Various host materials and organic electroluminescent devices comprising the same

Abstract

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

Description

Technical Field

[0001] This disclosure relates to various host materials and an organic electroluminescent device incorporating them. Background Technology

[0002] In 1987, Tang et al. of Eastman Kodak first developed a small-molecule green organic light-emitting diode (OLED) consisting of a TPD / Alq3 bilayer composed of an emissive layer and a charge transport layer. Since then, research on OLEDs has rapidly progressed, and they have been commercialized. Currently, phosphorescent materials, which offer excellent luminous efficiency for clear panels, are mainly used in organic light-emitting diodes. Therefore, for long-term use and high resolution of displays, OLEDs with high luminous efficiency and / or long lifespan are required.

[0003] Korean patent applications 2015-0086721, 2014-0096203, and 2015-0116776 disclose various host materials using carbazole derivative compounds. However, the aforementioned references do not specifically disclose the various host materials described in this disclosure. Furthermore, there is a need to develop luminescent materials that possess improved performance compared to the host materials disclosed in the aforementioned references, such as improved luminescent efficiency and / or lifetime characteristics. Summary of the Invention

[0004] Technical issues

[0005] The purpose of this disclosure is to provide an organic electroluminescent device that has high luminous efficiency and / or long lifetime characteristics by including a specific combination of compounds as the host material.

[0006] Solution to the problem

[0007] The inventors of this invention have discovered that the above objectives can be achieved by a variety of host materials, including a first host material and a second host material, wherein the first host material comprises a compound represented by Formula 1, and the second host material comprises a compound represented by Formula 2.

[0008]

[0009] in,

[0010] Ring A, ring B, and ring C each independently represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring;

[0011] Y represents O, S, or NRa;

[0012] Ra represents -L2-Ar2;

[0013] Ar1 and Ar2 each independently represent substituted or unsubstituted (C6-C30) aryl; substituted or unsubstituted (3-membered to 30-membered) heteroaryl containing at least one of nitrogen, oxygen and sulfur; or substituted or unsubstituted di(C6-C30) arylamino;

[0014] L1 and L2 independently represent single-bonded, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; and

[0015] n represents an integer of 0 or 1, provided that if n is 0, then both ring A and ring B are either substituted or unsubstituted naphthalene rings.

[0016]

[0017] in,

[0018] HAr represents substituted or unsubstituted nitrogen-containing (3-membered to 30-membered) heteroaryl groups;

[0019] L3 represents an unsubstituted or tritium-substituted naphthyl group, an unsubstituted or tritium-substituted biphenyl group, an unsubstituted or tritium-substituted terphenyl group, or an unsubstituted or tritium-substituted -phenyl-naphthyl- group; and

[0020] R1 to R8 each independently represent hydrogen, tritium, or an unsubstituted (C6-C30) aryl group or a (C6-C30) aryl group substituted with at least one of tritium and (C6-C30) aryl.

[0021] Beneficial effects of the present invention

[0022] By using specific combinations of compounds disclosed herein as the main material, organic electroluminescent devices with higher luminous efficiency and / or longer lifetime characteristics compared to conventional organic electroluminescent devices can be provided, and display systems or lighting systems using said organic electroluminescent devices can be manufactured. Detailed Implementation

[0023] This disclosure will be described in detail below. However, the following description is intended to explain this disclosure and is not intended to limit the scope of this disclosure in any way.

[0024] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0025] The term "multiple organic electroluminescent materials" in this disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials may be contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials may be a combination of at least two compounds, said materials may contain at least one of the following: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0026] The term "multiple host materials" in this disclosure refers to an organic electroluminescent material comprising a combination of at least two host materials. It can mean both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. The multiple host materials of this disclosure can be included in any light-emitting layer constituting the organic electroluminescent device. Two or more compounds included in the multiple host materials of this disclosure can be included in one light-emitting layer or can be included separately in different light-emitting layers. For example, two or more host materials can be mixed and evaporated to form a layer, or simultaneously co-evaporated separately to form a layer.

[0027] In this document, the terms "(C6-C30) aryl" or "(C6-C30) arylene" refer to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton. The number of carbon atoms in the ring skeleton is preferably 6 to 20, and more preferably 6 to 15. The aforementioned aryl or arylene group may be partially saturated and may include a spirostructure. The aforementioned aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, phenylphenanthryl, anthracene, indole, benzo[a]phenanthryl, pyrene, tetraphenyl, floryl, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, spiro[fluorene-benzo[fluorene]]yl, azuleyl, etc. More specifically, aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzo[anthrayl], 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, naphthyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Benzophenanthryl, 2-Benzophenanthryl, 3-Benzophenanthryl, 4-Benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[fluorenyl]fluorenyl, dibenzo[fluorenyl]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, 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-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzo[fluoranthyl]fluorenthyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-Dimethylphenyl, 3,4-Dimethylphenyl, 2,5-Dimethylphenyl, mesitylene, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 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.

[0028] The terms "(3- to 50-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" refer to aryl or arylene groups having 3 to 50 or 3 to 30 ring skeleton atoms, preferably 3 to 30, more preferably 5 to 20, and including at least one (preferably 1 to 4) heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl (or heteroarylene) group can be a monocyclic ring or a fused ring condensed with at least one benzene ring; it can be partially saturated; it can be a heteroaryl or heteroarylene group formed by linking at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and it can contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiophene, pyrrole, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryl groups, such as benzofuranyl, benzothiophene, isobenzofuranyl, diphenyl Benzofurano, benzonaphthiofuran, dibenzothiophene, benzonaphthiophene, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, carbazole, benzocarbazole, phenoxazinyl, phenanthidyl, phenanthoxazolyl, benzom-dioxacyclopentenyl, etc. More specifically, heteroaryl groups may include 1-pyrrole, 2-pyrrole, 3-pyrrole, pyrazinyl, 2-pyridinyl, 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-indololinyl, 2-indololinyl, 3-indololinyl, 5-indololinyl, 6-indololinyl, 7-indololinyl, 8-indololinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 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-Furanyl, 3-Furanyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6 -benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl4-Isoquinolinyl, 5-Isoquinolinyl, 6-Isoquinolinyl, 7-Isoquinolinyl, 8-Isoquinolinyl, 2-Quinoxolinyl, 5-Quinoxolinyl, 6-Quinoxolinyl, 1-Carbazoleyl, 2-Carbazoleyl, 3-Carbazoleyl, 4-Carbazoleyl, 9-Carbazoleyl, Azacarbazole-1-yl, Azacarbazole-2-yl, Azacarbazole-3-yl, Azacarbazole-4-yl, Azacarbazole-5-yl, Azacarbazole-6-yl, Azacarbazole-7-yl, Azacarbazole 8-yl, azacarbazolyl-9-yl, 1-phenanthrynyl, 2-phenanthrynyl, 3-phenanthrynyl, 4-phenanthrynyl, 6-phenanthrynyl, 7-phenanthrynyl, 8-phenanthrynyl, 9-phenanthrynyl, 10-phenanthrynyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1- 2-Methylpyrrolo-3-yl, 2-Methylpyrrolo-4-yl, 2-Methylpyrrolo-5-yl, 3-Methylpyrrolo-1-yl, 3-Methylpyrrolo-2-yl, 3-Methylpyrrolo-4-yl, 3-Methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1- Indole, 4-tert-butyl-1-indole, 2-tert-butyl-3-indole, 4-tert-butyl-3-indole, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-siliconfluorenyl, 2-siliconfluorenyl, 3-siliconfluorenyl, 4-siliconfluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, etc. "Halogens" include F, Cl, Br, and I.

[0029] Furthermore, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that the two substituents are adjacent to each other, and for example, when the two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that the two substituents are at positions 1 and 3, and for example, when the two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that the two substituents are at positions 1 and 4, and for example, when the two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0030] In this document, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). In this disclosure, the substituents of substituted benzene, substituted naphthalene, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted alkyl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or dialkylamino, substituted mono- or diarylamino, and substituted alkylarylamino are each independently at least one selected from the group consisting of: tritium; Halogen; cyano; carboxyl; nitro; hydroxyl; (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)heterocyclic alkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or occupied by at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino. A substituted (3- to 50-membered) heteroaryl; an unsubstituted (C6-C30) aryl or substituted with at least one of tritium, cyano, (C1-C30) alkyl, (3- to 50-membered) heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di- -(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboroncarbonyl; di(C1-C30)alkylboroncarbonyl; (C1-C30)alkyl(C6-C30)arylboroncarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.Preferably, the substituent may be at least one selected from the group consisting of: tritium; (C1-C20)alkyl; (C6-C25)aryl, unsubstituted or substituted with at least one of tritium, (C1-C20)alkyl, (3- to 30-membered)heteroaryl, and di(C6-C25)arylamino; (3- to 30-membered)heteroaryl, unsubstituted or substituted with at least one of (C1-C20)alkyl and (C6-C25)aryl; and di(C6-C20)arylamino. More preferably, the substituent may be at least one selected from the group consisting of: tritium; (C1-C10)alkyl; and (C6-C20)aryl, unsubstituted or substituted with one or more tritium groups. For example, the substituent may be at least one selected from the group consisting of: tritium; methyl; unsubstituted or substituted with one or more tritium groups; naphthyl; biphenyl; and terphenyl.

[0031] In the formula disclosed herein, each of the heteroaryl, heteroarylide, and heterocycloalkyl groups may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one of the following groups: hydrogen, tritium, 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 tri(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 tri(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.

[0032] In Formula 1, rings A, B, and C each independently represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring. According to one embodiment of this disclosure, rings A, B, and C may each independently be an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[0033] In Equation 1, n represents an integer of 0 or 1; Y represents O, S, or NRa; and Ra represents -L2-Ar2. If n is 0, then both ring A and ring B represent substituted or unsubstituted naphthalene rings, preferably unsubstituted naphthalene rings.

[0034] Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl group; a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur; or a substituted or unsubstituted di(C6-C30) arylamino group. According to one embodiment of this disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl group; a substituted or unsubstituted (5- to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur; or a substituted or unsubstituted di(C6-C25) arylamino group. According to another embodiment of this disclosure, Ar1 and Ar2 each independently represent an unsubstituted (C6-C25) aryl group or a (C1-C10) alkyl group substituted with one or more (C6-C18) aryl groups and containing at least one of nitrogen, oxygen and sulfur (5- to 20-membered) heteroaryl group; or an unsubstituted (C6-C18) arylamino group or a (C6-C18) arylamino group substituted with one or more (C6-C18) aryl groups. Specifically, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted benzofuran-pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted carbazole, or a substituted or unsubstituted benzo[] Carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted benzofuran, substituted or unsubstituted naphthidyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuran, substituted or unsubstituted benzonaphthothiophene, substituted or unsubstituted diphenylamino, substituted or unsubstituted naphthylphenylamino, or substituted or unsubstituted biphenylphenylamino.For example, Ar1 and Ar2 can each independently represent phenyl; naphthyl; biphenyl; terphenyl; dimethylfluorenyl; dimethylbenzofluorenyl; spirodifluorenyl; pyridyl substituted with one or more phenyl groups; pyrimidinyl substituted with one or more phenyl groups; triazine substituted with one or more phenyl groups; quinolinyl substituted with one or more phenyl groups; quinazolinyl substituted with at least one of phenyl and naphthyl groups; quinoxalinyl substituted with at least one of phenyl and naphthyl groups; naphridinyl substituted with one or more phenyl groups; dibenzothiophene; dibenzothiofuranyl; carbazoyl substituted with one or more phenyl groups; benzofuran-pyrimidinyl substituted with one or more phenyl groups; benzoquinazolinyl substituted with one or more phenyl groups; benzoquinoxalinyl substituted with one or more phenyl groups; benzocarbazoyl substituted with one or more phenyl groups; diphenylamino; phenylnaphthylamino; phenylbiphenylamino; diphenylamino substituted with one or more naphthyl groups; phenylbiphenylamino substituted with one or more naphthyl groups, etc.

[0035] L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of this disclosure, L1 and L2 each independently represent a single bond; an unsubstituted (C6-C18) aryl group; or an unsubstituted or substituted (5- to 20-membered) heteroaryl group. For example, L1 and L2 can each independently represent a single bond; phenylene; naphthylene; biphenylene; triazineyl substituted with one or more phenyl groups; pyrimidinyl substituted with one or more phenyl groups; quinolinyl; unsubstituted or substituted with one or more phenyl groups; unsubstituted or substituted with one or more phenyl groups; naphthidyl; benzofuranopyrimidinyl; benzoquinazolinyl; carbazoyl; benzoquinazolinyl; benzocarbazoyl, etc.

[0036] Equation 1 can be represented by any one of the following equations 1-1 to 1-7.

[0037]

[0038]

[0039] In Equations 1-1 to 1-7, Ar1, L1, and Y are defined as in Equation 1.

[0040] In equations 1-1 to 1-7, R 11 To R 27Each of these can be independently represented as hydrogen, tritium, 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 tri(C1-C30) alkylsilyl, or substituted or unsubstituted di(C1-C30) alkylsilyl. Alkyl (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(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. For example, R 11 To R 27 It can represent hydrogen.

[0041] In equations 1-1 to 1-7, a, d, h, m, q, and r each independently represent integers from 1 to 6; and b, c, e, f, g, i, j, k, l, o, and p each independently represent integers from 1 to 4, where if a to m and o to r are each independent integers of 2 or greater, then each R 11 Each R 12 Each R 13 Each R 14 Each R 15 Each R 16 Each R 17 Each R 18 Each R 19 Each R 20 Each R 21 Each R 22 Each R 23 Each R 24 Each R 25 Each R 26 and each R 27 They can be the same or different.

[0042] In Formula 2, HAr represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5- to 25-membered) heteroaryl group containing at least one nitrogen. According to another embodiment of the present disclosure, HAr represents a (5- to 20-membered) heteroaryl group substituted with one or more (C6-C30) aryl groups and containing at least one nitrogen. Specifically, HAr can represent substituted or unsubstituted triazine, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphridinyl, or substituted or unsubstituted benzothiophenepyrimidinyl. For example, HAr can represent substituted triazine, wherein the substituent of the substituted triazine can be at least one, preferably two, selected from the group consisting of: phenyl; phenyl substituted with one or more tritium groups; naphthyl; biphenyl; and terphenyl.

[0043] In Formula 2, L3 represents an unsubstituted or tritium-substituted naphthylene, an unsubstituted or tritium-substituted biphenylene, an unsubstituted or tritium-substituted terphenylene, or an unsubstituted or tritium-substituted -phenyl-naphthylene-. According to one embodiment of this disclosure, L3 represents an unsubstituted or tritium-substituted naphthylene; an unsubstituted biphenylene; or an unsubstituted -phenyl-naphthylene-. The -phenyl-naphthylene- means that the phenylene group therein can be bonded to HAr or that the naphthylene group therein can be bonded to HAr.

[0044] In Formula 2, R1 to R8 each independently represent hydrogen, tritium, or an unsubstituted (C6-C30) aryl group, or a (C6-C30) aryl group substituted with at least one of tritium and (C6-C30) aryl groups. According to one embodiment of this disclosure, R1 to R8 each independently represent hydrogen, tritium, or an unsubstituted (C6-C25) aryl group, or a (C6-C30) aryl group substituted with one or more (C6-C30) aryl groups. According to another embodiment of this disclosure, R1 to R8 each independently represent hydrogen, tritium, or an unsubstituted (C6-C18) aryl group. R1 to R8 may be the same as or different from each other. For example, R1 to R8 may each independently represent hydrogen, tritium, phenyl, naphthyl, or biphenyl.

[0045] According to one embodiment of this disclosure, formula 2 can be represented by formula 3 below.

[0046]

[0047] In Equation 3, Ar 21 and Ar 22 Each of these terms independently represents an unsubstituted phenyl group or a phenyl group substituted with one or more tritium groups, an unsubstituted biphenyl group or a biphenyl group substituted with one or more tritium groups, a terphenyl group or a terphenyl group or a naphthyl group or a naphthyl group substituted with one or more tritium groups; L 21 R1 represents an unsubstituted or tritium-substituted naphthyl group, or an unsubstituted or tritium-substituted biphenyl group; R1, R4, R5, and R8 each independently represent hydrogen, tritium, an unsubstituted or tritium-substituted phenyl group, an unsubstituted or tritium-substituted biphenyl group, an unsubstituted or tritium-substituted terphenyl group, or an unsubstituted or tritium-substituted naphthyl group; and R2, R3, R6, and R7 each independently represent hydrogen or tritium; provided that if Ar 21 and Ar 22 If both represent phenyl, then at least one of R1, R4, R5, and R8 is not hydrogen or tritium.

[0048] The compounds represented by Formula 1 can be specifically exemplified by the following compounds, but are not limited thereto.

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] The compound represented by Formula 2 can be exemplified by any of the following compounds, but is not limited thereto.

[0057]

[0058]

[0059]

[0060] A combination of at least one of compounds H1-1 to H1-150 and at least one of compounds H2-1 to H2-55 can be used in organic electroluminescent devices.

[0061] According to one embodiment of this disclosure, an organic electroluminescent compound represented by Formula 3 is provided. The compound represented by Formula 3 can be specifically exemplified by compounds H2-2 to H2-13, H2-15 to H2-22, H2-24 to H2-28, H2-32 to H2-35, H2-43, H2-46, H2-47, and H2-50 to H2-55, but is not limited thereto. Furthermore, this disclosure can provide an organic electroluminescent device comprising an organic electroluminescent compound represented by Formula 3.

[0062] The compound represented by Formula 1 according to this disclosure can be prepared as shown in reaction scheme 1 below and by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by reference to Korean Patent Application Publication Nos. 2015-0135109 (published December 2, 2015), 2016-0099471 (published August 22, 2016), 2015-0077513 (published July 8, 2015) and 2017-0129599 (published November 27, 2017), but is not limited thereto.

[0063] [Reaction Scheme 1]

[0064]

[0065] The compounds represented by formula 2 or 3 according to this disclosure can be prepared as shown in reaction scheme 2 below and by synthetic methods known to those skilled in the art, but are not limited thereto.

[0066] [Reaction Scheme 2]

[0067]

[0068] In reaction schemes 1 and 2, Ar1, L1, Ra, R 18 To R 20 h to j, R1 to R8, L3, and HAr are as defined in Formulas 1, 1-4, and 2, where Hal represents I, Br, Cl, ONf (nonafluorobutanesulfonyl), or OTf (trifluoromethanesulfonate).

[0069] Although illustrative synthetic examples of compounds represented by Formulas 1 to 3 have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even when substituents defined in Formulas 1 to 3 above but not specified in the specific synthetic examples are bonded. For example, tritium-containing compounds of formulas 1 to 3 can be prepared by treating non-tritated compounds with a tritized solvent or D6-benzene in the presence of an H / D exchange catalyst (such as a Lewis acid, such as aluminum trichloride or ethylaluminum chloride, trifluoromethanesulfonic acid or trifluoromethanesulfonic acid-D). Furthermore, the degree of tritization can be controlled by adjusting reaction conditions (such as reaction temperature and time, acid equivalent, etc.).

[0070] The organic electroluminescent device according to this disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may contain a variety of organic electroluminescent materials, including a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of this disclosure, the organic electroluminescent device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, and the light-emitting layer contains one or more compounds represented by Formula 1 and one or more compounds represented by Formula 2.

[0071] The electrodes can be semi-transparent reflective electrodes or reflective electrodes, and depending on the material, they can be top-emitting, bottom-emitting, or side-emitting. The hole injection layer can be further doped with p-type dopant, and the electron injection layer can be further doped with n-type dopant.

[0072] The luminescent layer comprises a host and dopants. The host comprises multiple host materials. A compound represented by Formula 1 may be included as a first host compound of the multiple host materials, and a compound represented by Formula 2 may be included as a second host compound of the multiple host materials. The weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50. When a layer contains two or more materials, they may be mixed and evaporated to form the layer, or they may be co-evaporated simultaneously and separately to form the layer.

[0073] The light-emitting layer is the layer from which light is emitted, and can be a single layer or a multilayer in which two or more layers are stacked. Among the various host materials according to this disclosure, the first host material and the second host material can both be contained in a single layer, or they can be contained in different light-emitting layers. According to one embodiment of this disclosure, the doping concentration of the dopant compound relative to the host compound in the light-emitting layer is less than about 20 wt%.

[0074] The organic electroluminescent device disclosed herein 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 injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of this disclosure, in addition to the various host materials disclosed herein, the organic electroluminescent device may further include an amine-based compound as at least one of the following: a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, and an electron blocking material. Furthermore, according to one embodiment of this disclosure, in addition to the various host materials disclosed herein, the organic electroluminescent device may further include an azazine-based compound as at least one of the following: an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0075] The dopant included in the organic electroluminescent device according to the present disclosure may be at least one phosphorescent dopant or a fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device according to the present disclosure is not particularly limited, but may be selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, preferably from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, and more preferably from ortho-metallized iridium complexes.

[0076] The dopants included in the organic electroluminescent devices of this disclosure may include, but are not limited to, compounds represented by formula 101.

[0077]

[0078] In Equation 101, L is selected from the following structures 1 and 2:

[0079]

[0080]

[0081] R 100 To R 103 Each can independently represent hydrogen, tritium, halogen, unsubstituted or substituted (C1-C30) alkyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C6-C30) aryl group, cyano group, substituted or unsubstituted (3- to 30-membered) heteroaryl group, or substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to an adjacent R. 100 To R 103 One or more of the rings may be formed together with pyridine to form one or more rings, such as substituted or unsubstituted quinoline, benzofuran pyridine, benzothiophene pyridine, indene pyridine, benzofuran quinoline, benzothiophene quinoline, or indene quinoline ring;

[0082] R 104 To R 107 Each can independently represent hydrogen, tritium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to an adjacent R. 104 To R 107 One or more of the naphthalene rings can form a ring with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenepyridine, benzofuran-pyridine, or benzothiophene-pyridine rings;

[0083] R 201 To R 211 Each can independently represent hydrogen, tritium, halogen, unsubstituted or substituted (C1-C30) alkyl group, substituted or unsubstituted (C3-C30) cycloalkyl group, or substituted or unsubstituted (C6-C30) aryl group; or may be attached to an adjacent R. 201 To R 211 One or more of them form a ring; and

[0084] n' represents the integers 1 to 3.

[0085] Specific examples of dopant compounds are shown below, but are not limited to.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods can be used.

[0092] In wet film-forming methods, thin films can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no problems with film-forming ability.

[0093] Furthermore, compounds represented by Formula 1 and those represented by Formula 2 or 3 can be used for film formation in the methods listed above, typically via co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and current is simultaneously applied to two chambers to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and current is applied to a chamber to evaporate the materials.

[0094] The organic electroluminescent material according to this disclosure can be used as a luminescent material for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting devices, such as side-by-side or stacked structures, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) luminescent components, or color conversion material (CCM) methods, etc., and this disclosure can also be applied to such white organic light-emitting devices.

[0095] Furthermore, the organic electroluminescent materials according to this disclosure can also be used in organic electroluminescent devices containing quantum dots (QDs).

[0096] This disclosure can provide display systems incorporating various body materials disclosed herein. Furthermore, display systems or lighting systems can be manufactured using the organic electroluminescent devices of this disclosure. Specifically, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be manufactured using the organic electroluminescent devices of this disclosure; or lighting systems, such as outdoor or indoor lighting systems.

[0097] The preparation methods of the compounds of this disclosure and the properties of the compounds will be explained in detail below with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0098] Example 1: Preparation of compound H1-131

[0099]

[0100] Synthesis of Compound 1

[0101] 7H-dibenzo[c,g]carbazole (60 g, 224 mmol) was dissolved in 900 mL of N,N-dimethylformamide (DMF) in a flask, and the mixture was cooled to 0 °C and stirred. N-bromosuccinimide (NBS) (36 g, 202 mmol) was dissolved in 220 mL of DMF and then added dropwise to the mixture over 2.5 hours. The resulting mixture was stirred for 2 hours at room temperature. After the reaction was complete, the reaction product was washed with an aqueous solution of Na₂S₂O₃ and water, the organic layer was extracted with ethyl acetate, and the residual water was removed with MgSO₄. The residue was dried and separated through a silica filter to obtain compound 1 (79 g, yield: 79%).

[0102] Synthesis of Compound 2

[0103] Compound 1 (76 g, 220 mmol), iodobenzene (90 g, 439 mmol), CuI (20.90 g, 110 mmol), ethylenediamine (EDA) (13 g, 110 mmol), and K3PO4 (139 g, 659 mmol) were added to 1.1 L of toluene, and the mixture was stirred under reflux for 2.5 h. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The residue was separated by column chromatography to obtain compound 2 (55.1 g, yield: 60%).

[0104] Synthesis of Compound 3

[0105] Compound 2 (54.6 g, 129 mmol), 2-chloroaniline (20 g, 155 mmol), Pd(OAc)2 (2.9 g, 13 mmol), P(t-Bu)3 (5.2 g, 26 mmol), sodium tert-butoxide (NaOt-Bu) (31 g, 323 mmol), and 650 mL of toluene were stirred under reflux for 4 hours. The mixture was cooled to room temperature, and NH4Cl (aqueous) was added. The reaction product 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 compound 3 (47.9 g, yield: 79%).

[0106] Synthesis of Compound 4

[0107] Compound 3 (48 g, 103 mmol), Pd(OAc)2 (2.3 g, 10 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (7.6 g, 21 mmol), Cs2CO3 (100 g, 308 mmol), and 400 mL of N,N-dimethylacetamide (DMA) were stirred under reflux for 1 hour. The reaction product was cooled to room temperature and NH4Cl (aqueous) was added. The organic layer was extracted with dichloromethane (MC) and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 4 (44 g, yield: 79%).

[0108] Synthesis of compound H1-131

[0109] Compound 4 (5 g, 12 mmol), iodobenzene (3.5 g, 17 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.6 g, 23 mmol), and K3PO4 (4.9 g, 23 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and subjected to diatomaceous earth filtration using MC. The filtrate was distilled under reduced pressure and separated by column chromatography (using MC / Hex) to obtain compound H1-131 (1.3 g, yield: 22%).

[0110] 1H NMR (600MHz, DMSO, δ) 9.16-9.15 (d, 1H), 8.99-8.98 (d, 1H), 8.14-8.13 (d, 1H), 7.94-7.93 (d, 1H), 7.94-7.68 (m, 9H ), 7.65-7.61(m, 3H), 7.60-7.54(m, 3H), 7.25-7.21(m, 2H), 7.08-7.07(d, 1H), 6.78-6.76(m, 1H) 5.95-5.94(d, 1H)

[0111] MW UV PL Melting point H1-131 508.62 342nm 427nm 184℃

[0112] Example 2: Preparation of compound H1-132

[0113]

[0114] Compound 4 (7 g, 16 mmol), 2-bromonaphthalene (6.7 g, 32 mmol), CuI (1.5 g, 8 mmol), 1,2-diaminocyclohexane (3.7 g, 32 mmol), and K3PO4 (10.3 g, 49 mmol) were added to 80 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and subjected to diatomaceous earth filtration using MC. The filtrate was distilled under reduced pressure and separated by column chromatography (using MC / Hex) to obtain compound H1-132 (1.3 g, yield: 22%).

[0115] 1 H NMR (600MHz, DMSO, δ) 9.17-9.15 (d, 1H), 9.00-8.99 (d, 1H), 8.31-8.30 (m, 2H), 8.20-8.18 (d, 1H), 8.15-8.14 (d, 1H), 8.11-8.10 (d, 1H), 7.95-7 .94(d,1H),7.83-7.79(m,5H),7.73-7.69(m,4H),7.60-7.57(m,4H),7. 21-7.18(m,2H),7.14-7.13(d,1H),6.78-6.77(t,1H)5.98-5.96(d,1H)

[0116] MW UV PL Melting point H1-132 558.68 340nm 431nm 263℃

[0117] Example 3: Preparation of compound H1-134

[0118]

[0119] Synthesis of Compound 5

[0120] Compound 1 (15 g, 220 mmol), 3-iodo-1,1′-biphenyl (18 g, 65 mmol), CuI (4.1 g, 22 mmol), ethylenediamine (2.6 g, 43 mmol), and K3PO4 (23 g, 108 mmol) were added to 216 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to obtain compound 5 (16 g, yield: 74%).

[0121] Synthesis of Compound 6

[0122] Compound 5 (15 g, 30 mmol), 2-chloroaniline (7.7 g, 60 mmol), Pd(OAc)2 (0.67 g, 3 mmol), P(t-Bu)3 (1.2 g, 6 mmol), NaOt-Bu (7.2 g, 75 mmol), and 150 mL of toluene were stirred under reflux for 2 hours. The reaction product was cooled to room temperature, and NH4Cl (aqueous) was added. The organic layer was extracted with EA and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 6 (10.1 g, yield: 62%).

[0123] Synthesis of Compound 7

[0124] Compound 6 (10 g, 18 mmol), Pd(OAc)2 (0.41 g, 1.8 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.35 g, 3.7 mmol), Cs2CO3 (18 g, 55 mmol), and 92 mL of DMA were stirred under reflux for 1 hour. The reaction product was cooled to room temperature, and NH4Cl (aqueous) was added. 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 compound 7 (7.1 g, yield: 76%).

[0125] Synthesis of compound H1-134

[0126] Compound 7 (6.7 g, 13 mmol), 3-iodo-1,1′-biphenyl (7.4 g, 26 mmol), Cu powder (0.42 g, 7 mmol), and K₂CO₃ (3.6 g, 26 mmol) were added to 70 mL of o-dichlorobenzene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and subjected to diatomaceous earth filtration using MC. The filtrate was distilled under reduced pressure and separated by column chromatography (using MC / Hex) to obtain compound H1-134 (3.1 g, yield: 36%).

[0127] 1 H NMR (600MHz, DMSO, δ) 9.18-9.17 (d, 1H), 9.01-9.00 (d, 1H), 8.16-8.15 (d, 1H), 8.11-8.09 (d, 1H), 8.06-8.05 (m, 2H), 8.00-7 .79(m,7H),7.73-7.57(m,8H),7.48-7.38(m,6H),7.30-7.28(t,1H),7.22-7.18(m,2H),6.80-6.78(t,1H),6.07-6.06(d,1H)

[0128] MW Melting point H1-134 660.82 259℃

[0129] Example 4: Preparation of compound H1-133

[0130]

[0131] Compound 4 (4 g, 9.25 mmol), 3-iodo-1,1′-biphenyl (3.1 g, 11.1 mmol), tris(dibenzylacetone)dipalladium(0)(Pd2(dba)3) (0.42 g, 0.46 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.38 g, 0.92 mmol), and NaOt-Bu (2.2 g, 23.13 mmol) were added to 46 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was extracted with MC, distilled under reduced pressure, and separated by column chromatography (using MC / Hex) to obtain compound H1-133 (1.2 g, yield: 23%).

[0132] 1 H NMR(600MHz, DMSO, δ)9.17-9.15(d,1H),9.00-8.98(d,1H),8.15-8.13(d,1H),8.07-8.06 (d, 1H), 7.98 (m, 1H), 7.95-7.94 (d, 1H), 7.88-7.86 (t, 1H), 7.82-7.80 (m, 7H), 7.71-7.67 (m, 2H), 7.65-7.61 (m, 2H), 7.60-7.55 (m, 2H), 7.49-7.47 (t, 2H), 7.42-7.39 (t, 1H), 7.30 -7.27(t, 1H), 7.26-7.23(t, 1H), 7.20-7.19(d, 1H), 6.80-6.77(t, 1H), 5.97-5.95(d, 1H)

[0133] MW Melting point H1-133 584.7 249.6℃

[0134] Example 5: Preparation of compound H1-135

[0135]

[0136] Synthesis of Compound 1

[0137] 7H-dibenzo[c,g]carbazole (50 g, 187 mmol) was dissolved in 750 mL of DMF in a flask, and the mixture was cooled to 0 °C and stirred. NBS (30 g, 168 mmol) was dissolved in 250 mL of DMF and then added dropwise to the mixture over 1 hour. The resulting mixture was stirred at room temperature for 2 hours. After the reaction was complete, the reaction product was washed with an aqueous solution of Na₂S₂O₃ and water, the organic layer was extracted with ethyl acetate, and the residual water was removed with MgSO₄. The residue was dried and separated through a silica filter to obtain compound 1 (40 g, yield: 62%).

[0138] Synthesis of Compound 8

[0139] Compound 1 (11 g, 32 mmol), 4-iodo-1,1′-biphenyl (17.8 g, 64 mmol), CuI (3.0 g, 15.9 mmol), ethylenediamine (1.91 g, 31.8 mmol), and K3PO4 (20.3 g, 95 mmol) were added to 160 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to obtain compound 8 (13.0 g, yield: 82%).

[0140] Synthesis of Compound 9

[0141] Compound 8 (13.0 g, 26 mmol), 2-chloroaniline (6.7 g, 52 mmol), Pd(OAc)2 (0.59 g, 2.6 mmol), P(t-Bu)3 (1.1 g, 5.2 mmol), NaOt-Bu (6.3 g, 65 mmol), and 130 mL of toluene were stirred under reflux for 4 hours. The reaction product was cooled to room temperature, and NH4Cl (aqueous) was added. The organic layer was extracted with EA and dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 9 (9.2 g, yield: 65%).

[0142] Synthesis of Compound 10

[0143] Compound 9 (9.2 g, 17 mmol), Pd(OAc)2 (0.38 g, 2 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.2 g, 3 mmol), Cs2CO3 (138 g, 42 mmol), and 70 mL of DMA were stirred under reflux for 1 hour. The reaction product was cooled to room temperature, and NH4Cl (aqueous) was added. The resulting solid was distilled under reduced pressure and separated by column chromatography to obtain compound 10 (6.0 g, yield: 70%).

[0144] Synthesis of compound H1-135

[0145] Compound 10 (6 g, 12 mmol), 2-bromonaphthalene (4.9 g, 24 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.7 g, 24 mmol), and K3PO4 (7.5 g, 35 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature. The organic layer was then separated by adding ethyl acetate and water and dried over magnesium sulfate. The residue was filtered through diatomaceous earth using MC. The filtrate was distilled under reduced pressure and separated by column chromatography (using MC / Hex) to obtain compound H1-135 (2.1 g, yield: 28%).

[0146] 1 H NMR(600MHz, DMSO, δ)9.18-9.17(d,1H),9.01-8.99(d,1H),8.33-8.31(m,2H ), 8.20-8.19(d, 1H), 8.17-8.15(d, 1H), 8.12-8.08(m, 3H), 7.98-7.97(d, 1H ), 7.93-7.89 (m, 4H), 7.70-7.68 (m, 5H), 7.63-7.57 (m, 5H) 7.50-7.48 (t, 1H) ,7.22-7.19(t,1H),7.15-7.13(d,1H),6.77-6.74(td,1H),6.16-6.15(d,1H)

[0147] MW Melting point H1-135 508.62 294℃

[0148] Example 6: Preparation of compound H1-11

[0149]

[0150] Compound 1-1 (7 g, 13 mmol), dibenzo[b,d]furan-1-ylboronic acid (3 g, 14.3 mmol), K₂CO₃ (5.4 g, 39 mmol), and Pd(PPh₃)₄ (0.75 g, 0.65 mmol) were dissolved in 30 mL of H₂O, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120 °C for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-11 (5.7 g, yield: 70%).

[0151] 1 H NMR (600MHz, CDCl3, δ) 9.305 (s, 1H), 9.049-9.035 (d, J=8.4Hz, 1H), 8.379-8.367 (d, J=7.2Hz, 1 H), 8.022-8.008 (d, J=8.4Hz, 1H) 7.816-7.705 (m, 6H), 7.699-7.392 (m, 16H) 7.195-7.127 (m, 2H)

[0152] MW Melting point H1-11 642.73 154℃

[0153] Example 7: Preparation of compound H1-54

[0154]

[0155] Compounds 1-2 (5.7 g, 10.6 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.5 g, 11.7 mmol), K₂CO₃ (4.4 g, 31.8 mmol), and Pd(PPh₃)₄ (0.61 g, 0.653 mmol) were dissolved in 30 mL of H₂O, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120 °C for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-54 (1.2 g, yield: 18%).

[0156] 1 H NMR (600MHz, CDCl3, δ) 8.880 (s, 1H), 8.378-8.364 (d, J=8.4Hz, 1H), 8.297-8.284 (d, J=7.8Hz, 1H ), 8.000-7.987 (d, J=7.8Hz, 1H) 7.777-7.702 (m, 5H), 7.615-7.332 (m, 15H), 7.189-7.127 (m, 4H)

[0157] MW Melting point H1-54 624.73 239℃

[0158] Example 8: Preparation of compound H1-53

[0159]

[0160] Compounds 1-2 (5.0 g, 9.3 mmol), dibenzo[b,d]furan-4-ylboronic acid (2.2 g, 10.2 mmol), Pd(PPh3)4 (0.54 g, 0.47 mmol), and K2CO3 (2.6 g, 18.6 mmol) were dissolved in 20 mL of toluene, 8 mL of EtOH, and 10 mL of H2O in a flask, and the mixture was refluxed at 120 °C for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-53 (3.5 g, yield: 60%).

[0161] 1 H NMR (600MHz, DMSO3, δ) 9.210 (s, 1H), 8.516-8.502 (d, 1H), 8.408-8.395 (d, 1H), 8.219- 8.198(m, 2H), 8.115-8.109(t, 1H), 8.087-8.073(d, 1H), 8.040-8.028(d, 1H), 7.856-7. 842(d,1H),7.833-7.807(t,1H),7.733-7.611(m,9H),7.562-7.531(m,2H),7.515-7.4 90(t,1H),7.451-7.426(t,1H),7.293-7.279(d,1H),7.258-7.232(t,1H),7.119(s,1H)

[0162] MW Melting point H1-53 624.7 161℃

[0163] Example 9: Preparation of compound H1-13

[0164]

[0165] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (3.6 g, 9.285 mmol), 1-(4-bromophenyl)dibenzo[b,d]furan (3 g, 9.285 mmol), CuI (0.08 g, 0.464 mmol), EDA (0.5 g, 9.285 mmol), and K3PO4 (4.9 g, 23.21 mmol) were added to 50 mL of xylene, and the mixture was stirred for one day. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography (using MC / Hex) to obtain compound H1-13 (2.7 g, yield: 47%).

[0166] 1 H NMR (DMSO-d6) δ: 9.69 (s, 1H), 9.26 (d, J=8.3Hz, 1H), 8.69 (dd, J=7.7, 1.2Hz, 1H), 8.14 (dd, J=8.0, 1.1Hz, 1H), 7.97 (d, J=8.8Hz, 1H), 7.92 (s, 4H), 7.88 (d dd, J=8.2, 6.9, 1.3Hz, 1H), 7.82-7.76 (m, 4H), 7.73 (t, J=7.8Hz, 2H), 7.70-7 .48(m, 8H), 7.48-7.44(m, 2H), 7.42(td, J=7.3, 1.0Hz, 1H), 7.26-7.20(m, 1H)

[0167] MW Melting point H1-13 624.7 309.7℃

[0168] Example 10: Preparation of compound H1-5

[0169]

[0170] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (7.6 g, 18.88 mmol), 3-chloro-1,1′:2′,1″-terphenyl (5 g, 18.88 mmol), Pd2(dba)3 (0.86 g, 0.940 mmol), NaOt-Bu (4.5 g, 47.22 mmol), and P(t-Bu)3 (0.38 g, 1.888 mmol) were added to 100 mL of toluene, and the mixture was stirred for one day. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography (using MC / Hex) to obtain compound H1-5 (0.7 g, yield: 6.2%).

[0171] 1H NMR (DMSO-d6) δ: 9.58 (s, 1H), 9.20 (d, J=8.4Hz, 1H), 8.57 (d, J=7.8Hz, 1H), 8.11 (d, J=8.3Hz, 1H), 7.94 (d, J=8.9Hz, 1H), 7.84 (ddd, J= 8.3, 6.8, 1.3Hz, 1H), 7.72 (d, J=6.2Hz, 4H), 7.64-7.47 (m, 8H), 7.44 (dt, J=6.0, 1.9Hz, 1H), 7.40-7.17 (m, 10H), 6.50 (d, J=7.9Hz, 1H)

[0172] MW Melting point H1-5 610.7 194.6℃

[0173] Example 11: Preparation of compound H1-19

[0174]

[0175] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.1 g, 13 mmol), 9-(3-bromophenyl)-9H-carbazole (4.7 g, 14.6 mmol), Pd2(dba)3 (0.604 g, 0.66 mmol), SPhos (0.546 g, 1.33 mmol), and NaOt-Bu (3.20 g, 33.3 mmol) were added to 50 mL of xylene in a flask, and the mixture was stirred under reflux at 190 °C for 2 hours. After the reaction was complete, the organic layer was extracted with EA, dried over MgSO4, and separated by column chromatography. MeOH was then added to the separated product, and the resulting solid was filtered under reduced pressure to obtain compound H1-19 (4.4 g, yield: 53.0%).

[0176] 1 H NMR (600MHz, DMSO-d6, δ) 9.66 (s, 1H), 9.24 (d, J = 8.4Hz, 1H), 8.66 (d, J = 7.7Hz, 1H), 8.2 6 (d, J=7.8Hz, 2H), 8.13 (d, J=8.1Hz, 1H), 8.01-7.94 (m, 2H), 7.91-7.84 (m, 3H), 7.79 (d d, J=8.2, 1.8Hz, 1H), 7.77-7.74 (m, 2H), 7.69 (t, J=7.6Hz, 2H), 7.62-7.55 (m, 3H), 7.53 (d, J=8.1Hz, 1H), 7.49-7.45 (m, 2H), 7.39 (dd, J=14.4, 6.9Hz, 5H) 7.31 (t, J=7.5Hz, 2H)

[0177] MW Melting point H1-19 623.76 240℃

[0178] Example 12: Preparation of compound H1-6

[0179]

[0180] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.0 g, 13 mmol), 4′-bromo-1,1′:3′,1″-terphenyl (6.06 g, 20 mmol), Cu powder (1.307 g, 0.65 mmol), and K₂CO₃ (3.4 g, 26 mmol) were added to 60 mL of o-dichlorobenzene (o-DCB) in a flask, and the mixture was stirred under reflux at 230 °C for 12 hours. After the reaction was complete, the organic layer was extracted with EA, dried over MgSO₄, and separated by column chromatography. MeOH was then added to the separated product, and the resulting solid was filtered under reduced pressure to obtain compound H1-6 (1.3 g, yield: 16.3%).

[0181] 1 H NMR (600MHz, DMSO-d6, δ) 9.51 (s, 1H), 9.16 (d, J = 8.3Hz, 1H), 8.57 (d, J = 7.8Hz, 1H), 8. 10 (d, J=8.0Hz, 1H), 7.98-7.85 (m, 6H), 7.83 (t, J=7.6Hz, 1H), 7.76 (s, 1H), 7.70 (d, J= 8.1Hz, 1H), 7.61-7.51 (m, 5H), 7.51-7.42 (m, 3H), 7.38 (t, J=7.8Hz, 1H), 7.31 (t, J=7. 3Hz, 1H), 7.25 (d, J=8.0Hz, 1H), 7.13-7.06 (m, 4H), 7.03 (d, J=6.8Hz, 1H), 6.79 (s, 1H)

[0182] MW Melting point H1-6 610.74 296℃

[0183] Example 13: Preparation of compound H1-22

[0184]

[0185] Synthesis of Compound 11

[0186] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (10 g, 26.14 mmol), 1-bromo-3-iodobenzene (14.8 g, 52.29 mmol), CuI (2.5 g, 13.07 mmol), EDA (1.57 g, 26.14 mmol), and K3PO4 (13.8 g, 65.36 mmol) were added to 130 mL of toluene, and the mixture was stirred for one day. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography (using MC / Hex) to obtain compound 11 (9 g, yield: 64%).

[0187] Synthesis of Compound 12

[0188] Compound 11 (9 g, 16.74 mmol) was added to 85 mL of THF, and n-BuLi (2.5 M) (8.7 mL, 21.77 mmol) was slowly added while stirring at -78 °C for 1 hour. B(Oi-pr)3 (5.7 mL, 25.12 mmol) was added to the mixture, and the mixture was stirred for one day. After the reaction was complete, NH4Cl and distilled water were added to the reaction product, and the mixture was stirred for 30 minutes. Next, the resulting product was extracted with distilled water and EA, and the organic layer was concentrated to obtain compound 12 (6.8 g, yield: 80%).

[0189] Synthesis of compound H1-22

[0190] Compound 12 (6.8 g, 13.53 mmol), 4-bromo-9,9-dimethyl-9H-fluorene (3.7 g, 13.53 mmol), Pd(PPh3)4 (0.8 g, 0.676 mmol), and K2CO3 (3.7 g, 27.07 mmol) were added to 60 mL of toluene, 15 mL of EtOH, and 15 mL of distilled water, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and EA. The organic layer was distilled under reduced pressure and separated by column chromatography (using MC / Hex) to obtain compound H1-22 (1.5 g, yield: 17%).

[0191] 1H NMR (DMSO-d6) δ: 9.64 (s, 1H), 9.22 (d, J=8.4Hz, 1H), 8.64 (dt, J=7.6, 0.9Hz, 1H), 8.14-8.10 (m, 1H), 7.94 (d, J=8.9Hz, 1H), 7.90-7.77 (m, 3H), 7.6 8(s, 3H), 7.65-7.53(m, 7H), 7.53-7.33(m, 6H), 7.27(td, J=7.4, 1.1Hz, 1 H), 7.17 (d, J=7.6Hz, 1H), 6.92 (d, J=47.9Hz, 2H), 1.49 (d, J=17.3Hz, 6H)

[0192] MW Melting point H1-22 650.8 166.3℃

[0193] Example 14: Preparation of compound H1-4

[0194]

[0195] 7-Phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), 4-bromo-1,1′:2′,1″-terphenyl (4 g, 13.07 mmol), Pd2(dba)3 (0.6 g, 0.653 mmol), NaOt-Bu (3.8 g, 39.21 mmol), and SPhos (0.5 g, 1.307 mmol) were added to 70 mL of o-xylene, and the mixture was stirred for one day. After the reaction was complete, the product was cooled to room temperature and extracted with distilled water and MeOH. The extracted product was separated by column chromatography (using MC / Hex) to obtain compound H1-4 (6.3 g, yield: 78%).

[0196] NMR (DMSO-d6) δ: 9.63 (s, 1H), 9.23 (d, J=8.3Hz, 1H), 8.63 (dd, J=7.7, 1.1Hz, 1H), 8.12 (d, J=8.2Hz, 1H), 7.95 (d, J=8.9Hz, 1H), 7.85 (ddd, J=8.2, 6.8, 1.4H z, 1H), 7.79-7.73 (m, 2H), 7.72-7.66 (m, 3H), 7.60-7.47 (m, 8H), 7.44 (ddd, J= 8.2, 7.1, 1.3Hz, 1H), 7.38-7.33(m, 3H), 7.32-7.24(m, 2H), 7.22-7.14(m, 5H)

[0197] MW Melting point H1-4 610.7 288℃

[0198] Example 15: Preparation of compound H1-12

[0199]

[0200] Synthesis of Compound 13

[0201] Dibenzo[b,d]thiophene-1-ylboronic acid (20 g, 87.71 mmol), 1-bromo-3-iodobenzene (50 g, 175.4 mmol), Pd(PPh3)4 (5 g, 4.385 mmol), and Na2CO3 (18 g, 175.4 mmol) were added to 360 mL of toluene, 90 mL of distilled water, and 90 mL of EtOH, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the reaction product was cooled to room temperature and extracted with distilled water and EA. The organic layer was distilled under reduced pressure and separated by column chromatography (using Hex) to obtain compound 13 (20 g, yield: 67%).

[0202] Synthesis of compound H1-12

[0203] Compound 13 (4.4 g, 13.07 mmol), 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), Pd2(dba)3 (0.6 g, 0.653 mmol), SPhos (0.5 g, 1.307 mmol), and NaOt-Bu (3.7 g, 39.21 mmol) were added to 70 mL of o-xylene, and the mixture was stirred under reflux for 2 hours. After the reaction was complete, the product was cooled to room temperature and extracted with MeOH. The extracted product was separated by column chromatography (using MC / Hex) to obtain compound H1-12 (5.1 g, yield: 60%).

[0204] 1 H NMR (DMSO-d6) δ: 9.63 (s, 1H), 9.22 (d, J=8.4Hz, 1H), 8.64 (dd, J=7.5, 1.2Hz, 1H), 8.14- 8.09 (m, 2H), 8.07 (dt, J=8.1, 0.9Hz, 1H), 7.94 (d, J=8.9Hz, 1H), 7.91-7.82 (m, 3H), 7.72 (d, J=2.0Hz, 1H), 7.67 (d, J=7.6Hz, 2H), 7.63-7.48 (m, 8H), 7.48-7.41 (m, 2H), 7.40 (d, J=6.1Hz, 1H), 7.36 (td, J=7.4, 1.0Hz, 1H), 7.33 (d, J=7.3Hz, 1H), 7.09 (d, J=49.0Hz, 2H)

[0205] MW Melting point H1-12 640.7 226.7℃

[0206] Example 16: Preparation of compound H2-3

[0207]

[0208] Synthesis of Compound 2-1

[0209] 2-Chloro-4,6-bis(naphth-2-yl)-1,3,5-triazine (20 g, 79.7 mmol), (4-bromonaphth-1-yl)boronic acid (32.2 g, 87.7 mmol), Pd(PPh3)4 (4.6 g, 3.985 mmol), and Cs2CO3 (65 g, 199.25 mmol) were added to 400 mL of toluene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the product was cooled to room temperature, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 2-1 (30 g, yield: 74%).

[0210] Synthesis of compound H2-3

[0211] Compound 2-1 (10 g, 19.7 mmol), 9H-carbazole (3.0 g, 17.9 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), SPhos (0.73 g, 1.79 mmol), and NaOt-Bu (4.3 g, 44.75 mmol) were dissolved in 90 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the reaction product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-3 (1.5 g, yield: 13%).

[0212] MW Melting point H2-3 624.75 265℃

[0213] Example 17: Preparation of compound H2-10

[0214]

[0215] Synthesis of compound 2-2

[0216] 4-Bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), and Na2CO3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the product was cooled to room temperature, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 2-2 (9 g, yield: 91%).

[0217] Synthesis of compound H2-10

[0218] Compound 2-1 (8.5 g, 13.5 mmol), compound 2-2 (3.0 g, 12.3 mmol), Pd2(dba)3 (0.56 g, 0.615 mmol), SPhos (0.51 g, 1.23 mmol), and NaOt-Bu (2.9 g, 30.75 mmol) were dissolved in 60 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the reaction product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-10 (2.8 g, yield: 32.5%).

[0219] MW Melting point H2-10 700.85 260.3℃

[0220] Example 18: Preparation of compound H2-8

[0221]

[0222] 4-Phenyl-9H-carbazole (3.0 g, 12.3 mmol), 2-(4-bromonaphthyl-1-yl)-4,6-diphenyl-1,3,5-triazine (5.4 g, 12.3 mmol), Pd2(dba)3 (0.56 g, 0.62 mmol), SPhos (0.51 g, 1.23 mmol), and NaOt-Bu (2.4 g, 24.7 mmol) were added to 62 mL of o-xylene in a flask, and the mixture was stirred under reflux for 6 hours. After the reaction was complete, the reaction product was cooled to room temperature, and MeOH was added to it while stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H2-8 (3.3 g, yield: 45%).

[0223] MW Melting point H2-8 600.71 254℃

[0224] Example 19: Preparation of compound H2-2

[0225]

[0226] Compound A (8.0 g, 16.4 mmol), 9H-carbazole (3.0 g, 18.0 mmol), Pd2(dba)3 (0.9 g, 0.8 mmol), SPhos (0.7 g, 1.64 mmol), and NaOt-Bu (2.4 g, 24.6 mmol) were added to 82 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the product was extracted with ethyl acetate and separated by column chromatography to obtain compound H2-2 (6.0 g, yield: 69%).

[0227]

[0228]

[0229] Example 20: Preparation of compound H2-11

[0230]

[0231] Synthesis of Compounds 2-3

[0232] 1-Bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), and Na2CO3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the product was cooled to room temperature, the organic layer was extracted with ethyl acetate, and residual water was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compounds 2-3 (9 g, yield: 96%).

[0233] Synthesis of compound H2-11

[0234] Compounds 2-3 (3.0 g, 12.3 mmol), compound A (8 g, 18.5 mmol), Cu powder (0.39 g, 6.15 mmol), and K₂CO₃ (3.4 g, 24.6 mmol) were added to 60 mL of dichlorobenzene (DCB) in a flask, and the mixture was stirred under reflux for 24 hours. After the reaction was complete, the reaction product was cooled to room temperature, and MeOH was added to it while stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H₂-11 (1.1 g, yield: 14.8%).

[0235] MW Melting point H2-11 600.23 226.9℃

[0236] The luminous efficiency and lifetime characteristics of the OLED according to this disclosure will be explained in detail below. However, the following examples only illustrate the characteristics of the OLED according to this disclosure, and this disclosure is not limited to these examples.

[0237] Apparatus Examples 1-1 to 1-3: Production of a co-deposited first host compound and second host compound according to the present disclosure OLED of objects

[0238] The OLED according to this disclosure is manufactured as follows: A transparent electrode indium tin oxide (ITO) thin film (10Q / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used for the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is mounted on a substrate support of a vacuum vapor deposition apparatus. Compound HI-1, shown in Table 3 below, is introduced as a first hole injection compound into a chamber of the vacuum vapor deposition apparatus, and compound HT-1, shown in Table 3 below, is introduced as a first hole transport compound into another chamber of the same vacuum vapor deposition apparatus. The two materials are evaporated at different rates, and a first hole injection compound doping amount of 3 wt% based on the total amount of the first hole injection compound and the first hole transport compound is deposited to form a first hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 (as a first hole transport layer with a thickness of 80 nm) is deposited on the first hole injection layer. Compound HT-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was 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 the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: the first host compound and the second host compound shown in Table 1 were introduced as hosts into two chambers of the vacuum vapor deposition apparatus, respectively, and compound D-39 was introduced as a dopant into another chamber. The two host materials were evaporated at a 1:1 ratio, while the dopant material was evaporated at a different rate, thereby depositing a doping amount of 3 wt% based on the total amount of host and dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ET-1 and EI-1 were deposited as electron transport materials at a 50:50 weight ratio on the light-emitting layer to form an electron transport layer with a thickness of 35 nm. After depositing compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum phase deposition apparatus. This produced an OLED. All materials used in the production of the OLED were [processed / conducted / etc.]. -6 Purification is achieved through vacuum sublimation.

[0239] Comparative Examples 1-1 to 1-3: Production of OLEDs Containing Comparative Compounds as the Main Body

[0240] The OLED is produced in the same manner as in Device Example 1-1, except that only the second host compound shown in Table 1 below is used as the host of the light-emitting layer.

[0241] Comparative Examples 1-4: Production of OLEDs Containing Comparative Compounds as the Main Body

[0242] The OLED is produced in the same manner as in Device Example 1-1, except that the first host compound and the second host compound shown in Table 1 below are used as the host of the light-emitting layer, respectively.

[0243] Table 1 below shows the driving voltage, luminous efficiency, and emission color of the OLEDs produced in Device Examples 1-1 to 1-3 and Comparative Examples 1-1 and 1-4 at a brightness of 1,000 nits, as well as the time (T95) taken to reduce the brightness from 100% initial brightness to 95% brightness at a brightness of 5,500 nits.

[0244] [Table 1]

[0245]

[0246] As can be seen from Table 1 above, compared with conventional organic electroluminescent devices, organic electroluminescent devices containing a specific combination of compounds disclosed herein as the host material have significantly reduced driving voltage and significantly improved luminous efficiency and lifetime characteristics.

[0247] Apparatus Examples 2-1 to 2-3: Production of OLEDs according to this disclosure

[0248] Except for the formation of the light-emitting layer as described below, the OLED is produced in the same manner as in Device Example 1-1: the compound shown in Table 2 below is introduced as a host into a chamber of the vacuum phase deposition apparatus, and compound D-39 is introduced as a dopant into another chamber of the same vacuum phase deposition apparatus. The two materials are evaporated at different rates and deposited with a dopant 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.

[0249] Comparative Example 2-1: Production of OLEDs Containing Comparative Compounds

[0250] The OLED was produced in the same manner as in device example 2-1, except that compound A-1, shown in Table 3 below, was used as the host of the light-emitting layer.

[0251] Table 2 below shows the time (T95) taken for the OLEDs produced in Device Examples 2-1 to 2-3 and Comparative Example 2-1 to decrease from 100% initial brightness to 95% brightness at a brightness of 5,500 nits.

[0252] [Table 2]

[0253]

[0254] As can be seen from Table 2 above, organic electroluminescent devices containing compounds according to this disclosure as the host material have a longer lifespan compared to conventional organic electroluminescent devices.

[0255] The compounds used in the apparatus examples and comparative examples are shown in Table 3 below.

[0256] [Table 3]

[0257]

Claims

1. A plurality of host materials comprising a first host material and a second host material, the first host material comprising a compound represented by any one of the following Formulae 1-1 and 1-2, the second host material comprising a compound represented by the following Formula 2: wherein, Y represents NRa; Ra represents -L2-Ar2; Ar1 and Ar2 each independently represent a deuterium-substituted or unsubstituted (C6-C30)aryl; a deuterium-substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one kind of oxygen and sulfur; L1 and L2 each independently represent a single bond, a deuterium-substituted or unsubstituted (C6-C30)arylene; and HAr represents a triazinyl substituted with a deuterium-substituted or unsubstituted (C6-C30)aryl; wherein the (C6-C30)aryl is selected from phenyl, biphenyl, terphenyl, and naphthyl; wherein, L3 represents unsubstituted or substituted naphthylene, or unsubstituted or substituted biphenylene; and R1 to R8 each independently represent hydrogen, deuterium, or phenyl unsubstituted or substituted with at least one deuterium. --- (1-1) --- (1-2) Ar1 represents a deuterium-substituted or unsubstituted phenyl, a deuterium-substituted or unsubstituted naphthyl, a deuterium-substituted or unsubstituted biphenyl, a deuterium-substituted or unsubstituted terphenyl, a deuterium-substituted or unsubstituted benzofuropyrimidinyl, a deuterium-substituted or unsubstituted dibenzothiophenyl, a deuterium-substituted or unsubstituted benzothiophenyl, a deuterium-substituted or unsubstituted dibenzofuranyl, a deuterium-substituted or unsubstituted benzofuranyl, a deuterium-substituted or unsubstituted fluorenyl, a deuterium-substituted or unsubstituted benzofluorenyl, a deuterium-substituted or unsubstituted spirobifluorenyl, a deuterium-substituted or unsubstituted benzophenanthryl, a deuterium-substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl. The Formula 2 is represented by the following Formula 3: wherein, R1, R4, R5, and R8 each independently represent hydrogen, deuterium, or phenyl unsubstituted or substituted with at least one deuterium; and R2, R3, R6, and R7 each independently represent hydrogen or deuterium. The compound represented by any one of Formulae 1-1 and 1-2 is at least one selected from the following compounds: The compound represented by Formula 2 is at least one selected from the following compounds: At least one of the light-emitting layers comprises the plurality of host materials according to claim 1. R 11 to R 14 each independently represent hydrogen or deuterium; and a and d each independently represent an integer of 1 to 6; and b and c each independently represent an integer of 1 to 4, wherein if a to d are each independently an integer of 2 or more, each R 11 , each R 12 , each R 13 , and each R 14 may be the same or different; ----- (2) ​ ​ ​ ​ 2. The plurality of host materials according to claim 1, wherein, ​ 3. The plurality of host materials of claim 1, wherein, ​ --- (3) ​ Ar 21 and Ar 22 each independently represents phenyl which is unsubstituted or substituted by one or more deuterium, biphenyl which is unsubstituted or substituted by one or more deuterium, terphenyl which is unsubstituted or substituted by one or more deuterium, or naphthyl which is unsubstituted or substituted by one or more deuterium; L 21 represents naphthylene, which is unsubstituted or substituted by one or more deuterium, or biphenylene, which is unsubstituted or substituted by one or more deuterium; ​ ​ provided that if Ar 21 and Ar 22 both represent phenyl, then at least one of R1, R4, R5, and R8 is other than hydrogen or deuterium.

4. The plurality of host materials of claim 1, wherein, ​ and .

5. The plurality of host materials of claim 1, wherein, ​ 。 6. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein, ​

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