CN111868210A - Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same - Google Patents

Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same Download PDF

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CN111868210A
CN111868210A CN201980018976.2A CN201980018976A CN111868210A CN 111868210 A CN111868210 A CN 111868210A CN 201980018976 A CN201980018976 A CN 201980018976A CN 111868210 A CN111868210 A CN 111868210A
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金宾瑞
赵相熙
李孝姃
姜炫周
梁正恩
李琇炫
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

The present disclosure relates to a composition material for an organic electroluminescent device, various host materials, and an organic electroluminescent device including the same. By including the composition material for an organic electroluminescent device comprising a specific combination of compounds, an organic electroluminescent device having characteristics of high luminous efficiency and/or long life can be produced.

Description

Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same
Technical Field
The present disclosure relates to a composition material for an organic electroluminescent device, various host materials, and an organic electroluminescent device including the same.
Background
Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al, Eastman Kodak, Inc. (Eastman Kodak) in 1987 by using a TPD/ALq3 bilayer consisting 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. At present, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. For displays that are used for a long time and have high resolution, OLEDs having characteristics of high luminous efficiency and/or long lifetime are required.
Us patent No. 6,902,831 discloses azulene derivatives as organic electroluminescent compounds, and korean patent application laid-open nos. 2016-0022784 and 2017-0001563 disclose an organic electroluminescent device comprising carbazole derivatives and compounds having a carbazole-carbazole structure as a plurality of host compounds. However, there is still a need to develop a method for improving the performance of the organic electroluminescent device.
Disclosure of Invention
Technical problem
An object of the present disclosure is to provide an organic electroluminescent device having characteristics of high luminous efficiency and/or long life by including a composition material for an organic electroluminescent compound comprising a specific combination of compounds.
Solution to the problem
The present inventors found that the above object can be achieved by a composition material for an organic electroluminescent device comprising a compound represented by the following formula 1 and a compound represented by the following formula 2:
Figure BDA0002679632870000021
wherein
M represents N-L- (Ar)aS or O;
l represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
ar 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 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;
Y1To Y12Each independently represents N or CR1
R1Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or adjacent R1May be fused to each other to form a substituted or unsubstituted ring; and is
a represents an integer of 1 to 4, wherein if a is an integer of 2 or more, each Ar may be the same or different;
Figure BDA0002679632870000031
wherein
Ar1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
X1To X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Condensed to form a ring, provided that X1To X8Is not a substituted or unsubstituted carbazolyl group; and is
R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
The invention has the advantages of
By using the composition material for an organic electroluminescent device according to the present disclosure, an organic electroluminescent device having characteristics of high luminous efficiency and/or long life can be produced.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.
The term "composition material for an organic electroluminescent device" in the present disclosure means that at least two materials that can be used for an organic electroluminescent device are present together or are ready to be present together. Herein, "present together" means not only that at least two materials are mixed but also that at least two materials are separated from each other. Further, the composition material for the organic electroluminescent device is a concept covering a material included before (e.g., before vapor deposition) in the organic electroluminescent device and a material included after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the composition material for an organic electroluminescent device may include at least two of a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (host material and/or dopant material), an electron buffering material, a hole blocking material, an electron transport material, and an electron injection material. The composition material for the organic electroluminescent device may include at least two hole injection materials, at least two hole transport materials, at least two hole assist materials, at least two light emission assist materials, at least two electron blocking materials, at least two light emitting materials (host materials and/or dopant materials), at least two electron buffering materials, at least two hole blocking materials, at least two electron transport materials, and/or at least two electron transport materials. The composition material for an organic electroluminescent device of the present disclosure may be contained in any layer constituting the organic electroluminescent device. The at least two materials contained in the composition material may be contained together in one layer or may be contained in different layers, respectively. When at least two materials are contained in one layer, they may be mixedly evaporated to form a layer, or may be separately co-evaporated at the same time to form a layer.
The term "plurality of host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material contained before (e.g., before vapor deposition) in the organic electroluminescent device and a material contained after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the various host materials of the present disclosure may be a combination of at least two host materials, and optionally may further include conventional materials included in the organic electroluminescent material. At least two compounds included in the various host materials of the present disclosure may be included together in one light emitting layer or may be included in different light emitting layers, respectively, by a method known in the art. For example, the at least two compounds may be evaporated in mixture or co-evaporated, or may be evaporated individually.
As used herein, "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "(3-to 7-membered) heterocycloalkyl" means a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably selected from the group consisting of O, S, and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, and the like. "(C6-C30) (arylene) group" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, wherein the number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, phenanthrenyl, anthryl, indenyl, triphenylenyl, pyrenyl, and phenanthrenyl,
Figure BDA0002679632870000051
Naphthyl, naphthyl,Fluoranthenyl, spirobifluorenyl, azulenyl and the like. More specifically, the above-mentioned aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthonaphthyl, pyrenyl, 1-
Figure BDA0002679632870000052
Base 2-
Figure BDA0002679632870000053
Base 3-
Figure BDA0002679632870000054
Base, 4-
Figure BDA0002679632870000055
Base 5-
Figure BDA0002679632870000056
Base 6-
Figure BDA0002679632870000057
Radical, benzo [ c]Phenanthryl, benzo [ g ]]
Figure BDA0002679632870000058
A group, a 1-triphenylene group, a 2-triphenylene group, a 3-triphenylene group, a 4-triphenylene group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 9-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, an o-terphenyl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-quaterphenyl group, a 3-fluoranthyl group, a 4-fluoranthyl group, an 8-fluoranthyl group, a 9-fluoranthyl group, a benzofluoranthyl group, an o, 3, 4-xylyl group, 2, 5-xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-tert-butylphenyl group, p- (2-phenylpropyl) phenyl group, 4 '-methylbiphenyl group, 4' -tert-butyl-p-terphenyl-4-yl group, 9-dimethyl-1-fluorenyl group, 9-dimethyl-2-fluorenyl group, 9-dimethyl-3-fluorenyl group, 9-dimethyl-4-fluorenyl group, 9-diphenylbiphenyl-4-yl group A group of 1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl and the like. "(3-to 50-membered) (arylene) heteroaryl" means an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si and P, and 3 to 50 ring backbone atoms; wherein the number of ring backbone atoms is preferably from 3 to 30, more preferably from 5 to 20; and may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a (arylene) heteroaryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and include monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused-ring heteroaryl groups including benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzonaphthothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, quinoxalinyl, phenanthridinyl, benzodioxolyl and the like. More specifically, the above-mentioned heteroaryl group may 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, and the like, 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 A group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuryl group, 3-benzofuryl group, 4-benzofuryl group, 5-benzofuryl group, 6-benzofuryl group, 7-benzofuryl group, 1-isobenzofuryl group, 3-isobenzofuryl group, 4-isobenzofuryl group, 5-isobenzofuryl group, 6-isobenzofuryl group, 7-isobenzofuryl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 3-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 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-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 2-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzothiophenyl, and 4-dibenzo, 4-dibenzothiophenyl, 1-silafluorenyl (1-silafluoryl group), 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl group, 2-germanofluorenyl, 3-germanofluorenyl, and 4-germanofluorenyl. "halogen" includes F, Cl, Br, and I.
Further, "ortho (o-)", "meta (m-)" and "para (p-)" are prefixes, and respectively indicate the relative positions of substituents. The ortho position means that two substituents are adjacent to each other, and for example when two substituents in a benzene derivative occupy positions 1 and 2, it is referred to as ortho position. Meta indicates that the two substituents are at positions 1 and 3, and is referred to as meta, for example, when the two substituents in the benzene derivative occupy positions 1 and 3. Para represents the two substituents at positions 1 and 4, and is referred to as para, for example, when the two substituents in the benzene derivative occupy positions 1 and 4.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., substituent). Ar, L, R1To R9、R16、A1、L1And X1To X8The substituents of substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (arylene) heteroaryl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono-or di-alkylamino, substituted mono-or di-arylamino, and substituted alkylarylamino in (a) are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 50-membered) heteroaryl unsubstituted or substituted by (C1-C30) alkyl, (C6-C30) aryl and/or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3-to 50-membered) heteroaryl and/or tris (C6-C30) arylsilyl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6- C30) An arylamino group; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (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: (C1-C20) alkyl; (C6-C25) aryl unsubstituted or substituted with (C1-C20) alkyl and/or (3-to 30-membered) heteroaryl; (3-to 40-membered) heteroaryl and di (C6-C20) arylamino, unsubstituted or substituted with (C1-C20) aryl and/or (C6-C25) aryl. For example, the substituent may be methyl; a tertiary butyl group; phenyl which is unsubstituted or substituted by pyridyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl and/or dibenzothiophenyl; naphthyl unsubstituted or substituted by diphenyltriazinyl; a biphenyl group; a naphthyl phenyl group; a terphenyl group; a dimethyl fluorenyl group; a phenyl fluorenyl group; a diphenylfluorenyl group; phenanthryl; benzophenanthryl; a pyridyl group; triazinyl substituted with at least one of phenyl and naphthyl; indolyl substituted by diphenyl; benzimidazole substituted with phenyl; a quinolyl group; quinazolinyl substituted with phenyl and/or biphenyl; a quinoxalinyl group substituted with a phenyl group; carbazolyl, unsubstituted or substituted with phenyl; a dibenzofuranyl group; a dibenzothienyl group; benzocarbazolyl, unsubstituted or substituted with phenyl; a dibenzocarbazolyl group; benzophenanthrothiophenyl; a diphenylamino group; dimethylfluorenylphenylamino; or a substituted or unsubstituted (16-to 33-membered) heteroaryl group containing at least one of nitrogen, oxygen, or sulfur.
In the formulae of the present disclosure, if adjacent substituents are connected or fused to each other to form a substituted or unsubstituted (3-to 30-membered) ring, the ring may be a monocyclic or polycyclic, alicyclic or aromatic ring, or a combination thereof, wherein the ring may contain at least one heteroatom selected from nitrogen, oxygen and sulfur. For example, the 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.
In the formulae of the present disclosure, the (arylene) groups 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-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.
In the above formula 1, M represents N-L- (Ar)aS or O.
In formula 1 above, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5-to 18-membered) heteroarylene, wherein the heteroarylene may contain at least one of nitrogen, oxygen, and sulfur. According to an embodiment of the present disclosure, in formula 1, L may represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted benzoxazolinylene group, a substituted or unsubstituted benzothienopyrimidylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted (13-to 16-membered) heteroarylene group containing at least one of nitrogen, oxygen, and sulfur.
In formula 1 above, Ar 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 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, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-to 30-membered) heteroaryl, or a substituted or unsubstituted di (C6-C25) arylamino; and more preferably, a substituted or unsubstituted (C6-C18) aryl, a substituted or unsubstituted (5-to 25-membered) heteroaryl, or a substituted or unsubstituted di (C6-C18) arylamino.
According to an embodiment of the present disclosure, in formula 1, 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 triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl 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 quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl 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 benzothienopyrimidinyl group, a substituted or unsubstituted benzothienoquinolinyl group, a substituted or unsubstituted benzofuroquinolinyl group, a substituted or unsubstituted triindenyl (triaindenyl) group, a substituted or unsubstituted phenanthroimidazolyl group, a substituted or unsubstituted (9-to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted fluorenylphenylamino group, or a substituted or unsubstituted fluorenylbiphenylamino group.
In formula 1 above, a represents an integer of 1 to 4, preferably 1 or 2. If a is an integer of 2 or more, each Ar may be the same or different.
In the above formula 1, Y1To Y12Each independently represents N or CR1. According to an embodiment of the present disclosure, Y1To Y12All may represent CR1. According to another embodiment of the present disclosure, Y1To Y12May represent N.
In this context, R1Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or adjacent R1May be fused to each other to form a substituted or unsubstituted ring. Preferably, R 1Represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 25-membered) heteroaryl, or substituted or unsubstituted di (C6-C25) arylamino; or adjacent R1May be fused to each other to form a substituted or unsubstituted, mono-or polycyclic, (C3-C25) aromatic ring, wherein at least one carbon atom of the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. More preferably, R1Represents hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-to 18-membered) heteroaryl, or substituted or unsubstituted di (C6-C18) arylamino; or adjacent R1May be fused to each other to form a substituted or unsubstituted, mono-or polycyclic, (C5-C18) aromatic ring, wherein at least one carbon atom of the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. According to an embodiment of the present disclosure, R1May represent hydrogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenylbiphenylamino group, or the like.
According to an embodiment of the present disclosure, in formula 1, Y1To Y12At least one adjacent pair of (a) represents CR1And two adjacent CR1R of (A) to (B)1Are fused with each other to independently form a ring represented by any one of the following formulas 1-11 to 1-15, but are not limited thereto. In this context, Y1And Y2、R5And Y6And Y9And Y10Are also considered to be adjacent to each other. For example, the ring formed may be a substituted or unsubstituted benzene ring, a naphthalene ring, a furan ring, a thiophene ring, a substituted or unsubstituted pyrrole ring, a pyridine ring, a benzofuran ring, a benzothiophene ring, a substituted or unsubstituted indole ring, a dibenzofuran ring, a dibenzothiophene ring, a substituted or unsubstituted carbazole ring, or a phenanthrene ring, including rings represented by formulas 1-11 to 1-15.
Figure BDA0002679632870000111
In the above formulas 1-11 to 1-15,
Figure BDA0002679632870000112
adjacent CR of formula 11C and R in (1)1Fused ofA site.
In the above formulae 1-13 to 1-15, X represents N or CR4. According to embodiments of the present disclosure, all xs may be CR4. According to another embodiment of the present disclosure, at least one X may be N. R4Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; preferably, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-to 25-membered) heteroaryl; and more preferably, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-to 18-membered) heteroaryl.
In the above formulae 1 to 14, R3Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; preferably, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-to 25-membered) heteroaryl; and more preferably, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-to 18-membered) heteroaryl; for example, phenyl。
The compound represented by formula 1 may be represented by the following formula 1-1 or 1-2.
Figure BDA0002679632870000121
In the above formulas 1-1 and 1-2, M and Y2To Y12As defined in formula 1, and Y13And Y 14Each independently as for Y2As defined.
In the above formula 1-1, Y1Represents N or CR2Wherein R is2Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group.
In the above formula 2, A1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group; preferably an unsubstituted (C6-C25) aryl, or a (5-to 25-membered) heteroaryl unsubstituted or substituted with a (C6-C30) aryl; and more preferably an unsubstituted (C6-C18) aryl, or a (5-to 18-membered) heteroaryl unsubstituted or substituted with a (C6-C18) aryl. For example, A 1May represent a phenyl group; a naphthyl group; a biphenyl group; a terphenyl group; triazinyl substituted with at least one of phenyl, naphthyl and biphenyl; a diphenylpyridyl group; a phenyl quinoline; a phenyl quinoxaline; a phenylquinazoline; a diphenyl quinazoline; quinazolinyl substituted with phenylcarbazole; a dibenzofuranyl group; a dibenzothienyl group; or phenylcarbazolyl.
In the above formula 2, L1Represents a single bond, orSubstituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-to 30-membered) heteroarylene; preferably, a single bond, an unsubstituted (C6-C25) arylene, or an unsubstituted (5-to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5-to 18-membered) heteroarylene. For example, L1May represent a single bond, phenylene, naphthylene, biphenylene, quinolylene, quinoxalylene, quinazolinylene or carbazolyl.
In the above formula 2, X1To X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR 5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Fused to form a ring; preferably, hydrogen, unsubstituted (C6-C25) aryl, or unsubstituted (5-to 25-membered) heteroaryl; or may be adjacent to X1To X8Fused to form a ring; and more preferably, hydrogen, unsubstituted (C6-C18) aryl, or unsubstituted (5-to 18-membered) heteroaryl; or may be adjacent to X1To X8Fused to form a ring. However, X1To X8Is not a substituted or unsubstituted carbazolyl group. For example, X1To X8Each independently may represent hydrogen, phenyl, dibenzofuranyl or dibenzothiophenyl, or may be adjacent to X1To X8Fused to form a benzene ring, a substituted indole ring, a benzothiophene ring, a benzofuran ring, a substituted benzindole ring, a naphthofuran ring, a naphthothiophene ring or an aza ring
Figure BDA0002679632870000131
And (4) a ring. The substituent of the substituted indole ring may be at least one selected from the group consisting of: unsubstituted or substituted phenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinylPhenyl substituted with dibenzofuranyl and/or dibenzothiophenyl; unsubstituted naphthylphenyl; an unsubstituted biphenyl group; unsubstituted terphenyl; a quinoxalinyl group substituted with a phenyl group; a quinazolinyl group substituted with a phenyl group; and naphthyl substituted by diphenyltriazinyl. The substituent of the substituted benzindole ring may be at least one selected from the group consisting of: phenyl unsubstituted or substituted by benzofuranyl or dibenzothiophenyl; a naphthyl phenyl group; a biphenyl group; and a dibenzofuranyl group.
In the above formula 2, R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
The compound represented by formula 2 may be represented by any one of the following formulae 2-1 to 2-8.
Figure BDA0002679632870000141
In the above formulae 2-1 to 2-8, A1、L1And X1To X4As defined in formula 2; x9To X38Each independently as for X1Defining; b. e, f, g, h and l each independently represent 1 or 2; c. d and i each independently represent an integer of 1 to 3; j and k each independently represent an integer of 1 to 4; wherein if b to l are integers of 2 or more, X9、X14、X19、X20、X21、X30、X31And X35To X38Each of which may be the same or different. In the above formula 2-2, Z represents O or S.
In the above formulae 2-1 and 2-4 to 2-6, V and W each independently represent a single bond, NR16O or S, provided that both V and W are not simultaneously single bonds and both V and W are not simultaneously NR16. According to an embodiment of the present disclosure, one of V and W may represent a single bond, and the other one represents NR 16O or S.
R16Represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; preferably, a (C6-C25) aryl group unsubstituted or substituted with a (3-to 30-membered) heteroaryl group, or a (5-to 25-membered) heteroaryl group unsubstituted or substituted with a (C6-C30) aryl group; and more preferably a (C6-C18) aryl group unsubstituted or substituted with a (5-to 25-membered) heteroaryl group, or a (5-to 18-membered) heteroaryl group unsubstituted or substituted with a (C6-C18) aryl group. For example, R16May represent phenyl which is unsubstituted or substituted by diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzothienyl and/or dibenzofuranyl; naphthyl substituted with diphenyltriazinyl; a biphenyl group; a terphenyl group; a naphthyl phenyl group; a quinazolinyl group substituted with a phenyl group; or a quinoxalinyl group substituted with a phenyl group.
In the above formulae 2-1 to 2-8, X1To X4And X9To X38Each independently preferably represents hydrogen or an unsubstituted (C6-C25) aryl group; or may be adjacent to X 1To X4And X9To X38Fused to form a ring; more preferably represents hydrogen or an unsubstituted (C6-C18) aryl group; or may be adjacent to X1To X4And X9To X38Fused to form a ring. For example, X1To X4And X9To X30May each independently represent hydrogen or phenyl; x31To X38May represent hydrogen; x1And X2、X3And X4And two adjacent X21Each independently may be fused to each other to form an indole ring substituted with a phenyl group, or an unsubstituted benzene ring.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
Figure BDA0002679632870000161
Figure BDA0002679632870000171
Figure BDA0002679632870000181
Figure BDA0002679632870000191
Figure BDA0002679632870000201
Figure BDA0002679632870000211
Figure BDA0002679632870000221
Figure BDA0002679632870000231
Figure BDA0002679632870000241
Figure BDA0002679632870000251
Figure BDA0002679632870000261
Figure BDA0002679632870000271
Figure BDA0002679632870000281
Figure BDA0002679632870000291
Figure BDA0002679632870000301
Figure BDA0002679632870000311
Figure BDA0002679632870000321
Figure BDA0002679632870000331
Figure BDA0002679632870000341
Figure BDA0002679632870000351
Figure BDA0002679632870000361
Figure BDA0002679632870000371
Figure BDA0002679632870000381
Figure BDA0002679632870000391
Figure BDA0002679632870000401
Figure BDA0002679632870000411
The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
Figure BDA0002679632870000412
Figure BDA0002679632870000421
Figure BDA0002679632870000431
Figure BDA0002679632870000441
The compound represented by formula 1 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared according to the following reaction scheme.
[ reaction scheme 1]
Figure BDA0002679632870000451
[ reaction scheme 2]
Figure BDA0002679632870000452
[ reaction scheme 3]
Figure BDA0002679632870000453
[ reaction scheme 4]
Figure BDA0002679632870000461
[ reaction scheme 5]
Figure BDA0002679632870000462
[ reaction scheme 6]
Figure BDA0002679632870000471
In schemes 1 to 6, L, Ar, Y1To Y12And a is as defined in formula 1.
The compounds represented by formula 2 of the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared by referring to korean patent application laid-open nos. 2015-0135109 (published 2015 at 12/2), 2015-0032447 (published 2015 at 3/26), 2016-0099471 (published 2016 at 8/22), and 2018-0012709 (published 2018 at 2/6), but is not limited thereto.
Meanwhile, the composition material for an organic electroluminescent device of the present disclosure may be various host materials, wherein the compound represented by formula 1 may be a first host material and the compound represented by formula 2 may be a second host material. The composition material for an organic electroluminescent device of the present disclosure may consist of only the first host material represented by formula 1 and the second host material represented by formula 2, or may further include conventional materials included in the host materials. The composition material for an organic electroluminescent device of the present disclosure may include the compound represented by formula 1 and the compound represented by formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70: 30. Further, the compound represented by formula 1 and the compound represented by formula 2 may be combined in amounts of a desired ratio by placing them in a shaker and then mixing them, dissolving them by placing them in a glass tube by heating, and then collecting the resultant, or by dissolving them in a solvent, or the like. According to an embodiment of the present disclosure, there is provided an organic electroluminescent material including a plurality of host materials of the present disclosure.
In addition, an organic electroluminescent device including the compound represented by formula 1 and the compound represented by formula 2 of the present disclosure may be provided. Specifically, the organic electroluminescent device of the present disclosure may include at least one light emitting layer between an anode and a cathode, wherein the light emitting layer may include a host and a dopant, and the host may include the composition material for an organic electroluminescent device of the present disclosure. The organic electroluminescent device of the present disclosure may include a compound represented by formula 1 as a first host material and a compound represented by formula 2 as a second host material.
Herein, the light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. According to an embodiment of the present disclosure, a doping concentration of the dopant compound may be less than 20 wt% with respect to the host compound in the light emitting layer.
The organic electroluminescent device of the present disclosure may further include at least one layer selected from the group consisting of: 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.
The dopant included in the organic electroluminescent device of the present disclosure is at least one phosphorescent dopant or fluorescent dopant, 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 be preferably selected from complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably from complex compounds of ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The dopant included in the organic electroluminescent device according to the present disclosure may include a compound represented by the following formula 101, but is not limited thereto.
Figure BDA0002679632870000481
In formula 101, L is selected from the following structures 1 to 3:
Figure BDA0002679632870000482
R100to R103Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be adjacent to R100To R103Linked to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline;
R104To R107Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be adjacent to R104To R107Linked to form a substituted or unsubstituted fused ring, such as a substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;
R201to R220Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkylUnsubstituted (C6-C30) aryl; or may be adjacent to R201To R220Linked to form a substituted or unsubstituted fused ring; and is
n represents an integer of 1 to 3.
Specifically, the dopant compound includes the following compounds, but is not limited thereto.
Figure BDA0002679632870000491
Figure BDA0002679632870000501
Figure BDA0002679632870000511
Figure BDA0002679632870000521
An organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode.
One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes a light emitting layer, and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist 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. Each layer may further be composed of a plurality of layers.
The first and second electrodes may be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-side emission type according to the kind of materials forming the first electrode and the second electrode. 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.
The organic layer may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
Further, in the organic electroluminescent device according to the present disclosure, the organic layer may further include at least one metal selected from the group consisting of: an organometallic of a metal of group 1, a metal of group 2, a transition metal of period 4, a transition metal of period 5, a lanthanide and a d-transition element of the periodic table, or at least one complex compound comprising said metals.
In addition, the organic electroluminescent device according to the present disclosure may emit white light by further including at least one light emitting layer including a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound known in the art in addition to the compound according to the present disclosure. In addition, it may further include a yellow or orange light emitting layer, if necessary.
In the organic electroluminescent device according to the present disclosure, at least one layer (hereinafter, "surface layer") is preferably placed on one or more inner surfaces of one or both electrodes; selected from the group consisting of chalcogenide layers, metal halide layers, and metal oxide layers. In particular, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide comprises SiOX(1≤X≤2)、AlOX(X is more than or equal to 1 and less than or equal to 1.5), SiON, SiAlON and the like; the metal halide comprises LiF, MgF2、CaF2Rare earth metal fluorides, etc.; and the metal oxide comprises Cs 2O、Li2O, MgO, SrO, BaO, CaO, etc.
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 a multilayer to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. The hole transport layer or the electron blocking layer may also be a multilayer.
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 a multi-layer to control injection of electrons and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds at the same time. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein each of the multiple layers may use multiple compounds.
The light emission assisting layer may be disposed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When a light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used to facilitate hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to facilitate electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and the hole transport rate (or the hole injection rate) may be effectively promoted or blocked, thereby enabling control of charge balance. In addition, an electron blocking layer may be disposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layers further included may serve as a hole assist layer or an electron blocking layer. The hole assist layer and the electron blocking layer may have an effect of improving the efficiency and/or lifetime of the organic electroluminescent device.
In the organic electroluminescent device according to the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the light emitting medium. Further, the hole-transporting compound is oxidized into cations, and thus it becomes easier to inject and transport holes from the mixed region to the light-emitting medium. Preferably, the oxidizing dopant includes various lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers emitting white light.
The organic electroluminescent material according to the embodiments of the present disclosure may be used as a light emitting material for a white organic light emitting device. According to the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light emitting cells, a white organic light emitting device has been proposed to have various structures, such as a parallel arrangement (side-by-side) method, a stacking method, or a Color Conversion Material (CCM) method, etc. In addition, the organic electroluminescent material according to the embodiments of the present disclosure may also be applied to an organic electroluminescent device including QDs (quantum dots).
In order to form each layer constituting the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, or the like may be used.
When a wet film-forming method is used, a thin film is formed by dissolving or dispersing the material constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvent having no problem in film-forming ability.
The present disclosure may provide a display device using a composition material for an organic electroluminescent device including a compound represented by formula 1 and a compound represented by formula 2. That is, the composition material for an organic electroluminescent device of the present disclosure may be used to produce a display system or a lighting system. Specifically, a display system, such as a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using the composition material for an organic electroluminescent device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, the luminous efficiency and lifetime characteristics of the OLED device improved by including the composition material for an organic electroluminescent device of the present disclosure will be explained. However, the following examples are intended to explain the features of the OLED device including the composition material for an organic electroluminescent device of the present disclosure, and the present disclosure is not limited to the following examples.
Device examples 1 to 18: production of OLED devices comprising the composition materials for OLED devices according to the present disclosure Product produced by birth
Producing an Organic Light Emitting Diode (OLED) device comprising the composition material for an OLED device according to the present disclosure. A transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomantec, Japan) on a glass substrate for an OLED device was sequentially ultrasonically washed with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of the vacuum vapor deposition apparatus. Introducing a compound HI-1 into a chamber of the vacuum vapor deposition apparatus, and then controlling the pressure inside the chamber of the apparatus to 10-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate. Then, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. A compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a first hole transport layer having a thickness of 10nm on the second hole injection layer. Introducing a compound HT-2 into another chamber of the vacuum vapor deposition apparatus and evaporating the compound by applying an electric current to the chamber, Thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After the hole injection layer and the hole transport layer are formed, a light emitting layer is then deposited as follows. The first and second host compounds shown in table 1 below were introduced as hosts into one cell of the vacuum vapor deposition apparatus, and compound D-39 was introduced into the other cell. Two host materials were evaporated at a rate of 1:1, and a dopant material was simultaneously evaporated at different rates, and these were 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 having a thickness of 40nm on the second hole transporting layer. The compound ET-1 and the compound EI-1 were then introduced into two additional cells, evaporated at a rate of 1:1, and deposited to form an electron transport layer having a thickness of 35nm on the light-emitting layer. Next, after depositing the compound EI-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED device was produced.
Comparative example 1: production of OLED devices comprising conventional Compounds
An OLED device was produced in the same manner as in device example 1, except that compound a was used as the second host compound.
The luminous efficiency of the produced OLED device at a luminance of 5,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a constant current and at a luminance of 5,000 nits (lifetime; T95) are provided in table 1 below.
[ Table 1]
Figure BDA0002679632870000571
From table 1 above, it can be seen that the organic electroluminescent device comprising the compounds represented by formulae 1 and 2 of the present disclosure as a host exhibits higher luminous efficiency and longer life characteristics as compared to the organic electroluminescent device comprising the conventional organic electroluminescent compound. By using the composition material for an organic electroluminescent device of the present disclosure, both of the luminous efficiency and the lifetime characteristics in the organic electroluminescent device, which conflict with each other, can be improved.
The compounds used in the apparatus examples and comparative examples are shown in table 2 below.
[ Table 2]
Figure BDA0002679632870000581
Figure BDA0002679632870000591

Claims (10)

1. A composition material for an organic electroluminescent device, the composition material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2:
Figure FDA0002679632860000011
wherein
M represents N-L- (Ar)aS or O;
l represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar 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 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;
Y1to Y12Each independently represents N or CR1
R1Represents 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 tri (C1-C30) alkylsilyl, substituted or unsubstitutedSubstituted 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, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or adjacent R 1May be fused to each other to form a substituted or unsubstituted ring; and is
a represents an integer of 1 to 4, wherein if a is an integer of 2 or more, each Ar may be the same or different;
Figure FDA0002679632860000021
wherein
Ar1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
X1to X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Condensed to form a ring, provided that X1To X8Is not a substituted or unsubstituted carbazolyl group; and is
R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
2. The composition material for an organic electroluminescent device according to claim 1, wherein formula 1 is represented by the following formula 1-1 or 1-2:
Figure FDA0002679632860000022
wherein the content of the first and second substances,
m and Y2To Y12As defined in claim 1;
Y13and Y14Each independently as for Y2Defining; and is
Y1Represents N or CR2Wherein R is2Represents 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 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, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group.
3. The composition material for organic electroluminescent device according to claim 1, wherein, in formula 1, Y is 1To Y12At least one adjacent pair of (a) represents CR1And two adjacent CR1R of (A) to (B)1Fused with each other to independently form a ring represented by any one of the following formulas 1-11 to 1-15:
Figure FDA0002679632860000031
wherein the content of the first and second substances,
x represents N or CR4
R3And R4Each independently 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 tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di (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, substituted or unsubstituted mono-C6-C30) arylamino, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; and is
Figure FDA0002679632860000032
Indicates adjacent CR1C and R in (1)1The fused site of (a).
4. The composition material for organic electroluminescent device according to claim 1, wherein Ar represents 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 triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl 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 quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl 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 benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted benzothienoquinolinyl group, a substituted or unsubstituted benzofuroquinolinyl group, a substituted or unsubstituted triindenyl group, a substituted or unsubstituted phenanthroimidazolyl group, a substituted or unsubstituted (9-to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenyldiphenylamino group, or a substituted or unsubstituted fluorenylphenylamino group.
5. The composition material for an organic electroluminescent device according to claim 1, wherein formula 2 is represented by any one of the following formulae 2-1 to 2-8:
Figure FDA0002679632860000041
Figure FDA0002679632860000051
wherein the content of the first and second substances,
A1、L1and X1To X4As defined in claim 1;
X9to X38Each independently as for X1Defining;
b. e, f, g, h and l each independently represent 1 or 2; c. d and i each independently represent an integer of 1 to 3; j and k each independently represent an integer of 1 to 4; wherein if b to l are integers of 2 or more, X9、X14、X19、X20、X21、X30、X31And X35To X38Each of which may be the same or different;
z represents O or S;
v and W each independently represent a single bond, NR16O or S, provided that both V and W are not simultaneously single bonds and both V and W are not simultaneously NR16(ii) a And areAnd is
R16Represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl.
6. The composition material for organic electroluminescent device according to claim 1, wherein Ar, L, R 1、A1、L1、X1To X8And R5To R9The substituents of substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (arylene) heteroaryl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono-or di-alkylamino, substituted mono-or di-arylamino, and substituted alkylarylamino in (a) are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 50-membered) heteroaryl unsubstituted or substituted with (C1-C30) alkyl, (C6-C30) aryl or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3-to 50-membered) heteroaryl or tri (C6-C30) arylsilyl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; 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; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronocarbonyl A group; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
7. The composition material for organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
Figure FDA0002679632860000071
Figure FDA0002679632860000081
Figure FDA0002679632860000091
Figure FDA0002679632860000101
Figure FDA0002679632860000111
Figure FDA0002679632860000121
Figure FDA0002679632860000131
Figure FDA0002679632860000141
Figure FDA0002679632860000151
Figure FDA0002679632860000161
Figure FDA0002679632860000171
Figure FDA0002679632860000181
Figure FDA0002679632860000191
Figure FDA0002679632860000201
Figure FDA0002679632860000211
Figure FDA0002679632860000221
Figure FDA0002679632860000231
Figure FDA0002679632860000241
Figure FDA0002679632860000251
Figure FDA0002679632860000261
Figure FDA0002679632860000271
Figure FDA0002679632860000281
Figure FDA0002679632860000291
Figure FDA0002679632860000301
Figure FDA0002679632860000311
Figure FDA0002679632860000321
8. the composition material for organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
Figure FDA0002679632860000322
Figure FDA0002679632860000331
Figure FDA0002679632860000341
Figure FDA0002679632860000351
Figure FDA0002679632860000361
9. a plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises the compound represented by formula 1 according to claim 1, and the second host material comprises the compound represented by formula 2 according to claim 1.
10. An organic electroluminescent device comprising the composition material for organic electroluminescent device as claimed in claim 1.
CN201980018976.2A 2018-03-16 2019-03-15 Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same Pending CN111868210A (en)

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