Multiple host materials and organic electroluminescent devices containing the same

Abstract

The present disclosure relates to: a plurality of host materials including a first host compound and a second host compound, wherein the first host compound is represented by Formula 1 and the second host compound is represented by Formula 1, and the first host compound and the second host compound are different from each other; and an organic electroluminescent device including the plurality of host materials. By including the plurality of host materials including a specific combination of compounds, an organic electroluminescent device having excellent thermal stability, low driving voltage, high luminous efficiency, and / or improved lifetime characteristics can be produced.

Description

Technical Field

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

[0002] Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al. of Eastman Kodak in 1987 by using a TPD / ALq3 bilayer composed of a light-emitting layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. For displays for long-term use and high resolution, OLEDs having high luminous efficiency and / or long lifetime characteristics are required.

[0003] In order to enhance luminous efficiency, driving voltage, and / or lifetime, various materials or concepts for organic layers of organic electroluminescent devices have been proposed. However, they are not satisfactory in practical use.

[0004] Korean Patent Application Publication No. 2015-0121337 discloses a compound in which azulene, carbazole, etc. are fused. However, the reference does not specifically disclose using the compound as a variety of host compounds. Therefore, there is still a need to develop host materials for improving the performance of OLED devices. Summary of the Invention

[0005] Technical Problem

[0006] An object of the present disclosure is to provide an organic electroluminescent device having excellent thermal stability, low driving voltage, high luminous efficiency, and / or improved lifetime characteristics by including a variety of host materials including a specific combination of compounds.

[0007] Solution to the Problem

[0008] Advantageously, the light-emitting layer containing a phosphorescent dopant has excellent hole and electron current characteristics of a light-emitting material having low voltage, high efficiency, and long lifetime, and has excellent material thermal stability for improving lifetime. In addition, in order to effectively transfer energy from the host of the light-emitting layer to the dopant, a light-emitting material having a narrow band gap can minimize charge traps, thereby contributing to driving voltage and luminous efficiency. The azulene derivative included in the device of the present disclosure has a high internal conversion transition constant of S2→S1 of 7*10 -8 s, while it has 7*10 -12The low internal conversion transition constant from S1 to S0 of s, which improves the fluorescence quantum yield of S2→S0. Therefore, the azulene derivative is one of the representative materials that violate Kasha's rule. Phys.Chem.Chem.Phys. 2015, 17, 23573 [Physical Chemistry Chemical Physics 2015, 17, 23573], J. Phys. Chem. A, Vol. 103, No. 15, 1999, 2529 [Journal of Physical Chemistry A, Vol. 103, No. 15, 1999, 2529] reported that azulene can advantageously improve the phosphorescent emission characteristics because the S2 and S1 energy levels of azulene are 3.565 eV and 1.771 eV, respectively, and the T1→S0 transition shows a very low energy difference between T1 and S0 of 1.711 eV, and the intersystem crossing transition to S2→T n The intersystem crossing transition to n is improved according to the polarity of the substituted material and the solvent, resulting in an increase in the transition to the triplet state. Such azulene derivatives show a low S1→T1 energy gap and have relatively high HOMO characteristics compared to carbazole-type or benzocarbazole-type compounds, and thus may have a narrow bandgap. The inventors of the present invention found that by appropriately mixing the disclosed azulene derivatives as the first host and the second host in the light-emitting layer, the disclosed azulene derivatives can achieve low driving voltage, high luminous efficiency, and / or long lifetime characteristics. Specifically, the inventors of the present invention found that the above objects can be achieved by using the following various host materials, which include at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by Formula 1, and the first host compound and the second host compound are different from each other:

[0009]

[0010] wherein

[0011] M represents O or S;

[0012] X1 to X 12 each independently represents N or CR1;

[0013] La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;

[0014] Ar and R1 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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 tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(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 Ars may be connected to each other to form a ring, or adjacent R1s may be connected to each other to form a ring, where if there are multiple R1s, each R1 may be the same or different; and

[0015] a represents an integer of 1 or 2, where if a is 2, each Ar may be the same or different.

[0016] Advantages of the present invention

[0017] According to various host materials of the present disclosure, an organic electroluminescent device can be provided, which has excellent thermal stability, a low driving voltage, high luminous efficiency, and / or improved lifetime characteristics, and a display device or a lighting device can be produced using the organic electroluminescent device. Detailed embodiments

[0018] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present invention in any way.

[0019] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain 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 assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0020] The term "multiple organic electroluminescent materials" in the present disclosure means an organic electroluminescent material that is a combination of at least two compounds, and the material can be included in any layer constituting an organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds, which can be included 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. These at least two compounds can be included in the same layer or different layers, and can be co-evaporated or co-evaporated, or can be evaporated individually.

[0021] The term "multiple host materials" in the present disclosure means a host material that is a combination of at least two compounds, and the host material can be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple host materials of the present disclosure can be a combination of at least two host materials, and optionally can further include conventional materials included in the organic electroluminescent material. The multiple host materials of the present disclosure can be included in any light-emitting layer constituting the organic electroluminescent device, and at least two compounds included in the multiple host materials can be included together in one light-emitting layer or can be included separately in different light-emitting layers. If at least two host materials are included in one layer, then for example, the at least two compounds can be co-evaporated to form the layer, or can be evaporated simultaneously individually to form the layer.

[0022] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0023] In this text, the term “(C1-C30) (sub)alkyl” means a straight-chain or branched-chain (sub)alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C2-C30) alkenyl” means a straight-chain or branched-chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term “(C2-C30) alkynyl” means a straight-chain or branched-chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term “(C3-C30) (sub)cycloalkyl” means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7-membered) heterocycloalkyl” means a cycloalkyl having 3 to 7, preferably 5 to 7 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably consisting of the group of O, S, and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term “(C6-C30) (sub)aryl” means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The above (sub)aryl may be partially saturated and may contain a spiro structure. The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylene, pyrenyl, tetracenyl, chrysenyl, yl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. More specifically, the above aryl may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzoanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1- yl, 2- yl, 3- yl, 4- yl, 5- yl, 6- base, benzo[c]phenanthryl, benzo[g] base, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, 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, etc.

[0024] The term “(3- to 30-membered)(hetero)aryl” means an aryl having 3 to 30 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above (hetero)aryl can be monocyclic, or a fused ring fused with at least one benzene ring; it can be partially saturated; it can be a heteroaryl or heteroarylene formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds; and it can contain a spiro structure. The above heteroaryl can include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and fused-ring heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, the above heteroaryl can include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl,5 - quinolinyl, 6 - quinolinyl, 1 - carbazolyl, 2 - carbazolyl, 3 - carbazolyl, 4 - carbazolyl, 9 - carbazolyl, azacarbazolyl - 1 - yl, azacarbazolyl - 2 - yl, azacarbazolyl - 3 - yl, azacarbazolyl - 4 - yl, azacarbazolyl - 5 - yl, azacarbazolyl - 6 - yl, azacarbazolyl - 7 - yl, azacarbazolyl - 8 - yl, azacarbazolyl - 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 - methylpyrrol - 1 - yl, 2 - methylpyrrol - 3 - yl, 2 - methylpyrrol - 4 - yl, 2 - methylpyrrol - 5 - yl, 3 - methylpyrrol - 1 - yl, 3 - methylpyrrol - 2 - yl, 3 - methylpyrrol - 4 - yl, 3 - methylpyrrol - 5 - yl, 2 - tert - butylpyrrol - 4 - yl, 3 - (2 - phenylpropyl)pyrrol - 1 - yl, 2 - methyl - 1 - indolyl, 4 - methyl - 1 - indolyl, 2 - methyl - 3 - indolyl, 4 - methyl - 3 - indolyl, 2 - tert - butyl - 1 - indolyl, 4 - tert - butyl - 1 - indolyl, 2 - tert - butyl - 3 - indolyl, 4 - tert - butyl - 3 - indolyl, 1 - dibenzofuranyl, 2 - dibenzofuranyl, 3 - dibenzofuranyl, 4 - dibenzofuranyl, 1 - dibenzothienyl, 2 - dibenzothienyl, 3 - dibenzothienyl, 4 - dibenzothienyl, 1 - silafluorenyl group, 2 - silafluorenyl, 3 - silafluorenyl, 4 - silafluorenyl, 1 - germafluorenyl group, 2 - germafluorenyl, 3 - germafluorenyl and 4 - germafluorenyl. In addition, "halogen" includes F, Cl, Br and I.

[0025] In this text, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., a substituent).In the formulae of the present disclosure, the substituents of the substituted (C1-C30) (sub)alkyl, substituted (C6-C30) (sub)aryl, substituted (3- to 30-membered) (sub)heteroaryl, substituted (C3-C30) (sub)cycloalkyl, substituted (C1-C30) alkoxy, substituted tris(C1-C30) alkylsilyl, substituted bis(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted tris(C6-C30) arylsilyl, substituted mono- or di-(C1-C30) alkylamino, substituted mono- or di-(C6-C30) arylamino, and substituted (C1-C30) alkyl(C6-C30) arylamino are each independently at least one selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo(C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or (C6-C30) aryl-substituted (3- to 30-membered) heteroaryl, unsubstituted or (3- to 30-membered) heteroaryl-substituted (C6-C30) aryl, tris(C1-C30) alkylsilyl, tris(C6-C30) arylsilyl, bis(C1-C30) alkyl(C6-C30) arylsilyl, (C1-C30) alkyldi(C6-C30) arylsilyl, amino, mono- or di-(C1-C30) alkylamino, unsubstituted or (C1-C30) alkyl-substituted mono- or di-(C6-C30) arylamino, (C1-C30) alkyl(C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, bis(C6-C30) arylboronyl, bis(C1-C30) alkylboronyl, (C1-C30) alkyl(C6-C30) arylboronyl, (C6-C30) aryl(C1-C30) alkyl, and (C1-C30) alkyl(C6-C30) aryl; preferably at least one selected from the group consisting of: (C1-C20) alkyl, unsubstituted (C6-C25) aryl, and unsubstituted or (C6-C25) aryl-substituted (5- to 25-membered) heteroaryl; more preferably at least one selected from the group consisting of: (C1-C10) alkyl, unsubstituted (C6-C18) aryl, and (C6-C18) aryl-substituted (5- to 18-membered) heteroaryl; and for example at least one selected from the group consisting of: methyl, phenyl, diphenyltriazinyl, and phenylquinoxalinyl.

[0026] In the formulas of the present disclosure, if adjacent substituents are connected to each other to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic ring or aromatic ring, or a combination thereof, and the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur. For example, the fused ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0027] In the formulas of the present disclosure, a heteroaryl or heteroarylene may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be combined with at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0028] In Formula 1, M represents O or S.

[0029] In Formula 1, X1 to X 12 each independently represents N or CR1. According to one embodiment of the present disclosure, X1 to X 12 may all represent CR1. According to another embodiment of the present disclosure, any one of X1 to X 12 may represent N. According to another embodiment of the present disclosure, two of X1 to X 12 may represent N.

[0030] In Formula 1, La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; preferably a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5- to 25-membered) heteroarylene group; more preferably a single bond, an unsubstituted (C6-C18) arylene group, or an unsubstituted (5- to 18-membered) heteroarylene group. The heteroarylene group may include at least one of N, O, and S, and preferably at least one of N and S. According to one embodiment of the present disclosure, La may represent a single bond, a phenylene group, a naphthylene group, a biphenylene group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an isoquinolyl group, a quinazolinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoxazolinyl group, an indoloquinoxalinyl group, a benzothienopyrimidinyl group, or a benzquinazolinyl group.

[0031] In Formula 1, Ar and R1 each independently represent 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 tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(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 Ars may be connected to each other to form a ring, or adjacent R1s may be connected to each other to form a ring, where if there are multiple R1s, each R1 may be the same or different.

[0032] The above-mentioned Ar may preferably represent a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5- to 25-membered) heteroaryl group, or a substituted or unsubstituted di(C6-C25) arylamino group, and more preferably an unsubstituted (C6-C18) aryl group, an unsubstituted or (C1-C10) alkyl- and / or (C6-C12) aryl-substituted (5- to 25-membered) heteroaryl group, or an unsubstituted or (C1-C6) alkyl-substituted di(C6-C25) arylamino group. According to an embodiment of the present disclosure, Ar may represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted acenaphthopyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl group, a substituted or unsubstituted benzothienobenzolyl group, a substituted or unsubstituted benzofuranobenzolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothiazolinyl group, a substituted or unsubstituted phenanthrimidazolyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted fluorenylphenylamino group, a substituted or unsubstituted dibenzothienylphenylamino group, or a substituted or unsubstituted dibenzofuranylphenylamino group.According to another embodiment of the present disclosure, Ar may represent a phenyl group that is unsubstituted or substituted with at least one of deuterium and naphthyl, an unsubstituted naphthyl group, an unsubstituted biphenyl group, a fluorenyl group substituted with at least one methyl group, an unsubstituted fluoranthenyl group, a triazinyl group that is unsubstituted or substituted with at least one of phenyl and naphthyl, a pyridyl group that is unsubstituted or substituted with at least one phenyl group, a pyrimidinyl group that is unsubstituted or substituted with at least one phenyl group, a quinazolinyl group that is unsubstituted or substituted with at least one phenyl group, an isoquinolinyl group substituted with at least one phenyl group, a carbazolyl group that is unsubstituted or substituted with at least one phenyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted dibenzofuranyl group, a naphthyridinyl group substituted with at least one phenyl group, an unsubstituted diphenylamino group, an unsubstituted phenylbiphenylamino group, a dimethylfluorenylphenylamino group, a benzothienopyrimidinyl group substituted with at least one phenyl group, an unsubstituted benzothienoquinolinyl group, an unsubstituted benzofuroquinolinyl group, a benzquinazolinyl group substituted with at least one phenyl group, a benzothiazolinyl group substituted with at least one phenyl group, a benzquinoxalinyl group substituted with at least one phenyl group, an unsubstituted dibenzoquinoxalinyl group, a phenanthrimidazolyl group substituted with at least one phenyl group, an unsubstituted dibenzothiophenylphenylamino group, an unsubstituted dibenzofuranylphenylamino group, a nitrogen-containing 17-membered heteroaryl group substituted with at least one methyl group, a 25-membered heteroaryl group containing nitrogen and oxygen, or an acenapthyrimidinyl group substituted with at least one phenyl group.

[0033] The above R1 may preferably represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 25-membered) heteroaryl group; or adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (3- to 25-membered) alicyclic ring or aromatic ring, or a combination thereof, and one or more carbon atoms of the alicyclic ring or aromatic ring, or the combination thereof, may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur; more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5- to 18-membered) heteroaryl group; or adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (3- to 18-membered) aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur; and even more preferably an unsubstituted or (5- to 18-membered) heteroaryl group-substituted (C6-C12) aryl group, or an unsubstituted or (C6-C18) aryl group-substituted (5- to 13-membered) heteroaryl group; or adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (3- to 10-membered) aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. According to one embodiment of the present disclosure, R1 may represent an unsubstituted or diphenyltriazinyl group-substituted phenyl group, a diphenyltriazinyl group, a quinazolinyl group substituted with one or more phenyl groups, or an unsubstituted pyridyl group; or adjacent R1s may be connected to each other to form an unsubstituted benzene ring, an indene ring substituted with at least one of a methyl group and a phenyl group, an unsubstituted pyridine ring, an unsubstituted benzothiophene ring, an unsubstituted benzofuran ring, or an indole ring substituted with one or more phenyl groups or one or more phenylquinoxalinyl groups.

[0034] According to one embodiment of the present disclosure, two adjacent X1 to X in Formula 1 12 are CR1, and two adjacent R1s may be connected to each other to form any one of the rings in Formulas 2 to 6, and one or more of the rings may be formed in a compound represented by Formula 1. For example, the ring may be a dibenzothiophene ring, a dibenzofuran ring, a naphthalene ring, a phenanthrene ring, or a substituted or unsubstituted carbazole ring.

[0035]

[0036]

[0037] In Formulas 2 to 6, represents the connection site between C and R1 in CR1.

[0038] In Formula 4, X represents N or CH. According to one embodiment of the present disclosure, all Xs may represent CH. According to another embodiment of the present disclosure, any one of Xs may represent N.

[0039] In Formula 5, R2 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30) silyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) aryl silyl, substituted or unsubstituted tris(C6-C30) aryl silyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; preferably substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; more preferably unsubstituted (C6-C18) aryl, or unsubstituted or (C6-C18) aryl-substituted (5- to 18-membered) heteroaryl. According to one embodiment of the present disclosure, R2 may represent unsubstituted phenyl, or quinoxalinyl substituted with one or more phenyl groups.

[0040] In Formula 6, R 11 and R 12 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be joined to each other to form a ring. Preferably, R 11 and R 12 each independently represent hydrogen, substituted or unsubstituted (C1-C6) alkyl, or substituted or unsubstituted (C6-C12) aryl; or may be joined to each other to form a substituted or unsubstituted, monocyclic or polycyclic (5- to 10-membered) alicyclic ring or aromatic ring, or a combination thereof. More preferably, R 11 and R 12 each independently represent hydrogen, unsubstituted (C1-C6) alkyl, or unsubstituted (C6-C12) aryl; or may be joined to each other to form a spiro ring.

[0041] In Formula 1, a represents an integer of 1 or 2, where if a is 2, each Ar may be the same or different.

[0042] The compound represented by Formula 1 may be represented by any one of Formulas 7 to 10 below:

[0043]

[0044] where X1 to X12 X and M are as defined in Formula 1.

[0045] According to one embodiment of the present disclosure, at least one of X1 to X5, at least one of X6 to X9, and at least one of X 10 to X 12 represents N or CR1, where each R1 independently represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3-membered to 25-membered) heteroaryl group; or may be connected to an adjacent substituent to form a substituted or unsubstituted, monocyclic or polycyclic (3-membered to 25-membered) alicyclic ring or aromatic ring, or a combination thereof, and one or more carbon atoms of the alicyclic ring or aromatic ring, or the combination thereof, may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur.

[0046] According to one embodiment of the present disclosure, Ar in Formula 1 of the first host compound represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, and Ar in Formula 1 of the second host compound represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group.

[0047] According to another embodiment of the present disclosure, Ar in Formula 1 of the first host compound represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, and Ar in Formula 1 of the second host compound represents a substituted or unsubstituted (C6-C30) aryl 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.

[0048] The compounds represented by Formula 1 include, but are not limited to, the following compounds.

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] Two or more of Compounds C-1 to C-449 can be combined and used in an organic electroluminescent device.

[0067] The compound having Formula 1 according to the present disclosure can be produced by synthetic methods known to those skilled in the art and, for example, as shown in Reaction Schemes 1 to 7 below, but is not limited thereto:

[0068] [Reaction Scheme 1]

[0069]

[0070] [Reaction Scheme 2]

[0071]

[0072] [Reaction Scheme 3]

[0073]

[0074] [Reaction Scheme 4]

[0075]

[0076] [Reaction Scheme 5]

[0077]

[0078] [Reaction Scheme 6]

[0079]

[0080] [Reaction Scheme 7]

[0081]

[0082] In Reaction Schemes 1 to 7, X1 to X 12, R1, La, Ar, and a are as defined in Formula 1; R2, R 11 and R 12 are as defined in Formulas 5 and 6; Z has the same definition as R1; and OTf represents trifluoromethanesulfonate.

[0083] The organic electroluminescent device of the present disclosure may include a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

[0084] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include a light-emitting layer, and may 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 buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. The second electrode may be a semi-transmissive reflective electrode or a reflective electrode, and may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type depending on the type of material. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0085] The organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a plurality of organic electroluminescent materials, which include different compounds represented by Formula 1 as a first organic electroluminescent material and a second organic electroluminescent material. The organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer may include two or more different compounds represented by Formula 1.

[0086] The light-emitting layer includes a host and a dopant, wherein the host includes a plurality of host materials, and the compound represented by Formula 1 may be included as a first host compound and a second host compound of the plurality of host materials. The weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30, even more preferably from about 40:60 to about 60:40, and still more preferably about 50:50.

[0087] Herein, the light-emitting layer is a layer from which light is emitted, and may be a single layer or a multi-layer in which two or more layers are stacked. All of the first host material and the second host material may be included in one layer, or the first host material and the second host material may be included in respective different light-emitting layers. According to an embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer may be less than 20 wt%.

[0088] The organic electroluminescent device of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist 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 may further include an amine-based compound other than the various host materials of the present disclosure as at least one of a hole injection material, a hole transport material, a hole assist material, a light emission material, a light emission assist material, and an electron blocking material. In addition, according to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound other than the various host materials of the present disclosure as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0089] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be selected from complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.

[0090] The dopant included in the organic electroluminescent device of the present disclosure may include, but is not limited to, the compound represented by Formula 101.

[0091]

[0092] In Formula 101, L is selected from the following Structures 1 and 2:

[0093]

[0094] R 100 to R 103 each independently represents hydrogen, deuterium, a halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a cyano group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be connected to an adjacent substituent to form a ring together with pyridine, such as a substituted or unsubstituted quinoline, benzofuranopyridine, benzothiophenopyridine, benzothienoquinoline, or indenoquinoline ring;

[0095] R 104 to R 107Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or one or more halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to an adjacent substituent to form a ring together with benzene, such as a substituted or unsubstituted naphthyl group, fluorene, dibenzothiophene, dibenzofuran, indolopyridine, benzofuranopyridine, or benzothiophenopyridine ring;

[0096] R 201 to R 211 Each independently represents hydrogen, deuterium, a halogen, an unsubstituted or one or more halogen-substituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be linked to an adjacent substituent to form a ring; and

[0097] n represents an integer from 1 to 3.

[0098] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0099]

[0100]

[0101]

[0102]

[0103] In the organic electroluminescent device of the present disclosure, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be multilayered.

[0104] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control the injection of electrons and improve the interfacial characteristics between the light-emitting layer and the electron injection layer, and each of the multilayers may use two compounds simultaneously. The hole blocking layer or the electron transport layer may also be multilayered, and each of the multilayers may use multiple compounds.

[0105] In addition, the organic electroluminescent compound or multiple host materials according to the present disclosure may also be applied to an organic electroluminescent device including QD (quantum dot).

[0106] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, flow coating methods, etc. can be used.

[0107] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material for forming each layer can be dissolved or diffused and there are no problems in film-forming ability.

[0108] The first and second host compounds of the present disclosure can be formed into a film by the methods listed above, generally by co-evaporation or mixed evaporation methods. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to two chambers simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chamber to evaporate the materials. In addition, if the first and second host compounds are present in the same layer or different layers in the organic electroluminescent device, the two host compounds can be formed into a film individually. For example, the second host compound can be deposited after depositing the first host compound.

[0109] The present disclosure can provide a display device by using a plurality of host materials containing two or more different compounds represented by Formula 1. In addition, by using the organic electroluminescent device of the present disclosure, a display system or a lighting system can be manufactured. Specifically, by using the organic electroluminescent device of the present disclosure, a display system for, for example, a smartphone, a tablet computer, a notebook, a PC, a TV, or an automobile can be produced; or a lighting system, such as an outdoor or indoor lighting system.

[0110] Hereinafter, the preparation methods and characteristics of the compounds of the present disclosure, and the characteristics of the organic electroluminescent device containing a plurality of host materials of the present disclosure will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0111] Example 1: Preparation of Compound C-8

[0112]

[0113] Synthesis of Compound 1

[0114] In a flask, 70 g of 2-nitro-1-naphthol (370 mmol) and 4.5 g of 4-(dimethylamino)pyridine (DMAP) (37 mmol) were dissolved in 1800 mL of dichloromethane (MC). 62 mL of triethylamine (TEA) (444 mmol) was added dropwise at 0 °C and stirred for 20 minutes. 125.3 g of trifluoromethanesulfonic anhydride (444 mmol) was slowly added dropwise to the reactants at the same temperature and stirred for 1 hour. After the reaction was completed, the organic layer was extracted with MC, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 96.2 g of Compound 1 (yield: 81%).

[0115] Synthesis of Compound 2

[0116] In a flask, 96.2 g of Compound 1 (299 mmol), 72.1 g of 2-bromophenylboronic acid (359 mmol), 17.3 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 79.3 g of sodium carbonate (749 mmol) were dissolved in 1400 mL of toluene, 350 mL of ethanol, and 350 mL of water, and refluxed for 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 98 g of Compound 2 (yield: 99%).

[0117] Synthesis of Compound 3

[0118] In a flask, 98 g of Compound 2 (299 mmol), 78.5 g of 2-aminophenylboronic acid pinacol ester (358 mmol), 17.2 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 103 g of potassium carbonate (747 mmol) were dissolved in 1300 mL of toluene, 350 mL of ethanol, and 350 mL of water, and refluxed for 20 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 54 g of Compound 3 (yield: 53%).

[0119] Synthesis of Compound 4

[0120] In a flask, 25 g of Compound 3 (73 mmol) was dissolved in 250 mL of acetic acid and 25 mL of sulfuric acid. 6.5 g of sodium nitrite (95 mmol) was slowly added dropwise at 0 °C and stirred for 40 minutes. After the reaction was completed, the reaction product was added dropwise to water, and filtered to remove the moisture. The residue was dried and separated by column chromatography to obtain 2 g of Compound 4 (yield: 8.4%).

[0121] Synthesis of Compound 5

[0122] In a flask, 4.7 g of Compound 4 (15 mmol) was dissolved in 48 mL of triethyl phosphite and 48 mL of 1,2-dichlorobenzene, and the mixture was refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.7 g of Compound 5 (yield: 63%).

[0123] Synthesis of Compound C-8

[0124] In a flask, 2.1 g of Compound 5 (7 mmol), 3.1 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8 mmol), 0.81 g of palladium(II) acetate (0.36 mmol), 0.3 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.7 mmol), and 1.7 g of sodium tert-butoxide (18 mmol) were dissolved in 72 mL of 1,2-xylene, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.5 g of Compound C-8 (yield: 58%).

[0125] Compound MW UV PL Melting Point Tg C-8 598.71 308nm 495nm 285℃ 132.37℃

[0126] Example 2: Preparation of Compound C-301

[0127]

[0128] In a flask, 5.0 g of Compound 5 (17 mmol), 7.08 g of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (21 mmol), 105 mg of DMAP (0.858 mmol), and 7.1 g of potassium carbonate (51 mmol) were dissolved in 85 mL of dimethylformamide (DMF), and the mixture was refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.8 g of Compound C-301 (yield: 47%).

[0129] 11H NMR (600 MHz, CDCl3) δ 9.09 - 9.07 (d, J = 12 Hz, 1H), 8.93 - 8.91 (d, J = 12 Hz, 1H), 8.74 - 8.73 (d, J = 6 Hz, 2H), 8.71 - 8.69 (d, J = 12 Hz, 2H), 7.80 - 7.75 (m, 6H), 7.73 - 7.69 (m, 3H), 7.64 - 7.57 (m, 3H), 7.52 - 7.38 (m, 8H)

[0130] Compound MW Tg Melting Point C-301 598.71 124.4℃ 236℃

[0131] Example 3: Preparation of Compound C-10

[0132]

[0133] In a flask, 5.0 g of compound 5 (17 mmol), 11.28 g of 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (21 mmol), 625 mg of tris(dibenzylideneacetone)dipalladium(0) (0.686 mmol), 565 mg of S-Phos (1 mmol), and 4.9 g of sodium tert-butoxide (51 mmol) were dissolved in 100 mL of o-xylene and refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3.6 g of compound C-10 (yield: 32%).

[0134] 1 1H NMR (600 MHz, CDCl3) δ 9.25 - 9.24 (d, J = 6 Hz, 1H), 8.85 - 8.83 (sd, J = 12 Hz, 4H), 8.68 - 8.67 (d, J = 6 Hz, 1H), 7.94 - 7.92 (m, 1H), 7.82 - 7.79 (m, 3H), 7.74 - 7.61 (m, 10H), 7.49 - 7.42 (m, 5H), 7.31 - 7.29 (t, J = 6 Hz, 1H), 7.16 - 7.15 (d, J = 6 Hz, 1H), 6.96 - 6.94 (d, J = 12 Hz, 1H)

[0135] Compound MW Tg Melting Point C-10 648.7 159.5℃ 176℃

[0136] Example 4: Preparation of Compound C-7

[0137]

[0138] In a flask, 5 g of Compound 5 (17.1 mmol), 5.5 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (20.5 mmol), 0.1 g of DMAP (0.85 mmol), and 7.1 g of potassium carbonate (51.4 mmol) were dissolved in 85 mL of DMF and refluxed for 3 hours. After the reaction was completed, the reaction product was cooled, methanol and water were added thereto, and the mixture was filtered. The residue was dried and separated by column chromatography to obtain 4.4 g of Compound C-7 (yield: 49%).

[0139] 1 H NMR (600 MHz, CDCl3) 9.13 - 9.11 (d, J = 12 Hz, 1H), 8.97 - 8.95 (d, J = 12 Hz, 1H), 8.75 - 8.73 (d, J = 12 Hz, 4H), 7.83 - 7.75 (m, 5H), 7.64 - 7.59 (m, 6H), 7.54 - 7.51 (m, 3H), 7.48 - 7.45 (t, J = 12 Hz, 3H), 7.40 - 7.39 (m, 2H)

[0140] Compound MW Tg Melting Point C-7 522.6 105℃ 209℃

[0141] Example 5: Preparation of Compound C-302

[0142]

[0143] In a flask, 4.5 g of Compound 5 (15.4 mmol), 5.4 g of 2-chloro-4-(naphthalen-2-yl)quinazoline (18.5 mmol), 0.09 g of DMAP (0.7 mmol), and 6.4 g of potassium carbonate (46.3 mmol) were dissolved in 77 mL of DMF and refluxed for 1.5 hours. After the reaction was completed, the reaction product was filtered, dried, and separated by column chromatography to obtain 7.5 g of Compound C-302 (yield: 80%).

[0144] 1 H NMR (600 MHz, CDCl3) 9.03 - 9.02 (d, J = 6 Hz, 1H), 8.88 - 8.86 (d, J = 12 Hz, 1H), 8.39 (s, 1H), 8.22 - 8.21 (d, J = 6 Hz, 1H), 8.20 - 8.17 (d, J = 18 Hz, 1H), 8.15 - 8.05 (m, 2H), 8.00 - 7.98 (t, J = 6 Hz, 2H), 7.91 - 7.89 (m, 1H), 7.76 - 7.72 (m, 5H), 7.63 - 7.61 (m, 2H), 7.54 - 7.52 (m, 2H), 7.43 - 7.36 (m, 4H)

[0145] Compound MW Tg Melting Point C-302 545.65 120.6℃ 257℃

[0146] Example 6: Preparation of Compound C-9

[0147]

[0148] In a flask, 5.0 g of Compound 5 (17.16 mmol), 6.6 g of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17.16 mmol), 0.6 g of tris(dibenzylideneacetone)dipalladium(0) (0.686 mmol), 0.7 g of S-Phos (1.176 mmol) and 4.0 g of sodium tert-butoxide (42.9 mmol) were dissolved in 90 mL of o-xylene and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 6.2 g of Compound C-9 (yield: 62%).

[0149] 1 H NMR (600 MHz, CDCl3, δ) 9.06 - 9.05 (d, J = 6.0 Hz, 2H), 8.85 - 8.83 (d, J = 12 Hz, 4H), 7.90 - 7.89 (m, 1H), 7.82 - 7.78 (m, 4H), 7.74 - 7.72 (m, 2H), 7.66 - 7.58 (m, 8H), 7.45 - 7.43 (m, 3H), 7.42 - 7.39 (m, 2H)

[0150] Compound MW Tg Melting Point C-9 598.71 140.59℃ 260℃

[0151] Example 7: Preparation of Compound C-303

[0152]

[0153] In a flask, 4.3 g of Compound 5 (14.83 mmol), 4.7 g of 6-chloro-2,4-diphenylquinazoline (14.83 mmol), 0.5 g of Pd2(dba)3 (0.593 mmol), 0.6 g of S-Phos (1.483 mmol) and 3.6 g of sodium tert-butoxide (37.07 mmol) were dissolved in 80 mL of o-xylene and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.8 g of Compound C-303 (yield: 21%).

[0154] 11H NMR (600 MHz, CDCl3, δ) 8.74 - 8.73 (d, J = 6.0 Hz, 2H), 8.37 - 8.36 (d, J = 6.0 Hz, 1H), 8.28 - 8.27 (d, J = 6.0 Hz, 1H), 8.05 - 8.04 (d, J = 6.0 Hz, 1H), 7.89 - 7.88 (d, J = 6.0 Hz, 2H), 7.85 - 7.83 (m, 1H), 7.75 - 7.73 (d, J = 12 Hz, 2H), 7.69 - 7.67 (m, 2H), 7.57 - 7.50 (m, 7H), 7.42 - 7.37 (m, 4H), 7.34 - 7.31 (m, 1H), 7.22 - 7.21 (m, 1H)

[0155] Compound MW Tg Melting Point C-303 571.67 140.16℃ 189.3℃

[0156] Example 8: Preparation of Compound C-307

[0157]

[0158] In a flask, 5.4 g of compound 5 (18.53 mmol), 4.5 g of 2-chloro-3-naphthylquinoxaline (15.44 mmol), 2.1 g of potassium carbonate (15.44 mmol) and 0.9 g of DMAP (7.72 mmol) were dissolved in 80 mL of DMF and refluxed for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and the residual moisture was removed by using magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 2.3 g of compound C-307 (yield: 47%).

[0159] 1 1H NMR (600 MHz, CDCl3, δ) 8.36 - 8.34 (d, J = 6.0 Hz, 1H), 8.23 (s, 1H), 8.17 - 8.16 (d, J = 6.0 HZ, 1H), 7.90 - 7.86 (m, 3H), 7.73 - 7.71 (d, J = 12 Hz, 1H), 7.68 - 7.63 (m, 4H), 7.50 - 7.48 (m, 2H), 7.40 - 7.35 (m, 6H), 7.32 - 7.24 (m, 2H)

[0160] Compound MW Tg Melting Point C-307 545.65 133℃ 152℃

[0161] Example 9: Preparation of Compound C-13

[0162]

[0163] In a flask, 4.0 g of Compound 5 (13.73 mmol), 4.0 g of 2-chloro-3-phenylquinoxaline (16.47 mmol), 3.8 g of potassium carbonate (27.46 mmol), and 0.84 g of DMAP (6.87 mmol) were dissolved in 68 mL of DMF and refluxed for 18 hours. After the reaction was completed, the reaction product was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC, and the residual moisture was removed by using magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 2.3 g of Compound C-13 (yield: 33.8%).

[0164] 1 H NMR (600 MHz, CDCl3, δ) 8.32 - 8.30 (m, 1H), 8.16 - 8.15 (m, 1H), 7.89 - 7.83 (m, 3H), 7.73 (d, J = 7.38 Hz, 1H), 7.69 - 7.68 (m, 2H), 7.60 - 7.54 (m, 2H), 7.50 (d, J = 9.00 Hz, 1H), 7.42 - 7.37 (m, 3H), 7.29 - 7.27 (m, 3H), 7.21 - 7.15 (m, 4H)

[0165] Compound MW Tg Melting Point C-13 495.59 124.88℃ 154-164℃

[0166] Example 10: Preparation of Compound C-304

[0167]

[0168] Synthesis of Compound 10-1

[0169] 155 mL of toluene was added to 9 g of Compound 5 (30.89 mmol), 10.6 g of 1-bromo-3-iodobenzene (61.78 mmol), 3 g of CuI (15.44 mmol), 1.8 g of EDA (30.89 mmol), and 16.4 g of K3PO4 (77.22 mmol), and the mixture was stirred under reflux for one day. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3 and separated by column chromatography using MC / hexane to obtain 10 g of Compound 10-1 (yield: 75%).

[0170] Synthesis of Compound C-304

[0171] 50 mL of toluene, 13 mL of EtOH, and 13 mL of purified water were added to 5.7 g of Compound 10-1 (12.77 mmol), 0.73 g of Pd(PPh3)4 (0.638 mmol), and 3.5 g of K2CO3 (25.54 mmol), and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3 and separated by column chromatography using MC / hexane to obtain 2.9 g of Compound C-304 (yield: 43%).

[0172] 1 H NMR (600 MHz, DMSO-d6, δ) 8.232 - 8.206 (m, 3H), 8.111 - 8.098 (d, 1H), 7.962 - 7.946 (m, 1H), 7.929 - 7.903 (m, 3H), 7.896 - 7.882 (d, 1H), 7.806 - 7.802 (d, 2H), 7.783 - 7.759 (t, 2H), 7.738 - 7.723 (d, 1H), 7.635 - 7.620 (m, 1H), 7.581 - 7.548 (m, 2H), 7.513 - 7.440 (m, 6H)

[0173] Compound MW Tg Melting Point C-304 533.6 119℃ 208℃

[0174] Example 11: Preparation of Compound C-306

[0175]

[0176] In a flask, 5.0 g of Compound 10-1 (11.2 mmol), 3.0 g of N-phenyl-[1,1'-biphenyl]-4-amine (12.3 mmol), 0.51 g of Pd2(dba)3 (0.56 mmol), 0.46 g of S-Phos (1.12 mmol), and 2.7 g of sodium tert-butoxide (28 mmol) were added to 60 mL of toluene and refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.3 g of Compound C-306 (yield: 34%).

[0177] 11H NMR (600 MHz, DMSO-d6, δ) 7.896 - 7.880 (m, 1H), 7.863 - 7.850 (d, 1H), 7.805 - 7.790 (d, 1H), 7.758 - 7.745 (d, 1H), 7.733 - 7.720 (d, 1H), 7.669 - 7.650 (m, 2H), 7.640 - 7.627 (d, 1H), 7.604 - 7.566 (m, 2H), 7.522 - 7.507 (d, 1H), 7.447 - 7.384 (m, 7H), 7.373 - 7.347 (t, 1H), 7.335 - 7.311 (t, 1H), 7.269 - 7.237 (m, 6H), 7.175 - 7.156 (d, 1H), 7.147 - 7.122 (t, 1H), 7.069 - 7.062 (t, 1H)

[0178] Compound MW Tg Melting Point C-306 610.8 114℃ 132℃

[0179] Example 12: Preparation of Compound C-333

[0180]

[0181] In a flask, 2.6 g of Compound 12 (7.6 mmol), 2.95 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 mmol), 0.27 g of tris(dibenzylideneacetone)dipalladium(0) (0.3 mmol), 0.3 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.7 mmol), and 1.8 g of sodium tert-butoxide (19 mmol) were dissolved in 50 mL of 1,2-dimethylbenzene and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.9 g of Compound C-333 (yield: 38%).

[0182] 11H NMR (600 MHz, DMSO-d6, δ) 9.086 - 9.072 (d, 1H), 8.887 - 8.882 (t, 1H), 8.821 - 8.807 (d, 1H), 8.714 - 8.699 (d, 4H), 8.676 - 8.663 (d, 1H), 8.014 - 7.988 (t, 1H), 7.883 - 7.833 (m, 3H), 7.781 - 7.768 (d, 1H), 7.691 - 7.665 (t, 2H), 7.640 - 7.575 (m, 6H), 7.540 - 7.485 (m, 3H), 7.399 - 7.343 (m, 3H), 6.982 - 6.968 (d, 1H)

[0183] Compound MW Melting Point Tg C-333 648.77 195℃ 165℃

[0184] Example 13: Preparation of Compound C-372

[0185]

[0186] Synthesis of Compound 13-1

[0187] In a flask, 70 g of compound 5 (240 mmol) and 40.6 g of N-bromosuccinimide (255 mmol) were dissolved in 1200 mL of dimethylformamide and stirred at 0 °C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 68 g of compound 13-1 (yield: 76%).

[0188] Synthesis of Compound 13-2

[0189] In a flask, 47.3 g of compound 13-1 (127 mmol), 42 g of bis(pinacolato)diboron (166 mmol), 4.5 g of bis(triphenylphosphine)palladium(II) dichloride (6.4 mmol) and 25 g of potassium acetate (255 mmol) were dissolved in 635 mL of 1,4-dioxane and refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 31.5 g of compound 13-2 (yield: 59%).

[0190] Synthesis of Compound 13-3

[0191] In a flask, 4.5 g of compound 13-2 (10.7 mmol), 1.9 g of 1-bromobenzene (11.85 mmol), 0.63 g of tetrakis(triphenylphosphine)palladium(0) (0.54 mmol), and 3.7 g of potassium carbonate (26.95 mmol) were dissolved in 54 mL of toluene, 13 mL of ethanol, and 13 mL of water, and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.2 g of compound 13-3 (yield: 56%).

[0192] Synthesis of Compound C-372

[0193] In a flask, 2.2 g of compound 13-3 (5.9 mmol), 1.58 g of 2-chloro-3-phenylquinoxaline (6.57 mmol), 3.89 g of cesium carbonate (11.96 mmol), and 0.36 g of 4-dimethylaminopyridine (2.99 mmol) were dissolved in 30 mL of dimethyl sulfoxide, and stirred at 100 °C for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.9 g of compound C-372 (yield: 85%).

[0194] Compound MW Melting Point Tg C-372 571.68 210℃ 167℃

[0195] Example 14: Preparation of Compound C-334

[0196]

[0197] Synthesis of Compound 14-1

[0198] In a flask, 27 g of compound 13-2 (64.7 mmol), 14.4 g of 1-bromo-2-nitrobenzene (71.2 mmol), 3.7 g of tetrakis(triphenylphosphine)palladium(0) (3.2 mmol), and 22.4 g of potassium carbonate (162 mmol) were dissolved in 320 mL of toluene, 80 mL of ethanol, and 80 mL of water, and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 26.7 g of compound 14-1 (yield: 100%).

[0199] Synthesis of Compound 14-2

[0200] In a flask, 26.7 g of compound 14-1 (64.7 mmol), 18 mL of 1-iodobenzene (162 mmol), 18.5 g of copper(I) iodide (CuI) (97 mmol), 13 mL of ethylenediamine (194 mmol), and 27.4 g of potassium phosphate (129 mmol) were dissolved in 325 mL of toluene and refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual water was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 15.7 g of compound 14-2 (yield: 49%).

[0201] Synthesis of Compound 14-3

[0202] In a flask, 13.1 g of compound 14-2 (26.8 mmol) was added to 180 mL of triethyl phosphite and 180 mL of 1,2-dichlorobenzene and stirred at 200 °C for 2 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, the reaction product was cooled to room temperature, and hexane was added thereto to obtain a solid. The obtained solid was filtered through a filter to remove the solvent and separated by column chromatography to obtain 0.71 g of compound 14-3 (yield: 5.8%).

[0203] Synthesis of Compound C-334

[0204] In a flask, 0.71 g of compound 14-3 (1.56 mmol), 0.45 g of 2-chloro-3-phenylquinoxaline (1.87 mmol), 1.01 g of cesium carbonate (3.12 mmol), and 0.095 g of 4-dimethylaminopyridine (0.78 mmol) were dissolved in 30 mL of dimethyl sulfoxide and stirred at 100 °C for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature, and distilled water and methanol were added thereto. The obtained solid was filtered through a filter to remove the solvent and separated by column chromatography to obtain 0.50 g of compound C-334 (yield: 49%).

[0205] 11H NMR (600 MHz, CDCl3, δ) 8.333 - 8.248 (m, 3H), 8.192 - 8.099 (m, 1H), 7.911 - 7.820 (m, 3H), 7.767 - 7.754 (d, 1H), 7.613 - 7.526 (m, 5H), 7.488 - 7.410 (m, 4H), 7.395 - 7.347 (m, 3H), 7.329 - 7.296 (m, 2H), 7.230 - 7.205 (m, 2H), 7.179 - 7.153 (m, 1H), 7.130 - 7.075 (m, 1H), 7.056 - 7.030 (m, 1H), 6.874 - 6.688 (m, 1H)

[0206] Compound MW Melting Point C-334 660.78 290℃

[0207] Example 15: Preparation of Compound C-197

[0208]

[0209] Synthesis of Compound 15-1

[0210] In a flask, 40 g of compound 13-1 (108 mmol), 25.4 g of (2-methylthiophenyl)boronic acid (153.5 mmol), 6.26 g of tetrakis(triphenylphosphine)palladium(0) (5.40 mmol), and 26.3 g of potassium carbonate (272.0 mmol) were dissolved in 536 mL of tetrahydrofuran and 134 mL of distilled water, and refluxed at 100 °C for 18 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 40 g of compound 15-1 (yield: 89%).

[0211] Synthesis of Compound 15-2

[0212] In a flask, 40 g of compound 15-1 (96.8 mmol) was dissolved in 400 mL of tetrahydrofuran, 200 mL of acetic acid, and 12.6 mL of 34.5% hydrogen peroxide (145.2 mmol), and stirred at room temperature for 20 hours. After the reaction was completed, the mixture was concentrated, and the organic layer was extracted with dichloromethane and aqueous sodium bicarbonate, and then the residual moisture was removed by using magnesium sulfate. The residue was dried to obtain 42 g of compound 15-2 (yield: 100%).

[0213] Synthesis of Compound 15-3

[0214] Dissolve 42 g of Compound 15-2 (96.4 mmol) in 190 mL of trifluoromethanesulfonic acid and stir at room temperature for 3 days. After the reaction is complete, add 50 mL of pyridine and 1 M aqueous NaOH to the mixture at 0 °C to adjust the pH to 7 to 8, and reflux the mixture at 100 °C for 1 hour. Filter the resulting solid through a filter to remove the solvent and separate it by column chromatography to obtain 9.1 g of Compound 15-3 (yield: 24%).

[0215] Synthesis of Compound C-197

[0216] In a flask, dissolve 4 g of Compound 15-3 (10.1 mmol), 3 g of 2-chloro-3-phenylquinoxaline (12.1 mmol), 6.6 g of cesium carbonate (20.2 mmol), and 0.62 g of 4-dimethylaminopyridine (5.1 mmol) in 50 mL of dimethyl sulfoxide and stir at 100 °C for 4 hours. After the reaction is complete, cool the reaction product to room temperature and add distilled water and methanol to it. Filter the resulting solid through a filter to remove the solvent and separate it by column chromatography to obtain 4.8 g of Compound C-197 (yield: 79%).

[0217] 1 H NMR (600 MHz, CDCl3, δ) 8.337 - 8.310 (m, 1H), 8.247 - 8.202 (m, 1H), 8.196 - 8.151 (m, 1H), 7.957 - 7.945 (m, 1H), 7.928 (s, 1H), 7.912 - 7.837 (m, 3H), 7.794 - 7.728 (m, 3H), 7.685 - 7.672 (d, 1H), 7.531 - 7.498 (m, 1H), 7.469 - 7.414 (m, 2H), 7.348 - 7.300 (m, 2H), 7.262 - 7.173 (m, 4H), 7.102 - 7.087 (d, 1H), 7.036 - 6.955 (m, 1H)

[0218] Compound MW Melting Point Tg C-197 601.73 317℃ 194℃

[0219] Example 16: Preparation of Compound C-339

[0220]

[0221] Synthesis of Compound 16-1

[0222] 15.6 g of Compound 5 (53.5 mmol), 20 g of 2,3-dichlorobenzo[f]quinoxaline (80.3 mmol), 15 g of potassium carbonate (107.0 mmol) and 3.3 g of N,N-dimethyl-4-pyridinamine (26.7 mmol) were added to 270 mL of N,N-dimethylformamide and stirred at 150 °C for 4 hours. After completion of the reaction, the reaction product was cooled to room temperature and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 2.2 g of Compound 16-1 (yield: 8%).

[0223] Synthesis of Compound C-339

[0224] 2.2 g of Compound 16-1 (4.4 mmol), 800 mg of phenylboronic acid (6.6 mmol), 250 mg of tetrakis(triphenylphosphine)palladium(0) (0.2 mmol) and 1.2 g of sodium carbonate (10.9 mmol), 20 mL of toluene and 5 mL of ethanol were added to a reaction vessel and the mixture was stirred at 130 °C for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 1.8 g of Compound C-339 (yield: 76%).

[0225] 1 H NMR (600 MHz, CDCl3, δ) 9.403 - 9.390 (d, 1H), 8.119 - 8.105 (d, 1H), 8.012 - 7.997 (d, 1H), 7.994 - 7.979 (d, 1H), 7.867 - 7.851 (m, 1H), 7.847 - 7.822 (td, 1H), 7.815 - 7.788 (td, 1H), 7.734 - 7.722 (d, 1H), 7.686 - 7.656 (m, 4H), 7.600 - 7.585 (m, 1H), 7.509 - 7.494 (d, 1H), 7.404 - 7.389 (m, 2H), 7.385 - 7.359 (t, 1H), 7.295 - 7.264 (m, 2H), 7.250 - 7.219 (t, 1H), 7.208 - 7.182 (m, 3H)

[0226] Compound MW Melting Point Tg C-339 545.65 247℃ 148℃

[0227] Example 17: Preparation of Compound C-338

[0228]

[0229] Synthesis of Compound 17-1

[0230] 15.6 g of Compound 5 (53.5 mmol), 20 g of 2,3-dichlorobenzo[f]quinoxaline (80.3 mmol), 15 g of potassium carbonate (107.0 mmol) and 3.3 g of N,N-dimethyl-4-pyridinamine (26.7 mmol) were added to 270 mL of N,N-dimethylformamide and stirred at 150 °C for 4 h. After completion of the reaction, the reaction product was cooled to room temperature and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to afford 2.8 g of Compound 17-1 (yield: 10%).

[0231] Synthesis of Compound C-338

[0232] 2.7 g of Compound 17-1 (5.4 mmol), 1 g of phenylboronic acid (8.0 mmol), 310 mg of tetrakis(triphenylphosphine)palladium(0) (0.3 mmol), 1.4 g of sodium carbonate (13.4 mmol), 28 mL of toluene and 7 mL of ethanol were added to a reaction vessel and the mixture was stirred at 130 °C for 3 h. After completion of the reaction, the reaction product was cooled to room temperature and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to afford 2.5 g of Compound C-338 (yield: 86%).

[0233] 1 H NMR (600 MHz, CDCl3, δ) 9.119 - 9.106 (d, 1H), 8.160 - 8.125 (dd, 2H), 8.001 - 7.988 (d, 1H), 7.878 - 7.862 (m, 1H), 7.782 - 7.755 (td, 1H), 7.748 - 7.726 (m, 2H), 7.709 - 7.685 (t, 2H), 7.623 - 7.594 (m, 3H), 7.518 - 7.503 (d, 1H), 7.418 - 7.371 (m, 4H), 7.305 - 7.271 (m, 2H), 7.200 - 7.182 (m, 3H)

[0234] Compound MW Melting Point Tg C-338 545.65 299℃ 149℃

[0235] Example 18: Preparation of Compound C-379

[0236]

[0237] In a flask, 4.0 g of compound 5 (13.73 mmol), 5.2 g of 5-chloro-2,3-diphenylquinoxaline (16.47 mmol), 0.629 g of tris(dibenzylideneacetone)dipalladium(0) (0.686 mmol), 0.564 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 mmol), and 3.9 g of sodium tert-butoxide (41 mmol) were dissolved in 80 mL of 1,2-dimethylbenzene and refluxed for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 2.8 g of compound C-379 (yield: 35.67%).

[0238] 1 H NMR (600 MHz, CDCl3, δ) 8.323 - 8.307 (d, J = 7.2 Hz, 1H), 7.947 - 7.935 (m, 2H), 7.883 - 7.867 (m, 1H), 7.762 - 7.749 (d, J = 7.2 Hz, 2H), 7.686 - 7.673 (d, J = 7.8 Hz, 1H), 7.633 - 7.603 (m, 2H), 7.568 - 7.556 (d, J = 7.2 Hz, 2H), 7.404 - 7.337 (m, 6H), 7.307 - 7.281 (t, J = 7.8 Hz, 1H), 7.195 - 7.281 (m, 3H), 7.144 - 7.110 (t, J = 7.2 HZ, 1H), 7.087 - 7.074 (d, J = 7.8 HZ, 1H), 7.010 - 6.990 (m, 2H)

[0239] Compound MW Tg Melting Point C-379 571.67 135.60℃ 142℃

[0240] Example 19: Preparation of Compound C-389

[0241]

[0242] In a flask, 6.0 g of compound 5 (21 mmol), 7.8 g of 2-([1,1′-biphenyl]-3-yl)-3-chloroquinoxaline (25 mmol), 8.5 g of potassium carbonate (62 mmol), and 0.126 g of 4-dimethylaminopyridine (1 mmol) were dissolved in 100 mL of dimethylformamide and refluxed for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 8.8 g of compound C-389 (yield: 74%).

[0243] 1 1H NMR (600 MHz, CDCl3, δ) 8.338 - 8.325 (d, J = 7.8 Hz, 1H), 8.228 - 8.212 (d, J = 8.7 Hz, 1H), 7.907 - 7.877 (m, 3H), 7.783 - 7.758 (m, 2H), 7.686 - 7.683 (d, J = 7.8 Hz, 2H), 7.630 - 7.590 (m, 1H), 7.523 - 7.508 (d, J = 9 Hz, 2H), 7.447 - 7.390 (m, 3H), 7.341 - 7.332 (m, 2H), 7.284 - 7.236 (m, 3H), 7.205 (s, 1H), 7.088 - 7.066 (m, 1H), 7.016 - 7.002 (d, J = 7.8 Hz, 2H), 6.903 - 6.877 (m, 2H)

[0244] Compound MW Tg Melting Point C-389 571.67 120.06℃ 202℃

[0245] Example 20: Preparation of Compound C-395

[0246]

[0247] In a flask, 7.9 g of compound 5 (27 mmol), 7.9 g of 2-chloro-3-(phenyl-D5) quinoxaline (33 mmol), 11.24 g of potassium carbonate (81 mmol) and 0.166 g of 4-dimethylaminopyridine (1 mmol) were dissolved in 135 mL of dimethylformamide and refluxed for 4 hours. After the reaction was completed, the reaction product was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 3.2 g of compound C-395 (yield: 23.7%).

[0248] 1 1H NMR (600 MHz, CDCl3, δ) 8.318 - 8.305 (d, J = 7.8 Hz, 1H), 8.164 - 8.151 (d, J = 7.8 Hz, 1H), 7.892 - 7.834 (m, 3H), 7.740 - 7.728 (d, J = 7.2 Hz, 1H), 7.691 - 7.679 (d, J = 7.2 Hz, 2H), 7.603 - 7.587 (m, 1H), 7.508 - 7.493 (d, J = 9 Hz, 1H), 7.413 - 7.370 (m, 3H), 7.291 - 7.250 (m, 2H), 7.212 - 7.197 (d, J = 9 Hz, 1H)

[0249] Compound MW Tg Melting Point C-395 500.62 127℃ 158℃

[0250] Example 21: Preparation of Compound C-380

[0251]

[0252] In a flask, 10 g of compound 5 (28.82 mmol), 7.0 g of 2-chloro-3-(4-(naphthalen-2-yl)phenyl)quinoxaline (24.02 mmol), 1.5 g of 4-(dimethylamino)pyridine (12.01 mmol), and 3.3 g of potassium carbonate (24.02 mmol) were dissolved in 130 mL of dimethylformamide and refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 8.8 g of compound C-380 (yield: 59%).

[0253] 1 H NMR (600 MHz, CDCl3, δ) 8.33 - 8.32 (d, J = 6.0 Hz, 1H), 8.16 - 8.15 (d, J = 6.0 Hz, 1H), 7.88 - 7.84 (m, 4H), 7.80 - 7.77 (m, 3H), 7.74 - 7.73 (d, J = 6.0 Hz, 1H), 7.69 - 7.66 (m, 4H), 7.57 - 7.56 (m, 2H), 7.53 - 7.50 (m, 3H), 7.43 - 7.37 (m, 5H), 7.32 - 7.23 (m, 3H)

[0254] Compound MW Tg Melting Point C-380 621.74 145.6℃ 262.7℃

[0255] Example 22: Preparation of Compound C-394

[0256]

[0257] In a flask, 6 g of compound 5 (20.59 mmol), 9.1 g of 2-(3-chloroquinoxalin-2-yl)-9-phenyl-9H-carbazole (22.65 mmol), 1.2 g of 4-(dimethylamino)pyridine (10.29 mmol), and 2.8 g of potassium carbonate (20.59 mmol) were dissolved in 100 mL of dimethylformamide and refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 9.6 g of compound C-394 (yield: 70%).

[0258] 11H NMR (600 MHz, CDCl3, δ) 8.31 - 8.30 (d, J = 6.0 Hz, 1H), 8.13 - 8.11 (d, J = 12.0 Hz, 1H), 8.04 - 8.03 (d, J = 6.0 Hz, 1H), 7.94 - 7.93 (d, J = 6.0 Hz, 1H), 7.86 - 7.81 (m, 3H), 7.74 - 7.73 (d, J = 6.0 Hz, 1H), 7.65 - 7.63 (d, J = 12.0 Hz, 2H), 7.61 - 7.60 (m, 1H), 7.44 - 7.36 (m, 4H), 7.30 - 7.28 (m, 1H), 7.23 - 7.15 (m, 6H), 6.98 - 6.93 (m, 3H), 6.88 - 6.87 (m, 2H)

[0259] Compound MW Tg Melting Point C-394 660.78 154.09℃ 290.5℃

[0260] Example 23: Preparation of Compound C-346

[0261]

[0262] In a flask, 6.0 g of compound 5 (20.59 mmol), 9.1 g of 2-(2-chloroquinazolin-4-yl)-9-phenyl-9H-carbazole (22.65 mmol), 1.2 g of 4-(dimethylamino)pyridine (10.29 mmol), and 2.8 g of potassium carbonate (20.59 mmol) were dissolved in 100 mL of dimethylformamide and refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10 g of compound C-346 (yield: 77%).

[0263] 1 1H NMR (600 MHz, CDCl3, δ) 9.01 - 9.00 (d, J = 6.0 Hz, 1H), 8.85 - 8.84 (d, J = 6.0 Hz, 1H), 8.34 - 8.33 (d, J = 6.0 Hz, 1H), 8.23 - 8.22 (d, J = 6.0 Hz, 2H), 8.11 - 8.10 (d, J = 6.0 Hz, 1H), 8.05 (s, 1H), 7.86 - 7.82 (m, 2H), 7.79 - 7.77 (m, 1H), 7.75 - 7.71 (m, 3H), 7.67 - 7.64 (m.3H), 7.59 - 7.57 (m, 2H), 7.53 - 7.52 (m, 1H), 7.50 - 7.47 (m, 3H), 7.43 - 7.37 (m, 2H), 7.36 - 7.35 (m, 4H)

[0264] Compound MW Tg Melting Point C-346 660.78 158℃ 189.9℃

[0265] Example 24: Preparation of Compound C-388

[0266]

[0267] In a flask, 12 g of compound 5 (41.1 mmol), 14.8 g of 2-(4-bromophenyl)-4-phenylquinazoline (41.1 mmol), 1.5 g of tris(dibenzylideneacetone)dipalladium(0) (1.6 mmol), 1.7 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (4.1 mmol), and 9.8 g of sodium tert-butoxide (102.9 mmol) were dissolved in 274 mL of o-xylene and refluxed for 4 hours. After completion of the reaction, the reaction product was cooled and separated by column chromatography to obtain 1.1 g of compound C-388 (yield: 4.7%).

[0268] 1 H NMR (600 MHz, CDCl3, δ) 8.927 - 8.912 (d, J = 7.8 Hz, 2H), 8.199 - 8.160 (m, 2H), 7.925 - 7.910 (m, 3H), 7.865 - 7.855 (m, 1H), 7.759 - 7.672 (m, 6H), 7.620 - 7.587 (m, 5H), 7.540 - 7.525 (d, J = 9 Hz, 1H), 7.401 - 7.375 (m, 3H), 7.339 - 7.328 (m, 2H)

[0269] Compound MW Tg Melting Point C-388 571.6 133℃ 241℃

[0270] Example 25: Preparation of Compound C-381

[0271]

[0272] In a flask, 5.7 g of compound 5 (19.5 mmol), 7.7 g of 2-chloro-3-(dibenzo[b,d]furan-1-yl)quinoxaline (23.2 mmol), 0.1 g of 4-(dimethylamino)pyridine (0.9 mmol), and 8.1 g of potassium carbonate (58.5 mmol) were dissolved in 99 mL of dimethylformamide and refluxed for 3 hours 30 minutes. After completion of the reaction, the reaction product was cooled, and methanol and water were added thereto and it was filtered. The residue was dried and separated by column chromatography to obtain 6 g of compound C-381 (yield: 52%).

[0273] 11H NMR (600 MHz, CDCl3, δ) 8.324 - 8.271 (m, 2H), 7.962 - 7.942 (m, 2H), 7.867 - 7.855 (d, J = 7.2 Hz, 1H), 7.821 - 7.805 (m, 1H), 7.705 - 7.693 (d, J = 7.2 Hz, 1H), 7.655 - 7.595 (m, 3H), 7.567 - 7.537 (m, 2H), 7.394 - 7.272 (m, 8H), 7.124 - 7.155 (m, 1H), 6.984 - 6.958 (t, J = 7.2 Hz, 1H), 6.830 - 6.817 (d, J = 7.8 Hz, 1H)

[0274] Compound MW Tg Melting Point C-381 585.6 154.79℃ 233℃

[0275] Example 26: Preparation of Compound C-378

[0276]

[0277] In a flask, 3.8 g of compound 5 (13 mmol), 5.0 g of 2-([1,1′-biphenyl]-4-yl)-3-chloroquinoxaline (16 mmol), 800 mg of DMAP (7 mmol), and 3.6 g of potassium carbonate (26 mmol) were dissolved in 55 mL of dimethylformamide and refluxed for 18 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.4 g of compound C-378 (yield: 19%).

[0278] 1 1H NMR (600 MHz, CDCl3, δ) 8.33 - 8.32 (m, 1H), 8.17 - 8.16 (m, 1H), 7.90 - 7.84 (m, 3H), 7.74 (d, J = 7.50 Hz, 1H), 7.69 (t, J = 6.72 Hz, 2H), 7.63 (d, J = 8.4 Hz, 2H), 7.61 - 7.59 (m, 1H), 7.51 (d, J = 9.00 Hz, 1H), 7.45 - 7.37 (m, 7H), 7.35 - 7.27 (m, 5H), 7.23 (d, J = 8.79 Hz, 1H)

[0279] Compound MW Tg Melting Point C-378 571.68 137.6℃ 189℃

[0280] Example 27: Preparation of Compound C-386

[0281]

[0282] In a flask, 5.1 g of Compound 5 (17 mmol), 5.0 g of 6-chloro-2,3-diphenylquinoxaline (16 mmol), 578 mg of tris(dibenzylideneacetone)dipalladium(0) (0.631 mmol), 648 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2 mmol), and 3.8 g of sodium tert-butoxide (39 mmol) were dissolved in 100 mL of toluene and refluxed for 16 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 7.6 g of Compound C-386 (yield: 84%).

[0283] 1 H NMR (600 MHz, CDCl3, δ) 8.01 (s, 1H), 8.40 (d, J = 5.4 Hz, 1H), 7.99 (dd, J = 5.4 Hz; 2.22 Hz, 1H), 7.89 - 7.87 (m, 1H), 7.79 - 7.77 (m, 2H), 7.74 - 7.70 (m, 2H), 7.63 - 7.60 (m, 2H), 7.59 - 7.56 (m, 4H), 7.44 - 7.34 (m, 11H)

[0284] Compound MW Tg Melting Point C-386 571.68 138.80℃ 295℃

[0285] Example 28: Preparation of Compound C-387

[0286]

[0287] 6.6 g of Compound 10-1 (14.78 mmol), 3.4 g of dibenzo[b,d]furan-1-ylboronic acid (16.24 mmol), 0.85 g of tetrakis(triphenylphosphine)palladium(0) (0.739 mmol), and 4 g of potassium carbonate (29.57 mmol) were added to 60 mL of toluene, 15 mL of ethanol, and 15 mL of pure water, and the mixture was stirred under reflux for one day. After the reaction was completed, the reaction product was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3 and separated by column chromatography using MC / hexane to obtain 3.5 g of Compound C-387 (yield: 45%).

[0288] 11H NMR (600 MHz, DMSO, δ) 7.953 - 7.927 (m, 2H), 7.896 - 7.872 (t, 2H), 7.848 - 7.810 (m, 3H), 7.793 - 7.746 (m, 4H), 7.656 - 7.601 (m, 4H), 7.539 - 7.511 (t, 1H), 7.485 - 7.443 (m, 4H), 7.419 - 7.393 (t, 1H), 7.369 - 7.356 (d, 1H), 7.294 - 7.269 (t, 1H)

[0289] Compound MW Melting Point Tg C-387 533.6 224℃ 117℃

[0290] Example 29: Preparation of Compound C-393

[0291]

[0292] In a flask, 4.4 g of compound 5 (15.16 mmol), 5.0 g of 9-chloro-6-phenyl-6H-indolo[2,3,b]quinoxaline (15.16 mmol), 0.5 g of tris(dibenzylideneacetone)dipalladium(0) (0.606 mmol), 0.6 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.516 mmol) and 12 g of sodium tert-butoxide (37.90 mmol) were dissolved in 100 mL of 1,2-dimethylbenzene and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.9 g of compound C-393 (yield: 21%).

[0293] 1 1H NMR (600 MHz, CDCl3, δ) 8.74 (s, 1H), 8.33 - 8.32 (d, J = 6.0 Hz, 1H), 8.15 - 8.14 (d, J = 6.0 Hz, 1H), 7.91 - 7.90 (m, 1H), 7.84 - 8.73 (m, 2H), 7.80 - 7.78 (m, 5H), 7.77 - 7.69 (m, 5H), 7.64 - 7.63 (m.1H), 7.60 - 7.59 (m, 1H), 7.50 - 7.49 (d, J = 6.0 Hz, 1H), 7.43 - 7.41 (m, 3H), 7.36 - 7.34 (t, J = 6.0 Hz, 1H), 7.28 - 7.27 (m, 1H)

[0294] Compound MW Tg Melting Point C-393 584.67 129.07℃ 294℃

[0295] Example 30: Preparation of Compound C-447

[0296]

[0297] Synthesis of Compound 30-1

[0298] In a flask, 8.0 g of Compound 13-1 (21.6 mmol), 12.1 g of 4-iodobiphenyl (43.2 mmol), 1.0 g of tris(dibenzylideneacetone)dipalladium(0) (1.08 mmol), 0.87 mL of tri-tert-butylphosphine (2.16 mmol, 50% toluene solution), and 5.2 g of sodium tert-butoxide (54.0 mmol) were dissolved in 216 mL of toluene and refluxed for 18 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 7.5 g of Compound 30-1 (yield: 66%).

[0299] Synthesis of Compound 30-2

[0300] 7.5 g of Compound 30-1 (14.4 mmol), 4.5 g of methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (17.3 mmol), 323 mg of palladium acetate (Pd(OAc)2) (1.44 mmol), 1.2 g of ligand (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) (2.88 mmol), 14 g of cesium carbonate (43.2 mmol), 80 mL of xylene, 40 mL of ethanol, and 40 mL of distilled water were added to a flask and stirred under reflux for 18 hours. The mixture was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 2.2 g of Compound 30-2 (yield: 27%).

[0301] Synthesis of Compound 30-3

[0302] 2.2 g of Compound 30-2 (3.8 mmol), 2 mL of Eaton's reagent, and 13 mL of benzene chloride were added to a flask and stirred under reflux for 18 hours. The mixture was cooled to room temperature and an aqueous sodium bicarbonate solution was added thereto. The organic layer was extracted with ethyl acetate (EA) and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain 1.5 g of Compound 30-3 (yield: 71%).

[0303] Synthesis of Compound C-447

[0304] 244 mg of iodine (0.96 mmol), 0.48 mL of hypophosphorous acid (4.4 mmol, 50% aqueous solution), and 14 mL of acetic acid were added to a flask and stirred at 80 °C for 30 minutes. 1.5 g of Compound 30-3 (2.75 mmol) was slowly added dropwise thereto and stirred under reflux for 4 hours. The reaction solution was cooled to room temperature, and the precipitated solid was filtered and washed with a large amount of water and ethanol. The obtained solid was filtered through the filter to remove the solvent. The residue was separated by column chromatography to obtain 270 mg of Compound C-447 (yield: 18%).

[0305] 1 H NMR (600 MHz, CDCl3, δ) 8.051 - 8.036 (dd, 1H), 7.967 - 7.953 (m, 1H), 7.920 - 7.909 (d, 1H), 7.857 - 7.843 (d, 2H), 7.797 - 7.784 (d, 1H), 7.720 - 7.698 (m, 2H), 7.669 - 7.643 (m, 3H), 7.562 - 7.500 (m, 5H), 7.463 - 7.416 (m, 5H), 7.217 - 7.190 (m, 2H), 4.153 - 4.188 (d, 1H), 3.949 - 3.913 (d, 1H)

[0306] Comparative Example 1: Production of an OLED device containing a conventional compound as the host

[0307] An OLED device was produced by using a conventional compound not according to the present disclosure as a host. The indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on the glass substrate for the OLED device was subjected to ultrasonic washing successively with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. Then the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition apparatus. Compound HI-1 was introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -7Support. Thereafter, an electric current is applied to the chamber to evaporate the above-introduced material, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Then, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into the chamber of the vacuum vapor deposition apparatus and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-3 is introduced into another chamber of the vacuum vapor deposition apparatus and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming these hole injection layers and hole transport layers, a light-emitting layer is formed thereon as follows: CBP is introduced as a host into one chamber of the vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into another chamber. The two materials are evaporated at different rates and the dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Compound ETL-1: EIL-1 is deposited at a weight ratio of 50:50 to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer by another vacuum vapor deposition apparatus. All materials used for producing the OLED are purified by vacuum sublimation at 10 -6 torr.

[0308] Device Examples 1 to 5: Production of an OLED device containing various host materials according to the present disclosure

[0309] An OLED device is produced in the same manner as in Comparative Example 1, except that a light-emitting layer is formed as follows: the first host compound and the second compound shown in Table 1 are introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into another chamber. The two host materials are evaporated at a rate of 1:1, and the dopant material is evaporated simultaneously at different rates, and the dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer.

[0310] Table 1 below provides the driving voltage and luminous efficiency of the OLED devices produced in Comparative Example 1 and Device Examples 1 to 5 at a brightness of 5,000 nits, and the time (lifetime; T98) taken for the brightness to decrease from 100% to 98% at a brightness of 5,000 nits.

[0311] [Table 1]

[0312]

[0313] Device Example 6: Production of an OLED device containing various host materials according to the present disclosure

[0314] An OLED device was produced in the same manner as in Comparative Example 1, except that compound HT-2 was used instead of compound HT-3 as the second hole transporting material, and the light-emitting layer was formed as follows: The first host compound (C-339) and the second compound (C-338) were introduced into two chambers of a vacuum vapor deposition apparatus as hosts, 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 material was simultaneously evaporated at a different rate, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transporting layer.

[0315] The driving voltage and luminous efficiency of the OLED device produced in Device Example 6 based on a luminance of 1,000 nits were 2.8 V and 29.0 cd / A, respectively, and the time (lifetime; T98) taken for the luminance to decrease from 100% to 98% based on a luminance of 5,000 nits was 169.8 h.

[0316] As can be seen from Table 1 and Device Example 6 above, compared with an OLED device containing a conventional organic electroluminescent compound, an OLED device containing a plurality of host materials of the present disclosure has a low driving voltage, a high luminous efficiency, and / or improved lifetime characteristics.

[0317] The compounds used in the device examples and comparative examples are shown in Table 2 below.

[0318] [Table 2]

[0319]

Claims

1. A plurality of host materials, the plurality of host materials including a first host compound and a second host compound, wherein the first host compound and the second host compound are represented by Formula 1, and the first host compound and the second host compound are different from each other: Wherein Formula 1 is represented by any one of Formulas 7 to 10: M represents O or S; X1 to X 12 each independently represents N or CR1; La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; Ar and R1 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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 tris(C1-C30) alkylsilyl group, a substituted or unsubstituted bis(C1-C30) alkyl(C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl group, a substituted or unsubstituted tris(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 Ars may be connected to each other to form a ring, or adjacent R1s may be connected to each other to form a ring, where if there are multiple R1s, each R1 may be the same or different; and a represents an integer of 1 or 2, where if a is 2, each Ar may be the same or different.

2. The multiple main materials according to claim 1, wherein, In the substituted (C1-C30)(sub)alkyl, substituted (C6-C30)(sub)aryl, substituted (3- to 30-membered)(sub)heteroaryl, substituted (C3-C30)(sub)cycloalkyl, substituted (C1-C30)alkoxy, substituted tris(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tris(C6-C30)arylsilyl, substituted mono- or di-(C1-C30)alkylamino, substituted mono- or di-(C6-C30)arylamino, and substituted (C1-C30)alkyl(C6-C30)arylamino in La, Ar, and R1, the substituents are each independently at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, unsubstituted or (C6-C30)aryl-substituted (3- to 30-membered)heteroaryl, unsubstituted or (3- to 30-membered)heteroaryl-substituted (C6-C30)aryl, tris(C1-C30)alkylsilyl, tris(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, unsubstituted or (C1-C30)alkyl-substituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

3. The plurality of host materials according to claim 1, wherein, Ar represents a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzothienobenzolinyl, substituted or unsubstituted benzofuranobenzolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzothiazolinyl, substituted or unsubstituted phenanthrimidazolyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted fluorenylphenylamino, substituted or unsubstituted dibenzothienylphenylamino, or substituted or unsubstituted dibenzofuranylphenylamino.

4. The multiple main materials according to claim 1, wherein, Two adjacent X1 to X 12 is CR1, two adjacent R1s are connected to each other to form any one of rings of Formulae 2 to 6, and one or more of said rings are formed in a compound represented by Formula 1: Wherein R2 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30) alkylsilyl, substituted or unsubstituted bis(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkylbis(C6-C30) arylsilyl, substituted or unsubstituted tris(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; X represents N or CH; R 11 and R 12 each independently represents hydrogen, deuterium, a halogen, a cyano group, 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, or a substituted or unsubstituted (C3-C30) cycloalkyl group; or they may be connected to each other to form a ring; and Denote the connection site between C and R1 in CR1.

5. The multiple main materials according to claim 1, wherein, The compound represented by Formula 1 is selected from the following compounds:

6. The multiple main materials according to claim 1, wherein, Ar in Formula 1 of the first host compound represents a substituted or unsubstituted (3- to 30-membered) heteroaryl, and Ar in Formula 1 of the second host compound represents a substituted or unsubstituted (3- to 30-membered) heteroaryl.

7. The plurality of matrix materials according to claim 1, wherein, Ar in Formula 1 of the first host compound represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group, and Ar in Formula 1 of the second host compound represents a substituted or unsubstituted (C6-C30) aryl 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.

8. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers contains a plurality of host materials according to claim 1.

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