CN116693539A - Indole derivative and application thereof - Google Patents

Indole derivative and application thereof Download PDF

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CN116693539A
CN116693539A CN202310570541.7A CN202310570541A CN116693539A CN 116693539 A CN116693539 A CN 116693539A CN 202310570541 A CN202310570541 A CN 202310570541A CN 116693539 A CN116693539 A CN 116693539A
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aryl
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曹建华
郭文龙
边坤
刘殿君
李程辉
王振宇
徐先锋
李利铮
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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 electroluminescence, in particular to an indole derivative and application thereof, wherein the structural formula of the indole derivative is shown as a formula (I):the indole derivative shown in the formula (I) provided by the invention has high triplet state energy level, carrier mobility,The organic layer is excellent in thermal stability and light-emitting characteristics and can be used for an organic electroluminescent element. In particular, when the indole 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 materials for light-emitting layers can be produced, and further, a full-color display panel having improved performance and lifetime can be produced.

Description

Indole derivative and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an indole derivative and application thereof.
Background
Organic electroluminescent elements, including fluorescent and phosphorescent types, have been widely studied for optimal element design according to respective light emission mechanisms. In a phosphor-type OLED device, it is known that a high-performance device cannot be obtained by a simple transfer of fluorescent device technology due to its light emission characteristics. The reason for this is generally considered as follows.
First, phosphorescence utilizes luminescence of triplet excitons, and thus the energy gap of a compound for a light-emitting layer must be large. The reason for this is that: the value of the energy gap (also referred to as the singlet energy level) of a certain compound is typically greater than the value of the triplet energy gap (in the present invention, the energy level difference between the lowest excited triplet state and the ground state) of the compound. Therefore, in order to effectively limit the triplet energy of the phosphorescent dopant material within the light-emitting layer, first, a host material having a triplet energy greater than that of the phosphorescent dopant material must be used in the light-emitting layer. Further, an electron transport layer and a hole transport layer are provided adjacent to the light emitting layer, and a compound having a triplet energy larger than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer.
Therefore, under the design concept based on the conventional OLED element, a compound having a larger energy gap than that of the compound used for the fluorescent OLED element is used for the phosphorescent OLED element, and thus the driving voltage of the entire OLED element is increased. Further, the hydrocarbon compound having high oxidation resistance and reduction resistance, which is useful for the fluorescent element, has a small energy gap because of its large expansion of pi electron cloud. Therefore, it is difficult to select such hydrocarbon compounds for the phosphorescent OLED element, and organic compounds containing heteroatoms such as oxygen and nitrogen are selected, and as a result, the phosphorescent OLED element has a problem of shorter lifetime than the fluorescent OLED element.
However, the exciton decay rate of triplet excitons of phosphorescent dopant materials is very slow compared to singlet excitons, which can also have a major impact on device performance. That is, the emission from singlet excitons is fast in decay rate due to the emission, and thus it is difficult to cause diffusion of excitons to the peripheral layer (for example, hole transport layer or electron transport layer) of the light emitting layer, and efficient emission can be expected. On the other hand, light emission from triplet excitons is likely to cause diffusion of excitons to the peripheral layer because of spin-forbidden and slow decay rate, and quenching of excitons is caused except for specific phosphorescent compounds. Therefore, control of the recombination region of electrons and holes is more important than that of a fluorescent OLED element.
As described above, in order to achieve higher performance of the phosphor-type OLED element, it is necessary to select a material and an element design different from those of the phosphor-type OLED element. In particular, in the case of a blue and red phosphorescent OLED element, a compound having a larger triplet energy level is more required to be used for the light-emitting layer or the peripheral layer than in the case of a green phosphorescent OLED element. Specifically, in order to obtain phosphorescence emission of blue color without loss of efficiency, it is necessary to set the triplet energy of the host material used in the light-emitting layer to approximately 3.0eV or more. In order to obtain a compound having such a high triplet energy level while satisfying other properties required as an OLED material, it is necessary to design a molecule in consideration of a new idea of pi-electron state, instead of simply combining molecules having a triplet energy level such as a heterocyclic compound. Under such circumstances, as a material of a phosphorescent OLED element emitting blue light or red light, a compound having a structure in which a plurality of heterocyclic rings are bonded has been studied.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
The invention provides an indole derivative and application thereof, which are used for solving the technical problems existing in the prior art. The indole derivative can improve triplet state energy level, thermal stability and carrier conveying capacity, and the organic electroluminescent element prepared by using the indole derivative can remarkably reduce driving voltage, improve luminous efficiency and prolong service life.
Specifically, the invention provides the following technical scheme:
the invention provides an indole derivative, which has a structural formula shown in a formula (I):
wherein two adjacent W represent a group represented by formula (II) or formula (III);
two adjacent "≡" indicate two adjacent W in formula (I);
R 1 ～R 8 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 2 NAr 4 Ar 5 A group of groups;
L 1 、L 2 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 each independently selected from the group consisting of hydrogen, nitrile, 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 8 And L is equal to 2 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.
Alkyl radicals in the sense of the present invention contain 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH 2 -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 by 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, pentyleneoxy, pentylenethio, cyclopentenyloxy, cyclopentenylmethyl, hexenylmethyl, cyclohexenyloxy, 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 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 non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Arylsilyl refers to silyl groups substituted with aryl groups having from 6 to 60 carbon atoms.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylphosphorus group, there are diphenylphosphorus group, bis (4-trimethylsilylbenzene) phosphorus group and the like. The phosphorus atom of the aryl phosphorus oxide group is the diaryl phosphorus group is oxidized to the highest valence state.
The arylboron group used in the present invention means a diarylboroyl group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylboron group, there are diphenyl boron group, bis (2, 4, 6-trimethylbenzene) boron group and the like. The alkylboryl group means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
Further, the indole derivative is selected from the group consisting of the structures shown below:
wherein R is 1 ～R 8 、L 1 、Ar 1 、Ar 2 And Ar is a group 3 The meaning of (2) is the same as defined above.
Further, m is 0, 1 or 2.
Preferably, the aryl, heteroaryl or heteroaryl group is preferably selected from phenyl, naphthyl, anthryl, benzanthraceyl, phenanthrylA radical, a pyrenyl radical,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, naphthazolyimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracnose oxazolyl, 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, fluorocyclyl, 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-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazolyl, 1,2, 4-tetrazolyl, 1,3, 4-tetrazolyl A group consisting of a 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl group, or a group derived from a combination of these systems.
Further, the heteroaryl or 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 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 ringAryl, 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.
Preferably, the R 1 ～R 8 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 、Ar 5 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, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienylPyrrolyl, 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 Ar 1 、Ar 2 、Ar 3 、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 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 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 Heteroalkyl, substituted or substitutedUnsubstituted 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' is 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' is 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 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 indole derivatives are selected from the group consisting of compounds represented by the following formulas D100-D321:
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the invention also provides an organic electroluminescent material, which comprises the indole derivatives; the organic electroluminescent material comprising the indole derivative of the present invention has a carrier transporting ability.
The invention also provides application of the indole 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 indole derivatives 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 an indole derivative according to the invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the electron blocking layer or hole transport layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner generally used according to the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method, and/or characterized in that at least one layer is applied by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or in that at least one layer is applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to indole derivatives 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 indole derivatives may preferably contain other compounds in addition to the indole derivatives. Treatment of the indole 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, an electron blocking layer, or a charge generation layer.
Further, the empty light emitting layer or the electron transporting layer comprises the indole derivative of the present invention.
Still further, the light-emitting layer comprises an indole 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 indole derivative represented by the formula (I) provided by the invention can be applied to an organic layer of an organic electroluminescent element due to high triplet energy level, carrier mobility, thermal stability and excellent luminescence characteristics. In particular, when the indole 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 materials for light-emitting layers can be produced, and further, a full-color display panel having improved performance and lifetime can be produced.
Drawings
In order to more clearly illustrate the invention or the technical solutions of the prior art, the following description will briefly explain the drawings used in the embodiments or the description of the prior art, and it is obvious that the drawings in the following description are some embodiments of the invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to a first embodiment of the present invention;
fig. 2 is a schematic structural diagram of an organic electroluminescent device according to a second embodiment of the present invention;
fig. 3 is a schematic structural diagram of an organic electroluminescent device according to a third embodiment of the present invention.
Reference numerals:
100, 200: an organic electroluminescent element; 101: a substrate; 102: an anode layer; 103: a hole injection layer; 104: a hole transport layer; 105: an electron blocking layer; 106: a light emitting layer; 1061: a first light emitting layer; 1062: a second light emitting layer; 107: a hole blocking layer; 108: an electron transport layer; 109: an electron injection layer; 110: a cathode layer; 111: a capping layer; 112: a charge generation layer.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings, and it is apparent that the described embodiments are some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within 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 D102 comprising the steps of:
the first step: preparation of intermediate Int-1
Under the protection of nitrogen, 20.0mmol of 2-cyanophenylacetylene, 22.0mmol of o-nitroiodobenzene and 2.0mmol of PdCl are introduced 2 (PPh 3 ) 2 2.0mmol of cuprous iodide, 4.0mmol of triphenylphosphine, 40mL of acetonitrile and 20mL of triethylamine are heated to reflux and stirred for reaction for 12 hours, cooled to room temperature, filtered, concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain a compound Int-1 as a yellow solid, and the yield is as follows: 76%.
And a second step of: preparation of intermediate Int-2
Introducing nitrogen protection, mixing 20.0mmol of Int-1, 40.0mmol of nitromethane, 40.0mmol of potassium hydroxide and 60mL of DMSO, heating to 110 ℃, stirring for reaction for 45 minutes, cooling to room temperature, pouring the reaction solution into 150mL of water, filtering, washing a filter cake with water, and separating and purifying by an overbased alumina column to obtain a compound Int-2 as a yellow solid, wherein the yield is as follows: 75%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, 20.0mmol of compound Int-2 is dissolved in 80mL of dry toluene, 20.0mmol of iodobenzene, 25.0mmol of tertiary sodium butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.4mmol XantPhos, raise the temperature to 90 ℃ and stir and react for 12 hours, cool to room temperature, add 50mL of water, separate the organic phase, extract the aqueous phase with ethyl acetate, dry the organic phase, concentrate dry under reduced pressure, separate and purify with silica gel column, get compound Int-3, yellow solid, yield: 81%.
Fourth step: preparation of Compound Int-4
Under nitrogen, 20.0mmol of Compound Int-3 was dissolved in 100mL of THF, and 2.0mmol of Fe (acac) was added 3 And 30.0mmol of 1, 3-tetramethyl disiloxane, heating to 60 ℃, stirring and reacting for 12 hours, cooling to room temperature, passing through an alkaline alumina short column, concentrating under reduced pressure and drying to obtain a compound Int-4, brown solid, and directly using the compound Int-4 in the next reaction without purification.
Fifth step: preparation of Compound Int-5
Under the protection of nitrogen, 20.0mmol of compound Int-4 is dissolved in 100mL of toluene, 22.0mmol of benzoic acid and 0.2mmol of p-toluenesulfonic acid are added, the mixture is heated to reflux and stirred for reaction for 12 hours, water generated by the reaction is separated out through a water separator, the mixture is cooled to room temperature, concentrated to dryness under reduced pressure, and recrystallized by ethanol to obtain compound Int-5 as a yellow solid, and the two-step yield is as follows: 62%.
Sixth step: preparation of Compound Int-6
Under the protection of nitrogen, 20.0mmol of compound Int-5 is dissolved in 50mL of anisole, 0.1mol of triethyl phosphite is added, the mixture is heated to reflux and stirred for reaction for 12 hours, the low boiling point ethanol generated by the reaction is separated out through a water separator, the mixture is cooled to room temperature, concentrated to dryness under reduced pressure, and the compound Int-6 is obtained by separating and purifying with a silica gel column, and is yellow solid with the yield: 86%.
Seventh step: preparation of Compound D102
Under the protection of nitrogen, 20.0mmol of compound Int-6 is dissolved in 60mL of DMF, 24.0mmol of 65% sodium hydride solid is added in portions, stirring is carried out for 1 hour, 24.0mmol of 2-chloro-4-biphenyl-6-phenyl-1, 3, 5-triazine is added, stirring is carried out at room temperature for 15 hours, reaction liquid is poured into 150mL of ice water, filtration is carried out, filter cake is washed by ethanol, solid is separated and purified by silica gel column, and compound D102 is obtained as yellow solid, yield: 84%, MS (MALDI-TOF): m/z=717.2704 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.56～8.50(3H,m)；8.36～8.31(3H,m)；8.28～8.23(2H,m)；7.96～7.92(2H,m)；7.75～7.68(5H,m)；7.64～7.60(2H,m)；7.56～7.42(10H,m)；7.40～7.33(4H,m)；7.18～7.14(1H,m)。
Example 2
The preparation of compound D222, comprising the steps of:
the first step: preparation of Compound Int-7
Under the protection of nitrogen, 20.0mmol of compound Int-2 and 40.0mmol of pyridine are dissolved in 80mL of dichloromethane, the temperature is reduced to 0 ℃, 24.0mmol of benzoyl chloride is added dropwise, the temperature is raised to room temperature, stirring is carried out for 15 hours, 50mL of water is added, an organic phase is separated, the water phase is extracted by dichloromethane, the organic phase is dried, the drying is carried out under reduced pressure, and the compound Int-7 is obtained after separation and purification by a silica gel column, yellow solid is obtained, and the yield is: 88%.
And a second step of: preparation of Compound Int-8
Referring to the synthesis method of the fourth step of example 1, only Int-3 of the fourth step of example 1 was replaced with Int-7 to prepare the compound Int-8, which was directly used for the next reaction without purification.
And a third step of: preparation of Compound Int-9
Under the protection of nitrogen, 20.0mmol of compound Int-8 is dissolved in 80mL of dry toluene, 20.0mmol of iodobenzene, 25.0mmol of tertiary sodium butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.4mmol XantPhos, raise the temperature to 90 ℃ and stir and react for 15 hours, cool to room temperature, add 50mL of water, separate the organic phase, the aqueous phase is extracted with ethyl acetate, the organic phase is dried, concentrate dry under reduced pressure, separate and purify with silica gel column, get compound Int-9, yellow solid, two-step yield: 53%.
Fourth step: preparation of Compound Int-10
Under the protection of nitrogen, 20.0mmol of compound Int-9 is dissolved in 100mL of toluene, 0.2mmol of p-toluenesulfonic acid is added, the temperature is raised to reflux and stirring is carried out for 12 hours, water generated by the reaction is separated out through a water separator, the temperature is reduced to room temperature, the concentration is carried out under reduced pressure, the ethanol is used for recrystallization, and the compound Int-10, yellow solid and two-step yield are obtained: 87%.
Fifth step: preparation of Compound Int-11
Referring to the synthesis of the sixth step of example 1, only the substitution of Int-5 of the sixth step of example 1 with Int-10 produced compound Int-11 as a yellow solid in 85% yield.
Sixth step: preparation of Compound D222
Under the protection of nitrogen, 20.0mmol of compound Int-11 is dissolved in 80mL of dry toluene, 24.0mmol of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine, 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 110 ℃, stirring and reacting 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, concentrating the organic phase under reduced pressure, separating and purifying the organic phase by a silica gel column to obtain a compound D222, yellow solid and yield: 83%, MS (MALDI-TOF): m/z=717.2702 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53～8.48(3H,m)；8.36～8.32(4H,m)；8.26～8.22(3H,m)；8.20(1H,s)；7.95～7.92(1H,m)；7.74～7.68(3H,m)；7.62～7.58(2H,m)；7.55～7.42(11H,m)；7.38～7.32(3H,m)；7.18～7.15(1H,m)。
Examples 3 to 156
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 157
Preparation of compound D259, comprising the steps of:
the first step: preparation of Compound Int-12
Under nitrogen, 20.0mmol of Compound Int-2 was dissolved in 100mL of THF, and 2.0mmol of Fe (acac) was added 3 And 30.0mmol of 1, 3-tetramethyl disiloxane, heating to 60 ℃, stirring and reacting for 12 hours, cooling to room temperature, adding 50mL of 2M diluted hydrochloric acid, cooling to 0 ℃, filtering, and washing a filter cake with water to obtain a compound Int-12, yellow solid, wherein the yield is 82%.
And a second step of: preparation of Compound Int-13
Under the protection of nitrogen, 20.0mmol of compound Int-12 is dissolved in 60mL of glacial acetic acid, 22.0mmol of diphenyldione is added, the temperature is raised to reflux, stirring is carried out for 10 hours, the temperature is reduced to room temperature, filtration is carried out, a filter cake is washed with water and ethanol, and compound Int-13 is obtained as a yellow solid, and the yield is 85%.
And a third step of: preparation of Compound Int-14
Referring to the synthesis of the sixth step of example 1, only the substitution of Int-5 of the sixth step of example 1 with Int-13 produced compound Int-14 as a yellow solid in 83% yield.
Fourth step: preparation of Compound D259
Referring to the synthetic method of the seventh step of example 1, substituting Int-6 of the seventh step of example 1 with Int-14 (reactant 1) and substituting 2-chloro-4-biphenyl-6-phenyl-1, 3, 5-triazine with 2-chloro-4, 6-bis (m-biphenyl) -1,3, 5-triazine (reactant 2), compound D259 was prepared as a yellow solid, yield: 85%, MS (MALDI-TOF): m/z=805.3087 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53～8.48(3H,m)；8.36～8.33(2H,m)；8.03～7.99(4H,m)；7.96～7.92(3H,m)；7.76～7.65(8H,m)；7.62～7.57(4H,m)；7.55～7.48(4H,m)；7.43～7.39(2H,m)；7.36～7.30(5H,m)；7.16～7.12(1H,m)。
Example 158
Preparation of compound D293:
under the protection of nitrogen, 20.0mmol of compound Int-14 is dissolved in 80mL of dry toluene, 24.0mmol of 2- (2-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine, 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.5mmol of 10% tri-tert-butyl phosphorus toluene solution, heating to 110 ℃, stirring and reacting 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, concentrating the organic phase under reduced pressure, separating and purifying the organic phase by a silica gel column to obtain a compound D293, yellow solid and yield: 82%, MS (MALDI-TOF): m/z=729.2704 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53～8.48(3H,m)；8.36～8.32(4H,m)；8.03～7.99(4H,m)；7.93～7.88(3H,m)；7.82～7.78(1H,m)；7.74～7.70(2H,m)；7.62～7.58(2H,m)；7.55～7.46(7H,m)；7.34～7.27(5H,m)；7.18～7.15(1H,m)。
Examples 159 to 224
Referring to the synthesis method similar to the above examples, the following compounds shown in table 2 were prepared:
TABLE 2
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Application example 1
An organic electroluminescent device 100, specifically an OLED device, as shown in fig. 1, the OLED device of the present embodiment is a top-emission light device, 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, an electron transport layer 108 disposed on the organic light emitting layer 106, an electron injection layer 109 disposed on the electron transport layer 108, and a capping layer 111 disposed on a cathode layer 110 and a cathode layer 110 on the electron injection layer 109, and the method for preparing the OLED device 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, a metallic silver is deposited as an anode layer 102 on the ITO glass substrate (substrate 101), and the thickness of the deposited film isContinuing to vapor deposit the compounds HI01 and HI02 as the hole injection layer 103, respectively, wherein HI02 is 3% by mass of HI01, and the vapor deposition film thickness is +.>
3) Continuously evaporating a compound HTM as a hole transport layer 104 on the hole injection layer 103 to obtain an evaporated film thickness of
4) Continuing to vapor deposit a compound HT022 as an electron blocking layer 105 on the hole transport layer 104, wherein the vapor deposition film thickness is equal to
5) The compound of formula (I) of the present invention is continuously deposited on the electron blocking layer 105 as a host material and RD029 as a dopant material, RD029 is 5% by mass of the compound of formula (I) as an organic light emitting layer 106 of the device, and the film thickness of the deposited organic light emitting layer 106 is
6) An electron transport layer 108 of LiQ and a compound ET030 as elements is continuously deposited on the organic light-emitting layer 106, wherein the compound ET030 is 50% of the mass of LiQ, and the deposition film thickness is
7) Continuously evaporating LiF on the electron transport layer 108 to obtain an electron injection layer 109 with a thickness of
8) A transparent cathode layer 110 of which the element is a metal magnesium and silver deposited on the electron injection layer 109, wherein the mass ratio of magnesium to silver is 1:10, and the thickness of the deposited film is/>
9) A CPL layer (capping layer 111) is deposited on the transparent cathode layer 110 to form a CPD device with a thickness ofThe OLED element provided by the invention is obtained.
The structure of the compound used in application example 1 is as follows:
further, a hole blocking layer 107 may be further disposed between the organic light emitting layer 106 and the electron transport layer 108 of the OLED element, and the specific structure is shown in fig. 2.
Application example 2
An organic electroluminescent element 200 having a structure as shown in fig. 3 and comprising a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, a first light emitting layer 1061, an electron transport layer 108, a charge generation layer 112, a hole injection layer 103, a hole transport layer 104, a second light emitting layer 1062, an electron transport layer 108, an electron injection layer 109, a cathode layer 110 and a capping layer 111 was prepared by a similar preparation method as that of application example 1. The organic electroluminescent element 200 has a first light emitting layer 1061 and a second light emitting layer 1062, and the light emitting peak shapes of the first light emitting layer 1061 and the second light emitting layer 1062 may be overlapped or cross-overlapped or non-overlapped.
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 example 3 to application example 224
The difference is that the compound represented by the formula (I) in step 5) is different from the application example in which the hole blocking layer 107 is not provided in application example 1, specifically as shown in table 3 below. The indole derivatives of the present invention prepared in the above examples were vacuum sublimated to 99.90% or more, organic electroluminescent elements were prepared by referring to the methods similar to application examples 1 and 2, and the organic electroluminescent elements prepared in the above processes were subjected to the following performance tests:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent elements prepared in the above application examples 3 to 224 and comparative example 1 were measured using a digital source meter and a luminance meter. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; LT95% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 950cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 3 are relative data compared to comparative element 1 (test data in brackets).
TABLE 3 Table 3
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As is clear from Table 3, the indole derivatives of the present invention have lower driving voltage than H01, significantly improved current efficiency up to as much as 1.3 times that of the comparative element, and significantly improved LT95% lifetime of the element, at the same luminance, indicating that the indole derivatives of the present invention are excellent light-emitting layer materials.
The compound H01 of comparative example 1 is different from the compound of the present invention in that the phenanthroindole has a weak planar conjugation ability and a reduced charge transport property, resulting in a high driving voltage and low efficiency, whereas the indole derivative of the present invention has an enhanced planar conjugation ability after imidazole and quinoxaline are introduced into the naphthalene ring of the naphtoindole, and thus has an enhanced charge transport property, and thus is more excellent in molecular film formation and carrier transport properties, and the transfer of excitons within the element is more balanced, and thus the element performance is significantly improved.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims (10)

1. An indole derivative is characterized in that the structural formula of the indole derivative is shown as a formula (I):
wherein two adjacent W represent a group represented by formula (II) or formula (III);
two adjacent "≡" indicate two adjacent W in formula (I);
R 1 ～R 8 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 2 NAr 4 Ar 5 A group of groups;
L 1 、L 2 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 each independently selected from the group consisting of hydrogen, nitrile, 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 8 And L is equal to 2 The bonding locations.
2. The indole derivative according to claim 1, wherein the indole derivative is selected from the group consisting of the following structures:
wherein R is 1 ～R 8 、L 1 、Ar 1 、Ar 2 And Ar is a group 3 The meaning of (a) is as defined for formula (I);
m is 0, 1 or 2.
3. Indole derivative according to claim 1 or 2, characterized in that R is 1 ～R 8 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, andsubstituted 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 、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 pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, 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, or a substituted or unsubstituted triazinyl group.
4. Indole derivative according to claim 1, characterized in that 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 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, 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 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 Heterocyclic aryl group compositionIs a group of (3); preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
wherein the dotted line represents the attachment site of the group.
5. The indole 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 indicated 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, 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 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. Indole derivative according to any one of claims 1 to 5, characterized in that it is chosen from the compounds represented by the following formulae D100 to D321:
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7. Use of an indole derivative according to any one of claims 1 to 6 for the preparation of an organic electroluminescent element.
8. An organic electroluminescent element, characterized in that it comprises: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer comprises an indole 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, an electron blocking layer, or a charge generation layer;
the light-emitting layer or electron-transporting layer comprising the indole 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.
CN202310570541.7A 2023-05-19 2023-05-19 Indole derivative and application thereof Pending CN116693539A (en)

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