CN117069596A - Amine compound, organic electroluminescent element and consumer electronic device - Google Patents

Amine compound, organic electroluminescent element and consumer electronic device Download PDF

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CN117069596A
CN117069596A CN202310933472.1A CN202310933472A CN117069596A CN 117069596 A CN117069596 A CN 117069596A CN 202310933472 A CN202310933472 A CN 202310933472A CN 117069596 A CN117069596 A CN 117069596A
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substituted
unsubstituted
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layer
amine
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曹建华
赵利杰
张九敏
董梁
申旭
梁红红
聂文凤
李建国
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Beijing Bayi Space LCD Technology Co Ltd
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Beijing Bayi Space LCD Technology Co Ltd
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    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C07C2601/00—Systems containing only non-condensed rings
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  • Electroluminescent Light Sources (AREA)

Abstract

The invention is thatRelates to the technical field of organic electroluminescent materials, in particular to an amino compound, an organic electroluminescent element and a consumer electronic device. The structural formula of the amine compound containing the adamantyl is shown as the formula (I); the compound is applied to an organic electroluminescent element, so that the driving voltage can be obviously reduced, the luminous efficiency can be improved, and the service life can be prolonged;

Description

Amine compound, organic electroluminescent element and consumer electronic device
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an amino compound, an organic electroluminescent element and a consumer electronic device.
Background
Most of the materials used in the organic electroluminescent element are pure organic materials or organometallic complexes of organic materials and metals, and they are classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, depending on the application. Here, an organic substance having a relatively small ionization energy is mainly used as the hole injection substance or the hole transport substance, and an organic substance having a relatively large electronegativity is mainly used as the electron injection substance or the electron transport substance. Further, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics.
First, the materials used in the organic electroluminescent element need to have good thermal stability because joule heat is generated by charge transfer inside the organic electroluminescent element, and conventionally, the glass transition temperature of the materials generally used as hole transport layers is low, and thus, a phenomenon occurs in which light emission efficiency is lowered due to crystallization occurring at the time of driving at low temperature. Second, in order to reduce the driving voltage, it is necessary that the organic material adjacent to the cathode and anode is designed to have a small charge injection barrier and a high charge mobility. Third, there is always an energy barrier at the interface of the electrode and the organic layer, and at the interface of the organic layer and the organic layer, and some charges are inevitably accumulated, so that it is necessary to use a substance excellent in electrochemical stability.
The organic electroluminescent device generally includes an anode, a hole injection layer, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light, and therefore, the luminous efficiency of the luminous device depends on the utilization rate and the light extraction efficiency of the excitons. The low light extraction efficiency is one of the common problems of the organic light emitting device, and particularly, attenuation due to reflection caused by the difference in refractive index of the organic material between layers becomes a main cause of the reduction in device efficiency. In order to reduce this influence, it is necessary to form an organic layer formed of a material having a low refractive index on the light-emitting side. However, the organic material has a higher refractive index from the compound of unsaturated bond with high carrier transport property and thermal stability.
For the above reasons, the present invention has been made.
Disclosure of Invention
In order to solve the problems, the invention provides an amino compound, an organic electroluminescent element and a consumer electronic device, wherein the amino compound can reduce refractive index, improve thermal stability of materials and capability of transporting carriers, and the organic electroluminescent element prepared by using the amino compound can remarkably reduce driving voltage, improve luminous efficiency and prolong service life.
Specifically, the invention provides the following technical scheme:
the invention firstly provides an amino compound, the structure of which is shown as a formula (I):
wherein,
L 1 、L 2 、L 3 each independently selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heteroarylene, or a group consisting of the foregoing;
Ar 1 、Ar 2 each independently selected from 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 group, substituted or unsubstituted C 2 -C 60 Heteroaryl, or a group consisting of the foregoing;
R 1 represents one or more to saturated substituted groups, said R 1 Each independently selected from hydrogen, deuterium, fluorine, hydroxy, 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 a group consisting of the foregoing.
The amine-based compound of the present invention is represented by the above chemical formula (I), and comprises a basic skeleton formed by combining a noradamantyl group and an amine group. The present inventors have found that the compound represented by the above-mentioned structure of formula (I) is electrochemically stable, has excellent hole mobility and electron blocking ability, and has a high glass transition temperature and excellent thermal stability, as compared with the structures B-1 to B-4 known in the prior art.
Thus, the amine-based compound of the present invention is excellent in hole transporting ability and electron blocking ability, and thus can be used as a material for any one of a hole injection layer, a hole transport auxiliary layer, and an electron blocking layer of an organic electroluminescent element. The material that can be used as any one of the hole transport auxiliary layer and the electron blocking layer is preferable, and the material that can be used as the electron blocking layer is more preferable.
Specifically, the compound represented by the formula (I) has a smaller refractive index, a stronger hole transporting ability and an electron blocking ability, and can exhibit a relatively high luminous efficiency and a high glass transition temperature, compared with the known cyclohexyl-containing derivatives B-1, B-2, adamantyl-containing B-3 and norbornyl-containing B-4, by optimizing the structure. Thus, when the amine-based compound represented by the formula (I) of the present invention is used for an organic electroluminescent element, not only excellent thermal stability and carrier transport ability, particularly electron blocking ability and light emitting ability, but also reduction in driving voltage of the element, improvement in efficiency, lifetime, and the like can be expected, and excellent efficiency increase due to triplet-triplet fusion effect can be exhibited due to high triplet energy level as a latest electron blocking layer material.
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, examples being, but not limited to, 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-trifluoroethoxyThio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, pentylenethio, cyclopentenyloxy, cyclopentenylenethio, hexenyloxy, hexenylenethio, cyclohexene oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The 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.
Preferably, the aryl, heteroaryl or heteroaryl group may be phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,a group, perylene group, fluoranthryl 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, benzocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group,dibenzocarbazolyl and 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, naphthooxazolyl, anthracenoxazolyl, 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, fluorored, 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, 5-tetrazinyl, purinyl, naphthyridinyl, indolizinyl, diazolyl, benzothiazyl or groups derived from these groups or from combinations of these groups.
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 amino compound is selected from any one of structures II-1 to II-8:
wherein R is 1 、L 1 、L 2 、L 3 、Ar 1 、Ar 2 The meaning of (C) is as defined for formula (I).
Further preferably, the R 1 Selected from hydrogen, deuterium, fluorine, nitrile groups, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or groups consisting of the foregoing.
Further, the R 1 Selected from hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, cyclopentyl, isopentyl, hexyl, cyclohexyl, cycloheptyl, 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 benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or a group consisting of the foregoing.
Further, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabenzoyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene, or a group consisting of the foregoing.
Preferably, the L 1 、L 2 、L 3 Each independently selected from a single bond, a group represented by the following III-1 to III-23, or a group consisting of:
wherein the dotted line represents the attachment site of the group.
In the present invention, the binding positions of the groups represented by the above formulas III-1 to III-23 are not limited, and may be ortho, meta, or para. L as described above 1 、L 2 、L 3 Can be each independently substituted with deuterium, halogen atom, nitrile group, C 1 -C 40 Alkyl, C 6 -C 60 Aryl, C 2 -C 60 The heterocyclic aryl group or one or more of the groups mentioned above are substituted, and when the substituent is plural, the plural substituents are the same or different from each other.
Preferably, the amino compound is selected from any one of structures II-1 to II-4;
R 1 hydrogen or deuterium; l (L) 1 Is a single bond, L 2 、L 3 、Ar 1 、Ar 2 The meaning of (a) is as defined for formula (I);
the invention adjusts the HOMO and LUMO energy levels by adjusting the position of the substituent and the type of the substituent, thereby having lower HOMO or higher LUMO, and enabling the organic electroluminescent element of the compound to have the highest hole-transporting property and electron-blocking property.
In addition, the amino compound of formula (I) of the present invention is prepared by introducing Ar, which may be substituted or unsubstituted, into the above basic skeleton 1 And Ar is a group 2 In particular, aryl and/or heteroaryl, the molecular weight of the compound is significantly increased, so that the glass transition temperature is increased, and thus, the compound has higher thermal stability than the prior luminescent materials. Therefore, the performance and lifetime characteristics of the organic electroluminescent element comprising the compound according to the present invention can be greatly improved. The organic electroluminescent element thus improved in performance and lifetime characteristics can eventually maximize the performance of the full-color organic light-emitting panel.
Preferably, the amine-based compound is selected from any one of the compounds represented by the following formulas D100 to D225:
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wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
The invention also provides an organic electroluminescent material, which comprises the amino compound as raw materials; the organic electroluminescent material has carrier transport capability and electron blocking capability.
The invention also provides application of the amino compound in preparation of an organic electroluminescent element.
The present invention further 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; wherein the material of at least one of the organic layer or the capping layer comprises the amine-based compound.
The organic electroluminescent element comprises a cathode, an anode and at least one light emitting layer. In addition to these layers, the organic electroluminescent element 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 amine-based compound 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 an amine-based compound 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 amine-based compound may preferably contain other compounds in addition to the amine-based compound. Treatment of the amine-based compounds of the present invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of the formulation 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 a mixture of any two or more 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; wherein the hole transport layer or the electron blocking layer comprises the amine-based compound.
More preferably, the electron blocking layer comprises the amine-based compound.
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.
Based on the technical scheme, the invention has the beneficial effects that:
according to the invention, the adamantyl is introduced into triarylamine molecules, so that the refractive index of the molecules can be reduced by increasing the proportion of saturated groups in the organic material, and the hole mobility and the electron blocking performance of the material are improved; the amine-based compound represented by formula (I) can be applied to an organic layer of an organic electroluminescent element due to hole mobility, electron blocking property, thermal stability, and low refractive index. In particular, when the amine-based compound represented by the formula (I) of the present invention is applied to an electron blocking layer or a hole transporting layer, an organic electroluminescent element having a lower driving voltage, higher efficiency and longer lifetime than conventional electron blocking materials 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 view of an organic light emitting device 100 prepared in test example 1 provided by the present invention. 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.
Fig. 2 is a schematic view of an organic light emitting device 200 having two light emitting layers prepared in test example 1 provided by the present invention. 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.
Reference numerals:
100: test example 1 organic light emitting device; 101: a substrate; 102: an anode; 103: a hole injection layer; 104: a hole transport layer; 105: an electron blocking layer; 106: a light emitting layer; 107: a hole blocking layer; 108: an electron transport layer; 109: an electron injection layer; 110: a cathode; seal 111: a cap layer (CPL);
200: test example 2 organic light emitting device; a 201 substrate; 202: an anode; 203: a hole injection layer; 204: a hole transport layer; 205: a first light emitting layer; 206: an electron transport layer; 207: a charge generation layer; 208: a hole injection layer; 209: a hole transport layer; 210: a second light emitting layer; 211: an electron transport layer; 212: an electron injection layer; 213: and a cathode.
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.
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 driving voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT 1931-C test was used.
Example 1
The present example provides an amine-based compound, compound D145, which is prepared by the steps of:
the first step: preparation of intermediate Int-1
Under the protection of nitrogen, 20.0mmol of 2-bromodiphenyl sub-2 is dissolved in 60mL of dry THF, the temperature is reduced to minus 80 ℃,22.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 10 minutes, 22.0mmol of noradamantan-9-one is added dropwise, stirring reaction is carried out for 1 hour, the temperature is raised to room temperature, 20mL of 2M aqueous hydrochloric acid solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phases are collected and combined, dried, filtered, the filtrate is concentrated and dried under reduced pressure, the residue is dissolved by 60mL of dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride diethyl ether solution is added dropwise, stirring reaction is carried out for 2 hours, the temperature is raised to room temperature, stirring reaction is carried out for 15 hours, 50mL of water is added, the organic phase is separated, drying, filtering is carried out, filtrate concentrating drying under reduced pressure is carried out, and silica gel column separation and purification are carried out, thus obtaining the compound Int-1, colorless oily substance with the yield of 85%.
And a second step of: preparation of intermediate Int-2
Under the protection of nitrogen, 79.4mmol of Int-1 is dissolved in 80mL of chloroform, 7.9mmol of anhydrous ferric bromide is added, stirring reaction is carried out for 10 minutes, 87.3mmol of bromine is added dropwise to the solution dissolved in chloroform, stirring reaction is carried out for 10 hours, heating is carried out for reflux reaction for 1 hour, cooling is carried out to room temperature, 50mL of saturated sodium bisulphite aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by chloroform, the organic phases are collected and combined, dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the compound Int-2 is obtained by separating and purifying by a silica gel column, and is a white solid with the yield of 95 percent.
And a third step of: preparation of Compound D145
24.0mmol of intermediate Int-2, 20.0mmol of sub-3, 30.0mmol of sodium tert-butoxide and 0.01mmol of Pd under the protection of nitrogen 2 (dba) 3 The catalyst, 0.02mmol Xantphos and 80mL toluene, heating to 100 ℃ and stirring to react for 15 hours,cooling to room temperature, adding 50mL of water for dilution, extracting with toluene, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound D145;
X:C(CH 3 ) 2 yellow solid, yield: 85%, MS (MALDI-TOF): m/z=632.3255 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.27(1H,s)；7.91～7.88(2H,m)；7.75～7.71(2H,m)；7.54～7.46(6H,m)；7.40～7.28(8H,m)；7.26～7.22(2H,m)；7.20～7.16(2H,m)；2.14～2.07(2H,m)；1.82～1.73(2H,m)；1.68(6H,s)；1.58～1.49(8H,m)。
X:C(Ph) 2 Yellow solid, yield: 83%, MS (MALDI-TOF): m/z=756.3566 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：7.91～7.86(4H,m)；7.75～7.71(2H,m)；7.55～7.46(7H,m)；7.42～7.32(6H,m)；7.28～7.21(6H,m)；7.17～7.06(8H,m)；2.14～2.07(2H,m)；1.82～1.72(2H,m)；1.59～1.49(8H,m)。
FR (9, 9-fluorenyl), yellow solid, yield: 81%, MS (MALDI-TOF): m/z=754.3408 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：7.92～7.85(4H,m)；7.75～7.71(2H,m)；7.54～7.45(6H,m)；7.42～7.33(6H,m)；7.29～7.21(5H,m)；7.19～7.12(6H,m)；7.17～7.15(2H,m)；2.14～2.07(2H,m)；1.82～1.72(2H,m)；1.59～1.49(8H,m)。
X: NPh, yellow solid, yield: 84%, MS (MALDI-TOF): m/z=681.3275 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.37(1H,s)；8.15(1H,s)；7.92～7.87(2H,m)；7.75～7.71(2H,m)；7.61～7.52(7H,m)；7.50～7.42(5H,m)；7.40～7.28(7H,m)；7.19～7.14(3H,m)；2.13～2.07(2H,m)；1.82～1.72(2H,m)；1.59～1.48(8H,m)。
Example 2
The present example provides an amine-based compound, compound D220, which is prepared by the steps of:
the first step: preparation of intermediate Int-3
Under the protection of nitrogen, 20.0mmol of Int-1' (prepared by the synthesis method of the first step of the example 1) is dissolved in 60mL of dry THF, cooled to minus 78 ℃,22.0mmol of 2.5M n-butyllithium n-hexane solution is dropwise added, stirring is carried out for 30 minutes, 24.0mmol of trimethyl borate is dropwise added, stirring is carried out for 1 hour, the temperature is raised to room temperature, 50mL of 3M dilute hydrochloric acid aqueous solution is dropwise added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phases are combined and dried, the filtrate is filtered, the filtrate is concentrated to dryness under reduced pressure, 50mL of petroleum ether is added for stirring and dispersing, the filtration is carried out, and a filter cake is washed by petroleum ether to obtain an intermediate Int-3, white solid with the yield of 80%.
And a second step of: preparation of intermediate Int-4
Under the protection of nitrogen, 22.0mmol of Int-3 is dissolved in 60mL of toluene, and then 20.0mmol of sub-4, 60.0mmol of anhydrous sodium carbonate and 0.02mmol of Pd (PPh) 3 ) 4 The catalyst, 30mL of ethanol and 30mL of water are stirred and heated to reflux for reaction for 15 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is washed by saturated brine, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-4 is obtained by separating and purifying by a silica gel column, and is a white solid with the yield of 84%.
And a third step of: preparation of Compound D220
Under the protection of nitrogen, 24.0mmol of Int-4 is dissolved in 60mL of toluene, and then 20.0mmol of sub-5, 30.0mmol of anhydrous sodium tert-butoxide and 0.02mmol of Pd are added 2 (dba) 3 The catalyst and 0.04mmol of 10% tri-tert-butyl phosphine toluene solution are heated to 100 ℃ and stirred for reaction for 15 hours, cooled to room temperature, added with 50mL of water for dilution, extracted with toluene,the organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure, and purified by silica gel column to give compound D220 as a yellow solid, yield: 87%, MS (MALDI-TOF): m/z=674.3721 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：7.86(1H,s)；7.76～7.71(3H,m)；7.65～7.62(1H,m)；7.59(1H,s)；7.55～7.44(7H,m)；7.42～7.35(4H,m)；7.28～7.22(3H,m)；7.14(1H,s)；7.08～7.05(2H,m)；7.02～6.99(1H,m)；2.49～2.41(1H,m)；2.13～2.07(2H,m)；1.93～1.78(8H,m)；1.69～1.46(10H,m)；1.39～1.30(2H,m)。
Examples 3 to 126
Referring to the above-described similar synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
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In the above embodiments, X is selected from one of the following structures:
* -and- (x) represents a bond.
Test 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 HI02 as hole injection layers respectively, wherein HI02 is 3% of HI01 by mass, and the vapor deposition film thickness is +.>
3) Continuously evaporating compound HTM as hole transport layer on the hole injection layer to obtain an evaporating film with a thickness of
4) The compounds represented by the formula (I) (D100 to D225 prepared in examples 1 to 126) of the present invention were further vapor-deposited as electron blocking layers on the hole transport layer to a vapor-deposited film thickness of
5) Continuously evaporating a compound BH035 as a main material and BD018 as a doping material on the electron blocking layer, wherein BD018 is 10% of BH035 by mass, and the film thickness of the organic light-emitting layer obtained by evaporation is
6) Continuously evaporating a layer of LiQ and a compound ET052 on the organic light-emitting layer as an electron transport layer of the element, wherein the compound ET052 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 the above test example 1 is as follows:
test 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 light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The method for producing the electroluminescent element 200 is described with reference to test example 1. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used.
Comparative example 1
This comparative example provides an amine-based compound H01 having the following structural formula:
according to the same procedure as in test example 1, the compound of formula (I) of the present invention in step 4) was replaced with H01 to obtain comparative element 1.
The organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in the above test examples 1 and 2 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: using a luminance meter at 10000cd/m 2 The luminance decay of the organic electroluminescent element was measured to be 9500cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 2 are relative data compared to comparative element 1.
TABLE 2
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As can be seen from Table 2, the OLED devices prepared from the compounds of the present invention have lower driving voltages than H01 under the same brightness, significantly improved current efficiency up to as much as 1.4 times that of the comparative devices, and significantly improved LT95% lifetime of the devices, indicating that the amine-based compounds of the present invention are excellent electron blocking layer materials.
The compound H01 of comparative example 1 is different from the amine-based compound of the present invention in that adamantane-containing H01 has a large steric hindrance, a high driving voltage, and low efficiency. In contrast, the compound of the present invention, after the introduction of the diamantane, reduces only one carbon compared with the adamantyl of H01, but reduces steric hindrance, improves hole transport performance and exciton blocking performance, and reduces the driving voltage significantly, so that the compound is more excellent in light emitting performance of the OLED element, and the 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.
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 amino compound is characterized by having a structure as shown in a formula (I):
wherein,
L 1 、L 2 、L 3 each independently selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heteroarylene, or a group consisting of the foregoing;
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted orUnsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 Heteroaryl, or a group consisting of the foregoing;
R 1 represents one or more to saturated substituted groups, said R 1 Each independently selected from hydrogen, deuterium, fluorine, hydroxy, 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 a group consisting of the foregoing.
2. The amine-based compound of claim 1, wherein the amine-based compound is selected from any one of structures II-1 to II-8:
wherein R is 1 、L 1 、L 2 、L 3 、Ar 1 、Ar 2 The meaning of (C) is as defined for formula (I).
3. Root of Chinese characterAn amine-based compound according to claim 1 or 2, wherein R 1 Selected from hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, cyclopentyl, isopentyl, hexyl, cyclohexyl, cycloheptyl, 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 benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or a group consisting of the foregoing groups;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabenzoyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene, or a group consisting of the foregoing.
4. An amine-based compound according to any one of claims 1 to 3, wherein L 1 、L 2 、L 3 Each independently selected from a single bond, a group represented by the following III-1 to III-23, or a group consisting of:
wherein the dotted line represents the attachment site of the group.
5. The amine-based compound according to claim 2, wherein the amine-based compound is selected from any one of structures II-1 to II-4;
R 1 hydrogen or deuterium; l (L) 1 Is a single bond, L 2 、L 3 、Ar 1 、Ar 2 The meaning of (a) is as defined for formula (I);
6. the amine-based compound according to any one of claims 1 to 5, wherein the amine-based compound is selected from any one of the compounds represented by the following formulas D100 to D225:
wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
7. Use of an amine-based compound 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; wherein the material of at least one of the organic layer or the capping layer comprises the amine-based compound of 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; wherein the hole transport layer or the electron blocking layer comprises the amine-based compound according to any one of claims 1 to 6.
10. A consumer electronic device characterized in that it comprises an organic electroluminescent element as claimed in claim 8 or 9.
CN202310933472.1A 2023-07-27 2023-07-27 Amine compound, organic electroluminescent element and consumer electronic device Pending CN117069596A (en)

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