CN116693550A - Oxazole derivative and application thereof - Google Patents

Oxazole derivative and application thereof Download PDF

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Publication number
CN116693550A
CN116693550A CN202310671951.0A CN202310671951A CN116693550A CN 116693550 A CN116693550 A CN 116693550A CN 202310671951 A CN202310671951 A CN 202310671951A CN 116693550 A CN116693550 A CN 116693550A
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substituted
unsubstituted
group
layer
aryl
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曹建华
郭晓慧
王振宇
李利铮
王志杰
张九敏
何连贞
董梁
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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 belongs to the technical field of organic electroluminescence, and particularly relates to an oxazole derivative and application thereof in an organic electroluminescent material and a light-emitting element. When the oxazole derivative of the present invention is used as a material for a light-emitting layer in an organic electroluminescent element, the oxazole derivative has higher carrier mobility than conventional materials, high internal quantum efficiency, excellent amorphism, and stable thin film state, and therefore the organic electroluminescent element can realize high efficiency, low driving voltage, and long life.

Description

Oxazole derivative and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an oxazole derivative and application thereof in an organic electroluminescent material and a light-emitting element.
Background
Organic Light Emitting Diodes (OLEDs), also known as organic electroluminescent devices, are a technology in which an organic material emits light by carrier injection and recombination under the action of an electric field, and it is capable of converting electric energy into light energy through the organic light emitting material, including passive-driven OLEDs (PMOLEDs) and active-driven OLEDs (AMOLEDs). OLEDs are a new generation of display technology following Cathode Ray Tubes (CRTs), liquid Crystal Displays (LCDs), known as fantasy display technology. OLEDs also show good development prospects in communication terminals, military fields and flexible displays. However, the development time of OLED is still short compared with other display technologies, so that the theoretical system related to the organic electroluminescent display technology is still not fully systematic, and the field is also full of opportunities and challenges, such as poor device efficiency, higher manufacturing requirements and cost, short device lifetime, poor stability, and the like, which still remain to be solved.
One of the key factors affecting the efficiency of an OLED device is the injection and recombination process of carriers in the device, and research shows that the efficiency of the device can be effectively improved by balancing the carriers. However, the balance of carriers is difficult to control, which affects exciton recombination luminescence of the light-emitting layer, resulting in lower device efficiency. At present, the hole transmission rate in an OLED device is far higher than the electron transmission rate, so that the development of an electron transmission material with high transmission rate is an effective way for improving the luminous efficiency of the device, and has important research significance. Some common electron transport materials, such as metal organic complexes, have good film forming property and excellent electron transport property; the quinoline material has low reduction potential value, good mechanical property and high thermal stability; the triazine compound has the advantages of excellent heat resistance, higher electron affinity potential energy and the like; the oxadiazole molecules have the advantages of excellent chemical stability, high electron transmission rate, capability of reducing starting voltage, good thermal stability and the like.
The structure of the oxazole is similar to that of the oxadiazole, and the oxazole has electron-deficient performance, but the electron-transporting materials of the oxazole are unusual, and the structure of the oxazole has not been paid attention to in the aspect of photoelectric materials. Before, the research discovers that the performance of the oxazole as the electron transport material can be researched by carrying out functional modification on the oxazole, so that the blind area of the oxazole as the electron transport material is filled, and a foundation is laid for future scientific research work.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides an oxazole derivative, an organic electroluminescent material, a light emitting element and a consumer product.
The first object of the present invention is to provide an oxazole derivative.
The second object of the present invention is to provide an organic electroluminescent material.
A third object of the present invention is to provide an organic electroluminescent element.
A fourth object of the present invention is to provide a consumer product.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an oxazole derivative has a structural general formula shown in formula (I):
wherein two adjacent W represent groups represented by formula (II);
z each independently represents CR 1 Or N; and two adjacent "≡" groups are indicated for two adjacent groups W in formula (I);
g represents S, se or NAr 3 ；
R 1 Each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Aryl silyl group, any adjacent two or more R 1 Optionally joined or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
Ar 1 、Ar 2 、Ar 3 each occurrence is independently selected from substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine groups.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 30 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like;
aryl groups in the sense of the present invention contain 6 to 50 carbon atoms, heteroaryl groups contain 2 to 50 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 simply attached to each otherOr in a condensed form, and further may contain a form condensed with an aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular groups selected from the following: 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, id]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, naphthamidinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracrooxazolyl, 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, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxazinyl Diazolyl, 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, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.
"halogen" or "halogen atom" as used herein means a member selected from fluorine, chlorine, bromine or iodine.
Further, the R 1 Each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstitutedA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, or formula (III);
Ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenylA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a formula (III);
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
Ar 4 、Ar 5 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenyl A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group;
the dotted line represents the attachment site of the group.
Further, the Ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of substituted and unsubstitutedA substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted carbazolyl, or a group of formula (IV);
L 2 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
het is selected from C 2 ～C 50 Heteroaryl groups;
the dotted line represents the attachment site of the group.
Heteroalkyl in the sense of the present invention means a hydrogen atom or-CH on an alkyl radical 2 Substituted with at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like. Haloalkyl refers to the partial substitution or total substitution of a hydrogen atom on an alkyl group with a halogen, and as non-limiting examples there are fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl and the like.
Alkenyl or alkynyl groups useful in the present invention contain at least two carbon atoms, and are preferably considered to mean, by way of non-limiting example, the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.
Alkoxy, alkylthio, preferably alkoxy or alkylthio having 1 to 30 carbon atoms, as used in the present invention is understood 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, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
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 radical may be replaced by N, O or S to form heterocycloalkyl, heterocycloalkenyl, e.g. one of the cyclopentyl groups-CH 2 -the radical is replaced by O to form one of the groups-CH in the tetrahydrofuranyl, cyclohexyl 2 -the group is replaced by O to form tetrahydropyranyl, etc.; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Aryloxy as used herein refers to R' O - The monovalent functional group represented by R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
Arylthio as used herein means R "S - The monovalent functional group represented by R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such arylthio groups, phenylthio, naphthylthio, biphenylthio and the like are mentioned.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 30 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. Aryl silicon group refers to alkyl silicon group substituted with at least one aryl group having 6 to 50 carbon atoms, and examples of the alkyl silicon group include phenyl dimethyl silicon group, naphthyl dimethyl silicon group, phenyl diethyl silicon group, diphenyl methyl silicon group, diphenyl ethyl silicon group, triphenyl silicon group, and the like.
"alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylborocarbonyl", "alkylborocarbonyl" in the sense of the present invention means a substituted carbonyl (-COR) wherein R is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboronyl, alkylboronyl.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 50 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 50 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 30 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
The arylalkyl group according to the present invention means an alkyl group in which at least one hydrogen atom of a straight or branched saturated hydrocarbon having from 1 to 30 carbon atoms is substituted with an aryl group having from 6 to 50 carbon atoms, and as a non-limiting example, phenylmethyl group, diphenylmethyl group, triphenylmethyl group, 2-phenylethyl group, 3-phenylpropyl group and the like can be mentioned.
Alkylaryl according to the present invention refers to an aryl group in which at least one hydrogen atom of the aryl group having from 6 to 50 carbon atoms is substituted with a straight or branched saturated hydrocarbon having from 1 to 30 carbon atoms, and as a non-limiting example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl and the like can be mentioned.
Preferably, the heteroaryl is selected from the group consisting of groups II-1 to II-13:
wherein,,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 representation O, S or NAr ’ ；
Ar' is selected from C 1 ～C 30 Alkyl, C of (2) 1 ～C 30 Heteroalkyl of (C) 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 50 Aryl, substituted or unsubstituted C 6 -C 50 Condensed ring aryl, substituted or unsubstituted C 6 -C 50 Arylamine groups, or substituted or unsubstituted C 2 -C 50 Heteroaryl groups; preferably Ar' is methyl,Ethyl, phenyl, biphenyl or naphthyl;
representing the attachment site of the group.
Further, het is selected from the group consisting of groups of formulae II-1 to II-13.
The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted condensed aryl, substituted arylene, substituted heteroarylene described herein are each independently selected from at least one of the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C 1 -C 30 Alkyl, C 1 -C 30 Haloalkyl, C 2 -C 30 Alkenyl, C 2 -C 30 Alkynyl, C 1 -C 30 Alkoxy, C 1 -C 30 Alkylthio, C 3 -C 30 Cycloalkyl, C 3 -C 30 Cycloalkenyl, 3-to 7-membered heterocycloalkyl, C 6 -C 50 Aryloxy, C 6 -C 50 Arylthio, unsubstituted or substituted by one or more C 6 -C 50 Aryl-substituted 3-to 30-membered heteroaryl, unsubstituted or deuterated, one or more C 1 -C 30 C substituted with at least one of an alkyl group and one or more 3-to 30-membered heteroaryl groups 6 -C 50 Aryl, tris (C) 1 -C 30 ) Alkylsilyl, tri (C) 6 -C 50 ) Aryl silicon based, di (C) 1 -C 30 ) Alkyl (C) 6 -C 50 ) Aryl silicon base, C 1 -C 30 Alkyldi (C) 6 -C 50 ) Aryl silicon base, C 1 -C 30 Alkylcarbonyl, C 1 -C 30 Alkoxycarbonyl group, C 6 -C 50 Arylcarbonyl, di (C) 6 -C 50 ) Arylborocarbonyl groups of di (C) 1 -C 30 ) Alkyl boron carbonyl, C 1 -C 30 Alkyl (C) 6 -C 50 ) Arylborocarbonyl, C 6 -C 50 Aryl (C) 1 -C 30 ) Alkyl, C 1 -C 30 Of alkyl (C) 6 -C 50 ) Aryl groups.
Arylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 50 carbon atoms. As non-limiting examples thereof, there are phenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene and the like.
The heteroarylene or heteroarylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from a heteroarene having 2 to 50 carbon atoms. As non-limiting examples thereof, there are a pyridyl group, a quinolyl group, an isoquinolyl group, a carbolinyl group, a pyrimidyl group, a triazinyl group and the like.
The arylene, heteroarylene groups as described above are attached as divalent functional groups to Het or N, preferably the L 1 、L 2 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
wherein X is selected from O, S, se, CR ' R ', siR ' R ' or NAr ';
Z 11 、Z 12 、Z 13 、Z 14 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 30 Alkyl, C of (2) 2 -C 30 Alkenyl, C 2 -C 30 Alkynyl, C 1 -C 30 Alkoxy, C 3 -C 30 Is C 3 -C 30 Cyclic olefin group, substituted or unsubstituted C 6 -C 50 Aryl, substituted or unsubstituted C 6 -C 50 Aryloxy, substituted or unsubstitutedC 6 -C 50 Aryl sulfide group, or substituted or unsubstituted C 2 -C 50 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents an integer of 1 or 2;
r ', R' are each independently selected from C 1 -C 30 Alkyl, C of (2) 1 -C 30 Is optionally substituted C 6 -C 50 Aryl, substituted or unsubstituted C 6 -C 50 Arylamine groups, or substituted or unsubstituted C 2 -C 50 Heteroaryl, R' and R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
ar' is selected from C 1 -C 30 Alkyl, C of (2) 1 -C 30 Heteroalkyl of (C) 3 -C 30 Cycloalkyl, substituted or unsubstituted C 6 -C 50 Aryl, substituted or unsubstituted C 6 -C 50 Condensed ring aryl, substituted or unsubstituted C 6 -C 50 Arylamine groups, or substituted or unsubstituted C 2 -C 50 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Wherein the dotted line represents the attachment site of the group.
Preferably, X is selected from O or S.
Preferably, the L 1 、L 2 Each independently selected from a single bond or a group consisting of groups III-1 to III-15, III-25:
preferably, said Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from hydrogen, deuteriumFluorine, nitrile groups.
Further, the oxazole derivative is selected from one or more of the following structures E950-E1135:
wherein G is selected from S or NAr 3 ；
The Ar is as follows 3 Selected from the group consisting of:
as used herein, "combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, the alkyl and deuterium atoms can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
An organic electroluminescent material comprising the oxazole derivative.
The organic electroluminescent material may be constituted by using the oxazole derivative of the present invention alone or may contain other compounds at the same time.
The oxazole derivative of the present invention contained in the organic electroluminescent material of the present invention can be used as, but not limited to, a light emitting layer material, a carrier transporting layer material, a capping layer or a charge generating layer material.
An organic electroluminescent device comprising a first electrode, a second electrode, a capping layer and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer or capping layer comprises an oxazole derivative provided by the present invention.
The organic electroluminescent device 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. I.e. a plurality of luminescent compounds capable of emitting light are used in the luminescent layer. A system with three light emitting layers is preferred, 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 an oxazole derivative of the invention according to the invention.
Further, the organic electroluminescent device 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 hole injection 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 device according to the invention, in particular in the hole-transporting layer and the capping layer and in the electron-transporting layer, all materials can be used in the manner generally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
Furthermore, organic electroluminescent devices are preferred, which apply one or more layers by means of sublimation methods, wherein the sublimation is performed in a vacuum at 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 devices which apply one or more layers by means of an organic vapor deposition process 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 the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent devices are preferred in which one or more layers are produced from a solution, 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 the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula I. 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 an organic electroluminescent element comprising the oxazole derivative according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent device according to the invention, which applies at least one layer by means of a sublimation method and/or at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer from a solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferences as indicated above in relation to the organic electroluminescent device apply to the compounds of the invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires preparations of the compounds according to the 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-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl, 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 methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol, triethylene glycol, 1, 2-dimethyl benzene ether, 1-dimethyl-n-butyl ether, 1-dimethyl-butyl benzene, 1-dimethyl-n-butyl benzene, 1-dimethyl-butyl benzene, n-butyl benzene, dimethyl benzene, n-butyl benzene, dimethyl benzene, or a mixture of these solvents.
Further, the organic layer is selected from one or more of an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a charge generation layer.
Further, the electron transporting layer, light emitting layer, capping layer or charge generating layer comprises the oxazole derivative of the present invention.
Still further, the light-emitting layer comprises the oxazole derivative of the present invention.
Further, the light-emitting layer comprises a dopant and a light-emitting host, wherein the dopant comprises a material selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, and combinations thereof,In addition, various metal complexes, bisstyrylbenzene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, heterocyclic compounds having an indole ring as a partial structure of a condensed ring, heterocyclic compounds having a carbazole ring as a partial structure of a condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used. In addition, as a dopant material, other than this, it is also possible to use: pyrene derivative having pyrene skeleton in molecule, heterocyclic compound having indole ring as partial structure of condensed ring, heterocyclic compound having carbazole ring as partial structure of condensed ring Compounds, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, quinacridones, coumarins, rubrene, perylenes, their derivatives, benzopyran derivatives, indenofenanthrene derivatives, rhodamine derivatives, aminostyryl derivatives, and the like. These may be used alone, as a single layer formed by mixing with other materials, or as a laminated structure of layers formed alone, between layers formed by mixing, or between layers formed alone and layers formed by mixing.
In addition, phosphorescent emitters may also be used as dopants. As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used. Ir (ppy) may be used 3 Blue phosphorescent emitters such as green phosphorescent emitters, firpic, fir6 and Btp 2 Red phosphorescent emitters such as Ir (acac) and the like are preferably used as the host material in this case. As a host material (P-type material) having hole injection and transport properties, carbazole derivatives such as 4,4' -bis (N-Carbazolyl) Biphenyl (CBP), TCTA, and mCP can be used. As the electron-transporting host material (n-type material), p-bis (triphenylsilyl) benzene (UGH 2), 2',2"- (1, 3, 5-phenylene) -tris (1-phenyl-1H-benzimidazole) (TPBI), or the like can be used, and a high-performance light-emitting element can be produced.
In order to avoid concentration quenching, the phosphorescent light-emitting material is doped into the host material preferably by co-evaporation in a range of 1 to 10% by weight relative to the light-emitting layer.
As the light-emitting dopant, a material that emits delayed fluorescence, such as CDCB derivatives, e.g., PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, may be used.
Further, the light-emitting body comprises the oxazole derivative of the present invention.
Further, the mass ratio of the dopant to the light-emitting main body is 1:99-50:50.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Compared with the prior art, the invention has the beneficial effects that:
the oxazole derivative has novel rigid structures such as large-plane conjugated dibenzothiophene oxazole, carbazole oxazole and the like, and the compound represented by the general formula (I) has large mobility of (1) carriers; (2) high internal quantum efficiency; (3) stable film state; (4) The heat resistance is excellent, so that the material is suitable for use as a constituent material of a light-emitting layer of an organic electroluminescent element.
In the organic electroluminescent element using the oxazole derivative represented by the general formula (I) of the present invention as a host material for the light-emitting layer, a compound having higher carrier mobility than conventional materials, high internal quantum efficiency, excellent amorphism, and stable thin film state is used, so that high efficiency, low driving voltage, and long lifetime can be realized.
Further, in the present invention, the luminescent layer is formed by the oxazole derivative of the general formula (I), so that the high quantum efficiency performance and heat resistance of the compound can be utilized to the maximum extent, and the long-life organic electroluminescent element can be realized with higher efficiency.
In the present invention, an organic electroluminescent element using an oxazole derivative represented by the general formula (I) as a constituent material thereof in at least one of the light-emitting layers or the laminated film in which two or more light-emitting layers are arranged can be realized with high efficiency, low driving voltage, and long life because a compound having high carrier mobility, high internal quantum efficiency, excellent amorphism, and stable thin film state is used.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
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 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a 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
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid derivatives, can be synthesised by skilled operating skills and are not described in detail in the present invention.
Any range recited in the invention includes any numerical value between the endpoints and any sub-range of any numerical value between the endpoints or any numerical value between the endpoints.
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: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound E950, exemplified by g=s, comprising the steps of:
the first step: preparation of Compound Int-1
Under the protection of nitrogen, 20.0mmol of 3-cyano-2-iodobenzothiophene is dissolved in 80mL of dry THF, the temperature is reduced to minus 5 ℃, 22.0mmol of phenyl magnesium iodide THF solution is added dropwise, stirring reaction is carried out for 2 hours, 100mL of 1M dilute hydrochloric acid aqueous solution is added, extraction is carried out by ethyl acetate, organic phase is collected, drying, filtration and decompression concentration and drying are carried out on filtrate, and separation and purification are carried out by silica gel column to obtain compound Int-1, yellow solid and yield: 87%.
And a second step of: preparation of Compound Int-2
Under the protection of nitrogen, 20.0mmol of Int-1 and 22.0mmol of p-bromobenzamido propyne are mixed with 60mL of acetonitrile and 6mL of triethylamine, and 1.0mmol of cuprous iodide and 1.0mmol of PdCl are added 2 (PPh 3 ) 2 The catalyst is heated to reflux and stirred for reaction for 2 hours, cooled to room temperature, 100mL of saturated ammonium chloride aqueous solution is added, the mixture is extracted by ethyl acetate, an organic phase is collected, dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the compound Int-2 is obtained by separating and purifying by a silica gel column, yellow solid is obtained, and the yield is: 66%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, mixing 20.0mmol of Int-2 prepared in the previous step, 2.0mmol of silver trifluoroacetate, 50mL of 1, 2-dichloroethane and 20.0mmol of water, stirring at room temperature for reaction for 2 hours, adding 40.0mmol of p-toluenesulfonic acid, heating to 85 ℃ for stirring reaction for 1 hour, cooling to room temperature, adding 50mL of saturated sodium bicarbonate aqueous solution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating and drying the filtrate under reduced pressure, separating and purifying by using a silica gel column to obtain a compound Int-3, yellow solid, and obtaining the yield: 56%.
Fourth step: preparation of Compound Int-4
Under the protection of nitrogen, 20.0mmol of Int-3 prepared in the previous step, 24.0mmol of pinacol biborate, 30.0mmol of anhydrous potassium acetate, 2.0mmol of cuprous iodide and 0.2mmol of PdCl 2 (dppf), 0.4mmol XPhos and 80mL DMF were mixed, heated to 100deg.C, stirred and reacted for 15 hours, cooled to room temperature, the reaction solution was poured into 150mL saturated aqueous sodium chloride solution, filtered, the filter cake was washed with water, and the compound Int-4 was obtained as a white solid in 85% yield by separation and purification with a silica gel column.
Fifth step: preparation of Compound E950
Under the protection of nitrogen, 22.0mmol of Int-4 (reactant 1), 20.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (reactant 2), 60.0mmol of anhydrous sodium carbonate, 2.0mmol of tetrabutylammonium bromide and 0.1mmol of Pd (PPh) 3 ) 4 Mixing with 60mL of toluene solution, adding 30mL of ethanol and 30mL of water, heating to reflux, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound E950;
g=s; white solid, yield 78%, MS (TOF): m/z 609.1763[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.81～8.77(4H,m)；8.63～8.55(4H,m)；8.46～8.43(1H,m)；8.23(1H,s)；8.07～8.03(2H,m)；7.89～7.86(1H,m)；7.73～7.67(2H,m)；7.61～7.50(5H,m)；7.46～7.35(4H,m)。
G=nph; yellow solid, yield 76%, MS (TOF): m/z 668.2466[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.81～8.77(4H,m)；8.63～8.56(4H,m)；8.37～8.32(2H,m)；8.18～8.14(2H,m)；7.79～7.73(2H,m)；7.58～7.53(6H,m)；7.51～7.48(2H,m)；7.46～7.42(2H,m)；7.40～7.38(1H,m)；7.36～7.30(3H,m)；7.28～7.25(1H,m)。
Examples 2 to 39
Referring to the above-described analogous synthetic methods, the following compounds were prepared:
example 40
Preparation of compound E1000:
22.0mmol of Int-3 '(reactant 1), 20.0mmol of N- ([ 1,1' -biphenyl) under nitrogen protection]-4-yl) dibenzo [ b, d]Furan-2-amine (reactant 2), 30.0 mmol of sodium tert-butoxide and 60. 60mL of toluene were mixed and 0.2 mmol of Pd was added 2 (dba) 3 The catalyst and 0.4 mmol Xantphos are heated to 110 ℃ and stirred for reaction for 15 hours, cooled to room temperature, added with 50mL of water, extracted with ethyl acetate, collected and dried organic phase, filtered, concentrated and dried under reduced pressure, and separated and purified by a silica gel column to obtain a compound E1000;
G=s; yellow solid, yield 83%, MS (TOF): m/z 711.2072[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.45～8.43(1H,m)；8.23(1H,s)；8.07～8.02(4H,m)；7.89～7.86(1H,m)；7.75～7.67(3H,m)；7.62～7.58(3H,m)；7.55～7.45(4H,m)；7.42～7.33(6H,m)；7.25～7.20(2H,m)；7.12～7.07(2H,m)；7.02～6.97(2H,m)；6.95～6.93(1H,d)。
G=nph; yellow solid, yield 85%, MS (TOF): m/z 770.2745[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.37～8.32(2H,m)；8.18～8.14(2H,m)；8.06～8.02(2H,m)；7.79～7.72(3H,m)；7.62～7.54(5H,m)；7.52～7.45(4H,m)；7.41～7.32(9H,m)；7.30～7.27(1H,m)；7.25～7.20(2H,m)；7.12～7.07(2H,m)；7.02～6.97(2H,m)；6.95～6.93(1H,d)。
Examples 41 to 39
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
example 52
Preparation of compound E1032 comprising the steps of:
the first step: preparation of Compound Int-5
Under the protection of nitrogen, 20.0mmol of Int-3 (prepared by the synthetic method of example 1) is dissolved in 80mL of dichloromethane, the temperature is reduced to 0 ℃,22.0mmol of N-bromosuccinimide is added in batches, the temperature is raised to room temperature, stirring is carried out for 2 hours, 50mL of water is added, an organic phase is separated, the organic phase is dried and filtered, the filtrate is concentrated under reduced pressure, and the compound Int-5 is obtained after separation and purification by a silica gel column, and the yield is 85% -90%.
And a second step of: preparation of Compound E1032
Under the protection of nitrogen, 22.0mmol of Int-5 (reactant 1), 20.0mmol of biphenyl amine (reactant 2), 30.0mmol of tertiary sodium butoxide and 0.1mmol of Pd 2 (dba) 3 Mixing 0.2mmol of 10% tri-tert-butyl phosphorus toluene solution and 60mL of toluene solution, heating to 90 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with dichloromethane, drying the organic phase, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying by using a silica gel column to obtain a compound E1032;
G=s; yellow solid, yield 81%, MS (TOF): m/z 697.2321[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.28(1H,s)；8.25～8.22(2H,m)；8.07～8.03(2H,m)；7.73～7.67(4H,m)；7.62～7.55(5H,m)；7.52～7.45(4H,m)；7.42～7.35(5H,m)；7.25～7.20(4H,m)；7.02～6.97(4H,m)；6.95～6.93(1H,d)。
G=nph; yellow solid, yield 84%, MS (TOF): m/z 756.2949[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.35(1H,s)；8.25～8.22(2H,m)；8.18～8.14(2H,m)；7.79～7.74(2H,m)；7.62～7.54(7H,m)；7.52～7.45(7H,m)；7.42～7.35(5H,m)；7.33～7.27(2H,m)；7.25～7.20(4H,m)；7.12～7.07(4H,m)；6.89～6.87(1H,d)。
Examples 53 to 68
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
examples 69 to 87
Referring to the synthetic methods analogous to example 1 and example 52 above, the following compounds were prepared:
examples 88 to 103
Referring to the synthesis method similar to example 1 above, the following compounds were prepared:
preparation of practical example 1E0140 48, compound E1048 was prepared by substituting magnesium phenyl iodide THF solution with (3- (9-carbazolyl) phenyl) lithium THF solution and substituting p-bromobenzamido propyne with benzamido propyne in the first step of example 1, with reference to the synthesis method of example 1, in 45% -55% yield.
Example 105
Preparation of Compound E1051 referring to the synthetic method of example 1, the compound E1051 was prepared in 45% -55% yield by replacing the phenyl magnesium iodide THF solution of example 1 with 9-phenylcarbazole-3-lithium THF solution and replacing the p-bromobenzamido propyne of the second step with benzamido propyne.
Examples 106 to 117
Referring to the synthesis method described above in example 40, the following compounds were prepared:
example 118
Compound E1067 preparation, reference is made to the synthetic method of example 1, only the 3-cyano-2-iodobenzothiophene of the first step of example 1 is replaced by 3-iodo-2-cyanobenzothiophene or 3-iodo-2-cyanobenzofuran or 3-iodo-2-cyanobenzoindole-1-Ar 3 Compound E1067 was prepared.
Examples 119 to 185
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
example 186
Preparation of Compound E1121, reference was made to the synthetic methods of example 1 and example 105, replacing the phenyl magnesium iodide THF solution of example 1 in the first step with 9-phenylcarbazole-3-lithium THF solution, and replacing 3-cyano-2-iodobenzothiophene with 3-iodo-2-cyanobenzothiophene or 3-iodo-2-cyanobenzofuran or 3-iodo-2-cyanobenzoindole-1-Ar 3 And replacing the p-bromobenzamido propyne in the second step with benzamido propyne to prepare the compound E1121 with the yield of 45-55%.
In the above embodiments, G is selected from S or NAr 3 ；
The Ar is as follows 3 Selected from the group consisting ofGroup:
application examples 1 to 186
As shown in fig. 1, an OLED element 100 of the present embodiment is a top emission light element, and includes a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 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 manufacturing 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 HI02 as hole injection layers respectively, wherein HI02 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 a compound HT025 as an electron blocking layer on the hole transport layer to obtain an evaporating film with a thickness of
5) The compound shown in the formula (I) and RH01 in the embodiment 1 are continuously evaporated on the electron blocking layer as main materials and RD030 is used as doping materials, wherein the mass ratio of the compound shown in the formula (I) and RH01 in the embodiment is 1:1, the RD030 is 5% of the mass of the main materials, the organic light-emitting layer is used as an element, and the film thickness of the organic light-emitting layer obtained by evaporation is as follows
6) Continuously evaporating a layer of LiQ and a compound ET036 on the organic light-emitting layer as an electron transport layer of the element, wherein the compound ET036 is 40% of the mass of the LiQ, and the evaporating 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 a CPL layer with HTM as element on the transparent cathode layer to obtain an evaporated film thickness ofApplication example 1 of the OLED element provided by the invention is obtained.
The structures of the compounds used in the above application examples are as follows:
according to the same procedure as in application example 1, the compound formula of formula (I) in step 5) was replaced with the compounds shown in examples 2 to 186 to obtain application examples 2 to 186.
Application example 187
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, and the electroluminescent device 200 is manufactured by a manufacturing method similar to that of application example 1.
Comparative example 1
According to the same procedure as in application example 1, the compound formula of the present invention represented by the formula (I) in step 5) was replaced with E02 to obtain comparative element 1;
the driving voltage and current efficiency and the lifetime of the organic electroluminescent elements prepared in application examples 1 to 186, application example 187 and comparative example 1 were measured using a digital source meter and a luminance meter at the same luminance. 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; LT90% 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 900cd/m while maintaining a constant current at luminance 2 Time in hours. All results are summarized in table 1, normalized against the test data of comparative example 1 (bracketed data) for comparison.
TABLE 1 results of testing the performance of the elements
Wherein Ph is phenyl; phPh is biphenyl, nap is naphthyl.
The compound of the present invention as a material of a light-emitting layer gives an organic electroluminescent element having high efficiency and long life, a low driving voltage of the element, high current efficiency, and excellent performance in the LT90% lifetime, indicating that the compound of the present invention is an organic electroluminescent material excellent in performance.
The compound E02 of comparative example 1 is different from the compound of the present invention in that after the dibenzofuran oxazole of E02 is introduced into the triarylamine group, the electron transport ability is weaker than the hole transport ability, resulting in imbalance in transfer of excitons in the element, an increase in element driving voltage, and a decrease in efficiency. The compound of the invention improves the electron transmission capability after introducing an oxazole group into dibenzothiophene or carbazole, so that the compound has larger improvement on the exciton transmission performance when being used as a main material with n-type RH01, the exciton transmission in the element is more balanced, and the element performance is obviously improved.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. The oxazole derivative is characterized by having a structural general formula shown in a formula (I):
wherein two adjacent W represent groups represented by formula (II);
z each independently represents CR 1 Or N; and two adjacent "≡" groups are indicated for two adjacent groups W in formula (I);
g represents S, se or NAr 3 ；
R 1 Each independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Of arylsilyl groupsGroup of any adjacent two or more R 1 Optionally joined or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
Ar 1 、Ar 2 、Ar 3 each occurrence is independently selected from substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 6 ～C 50 Arylamine groups.
2. The oxazole derivative according to claim 1 wherein R is 1 Each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstitutedA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted triazinyl group, or formula (III);
Ar 1 、Ar 2 、Ar 3 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl Substituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenyl, substituted or unsubstitutedA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a formula (III);
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
Ar 4 、Ar 5 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenylA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group;
The dotted line represents the attachment site of the group.
3. The oxazole derivative according to claim 1 wherein Ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, or formula (IV);
L 2 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
het is selected from C 2 ～C 50 Heteroaryl groups;
the dotted line represents the attachment site of the group.
4. An oxazole derivative according to any of claims 1 to 3 wherein the heteroaryl group is selected from the group consisting of groups II-1 to II-13:
wherein,,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 representation O, S or NAr ’ ；
Ar ’ Selected from C 1 ～C 40 Alkyl, C of (2) 1 ～C 40 Heteroalkyl of (C) 3 ～C 40 Cycloalkyl, 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 Heteroaryl groups; preferably Ar ’ Methyl, ethyl, phenyl, biphenyl or naphthyl;
representing the attachment site of the group.
5. An oxazole derivative according to any of claims 1 to 3 wherein L is 1 、L 2 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
wherein X is selected from O, S, se, CR ' R ', siR ' R ' or NAr ';
Z 11 、Z 12 、Z 13 、Z 14 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents an integer of 1 or 2;
R ’ r' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl group, R ’ And R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R ’ R' is methyl, phenyl or fluorenyl;
Ar ’ selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, 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 group consisting of heteroaryl groups; preferably Ar ’ Methyl, ethyl, phenyl, biphenyl or naphthyl;
wherein the dotted line represents the attachment site of the group.
6. The oxazole derivative according to any of claims 1 to 5 wherein the oxazole derivative is selected from one or more of the structures E950 to E1135 shown below:
wherein G is selected from S or NAr 3 ；
The Ar is as follows 3 Selected from the group consisting of:
7. an organic electroluminescent material, characterized in that the organic electroluminescent material comprises an oxazole derivative as defined in any of claims 1 to 6.
8. An organic electroluminescent device comprising a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer or capping layer comprises an oxazole derivative as defined in any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a charge generation layer; wherein each organic layer is one, two or more layers;
Preferably, the luminescent layer, the electron transport layer, the capping layer or the charge generation layer comprises the oxazole derivative as defined in any one of claims 1 to 6.
10. A consumer product comprising the organic electroluminescent device of any one of claims 8-9.
CN202310671951.0A 2023-06-07 2023-06-07 Oxazole derivative and application thereof Pending CN116693550A (en)

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