described in item 1 of the scope of the patent application, wherein "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: C1-C60 straight chain or Branched chain alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkane C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 Monocyclic or polycyclic arylamines; and C2 to C60 monocyclic or polycyclic heteroarylamines, or unsubstituted, or substituted by a substituent connecting two or more substituents selected from the above substituents , Or unsubstituted; and R, R'and R" have the same definitions as in Chemical Formula 1. The application of the heterocyclic compound of patentable scope of item 1, wherein R _a and R _b is hydrogen. The heterocyclic compound described in item 1 of the scope of the patent application, wherein R ₁ and R ₂ are hydrogen; unsubstituted or selected from the group consisting of C1 to C40 alkyl groups and C2 to C40 heteroaryl groups or C6 to C40 aryl groups substituted by multiple substituents; P(=0)RR'; or C2 to C40 N-containing heteroaryl groups. The heterocyclic compound described in the first item of the scope of the patent application, wherein L ₁ and L ₂ are C6 to C30 arylene groups; or C2 to C30 heteroaryl groups; and Z ₂ is hydrogen; C6 to C40 aryl groups; or C2 to C40 heteroaryl. The heterocyclic compound described in item 1 of the scope of patent application, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 2 to Chemical Formula 5: [Chemical Formula 2]

[Chemical formula 3]

[Chemical formula 4]

[Chemical formula 5]

In Chemical Formula 2 to Chemical Formula 5, X ₁ to X ₃ , R ₁ , R ₂ , L ₁ , L ₂ , Z ₂ and p have the same definitions as in Chemical Formula 1, and q and s are each an integer from 1 to 3 . The heterocyclic compound described in item 1 of the scope of patent application, wherein Chemical Formula 1 is represented by any of the following Chemical Formula 6 to Chemical Formula 11: [Chemical Formula 6]

[Chemical formula 7]

[Chemical formula 8]

[Chemical formula 9]

[Chemical formula 10]

[Chemical formula 11]

In Chemical Formula 6 to Chemical Formula 11, X ₁ to X ₃ , R ₁ , R ₂ , L ₁ and p have the same definitions as in Chemical Formula 1. The heterocyclic compound described in item 1 of the scope of the patent application, wherein the chemical formula 1 is represented by any of the following compounds:

. An organic light emitting device, including: First electrode The second electrode is arranged opposite to the first electrode; and One or more organic material layers arranged between the first electrode and the second electrode, Wherein, one or more of the organic material layers include the heterocyclic compound described in any one of items 1 to 8 in the scope of the patent application. The organic light-emitting device according to claim 9, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. The organic light-emitting device according to claim 9, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound. The organic light-emitting device according to claim 9, wherein the organic material layer includes an electron injection layer or an electron transfer layer, and the electron injection layer or the electron transfer layer includes the heterocyclic compound. The organic light-emitting device according to claim 9, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound. The organic light-emitting device described in item 9 of the scope of patent application further includes one, two or more layers selected from the following group: light-emitting layer, hole injection layer, hole transfer layer, electron injection layer , Electron transfer layer, electron blocking layer and hole blocking layer. The organic light-emitting device described in item 9 of the scope of patent application includes: First electrode A first stack, which is disposed on the first electrode and includes a first light-emitting layer; A charge generation layer, arranged on the first stack; A second stack, which is disposed on the charge generation layer and includes a second light-emitting layer; and The second electrode is arranged on the second stack. The organic light-emitting device described in claim 15, wherein the charge generation layer includes the heterocyclic compound.

Images