Various host materials and organic electroluminescent devices comprising the same

Abstract

The present disclosure relates to a plurality of host materials including a first host compound represented by Formula 1 and a second host compound represented by Formula 2, and to an organic electroluminescent device including the plurality of host materials. By including a specific combination of the compounds as a host material, an organic electroluminescent device having a low driving voltage, high luminous efficiency, and / or long lifespan can be provided, compared to a conventional organic electroluminescent device.

Description

TECHNICAL FIELD

[0001] The present disclosure relates to a plurality of host materials and an organic electroluminescent device including the same. BACKGROUND

[0002] A TPD / Alq3 double-layer small-molecule organic electroluminescent device (OLED) having green emission composed of a light-emitting layer and a charge transport layer was first developed by Tang et al. of Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has rapidly commercialized. At present, organic electroluminescent devices mainly include phosphorescent materials having excellent light-emitting efficiency in panel implementation. For long-time use and high resolution of displays, there is a need for OLEDs having high light-emitting efficiency and / or long lifespan.

[0003] US 2014 / 0231769 A1 discloses a plurality of host materials using a dibenzofuran or dibenzothiophene derivative compound; however, there is still a need to develop to improve the performance of OLEDs. SUMMARY

[0004] TECHNICAL PROBLEM

[0005] The object of the present disclosure is to provide an organic electroluminescent device having a low driving voltage, high light-emitting efficiency, and / or long lifespan by including a specific combination of compounds as a host material.

[0006] SOLUTION TO PROBLEM

[0007] The present inventors have found that the above object can be achieved by a plurality of host materials including a first host material including a compound represented by the following Formula 1 and a second host material including a compound represented by the following Formula 2, thereby completing the present invention.

[0008]

[0009] In Formula 1,

[0010] Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of N, O, and S, or -NX9X 10 ;

[0011] L1represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

[0012] X1to X8each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, -NX 11 X 12 , or -SiX 13 X 14 X 15 ; or two or more adjacent substituents from X1to X8may be linked to each other to form a ring; provided that at least one of X1and X2, X2and X3, X3and X4, X4and X5, X5and X6, X6and X7, and X7and X8are linked to each other to form a substituted or unsubstituted monocyclic ring or a polycyclic ring having 2 to 5 rings;

[0013] X9and X 10 each independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; and

[0014] X 11 to X 15 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; or can be linked to an adjacent substituent to form a ring.

[0015]

[0016] In Formula 2,

[0017] X represents -O- or -S-;

[0018] HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen atom;

[0019] L2represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

[0020] R1and R2each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyl-di(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or can be linked to an adjacent substituent(s) to form a ring; and

[0021] a represents an integer of 1 to 4, b represents an integer of 1 to 3, and when a and b are 2 or more, each of R1and each of R2may be the same or different.

[0022] Advantages of the Invention

[0023] By including a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device having a low driving voltage, high luminous efficiency, and / or long lifespan, as compared with a conventional organic electroluminescent device, can be provided, and a display device or a lighting device using the same can be manufactured. DETAILED DESCRIPTION

[0024] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the application, and is not meant in any way to restrict the scope of the application.

[0025] Herein, the term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0026] In this context, "a plurality of organic electroluminescent materials" means organic electroluminescent materials in which two or more compounds can be contained in any layer constituting an organic electroluminescent device. It can mean both materials before being contained in an organic electroluminescent device (e.g., before vapor deposition) and materials after being contained in an organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of organic electroluminescent materials can be a combination of two or more compounds contained in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two or more compounds can be included in the same or different layers, and can be mixed-vaporized or co-vaporized, or can be vaporized separately.

[0027] In this context, "a plurality of host materials" means an organic electroluminescent material containing a combination of at least two compounds. It can mean both materials before being contained in an organic electroluminescent device (e.g., before vapor deposition) and materials after being contained in an organic electroluminescent device (e.g., after vapor deposition). The plurality of host materials of the present disclosure can be contained in any light-emitting layer constituting an organic electroluminescent device. The at least two compounds contained in the plurality of host materials can be contained together in one light-emitting layer, or can each be contained in a separate light-emitting layer. When the at least two compounds are contained in one light-emitting layer, the at least two compounds can be mixed-vaporized or co-vaporized, or can be vaporized separately to form a layer.

[0028] In this document, "(C1-C30)alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C3-C30)cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7-membered)heterocyclic alkyl" is a cycloalkyl group having 3 to 7 cyclic skeleton atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. "(C6-C30)aryl" or "(C6-C30)arylene" is a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may contain a spirostructure. Specific examples of aryl groups include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[a]fluorenyl, diphenylbenzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, benzo[a]phenanthrene, phenylphenanthrene, anthracene, benzo[a]anthrene, indene, triphenylene, pyrene, tetraphenyl, perylene, etc. Benzyl, benzo[ Aryl, naphthyl, fluoranthyl, benzofluoranthyl, tolyl, xylyl, mesitylene, isopropylphenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulene, etc. More specifically, aryl can be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3 ... Triphenyl-2-yl, meta-tetraphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, 1- yl, 2- yl, 3- yl, 4- yl, 5- yl, 6- yl, benzo[c]phenanthryl, benzo[g] group consisting of B, N, O, S, Si, P, and Ge. The number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20, and the number of heteroatoms is preferably 1 to 4. The above heteroaryl group can be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; and can be partially saturated. Further, the above heteroaryl group or heteroarylene group can be a heteroaryl group or heteroarylene group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and can include a spiro structure. Examples of the heteroaryl group can specifically include monocyclic-type heteroaryl groups including furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and condensed ring-type heteroaryl groups including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, diphenzo-3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1- isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6- isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5- quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3- isoisoquinolinyl, 4-isoisoquinolinyl, 5-isoisoquinolinyl, 6-isoisoquinolinyl, 7- isoisoquinolinyl, 8-isoisoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1- carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1- phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6- phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10- phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2- oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2- thienyl, 3-thienyl, 2-methylpyrrolyl-1-, 2-methylpyrrolyl-3-, 2-methylpyrrolyl-4-, 2- methylpyrrolyl-5-, 3-methylpyrrolyl-1-, 3-methylpyrrolyl-2-, 3-methylpyrrolyl-4-, 3- methylpyrrolyl-5-, 2-t-butylpyrrolyl-4-, 3-(2-phenylpropyl)pyrrolyl-1-, 2-methyl-1- indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1- indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1- dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1- dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4- dibenzothiophenyl, 1-silafuran, 2-silafuran, 3-silafuran, 4-silafuran, 1-germafuranyl, 2-germafuranyl, 3-germafuranyl, 4-germafuranyl, and the like. In this text, "halogen" includes F, Cl, Br, and I.

[0029] Further, "ortho (o)", "meta (m)", and "para (p)" mean the position of substitution with respect to all substituents. The ortho position is a compound having substituents adjacent to each other, for example, at the 1- and 2-positions on benzene. The meta position is the next substitution position from the immediately adjacent substitution position, for example, a compound has substituents at the 1- and 3-positions on benzene. The para position is the next substitution position from the meta position, for example, a compound has substituents at the 1- and 4-positions on benzene.

[0030] Further, "substituted or unsubstituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent. The substituents of substituted alkyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl, substituted aralkyl, substituted heteroaryl, substituted heteroaralkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, and substituted alkylarylamino are each independently at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino-substituted or unsubstituted (3- to 50-membered)heteroaryl; at least one of cyano, (C1-C30)alkyl, (3- to 50-membered)heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)arylsilyl-substituted or unsubstituted (C6-C30)aryl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl. Preferably, the substituents can be at least one selected from the group consisting of (C1-C20)alkyl; at least one of (C1-C20)alkyl, (3- to 30-membered)heteroaryl, and di(C6-C25)arylamino-substituted or unsubstituted (C6-C25)aryl; at least one of (C1-C20)alkyl and (C6-C25)aryl-substituted or unsubstituted (3- to 30-membered)heteroaryl; and di(C6-C20)arylamino.More preferably, the substituent may be at least one selected from the group consisting of: (C1-C10)alkyl; at least one of (C1-C10)alkyl, (5- to 20-membered)heteroaryl and di(C6-C18)arylamino substituted or unsubstituted (C6-C20)aryl; at least one (C6-C18)aryl substituted or unsubstituted (5- to 25-membered)heteroaryl; and di(C6-C18)arylamino. For example, these substituents can be at least one of the following: methyl; tert-butyl; pyridyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinoxalinyl, biphenylquinoxalinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, and at least one diphenylamino-substituted or unsubstituted phenyl group; at least one diphenyltriazinyl-substituted or unsubstituted naphthyl group; biphenyl; naphthylphenyl; phenylnaphthyl; terphenyl; dimethylfluorenyl; phenylfluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; phenanthreneyl; benzophenanthreneyl; pyridyl; and at least one triazinyl group substituted with phenyl and naphthyl. ; at least one phenyl-substituted indolyl; at least one phenyl-substituted benzimidazolyl; quinolinyl; at least one of phenyl and biphenyl-substituted quinazolinyl; at least one phenyl-substituted quinoxalinyl; at least one phenyl-substituted or unsubstituted carbazoleyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthothiophenyl; at least one phenyl-substituted or unsubstituted benzocarbazoyl; dibenzocarbazoyl; benzophenanthrenethiophenyl; diphenylamino; dimethylfluorenylphenylamino; and substituted or unsubstituted (16- to 33-membered) heteroaryl groups containing at least one of N, O, and S.

[0031] In this document, "a ring formed by the connection of adjacent substituents" means a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof formed by connecting or fused two or more adjacent substituents; preferably, it can be a substituted or unsubstituted (3-membered to 26-membered), more preferably a substituted or unsubstituted (5-membered to 20-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P (preferably N, O, and S).

[0032] In this context, the heteroaryl, heteroarylene, and heterocycloalkyl groups can each independently contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P. Further, the heteroatom can be connected with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, and a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0033] In Formula 1, Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of N, O, and S, or -NX9X 10 According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl containing at least one of N, O, and S, or -NX9X 10 According to another embodiment of the present disclosure, Ar represents at least one (C1-C10)alkyl-substituted or unsubstituted (C6-C25)aryl; at least one (C6-C18)aryl-substituted, unsubstituted, or containing at least one of N, O, and S (5- to 25-membered)heteroaryl; or -NX9X 10. Specifically, Ar can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinazolyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthylidinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo fluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl, or -NX9X 10 . For example, Ar can be phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, pyridyl substituted with phenyl, triazinyl substituted with at least one phenyl, pyrimidinyl substituted with at least one phenyl, quinolyl substituted with phenyl, quinazolyl substituted with at least one of phenyl and naphthyl, quinoxalyl substituted with at least one of phenyl and naphthyl, naphthylidinyl substituted with at least one phenyl, dibenzofuranyl, dibenzothiophenyl, benzofuropyrimidinyl substituted with at least one phenyl, carbazolyl substituted or unsubstituted with at least one phenyl, benzoquinoxalyl substituted with at least one phenyl, benzoquinazolyl substituted with at least one phenyl, or -NX9X 10 .

[0034] X9and X 10 each independently represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl. According to one embodiment of the present disclosure, X9and X 10 each independently represents substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, X9and X 10 each independently represents (C6-C18)aryl substituted or unsubstituted (C6-C18)aryl, or (C6-C18)aryl substituted or unsubstituted (5- to 20-membered)heteroaryl. For example, X9and X 10 each independently can be phenyl, naphthyl, biphenyl, naphthylphenyl, or phenyl substituted or unsubstituted carbazolyl.

[0035] In Formula 1, L1represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene. According to one embodiment of the present disclosure, L1represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene. According to another embodiment of the present disclosure, L1represents a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (5- to 20-membered)heteroarylene. For example, L1may be a single bond, a phenylene, a naphthylene, a biphenylene, a carbazolyiene, a quinazolyiene, a quinoxalyiene, a phenanthrofurazolyiene, a naphthrylene, a benzoquinoxalyiene, a quinolyiene, or a benzoquinazolyiene.

[0036] In Formula 1, X1to X8each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NX 11 X 12 , or -SiX 13 X 14 X 15 ; or two or more adjacent substituents from among X1to X8may be linked to each other to form a ring; provided that at least one of X1and X2, X2and X3, X3and X4, X4and X5, X5and X6, X6and X7, and X7and X8are linked to each other to form a substituted or unsubstituted monocyclic ring or a polycyclic ring having 2 to 5 rings. According to one embodiment of the present disclosure, X1to X8each independently represent hydrogen; or two or more adjacent substituents from among X1to X8may be linked to each other to form a ring; provided that at least one of X1and X2, X2and X3, X3and X4, X4and X5, X5and X6, X6and X7, and X7and X8are linked to each other to form a substituted or unsubstituted monocyclic ring or a polycyclic ring having 2 to 5 rings. For example, X1to X8each independently can be hydrogen; two or more adjacent substituents from among X1to X8may be linked to each other to form a benzene ring, an indole ring substituted with a phenyl, a naphthyl, a biphenyl, or a terphenyl, or a benzoindole ring substituted with a phenyl.

[0037] X 11 to X 15each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or can be linked to an adjacent substituent(s) to form a ring.

[0038] According to one embodiment of the present disclosure, the compound represented by Formula 1 can be represented by any one of the following Formulae 1-1 to 1-5.

[0039]

[0040]

[0041] In Formulae 1-1 to 1-5, Ar and L1are as defined in Formula 1, and each V independently represents CX 18 X 19 , NX 20 , O, or S. According to one embodiment of the present disclosure, V represents NX 20 .

[0042] X 18 to X 31 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. According to one embodiment of the present disclosure, X 18 to X 20 each independently represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, and X 21 to X 31 each independently represent hydrogen or deuterium. According to another embodiment of the present disclosure, X 18 to X 20each independently represents an unsubstituted (C6-C18)aryl group, and X 21 to X 31 each independently represents hydrogen or deuterium. For example, X 18 to X 20 each independently can be phenyl, naphthyl, biphenyl, or terphenyl, and X 21 to X 31 each independently can be hydrogen.

[0043] f, g, j, k, l, and m each independently represent an integer of 1 to 4; c to e, h, and i each independently represent an integer of 1 to 6, and each X 21 to X 31 may be the same or different.

[0044] According to one embodiment of the present disclosure, Formula 1-5 can be excluded from the case of Formula 1-6.

[0045]

[0046] In Formula 1-6, Ar, L1, V, X 30 , X 31 , l, and m are as defined in Formula 1-5.

[0047] In Formula 2, X represents -O- or -S-.

[0048] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen atom. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5- to 25-membered)heteroaryl containing at least one nitrogen atom. According to another embodiment of the present disclosure, HAr represents at least one of a (C6-C18)aryl and a (5- to 25-membered)heteroaryl substituted with a (3- to 20-membered)heteroaryl containing at least one nitrogen atom. Specifically, HAr can be a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthrydinyl, a substituted or unsubstituted benzothienopyrimidinyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted pyridopyrazinyl. For example, HAr can be a substituted quinoxalinyl, a substituted quinazolinyl, a substituted naphthrydinyl, a substituted carbazolyl, a substituted pyridopyrazinyl, a substituted benzoquinoxalinyl, a substituted benzoquinazolinyl, or a substituted triazinyl; and wherein the substituents of the substituted quinoxalinyl, the substituted quinazolinyl, the substituted naphthrydinyl, the substituted carbazolyl, the substituted pyridopyrazinyl, the substituted benzoquinoxalinyl, the substituted benzoquinazolinyl, and the substituted triazinyl can be at least one of a phenyl, a phenyl substituted with a carbazolyl, a phenyl substituted with a diphenylamino, a phenyl substituted with a benzquinoxalinyl, a phenyl substituted with a diphenylfuranyl, a phenyl substituted with a diphenylthiophenyl, a naphthyl, a phenylnaphthyl, a naphthylphenyl, a biphenyl, a terphenyl, a dimethylfluorenyl, a dimethylbenzofluorenyl, a phenanthryl, a triphenylenyl, a carbazolyl substituted with a phenyl, a diphenylfuranyl, and a diphenylthiophenyl.

[0049] In Formula 2, L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene. According to one embodiment of the present disclosure, L2 represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene. According to another embodiment of the present disclosure, L2 represents a single bond, a (C6-C18)aryl-substituted or unsubstituted (C6-C20)arylene, or an unsubstituted (5- to 20-membered)heteroarylene. For example, L2 can be a single bond, a phenylene, a naphthylene, a biphenylene, a phenylnaphthylene, a naphthylphenylene, or a naphthrydylene.

[0050] In Formula 2, R1and R2each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyl-di(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or can be linked to an adjacent substituent to form a ring. For example, two R1, two R2, and / or R1and R2may be linked to each other to form a ring. In another embodiment of the disclosure, R1and R2each independently can be hydrogen or deuterium.

[0051] In Formula 2, a represents an integer of 1 to 4, b represents an integer of 1 to 3, and each R1and each R2may be the same or different when a and b are 2 or more.

[0052] According to one embodiment of the disclosure, the compound represented by Formula 2 can be represented by at least one of the following Formulae 2-1 or 2-2.

[0053]

[0054] In Formulae 2-1 and 2-2, X, R1, R2, L2, a, and b are as defined in Formula 2.

[0055] In Formula 2-2, the A ring is a substituted or unsubstituted (6- to 10-membered) ring. According to one embodiment of the disclosure, the A ring can be a (C6-C18)aryl or (5- to 20-membered)heteroaryl-substituted or unsubstituted (6- to 10-membered)monocyclic or polycyclic ring. For example, the A ring can be a benzene ring; a naphthalene ring; a phenyl, biphenyl, naphthyl, dimethylfluorenyl, dimethylbenzofluorenyl, or phenylcarbazolyl-substituted or unsubstituted pyridine ring; or a phenyl-substituted pyrazine ring, etc.

[0056] In Formulae 2-1 and 2-2, Y1to Y5, and Y 11 to Y 13 each independently represent N or CR3.

[0057] R3each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (3- to 30-membered)heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyl-di(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino group, a substituted or unsubstituted mono- or di- (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or adjacent R3may be linked to each other to form a ring. According to one embodiment of the present disclosure, R3each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl group, a substituted or unsubstituted (C6-C25)aryl group, or a substituted or unsubstituted (5- to 25-membered)heteroaryl group. According to another embodiment of the present disclosure, R3each independently represents at least one of hydrogen, deuterium, a (C1-C10)alkyl group, and a (3- to 20-membered)heteroaryl-substituted or unsubstituted (C6-C20)aryl group, or a (C6-C18)aryl-substituted or unsubstituted (5- to 20-membered)heteroaryl group. For example, R3each independently can be hydrogen, a substituted or unsubstituted phenyl group, a naphthyl group, a dimethylfluorenyl group, a phenanthryl group, a naphthylphenyl group, a phenylnaphthyl group, a dimethylbenzofluorenyl group, a terphenyl group, a triphenylenyl group, a carbazolyl group substituted with a phenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, wherein the substituent of the substituted phenyl group can be at least one of a carbazolyl group, a diphenylamino group, a phenylquinoxalinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

[0058] The compound represented by Formula 1 can be illustrated by, but is not limited to, the following compounds.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] The compound represented by Formula 2 can be illustrated by, but is not limited to, the following compounds.

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] At least one C1-1 to C1-145 and at least one C2-1 to C2-275 can be combined and used in an organic electroluminescent device. According to one embodiment of the disclosure, at least one compound represented by Formula 1-3 and at least one compound represented by Formula 2-1 can be combined and used in an organic electroluminescent device.

[0078] The organic electroluminescent compound according to another embodiment of the disclosure can be represented by the following Formula 2-1-1.

[0079]

[0080] In Formula 2-1-1,

[0081] X a represents O or S;

[0082] L a represents an unsubstituted naphthalene group other than a 1,2-naphthalene group; and

[0083] Ar a and Ar b each independently represents an unsubstituted phenyl group, an unsubstituted naphthalene group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, or a combination thereof.

[0084] According to one embodiment of the disclosure, L arepresents an unsubstituted naphthylene group except for a 1,2-naphthylene group, for example, L a may be represented by any substituent listed in the following Group 1.

[0085] [Group 1]

[0086]

[0087] wherein * represents a connecting position with an adjacent ring in Formula 2-1-1.

[0088] According to one embodiment of the present disclosure, Ar a and Ar b each independently represents an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, or a combination thereof, preferably, each independently represents an unsubstituted phenyl group, an unsubstituted ortho-biphenyl group, an unsubstituted meta-biphenyl group, an unsubstituted para-biphenyl group, an unsubstituted naphthyl group, an unsubstituted meta-terphenyl group, or an unsubstituted para-terphenyl group.

[0089] The compound represented by Formula 2-1-1 can be illustrated by the following compounds, but is not limited thereto.

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] According to one embodiment of the present disclosure, in the organic electroluminescent device, the compound represented by Formula 2-1-1 can be used as a single compound or in a combination of two or more compounds.

[0096] The compound represented by Formula 1 according to the present disclosure can be produced by the following Reaction Scheme 1, and can be produced by a synthetic method known to one skilled in the art, for example, can be produced by referring to the methods disclosed in KR 2015-0135109 A (2015.12.02.), KR 2016-0099471 A (2016.08.22.), KR 2015-0077513 A (2015.07.08.), and KR 2017-0129599 A (2017.11.27.), but is not limited thereto.

[0097] [Reaction Scheme 1]

[0098]

[0099] In Reaction Scheme 1, Ar, L1, X 20 , X 27 to X 29 , i, j, and k are as defined in Formula 1-4.

[0100] The compound represented by Formula 2 of the present disclosure can be produced by the following Reaction Scheme 2 and synthetic methods known to one skilled in the art, but is not limited thereto.

[0101] [Reaction Scheme 2]

[0102]

[0103] In Reaction Scheme 2, X, HAr, L2, R1, R2, a, and b are as defined in Formula 2.

[0104] The organic electroluminescent device according to the present disclosure includes an anode; a cathode; and at least one organic layer interposed between the anode and the cathode. The organic layer can include a plurality of host materials including the compound represented by Formula 1 as a first organic electroluminescent light-emitting material and the compound represented by Formula 2 as a second organic electroluminescent light-emitting material. According to one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one light-emitting layer interposed between the anode and the cathode. The at least one light-emitting layer can include the compound represented by Formula 1 and the compound represented by Formula 2. According to another embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one light-emitting layer interposed between the anode and the cathode. The at least one light-emitting layer can include the compound represented by Formula 2-1-1.

[0105] The light-emitting layer includes a host and a dopant material, and the host includes a plurality of host materials. Among the plurality of host materials, the compound represented by Formula 1 is included as a first host compound, and the compound represented by Formula 2 is included as a second host compound. Herein, the weight ratio of the first host compound to the second host compound can be about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, more preferably about 50:50.

[0106] In the present disclosure, the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer in which two or more layers are stacked. In the various host materials of the present disclosure, the first host material and the second host material can be included together in one light-emitting layer, or can be included each in a separate light-emitting layer. According to one embodiment of the present disclosure, the doping concentration of the dopant compound, which can be a host compound-based dopant compound, can be less than 20 wt%. According to another embodiment of the present disclosure, the light-emitting layer can contain only the compound represented by Formula 2-1-1.

[0107] The organic electroluminescent device of the present disclosure can further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure can contain, in addition to the various host materials of the present disclosure, an amine-based compound as at least one of a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, and an electron blocking material. Further, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure can contain, in addition to the various host materials of the present disclosure, an azine-based compound as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0108] The dopant included in the organic electroluminescent material of the present disclosure can be at least one phosphorescent dopant or a fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably one or more metalated complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more ortho-metalated complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably one or more ortho-metalated iridium complex compounds.

[0109] The dopant included in the organic electroluminescent device can use a compound represented by the following Formula 101, but is not limited thereto:

[0110]

[0111] In Formula 101,

[0112] wherein L is selected from the following Structure 1 or 2:

[0113]

[0114] R 100 to R 107each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3- to 30-membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; or can be linked to an adjacent substituent(s) to form a ring, for example, R 100 to R 103 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofurodipyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indoquinoline, R 104 to R 107 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indopyridine, a substituted or unsubstituted benzofurodipyridine, or a substituted or unsubstituted benzothienopyridine;

[0115] R 201 to R 211 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted (C6-C30)aryl; or can be linked to an adjacent substituent(s) to form a ring; and

[0116] n' represents an integer of 1 to 3.

[0117] Specifically, specific examples of the dopant compound include the following, but are not limited thereto.

[0118]

[0119]

[0120]

[0121]

[0122] According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one light-emitting layer interposed between the anode and the cathode, wherein the at least one light-emitting layer can include a plurality of host materials of the present disclosure and a compound represented by the following formula 3.

[0123]

[0124] In formula 3, R11 to R 13 each independently represent a substituted or unsubstituted (C1-C5)alkyl group, and R 14 represent a substituted or unsubstituted (C1-C5)alkyl group or a (C1-C5)alkyl-substituted or unsubstituted phenyl group.

[0125] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc., can be used.

[0126] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and is not problematic in terms of film-forming ability.

[0127] Further, the compound represented by Formula 1 and the compound represented by Formula 2 can be formed by the methods listed above. Generally, when forming a layer, co-evaporation or mixed evaporation can be used. Co-deposition is a mixed deposition method in which two or more isomer materials are put into respective single crucible sources and an electric current is applied to two cells at the same time to evaporate the materials and perform mixed deposition; and mixed deposition is a mixed deposition method in which two or more isomer materials are mixed in one crucible source before depositing them and then an electric current is applied to one cell to evaporate the materials.

[0128] A display device can be provided by including the plurality of host materials of the present disclosure. Further, a display device or a lighting device can be manufactured using the organic electroluminescent device of the present disclosure. Specifically, the organic electroluminescent device of the present disclosure can be used to manufacture a display device such as a smart phone, a tablet, a notebook computer, a PC, a TV, or a display device of a vehicle, or a lighting device such as outdoor or indoor lighting.

[0129] Hereinafter, the luminous efficiency and lifespan characteristics of the OLED according to the present disclosure will be explained; however, the following examples are intended to explain the present invention in order to understand the present disclosure in detail, and are not limited thereto.

[0130] [Example 1] Preparation of Compounds C1-128

[0131]

[0132] 1) Synthesis of Compound 1

[0133] Compound 1 (76 g, 220 mmol), iodobenzene (90 g, 439 mmol), CuI (20.90 g, 110 mmol), ethylenediamine (EDA) (13 g, 110 mmol), and K3PO4 (139 g, 659 mmol) were added to 1.1 L of toluene and refluxed for 2.5 hours. Thereafter, MeOH was added, and the resulting solid was filtered under reduced pressure. Then, the remaining product was purified by column chromatography to obtain Compound 2 (55.1 g, yield: 60%).

[0134] 2) Synthesis of Compound 2

[0135] Compound 1 (76 g, 220 mmol), iodobenzene (90 g, 439 mmol), CuI (20.90 g, 110 mmol), ethylenediamine (EDA) (13 g, 110 mmol), and K3PO4 (139 g, 659 mmol) were added to 1.1 L of toluene and refluxed for 2.5 hours. Thereafter, MeOH was added, and the resulting solid was filtered under reduced pressure. Then, the remaining product was purified by column chromatography to obtain Compound 2 (55.1 g, yield: 60%).

[0136] 3) Synthesis of Compound 3

[0137] Compound 2 (54.6 g, 129 mmol), 2-chloroaniline (20 g, 155 mmol), Pd(OAc)2 (2.9 g, 13 mmol), P(t-Bu)3 (5.2 g, 26 mmol), and NaOt-Bu (31 g, 323 mmol) were added to 650 mL of toluene and stirred for 4 hours. After cooling to room temperature, NH4Cl (aqueous solution) was added to the mixture. The organic layer was extracted with ethyl acetate and dried with magnesium sulfate, followed by vacuum distillation. Thereafter, the remaining product was purified by column chromatography to obtain Compound 3 (47.9 g, yield: 79%).

[0138] 4) Synthesis of Compound 4

[0139] Compound 3 (48 g, 103 mmol), Pd(OAc)2(2.3 g, 10 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (7.6 g, 21 mmol), and Cs2CO3(100 g, 308 mmol) were added to 400 mL of DMA and stirred for 1 hour. After cooling to room temperature, NH4Cl (aqueous solution) was added to the reaction mixture. Then, the organic layer was extracted with dichloromethane (MC), and the extracted organic layer was dried with magnesium sulfate, followed by vacuum distillation. Thereafter, the remaining product was purified by column chromatography to obtain compound 4 (44 g, yield: 79%).

[0140] 5) Synthesis of compound C1-128

[0141] Compound 4 (5 g, 12 mmol), iodobenzene (3.5 g, 17 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.6 g, 23 mmol), and K3PO4(4.9 g, 23 mmol) were added to 60 mL of o-xylene and refluxed for 1 day. After the completion of the reaction, the mixture was cooled to room temperature, and filtered with a silica filter with dichloromethane (MC), followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane (MC / Hex) to obtain compound C1-128 (1.3 g, yield: 22%).

[0142] 1 H NMR (600 MHz, DMSO, δ) 9.16-9.15 (d, 1H), 8.99-8.98 (d, 1H), 8.14-8.13 (d, 1H), 7.94-7.93 (d, 1H), 7.94-7.68 (m, 9H), 7.65-7.61 (m, 3H), 7.60-7.54 (m, 3H), 7.25-7.21 (m, 2H), 7.08-7.07 (d, 1H), 6.78-6.76 (m, 1H) 5.95-5.94 (d, 1H)

[0143] MW UV PL Melt point C1-128 508.62 342 nm 427 nm 184℃

[0144] [Example 2] Preparation of compound C1-129

[0145]

[0146] Compound 4 (7 g, 16 mmol), 2-bromonaphthalene (6.7 g, 32 mmol), CuI (1.5 g, 8 mmol), 1,2-diaminocyclohexane (3.7 g, 32 mmol), and K3PO4 (10.3 g, 49 mmol) were added to 80 mL of o-xylene and refluxed for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and then filtered with MC through a celite filter, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound C1-129 (1.3 g, yield: 22%).

[0147] 1 H NMR (600 MHz, DMSO, δ) 9.17-9.15 (d, 1H), 9.00-8.99 (d, 1H), 8.31-8.30 (m, 2H), 8.20-8.18 (d, 1H), 8.15-8.14 (d, 1H), 8.11-8.10 (d, 1H), 7.95-7.94 (d, 1H), 7.83-7.79 (m, 5H), 7.73-7.69 (m, 4H), 7.60-7.57 (m, 4H), 7.21-7.18 (m, 2H), 7.14-7.13 (d, 1H), 6.78-6.77 (t, 1H) 5.98-5.96 (d, 1H)

[0148] MW UV PL Melt point C1-129 558.68 340 nm 431 nm 263℃

[0149] [Example 3] Preparation of compound C1-131

[0150]

[0151] 1) Synthesis of compound 14

[0152] Compound 1 (15 g, 220 mmol), 3-iodo-1,1'-biphenyl (18 g, 65 mmol), CuI (4.1 g, 22 mmol), ethylenediamine (EDA) (2.6 g, 43 mmol), and K3PO4 (23 g, 108 mmol) were added to 216 mL of toluene and refluxed for 4 hours. MeOH was added thereto, and the resulting solid was filtered under reduced pressure. The resulting product was purified by column chromatography to obtain compound 14 (16 g, yield: 74%).

[0153] 2) Synthesis of compound 15

[0154] Compound 14 (15 g, 30 mmol), 2-chloroaniline (7.7 g, 60 mmol), Pd(OAc)2(0.67 g, 3 mmol), P(t-Bu)3(1.2 g, 6 mmol) and NaOt-Bu (7.2 g, 75 mmol) were added to 150 mL of toluene and refluxed for 2 hours. After cooling to room temperature, NH4Cl (aqueous solution) was added thereto and then the organic layer was extracted with EA. The extracted organic layer was then dried with magnesium sulfate, followed by vacuum distillation. The resulting product was purified by column chromatography to obtain compound 15 (10.1 g, yield: 62%).

[0155] 3) Synthesis of compound 16

[0156] Compound 15 (10 g, 18 mmol), Pd(OAc)2(0.41 g, 1.8 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.35 g, 3.7 mmol) and Cs2CO3(18 g, 55 mmol) were added to 92 mL of DMA and refluxed for 1 hour. After cooling to room temperature, NH4Cl (aqueous solution) was added thereto and then the organic layer was extracted with MC. The extracted organic layer was then dried with magnesium sulfate, followed by vacuum distillation. The resulting product was purified by column chromatography to obtain compound 16 (7.1 g, yield: 76%).

[0157] 4) Synthesis of compound C1-131

[0158] Compound 16 (6.7 g, 13 mmol), 3-iodo-1,1'-biphenyl (7.4 g, 26 mmol), Cu powder (0.42 g, 7 mmol) and K2CO3(3.6 g, 26 mmol) were added to 70 mL of o-dichlorobenzene and refluxed for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and then filtered with MC through a diatomite filter, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound C1-131 (3.1 g, yield: 36%).

[0159] 1 H NMR (600 MHz, DMSO, δ) 9.18-9.17 (d, 1H), 9.01-9.00 (d, 1H), 8.16-8.15 (d, 1H), 8.11-8.09 (d, 1H), 8.06-8.05 (m, 2H), 8.00-7.79 (m, 7H), 7.73-7.57 (m, 8H), 7.48-7.38 (m, 6H), 7.30-7.28 (t, 1H), 7.22-7.18 (m, 2H), 6.80-6.78 (t, 1H), 6.07-6.06 (d, 1H)

[0160] MW Melt point C1-131 660.82 259℃

[0161] [Example 4] Preparation of compound C1-130

[0162]

[0163] Compound 4 (4 g, 9.25 mmol), 3-iodo-1,1'-biphenyl (3.1 g, 11.1 mmol), Pd2(dba)3(0.42 g, 0.46 mmol), s-phos (0.38 g, 0.92 mmol), and NaOt-Bu (2.2 g, 23.13 mmol) were dissolved in 46 mL of o-xylene and stirred for 1 day. The organic layer was extracted with MC, followed by vacuum distillation. Thereafter, the resulting product was purified by column chromatography with MC / hexane to obtain compound C1-130 (1.2 g, yield: 23%).

[0164] 1 H NMR (600 MHz, DMSO, δ) 9.17-9.15 (d, 1H), 9.00-8.98 (d, 1H), 8.15-8.13 (d, 1H), 8.07-8.06 (d, 1H), 7.98 (m, 1H), 7.95-7.94 (d, 1H), 7.88-7.86 (t, 1H), 7.82-7.80 (m, 7H), 7.71-7.67 (m, 2H), 7.65-7.61 (m, 2H), 7.60-7.55 (m, 2H), 7.49-7.47 (t, 2H), 7.42-7.39 (t, 1H), 7.30-7.27 (t, 1H), 7.26-7.23 (t, 1H), 7.20-7.19 (d, 1H), 6.80-6.77 (t, 1H), 5.97-5.95 (d, 1H)

[0165] MW Melt point C1-130 584.7 249.6℃

[0166] [Example 5] Preparation of compound C1-133

[0167]

[0168] 1) Synthesis of compound 1

[0169] Compound 1 (7.5 g, 0.016 mol), 2-chloro-aniline (2.4 g, 0.019 mol), Pd(OAc)2(0.36 g, 0.002 mol), P(t-Bu)3(0.15 g, 0.003 mol), and NaOt-Bu (3.8 g, 0.04 mol) were added to 80 mL of toluene and stirred at 100 °C for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography to obtain Compound 2 (3.6 g, yield: 43%).

[0170] 2) Synthesis of Compound 2

[0171] Compound 1 (7.5 g, 0.016 mol), 2-chloro-aniline (2.4 g, 0.019 mol), Pd(OAc)2(0.36 g, 0.002 mol), P(t-Bu)3(0.15 g, 0.003 mol), and NaOt-Bu (3.8 g, 0.04 mol) were added to 80 mL of toluene and stirred at 100 °C for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography to obtain Compound 2 (3.6 g, yield: 43%).

[0172] 3) Synthesis of Compound 3

[0173] Compound 2 (5.8 g, 0.011 mol), P(Cy3)HFB4(0.82 g, 0.002 mol), Pd(OAc)2(0.25 g, 0.001 mol), and Cs2CO3(10.9 g, 0.033 mol) were added to 44.4 mL of DMA and stirred for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain Compound 3 (4.2 g, yield: 76%).

[0174] 4) Synthesis of Compound C1-133

[0175] Compound 3 (4.2 g, 0.009 mol), iodobenzene (1.9 mL, 0.017 mol), CuI (0.8 g, 0.004 mol), 1,2-diaminocyclohexane (2 mL, 0.018 mol), and K3PO4(3.7 g, 0.017 mmol) were added to 44 mL of o-xylene and stirred for 1 day. After completion of the reaction, the organic layer was extracted with MC, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain Compound C1-133 (1.2 g, yield: 24%).

[0176] 1 H NMR (600 MHz, DMSO, δ) 9.19-9.07 (d, 1H), 9.01-9.00 (d, 1H), 8.37 (s, 1H), 8.35-8.34 (d, 1H), 8.23-8.22 (d, 1H), 8.15-8.14 (d, 1H), 8.06-8.05 (d, 1H), 7.94-7.92 (m, 2H), 7.78-7.56 (m, 12H), 7.30-7.27 (t, 1H), 7.11-7.09 (t, 1H), 7.05-7.04 (d, 1H), 6.41-6.39 (t, 1H), 5.88-5.86 (d, 1H)

[0177] MW Melt point C1-133 558.7 272.6℃

[0178] [Example 6] Preparation of compounds C1-132

[0179]

[0180] 1) Synthesis of compound 1

[0181] 7H-dibenzo[c,g]carbazole (50 g, 187 mmol) was dissolved in 750 mL of DMF in a flask and cooled to 0°C with stirring. NBS (30 g, 168 mmol) was dissolved in 250 mL of DMF and added dropwise to the mixture for 1 hour. After this, the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, the reaction mixture was washed with Na2S2O3(aqueous solution) and water. After this, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer by using MgSO4. After this, the remaining product was dried and filtered with a silica filter to obtain compound 1 (40 g, yield: 62%).

[0182] 2) Synthesis of compound 2

[0183] Compound 1 (11 g, 32 mmol), 4-iodo-1,1'-biphenyl (17.8 g, 64 mmol), CuI (3.0 g, 15.9 mmol), ethylenediamine (1.91 g, 31.8 mmol), and K3PO4(20.3 g, 95 mmol) were added to 160 mL of toluene and refluxed for 4 hours. After this, MeOH was added thereto and the resulting solid was filtered under reduced pressure. After this, the remaining product was then purified by column chromatography to obtain compound 2 (13.0 g, yield: 82%).

[0184] 3) Synthesis of compound 3

[0185] Compound 2 (13.0 g, 26 mmol), 2-chloroaniline (6.7 g, 52 mmol), Pd(OAc)2(0.59 g, 2.6 mmol), P(t-Bu)3(1.1 g, 5.2 mmol), and NaOt-Bu (6.3 g, 65 mmol) were added to 130 mL of toluene and refluxed for 4 hours. After cooling to room temperature, NH4Cl (aqueous solution) was added to the mixture. Then, the organic layer was extracted with EA, and the extracted organic layer was dried with magnesium sulfate. The resulting solid was distilled under reduced pressure, and purified by column chromatography to obtain compound 3 (9.2 g, yield: 65%).

[0186] 4) Synthesis of compound 4

[0187] Compound 3 (9.2 g, 17 mmol), Pd(OAc)2(0.38 g, 2 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.2 g, 3 mmol), and Cs2CO3(138 g, 42 mmol) were added to 70 mL of DMA and refluxed for 1 hour. After cooling to room temperature, NH4Cl (aqueous solution) was added to the mixture, followed by vacuum distillation. Thereafter, the resulting product was purified by column chromatography to obtain compound 4 (6.0 g, yield: 70%).

[0188] 5) Synthesis of compound C1-132

[0189] Compound 4 (6 g, 12 mmol), 2-bromonaphthalene (4.9 g, 24 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.7 g, 24 mmol), and K3PO4(7.5 g, 35 mmol) were added to 60 mL of o-xylene and stirred for 1 day. After cooling to room temperature, the organic layer was extracted with ethyl acetate and water, and the extracted organic layer was dried with magnesium sulfate. The mixture was filtered with MC through a diatomite filter, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound C1-132 (2.1 g, yield: 28%).

[0190] 1H NMR (600 MHz, DMSO, δ) 9.18-9.17 (d, 1H), 9.01-8.99 (d, 1H), 8.33-8.31 (m, 2H), 8.20-8.19 (d, 1H), 8.17-8.15 (d, 1H), 8.12-8.08 (m, 3H), 7.98-7.97 (d, 1H), 7.93-7.89 (m, 4H), 7.70-7.68 (m, 5H), 7.63-7.57 (m, 5H) 7.50-7.48 (t, 1H), 7.22-7.19 (t, 1H), 7.15-7.13 (d, 1H), 6.77-6.74 (td, 1H), 6.16-6.15 (d, 1H)

[0191] MW Melt point C1-132 508.62 294℃

[0192] [Example 7] Preparation of compound C1-6

[0193]

[0194] Compound 1-1 (7 g, 13 mmol), dibenzo[b,d]furan-1-ylboronic acid (3 g, 14.3 mmol), K2CO3(5.4 g, 39 mmol), and Pd(PPh3)4(0.75 g, 0.65 mmol) were dissolved in 30 mL of H2O, 60 mL of toluene, and 30 mL of EtOH in a flask and refluxed at 120°C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C1-6 (5.7 g, yield: 70%).

[0195] 1 H NMR (600 MHz, CDCl3, δ) 9.305 (s, 1H), 9.049-9.035 (d, J = 8.4 Hz, 1H), 8.379-8.367 (d, J = 7.2 Hz, 1H), 8.022-8.008 (d, J = 8.4 Hz, 1H) 7.816-7.705 (m, 6H), 7.699-7.392 (m, 16H) 7.195-7.127 (m, 2H)

[0196] MW Melt point C1-6 642.73 154℃

[0197] [Example 8] Preparation of compound C1-47

[0198]

[0199] Compound 1-1 (5.7 g, 10.6 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.5 g, 11.7 mmol), K2CO3(4.4 g, 31.8 mmol), and Pd(PPh3)4(0.61 g, 0.653 mmol) were dissolved in a flask in 30 mL of H2O, 60 mL of toluene, and 30 mL of EtOH, and refluxed at 120°C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C1-47 (1.2 g, yield: 18%).

[0200] 1 H NMR (600 MHz, CDC13, δ) 8.880 (s, 1H), 8.378-8.364 (d, J = 8.4 Hz, 1H), 8.297-8.284 (d, J = 7.8 Hz, 1H), 8.000-7.987 (d, J = 7.8 Hz, 1H) 7.777-7.702 (m, 5H), 7.615-7.332 (m, 15H), 7.189-7.127 (m, 4H)

[0201] MW Melt point C1-47 624.73 239℃

[0202] [Example 9] Preparation of compound C1-46

[0203]

[0204] Compound 1-1 (5.0 g, 9.3 mmol), dibenzo[b,d]furan-4-ylboronic acid (2.2 g, 10.2 mmol), Pd(PPh3)4(0.54 g, 0.47 mmol), and K2CO3(2.6 g, 18.6 mmol) were dissolved in a flask in 20 mL of toluene, 8 mL of EtOH, and 10 mL of H2O, and refluxed at 120°C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C1-46 (3.5 g, yield: 60%).

[0205] 1H NMR (600 MHz, DMSO-d6) δ: 9.69 (s, 1H), 9.26 (d, J = 8.3 Hz, 1H), 8.69 (dd, J = 7.7, 1.2 Hz, 1H), 8.14 (dd, J = 8.0, 1.1 Hz, 1H), 7.97 (d, J = 8.8 Hz, 1H), 7.92 (s, 4H), 7.88 (ddd, J = 8.2, 6.9, 1.3 Hz, 1H), 7.82 - 7.76 (m, 4H), 7.73 (t, J = 7.8 Hz, 2H), 7.70 - 7.48 (m, 8H), 7.48 - 7.44 (m, 2H), 7.42 (td, J = 7.3, 1.0 Hz, 1H), 7.26 - 7.20 (m, 1H)

[0206] MW Melt point C1-46 624.7 161℃

[0207] [Example 10] Preparation of compounds C1-41

[0208]

[0209] To 50 mL of o-xylene was added 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (3.6 g, 9.285 mmol), 1-(4-bromophenyl)dibenzo[b,d]furan (3 g, 9.285 mmol), CuI (0.08 g, 0.464 mmol), EDA (0.5 g, 9.285 mmol), and K3PO4 (4.9 g, 23.21 mmol) and stirred for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and then extracted with distilled water and MeOH. The resulting product was purified by column chromatography with MC / hexane to obtain compound C1-41 (2.7 g, yield: 47%).

[0210] 1 H NMR (DMSO-d6) δ: 9.69 (s, 1H), 9.26 (d, J = 8.3 Hz, 1H), 8.69 (dd, J = 7.7, 1.2 Hz, 1H), 8.14 (dd, J = 8.0, 1.1 Hz, 1H), 7.97 (d, J = 8.8 Hz, 1H), 7.92 (s, 4H), 7.88 (ddd, J = 8.2, 6.9, 1.3 Hz, 1H), 7.82 - 7.76 (m, 4H), 7.73 (t, J = 7.8 Hz, 2H), 7.70 - 7.48 (m, 8H), 7.48 - 7.44 (m, 2H), 7.42 (td, J = 7.3, 1.0 Hz, 1H), 7.26 - 7.20 (m, 1H)

[0211] MW Melt point C1-41 624.7 309.7℃

[0212] [Example 11] Preparation of Compound C1-3

[0213]

[0214] To 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (7.6 g, 18.88 mmol), 3'-chloro-1,1':2',1"-terphenyl (5 g, 18.88 mmol), Pd2(dba)3 (0.86 g, 0.940 mmol), NaOt-Bu (4.5 g, 47.22 mmol), and P(t-Bu)3 (0.38 g, 1.888 mmol) were added to 100 mL of toluene and stirred for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and then extracted with distilled water and MeOH. The resulting product was purified by column chromatography with MC / hexane to obtain Compound C1-3 (0.7 g, yield: 6.2%).

[0215] 1 H NMR (DMSO-d6) δ: 9.58 (s, 1H), 9.20 (d, J = 8.4 Hz, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.11 (d, J = 8.3 Hz, 1H), 7.94 (d, J = 8.9 Hz, 1H), 7.84 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.72 (d, J = 6.2 Hz, 4H), 7.64 - 7.47 (m, 8H), 7.44 (dt, J = 6.0, 1.9 Hz, 1H), 7.40 - 7.17 (m, 10H), 6.50 (d, J = 7.9 Hz, 1H)

[0216] MW Melt point C1-3 610.7 194.6℃

[0217] [Example 12] Preparation of Compound C1-11

[0218]

[0219] To a flask was added 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.1 g, 13 mmol), 9-(3-bromophenyl)-9H-carbazole (4.7 g, 14.6 mmol), Pd2(dba)3(0.604 g, 0.66 mmol), s-phos (0.546 g, 1.33 mmol), and NaOt-Bu (3.20 g, 33.3 mmol) in 50 mL of o-xylene, followed by refluxing at 190℃ for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and the extracted organic layer was dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C1-11 (4.4 g, yield: 53.0%).

[0220] 1 H NMR (600 MHz, DMSO-d6, δ) 9.66 (s, 1H), 9.24 (d, J = 8.4 Hz, 1H), 8.66 (d, J = 7.7 Hz, 1H), 8.26 (d, J = 7.8 Hz, 2H), 8.13 (d, J = 8.1 Hz, 1H), 8.01-7.94 (m, 2H), 7.91-7.84 (m, 3H), 7.79 (dd, J = 8.2, 1.8 Hz, 1H), 7.77-7.74 (m, 2H), 7.69 (t, J = 7.6 Hz, 2H), 7.62-7.55 (m, 3H), 7.53 (d, J = 8.1 Hz, 1H), 7.49-7.45 (m, 2H), 7.39 (dd, J = 14.4, 6.9 Hz, 5H) 7.31 (t, J = 7.5 Hz, 2H)

[0221] MW Melt point C1-11 623.76 240℃

[0222] [Example 13] Preparation of compound C1-18

[0223]

[0224] To a flask were added 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.0 g, 13 mmol), 4'-bromo-1,1':3',1"-terphenyl (6.06 g, 20 mmol), Cu powder (1.307 g, 0.65 mmol), and K2CO3 (3.4 g, 26 mmol) in 60 mL of o-dichlorobenzene (o-DCB), followed by refluxing at 230°C for 12 hours. After completion of the reaction, the organic layer was extracted with EA, and the extracted organic layer was dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C1-18 (1.3 g, yield: 16.3%).

[0225] 1 H NMR (600 MHz, DMSO-d6, δ) 9.51 (s, 1H), 9.16 (d, J = 8.3 Hz, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.98-7.85 (m, 6H), 7.83 (t, J = 7.6 Hz, 1H), 7.76 (s, 1H), 7.70 (d, J = 8.1 Hz, 1H), 7.61-7.51 (m, 5H), 7.51-7.42 (m, 3H), 7.38 (t, J = 7.8 Hz, 1H), 7.31 (t, J = 7.3 Hz, 1H), 7.25 (d, J = 8.0 Hz, 1H), 7.13-7.06 (m, 4H), 7.03 (d, J = 6.8 Hz, 1H), 6.79 (s, 1H)

[0226] MW Melt point C1-18 610.74 296℃

[0227] [Example 14] Preparation of compound C1-20

[0228]

[0229] 1) Synthesis of compound 1

[0230] To a flask were added 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (10 g, 26.14 mmol), 1-bromo-3-iodobenzene (14.8 g, 52.29 mmol), CuI (2.5 g, 13.07 mmol), EDA (1.57 g, 26.14 mmol), and K3PO4 (13.8 g, 65.36 mmol) in 130 mL of toluene and stirred for 1 day. After completion of the reaction, the mixture was cooled to room temperature, and then extracted with distilled water and MeOH. The resulting product was purified by column chromatography with MC / hexane to obtain compound 1 (9 g, yield: 64%).

[0231] 2) Synthesis of compound 2

[0232] Compound 1 (9 g, 16.74 mmol) was added to 85 mL of THF and n-BuLi (2.5 M) (8.7 mL, 21.77 mmol) was added thereto while stirring for 1 hour at -78°C. Then, B(Oi-pr)3 (5.7 mL, 25.12 mmol) was added to the mixture and stirred for 1 day. After the completion of the reaction, NH4Cl and distilled water were added to the mixture and stirred for 30 minutes. Thereafter, the organic layer was extracted with distilled water and EA, and then the extracted organic layer was concentrated to obtain compound 2 (6.8 g, yield: 80%).

[0233] 3) Synthesis of compound C1-20

[0234] Compound 2 (6.8 g, 13.53 mmol), 4-bromo-9,9-dimethyl-9H-fluorene (3.7 g, 13.53 mmol), Pd(PPh3)4 (0.8 g, 0.676 mmol), and K2CO3 (3.7 g, 27.07 mmol) were added to 60 mL of toluene, 15 mL of EtOH, and 15 mL of water and refluxed for 3 hours. After the completion of the reaction, the mixture was cooled to room temperature, and then extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound C1-20 (1.5 g, yield: 17%).

[0235] 1 H NMR (DMSO-d6) δ: 9.64 (s, 1H), 9.22 (d, J = 8.4 Hz, 1H), 8.64 (dt, J = 7.6, 0.9 Hz, 1H), 8.14-8.10 (m, 1H), 7.94 (d, J = 8.9 Hz, 1H), 7.90-7.77 (m, 3H), 7.68 (s, 3H), 7.65-7.53 (m, 7H), 7.53-7.33 (m, 6H), 7.27 (td, J = 7.4, 1.1 Hz, 1H), 7.17 (d, J = 7.6 Hz, 1H), 6.92 (d, J = 47.9 Hz, 2H), 1.49 (d, J = 17.3 Hz, 6H)

[0236] MW Melt point C1-20 650.8 166.3℃

[0237] [Example 15] Preparation of compound C1-2

[0238]

[0239] To a solution of compound C1-1 (0.1 g, 0.21 mmol) in 5 mL of DMF was added K2CO3 (0.1 g, 0.71 mmol) and 2-bromo-3-ethoxy-1,1-dimethyl-2-oxopropane (0.1 g, 0.51 mmol) and stirred for 1 day. After completion of the reaction, the mixture was cooled to room temperature and then extracted with distilled water and MeOH. The resulting product was purified by column chromatography with MC / Hexane to obtain compound C1-7 (0.1 g, yield: 80%).

[0240] 1 H NMR (DMSO-d6) δ: 9.63 (s, 1H), 9.23 (d, J = 8.3 Hz, 1H), 8.63 (dd, J = 7.7, 1.1 Hz, 1H), 8.12 (d, J = 8.2 Hz, 1H), 7.95 (d, J = 8.9 Hz, 1H), 7.85 (ddd, J = 8.2, 6.8, 1.4 Hz, 1H), 7.79-7.73 (m, 2H), 7.72-7.66 (m, 3H), 7.60-7.47 (m, 8H), 7.44 (ddd, J = 8.2, 7.1, 1.3 Hz, 1H), 7.38-7.33 (m, 3H), 7.32-7.24 (m, 2H), 7.22-7.14 (m, 5H)

[0241] MW Melt point C1-2 610.7 288℃

[0242] [Example 16] Preparation of compound C1-7

[0243]

[0244] 1) Synthesis of compound 1

[0245] To dibenzo[b,d]thiophen-1-ylboronic acid (20 g, 87.71 mmol), 1-bromo-3-iodobenzene (50 g, 175.4 mmol), Pd(PPh3)4 (5 g, 4.385 mmol) and Na2CO3 (18 g, 175.4 mmol) were added to 360 mL of toluene, 90 mL of water and 90 mL of EtOH and refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and then extracted with distilled water and EA followed by vacuum distillation. Thereafter, the resulting product was purified by column chromatography with hexane to obtain compound 1 (20 g, yield: 67%).

[0246] 2) Synthesis of compound C1-7

[0247] Compound 1 (4.4 g, 13.07 mmol), 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), Pd2(dba)3(0.6 g, 0.653 mmol), s-Phos (0.5 g, 1.307 mmol), and NaOt-Bu (3.7 g, 39.21 mmol) were added to 70 mL of o-xylene and refluxed for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, and then extracted with MeOH. Thereafter, the resulting product was purified by column chromatography with MC / hexane to obtain Compound C1-7 (5.1 g, yield: 60%).

[0248] 1 H NMR (DMSO-d6) δ: 9.63 (s, 1H), 9.22 (d, J = 8.4 Hz, 1H), 8.64 (dd, J = 7.5, 1.2 Hz, 1H), 8.14-8.09 (m, 2H), 8.07 (dt, J = 8.1, 0.9 Hz, 1H), 7.94 (d, J = 8.9 Hz, 1H), 7.91-7.82 (m, 3H), 7.72 (d, J = 2.0 Hz, 1H), 7.67 (d, J = 7.6 Hz, 2H), 7.63-7.48 (m, 8H), 7.48-7.41 (m, 2H), 7.40 (d, J = 6.1 Hz, 1H), 7.36 (td, J = 7.4, 1.0 Hz, 1H), 7.33 (d, J = 7.3 Hz, 1H), 7.09 (d, J = 49.0 Hz, 2H)

[0249] MW Melt point C1-7 640.7 226.7℃

[0250] [Example 17] Preparation of Compound C2-18

[0251]

[0252] 1) Synthesis of Compound 1

[0253] Dibenzo[b,d]furan-1-ylboronic acid (40.0 g, 189 mmol), 1-bromo-4-iodobenzene (80.06 g, 283 mmol), Pd(PPh3)4(10.90 g, 9 mmol), and Na2CO3(49.99 g, 472 mmol) were added dropwise to a flask of 550 mL of toluene, 200 mL of EtOH, and 200 mL of H2O, followed by refluxing at 150°C for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain Compound 1 (30.1 g, yield: 49.3%).

[0254] 2) Synthesis of compound 2

[0255] Compound 1 (9.0 g, 28 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (10.61 g, 42 mmol), PdCl2(PPh3)2 (0.977 g, 1 mmol) and KOAc (6.832 g, 70 mmol) were added dropwise into 150 mL of 1,4-dioxane, followed by refluxing at 140℃ for 1 hour. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound 2 (10.2 g, yield: 98.93%).

[0256] 3) Synthesis of compound C2-18

[0257] 2,3-dichloroquinoxaline (2.50 g, 13 mmol), compound 2 (10.23 g, 28 mmol), Pd(PPh3)4 (1.451 g, 1 mmol) and K2CO3 (8.680 g, 63 mmol) were added dropwise into a flask 10 mL of toluene, 3 mL of EtOH and 3 mL of H2O, followed by refluxing at 150℃ for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C2-18 (1.6 g, yield: 20.0%).

[0258] 1 H NMR (600 MHz, DMSO-d6, δ) 8.28 (dd, J = 6.3, 3.4 Hz, 2H), 7.98 (dd, J = 6.3, 3.4 Hz, 2H), 7.85-7.80 (m, 4H), 7.77 (dd, J = 8.3, 0.9 Hz, 2H), 7.73-7.68 (m, 4H), 7.66 (d, J = 8.1 Hz, 2H), 7.63 (dd, J = 8.2, 7.4 Hz, 2H), 7.42 (dt, J = 7.9, 0.9 Hz, 2H), 7.37 (dd, J = 7.4, 0.9 Hz, 2H), 7.30 (ddd, J = 8.4, 7.2, 1.3 Hz, 2H), 6.91 (td, J = 7.6, 1.0 Hz, 2H)

[0259] MW Melt point C2-18 614.70 231℃

[0260] [Example 18] Preparation of compound C2-3

[0261]

[0262] To 50 mL of toluene, 20 mL of EtOH and 20 mL of H2O were added 2-chloro-3- phenylquinoxaline (4.0 g, 17 mmol), compound 2 (8.38 g, 20 mmol), Pd(PPh3)4(0.960 g, 0.83 mmol) and K2CO3(6.89 g, 50 mmol), followed by refluxing at 140°C for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C2-3 (3.2 g, yield: 38.6%).

[0263] 1 H NMR (600 MHz, DMSO-d6, δ) 8.34-8.29 (m, 1H), 8.25 (d, J = 7.8 Hz, 1H), 8.04-7.95 (m, 2H), 7.87 (dd, J = 8.3, 0.9 Hz, 1H), 7.76-7.69 (m, 4H), 7.62 (d, J = 7.2 Hz, 1H), 7.54 (d, J = 7.5 Hz, 2H), 7.48-7.39 (m, 4H), 7.37 (s, 1H), 7.30 (dt, J = 26.1, 7.6 Hz, 3H), 7.19 (s, 1H), 7.03 (t, J = 7.5 Hz, 1H)

[0264] MW Melt point C2-3 498.59 245℃

[0265] [Example 19] Preparation of compound C2-29

[0266]

[0267] 1) Synthesis of compound 1

[0268] To a flask were added dibenzo[b,d]furan-1-ylboronic acid (80.0 g, 377 mmol), 1-bromo-4- iodobenzene (160.13 g, 566 mmol), Pd(PPh3)4(21.80 g, 19 mmol) and Na2CO3(99.99 g, 943 mmol) in 550 mL of toluene, 200 mL of EtOH and 200 mL of H2O, followed by refluxing at 150°C for 2.5 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound 1 (51.8 g, yield: 42.5%).

[0269] 2) Synthesis of compound 2

[0270] Compound 1 (30.0 g, 93 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (35.4 g, 139 mmol), PdCl2(PPh3)2 (3.26 g, 5 mmol) and KOAc (22.77 g, 232 mmol) were added dropwise to 150 mL of 1,4-dioxane, followed by refluxing at 140°C for 1 hour. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound 2 (23.3 g, yield: 67.8%).

[0271] 3) Synthesis of compound C2-29

[0272] 6-chloro-2,4-diphenylquinazoline (4.28 g, 14 mmol), compound 2 (6.00 g, 16 mmol), Pd(PPh3)4 (0.780 g, 0.675 mmol) and K2CO3 (4.67 g, 34 mmol) were added dropwise to a flask of 40 mL of toluene, 15 mL of EtOH and 15 mL of H2O, followed by refluxing at 150°C for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C2-29 (4.3 g, yield: 60.7%).

[0273] 1 H NMR (600 MHz, DMSO-d6, δ) 8.69-8.64 (m, 2H), 8.54 (dd, J = 8.7, 2.0 Hz, 1H), 8.42 (d, J = 2.0 Hz, 1H), 8.31 (d, J = 8.7 Hz, 1H), 8.03 (dd, J = 21.1, 7.3 Hz, 4H), 7.83-7.69 (m, 7H), 7.66-7.56 (m, 5H), 7.51 (t, J = 7.7 Hz, 1H), 7.37 (d, J = 7.4 Hz, 1H), 7.25 (t, J = 7.6 Hz, 1H)

[0274] MW Melt point C2-29 524.62 242℃

[0275] [Example 20] Preparation of compound C2-27

[0276]

[0277] To a flask of 70 mL of o-xylene were added 6-chloro-2,3-diphenylquinoxaline (4.28 g, 14 mmol), 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.00 g, 16 mmol), Pd2(dba)3 (0.618 g, 0.675 mmol), s-phos (0.554 g, 1 mmol), and NaOt-Bu (3.24 g, 34 mmol), followed by refluxing at 140°C for 2 hours. After completion of the reaction, the organic layer was extracted with EA, and dried with MgSO4. After purification by column chromatography, MeOH was added thereto, and the resulting solid was filtered under reduced pressure to obtain compound C2-27 (4.6 g, yield: 64.9%).

[0278] 1 H NMR (600 MHz, DMSO-d6, δ) 8.59 (d, J = 2.1 Hz, 1H), 8.41 (dd, J = 8.7, 2.1 Hz, 1H), 8.30 (d, J = 8.7 Hz, 1H), 8.21 (d, J = 8.2 Hz, 2H), 7.87-7.83 (m, 2H), 7.81-7.74 (m, 2H), 7.68-7.62 (m, 2H), 7.57-7.50 (m, 5H), 7.45-7.36 (m, 7H), 7.27 (t, J = 7.6 Hz, 1H)

[0279] MW Melt point C2-27 524.62 225℃

[0280] [Example 21] Preparation of compound C2-91

[0281]

[0282] To a flask were added compound 1 (4 g, 13.3 mmol), dibenzo[b,d]furan-1-ylboronic acid (5.9 g, 28 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (768 mg, 0.66 mmol), 13 mL of K2CO3 (2M), 52 mL of toluene, and 13 mL of ethanol, and dissolved. Then, the mixture was refluxed at 120°C for 4 hours. After completion of the reaction, the organic layer was extracted with EA, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C2-91 (2.5 g, yield: 33%).

[0283] MW Melt point C2-91 565.63 294℃

[0284] [Example 22] Preparation of compound C2-121

[0285]

[0286] 1) Synthesis of compound C2-121

[0287] Dibenzo[b,d]furan-1-yl boronic acid (3.0 g, 14.2 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.3 g, 15.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.71 mmol), Na2CO3(3.9 g, 28.4 mmol), 30 mL of toluene, 8 mL of EtOH, and 15 mL of H2O were added to a flask and dissolved. Then, the mixture was refluxed for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C2-121 (2.7 g, yield: 35%).

[0288] MW Melt point C2-121 551.6 233℃

[0289] [Example 23] Preparation of compound C2-107

[0290]

[0291] 1) Synthesis of compound C2-107

[0292] Dibenzo[b,d]furan-1-yl boronic acid (3.0 g, 14.2 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.3 g, 15.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.71 mmol), Na2CO3(3.9 g, 28.4 mmol), 30 mL of toluene, 8 mL of EtOH, and 15 mL of H2O were added to a flask and dissolved. Then, the mixture was refluxed for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C2-121 (2.7 g, yield: 35%).

[0293] MW Melt point C2-107 525.6 203℃

[0294] [Example 24] Preparation of compound C2-95

[0295]

[0296] 1) Synthesis of compound C2-95

[0297] Dissolve 2,4-dichloro-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine (1.6 g, 4.54 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.12 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.26 g, 0.23 mmol), Na2CO3(1.3 g, 9.0 mmol), 16 mL of toluene, 1 mL of EtOH, and 4 mL of H2O in a flask and dissolve. Then, reflux the mixture for 3 hours. After completion of the reaction, extract the organic layer with ethyl acetate, and remove residual water from the organic layer using magnesium sulfate. Thereafter, dry and purify the remaining product by column chromatography to obtain compound C2-95 (1.0 g, yield: 36%).

[0298] MW Melt point C2-95 615.7 304℃

[0299] [Example 25] Preparation of compound C2-113

[0300]

[0301] 1) Synthesis of compound C2-113

[0302] Dissolve 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.0 g, 10.8 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (4.4 g, 11.9 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.54 mmol), Na2CO3(3.0 g, 21.6), 30 mL of toluene, 7 mL of EtOH, and 10 mL of H2O in a flask and dissolve. Then, reflux the mixture for 7 hours. After completion of the reaction, extract the organic layer with ethyl acetate, and remove residual water from the organic layer using magnesium sulfate. Thereafter, dry and purify the remaining product by column chromatography to obtain compound C2-113 (4.0 g, yield: 65%).

[0303] MW Melt point C2-113 575.2 261℃

[0304] [Example 26] Preparation of compound C2-115

[0305]

[0306] 1) Synthesis of compound 1-1

[0307] Dibenzo[b,d]furan-1-ylboronic acid (20 g, 94.3 mmol), 1,4-dibromonaphthalene (53.9 g, 188.67 mmol), K2CO3 (32.6 g, 235.75 mmol), Pd(PPh3)4 (5.4 g, 4.7 mmol), 470 mL of toluene, 235 mL of EtOH, and 235 mL of H2O were added to a flask and dissolved. Then, the mixture was refluxed at 140℃ for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound 1-1 (20 g, yield: 56.8%).

[0308] 2) Synthesis of compound 1-2

[0309] Compound 1-1 (20 g, 53.6 mmol), bis(pinacolato)diboron (16.3 g, 64.3 mmol), PdCl2(PPh3)2 (3.76 g, 5.36 mmol), KOAc (10.5 g, 107.2 mmol), and 270 mL of 1,4-dioxane were added to a flask and dissolved. Then, the mixture was refluxed at 150℃ for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound 1-2 (23 g, yield: 100%).

[0310] 3) Synthesis of compound C2-115

[0311] Compound 1-2 (7 g, 16.6 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (7.35 g, 19.9 mmol), Cs2CO3 (13.5 g, 41.5 mmol), Pd(PPh3)4 (0.959 mg, 0.83 mmol), and 83 mL of toluene were added to a flask and dissolved. Then, the mixture was refluxed at 130℃ for 18 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C2-115 (2 g, yield: 19.2%).

[0312] MW Melt point C2-115 625.73 150℃

[0313] [Example 27] Preparation of compound C2-124

[0314]

[0315] 1) Synthesis of compound 2-1

[0316] 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (32.2 g, 87.7 mmol), (4-bromonaphthalen-1-yl)boronic acid (20 g, 79.7 mmol), Cs2CO3(65 g, 199.25 mmol), Pd(PPh3)4(4.6 g, 3.985 mmol), and 400 mL of toluene were added to a flask and dissolved. Then, the mixture was refluxed at 140°C for 4 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound 2-1 (20 g, yield: 46.6%).

[0317] 2) Synthesis of compound C2-124

[0318] Compound 2-1 (7 g, 13 mmol), compound 2-2 (4.6 g, 15.6 mmol), K2CO3(4.5 g, 32.5 mmol), and Pd(PPh3)4(0.75 g, 0.65 mmol) were added to a flask in 65 mL of toluene, 32.5 mL of EtOH, and 32.5 mL of H2O and dissolved. Then, the mixture was refluxed at 130°C for 3 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C2-124 (3.4 g, yield: 41%).

[0319] MW Melt point C2-124 625.73 250℃

[0320] [Example 28] Preparation of compound C2-114

[0321]

[0322] 1) Synthesis of compound 1

[0323] Dibenzo[b,d]furan-1-yl boronic acid (20 g, 94.33 mmol), 1,4-dibromonaphthalene (54 g, 188.6 mmol), Pd(PPh3)4(5.4 g, 4.716 mmol), and K2CO3(26 g, 188.6 mmol) were added to 380 mL of toluene, 95 mL of EtOH, and 95 mL of water and refluxed for 3 hours. After the completion of the reaction, the mixture was cooled to room temperature, and then the organic layer was extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound 1 (20 g, yield: 55%).

[0324] 2) Synthesis of compound 2

[0325] Compound 1 (20 g, 53.59 mmol) was added to PdCl2(PPh3)2 (3.7 g, 53.59 mmol), KOAc (10.5 g, 107.1 mmol), bis(pinacolato)diboron (17.7 g, 69.66 mmol), 270 mL of 1,4-dioxane and refluxed for 2 hours. After completion of the reaction, the mixture was filtered through a celite filter, then extracted with MC and then the organic layer was concentrated. The resulting product was purified by column chromatography with MC / hexane to obtain compound 2 (20 g, yield: 88%).

[0326] 3) Synthesis of compound C2-114

[0327] Compound 2 (6 g, 14.16 mmol), 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (5 g, 15.73 mmol), Pd(PPh3)4 (0.9 g, 0.786 mmol) and K2CO3 (4.3 g, 31.47 mmol) were added to 64 mL of toluene, 16 mL of EtOH and 16 mL of water and refluxed for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and then extracted with distilled water and EA, followed by vacuum distillation. The resulting product was purified by column chromatography with MC / hexane to obtain compound C2-114 (4 g, yield: 44%).

[0328] MW Melt point C2-114 575.6 131.3℃

[0329] [Example 29] Preparation of compound C2-90

[0330]

[0331] 1) Synthesis of compound 1

[0332] 2,4,6-trichloro-1,3,5-triazine (10 g, 54.22 mmol), dibenzo[b,d]furan-1-yl boronic acid (20.7 g, 97.60 mmol), PdCl2(PPh3)2 (0.76 g, 1.084 mmol) and Na2CO3 (5.7 g, 54.22 mmol) were added to 150 mL of toluene and 30 mL of water, then stirred for 2 days. After completion of the reaction, the mixture was cooled to room temperature and then extracted with distilled water and MeOH to obtain compound 1 (3.4 g, yield: 14%).

[0333] 2) Synthesis of compound C2-90

[0334] Compound 1 (3.4 g, 7.592 mmol), naphthalen-2-ylboronic acid (1.5 g, 9.111 mmol), Pd2(PPh3)4(0.4 g, 0.379 mmol), and K2CO3(2 g, 15.18 mmol) were added to 32 mL of toluene, 8 mL of EtOH, and 8 mL of water, and refluxed at 140°C for 1 hour. After completion of the reaction, the mixture was vacuum-evaporated, followed by extraction with MC, and then the organic layer was concentrated. The resulting product was purified by column chromatography with MC / hexane to obtain Compound C2-90 (0.88 g, yield: 21%).

[0335] [Example 30] Preparation of Compound C2-123

[0336]

[0337] 1) Synthesis of Compound 4-1

[0338] 2- chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (24.7 g, 77.7 mmol), (4- bromonaphthalen-1-yl)boronic acid (15.0 g, 59.8 l), K2CO3(20.7 g, 149.5 mmol), and Pd(PPh3)4(3.4 g, 3.0 mmol) were dissolved in a flask 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and refluxed at 130°C for 2 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain Compound 4-1 (15 g, yield: 51.3%).

[0339] 2) Synthesis of Compound C2-123

[0340] Compound 4-1 (7.5 g, 15.4 mmol), Compound 2-2 (5.0 g, 16.9 mmol), K2CO3(5.3 g, 38.4 mmol), and Pd(PPh3)4(888 mg, 0.768 mmol) were dissolved in 45 mL of toluene, 15 mL of EtOH, and 15 mL of H2O, and refluxed at 130°C for 6 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain Compound C2-123 (4.5 g, yield: 51%).

[0341] MW Melt point C2-123 575.66 213℃

[0342] [Example 31] Preparation of Compound C-5

[0343]

[0344] 1) Synthesis of compound 3-1

[0345] 3-bromodibenzofuran (5 g, 20 mmol), bis(pinacolato)diboron (7.6 g, 30 mmol), PdCl2(PPh3)2(1.4 g, 2 mmol), KOAc (3.9 g, 50 mmol), and 100 mL of 1,4-dioxane were added to a flask and dissolved. Then, the mixture was refluxed at 150°C for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound 3-1 (5 g, yield: 85%).

[0346] 2) Synthesis of compound C-5

[0347] Compound 2-1 (4.4 g, 12.3 mmol), compound 3-1 (5 g, 13.5 mmol), K2CO3(4.5 g, 32.5 mmol), Pd(PPh3)4(0.75 g, 0.65 mmol), 60 mL of toluene, 30 mL of EtOH, and 30 mL of H2O were added to a flask and dissolved. The mixture was refluxed at 130°C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and residual water was removed from the organic layer using magnesium sulfate. Thereafter, the remaining product was dried and purified by column chromatography to obtain compound C-5 (4 g, yield: 49%).

[0348] MW Melt point C-5 625.73 272℃

[0349] [Device Examples 1-1 to 3-2] Production of OLED in which a first host compound and a second compound according to the present disclosure are co-deposited as a host

[0350] An OLED according to the present disclosure was produced. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to ultrasonic washing with acetone and isopropanol in this order, and then stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in a chamber of the apparatus was controlled to 10 -7The first hole injection layer was formed on the ITO substrate by introducing compound HI-1 into one of the chambers of the vacuum vapor deposition apparatus and evaporating the compound by applying electric current to the chamber. After that, electric current was applied to the chamber to evaporate the above-introduced material, thereby forming the first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying electric current to the chamber, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying electric current to the chamber, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying electric current to the chamber, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the formation of the hole injection layer and the hole transport layers, a light-emitting layer was formed thereon as follows: the first host compound and the second host compound of Table 1 below were introduced into one of the chambers of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another chamber as a dopant. The two host materials were evaporated at a rate of 1:1 and the dopant was simultaneously evaporated at a different rate, so as to dope the dopant at a doping amount of 3 wt% with respect to the total amount of the host and the dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer. Next, compounds ET-1 and EI-1 were evaporated as an electron transport material at a weight ratio of 50:50, and deposition was performed to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound was purified by vacuum sublimation under a helium atmosphere at 10 -6 The compounds were purified by vacuum sublimation under a helium atmosphere at 10

[0351] [Comparative Examples 1 to 3] Production of OLEDs containing conventional compounds as a host

[0352] OLEDs were produced in the same manner as in the device examples, except that only one host compound was used, respectively.

[0353] The results of the driving voltage at a luminance of 1,000 nits, the voltage drop rate, and the luminous efficiency of the OLEDs of the device examples and the comparative examples produced as described above, as well as the roll-off value indicating the difference between the efficiency value at 5,000 nits and at 1,000 nits, and the time (T97) taken to reduce from 100% light intensity to 97% light intensity at a luminance of 1,000 nits, are shown in Table 1 below.

[0354] Table 1

[0355]

[0356] From the above Table 1, it is confirmed that the organic electroluminescent device including a specific combination of compounds according to the present disclosure as a host material can significantly reduce the driving voltage and improve the roll-off characteristics compared to the organic electroluminescent device including only one conventional host compound, thereby showing high efficiency even at high brightness. In addition, it is confirmed that the organic electroluminescent device according to the present disclosure can show the same or higher efficiency and / or improved lifetime characteristics compared to the conventional organic electroluminescent device.

[0357] [Device Examples 4 and 5] Production of OLED in which a first host compound and a second compound according to the present disclosure are co-deposited as a host

[0358] The OLED was produced in the same manner as in Device Example 3-2, except that Compound D-78 was used instead of Compound D-39 as a dopant and the compounds of Table 2 below were used as a host.

[0359] The results of the driving voltage, luminous efficiency, and CIE color coordinates of the organic electroluminescent device of Device Examples 4 and 5 produced as described above at a brightness of 1,000 nits are shown in Table 2 below.

[0360] Table 2

[0361]

[0362] From the above Table 2, it is confirmed that the organic electroluminescent device including a specific combination of compounds according to the present disclosure as a host material and a specific compound according to the present disclosure as a dopant material can show a low driving voltage, high luminous efficiency, and / or excellent color purity compared to the conventional organic electroluminescent device.

[0363] The compounds used in Device Examples 1-1 to 3-2, 4, and 5, and Comparative Examples 1 to 3 are shown in Table 3 below.

[0364] Table 3

[0365]

[0366]

[0367] [Device Examples 6 and 7] Production of OLED including compounds according to the present disclosure

[0368] OLEDs comprising the organic electroluminescent compounds according to the present disclosure were produced. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for OLEDs (Geomo Co., Ltd., Japan) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water in this order, and then stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 After that, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the formation of the hole injection and transport layers, a light-emitting layer was formed thereon as follows: the compound of Table 4 below was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The host and dopant materials were evaporated at different rates so as to dope the dopant at a doping amount of 3 wt% relative to the total amount of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer. Next, compounds ET-1 and EI-1 were introduced into another cell, evaporated at a rate of 1:1, and deposited, to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. Next, compound EI-1 was deposited as an electron injection layer having a thickness of 2 nm on the electron transport layer, and an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0369] [Comparative Examples 4 to 6] Production of OLEDs comprising conventional compounds as a host

[0370] OLEDs were produced in the same manner as in the device examples, except that the compounds of Table 4 below were used as a host, respectively.

[0371] Results of time taken for the OLEDs of Device Examples 6 and 7 and Comparative Examples 4 to 6 produced as described above to decrease from 100% luminance to 97% luminance and from 100% luminance to 80% luminance at a luminance of 5,000 nits (lifetime; T97 and T80) are shown in Table 4 below.

[0372] Table 4

[0373] MW Melt point MW Melt point C2-115 28 296 MW C2-114 7 243 Melt point C2-121 5.5 56 MW C2-113 5.5 142 Melt point MW Melt point MW Melt point Host T97 (hr) T80 (hr) Device Example 6 Device Example 7 Comparative Example 4 Comparative Example 5 Comparative Example 6 C2-120 5.9 108

[0374] From the above Table 4, by including the compound according to the present disclosure as a host material, an organic electroluminescent device having a significantly improved lifetime can be provided.

[0375] The compounds used in Device Examples 6 and 7 and Comparative Examples 4 to 6 are shown in Table 5 below.

[0376] Table 5

[0377]

Claims

1. An organic electroluminescent compound, represented by the following formula 2-1-1: in, X a Indicates O or S; L a This indicates unsubstituted naphthyl groups other than the 1,2-naphthyl group; and Ar a It represents unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted terphenyl or a combination thereof; Ar a This indicates an unsubstituted naphthyl group.

2. The organic electroluminescent compound according to claim 1, wherein, The compound represented by formula 2-1-1 is selected from the group consisting of:

3. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

4. The organic electroluminescent device according to claim 3, wherein, The organic electroluminescent compound is contained in the light-emitting layer.

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