CN113582856A - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDF

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CN113582856A
CN113582856A CN202110960033.0A CN202110960033A CN113582856A CN 113582856 A CN113582856 A CN 113582856A CN 202110960033 A CN202110960033 A CN 202110960033A CN 113582856 A CN113582856 A CN 113582856A
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organic electroluminescent
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K-J·李
C-S·金
H-C·安
S-J·杨
D-H·文
J-S·俊
Y－J·曹
T-J·李
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

The present application relates to organic electroluminescent compounds and organic electroluminescent devices comprising the same. The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compounds according to the present invention, organic electroluminescent devices exhibiting excellent luminous efficiency (e.g., current efficiency) can be provided.

Description

Organic electroluminescent compounds and organic electroluminescent device comprising the same
The application is a divisional application of an invention patent application with the international application number of PCT/KR2014/011968, the international application date of 5.12.2014, the application number of 201480063491.2 entering the national phase of China, and the invention name of 'an organic electroluminescent compound and an organic electroluminescent device containing the compound'.
Technical Field
The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
Background
An Electroluminescent (EL) device is a self-luminous device, which is advantageous in that it provides a wide viewing angle, a large contrast ratio, and a fast response time. Organic EL devices were originally developed by Eastman Kodak (Eastman Kodak) by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [ appl. phys. lett. 51,913,1987 ].
The most important factor determining the light emitting efficiency in the organic EL device is a light emitting material. Heretofore, fluorescent materials have been widely used as light emitting materials. However, in view of the mechanism of electroluminescence, since phosphorescent materials theoretically enhance the luminous efficiency four (4) times as compared to fluorescent materials, phosphorescent light-emitting materials have been widely studied. Iridium (III) complexes have been widely referred to as phosphorescent materials, including bis (2- (2 '-benzothienyl) -pyridinato-N, C-3') iridium (acetylacetonate) ((acac) ir (btp)2), tris (2-phenylpyridine) iridium (ir (ppy)3), and bis (4, 6-difluorophenylpyridinato-N, C2) iridium picolinate (Firpic) as red, green, and blue emitting materials, respectively.
Currently, 4,4'-N, N' -dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (japan) et al developed a highly efficient organic EL device using Bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) or the like as host materials, which are called hole blocking materials.
Although these materials provide good luminescent characteristics, they have the following disadvantages: (1) due to its lower glass transition temperature and poor thermal stability, it may degrade in vacuum during high temperature deposition processes, which results in poor lifetime. (2) The power efficiency of an organic EL device is given by [ (pi/voltage) × current efficiency ], and is inversely proportional to the voltage. Although organic EL devices including phosphorescent host materials provide higher current efficiency (cd/a) than organic EL devices including fluorescent materials, significantly high driving voltages are necessary. Therefore, there is no advantage in terms of power efficiency (lm/W). (3) In addition, the operating life of the organic EL device is short, and improvement in light emission efficiency is still required.
In order to improve efficiency and stability, the organic EL device may be fabricated with a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure, a compound for a hole transport layer is important to enhance device characteristics such as efficiency of transporting holes to a light emitting layer, light emitting efficiency, and lifetime.
In this regard, copper phthalocyanine (CuPc), 4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -diphenyl-N, N '-bis (3-methylphenyl) - (1,1' -biphenyl) -4,4 '-diamine (TPD), 4',4 ″ -tris (3-methylphenylphenylamino) triphenylamine (MTDATA), and the like are used as hole injection and transport materials for organic EL devices. However, organic EL devices using these materials are problematic in terms of quantum efficiency and service life. This is because, when the organic EL device is driven at a high current, thermal stress is generated between the anode and the hole injection layer. Thermal stresses significantly shorten the service life of the device. In addition, since the organic material used for the hole injection layer has extremely high hole mobility, the hole-electron charge balance can be broken and the quantum yield (cd/a) can be reduced.
Korean patent application laid-open nos. 10-2012-0029446, WO 2013-065589, and WO 2007-119800 disclose amine derivatives having a benzofluorene-based substituent as compounds for organic EL devices. However, the benzofluorene-based substituent of the reference is a benzo [ a ] fluorene-or benzo [ c ] fluorene-based substituent. Amine derivatives having benzo [ b ] fluorene-based substituents are not specifically disclosed in the reference.
Disclosure of Invention
Problems to be solved
It is an object of the present invention to provide organic electroluminescent compounds exhibiting luminous efficiency (e.g., current efficiency), and organic electroluminescent devices comprising the same.
Solution to the problem
The present inventors found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1.
Figure BDA0003221739530000021
Wherein
Ar1To Ar4Each independently represents a warpSubstituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; and Ar1And Ar2May be fused with each other to form a ring;
Ar5represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-to 30-membered) heteroaryl;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-to 30-membered) heteroarylene;
L2represents a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5-to 30-membered) heteroarylene group;
R1and R2Each independently represents hydrogen, deuterium, halogen, 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 (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N (R6-C30)11)(R12)、-Si(R13)(R14)(R15)、-S(R16)、-O(R17) Cyano, nitro or hydroxy; or may be linked to an adjacent substituent(s) to form a (3-to 30-membered) mono-or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
R11to R17Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3-to 30-membered) mono-or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
n and m each independently represent 0 or 1, with the proviso that n and m cannot both be 0;
a represents an integer of 1 to 3; wherein a is an integer of 2 or more, each R1May be the same or different;
b represents an integer of 1 to 6; wherein b is an integer of 2 or greater, each R2May be the same or different;
the heteroaryl (ene) group contains at least one heteroatom selected from B, N, O, S, P (═ O), Si and P; and
the heterocycloalkyl group contains at least one heteroatom selected from O, S and N.
Advantageous effects of the invention
The organic electroluminescent compounds according to the present invention can provide organic electroluminescent devices exhibiting excellent luminous efficiency (e.g., current efficiency).
Detailed Description
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.
The present invention provides the organic electroluminescent compounds of formula 1 above, organic electroluminescent materials comprising the organic electroluminescent compounds, and organic electroluminescent devices comprising the organic electroluminescent compounds.
The details of the organic electroluminescent compounds of formula 1 are as follows.
As used herein, "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. "alkenyl" includes ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. "alkynyl" includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. "(3-to 7-membered) heterocycloalkyl" indicates a cycloalkyl group having 3 to 7 ring backbone atoms, which includes at least one heteroatom selected from the group consisting of: B. n, O, S, P (═ O), Si and P, preferably O, S and N, and include tetrahydrofuran, pyrrolidine, thiacyclopentane, tetrahydropyran, and the like. Further, "(arylene) group" represents a single ring or a condensed ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylene, pyrenyl, tetracenyl, peryleneyl, chrysenyl, condensed tetraphenyl, fluoranthenyl, and the like. "(5-to 30-membered) (arylene) denotes an aryl group having 5 to 30 ring backbone atoms and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, P (═ O), Si, and P; a condensed ring which may be a single ring or condensed with at least one benzene ring; may be partially saturated; may be a group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via a single bond; and include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, bipyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, naphthofuryl, naphthothienyl, benzonaphthofuryl, benzonaphthothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, isoxazolyl, isoindolyl, indolyl, indolinyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, and the like, Phenoxazinyl, phenanthridinyl, benzodioxolyl, and the like. Further, "halogen" includes F, Cl, Br and I.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or group, i.e., a substituent. Ar of formula 11To Ar5、L1、L2、R1、R2And R11To R17Substituted alkyl (ene), substituted aryl (ene), substituted heteroaryl (ene), substituted cycloalkyl, substituted heterocycloalkylThe substituent of the group and the substituted arylalkyl group are each independently at least one selected from the group consisting of: deuterium; halogen; unsubstituted or halogen-substituted (C1-C30) alkyl; (C1-C30) alkoxy; (C6-C30) aryl; (3-to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl; (C3-C30) cycloalkyl; (3-to 7-membered) heterocycloalkyl; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; (C2-C30) alkenyl; (C2-C30) alkynyl; a cyano group; di (C1-C30) alkylamino; di (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) arylamino; a bis (C6-C30) arylboron group; a di (C1-C30) alkylboron group; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) aryl; a carboxyl group; a nitro group; and a hydroxyl group; and preferably each independently at least one selected from the group consisting of: (C1-C30) alkyl; (C6-C21) aryl; (5-to 21-membered) heteroaryl unsubstituted or substituted with (C6-C12) aryl; and a di (C6-C21) arylamino group.
According to one aspect of the present invention, the compound of formula 1 is represented by any one of the following formulae 2 to 4, and preferably the following formulae 2 or 3:
Figure BDA0003221739530000051
wherein Ar is1To Ar5、L1、L2、R1、R2A and b are as defined above in formula 1.
In formulae 1 to 4, Ar1To Ar4Each independently represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-to 30-membered) heteroaryl, and Ar1And Ar2May be fused with each other to form a ring. Preferably, Ar1To Ar4Each independently represents a substituted or unsubstituted (C6-C21) aryl group, or a substituted or unsubstituted (5-to 21-membered) heteroaryl group, and Ar1And Ar2May be fused to each other to form a ring; and further morePreferably, the substituent representing the substituted or unsubstituted (C6-C21) aryl group, the (C6-C21) aryl group may be at least one selected from the group consisting of: (C1-C30) alkyl, (C6-C21) aryl unsubstituted or substituted with (C1-C10) alkyl, and (5-to 21-membered) heteroaryl unsubstituted or substituted with (C6-C12) aryl, and Ar1And Ar2May be fused with each other to form a ring. Specifically, Ar1To Ar4May each independently represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl or benzofluorenyl, and Ar1And Ar2May be fused with each other to form a ring. Specifically, Ar1To Ar4The substituent(s) may be at least one selected from the group consisting of: (C1-C4) alkyl, phenyl, naphthyl, fluorenyl, 9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalyl, 9-phenylcarbazolyl, dibenzothienyl, and dibenzofuranyl.
Specifically, Ar1And Ar2The formed ring may be represented by the following formula 5:
Figure BDA0003221739530000061
wherein R is3And R4Each independently represents hydrogen, (C1-C30) alkyl, (C6-C30) aryl, or (3-to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl; and represents a connection to L1The location of (1).
In particular, R3And R4One of which represents hydrogen and the other may be selected from the group consisting of: (C1-C4) alkyl; a phenyl group; a biphenyl group; a naphthyl group; carbazolyl unsubstituted or substituted with phenyl, biphenyl or naphthyl; dibenzothienyl unsubstituted or substituted by phenyl, biphenyl or naphthyl; and dibenzofuranyl which is unsubstituted or substituted by phenyl, biphenyl or naphthyl.
Ar5Represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5 to 5)30-membered) heteroaryl. Preferably, Ar5Represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C21) aryl group or a substituted or unsubstituted (5-to 21-membered) heteroaryl group. More preferably, Ar5Represents an unsubstituted (C1-C10) alkyl group; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, a (6-to 21-membered) heteroaryl unsubstituted or substituted with (C6-C13) aryl, or di (C6-C18) arylamino; or a (6-to 21-membered) heteroaryl group which is unsubstituted or substituted by a (C1-C10) alkyl or (C6-C18) aryl group and which contains a heteroatom selected from N, O and S. Specifically, Ar5Represents (C1-C4) alkyl; phenyl, biphenyl, naphthyl, terphenyl, phenanthryl, anthracyl or fluorenyl, unsubstituted or substituted with (C1-C4) alkyl, phenyl, carbazolyl, diphenylpyrimidinyl, diphenyltriazinyl, phenylbenzimidazolyl, diphenylamino, (phenyl) (biphenyl) amino, di (biphenyl) amino or (phenyl) (naphthyl) amino; or carbazolyl, benzocarbazolyl, dibenzothienyl, benzonaphthothienyl, dibenzofuranyl or benzonaphthofuranyl, which is unsubstituted or substituted by phenyl.
L1Represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-to 30-membered) heteroarylene. Preferably, L1Represents a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-to 21-membered) heteroarylene. More preferably, L1Represents a single bond; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; or a (5-to 18-membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl group and containing nitrogen as a heteroatom. Specifically, L1Represents a single bond, phenyl or pyrimidinyl.
L2Represents a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group or a substituted or unsubstituted (5-to 30-membered) heteroarylene group. Preferably, L2Represents a substituted or unsubstituted (C1-C20) alkylene group, a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-to 21-membered) heteroarylene group. More preferably, L2Represents unsubstituted(C1-C10) alkylene; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; or a (6-to 21-membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl group and containing oxygen as a heteroatom. Specifically, L2Represents (C1-C4) alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9-dimethyl-9H-fluorenyl or dibenzofuranyl.
R1And R2Each independently represents hydrogen, deuterium, halogen, 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 (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N (R6-C30)11)(R12)、-Si(R13)(R14)(R15)、-S(R16)、-O(R17) Cyano, nitro or hydroxy, or may be linked to an adjacent substituent to form a (3-to 30-membered) mono-or polycyclic alicyclic or aromatic ring whose carbon atom may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur. R11To R17Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3-to 30-membered) mono-or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. Preferably, R1And R2Each independently represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-to 21-membered) heteroaryl, or-N (R)11)(R12). Preferably, R11And R12Each independently represents a substituted or unsubstituted (C6-C21) aryl group. More preferably, R1And R2Each independently represents hydrogen; unsubstituted (C6-C18) aryl; unsubstituted (6-to 18-membered) heteroaryl containing nitrogen as a heteroatom;or-N (R)11)(R12). More preferably, R11And R12Each independently represents an unsubstituted (C6-C18) aryl group. In particular, R1And R2Each independently represents hydrogen, phenyl, pyridyl, pyrimidinyl, carbazolyl, diphenylamino, (phenyl) (biphenyl) amino, di (biphenyl) amino, or (phenyl) (naphthyl) amino.
n and m each independently represent 0 or 1, with the proviso that n and m cannot both be 0.
a represents an integer of 1 to 3; wherein a is an integer of 2 or more, each R1May be the same or different. Preferably, a represents 1.
b represents an integer of 1 to 6; wherein b is an integer of 2 or greater, each R2May be the same or different. Preferably, b represents 1.
According to one embodiment of the present invention, in formulae 1 to 4, Ar1To Ar4Each independently represents a substituted or unsubstituted (C6-C21) aryl or a substituted or unsubstituted (5-to 21-membered) heteroaryl; and Ar1And Ar2May be fused to each other to form a ring; ar (Ar)5Represents a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C21) aryl or a substituted or unsubstituted (5-to 21-membered) heteroaryl; l is1Represents a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-to 21-membered) heteroarylene; l is2Represents a substituted or unsubstituted (C1-C20) alkylene group, a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-to 21-membered) heteroarylene group; r1To R2Each independently represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-to 21-membered) heteroaryl, or-N (R)11)(R12)；R11And R12Each independently represents a substituted or unsubstituted (C6-C21) aryl group; n and m each independently represent 0 or 1, with the proviso that n and m cannot both be 0; a represents an integer of 1 to 3; wherein a is an integer of 2 or more, each R1May be the same or different; b represents an integer of 1 to 6; wherein b is an integer2 or greater, each R2May be the same or different; and the heteroaryl (ene) group contains at least one heteroatom selected from N, O and S.
According to another embodiment of the present invention, in formulae 1 to 4, Ar1To Ar4Each independently represents a substituted or unsubstituted (C6-C21) aryl group, and the substituent of the (C6-C21) aryl group may be at least one selected from the group consisting of: (C1-C30) alkyl, (C6-C21) aryl unsubstituted or substituted with (C1-C10) alkyl, and (5-to 21-membered) heteroaryl unsubstituted or substituted with (C6-C12) aryl, and Ar1And Ar2May be fused with each other to form a ring; ar (Ar)5Represents unsubstituted (C1-C10) alkyl, (C6-C18) aryl unsubstituted or substituted by (C1-C10) alkyl, (C6-C21) aryl, (6-to 21-membered) heteroaryl unsubstituted or substituted by (C6-C13) aryl or di (C6-C18) arylamino, or (6-to 21-membered) heteroaryl unsubstituted or substituted by (C1-C10) alkyl or (C6-C18) aryl and containing a heteroatom selected from N, O and S; l is1Represents a single bond, (C6-C18) arylene which is unsubstituted or substituted by (C1-C10) alkyl, or (5-to 18-membered) heteroarylene which is unsubstituted or substituted by (C1-C10) alkyl and which contains nitrogen as a heteroatom; l is2Represents unsubstituted (C1-C10) alkylene, (C6-C18) arylene unsubstituted or substituted by (C1-C10) alkyl, or (6-to 21-membered) heteroarylene unsubstituted or substituted by (C1-C10) alkyl and containing oxygen as a heteroatom; r1And R2Each independently represents hydrogen, unsubstituted (C6-C18) aryl, unsubstituted (6-to 18-membered) heteroaryl containing nitrogen as a heteroatom, or-N (R)11)(R12)；R11And R12Each independently represents an unsubstituted (C6-C18) aryl group; n and m each independently represent 0 or 1, with the proviso that n and m cannot both be 0; a represents 1; and b represents 1.
More specifically, the organic electroluminescent compounds of formula 1 include (but are not limited to) the following:
Figure BDA0003221739530000091
Figure BDA0003221739530000101
Figure BDA0003221739530000111
Figure BDA0003221739530000121
the organic electroluminescent compounds according to the invention can be prepared by synthetic methods known to the person skilled in the art. For example, it can be prepared according to the following reaction scheme 1 or 2.
[ reaction scheme 1]
Figure BDA0003221739530000122
[ reaction scheme 2]
Figure BDA0003221739530000123
In addition, the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising the same.
The material may consist of the organic electroluminescent compounds according to the invention. In addition, the materials may further comprise, in addition to the compounds of the invention, conventional compounds which have been included in organic electroluminescent materials. Preferably, the organic electroluminescent material may be a host material or a hole transport material.
The organic electroluminescent device of the present invention may include a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. The organic layer may include at least one compound of formula 1.
One of the first and second electrodes may be an anode, and the other may be a cathode. The organic layer may include a light emitting layer, and further include at least one layer selected from a hole injection layer, a hole transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron buffer layer, and an electron blocking layer.
The organic electroluminescent compounds according to the present invention may be contained in at least one of the light-emitting layer and the hole transport layer. When used in a hole transporting layer, the organic electroluminescent compounds of the present invention may be contained therein as a hole transporting material. When used in the light-emitting layer, the organic electroluminescent compound of the present invention may be contained as a host material.
When the organic electroluminescent compound of the present invention is included as a hole transport material, the light-emitting layer may include a light-emitting material known in the art, or an organic electroluminescent compound of the present invention other than the compound of the present invention used as a hole transport material. The light emitting material known in the art may be a host material known in the art, and may further include at least one dopant. The host material known in the art may be a fluorescent or phosphorescent host material known in the art.
When the organic electroluminescent compound of the present invention is contained as a host material (first host material) in the light-emitting layer, at least one dopant may be further contained, and if necessary, another compound may be contained as a second host material. The weight ratio between the first host material and the second host material is in the range of 1:99 to 99: 1.
A compound selected from the group consisting of compounds of the following formulae 6 to 8 is preferable as a known host material or a second host material due to light emission efficiency.
H-(Cz-L4)h-M (6)
H-(Cz)i-L4-M (7)
Figure BDA0003221739530000131
Wherein Cz represents the following structure:
Figure BDA0003221739530000132
R21to R24Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, or R25R26R27Si-；R25To R27Each independently represents a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group; l is4Represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-to 30-membered) heteroarylene; m represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-to 30-membered) heteroaryl; y is1And Y2Each independently represents-O-, -S-, -N (R)31) -or-C (R)32)(R33) With the proviso that Y1And Y2Not exist at the same time; r31To R33Each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-to 30-membered) heteroaryl, R32And R33May be the same or different; h and i each independently represent an integer of 1 to 3; j. k, o and r each independently represent an integer of 0 to 4; and in the case where h, i, j, k, o or r is an integer of 2 or more, (Cz-L4) Each of (c), (c) each of (c), R21Each of R, R22Each of R, R23Each of (1) or R24Each of which may be the same or different.
Specifically, the host materials represented by formulas 6 to 8 include the following:
Figure BDA0003221739530000141
Figure BDA0003221739530000151
Figure BDA0003221739530000161
(wherein TPS represents a triphenylsilyl group.)
The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material used for the organic electroluminescent device of the present invention is not limited, but may be preferably selected from a metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt), more preferably an ortho-metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The phosphorescent dopant may be preferably selected from the group consisting of compounds represented by the following formulas 9 to 11.
Figure BDA0003221739530000162
Figure BDA0003221739530000171
Wherein L is selected from the following structures:
Figure BDA0003221739530000172
R100represents hydrogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C3-C30) cycloalkyl; r101To R109And R111To R123Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, cyano, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C1-C30) alkoxy; or R106To R109May be linked to an adjacent substituent to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzofuran; or R120To R123May be linked to an adjacent substituent to form a substituted or unsubstituted fused ring, such as a substituted or unsubstituted quinoline; r124To R127Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; r124To R127May be linked to an adjacent substituent to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzofuran; r201To R211Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl or substituted or unsubstituted (C6-C30) aryl, or R208To R211May be linked to an adjacent substituent to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzofuran; o and p each independently represent an integer of 1 to 3; wherein o or p is an integer of 2 or more, each R100May be the same or different; and d represents an integer of 1 to 3.
Specifically, phosphorescent dopant materials include the following:
Figure BDA0003221739530000173
Figure BDA0003221739530000181
Figure BDA0003221739530000191
Figure BDA0003221739530000201
according to other aspects of the present invention, there is provided a mixture or composition for preparing an organic electroluminescent device. The mixture or composition comprises a compound of the invention. The mixture or composition may be a mixture or composition for preparing a light emitting layer or a hole transport layer of an organic electroluminescent device. When the compound of the present invention is included in a mixture or composition for preparing a light-emitting layer of an organic electroluminescent device, the compound of the present invention may be included as a host material. When the compound of the present invention is included as a host material, the mixture or composition may further include a second host material, for example, those selected from the group consisting of compounds represented by formulas 6 to 8. When the compound of the present invention is included in a mixture or composition for preparing a hole transport layer of an organic electroluminescent device, the compound of the present invention may be included as a hole transport material.
The organic electroluminescent device of the present invention may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, wherein the organic layer may comprise a light emitting layer or both a light emitting layer and a hole transport layer, which may comprise a mixture or composition for preparing the organic electroluminescent device of the present invention.
The organic electroluminescent device of the present invention may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds, in addition to the compound of formula 1.
In the organic electroluminescent device of the present invention, the organic layer may further comprise at least one metal selected from the group consisting of: organometallic of group 1 metals, group 2 metals, period 4 transition metals, period 5 transition metals, lanthanides and d-transition elements of the periodic table, or at least one complex compound comprising said metals. The organic layer may further include a light emitting layer and a charge generation layer.
In addition, the organic electroluminescent device of the present invention may emit white light by further comprising at least one light emitting layer comprising a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the art in addition to the compound of the present invention.
In the organic electroluminescent device of the present invention, preferably, at least one layer (hereinafter, "surface layer") may be disposed on an inner surface of one or both electrodes, the inner surface being selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer. Specifically, a layer of a chalcogenide (including oxide) of silicon or aluminum is preferably located on the anode surface of the electroluminescent interlayer, and a layer of a metal halide or metal oxide is preferably located on the cathode surface of the electroluminescent interlayer. 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 includes LiF, MgF2、CaF2Rare earth metal fluorides, etc.; and the metal oxide comprises Cs2O、Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present invention, 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 is easy to inject an electron and transport it from the mixing region into the electroluminescent medium. In addition, the hole-transporting compound is oxidized to cations, and thus holes are easily injected and transported from the mixing region to the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids (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 reducible dopant layer may be used as a charge generation layer to fabricate an electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present invention, a dry film forming method such as vacuum evaporation, sputtering, plasma, and ion plating method; or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, and flow coating.
When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing a material forming each layer into any suitable solvent, for example, ethanol, chloroform, tetrahydrofuran, dioxane, or the like. The solvent may be any solvent in which the material forming each layer is soluble or diffusible and which does not present film forming ability problems.
Hereinafter, the organic electroluminescent compounds, the preparation methods of the compounds, and the light emitting characteristics of the devices of the present invention will be specifically explained with reference to the following examples.
Example 1: preparation of Compound C-1
Figure BDA0003221739530000221
Preparation of Compound 1-1
After 6-bromoindanone (50g, 237mmol), benzene dicarbaldehyde (35g, 261mmol), and 600mL of ethanol were introduced into the reaction vessel, the mixture was refluxed for 3 hours. The reaction mixture was cooled to 0 ℃. The crystalline solid was filtered and washed with cold methanol to give compound 1-1(47g, 64%).
Preparation of Compounds 1-2
After iodine (13.5g, 53.2mmol), hypophosphorous acid (25mL, 243mmol, 50% aqueous solution) and 800mL of acetic acid were introduced into the reaction vessel, the mixture was stirred at 100 ℃ for 30 minutes. After slowly adding compound 1-1 dropwise, the mixture was stirred overnight. The reaction mixture was cooled to room temperature. The crystalline solid was filtered and washed with cold methanol to give compound 1-2(41.5g, 92%).
Preparation of Compounds 1-3
After introducing compound 1-2(39g, 132mmol), potassium hydroxide (37g, 660mmol), potassium iodide (2.2g, 13.3mmol), benzyltriethylammonium chloride (1.5g, 6.6mmol), 700mL of distilled water and 700mL of dimethyl sulfoxide into a reaction vessel, the mixture was stirred at room temperature for 15 minutes. After addition of methyl iodide (37g, 330mmol), the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with distilled water. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compounds 1-3(33g, 77%).
Preparation of Compound C-1
To a reaction vessel were introduced compound 1-3(10g, 31mmol), biphenyl-4-ylamine (9.9g, 31mmol), palladium (II) acetate (0.25g, 1.24mmol), tri-tert-butylphosphine (1mL, 3.1mmol, 50% xylene solution), sodium tert-butoxide (4.5g, 46.5mmol) and 150mL o-xylene, and the mixture was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed several times with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-1(9.6g, 55%). The physical properties of compound C-1 are shown in Table 1 below.
Example 2: preparation of Compound C-43
Figure BDA0003221739530000231
Preparation of Compound 2-1
Compound 2-1 was prepared in the same manner as compounds 1-1 to 1-3 in example 1, except that 5-bromoindanone was used instead of 6-bromoindanone.
Preparation of Compound C-43
To a reaction vessel, compound 2-1(10g, 31mmol), biphenyl-4-ylamine (9.9g, 31mmol), palladium (II) acetate (0.25g, 1.24mmol), tri-tert-butylphosphine (1mL, 3.1mmol, 50% xylene solution), sodium tert-butoxide (4.5g, 46.5mmol) and 150mL o-xylene were introduced, and the mixture was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed several times with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-43(10.8g, 62%). The physical properties of compound C-43 are shown in Table 1 below.
Example 3: preparation of Compound H-71
Figure BDA0003221739530000232
Preparation of Compound 3-1
After introducing 11H-benzo [ b ] fluoren-11-one (41.5g, 181mmol) and 550mL of tetrahydrofuran into the reaction vessel, the reaction mixture was cooled to 0 ℃ and phenylmagnesium bromide (78mL, 235mmol, 3M in ether) was slowly added dropwise thereto. The reaction mixture was stirred at room temperature for 1 hour. After the reaction was terminated by adding an aqueous ammonium chloride solution to the reaction mixture, the mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound 3-1(56g, 99%).
Preparation of Compound 3-2
After introducing compound 3-1(28g, 90.3mmol), 4-bromotriphenylamine (88g, 271mmol), and dichloromethane (MC) (600mL) into the reaction vessel, the mixture was subjected to a nitrogen atmosphere. To the mixture was slowly added dropwise 3mL of Eaton's reagent. The mixture was stirred at room temperature for 2 hours. After the reaction was terminated by adding distilled water, the mixture was extracted with dichloromethane. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 3-2(38.9g, 70%).
Preparation of Compound C-71
Compound 3-2(10g, 16.27mmol), 2-naphthylboronic acid (3.4g, 19.5mmol), tetrakis (triphenylphosphine) palladium (0.7g, 0.65mmol), potassium carbonate (5.6g, 40.7mmol), 60mL of toluene, and 20mL of ethanol were introduced into a reaction vessel, and 20mL of distilled water was added to the mixture. The mixture was stirred at 120 ℃ for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-71(7.6g, 71%). The physical properties of compound C-71 are shown in Table 1 below.
Example 4: preparation of Compound C-89
Figure BDA0003221739530000241
Preparation of Compound C-89
To a reaction vessel were introduced the compounds 1-3(5g, 15.4mmol), 9-phenyl-9H, 9'H-3,3' -dicarbazole (6.6g, 16.2mmol), copper iodide (1.47g, 7.73mmol), diaminocyclohexane (3.7mL, 30.9mmol), potassium phosphate (9.85g, 46.4mmol), and 100mL o-xylene, and the mixture was refluxed for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed several times with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-89(4.8g, 47%). The physical properties of compound C-89 are shown in Table 1 below.
Example 5: preparation of Compound C-125
Figure BDA0003221739530000251
Preparation of Compound 5-1
After dibenzofuran (21g, 127mmol) and 330mL of tetrahydrofuran were introduced into the reaction vessel, the mixture was subjected to a nitrogen atmosphere and cooled to-78 ℃. After slowly adding n-butyllithium (50mL, 2.5M, 115mmol) dropwise, the mixture was stirred at-78 ℃ for 2 hours. After slowly adding 11H-benzo [ B ] fluoren-11-one (26g, 115mmol) dissolved in 330mL tetrahydrofuran dropwise, the mixture was allowed to warm slowly to room temperature and stirred overnight. After an aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, the mixture was extracted with dichloromethane (MC). The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 5-1(44g, 96%).
Preparation of Compound 5-2
After introducing compound 5-1(44g, 110mmol), 4-bromotriphenylamine (89g, 276mmol) and 550mL of MC into the reaction vessel, the mixture was cooled to 0 ℃. After adding Eton's reagent (2.4mL, 2.2mmol), the mixture was warmed to room temperature and stirred for 3 hours. After an aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, the mixture was extracted with MC. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 5-2(55g, 71%).
Preparation of Compound C-125
After introducing compound 5-2(10g, 14.1mmol), 2-naphthylboronic acid (2.6g, 15.6mmol), tetrakis (triphenylphosphine) palladium (0.8g, 0.71mmol), potassium carbonate (4.7g, 34.1mmol), 70mL of toluene, and 17mL of ethanol into a reaction vessel, 17mL of distilled water was added to the mixture. The mixture was stirred at 120 ℃ for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with MC. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to give compound C-125(8.4g, 80%). The physical properties of compound C-125 are shown in Table 1 below.
[ TABLE 1]
Figure BDA0003221739530000252
Figure BDA0003221739530000261
[ device example 1]OLEDs Using the Compounds of the invention
Using the material of the inventionThe OLED was manufactured as follows. A transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) on a glass substrate of an Organic Light Emitting Diode (OLED) (geomantec) was ultrasonically washed with acetone and isopropyl alcohol in sequence, and then stored in isopropyl alcohol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Adding N1, N1'- ([1,1' -biphenyl)]-4,4' -diyl) bis (N1- (naphthalen-1-yl) -N4, N4-diphenylbenzene-1, 4-diamine) was introduced into a unit of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10E-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate. Then, compound C-1 was introduced into another unit of the vacuum vapor deposition apparatus and evaporated by applying a current to the unit, thereby forming a hole transport layer having a thickness of 20nm on the hole injection layer. Thereafter, compound H-1 shown in table 2 below was introduced into one unit of the vacuum vapor deposition apparatus as a host material, and compound D-1 was introduced into the other unit as a dopant. The two materials were evaporated at different rates so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and the dopant, forming a light-emitting layer having a thickness of 30nm on the hole transport layer. Followed by reacting 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole is incorporated into one unit and quinolyl lithium is incorporated into the other unit. The two materials were evaporated at the same ratio so that they were deposited at doping amounts of 50 wt%, respectively, to form an electron transport layer having a thickness of 30nm on the light emitting layer. After deposition of quinolyl lithium on the electron transport layer to form an electron injection layer having a thickness of 2nm, an Al cathode having a thickness of 150nm was then deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, the OLED is manufactured. All materials used to fabricate OLEDs are prepared by reacting at 10E-6Those materials purified by vacuum sublimation. The manufactured OLED has a display brightness of 1,500cd/m2And the current density was 3.5mA/cm2Green light emission of (2).
[ device example 2]OLEDs Using the Compounds of the invention
An OLED was fabricated in the same manner as in device example 1, except that a hole transport layer was formed using compound C-71, and compounds H-2 and H-3 shown in Table 2 below were used as hosts. The manufactured OLED has the display brightness of 700cd/m2And the current density was 14.0mA/cm2Blue light emission of (2).
[ device example 3]OLEDs Using the Compounds of the invention
An OLED was manufactured in the same manner as device example 1, except that compound C-89 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed a luminance of 900cd/m2And the current density is 1.9mA/cm2Green light emission of (2).
[ device example 4]OLEDs Using the Compounds of the invention
An OLED was fabricated in the same manner as in device example 1, except that a hole transport layer was formed using compound C-125, and compounds H-2 and H-3 were used as hosts. The manufactured OLED has a display brightness of 1,200cd/m2And the current density was 25.0mA/cm2Blue light emission of (2).
Comparative example 1]OLEDs using conventional compounds
An OLED was manufactured in the same manner as device example 1, except that a hole transport layer having a thickness of 20nm was formed using compound T-1 as shown in table 2 below. The manufactured OLED has the display brightness of 9,800cd/m2And the current density was 26.1mA/cm2Green light emission of (2).
Comparative example 2]OLEDs using conventional compounds
An OLED was fabricated in the same manner as in device example 1, except that a hole-transporting layer was formed using compound T-1, and compounds H-2 and H-3 were used as hosts. The manufactured OLED has the display brightness of 2,800cd/m2And the current density was 141.2mA/cm2Blue light emission of (2).
As demonstrated by the device examples, the compounds of the organic electronic material of the present invention have better light emitting characteristics than conventional compounds. The organic electroluminescent device comprising the compound for an organic electronic material according to the present invention shows superiority in light emitting characteristics and lifetime.
[ TABLE 2]
Figure BDA0003221739530000271

Claims (4)

1. An organic electroluminescent compound represented by the following formula 1:
Figure FDA0003221739520000011
wherein
Ar1And Ar2Each independently represents phenyl, biphenyl, bitriphenyl, naphthyl, 9-dimethyl-9H-fluorenyl, naphthylphenyl or phenylnaphthyl;
Ar3and Ar4Each independently represents phenyl, biphenyl, naphthyl, naphthylphenyl or phenylnaphthyl;
Ar5represents a methyl group, a phenyl group, a dibenzothienyl group or a dibenzofuranyl group;
L1represents a single bond or an unsubstituted phenylene group;
L2represents a methyl group or a phenyl group;
R1and R2Each independently represents hydrogen or deuterium;
n and m each independently represent 0 or 1, with the proviso that n and m cannot both be 0;
a represents an integer of 3; when a is an integer of 2 or more, each R1May be the same or different;
b represents an integer of 6; when b is an integer of 2 or more, each R2May be the same or different.
2. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is represented by any one of the following formulae 2 to 4:
Figure FDA0003221739520000012
Figure FDA0003221739520000021
wherein
Ar1To Ar5、L1、L2、R1、R2A and b are as defined in claim 1.
3. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is selected from the group consisting of:
Figure FDA0003221739520000022
Figure FDA0003221739520000031
Figure FDA0003221739520000041
Figure FDA0003221739520000051
4. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
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