CN116947847A - Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same - Google Patents

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Download PDF

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CN116947847A
CN116947847A CN202310412150.2A CN202310412150A CN116947847A CN 116947847 A CN116947847 A CN 116947847A CN 202310412150 A CN202310412150 A CN 202310412150A CN 116947847 A CN116947847 A CN 116947847A
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substituted
unsubstituted
group
membered
alkyl
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金东吉
李孝姃
赵相熙
朴景秦
愼孝壬
朴笑美
全廷桓
姜炫周
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same. By including the organic electroluminescent compounds according to the present disclosure as an organic electroluminescent material, or by including a specific combination of the compounds according to the present disclosure as various host materials, an organic electroluminescent device having improved driving voltage and/or luminous efficiency can be produced.

Description

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
Technical Field
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.
Background
A small-molecule green organic electroluminescent device (OLED) was first developed by Tang et al from Eastman Kodak, inc. Thereafter, the development of the OLED is rapidly completed and the OLED has been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel realization. In many applications, such as TV and lighting devices, the lifetime of the OLED is insufficient and still a higher efficiency of the OLED is required. Typically, the higher the luminance of an OLED, the shorter the lifetime of the OLED. Accordingly, for long-term use and high resolution of the display, an OLED having high luminous efficiency and/or long lifetime is required. In order to improve the light emitting efficiency, driving voltage and/or lifetime, various materials or concepts for the organic layer of the OLED have been proposed. However, they are not satisfactory in practical use.
Meanwhile, japanese patent application laid-open No. 1995-053950 discloses a condensed ring compound. However, the foregoing references do not specifically disclose organic electroluminescent compounds and a variety of host materials comprising specific combinations of compounds as claimed in the present disclosure. Furthermore, there remains a need to develop luminescent materials with more improved properties (e.g. lower driving voltage and/or higher luminescent efficiency characteristics) compared to the compounds disclosed in the aforementioned references.
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide various improved host materials capable of providing an organic electroluminescent device having improved driving voltage and/or luminous efficiency. It is another object of the present disclosure to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. It is still another object of the present disclosure to provide an organic electroluminescent device having improved driving voltage and/or luminous efficiency by including the compound of the present disclosure or a specific combination of the compounds of the present disclosure.
Solution to the problem
As a result of intensive studies to solve the technical problems, the present inventors have found that the above object can be achieved by a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1, and wherein the second host compound is represented by the following formula 2. Furthermore, the present inventors have found that the above object can be achieved by the compound represented by the following formula 1.
In the formula (1) of the present invention,
R 1 to R 8 Each 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) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L 1 -Ar 1 The method comprises the steps of carrying out a first treatment on the surface of the Or may be linked to one or more adjacent substituents to form one or more rings;
provided that R 1 To R 8 At least one of them represents-L 1 -Ar 1 ；
L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;
Ar 1 each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-N- (R') (R "); and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
In the formula (2) of the present invention,
L 2 and L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 2 and Ar is a group 3 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted (C6-to 30-membered) heteroaryl groupUnsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted tri (C6-C30) arylsilyl;
R 9 to R 12 Each 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 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 (C3-C30) aliphatic ring and substituted or unsubstituted fused ring group of one or more (C6-C30) aromatic rings, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl2-alkenyl amino, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted (C3-C30-membered heteroaryl, substituted or unsubstituted amino (C1-C30) alkylamino, substituted or unsubstituted (C2-C30-membered alkylamino, substituted or unsubstituted (C2-C30) alkylamino Substituted or unsubstituted mono-or di- (C6-C30) arylamino, substituted or unsubstituted mono-or di- (3-to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino; or may be linked to one or more adjacent substituents to form one or more rings; and is also provided with
a and d each independently represent an integer of 1 to 4, and b and c each independently represent an integer of 1 to 3, wherein each R is if a to d is an integer of 2 or more 9 To each R 12 May be the same or different from each other.
The beneficial effects of the invention are that
A variety of host materials and organic electroluminescent compounds according to the present disclosure exhibit properties suitable for use in organic electroluminescent devices. Further, by including the compound according to the present disclosure as an organic electroluminescent material or including a specific combination of the compounds according to the present disclosure as a variety of host materials, an organic electroluminescent device is provided which has a lower driving voltage and/or higher luminous efficiency than conventional organic electroluminescent devices and which can be used to produce a display system or an illumination system.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure in any way.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including host materials and dopant materials), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The term "multiple host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which may be contained in any light emitting layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of host materials of the present disclosure may be a combination of at least two host materials, which may optionally further comprise conventional materials included in organic electroluminescent materials. At least two compounds included in the plurality of host materials of the present disclosure may be included together in one light emitting layer, or each may be included in a different light emitting layer. For example, at least two host materials may be co-evaporated or co-evaporated, or may be separately evaporated.
In this context, the term "(C1-C30) alkyl" or "(C1-C30) alkylene" means a straight or branched alkyl or alkylene group having from 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably from 1 to 10, and more preferably from 1 to 6. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30) cycloalkyl" or "(C3-C30) cycloalkylene" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably from 3 to 20, and more preferably from 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3-to 7-membered) heterocycloalkyl" means cycloalkyl having 3 to 7 ring backbone atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, si and P, and preferably O, S and N. The above heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiopan), tetrahydropyran and the like. The term "(C6-C30) aryl" or "(C6-C30) arylene" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, and may be partially saturated. The aryl and arylene groups described above may comprise spiro structures. The aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, benzophenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like, Group, naphto-naphthyl group, fluoranthenyl group, spirobifluorenyl group, spiro [ fluorene-benzofluorene ]]Base, spiro [ cyclopentene-fluorene ]]Base, spiro [ indan-fluorene ]]Group, azulene group, tetramethyl-dihydrophenanthryl group, and the like. Specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl2-anthryl, 9-anthryl, benzanthraceyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthaceneyl, pyrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [ a ]]Fluorenyl and benzo [ b ]]Fluorenyl and benzo [ c ]]Fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-tetrabiphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-t-butylphenyl, p (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -t-butyl-p-terphenyl-4-yl, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl, 9-1-diphenyl, 9-diphenyl Phenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 11-dimethyl-1-benzo [ a ]]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ]]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ] ]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl, 11-diphenyl-3-benzo [ c ]]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl group,11, 11-diphenyl-6-benzo [ c ] ]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like.
The term "(3-to 30-membered) heteroaryl" or "(3-to 30-membered) heteroarylene" means an aryl or arylene group having 3 to 30 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, si and P. The number of heteroatoms is preferably 1 to 4. The heteroaryl or heteroarylene group may be a single ring or a condensed ring condensed with at least one benzene ring; and may be partially saturated. Further, the above heteroaryl or heteroarylene may be a heteroaryl or heteroarylene formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and may contain a spiro structure. The heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, dibenzotellurophenoyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofluoroquinolinyl, benzofluoroquinazolinyl, benzofluoronaphthyridinyl, benzofluoropyrimidinyl, naphthofluoropyrimidinyl, naphthobenzofuranyl, benzofuranyl, or combinations thereof benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthyridopyrimidinyl, pyrimidoindolyl, benzopyrimidino indolyl, benzofluoropyrazinyl, naphthyridopyrazinyl, benzothienopyrazinyl, naphthyridopyrazinyl, naphthyridinyl pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, benzoxazolyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzpyrimidinyl, indolocarzolyl, indenocarzolyl, and the like. More specifically, the process is carried out, the 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-indolyleridinyl (indidinyl), 2-indolyleridinyl, 3-indolyleridinyl, 5-indolyleridinyl, 6-indolyleridinyl, 7-indolyleridinyl, 8-indolyleridinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-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-furanyl, 2-thienyl, 3-thienyl, 2-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-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, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzo- [ 2-benzo-3-benzofuranyl, 2-benzofuranyl ] -2- [2, 2-b ] -2-naphtho-1-benzofuranyl, 2- [ b ] -2, 2-b ] -2-naphtalenyl 5-naphtho- [1,2-b ] -benzofuranyl, 6-naphtho- [1,2-b ] -benzofuranyl, 7-naphtho- [1,2-b ] -benzofuranyl, 8-naphtho- [1,2-b ] -benzofuranyl, 9-naphtho- [1,2-b ] -benzofuranyl, 10-naphtho- [1,2-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-naphtho- [2,3-b ] -benzofuranyl, 3-naphtho- [2,3-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 6-naphtho- [2,3-b ] -benzofuranyl, 7-naphtho- [2,3-b ] -benzofuranyl, 8-naphtho- [2,3-b ] -benzofuranyl, 9-naphtho- [2,3-b ] -benzofuranyl, 10-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2, 2-b ] -benzofuranyl, 5-naphtho-b ] -benzofuranyl, 6-naphtho- [2,1-b ] -benzofuranyl, 7-naphtho- [2,1-b ] -benzofuranyl, 8-naphtho- [2,1-b ] -benzofuranyl, 9-naphtho- [2,1-b ] -benzofuranyl, 10-naphtho- [2,1-b ] -benzofuranyl, 1-naphtho- [1,2-b ] -benzothienyl, 2-naphtho- [1,2-b ] -benzothienyl, 3-naphtho- [1,2-b ] -benzothienyl, 4-naphtho- [1,2-b ] -benzothienyl, 5-naphtho- [1,2-b ] -benzothienyl, 6-naphtho- [1,2-b ] -benzothienyl 7-naphtho- [1,2-b ] -benzothienyl, 8-naphtho- [1,2-b ] -benzothienyl, 9-naphtho- [1,2-b ] -benzothienyl, 10-naphtho- [1,2-b ] -benzothienyl, 1-naphtho- [2,3-b ] -benzothienyl, 2-naphtho- [2,3-b ] -benzothienyl, 3-naphtho- [2,3-b ] -benzothienyl, 4-naphtho- [2,3-b ] -benzothienyl, 5-naphtho- [2,3-b ] -benzothienyl, 1-naphtho- [2,1-b ] -benzothienyl, 2-naphtho- [2,1-b ] -benzothienyl, 3-naphtho- [2,1-b ] -benzothienyl, 4-naphtho- [2,1-b ] -benzothienyl, 5-naphtho- [2,1-b ] -benzothienyl, 6-naphtho- [2,1-b ] -benzothienyl, 7-naphtho- [2,1-b ] -benzothienyl, 8-naphtho- [2,1-b ] -benzothienyl, 9-naphtho- [2,1-b ] -benzothienyl, 10-naphtho- [2,1-b ] -benzothienyl, 2-benzofluoro [3,2-d ] pyrimidinyl, 6-benzofluoro [3,2-d ] pyrimidinyl, 7-benzofluoro [3,2-d ] pyrimidinyl, 8-benzofluoro [3,2-d ] pyrimidinyl, 9-benzo [3,2-d ] pyrimidinyl, 2-benzothiophen [3,2-d ] pyrimidinyl, 6-benzo [2,1-b ] -benzothienyl, 2-benzo [2, 1-d ] pyrazinyl, 2-fluoro [3,2-d ] pyrazinyl, 3-fluoro [2, 2-d ] pyrazinyl, 2-fluoro [2, 2-b ] pyrazinyl, 2-fluoro [ 2-b ] pyrrolyl, 2-naphthas been substituted by 2-naphthas [2,1-b ] -b-and, 6-benzothio [3,2-d ] pyrazinyl, 7-benzothio [3,2-d ] pyrazinyl, 8-benzothio [3,2-d ] pyrazinyl, 9-benzothio [3,2-d ] pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. In addition, "halogen" includes F, cl, br and I.
In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2. Meta-position means that two substituents are at positions 1 and 3 and is referred to as meta-position, for example, when two substituents in the benzene derivative occupy positions 1 and 3. Para represents two substituents at positions 1 and 4, and is referred to as para, for example, when two substituents in the benzene derivative occupy positions 1 and 4.
In the present disclosure, "a ring formed by the connection of adjacent substituents" means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof. The ring may preferably be a substituted or unsubstituted mono-or polycyclic (3-to 26-membered) alicyclic ring or aromatic ring, or a combination thereof, and more preferably a mono-or polycyclic (5-to 25-membered) aromatic ring that is unsubstituted or substituted with at least one of a (C6-C18) aryl group and a (3-to 20-membered) heteroaryl group. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring, a phenanthrene ring, an indole ring, a carbazole ring, a xanthene ring, or the like.
In this context, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced with a group formed by the connection of two or more substituents among the above-mentioned substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazines may be interpreted as heteroaryl substituents, or substituents in which two heteroaryl substituents are linked. Herein, one or more substituents of substituted alkyl (ene), substituted alkenyl (ene), substituted aryl (ene), substituted heteroaryl (ene), substituted cycloalkyl (ene), substituted alkoxy (ene), substituted trialkylsilyl (ene), substituted dialkylarylsilyl (ene), substituted alkyldiarylsilyl (ene), substituted triarylsilyl (ene), substituted fused ring groups of one or more aliphatic and one or more aromatic rings (ene), substituted mono-or di-alkylamino (ene), substituted mono-or di-alkenylamino (ene), substituted alkyl-alkenylamino (ene), substituted mono-or di-arylamino (ene), substituted alkylaryl amino (ene), substituted mono-or di-heteroarylamino (ene), substituted alkylheteroaryl amino (ene), substituted alkenylarylamino (ene) and substituted arylheteroaryl amino (ene) are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl and (3-to 30-membered) heteroaryl; tri (C1-C30) alkylsilyl; 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- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl, wherein these substituents may be further substituted with deuterium. According to one embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; (6-to 25-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C20) aryl; and (C6-C25) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C20) alkyl, (C6-C20) aryl, and (6-to 25-membered) heteroaryl. According to another embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; (6-to 18-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C15) aryl; and (C6-C20) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C10) alkyl, (C6-C18) aryl, and (6-to 18-membered) heteroaryl. For example, the one or more substituents may each independently be at least one selected from the group consisting of: deuterium; phenyl unsubstituted or substituted with deuterium, one or more fluoro, one or more naphthyl, or one or more dibenzo-telluro-phenyl; a biphenyl group; a terphenyl group; a naphthyl group; phenanthryl; a dimethylfluorenyl group; dibenzofuranyl; dibenzothienyl; dibenzotellurium phenoyl; and carbazolyl groups unsubstituted or substituted with one or more phenyl groups, wherein the substituents may be further substituted with deuterium.
Hereinafter, the compound represented by formula 1 will be described in more detail.
In formula 1, R 1 To R 8 Each 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) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L 1 -Ar 1 The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings. However, R is 1 To R 8 At least one of them represents-L 1 -Ar 1 . For example, R 1 To R 8 Can each independently be hydrogen, deuterium, -L 1 -Ar 1 Etc., and R is 1 To R 8 Any one of them may be-L 1 -Ar 1 。
L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstitutedSubstituted (3-to 30-membered) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L 1 Each independently represents a single bond, a (C6-C25) arylene group, unsubstituted or substituted with deuterium or one or more (C6-C18) aryl groups, or an unsubstituted (6-to 20-membered) heteroarylene group. According to another embodiment of the present disclosure, L 1 Each independently represents a single bond, a (C6-C18) arylene group, unsubstituted or substituted with deuterium or one or more (C6-C12) aryl groups, or an unsubstituted (6-to 18-membered) heteroarylene group. For example, L 1 May each independently be a single bond, phenylene, biphenylene, naphthylene, pyrimidinylene, dibenzofuranylene, carbazolylene, or the like, unsubstituted or substituted with deuterium or one or more phenyl groups.
Ar 1 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-N- (R') (R "). Heteroaryl groups may contain at least one nitrogen. According to one embodiment of the present disclosure, ar 1 Each independently represents a substituted or unsubstituted (6-to 25-membered) heteroaryl, wherein one or more substituents of the (6-to 25-membered) heteroaryl may be at least one selected from the group consisting of: (C6-C25) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C10) alkyl, (C6-C20) aryl and (6-to 20-membered) heteroaryl; and (6-to 20-membered) heteroaryl, unsubstituted or substituted with one or more (C6-C18) aryl groups. According to another embodiment of the present disclosure, ar 1 Each independently represents a substituted (6-to 18-membered) heteroaryl, wherein one or more substituents of the (6-to 18-membered) heteroaryl may be at least one selected from the group consisting of: (C6-C20) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C6) alkyl, (C6-C15) aryl, and (6-to 18-membered) heteroaryl; and (6-to 18-membered) heteroaryl, unsubstituted or substituted with one or more (C6-C15) aryl groups. According to yet another embodiment of the present disclosure, ar 1 Each independently represents a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstitutedA substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofluoropyrimidinyl group, a substituted or unsubstituted benzothiophenyl pyrimidinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzonaphthyridinyl group, or a substituted or unsubstituted benzonaphthyridinyl group. For example, ar 1 May each independently be a substituted triazinyl group; quinazolinyl unsubstituted or substituted with at least one of phenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl; benzoquinazolinyl unsubstituted or substituted with one or more phenyl groups or one or more dibenzofuranyl groups; quinoxalinyl unsubstituted or substituted with at least one of phenyl, biphenyl, naphthyl and dibenzofuranyl; benzoquinoxalinyl substituted with one or more phenyl groups; benzofuropyrimidinyl substituted with one or more phenyl groups; benzothiophenopyrimidinyl substituted with one or more phenyl groups, and the like, wherein the one or more substituents of the triazinyl group may be at least one selected from the group consisting of: phenyl unsubstituted or substituted with deuterium, one or more fluoro, one or more naphthyl or one or more dibenzotellurium phenoyl; a biphenyl group; a terphenyl group; a naphthyl group; phenanthryl; a dimethylfluorenyl group; dibenzofuranyl; dibenzothienyl; dibenzotellurium phenoyl; carbazolyl groups unsubstituted or substituted with one or more phenyl groups, and the like.
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
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The present disclosure provides an organic electroluminescent compound represented by formula 1, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the organic electroluminescent material. The organic electroluminescent material may consist of only the organic electroluminescent compounds of the present disclosure, or may further comprise conventional materials included in the organic electroluminescent material.
The organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include an organic electroluminescent material containing a compound represented by formula 1 as the organic electroluminescent material.
The organic electroluminescent compound represented by formula 1 of the present disclosure may be contained in any one of a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, and if necessary, is preferably contained in at least one of a light emitting layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. When used in an electron transport layer, the organic electroluminescent compound represented by formula 1 of the present disclosure may be contained as an electron transport material. When used in an electron buffer layer, the organic electroluminescent compound represented by formula 1 of the present disclosure may be contained as an electron buffer material. When used in a light emitting layer, the organic electroluminescent compound represented by formula 1 of the present disclosure may be contained as a host material. If desired, the organic electroluminescent compounds of the disclosure can be used as co-host materials.
A plurality of host materials according to one embodiment of the present disclosure include a first host material and a second host material, wherein the first host material includes at least one compound represented by formula 1, and the second host material includes at least one compound represented by formula 2.
Hereinafter, the compound represented by formula 2 will be described in more detail.
In formula 2, L 2 And L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L 2 And L 3 Each independently represents a single bond, unsubstituted or deuterium-substituted (C6-C20) arylene, or unsubstituted or deuterium-substituted (6-to 20-membered) heteroarylene. According to another embodiment of the present disclosure, L 2 And L 3 Each independently represents a single bond, unsubstituted or deuterium-substituted (C6-C18) arylene, or unsubstituted or deuterium-substituted (6-to 18-membered) heteroarylene. For example, L 2 And L 3 Each independently may be a single bond, or a phenylene, biphenylene, naphthylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, or the like, which is unsubstituted or substituted with deuterium.
In formula 2, ar 2 And Ar is a group 3 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, or a substituted or unsubstituted tri (C6-C30) alkylsilyl group) Arylsilyl groups. According to one embodiment of the present disclosure, ar 2 And Ar is a group 3 Each independently represents an unsubstituted or deuterium-substituted (C6-C25) aryl group; or a (3-to 25-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and (C6-C25) aryl. According to another embodiment of the present disclosure, ar 2 And Ar is a group 3 Each independently represents an unsubstituted or deuterium-substituted (C6-C20) aryl group; or a (3-to 20-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and (C6-C20) aryl. For example, ar 2 And Ar is a group 3 Each independently may be phenyl; a biphenyl group; a terphenyl group; a naphthyl group; triphenylene; dibenzofuranyl; dibenzothienyl; carbazolyl substituted with one or more phenyl groups or one or more naphthyl groups, etc., which may be substituted with deuterium.
In formula 2, R 9 To R 12 Each 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 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 (C3-C30) aliphatic ring and substituted or unsubstituted fused ring group of one or more (C6-C30) aromatic rings, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl2-alkenyl amino, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted (C3-C30-membered heteroaryl, substituted or unsubstituted amino (C1-C30) alkylamino, substituted or unsubstituted (C2-C30-membered alkylamino, substituted or unsubstituted (C2-C30) alkylamino Substituted or unsubstituted mono-or di- (C6-C30) arylamino, substituted or unsubstituted mono-or di- (3-to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino, or may be attached to one or more adjacent substituents to form one or more rings. For example, R 9 To R 12 Each independently may be hydrogen, deuterium, or the like.
In formula 2, a and d each independently represent an integer of 1 to 4, and b and c each independently represent an integer of 1 to 3, wherein each R if a to d is an integer of 2 or more 9 To each R 12 May be the same or different from each other.
According to one embodiment of the present disclosure, formula 2 may be represented by formula 2-1 below.
In formula 2-1, L 2 、L 3 、Ar 2 、Ar 3 、R 9 To R 12 And a to d are as defined in formula 2.
The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
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In the compounds H2-1 to H2-270, D n Represents that n number of hydrogens are replaced with deuterium, and n represents an integer of 1 to 44. Specifically, n represents an integer of 1 or more, and the upper limit of n is the number of hydrogens in each compound. Preferably, n is an integer of 4 or more, and more preferably, n is an integer of 11 or more. When deuterated to a lower limit number or more, bond dissociation energy associated with deuteration may be increased to improve stability of the compound, and thus, the compound may exhibit improved lifetime characteristics when used in an organic electroluminescent device.
The combination of at least one of the compounds C-1 to C-95 and at least one of the compounds H2-1 to H2-270 may be used in an organic electroluminescent device.
The compound represented by formula 1 according to the present disclosure may be produced by referring to the following reaction schemes 1 and 2, but is not limited thereto.
The compound represented by formula 2 according to the present disclosure may be produced by synthetic methods known to those skilled in the art, for example, by referring to korean patent laid-open No. 10-2283849 (published 8/2/2021) and japanese patent application laid-open No. 1996-003547 (published 1/9/1996), but is not limited thereto.
Reaction scheme 1
Reaction scheme 2
In schemes 1 and 2, L 1 And Ar is a group 1 Is as defined in formula 1.
Although illustrative synthetic examples of the compounds represented by formula 1 are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartmay (Buchwald-Hartwig) cross-coupling reactions, C-C coupling reactions, sandmeyer reactions, oxidative cyclization reactions, N-arylation reactions, acidified montmorillonite (H-mont) mediated etherification reactions, miyaura) boration reactions, suzuki (Suzuki) cross-coupling reactions, intramolecular acid induced cyclization reactions, pd (II) catalyzed oxidative cyclization reactions, grignard reactions (Grignard Reaction), herke reactions (Heck reactions), dehydrative cyclization reactions, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and the above reaction proceeds even when a substituent defined by the above formula 1 but not specified in a specific synthesis example is bonded.
The present disclosure provides an organic electroluminescent device comprising an anode, a cathode, and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of host materials according to the present disclosure. The first host material and the second host material of the present disclosure may be contained in one light emitting layer, or may be contained in different light emitting layers among a plurality of light emitting layers, respectively. The various host materials of the present disclosure may comprise 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 in a ratio of about 10:90 to about 90:10, more preferably in a ratio of about 30:70 to about 70:30. Further, the compound represented by formula 1 and the compound represented by formula 2 in a desired ratio may be combined by mixing them in a shaker, by dissolving them in a glass tube via heating, or by dissolving them in a solvent or the like.
According to one embodiment of the present disclosure, the dopant compound may have a doping concentration of less than 20wt% relative to the host compound in the light emitting layer. The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be a complex compound of metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and is preferably a orthometalated complex compound of a metal atom selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metalated iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following formula 101, but is not limited thereto.
In the case of the method 101,
l is selected from the following structures 1 to 3:
R 100 to R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or one or more halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to one or more adjacent substituents to form together with pyridine one or more rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenoquinoline;
R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to one or more adjacent substituents to form together with benzene one or more substituted or unsubstituted rings, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothiophenopyridine;
R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted with deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to one or more adjacent substituents to form one or more substitutions orAn unsubstituted ring; and is also provided with
s represents an integer of 1 to 3.
Specific examples of the dopant compounds are as follows, but are not limited thereto.
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The organic electroluminescent device according to the present disclosure has an anode; a cathode; and at least one organic layer between the anode and the cathode. The organic layer may include a light emitting layer, and may further include at least one layer selected from a hole injecting layer, a hole transporting layer, a hole assisting layer, a light emitting assisting layer, an electron transporting layer, an electron buffering layer, an electron injecting layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of these layers may be further configured as multiple layers.
The anode and cathode may each be formed of a transparent conductive material, or a transflective or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type, depending on materials forming the anode and the cathode. In addition, the hole injection layer may be further doped with one or more p-type dopants, and the electron injection layer may be further doped with one or more n-type dopants.
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. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: a metal of group 1 of the periodic table, a metal of group 2, a transition metal of group 4, a transition metal of group 5, an organometallic of the lanthanide series and the d-transition element, or at least one complex compound comprising the one or more metals.
In addition, the organic electroluminescent device of the present disclosure may emit white light by further including at least one light emitting layer including a blue, red or green electroluminescent compound known in the art in addition to the compound of the present disclosure. It may further comprise a yellow or orange light emitting layer, if desired.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer may be placed on one or more inner surfaces of one or both electrodes. In particular, a chalcogenide (including oxide) layer of silicon or aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like, and the metal halide comprises LiF and MgF 2 、CaF 2 Rare earth metal fluorides, etc., and metal oxides including Cs 2 O、Li 2 O, 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 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 plurality of layers to control injection of electrons and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the plurality of 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 multilayer may use a plurality of compounds.
The light emitting auxiliary layer may be placed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to promote 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 promote 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 hole injection layer) and the light emitting layer, and the hole transport rate (or hole injection rate) may be effectively promoted or limited, thereby enabling control of charge balance. Further, an electron blocking layer may be disposed between the hole transporting layer (or hole injecting 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 further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving efficiency and/or lifetime of the organic electroluminescent device.
Further, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus injection and transport of electrons from the mixed region to the light emitting medium become easier. In addition, the hole transport compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the light emitting medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds, and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer may be used as a charge generation layer to produce an organic electroluminescent device having two or more light emitting layers and emitting white light.
According to one embodiment of the present disclosure, an organic electroluminescent material may be used as a light emitting material for a white organic light emitting device. A white organic light emitting device has been proposed to have various structures such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light emitting members, or a Color Conversion Material (CCM) method, or the like. According to one embodiment of the present disclosure, the organic electroluminescent material may also be used in an organic electroluminescent device comprising Quantum Dots (QDs).
In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, or the like may be used. When the first host compound and the second host compound of the present disclosure are used to form a film, a co-evaporation process or a mixed evaporation process is performed.
When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in terms of film forming ability.
Further, a display system, for example, 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 organic electroluminescence device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, a method of preparing the compound according to the present disclosure and characteristics thereof, and a driving voltage and light emitting efficiency of an organic electroluminescent device (OLED) including a plurality of host materials according to the present disclosure will be explained in detail with reference to representative compounds of the present disclosure. The following examples only describe the characteristics of the compounds according to the present disclosure and OLEDs comprising the same, but the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-60
1) Synthesis of Compound A-2
Compound A-1 (37 g,178 mmol), 4 '-chloro- [1,1' -biphenyl]2-amine (85.3 g,196 mmol), palladium (II) acetate (2.0 g,8.91 mmol), sphos (7.3 g,17.8 mmol), and K 2 CO 3 (49.2 g,356 mmol) was added to the flask, dissolved in 600mL of toluene, 150mL of ethanol, and 150mL of distilled water, and then refluxed for 16 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, dried over magnesium sulfate, and then filtered with silica gel to obtain compound A-2 (69 g, yield: 81%).
2) Synthesis of Compound A-3
In a flask, compound A-2 (68.5 g,144 mmol) and p-toluene sulfonic acid (82.0 g,431 mmol) were dissolved in 600mL of acetonitrile and stirred at 0deg.C for 30 min. Sodium nitrite (19.8 g,287 mmol) was dissolved in 50mL of distilled water and added dropwise to the stirred flask. Potassium iodide (59.6 g, 319 mmol) was dissolved in 50mL of distilled water and added to the reaction mixture. The reaction mixture was stirred at 50℃for 3 hours. After the completion of the reaction, the organic layer was extracted with methylene chloride, dried over magnesium sulfate, and then separated by column chromatography to obtain compound A-3 (38.4 g, yield: 45%).
3) Synthesis of Compound A-4
Compound A-3 (19.2 g,32.7 mmol) and trifluoromethanesulfonic acid (14.7 g,98.1 mmol) were added to the flask, dissolved in 1.6L of dichloromethane, and then stirred at 0deg.C for 30 minutes. Next, m-CPBA (77 wt%,11.0g,49.1 mmol) was added to the mixture, and stirred at reflux for 1 hour. After completion of the reaction, the resulting solid precipitate was filtered and washed with ethyl acetate to obtain compound A-4 (15.0 g, yield: 63%).
4) Synthesis of Compound C-60
Compound A-4 (15 g,20.4 mmol) and tellurium (3.9 g,30.6 mmol) were added to the flask, dissolved in 130mL of DMSO and 70mL of 2-Pi Kaolin (2-picoline), and then stirred at 130℃for 48 hours. After the completion of the reaction, the organic layer was extracted with methylene chloride, dried over magnesium sulfate, and then separated by column chromatography to obtain compound C-60 (2.2 g, yield: 18%).
Device example 1: producing an OLED according to the present disclosure
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (japanese Ji Aoma limited (GEOMATECCO., LTD., japan)) on a glass substrate for OLED was sequentially ultrasonically washed with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate is then mounted on a substrate support of a vacuum vapor deposition apparatus. The compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus and the compound HT-1 was introduced into the other cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and the compound HI-1 was deposited at a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a hole injection layer having a thickness of 10 nm. Next, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Subsequently, the compound HT-2 was then 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 transport layer having a thickness of 30nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the first master shown in Table 1 below will be Each of the bulk compound and the second host compound is introduced as a host into two cells of a vacuum vapor deposition apparatus, and compound D-130 is introduced as a dopant into the other cell. The two host materials were evaporated at a rate of 1:2, and the dopant materials were simultaneously evaporated at different rates, and the dopants were deposited at a doping amount of 10wt% based on the total of the host and dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Next, the compound ETL-1 and the compound EIL-1 were evaporated as electron transport materials in a weight ratio of 40:60 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After depositing the compound EIL-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 using another vacuum vapor deposition apparatus. Thereby, an OLED is produced. All materials used for producing the OLED are shown in 10 -6 Purification by vacuum sublimation was performed under the tray.
Device example 2: producing an OLED according to the present disclosure
An OLED was produced in the same manner as in device example 1, except that only compound C-60 was used as the host of the light-emitting layer.
Comparative example: producing an OLED comprising a compound not according to the present disclosure as a host
An OLED was produced in the same manner as in device example 1, except that only compound CBP was used as a host of the light emitting layer to form the light emitting layer, compound Balq was deposited as a hole blocking layer having a thickness of 5nm, and compound ETL-1 and compound EIL-1 were deposited as electron transporting materials at a weight ratio of 40:60 to form an electron transporting layer having a thickness of 30nm on the hole blocking layer.
The driving voltages, luminous efficiencies and emission colors of the OLEDs produced in the device examples 1 and 2 and the comparative example at a luminance of 1,000 nits are provided in table 1 below.
TABLE 1
As can be confirmed from table 1 above, the OLED (device example 1) including the specific combination of the compounds according to the present disclosure as the host material and the OLED (device example 2) including the organic electroluminescent compound according to the present disclosure exhibited lower driving voltage and higher light emitting efficiency, and particularly had significantly improved driving voltage, compared to the OLED (comparative example) including the compound not according to the present disclosure.
The compounds used in the device examples and comparative examples are shown in table 2 below.
TABLE 2
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Claims (11)

1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2:
In the formula (1) of the present invention,
R 1 to R 8 Each 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) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L 1 -Ar 1 The method comprises the steps of carrying out a first treatment on the surface of the Or may be linked to one or more adjacent substituents to form one or more rings;
provided that R 1 To R 8 At least one of them represents-L 1 -Ar 1 ；
L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;
Ar 1 each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-N- (R') (R "); and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
In the formula (2) of the present invention,
L 2 and L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 2 and Ar is a group 3 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, or a substituted or unsubstituted tri (C6-C30) arylsilyl group;
R 9 to R 12 Each 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 tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilylA substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C2-C30) alkenylamino group, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino group, a substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino group, a substituted or unsubstituted (C2-C30-membered) heteroarylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, a substituted or unsubstituted (C6-C30-membered heteroaryl (3-to 30-membered heteroaryl) amino group; or may be linked to one or more adjacent substituents to form one or more rings; and is also provided with
a and d each independently represent an integer of 1 to 4, and b and c each independently represent an integer of 1 to 3, wherein each R is if a to d is an integer of 2 or more 9 To each R 12 May be the same or different.
2. The plurality of host materials of claim 1, wherein one or more substituents of the substituted alkyl (ene), the substituted alkenyl, the substituted aryl (ene), the substituted heteroaryl (ene), the substituted cycloalkyl (ene), the substituted alkoxy (e), the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring group of one or more aliphatic rings and one or more aromatic rings, the substituted mono-or di-alkylamino, the substituted mono-or di-alkenylamino, the substituted alkylalkenylamino, the substituted mono-or di-arylamino, the substituted alkylaryl amino, the substituted mono-or di-heteroarylamino, the substituted alkylheteroarylamino, the substituted alkenylarylamino, the substituted alkenylheteroarylamino, and the substituted arylheteroarylamino are each independently selected from at least one of the following: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl and (3-to 30-membered) heteroaryl; tri (C1-C30) alkylsilyl; 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- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
3. The plurality of host materials of claim 1, wherein Ar 1 Each independently represents a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofluoropyrimidinyl group, a substituted or unsubstituted benzothiophenopyrimidinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstitutedBenzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthyridinyl, or substituted or unsubstituted benzonaphthyridinyl.
4. The plurality of host materials of claim 1, wherein formula 2 is represented by the following formula 2-1:
in the formula 2-1 of the present invention,
L 2 、L 3 、Ar 2 、Ar 3 、R 9 to R 12 And a to d are as defined in claim 1.
5. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
6. The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
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in the compound, D n Represents that n number of hydrogens are replaced with deuterium; and n represents an integer of 1 to 44.
7. An organic electroluminescent compound represented by the following formula 1:
in the formula (1) of the present invention,
R 1 to R 8 Each 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) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L 1 -Ar 1 The method comprises the steps of carrying out a first treatment on the surface of the Or may be linked to one or more adjacent substituents to form one or more rings;
provided that R 1 To R 8 At least one of them represents-L 1 -Ar 1 ；
L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;
Ar 1 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group, or-N- (R') (R "); and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
8. The organic electroluminescent compound according to claim 7, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
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9. an organic electroluminescent device comprising a plurality of host materials according to claim 1.
10. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 7.
11. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 7.
CN202310412150.2A 2022-04-27 2023-04-18 Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Pending CN116947847A (en)

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