CN116496282A - Heterocyclic compound and application thereof - Google Patents

Heterocyclic compound and application thereof Download PDF

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Publication number
CN116496282A
CN116496282A CN202310363250.0A CN202310363250A CN116496282A CN 116496282 A CN116496282 A CN 116496282A CN 202310363250 A CN202310363250 A CN 202310363250A CN 116496282 A CN116496282 A CN 116496282A
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substituted
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heterocyclic compound
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曹建华
张海威
王志杰
张九敏
何连贞
董梁
申旭
梁红红
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof. The structural formula of the heterocyclic compound is shown in a formula (I); the compound shown in the formula (I) provided by the invention has two imidazole structures. The compound is applied to an organic electroluminescent element, so that the driving voltage can be obviously reduced, the luminous efficiency can be improved, and the service life can be prolonged;

Description

Heterocyclic compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof in an organic light-emitting element.
Background
In general, an organic light emitting phenomenon refers to a phenomenon that emits light when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer; when the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, the organic electroluminescent display technology has tended to mature, and some products have entered the market, but in the industrialization process, many problems still remain to be solved. In particular, various organic materials for manufacturing elements, which have carrier injection and transport properties, material electroluminescent properties, service life, color purity, matching between various materials and between various electrodes, and the like, have not been solved; in particular, as the materials applied to the electron injection layer and the transport layer, as the earliest reports concerning the electron transport material, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and imidazolyl groups described in CN107573328A, CN107556310A, CN113801066A, CN113429395A, CN113429348A, CN114560872a and the like, which are typical materials for the electron transport layer, contain N-phenylbenzimidazole groups in the structure, and have not only the ability to transport electrons but also the function of blocking holes crossing the light emitting layer, but have a problem of low thermal stability when applied to practical devices.
In order to overcome the above-described problems, there is a continuing need for the development of a more stable and effective substance that can be used as an electron injection and transport substance in an organic electroluminescent element, in order to further improve the characteristics of the organic electroluminescent element.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a heterocyclic compound which can improve the thermal stability of materials and the capability of transporting carriers, and an organic electroluminescent element prepared by the heterocyclic compound can obviously reduce driving voltage, improve luminous efficiency and prolong service life; it is a further object of the present invention to provide the use of the compounds.
Specifically, the invention provides the following technical scheme:
the invention provides a heterocyclic compound, the structural formula of which is shown as the formula (I):
wherein,,
L 1 、L 2 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
X 1 and X 2 、X 3 And X 4 Represents a group of the formula (II);
"≡" indicates the adjacent group X in formula (I) 1 And X 2 、X 3 And X 4 ；
G represents O, S, SO, SO 2 、Se、CR 3 R 4 、SiR 3 R 4 Or NR (NR) 5 ；
Selected from hydrogen, phenyl, biphenyl or pyridyl;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 1 -C 40 Alkoxy, substituted or unsubstituted C 2 -C 40 Alkenyl, substituted or unsubstituted C 1 -C 40 Alkylthio, substituted or unsubstituted C 1 -C 40 Alkoxy, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 1 -C 40 Alkyl sulfoxide group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; any two or more substituents adjacent to each other may be optionally joined or fused to form a substituted or unsubstituted ring;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted and unsubstitutedC of (2) 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group.
In the present invention, the term "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, which is formed by bonding adjacent groups to each other. The condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocyclic ring, a condensed aromatic heterocyclic ring, or a combination thereof.
The heterocyclic compound according to the present invention is represented by the above formula (I), wherein the heterocyclic ring comprising dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, etc. is bonded to imidazole comprising formula (II) by a single bond, arylene, heteroarylene L 1 、L 2 And are combined to form a basic framework. The compound represented by the formula (I) of the present invention is electrochemically stable, has excellent electron mobility, has a high glass transition temperature, and has excellent thermal stability, as compared with conventionally known heterocyclic structures such as dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and the like. Thus, the heterocyclic compound of the present invention is excellent in electron transporting ability and light emitting property, and therefore can be used as a material for any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a hole blocking layer of an organic electroluminescent element. The material that can be used as any one of the light-emitting layer, the electron-transporting layer, and the electron-transporting auxiliary layer that is laminated in one step on the electron-transporting layer is preferable, and the material that can be used as the electron-transporting layer or the electron-transporting auxiliary layer is more preferable.
Specifically, the compound represented by the formula (I) of the present invention has a higher electron-transporting ability and can exhibit a relatively high luminous efficiency and a high glass transition temperature, compared with a heterocyclic ring such as dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, etc., which has a weak electron-withdrawing group, by a heterocyclic compound containing two imidazoles. Thus, when the heterocyclic compound represented by the formula (I) of the present invention is used for an organic electroluminescent element, not only can the thermal stability, carrier transporting ability, electron transporting ability and light emitting ability be excellent, but also the driving voltage of the element can be reduced, the efficiency and lifetime can be improved, and as a material for a latest electron transporting layer, an excellent efficiency increase due to a triplet-triplet amyl fusion effect can be exhibited due to a high triplet energy level.
In addition, the heterocyclic compound of formula (I) of the present invention is obtained by introducing a plurality of substituents R into the basic skeleton 1 、R 2 And Ar is a group 1 、Ar 2 The HOMO and LUMO energy levels are adjusted according to the kind of substituent, and thus a wide band gap can be provided, and the organic electroluminescent element using such a compound can exhibit the highest electron transport property.
In addition, the heterocyclic compound represented by the formula (I) of the present invention is obtained by introducing various substituents L into the above basic skeleton 1 、L 2 And Ar is a group 1 、Ar 2 In particular aryl and/or heteroaryl groups, the molecular weight of the compounds is significantly increased, so that the glass transition temperature is increased, and thus the compounds have higher thermal stability than the conventional luminescent materials, such as phenanthridine. Therefore, the performance and lifetime characteristics of the organic electroluminescent element comprising the compound according to the present invention can be greatly improved. The organic electroluminescent element thus improved in performance and lifetime characteristics can eventually maximize the performance of the full-color organic light-emitting panel.
The heterocyclic compound represented by the formula (I) of the present invention is preferably selected from the group consisting of:
wherein Ar is 1 、Ar 2 、Ar 3 、Ar 4 、L 1 、IL 2 、G、R 1 、R 2 The meaning of (2) is the same as defined above.
Preferably, the R 1 、R 2 、R 3 、R 4 Each independently is hydrogen, deuterium, methyl, substituted or unsubstituted Phenyl, substituted or unsubstituted fluorenyl.
According to an embodiment of the invention, the R 1 、R 2 Selected from hydrogen or deuterium.
According to an embodiment of the invention, the R 3 、R 4 、R 5 Each independently selected from the group consisting of hydrogen, deuterium, methyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, fluorenyl, dibenzofuran, or dibenzothiophene.
Aryl groups in the sense of the present invention contain 6 to 60 carbon atoms, heteroaryl groups contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. In this case, two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, or may further include a condensed form with the aryl group. As non-limiting examples of such heteroaryl groups, six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, and the like can be cited; polycyclic rings such as phenoxazolyl, indolizinyl, indolyl, purinyl, quinolinyl, benzothiazolyl, carbazolyl, and the like; 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, and the like.
Further, the aryl, heteroaryl or heteroaryl group is preferably selected from the group consisting of phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,a group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, ij]Naphtho [2,1,8-cde]Azulene, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzeneAnd is selected from the group consisting of a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, and a benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthamidinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl phenazinyl, phenoxazinyl, phenothiazinyl, fluororubenyl, naphthyridinyl, azacarbazolyl, benzocarboline, carboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, naphthyridinyl, quinazolinyl, and benzothiadiazolyl or combinations thereof.
According to an embodiment of the invention, the Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 5 Selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,Radicals, perylene radicals, fluoranthryl radicals, naphthacene radicals, pentacene radicals, benzopyrene radicals, biphenyl radicals, terphenyl radicals, trimeric radicalsPhenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo [ g, ij]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthaimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorozinyl, naphthyridinyl, azacarbazolyl, benzocarboline, carboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, naphthyridinyl, quinazolinyl, benzothiadiazolyl, or combinations thereof.
In the heterocyclic compound of formula (I) of the present invention, L 1 、L 2 To be used inComprising the heterocyclic skeleton containing two imidazoles and Ar 1 、Ar 2 The functional groups attached may be selected from the group consisting of single bonds, C 6 -C 60 Arylene and C of (2) 2 -C 60 A group of heteroarylenes. In this case, preferably, the L 1 、L 2 Each independently selected from a single bond or from the group consisting of groups III-1 to III-23:
wherein the dotted line represents the linking site of the group, and the binding site of the groups represented by the above formulas III-1 to III-23 is not limited, and may be any of ortho-, meta-, and para-ones. L as described above 1 、L 2 Can be independently selected from deuterium, halogen atom, nitrile group, C 1 -C 40 Alkyl, C 6 -C 60 Aryl and C 2 -C 60 When the substituent is plural, it is preferable that the plural substituents are the same or different from each other.
In the present invention, the term "substituted or unsubstituted" means that the compound is selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, and C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Cycloalkyl, C 3 -C 40 Cycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Aryl sulfide group and C 2 -C 60 More than 1 substituent in the heterocyclic aryl group is substituted or unsubstituted, or a substituent which is formed by connecting more than 2 substituents in the above exemplified substituents is substituted or unsubstituted.
Alkyl radicals in the sense of the present invention contain 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH 2 The radicals can also beSubstituted straight chain alkyl or branched alkyl; alkenyl or alkynyl groups contain at least two carbon atoms, and alkyl, alkenyl or alkynyl groups are preferably considered to mean, by way of non-limiting example, the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
Alkoxy is preferably an alkoxy group having 1 to 40 carbon atoms, which is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy.
Heteroalkyl is preferably an alkyl radical having from 1 to 40 carbon atoms, meaning in which the hydrogen atom or-CH is alone 2 Groups substituted with oxygen, sulfur, halogen atoms, as non-limiting examples, alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butylenethio, butyleneoxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene thio, acetylenyloxy, acetylenylthio, propynyloxy, butynylthio, pentynyloxy, pentynylthio, hexyloxy, hexylynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The heterocycloalkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a atomic number of 3 to 40. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine, and the like are given.
The condensed ring aryl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a combination of two or more rings. In this case, two or more rings may be attached to each other singly or in a condensed form. As non-limiting examples thereof, there may be mentioned phenanthryl, anthracyl, fluoranthracyl, pyrenyl, triphenylenyl, perylenyl,A base, etc.
As the arylamine group used in the present invention, an arylamine group refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylamine group, there are a diphenylamino group, an N-phenyl-1-naphthylamine group, an N- (1-naphthyl) -2-naphthylamine group and the like. The heteroarylamino group means an amine substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms, and as non-limiting examples of the heteroarylamino group, there are N-phenylpyridine-3-amino, N- ([ 1,1 '-biphenyl ] -4-yl) dibenzo [ b, d ] furan-2-amino, N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluorene-2-amino, and the like.
Alkoxy as used in the present invention means RO - The monovalent functional group represented by R is an alkyl group having 1 to 40 carbon atoms, and may have a linear, branched or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, and n-propoxyRadical, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, cyclopentoxy, cyclohexyloxy, and the like.
Aryloxy as used herein refers to R' O - The monovalent functional group represented by R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Arylsilyl refers to silyl groups substituted with aryl groups having from 6 to 60 carbon atoms.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylphosphorus group, there are diphenylphosphorus group, bis (4-trimethylsilylbenzene) phosphorus group and the like. The phosphorus atom of the aryl phosphorus oxide group is the diaryl phosphorus group is oxidized to the highest valence state.
The arylboron group used in the present invention means a diarylboroyl group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylboron group, there are diphenyl boron group, bis (2, 4, 6-trimethylbenzene) boron group and the like. The alkylboryl group means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
Preferably, the heterocyclic compound is selected from the group consisting of compounds represented by the following formulas J475-J543:
wherein T is selected from O, S, SO, se or NPh; ph represents phenyl.
The invention also provides an organic electroluminescent material, which comprises the heterocyclic compound; the organic electroluminescent material comprising the heterocyclic compound of the present invention has a carrier transporting ability.
The invention also provides application of the heterocyclic compound in preparation of an organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer includes the heterocyclic compound described above.
The organic electroluminescent element comprises a cathode, an anode and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent device described herein may comprise one light emitting layer, or it may comprise a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the heterocyclic compound of the present invention according to the present invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the electron blocking layer or hole transport layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner generally used according to the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method and/or at least one layer being applied by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer being applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to heterocyclic compounds comprising at least one of the above-indicated invention. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, it may be preferable to contain other compounds in addition to the heterocyclic compound. Treatment of the heterocyclic compounds of the present invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of the formulations of the compounds of the present invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or mixtures of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
The invention also provides a consumer product comprising the organic electroluminescent element.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The beneficial effects obtained by the invention are as follows:
the heterocyclic compound represented by formula (I) provided by the invention can be applied to an organic layer of an organic electroluminescent element due to excellent electron mobility, thermal stability and luminescence characteristics. In particular, when the heterocyclic compound represented by the formula (I) of the present invention is used for an electron transport layer and an electron transport auxiliary layer, an organic electroluminescent element having a lower driving voltage, higher efficiency and longer lifetime than conventional electron transport materials can be produced, and further, a full-color display panel having improved performance and lifetime can be produced.
Drawings
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, an organic light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping, or cross-overlapping, or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of the device 100.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
In the description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower", etc. are based on the orientation or positional relationship shown in the drawings, are merely for convenience of description and to simplify the description, and are not indicative or implying that the apparatus or elements in question must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the present invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the examples below, unless otherwise specified, are all commercially available, and the percentages, such as the percentages without otherwise specified, are all mass percentages.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
Power efficiency: NEWPORT 1931-C test was used.
Example 1
A process for preparing compound J475, for example, t=s, comprising the steps of:
the first step: preparation of intermediate Int-1
Under the protection of nitrogen, 40.0mmol of phenylacetylene (reactant 2), 20.0mmol of 2, 5-dibromo-3, 4-dicyanothiophene (reactant 1), 4.0mmol of cuprous iodide and 4.0mmol of PdCl 2 (PPh 3 ) 2 Mixing 8.0mmol of triphenylphosphine and 80mL of triethylamine, heating to reflux, stirring, reacting for 15 hours, cooling to room temperature, concentrating under reduced pressure, drying, and separating and purifying by a silica gel column to obtain the compound Int-1 as a yellow solid with the yield of 86%.
And a second step of: preparation of intermediate Int-2
Under the protection of nitrogen, mixing 20.0mmol of Int-1 prepared in the previous step, 80.0mmol of nitromethane, 80.0mmol of potassium hydroxide and 60mL of DMSO, heating to 110 ℃, stirring for reaction for 45 minutes, cooling to room temperature, pouring the reaction solution into 150mL of ice water, filtering, washing a filter cake with water, and recrystallizing with methanol to obtain a compound Int-2 as a yellow solid with a yield of 85%.
And a third step of: preparation of intermediate Int-3
20.0mmol of Int-2 prepared in the previous step is dissolved in 100mL of dichloromethane, 60.0mmol of pyridine is added, the temperature is reduced to 0 ℃, 42.0mmol of benzoyl chloride (reactant 3) is added dropwise, the temperature is raised to room temperature, stirring is carried out for 15 hours, 50mL of diluted hydrochloric acid is added, an organic phase is separated, an aqueous phase is extracted by dichloromethane, an organic phase is collected, water washing, drying, filtration and decompression concentration and drying of filtrate are carried out, and compound Int-3 is obtained as a yellow solid with the yield of 95%.
Fourth step: preparation of intermediate Int-4
20.0mmol of Int-3 prepared in the previous step and 100mL of ethanol are mixed, 0.2g of 10% palladium/carbon is added, hydrogen is introduced under normal pressure, stirring reaction is carried out for 15 hours at room temperature, filtration is carried out, and the filtrate is concentrated and dried under reduced pressure, thus obtaining the compound Int-4 as a yellow solid with the yield of 100%.
Fifth step: preparation of intermediate Int-5
Under the protection of nitrogen, 20.0mmol of Int-4 prepared in the previous step, 40.0mmol of bromobenzene (reactant 4), 60.0mmol of sodium tert-butoxide and 100mL of toluene are mixed, and 0.2mmol of Pa is added 2 (dba) 3 And 0.4mmol Xantphos, raise the temperature to 90 ℃ and stir for reaction for 15 hours, reduce the temperature to room temperature, add 50mL water, filter, wash the filter cake with water and ethanol to obtain compound Int-5 as yellow solid with 80% yield.
Sixth step: preparation of Compound J475
Mixing 20.0mmol of Int-5 prepared in the previous step, 2.0mmol of p-toluenesulfonic acid and 100mL of toluene under the protection of nitrogen, heating, refluxing and stirring for reaction for 12 hours, separating water generated by the reaction through a water separator, cooling to room temperature, concentrating and drying under reduced pressure, and separating and purifying by a silica gel column to obtain a compound J475, T=S, white solid, yield 87%, MS (TOF) m/z:721.2364; 1 HNMR(δ、CDCl 3 )：8.07～8.02(4H,m)；7.98(2H,s)；7.86～7.82(4H,m)；7.62～7.54(8H,m)；7.52～7.47(6H,m)；7.43～7.36(6H,m)；7.33～7.28(2H,m)。
t=o, white solid, yield 90%, MS (TOF) m/z:705.2588; 1 HNMR(δ、CDCl 3 )：8.26～8.22(4H,m)；8.15(2H,s)；8.07～8.02(4H,m)；7.65～7.61(4H,m)；7.58～7.54(4H,m)；7.51～7.46(6H,m)；7.43～7.38(6H,m)；7.35～7.31(2H,m)。
T=se, white solid, yield 82%, MS (TOF) m/z:769.1886; 1 HNMR(δ、CDCl 3 )：8.36～8.34(2H,t)；8.07～8.01(4H,m)；7.77～7.73(4H,m)；7.63～7.53(8H,m)；7.50～7.43(6H,m)；7.41～7.36(6H,m)；7.33～7.30(2H,m)。
t=nph, white solid, yield 85%, MS (TOF) m/z:780.3063; 1 HNMR(δ、CDCl 3 )：8.21(2H,s)；8.07～8.02(4H,m)；7.98～7.94(4H,m)；7.69～7.62(6H,m)；7.60～7.54(6H,m)；7.52～7.46(6H,m)；7.43～7.36(6H,m)；7.33～7.27(3H,m)。
referring to the above-described similar synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
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Example 2
A process for the preparation of compound J532 comprising the steps of:
the first step: preparation of intermediate Int-6
Referring to the synthesis method of the first step of example 1, intermediate Int-6 is prepared by substituting 2, 5-dibromo-3, 4-dicyanothiophene in the first step of example 1 with 2, 5-dibromo-3, 4-dicyanofuran or 2, 5-dibromo-3, 4-dicyano-1-phenylpyrrole, etc., substituting phenylacetylene with 2-ethynyl-1-phenylbenzo [ d ] imidazole, and the yield is 80% -85%.
And a second step of: preparation of intermediate Int-7
Referring to the synthesis method of the second step of example 1, only Int-1 in the second step of example 1 is replaced by Int-6 to prepare intermediate Int-7, and the yield is 85% -90%.
And a third step of: preparation of intermediate Int-8
Under the protection of nitrogen, 10.0mmol of intermediate Int-7, 10.0mmol of o-bromoiodobenzene, 25.0mmol of cesium carbonate and 0.01mmol of Pd 2 (dba) 3 The method comprises the steps of reacting a catalyst, 0.02mmol Xantphos and 100mL of toluene at a temperature of 100 ℃ under stirring for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating and drying filtrate under reduced pressure, and separating and purifying the filtrate by using a silica gel column to obtain a compound Int-8 as a yellow solid, wherein the yield is 80% -85%.
Fourth step: preparation of intermediate Int-9
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Referring to the synthesis method of the fourth step of example 1, only Int-3 in the fourth step of example 1 was replaced with Int-8 to prepare intermediate Int-9 in 100% yield.
Fifth step: preparation of intermediate Int-10
Referring to the synthesis method of the third step of example 1, only Int-2 in the third step of example 1 is replaced by Int-9 to prepare an intermediate Int-10, and the yield is 90% -95%.
Sixth step: preparation of Compound J532
Referring to the synthesis method of the sixth step of example 1, compound J532 was prepared by replacing only Int-5 in the sixth step of example 1 with Int-10;
t=s; yellow solid, 89% yield, MS (MALDI-TOF): m/z=875.2721 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.44(2H,s)；8.21～8.10(8H,m)；8.78～8.69(4H,m)；7.61～7.52(8H,m)；7.49～8.43(6H,m)；7.37～7.32(2H,m)；7.26～7.18(4H,m)。
T=o; yellow solid, yield 87%, MS (MALDI-TOF): m/z=859.2868 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.54(2H,s)；8.23～8.12(8H,m)；7.79～7.70(4H,m)；7.61～7.52(8H,m)；7.49～8.43(6H,m)；7.37～7.32(2H,m)；7.26～7.18(4H,m)。
T=se; yellow solid, yield 81%, MS (MALDI-TOF): m/z=923.2164 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.76(2H,s)；8.23～8.12(8H,m)；7.78～7.68(4H,m)；7.61～7.52(8H,m)；7.49～8.43(6H,m)；7.37～7.32(2H,m)；7.26～7.18(4H,m)。
T=nph; yellow solid, yield 85%, MS (MALDI-TOF): m/z=934.3342 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.76(2H,s)；8.23～8.19(6H,m)；8.16～8.12(2H,m)；7.78～7.66(6H,m)；7.61～7.52(8H,m)；7.50～7.42(8H,m)；7.37～7.29(3H,m)；7.26～7.18(4H,m)。
Referring to the above-described similar synthetic method, the following compounds shown in table 2 were prepared:
TABLE 2
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In the above embodiments, T is selected from O, S, se or NPh; ph represents phenyl.
Example 3
Preparation of compound J536:
10.0mmol of J506 (t=s) and 40mL of glacial acetic acid are mixed, 1.0mmol of ammonium molybdate and 5mL of 30% hydrogen peroxide are added, the mixture is stirred at room temperature for reaction for 15 hours, the mixture is concentrated and dried under reduced pressure, 50mL of saturated aqueous sodium bicarbonate solution is added, the mixture is filtered, the filter cake is washed with water and separated and purified by a silica gel column, and the compound J536 is obtained as a white solid with the yield of 98%, MS (TOF) m/z:1083.3417; 1 HNMR(δ、CDCl 3 )：8.35(2H,s)；8.09～8.01(10H,m)；7.64～7.55(8H,m)；7.51～7.43(12H,m)；7.37～7.25(14H,m)。
Referring to the above-described similar synthetic method, the following compounds shown in table 3 were prepared:
TABLE 3 Table 3
Reactants Product(s) Yield is good
J505(T＝S) J535 97％
J507(T＝S) J537 96％
J508(T＝S) J538 95％
J533(T＝S) J539 98％
J534(T＝S) J540 97％
J530(T＝S) J541 96％
J510(T＝S) J542 96％
J532(T＝S) J543 97％
Example 4
As shown in fig. 1, the OLED element of the present embodiment is a top emission light element, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, and a cathode 110 disposed on the electron injection layer 109 and a capping layer 111 disposed on the cathode, wherein the method for preparing the OLED element excluding the hole blocking layer 107 includes the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, depositing metallic silver as an anode layer on the ITO film, the thickness of the deposited film beingContinuing to vapor deposit the compounds HI01 and F4TCNQ as hole injection layers respectively, wherein F4TCNQ is 3% of HI01 by mass, and the vapor deposition film thickness is +.>/>
3) Continuously evaporating compound HTM as hole transport layer on the hole injection layer to obtain an evaporating film with a thickness of
4) Continuously evaporating compound EBL as electron blocking layer on the hole transport layer to obtain an evaporating film thickness of
5) Continuously evaporating compound RH018 as main material and RD011 as doping material on the electron blocking layer, wherein RD011 is 3% of compound RH018 by mass, and the film thickness of the organic light emitting layer obtained by evaporation is as the organic light emitting layer of the element
6) Continuously evaporating a layer of LiQ and the compound of the formula (I) as an electron transport layer of the element on the organic light-emitting layer, wherein the compound of the formula (I) is 50% of the mass of the LiQ, and the evaporation film thickness is
7) Continuously evaporating a LiF layer on the electron transport layer to form an electron injection layer with an evaporating film thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer of the element, wherein the mass ratio of magnesium to silver is 1:10, and the film thickness of the evaporated film is
9) Evaporating CPD layer as CPL layer of the device on the transparent cathode layer to obtain an evaporated film thickness ofThe OLED element provided by the invention is obtained.
The structure of the compound used in example 4 above is as follows:
example 5
An organic electroluminescent device 200, the structure of which is shown in fig. 2, comprises a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first luminescent layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second luminescent layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213.
Comparative example 1
By following a procedure similar to that of example 4, substituting the compound of formula (I) according to the invention in step 6) with E01 gives comparative element 1;
the organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent elements prepared in examples 4 and 5 and comparative example 1 were measured using a digital source meter and a luminance meter. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; LT95% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 950cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 4 are relative data compared to comparative element 1.
TABLE 4 Table 4
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As can be seen from Table 4, the device prepared from the heterocyclic compound of the present invention has a lower driving voltage than E01 under the same brightness, a significantly improved current efficiency up to as much as 1.26 times that of the comparative device, and a better improvement in LT95% lifetime of the device, indicating that the heterocyclic compound of the present invention is an excellent electron transport layer material.
The compound E01 of comparative example 1 is different from the compound of the present invention in that the plane conjugation ability is weak after three imidazole groups are introduced into the phenyl group, resulting in high voltage and low efficiency. The heterocyclic compound of the invention has strong conjugation capability after two imidazole groups are introduced on rings such as dibenzofuran, dibenzothiophene and the like, and the plane is increased, so that the heterocyclic compound has more excellent performance in molecular film formation and charge transmission, and the charge transmission in the element is more balanced, thereby obviously improving the element performance.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (10)

1. A heterocyclic compound is characterized in that the structural formula is shown in a formula (I):
wherein,,
L 1 、L 2 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
X 1 and X 2 、X 3 And X 4 Represents a group of the formula (II);
"≡" indicates the adjacent group X in formula (I) 1 And X 2 、X 3 And X 4 ；
G represents O, S, SO, SO 2 、Se、CR 3 R 4 、SiR 3 R 4 Or NR (NR) 5 ；
Selected from hydrogen, phenyl, biphenyl or pyridyl;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 1 -C 40 Alkoxy, substituted or unsubstituted C 2 -C 40 Alkenyl, substituted or unsubstituted C 1 -C 40 Alkylthio, substituted or unsubstituted C 1 -C 40 Alkoxy, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 1 -C 40 Alkyl sulfoxide group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; any two or more substituents adjacent to each other may be optionally joined or fused to form a substituted or unsubstituted ring;
Ar 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group.
2. The heterocyclic compound of claim 1, wherein the heterocyclic compound is selected from the group consisting of:
wherein Ar is 1 、Ar 2 、Ar 3 、Ar 4 、L 1 、L 2 、G、R 1 、R 2 Is as defined in claim 1.
3. The heterocyclic compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 Each independently is hydrogen, deuterium, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl;
Ar 1 、Ar 2 、Ar 3 、Ar 4 、R 5 selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, ij ]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthamidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolylA group, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxazolyl, phenanthroxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-naphthyridinyl, 2, 7-naphthyridinyl, 2, 3-naphthyridinyl, 1, 6-naphthyridinyl, 1, 8-naphthyridinyl, 4,5,9, 10-tetraazaperylen, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorocyclyl, naphthyridinyl, azacarbazolyl benzocarboline group, carboline group, phenanthroline group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazole group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 4-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl group, 1,2,3, 5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, quinazolinyl group, benzothiadiazolyl group, or groups derived from combinations of these systems.
4. The heterocyclic compound according to claim 1, wherein R 1 、R 2 Selected from hydrogen or deuterium;
R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, methyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, fluorenyl, dibenzofuran, or dibenzothiophene.
5. The heterocyclic compound according to claim 1, wherein L 1 、L 2 Each independently selected from a single bond or from the group consisting of groups III-1 to III-23:
wherein the dotted line represents the attachment site of the group.
6. The heterocyclic compound according to any one of claims 1 to 5, wherein the heterocyclic compound is selected from compounds represented by the following formulae J475 to J543:
wherein T is selected from O, S, SO, se or NPh; ph represents phenyl.
7. Use of the heterocyclic compound according to any one of claims 1 to 6 for producing an organic electroluminescent element.
8. An organic electroluminescent element, characterized in that it comprises: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; a material of at least one of the organic layer or the capping layer includes the heterocyclic compound according to any one of claims 1 to 6.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer; the light-emitting layer, electron transporting layer, or hole blocking layer comprising the heterocyclic compound according to any one of claims 1 to 6.
10. A consumer product comprising the organic electroluminescent element of claim 8.
CN202310363250.0A 2023-04-06 2023-04-06 Heterocyclic compound and application thereof Pending CN116496282A (en)

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