CN117069730A - Carbazole derivative, organic electroluminescent material and organic electroluminescent element - Google Patents

Carbazole derivative, organic electroluminescent material and organic electroluminescent element Download PDF

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CN117069730A
CN117069730A CN202310539269.6A CN202310539269A CN117069730A CN 117069730 A CN117069730 A CN 117069730A CN 202310539269 A CN202310539269 A CN 202310539269A CN 117069730 A CN117069730 A CN 117069730A
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aryl
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曹建华
唐伟
宗冠华
唐怡杰
邸庆童
张昊
边坤
刘殿君
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative and application thereof in electronic elements and electronic devices. The carbazole derivative is applied to organic electroluminescent materials and organic electroluminescent elements, and can remarkably reduce driving voltage, improve luminous efficiency and prolong service life.

Description

Carbazole derivative, organic electroluminescent material and organic electroluminescent element
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative, an organic electroluminescent material and application thereof in organic light-emitting elements and electronic devices.
Background
In recent years, organic electroluminescent display technology has tended to mature, some products have been brought into the market, but in the industrialized time, there are still many problems to be solved, especially, various organic materials for manufacturing elements, such as carrier injection and transmission performance, electroluminescent performance, service life, color purity, matching between various materials and various electrodes, and the like, have not been solved. Especially, the light emitting element has not reached practical requirements in light emitting efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is largely classified into fluorescence and phosphorescence, but according to spin quantum statistics theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from singlet exciton radiative transitions is 25% and the theoretical limit of fluorescence from triplet exciton radiative transitions is 75%. How to use the energy of 75% of triplet excitons becomes urgent. The fact that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material in 1997 is found by Forrest and the like, and the wide attention of people on the metal complex phosphorescence material is brought. Since then, a great deal of research has been conducted on phosphorescent materials.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
The invention aims to provide a carbazole derivative which can improve the thermal stability of materials and the capability of transporting carriers, and an organic electroluminescent element prepared by the carbazole derivative 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 carbazole derivative, which has a structural formula shown in a formula (I):
Wherein two adjacent W represent groups of formula (II);
z each independently represents CR 7 Or N; g is selected from O, S, CR 8 R 9 Or NL 2 Ar 2 The method comprises the steps of carrying out a first treatment on the surface of the And two adjacent "≡" indicate two adjacent W in formula (I);
R 1 ～R 9 each independently selected from the group consisting of hydrogen, deuterium, fluorine, hydroxyl, 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 Heteroalkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted 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 Arylthio, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted C 2 -C 60 Heteroaryl, or-L 3 NAr 3 Ar 4 A group of groups;
L 1 、L 2 、L 3 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;
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 group consisting of heteroaryl groups; m is an integer of 0 to 5;
* -represents R 1 ～R 9 And L is equal to 3 The bonding locations.
In the substituted or unsubstituted ring formed by joining or ring closure as described in the present invention, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring. 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.
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.
For the book Alkyl radicals in the sense of the invention contain 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH 2 -linear alkyl groups or alkyl groups with branches, the groups of which may also be substituted; 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 oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxyPropynylthio, 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 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.
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 such aryloxy groupNon-limiting examples of (a) include phenoxy, naphthoxy, diphenoxy, 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.
Further, the carbazole derivative is selected from the group consisting of the structures shown below:
wherein R is 1 ～R 9 、L 1 、L 2 、Ar 1 And Ar is a group 2 The meaning of (C) is as defined for formula (I).
Further, m is 0, 1 or 2.
Preferably, the aryl, heteroaryl or heteroaryl group is preferably selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, pyrenyl,radicals, perylene radicals, fluoranthryl radicals, naphthacene radicals, pentacene radicals, benzopyrene radicals, biphenylene radicals, couplesPhenyl, terphenyl, trimeric phenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, triphenylenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-indenocarbazolyl, indolocarbazolyl, benzofurancarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, 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, 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.
Further, the heteroaryl or heteroaryl group is selected from the group consisting of groups II-1 to II-13:
wherein Z is 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 2 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.
Preferably, the R 1 ～R 9 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.
Preferably, the Ar 1 、Ar 2 、Ar 3 、Ar 4 Each independently 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, 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, naphthamidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracenoxazolyl, phenanthroimidazoleOxazolyl, 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, fluoroyl, 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-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, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.
Further, the Ar 1 、Ar 2 、Ar 3 、Ar 4 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 pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, 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 substituted or unsubstituted triazinyl group.
Further, the L 1 、L 2 、L 3 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
wherein T is 1 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 linking site of the group, and the binding site of the groups represented by the above formulas III-1 to III-25 is not limited, and may be any of ortho-, meta-, and para-ones. L as described above 1 、L 2 、L 3 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.
Preferably, the carbazole derivative is selected from compounds represented by the following formulas D100-D297:
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Wherein-g— is selected from-O-, S-, or one of the following structures:
* -and- (x) represents a bond.
The invention also provides an organic electroluminescent material, which comprises the carbazole derivative; the organic electroluminescent material comprising the carbazole derivative of the present invention has a carrier transporting ability.
The invention also provides application of the carbazole derivative 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 carbazole derivative 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 a carbazole derivative 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. 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, 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 a carbazole derivative 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, the carbazole derivative may preferably contain other compounds in addition to the carbazole derivative. Treatment of the carbazole derivatives 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.
Further, the empty light emitting layer or the electron transporting layer contains the carbazole derivative of the present invention.
Still further, the light-emitting layer contains the carbazole derivative of the present invention.
The invention also provides a consumer electronic device 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 carbazole derivative represented by formula (I) provided by the present invention is excellent in carrier mobility, thermal stability, and light-emitting characteristics, and can be used in an organic layer of an organic electroluminescent element. In particular, when the carbazole derivative represented by the formula (I) of the present invention is used for a light-emitting layer, an organic electroluminescent element having a lower driving voltage, higher efficiency, and longer lifetime than conventional light-emitting layer 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 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 the device 200, materials similar to those described with respect to the device 1 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 the preparation of compound D101, exemplified by g=o, comprising the steps of:
the first step: preparation of intermediate Int-1
Under the protection of nitrogen, 20.0mmol of 4-bromo-carbazole-9-carboxylic acid tert-butyl ester is dissolved in 30mL of THF and 30mL of triethylamine, 22.0mmol of o-methoxyphenylacetylene, 2.0mmol of cuprous iodide and 2.0mmol of PdCl are added 2 (PPh 3 ) 2 And 2.0mmol of DMAP, heating, refluxing, stirring, reacting for 15 hours, concentrating and drying under reduced pressure, and separating and purifying by a silica gel column to obtain a compound Int-1 as a yellow solid, wherein the yield is as follows: 84%.
And a second step of: preparation of intermediate Int-2
Under the protection of nitrogen, 20.0mmol of Int-1 prepared in the previous step, 60.0mmol of copper bromide, 10.0mmol of anhydrous potassium phosphate and 60mL of nitromethane are mixed, the mixture is heated to reflux and stirred for reaction for 10 hours, cooled to room temperature, filtered, concentrated and dried under reduced pressure, and the compound Int-2 is obtained by separating and purifying with a silica gel column, and is yellow solid with the yield of 92%.
And a third step of: preparation of intermediate Int-3
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 80mL of dry dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron tribromide is added dropwise, stirring reaction is carried out for 2 hours, 50mL of 1N diluted hydrochloric acid aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phases are combined and dried, filtration and filtrate decompression concentration and drying are carried out, and silica gel column separation and purification are carried out, thus obtaining intermediate Int-3, yellow solid with the yield of 95%.
Fourth step: preparation of intermediate Int-4
Under the protection of nitrogen, 20.0mmol of Int-3 is dissolved in 60mL of DMF, 50.0mmol of anhydrous potassium carbonate is added, the temperature is raised to 120 ℃ and the mixture is stirred for reaction for 15 hours, the temperature is reduced to room temperature, the reaction solution is poured into 150mL of water and filtered, filter cakes are washed with water and ethanol, and the intermediate Int-4 is obtained after separation and purification by a silica gel column, and the yield is 85%.
Fifth step: preparation of Compound D101
Under the protection of nitrogen, 10.0mmol of intermediate Int-4 (reactant 1) is dissolved in 50mL of DMF, the temperature is reduced to 0 ℃, 12.0mmol of 65% sodium hydride solid is added in portions, stirring reaction is carried out for 1 hour, 12.0mmol of 2-chloro-4-naphthyl-6-phenyl-1, 3, 5-triazine (reactant 2) is added, the temperature is raised to room temperature, stirring reaction is carried out for 12 hours, the reaction solution is added into 150mL of ice water, filtering is carried out, the filter cake is washed with water and ethanol, and silica gel column separation and purification are carried out to obtain a compound D101;
g=o, yellow solid, yield: 86%, MS (MALDI-TOF): m/z=563.1808 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：9.06(1H,s)；8.48～8.47(1H,d)；8.34～8.32(2H,m)；8.18～8.13(2H,m)；8.10～8.06(2H,m)；8.01～7.96(2H,m)；7.87～7.84(2H,m)；7.64～7.57(4H,m)；7.55～7.48(4H,m)；7.37～7.34(1H,m)；7.32～7.28(1H,m)。
G=s (only o-methoxyphenylacetylene of the first step was replaced with o-ethynylphenyl sulfide), yellow solid, yield: 85%, MS (MALDI-TOF):
m/z＝579.1583[M+H] + ； 1 HNMR(δ、CDCl 3 )：9.08(1H,s)；8.48～8.43(2H,m)；8.35～8.32(2H,m)；8.16～8.10(3H,
m)；8.06～8.04(1H,d)；7.98～7.93(2H,m)；7.87～7.84(2H,m)；7.64～7.57(4H,m)；7.55～7.49(4H,m)；7.47～7.44(1H,m)。
example 2
Preparation of compound D100, g=cph 2 (Ph is phenyl) for example, comprising the steps of:
The first step: preparation of Compound Int-6
Under the protection of nitrogen, 20.0mmol of Int-5 (prepared by the synthesis method of example 1, only o-methoxyphenylacetylene in the first step of example 1 is replaced by phenylacetylene) is dissolved in 60mL of dry THF, cooled to-78 ℃, 22.0mmol of 2.5M n-butyllithium n-hexane solution is dropwise added for stirring reaction for 10 minutes, 24.0mmol of benzophenone solution dissolved in THF is dropwise added for stirring reaction for 30 minutes, the temperature is raised to room temperature, 50mL of saturated ammonium chloride aqueous solution is dropwise added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtered, the filtrate is concentrated under reduced pressure and dried, and the compound Int-6 is obtained by separating and purifying a silica gel column, and the yield is 87%.
And a second step of: preparation of Compound Int-7
Under the protection of nitrogen, 20.0mmol of Int-6 is dissolved in 80mL of dry dichloromethane, 30.0mmol of boron trifluoride diethyl etherate solution is added dropwise at room temperature for reaction for 2 hours under stirring, 50mL of 5% sodium hydroxide aqueous solution is added dropwise, an organic phase is separated, an aqueous phase is extracted by dichloromethane, the organic phases are combined and dried, filtration and reduced pressure concentration and drying of filtrate are carried out, and compound Int-7 is obtained by separation and purification by a silica gel column, and a white solid is obtained with the yield of 91%.
And a third step of: preparation of Compound D100
Referring to the synthesis of the fifth step of example 1, compound D100 was prepared by substituting Int-4 of the fifth step of example 1 with Int-7 (reactant 1) and substituting 2-chloro-4-naphthyl-6-phenyl-1, 3, 5-triazine with 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (reactant 2); yellow solid, yield: 83%, MS (MALDI-TOF): m/z=663.2484 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.35～8.31(4H,m)；8.22(1H,s)；8.15～8.12(1H,m)；8.10～8.08(1H,m)；7.87～7.83(2H,m)；7.75～7.71(1H,m)；7.62～7.56(3H,m)；7.54～7.46(6H,m)；7.38～7.35(1H,m)；7.26～7.20(4H,m)；7.18～7.13(2H,m)；7.11～7.06(4H,m)。
Example 3
The preparation of compound D145, exemplified by g=nph (Ph is phenyl), comprises the steps of:
the first step: preparation of Compound Int-8
Under the protection of nitrogen, 20.0mmol of Int-5' (prepared by the synthetic method of example 1, wherein only the o-methoxyphenylacetylene of the first step of example 1 is replaced by o-chlorophenylacetylene) is dissolved in 80mL of dry toluene, 22.0mmol of aniline, 60.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.6mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 100 ℃ and stirring for reaction for 15 hours, cooling to room temperature, adding 100mL of 3N diluted hydrochloric acid aqueous solution, separating out an organic phase, extracting an aqueous phase by ethyl acetate, merging and drying the organic phases, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying by using a silica gel column to obtain a compound Int-8 as a yellow solid with the yield of 86%.
And a second step of: preparation of Compound D145
Referring to the synthetic procedure of the fifth step of example 1, substituting Int-4 of the fifth step of example 1 with Int-8 (reactant 1) and substituting 2-chloro-4-naphthyl-6-phenyl-1, 3, 5-triazine with 2-chloro-4-phenylquinazoline (reactant 2), compound D145 was prepared as a yellow solid in yield: 87%, MS (MALDI-TOF): m/z=561.2093 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53(1H,s)；8.15～8.10(3H,m)；7.95～7.92(1H,m)；7.90～7.86(2H,m)；7.84～7.78(4H,m)；7.65～7.57(6H,m)；7.55～7.48(5H,m)；7.33～7.29(1H,m)；7.16～7.12(1H,m)。
Examples 4 to 71
Referring to the synthesis method similar to the above examples, the following compounds shown in table 1 were prepared:
TABLE 1
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Example 72
A process for the preparation of compound D175 comprising the steps of:
the first step: preparation of intermediate Int-9
Referring to the synthesis of the first step of example 1, substituting tert-butyl 4-bromo-carbazole-9-carboxylate of the first step of example 1 with 4-bromo-9-phenylcarbazole and substituting o-methoxyphenylacetylene with o-chlorophenylacetylene produced compound Int-9 as a yellow solid in 83% yield.
And a second step of: preparation of intermediate Int-10
Referring to the synthesis of the second step of example 1, only the substitution of Int-1 of the second step of example 1 with Int-9 produced compound Int-10 as a yellow solid in 92% yield.
And a third step of: preparation of intermediate Int-11
Under the protection of nitrogen, 20.0mmol of Int-10 is dissolved in 80mL of dried xylene, 24.0mmol of tert-butyl carbamate, 60.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.6mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 110 ℃ and stirring for reaction for 15 hours, cooling to room temperature, adding 100mL of 3N diluted hydrochloric acid aqueous solution, separating out an organic phase, extracting an aqueous phase by ethyl acetate, merging and drying the organic phases, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying by using a silica gel column to obtain a compound Int-11 as a yellow solid with the yield of 82%.
Fourth step: preparation of Compound D175
Referring to the synthetic method of the fifth step of example 1, substituting Int-4 of the fifth step of example 1 with Int-11 (reactant 1) and substituting 2-chloro-4-naphthyl-6-phenyl-1, 3, 5-triazine with 2-biphenyl-4-chloro-6-phenyl-1, 3, 5-triazine (reactant 2), compound D175 was prepared as a yellow solid in yield: 85%, MS (MALDI-TOF): m/z=664.2435 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53(1H,s)；8.36～8.31(3H,m)；8.15～8.12(1H,m)；8.10～8.07(1H,m)；7.95～7.89(2H,m)；7.87～7.83(2H,m)；7.76～7.71(3H,m)；7.65～7.58(5H,m)；7.56～7.46(8H,m)；7.43～7.39(1H,m)；7.36～7.31(1H,m)；7.16～7.12(1H,m)。
Examples 73 to 106
Referring to the above-described similar synthetic method, the following compounds shown in table 2 were prepared:
TABLE 2
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Example 107
Preparation of compound D207:
20.0mmol of Int-12 (prepared by the synthesis method of example 1 to example 3, reactant 1) are dissolved in 60mL of dry toluene under nitrogen protection, 24.0mmol of 2- (2-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (reactant 2), 30.0mmol of sodium tert-butoxide, 0.1mmol of Pd are added 2 (dba) 3 And 0.2mmol Xantphos, heating to 100deg.C, stirring for reaction for 15 hr, cooling to room temperature, adding 50mL saturated ammonium chloride aqueous solution, separating out organic phase, extracting aqueous phase with toluene, mixing and drying the organic phase, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying with silica gel column to obtain compound D207;
g=o, yellow solid, yield 84%, MS (MALDI-TOF): m/z=589.1966 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.36～8.32(4H,m)；8.16～8.11(2H,m)；7.96～7.90(3H,m)；7.88～7.84(2H,m)；7.81～7.78(1H,m)；7.65～7.60(2H,m)；7.55～7.46(7H,m)；7.44～7.38(2H,m)；7.35～7.31(1H,m)。
G=s, yellow solid, yield 80%, MS (MALDI-TOF): m/z=605.1736 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.43(1H,s)；8.34～8.30(4H,m)；8.16～8.12(1H,m)；8.10～8.07(1H,m)；7.92～7.89(3H,m)；7.87～7.82(2H,m)；7.80～7.76(1H,m)；7.64～7.60(2H,m)；7.58～7.46(8H,m)；7.44～7.41(1H,m)。
G＝CPh 2 Yellow solid, 86% yield, MS (MALDI-TOF): m/z=739.2869 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.35～8.31(4H,m)；8.23(1H,s)；8.16～8.12(1H,m)；8.10～8.07(1H,m)；7.91～7.84(4H,m)；7.80～7.74(2H,m)；7.62～7.58(2H,m)；7.55～7.46(7H,m)；7.44～7.41(1H,m)；7.37～7.33(1H,m)；7.25～7.20(4H,m)；7.18～7.13(2H,m)；7.11～7.05(4H,m)。
G=nph, yellow solid, yield 83%, MS (MALDI-TOF): m/z=664.2437 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53(1H,s)；8.35～8.31(4H,m)；8.15～8.11(2H,m)；7.92～7.88(3H,m)；7.86～7.82(2H,m)；7.79～7.76(1H,m)；7.65～7.58(4H,m)；7.56～7.46(9H,m)；7.44～7.41(1H,m)；7.34～7.31(1H,m)；7.14～7.11(1H,m)。
Examples 108 to 198
Referring to the above-described similar synthetic method, the following compounds shown in table 3 were prepared:
TABLE 3 Table 3
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In the above embodiments, g— is selected from one of the following structures:
* -and- (x) represents a bond.
Application example 1
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 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 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 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 a compound HT022 as an electron blocking layer on the hole transport layer, wherein the evaporating film thickness is as follows
5) The compound shown in the formula (I) is used as a main material and RD025 is used as a doping material, RD025 is 5 percent of the mass of the compound shown in the formula (I) and is used as an organic light-emitting layer of the element, and the film thickness of the organic light-emitting layer obtained by evaporation plating is
6) Continuously evaporating a layer of LiQ and a compound ET030 as electron transport layers of the element on the organic light-emitting layer, wherein the compound ET030 is 50% 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 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 application example 1 is as follows:
application example 2
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 of the present invention of formula (I) in step 5) was replaced with H01 to obtain comparative element 1;
application examples 3 to 200
The carbazole derivative of the present invention prepared in the above examples was subjected to vacuum sublimation purification to 99.95% or more, organic electroluminescent elements were prepared with reference to application examples 1 and 2, and the organic electroluminescent elements prepared in the above-described process were subjected to the following performance tests:
The driving voltage and current efficiency of the organic electroluminescent elements prepared in the above application examples and comparative example 1 and the lifetime of the elements 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 (test data in brackets).
TABLE 4 Table 4
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In the above table, ph is phenyl, phPh is biphenyl, nap is naphthyl.
As is clear from Table 4, the carbazole derivative of the present invention produced devices having a lower driving voltage than H01, a significantly improved current efficiency up to as much as 1.2 times that of the comparative devices, and a significantly improved LT95% lifetime of the devices, at the same luminance, showed that the carbazole derivative of the present invention was a luminescent layer material excellent in performance.
The compound H01 of comparative example 1 is different from the compound of the present invention in that carbazole plane conjugation ability as a donor group is weak, charge transport property is lowered, resulting in high voltage and reduced efficiency, whereas carbazole derivative of the present invention has enhanced plane conjugation ability of a donor unit after benzofuran, benzothiophene or indole is introduced into a donor group, and thus, it is more excellent in molecular film formation and exciton transport properties, and transfer of excitons in an element is more balanced, and thus element performance is significantly improved.
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. The carbazole derivative is characterized by having a structural formula shown in a formula (I):
wherein two adjacent W represent groups of formula (II);
z each independently represents CR 7 Or N; g is selected from O, S, CR 8 R 9 Or NL 2 Ar 2 The method comprises the steps of carrying out a first treatment on the surface of the And two adjacent "≡" indicate two adjacent W in formula (I);
R 1 ～R 9 each independently selected from the group consisting of hydrogen, deuterium, fluorine, hydroxyl, 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 Heteroalkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted 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 Arylthio, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted C 2 -C 60 Heteroaryl, or-L 3 NAr 3 Ar 4 A group of groups;
L 1 、L 2 、L 3 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;
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 group consisting of heteroaryl groups;
m is an integer of 0 to 5;
* -represents R 1 ～R 9 And L is equal to 3 The bonding locations.
2. The carbazole derivative according to claim 1, wherein the carbazole derivative is selected from the group consisting of the following structures:
wherein R is 1 ～R 9 、L 1 、L 2 、Ar 1 And Ar is a group 2 The meaning of (a) is as defined for formula (I);
m is 0, 1 or 2.
3. Carbazole derivative according to claim 1 or 2, characterized in that R 1 ～R 9 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene;
Ar 1 、Ar 2 、Ar 3 、Ar 4 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 pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, 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 substituted or unsubstituted triazinyl group.
4. Carbazole derivative according to claim 1, characterized in that the L 1 、L 2 、L 3 Each independently selected from a single bond or from the group consisting of groups III-1 to III-25:
wherein T is 1 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 groups, or substituted or unsubstitutedSubstituted 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, 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.
5. The carbazole derivative according to any one of claims 1 to 4, characterized in that the heteroaryl or heteroaryl group is selected from the group consisting of the groups represented by the following II-1 to II-13:
wherein,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, and ammoniaA group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group 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 2 Represent O, S or NAr';
ar' is 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' is methyl, ethyl, phenyl, biphenyl or naphthyl;
representing the attachment site of the group.
6. Carbazole derivative according to any one of claims 1 to 5, characterized in that it is selected from compounds represented by the following formulae D100 to D297:
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wherein-g— is selected from-O-, S-, or one of the following structures:
* -and- (x) represents a bond.
7. Use of the carbazole derivative according to any one of claims 1 to 6 for the preparation of organic electroluminescent elements.
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 carbazole derivative 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 or the electron-transporting layer includes the carbazole derivative according to any one of claims 1 to 6.
10. A consumer electronic device characterized in that it comprises the organic electroluminescent element of claim 8.
CN202310539269.6A 2023-05-12 2023-05-12 Carbazole derivative, organic electroluminescent material and organic electroluminescent element Pending CN117069730A (en)

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