CN117105893A - Amino compound containing trans-cyclohexyl and application thereof - Google Patents

Amino compound containing trans-cyclohexyl and application thereof Download PDF

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CN117105893A
CN117105893A CN202310937274.2A CN202310937274A CN117105893A CN 117105893 A CN117105893 A CN 117105893A CN 202310937274 A CN202310937274 A CN 202310937274A CN 117105893 A CN117105893 A CN 117105893A
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substituted
unsubstituted
group
trans
cyclohexyl
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曹建华
李瑞山
王振宇
李利铮
王志杰
张九敏
姚宇
刘子威
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to an amino compound containing trans-cyclohexyl and an electronic element thereofParts and electronic devices. The structural formula of the amino compound containing the trans-cyclohexyl is shown as a formula (I); the compound shown in the formula (I) provided by the invention has at least one trans-cyclohexyl structure. 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

Amino compound containing trans-cyclohexyl and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an amino compound containing trans-cyclohexyl and application thereof in organic light-emitting elements and electronic devices.
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.
Based on the reasons, the invention introduces the specific trans-cyclohexyl of the liquid crystal molecules into the triarylamine to improve the proportion of saturated groups in the organic material, reduce the refractive index of the molecules, and improve the hole mobility and the electron blocking performance of the material.
Disclosure of Invention
The invention aims to provide an amino compound containing trans-cyclohexyl, which can reduce refractive index, improve material thermal stability and carrier conveying capacity, and can remarkably reduce driving voltage, improve luminous efficiency and prolong service life of an organic electroluminescent element prepared by using the amino compound containing trans-cyclohexyl; it is a further object of the present invention to provide the use of the compounds.
Specifically, the invention provides the following technical scheme:
the invention provides an amino compound containing trans-cyclohexyl, which has a structural formula shown in a formula (I):
wherein,
L 1 、L 2 、L 3 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
Ar 1 、Ar 2 、Ar 3 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group, a substituted or unsubstituted trans-cyclohexyl group, and is substituted at Ar 1 、Ar 2 、Ar 3 Containing at least one substituted or unsubstituted trans-cyclohexyl group of formula (II);
R 1 free fluorine, nitrile group, 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 Silicon carbideAlkyl, substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
R 2 represents one or more to saturated substituents, 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 groups;
* -representing the position of the bond.
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.
The amine compound having a trans-cyclohexyl group according to the present invention is represented by the above-mentioned chemical formula (I), and comprises a basic skeleton formed by the combination of the formula (I) with at least one group of the formula (II). The compound represented by the formula (I) of the present invention 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 conventionally known B-1 to B-3 structures.
Accordingly, the amine-based compound containing a trans-cyclohexyl group 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) of the present invention 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, as compared with the known cyclohexyl group-containing derivatives B-1, B-2 and B-3, by a plurality of substituted or unsubstituted trans-cyclohexyl derivatives. Thus, when the amine compound having a trans-cyclohexyl group represented by the formula (I) of the present invention is used for an organic electroluminescent element, not only excellent thermal stability and carrier transporting ability, particularly electron blocking ability and light emitting ability, but also reduction in driving voltage of the element, improvement in efficiency, lifetime, etc. can be expected, and excellent efficiency increase due to triplet-triplet fusion effect can be exhibited as a latest electron blocking layer material due to high triplet energy level.
The amine compound having a trans-cyclohexyl group represented by the formula (I) of the present invention is prepared by reacting an amine compound having a trans-cyclohexyl group represented by the formula (I) of the present invention with a compound having a substituent R 1 、R 2 Cyclohexyl and Ar of (2) 1 L 1 NL 2 Ar 2 L 3 Ar 3 By adjusting the HOMO and LUMO levels according to the kind of the substituent, it is possible to have a lower HOMO or a higher LUMO, and it is possible to most exhibit high hole transport property and electron blocking property in an organic electroluminescent element using such a compound.
In addition, the amine compound containing trans-cyclohexyl group represented by the formula (I) of the present invention is obtained by introducing Ar of various substituents or unsubstituted groups into the above basic skeleton 1 、Ar 2 、Ar 3 In particular aryl and/or heteroaryl, the molecular weight of the compounds is significantly increased, and the glass transition temperature is thereby increased, in comparison withThe prior luminescent material has higher thermal stability. 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.
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 with oxygen, sulfur, halogen atoms, as non-limiting examples, alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butylenethio, butyleneoxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene thio, acetylenyloxy, acetylenylthio, propynyloxy, butynylthio, pentynyloxy, pentynylthio, hexyloxy, hexylynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The heterocycloalkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a atomic number of 3 to 40. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine, and the like are given.
Condensed ring aryl used in the present invention means aromatic hydrocarbon having 10 to 60 carbon atoms which is obtained by combining two or more ringsA monovalent functional group obtained by removing one hydrogen atom. 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 is preferably selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, pyrenyl,a group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, iD]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxaoxazolyl, 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, phenothiazinyl, erythrozinyl, naphthyridinyl, 1,2, 3-triazolyl, 1, 2-triazolyl, 4-naphthyridinyl Triazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.
Preferably, the amine compound having a trans-cyclohexyl group represented by the formula (I) of the present invention is selected from the group consisting of the structures shown below:
wherein R is 1 、R 2 、L 1 、L 2 、L 3 、Ar 2 、Ar 3 The meaning of (a) is as defined for formula (I);
x is selected from O, S, CR 3 R 4 、SiR 3 R 4 Or NR (NR) 5 ；
R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 2 -C 40 Alkenyl, 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 Arylamine group, substituted or unsubstituted C 2 -C 60 Heteroaryl group, R 3 And R is 4 Optionally joined or fused to form a substituted or unsubstituted ring;
R 5 Selected from the group consisting of substituted and unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group.
Further, the R 1 Selected from fluorine, nitrile groups, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl groups.
Further, the R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, 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 An arylamine group.
Preferably, said R 1 Selected from the group consisting of 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 dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
Preferably, said R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl.
Further, the Ar 1 、Ar 2 、Ar 3 、R 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 naphthyl, substituted or unsubstituted phenanthryl, andsubstituted or unsubstituted triphenylene, 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 dibenzothienyl.
According to an embodiment of the invention, the R 2 、R 3 、R 4 Each independently selected from hydrogen, methyl, phenyl or 9, 9-fluorenyl.
According to an embodiment of the invention, the R 1 Selected from the group consisting of nitrile, methyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
Preferably, the L 1 、L 2 、L 3 Each independently selected from a single bond or from the group consisting of groups III-1 to III-23:
wherein the dotted line represents the linking site of the group, and the binding site of the groups represented by the above formulas III-1 to III-23 is not limited, and may be any of ortho-, meta-, and para-ones. L as described above 1 、L 2 、L 3 Can be independently selected from deuterium, halogen atom, nitrile group, C 1 -C 40 Alkyl, C 6 -C 60 Aryl and C 2 -C 60 When the substituent is plural, it is preferable that the plural substituents are the same or different from each other.
In the present invention, the term "substituted or unsubstituted" means that the compound is selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, and C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Cycloalkyl, C 3 -C 40 Cycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Aryl sulfide group and C 2 -C 60 More than 1 substituent in the heterocyclic aryl group is substituted or unsubstituted, or a substituent which is formed by connecting more than 2 substituents in the above exemplified substituents is substituted or unsubstituted.
Preferably, the amine compound containing a trans-cyclohexyl group is selected from compounds represented by the following formulas D100 to D207:
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 with low refractive index, which comprises the amino compound containing trans-cyclohexyl; the organic electroluminescent material comprising the amine-based compound having trans-cyclohexyl group of the present invention has a carrier transporting ability and an electron blocking ability.
The invention also provides application of the amino compound containing the trans-cyclohexyl in preparing 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 amine-based compound containing a trans-cyclohexyl group 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 amine compound containing a trans-cyclohexyl group 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 compound comprising at least one trans-cyclohexyl group of the invention as indicated above. 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 containing a trans-cyclohexyl group may preferably contain other compounds. Treatment of the amine-based compounds containing trans-cyclohexyl groups of the present invention from the liquid phase, for example by spin coating or by printing, 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 mixtures of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
Further, the hole transporting layer, hole transporting layer or electron blocking layer comprises the amine compound containing trans-cyclohexyl group of the present invention.
Still further, the electron blocking layer comprises the amine-based compound containing a trans-cyclohexyl group of the present invention.
The invention also provides a consumer electronic device comprising the organic electroluminescent element, wherein the consumer electronic device can be one of the following devices: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
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 amine compound containing trans-cyclohexyl group represented by the formula (I) provided by the invention 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 compound having a trans-cyclohexyl group 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
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
In the description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower", etc. are based on the orientation or positional relationship shown in the drawings, are merely for convenience of description and to simplify the description, and are not indicative or implying that the apparatus or elements in question must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the present invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the examples below, unless otherwise specified, are all commercially available, and the percentages, such as the percentages without otherwise specified, are all mass percentages.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing using a spectrum scanner PhotoResearchPr-715;
current density and driving voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT1931-C test was used.
Example 1
A process for the preparation of compound D156 comprising the steps of:
the first step: preparation of intermediate Int-1
Under the protection of nitrogen, 20.0mmol of trans-sub-1, 24.0mmol of sub-2, 30.0mmol of sodium tert-butoxide and 0.01mmol of Pd 2 (dba) 3 Catalyst, 0.02mmol Xantphos and 80mL toluene, raise the temperature to 100 ℃ and stir and react for 15 hours, cool to room temperature, add 50mL water to dilute, extract with toluene, collect the organic phase, dry, filter, the filtrate is concentrated dry under reduced pressure, separate and purify with silica gel column, get compound Int-1, yellow solid;
And a second step of: preparation of Compound D156
Under the protection of nitrogen, 20.0mmol of intermediate Int-1, 24.0mmol of sub-3, 30.0mmol of sodium tert-butoxide and 0.01mmol of Pd 2 (dba) 3 Catalyst, 0.04mmol of 10% tri-tert-butyl phosphine toluene solution and 80mL of toluene, heating to 100 ℃, stirring and reacting 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 D156;
compound D156-1:
white solid, yield: 85%, MS (MALDI-TOF): m/z=930.5521 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.21(1H,s)；7.92～7.90(1H,d)；7.75～7.71(2H,m)；7.54～7.51(2H,m)；7.38～7.31(5H,m)；7.19～7.16(3H,m)；7.09～7.06(2H,m)；6.98～6.93(2H,m)；2.74～2.69(1H,m)；1.91～1.58(13H,m)；1.54～1.47(2H,m)；1.33～0.94(11H,m)。
Compound D156-2:
white solid, yield: 83%, MS (MALDI-TOF): m/z=738.3672 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.21(1H,s)；7.96～7.93(1H,m)；7.90～7.86(4H,m)；7.54～7.50(3H,m)；7.46～7.33(11H,m)；7.21～7.15(3H,m)；7.05～7.01(2H,m)；6.97～6.95(1H,d)；2.74～2.69(1H,m)；1.91～1.58(7H,m)；1.54～1.47(2H,m)；1.33～0.94(11H,m)。
Compound D156-3:
a white solid was used as a solid,yield: 86%, MS (MALDI-TOF): m/z=815.4373 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.16(1H,s)；7.94～7.91(1H,m)；7.52～7.41(7H,m)；7.38～7.28(10H,m)；7.26～7.24(2H,d)；7.19～7.13(4H,m)；7.10～7.06(4H,m)；7.01～6.97(4H,m)；2.74～2.69(1H,m)；1.91～1.58(7H,m)；1.54～1.47(2H,m)；1.33～0.94(11H,m)。
Example 2
A process for the preparation of compound D167 comprising the steps of:
the first step: preparation of intermediate Int-2
Under the protection of nitrogen, 20.0mmol of sub-4 is dissolved in 60mL of dichloromethane, then 2.0mmol of p-toluenesulfonic acid and 2.0mmol of anhydrous ferric chloride are added, the temperature is reduced to 0 ℃, 22.0mmol of bromine is added dropwise into the solution dissolved in dichloromethane, the reaction is stirred for 2 hours, the temperature is raised to room temperature, 50mL of saturated sodium bisulphite aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phases are combined and dried, the filtration and the concentration of the filtrate under reduced pressure are carried out, the separation and the purification are carried out by using a silica gel column, and the intermediate Int-2 is obtained, and the yield is 85% -95%.
And a second step of: preparation of intermediate Int-3
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 50mL of dry THF, the temperature is reduced to minus 78 ℃,22.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, the mixture is stirred and reacted for half an hour, then 24.0mmol of 4-cyclohexylcyclohexanone solution dissolved in THF is added dropwise, the mixture is stirred and reacted for 1 hour, the temperature is raised to room temperature, 50mL of 1M dilute hydrochloric acid aqueous solution is added dropwise, the ethyl acetate is used for extraction, the organic phase is washed with saturated salt water, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the silica gel column is separated and purified to obtain the compound Int-3, the yield is 80% -90%.
And a third step of: preparation of intermediate Int-4
Under the protection of nitrogen, 22.0mmol of Int-3 is dissolved in 150mL of dichloromethane, the temperature is reduced to minus 5 ℃, 60.0mmol of triethylsilane is added, 114.0mmol of boron tribromide is added dropwise, the temperature is raised to room temperature, stirring is carried out for 15 hours, 100mL of ice water solution is added, an organic phase is separated, the aqueous phase is extracted by dichloromethane, the organic phase is washed by water, saturated sodium bicarbonate aqueous solution and dried, the filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-4 is obtained by separating and purifying by a silica gel column, and the yield is 90% -95%.
Mixing 0.4mmol of anhydrous aluminum trichloride with 50mL of dried dichloromethane under the protection of nitrogen, adding 0.4mmol of anhydrous lithium chloride, cooling to 5 ℃, dropwise adding 20.0mmol of solution of the prepared cis-trans mixture Int-4 dissolved in dichloromethane, stirring for reacting for 12 hours, pouring the reaction solution into a water solution containing 100mL of 2M diluted hydrochloric acid and 50g of ice, separating an organic phase, extracting the water phase with dichloromethane, combining the organic phases, washing the organic phases with water to be neutral, drying the organic phases, concentrating under reduced pressure to dryness, decoloring the residue with a short silica gel column, eluting with petroleum ether, and recrystallizing with ethanol to obtain a trans intermediate Int-4 with the trans content of 99.5% -99.9% by HPLC (high performance liquid chromatography): 80% -85%.
Fourth step: preparation of intermediate Int-5
Under the protection of nitrogen, 20.0mmol of trans-Int-4 and 60.0mmol of pyridine are dissolved in 80mL of dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of trifluoromethanesulfonic anhydride is added dropwise, the mixture is stirred and reacts for 2 hours, the temperature is raised to room temperature, 50mL of water is added, an organic phase is separated, the water phase is extracted by dichloromethane, the organic phase is washed by dilute hydrochloric acid aqueous solution and washed by water, dried and filtered, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-5 is obtained by separating and purifying by a silica gel column, and the yield is 90% -95%.
Fifth step: preparation of Compound D167
Under the protection of nitrogen, 24.0mmol of Int-5 is dissolved in 60mL of toluene, and then 20.0mmol of sub-5, 30.0mmol of anhydrous tertiary sodium butoxide and 0.02mmol of Pd are added 2 (dba) 3 Catalyst, 0.04mmol of 10% tri-tert-butyl phosphine toluene solution, heating to 100 ℃ and stirring for reaction 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 D167;
compound D167-1:
white solid, yield: 78%, MS (MALDI-TOF): m/z=840.4509 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.23(1H,s)；7.96～7.90(4H,m)；7.75～7.71(2H,m)；7.52(1H,s)；7.50～7.39(9H,m)；7.34(1H,s)；7.31～7.22(5H,m)；7.19～7.14(4H,m)；7.12～7.07(3H,m)；3.05～2.98(1H,m)；1.90～1.48(17H,m)；1.32～0.98(9H,m)。
Compound D167-2:
white solid, yield: 82%, MS (MALDI-TOF): m/z=718.4347 [ m+h ] ] + ； 1 HNMR(δ、CDCl 3 )：8.26(1H,s)；8.21(1H,s)；7.92～7.90(1H,d)；7.76～7.73(2H,m)；7.57～7.53(3H,m)；7.50～7.45(2H,m)；7.39～7.33(5H,m)；7.31～7.26(4H,m)；7.24～7.20(2H,m)；7.14～7.11(1H,d)；3.05～2.98(1H,m)；1.90～1.48(23H,m)；1.32～0.98(9H,m)。
Compound D167-3:
white solid, yield: 80%, MS (MALDI-TOF): m/z=784.4456 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：7.98(1H,s)；7.90～7.86(2H,m)；7.76～7.73(2H,m)；7.53～7.46(5H,m)；7.40～7.31(7H,m)；7.25～7.21(2H,m)；7.14～7.11(1H,d)；7.06～7.04(2H,d)；2.74～2.65(1H,m)；2.24～1.98(12H,m)；1.90～1.37(13H,m)；1.33～0.94(9H,m)。
Example 3
A process for the preparation of compound D206 comprising the steps of:
the first step: preparation of intermediate Int-6
Under the protection of nitrogen, 22.0mmol of M-dibromobenzene is dissolved in 60mL of dry THF, the temperature is reduced to minus 78 ℃, 24.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 10 minutes, then 20.0mmol of 9-fluorenone solution dissolved in THF is added dropwise, the temperature is raised to room temperature, stirring reaction is carried out for 2 hours, 50mL of 2M dilute hydrochloric acid aqueous solution is added dropwise, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtration and concentration drying of filtrate under reduced pressure are carried out, and intermediate Int-6, yellow oily matter is obtained by separating and purifying by a silica gel column, and the yield is 86%.
And a second step of: preparation of intermediate Int-7
Under the protection of nitrogen, 20.0mmol of Int-6 and 60.0mmol of trans-sub-7 are dissolved in 80mL of dry 1, 2-dichloroethane, 20.0mmol of concentrated sulfuric acid is added dropwise, the temperature is raised to reflux and stirring for reaction for 15 hours, potassium tert-butoxide is added in batches until the reaction solution is alkaline, 100mL of ice water solution is added, an organic phase is separated, the aqueous phase is extracted by methylene dichloride, the organic phases are combined and dried, the filtration and the concentration and drying of the filtrate under reduced pressure are carried out, and the separation and the purification of the silica gel column are carried out to obtain an intermediate Int-7, white solid with the yield of 81 percent.
And a third step of: preparation of Compound D206
Under the protection of nitrogen, 24.0mmol of Int-7 is dissolved in 60mL of toluene, and then 20.0mmol of sub-8, 30.0mmol of sodium tert-butoxide and 0.02mmol of Pd are added 2 (dba) 3 Catalyst, 0.04mmol of 10% tri-tert-butyl phosphine toluene solution, heating to 100 ℃ and stirring for reaction 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 D206;
compound D206-1:
white solid, yield: 87%, MS (MALDI-TOF): m/z=802.3983 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.20(1H,s)；7.96(1H,s)；7.89～7.86(2H,m)；7.76～7.73(2H,m)；7.54～7.46(5H,m)；7.44～7.34(9H,m)；7.32～7.29(2H,m)；7.27～7.21(5H,m)；7.17～7.13(2H,m)；6.98～6.95(2H,m)；6.93～6.90(1H,m)；2.75～2.66(1H,m)；1.89～1.71(9H,m)；1.68～1.52(3H,m)；1.37～1.08(6H,m)。
Compound D206-2:
white solid, yield: 82%, MS (MALDI-TOF): m/z=877.4535 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.16(1H,s)；7.89～7.86(2H,m)；7.75～7.72(2H,m)；7.53～7.42(8H,m)；7.40～7.22(16H,m)；7.19～7.13(3H,m)；6.97～6.94(1H,m)；6.81～6.78(1H,m)；6.55～6.52(1H,d)；2.75～2.66(1H,m)；1.89～1.71(9H,m)；1.68～1.52(3H,m)；1.37～1.08(6H,m)。
Examples 4 to 108
Referring to the above-described similar synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
In the above embodiments, each t— is independently selected from one of the structures shown below:
* -x— each independently selected from one of the following structures:
* -and- (x) represents a bond.
Example 109
As shown in fig. 1, an OLED element 100 of the present embodiment is a top emission light element, and includes a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, and a cathode 110 disposed on the electron injection layer 109 and a capping layer 111 disposed on the cathode, wherein the method for manufacturing the OLED element excluding the hole blocking layer 107 includes the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, depositing metallic silver as an anode layer on the ITO film, the thickness of the deposited film beingContinuing to evaporate the compounds HI01 and HI02 respectively as hole injection layers, wherein HI02 is HI01 mass% and a vapor deposition film thickness of +.>
3) Continuously evaporating compound HTM as hole transport layer on the hole injection layer to obtain an evaporating film with a thickness of
4) Continuing to vapor deposit the compound represented by the formula (I) of the present invention as an electron blocking layer on the hole transport layer, the vapor deposition film thickness being
5) Continuously evaporating a compound RH015 serving as a main material and RD015 serving as a doping material on the electron blocking layer, wherein RD015 is 5% of the RH015 by mass, and the film thickness of the organic light-emitting layer obtained by evaporation serving as an organic light-emitting layer of the element is
6) Continuously evaporating a layer of LiQ and a compound ET028 on the organic light-emitting layer as an electron transport layer of the element, wherein the compound ET028 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, and evaporating filmThickness isThe OLED element provided by the invention is obtained.
The structure of the compound used in example 109 above is as follows:
example 110
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. Electroluminescent element 200 was prepared by a similar method as in example 109.
Comparative example 1
By following a procedure analogous to example 109 substituting the compound of formula (I) according to the invention containing trans-cyclohexyl in step 4) with H01, comparative element 1 is obtained;
comparative example 2
By following a procedure analogous to example 109 substituting the trans-cyclohexyl group-containing compound of formula (I) of the invention in step 4) with H02, comparative element 2 is obtained;
The organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent elements prepared in examples 109 and 110 and comparative examples 1 and 2 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
In the above table, me is methyl, ph is phenyl, FR is 9, 9-fluorenyl, and Ad is adamantyl;
CPPT is:
NPT is:
as can be seen from table 2, the OLED element prepared from the compound of the present invention has a lower driving voltage than H01 and H02 under the same brightness, a significantly improved current efficiency up to as much as 1.2 times that of the comparative element, and a significantly improved LT95% lifetime of the element, indicating that the compound containing trans-cyclohexyl of the present invention is an excellent electron blocking layer material.
The compound H01 in comparative example 1 and the compound H02 in comparative example 2 are different from the trans-cyclohexyl compound of the present invention in that a plurality of cyclohexyl-substituted H01 and H02 lower the refractive index but have high driving voltage and low efficiency. However, the compound of the present invention has a reduced number of alkyl substituents relative to H01 and H02 after introducing trans-cyclohexyl, but the total number of alkyl groups (substituted cyclohexyl) is increased, the refractive index of the molecule is reduced, the driving voltage is reduced significantly, and the charge blocking performance is improved, so that the compound is more excellent in the light emitting performance of the OLED element, and the element performance is improved significantly.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (10)

1. An amino compound containing trans-cyclohexyl is characterized in that the structural formula is shown as a formula (I):
wherein,
L 1 、L 2 、L 3 each independently selected from the group consisting of single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroarylenes;
Ar 1 、Ar 2 、Ar 3 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group, a substituted or unsubstituted trans-cyclohexyl group, and is substituted at Ar 1 、Ar 2 、Ar 3 Containing at least one substituted or unsubstituted trans-cyclohexyl group of formula (II);
R 1 selected from fluorine, nitrile groups, 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 groups;
R 2 represents one or more to saturated substituents, 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, takingSubstituted 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 groups;
* -representing the position of the bond.
2. The trans-cyclohexyl containing amine compound of claim 1, wherein the trans-cyclohexyl containing amine compound is selected from the group consisting of:
wherein R is 1 、R 2 、L 1 、L 2 、L 3 、Ar 2 、Ar 3 The meaning of (a) is as defined for formula (I);
x is selected from O, S, CR 3 R 4 、SiR 3 R 4 Or NR (NR) 5 ；
R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 2 -C 40 Alkenyl, 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 Arylamine group, substituted or unsubstituted C 2 -C 60 Heteroaryl group, R 3 And R is 4 Can optionally beJoined or fused to form a substituted or unsubstituted ring;
R 5 Selected from the group consisting of substituted and unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group.
3. The amine compound having a trans-cyclohexyl group as claimed in claim 2, wherein R 1 Selected from fluorine, nitrile groups, substituted or unsubstituted C 1 -C 40 Alkyl, substituted or unsubstituted C 3 -C 40 Cycloalkyl groups;
R 2 、R 3 、R 4 each independently selected from the group consisting of hydrogen, deuterium, 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 An arylamine group.
4. The amine compound having a trans-cyclohexyl group as claimed in claim 2, wherein R 1 Selected from the group consisting of 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl;
R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl;
Ar 1 、Ar 2 、Ar 3 、R 5 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 dibenzothiophenyl.
5. The amine compound having a trans-cyclohexyl group as claimed in claim 1, wherein L 1 、L 2 、L 3 Each independently selected from a single bond or from the group consisting of groups III-1 to III-23:
wherein the dotted line represents the attachment site of the group.
6. The amine compound having a trans-cyclohexyl group according to any one of claims 1 to 5, wherein the amine compound having a trans-cyclohexyl group is selected from the group consisting of compounds represented by the following formulas D100 to D207:
Wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
7. Use of an amine compound containing a trans-cyclohexyl group as claimed in 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; a material of at least one of the organic layer or the capping layer includes the amine-based compound containing a trans-cyclohexyl group as claimed in any one of claims 1 to 6.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer;
the hole transporting layer or the electron blocking layer comprises the trans-cyclohexyl group-containing amine-based compound 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.
CN202310937274.2A 2023-07-28 2023-07-28 Amino compound containing trans-cyclohexyl and application thereof Pending CN117105893A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012222255A (en) * 2011-04-12 2012-11-12 Fujifilm Corp Organic electroluminescent element, material and film for organic electroluminescent element, and manufacturing method for organic electroluminescent element
CN113717058A (en) * 2021-09-17 2021-11-30 长春海谱润斯科技股份有限公司 Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012222255A (en) * 2011-04-12 2012-11-12 Fujifilm Corp Organic electroluminescent element, material and film for organic electroluminescent element, and manufacturing method for organic electroluminescent element
CN113717058A (en) * 2021-09-17 2021-11-30 长春海谱润斯科技股份有限公司 Triarylamine compound containing fluorene derivative group and organic electroluminescent device thereof

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