CN115536535B - Fluorene derivative and organic light-emitting element comprising same - Google Patents

Fluorene derivative and organic light-emitting element comprising same Download PDF

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CN115536535B
CN115536535B CN202211211985.3A CN202211211985A CN115536535B CN 115536535 B CN115536535 B CN 115536535B CN 202211211985 A CN202211211985 A CN 202211211985A CN 115536535 B CN115536535 B CN 115536535B
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fluorene derivative
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CN115536535A (en
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张海威
李程辉
邸庆童
张昊
边坤
刘殿君
郭文龙
王振宇
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The present invention relates to the technical field of organic electroluminescent materials, and more particularly, to a fluorene derivative and an organic light-emitting device including the fluorene derivative. The fluorene derivative has a structure shown in a formula (I), so that the plane conjugation capability of the fluorene derivative is improved, and the thermal stability of the material and the capability of transporting carriers are improved; the fluorene derivative 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

Fluorene derivative and organic light-emitting element comprising same
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a fluorene derivative, an organic material and application thereof in an organic electroluminescent element.
Background
In recent years, optoelectronic devices based on organic materials have become more popular, and the inherent flexibility of organic materials compared with inorganic materials makes them suitable for fabrication on flexible substrates, and various optoelectronic products can be designed and produced according to requirements. Presently known organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like; among them, the OLED has advantages of self-luminescence, high contrast, wide color gamut, flexibility, low power consumption, etc., and has been developed particularly rapidly, and has been successfully commercialized, and is widely used in various fields such as flexible display, flat panel display, and solid state lighting.
The OLED element comprises a cathode, an anode and an organic film structure arranged between the two electrodes, wherein the core of the OLED element is a film structure containing various organic functional materials, and common organic functional materials are as follows: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (doping material), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light. In an OLED element, the organic functional material directly affects the light emitting performance of the device.
The hole transport material is used as a general layer material of the OLED element, and the voltage, efficiency, service life and other core indexes of the element are affected by adjusting the injection and transport properties of holes. At present, hole transport materials for commercial mass production are mainly aromatic amine materials, and due to different material collocations of devices, the problems of various aspects such as efficiency, service life and cost of OLED products cannot be completely solved by the materials and element structures used at present.
In order to overcome the above-described problems, there is a continuing need for the development of a more stable and effective substance that can be used as a hole material in an organic electroluminescent element, in order to further improve the characteristics of the organic electroluminescent element.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a fluorene derivative which has good photoelectric characteristics, and an organic electroluminescent element prepared by using the fluorene derivative, in particular an element used as a hole transport material and/or an electron blocking material, can obviously reduce driving voltage, improve luminous efficiency and prolong service life; another object of the present invention is to provide the use of the fluorene derivative in an organic electroluminescent element.
Specifically, the invention provides the following technical scheme:
The invention provides a fluorene derivative, which has a structural formula shown in a formula (I):
Wherein two adjacent groups W 1 and W 2 represent groups of formula (II) below, and "≡" indicates adjacent groups W 1 and W 2 in formula (I);
Each R 1、R2、R3、R4、R5 is independently selected from the group consisting of hydrogen, deuterium, alkyl of C 1-C40, cycloalkyl of C 3-C40, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 6-C60 fused ring aryl, substituted or unsubstituted C 6-C60 arylamine group, substituted or unsubstituted C 2-C60 heteroaryl;
Ar 1、Ar2 is each independently selected from the group consisting of substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 6-C60 fused ring aryl, substituted or unsubstituted C 6-C60 arylamine group, or substituted or unsubstituted C 2-C60 heterocyclic aryl;
m is selected from integers of 0 to 5;
L 1 is selected from a single bond, a substituted or unsubstituted C 6-C60 arylene, or a substituted or unsubstituted C 2-C60 heteroarylene.
In the present invention, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
Preferably, each of the R 3、R4、R5 is hydrogen or deuterium; each R 1、R2 is independently selected from the group consisting of alkyl of C 1-C40, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 2-C60 heteroaryl.
Preferably, each Ar 1、Ar2 is independently selected from the group consisting of substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 6-C60 arylamine, or substituted or unsubstituted C 2-C60 heteroaryl.
Preferably, m is 0, 1 or 2.
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 in the sense of the present invention contains 1 to 40 carbon atoms and wherein the individual hydrogen atoms or the-CH 2 -groups may also be substituted straight-chain alkyl or branched alkyl groups; 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 groups, preferably alkyl groups having 1 to 40 carbon atoms, refer to groups in which a separate hydrogen atom or-CH 2 -group is replaced by an oxygen, sulfur, halogen atom, 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 -groups may be replaced by the above groups; 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.
Alkoxy as used herein refers to a monovalent functional group represented by RO -, where R is an alkyl group having 1 to 40 carbon atoms and may comprise a linear, branched or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, cyclopentoxy, cyclohexyloxy, and the like.
The aryloxy group used in the present invention means a monovalent functional group represented by R 'O -, and 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, said aryl, heteroaryl, in particular groups derived from: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, cis-or trans-indolocarbazolyl group, trimeric indenyl group, heterotrimeric indenyl group, spiro-isothioindenyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, indolyl group, isoindolyl group, carbazolyl group, pyridyl group, quinolinyl group, isoquinolinyl group, acridinyl group, phenanthridinyl group, benzo [5,6] quinolinyl group, benzo [6,7] quinolinyl group, benzo [7,8] quinolinyl group, phenothiazinyl group, phenoxazinyl group, etc pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthraceneoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthryl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, erythrocyclyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthroline, pyrrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.
Further, each of the R 1、R2 is independently selected from the group consisting of methyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
Further, each of the Ar 1、Ar2 is independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetrabiphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group.
Preferably, L 1 is selected from a single bond or a group consisting of the groups shown in III-1 to III-23 below:
Wherein the dotted line represents the attachment site of the group.
In the present invention, the term "substituted or unsubstituted" means that the compound is substituted or unsubstituted with 1 or more substituents selected from hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, amino, amidino, hydrazino, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, alkyl of C 1-C40, alkenyl of C 2-C40, alkynyl of C 2-C40, alkoxy of C 1-C40, cycloalkyl of C 3-C40, cycloalkenyl of C 3-C40, aryl of C 6-C60, aryloxy of C 6-C60, arylene sulfide of C 6-C60 and heterocyclic aryl of C 2-C60, or the substituent bonded with 2 or more substituents exemplified above.
Preferably, the fluorene derivative has a structural formula selected from the group consisting of D01 to D201:
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Wherein-t— is selected from-O-, S-, or one of the following structures:
Preferably, the t— is selected from one of the following structures:
Further, the t— is selected from one of the following structures:
the above-mentioned ×— and — represent the connecting bonds.
The invention provides a synthetic route of a compound shown in a formula (I), which is shown as follows:
wherein X 1、X2 represents I, br, cl, OTf, CO 2 H, boric acid or pinacol borate; the other symbols used are as defined above.
The raw materials for synthesizing the compound shown in the formula (I) can be purchased through commercial paths, and the method principles, the operation process, the conventional post-treatment, the column purification, the recrystallization purification and other means are well known to the synthesis personnel in the field, so that the synthesis process can be completely realized to obtain the target product.
Specifically, the compound of formula (I) is prepared from X 1 substituted I-0 through SUZUKI coupling reaction, substitution reaction, condensation reaction, buchwald-Hartwig coupling reaction and the like. Intermediate Ar 1Ar2N-(L1)mB(OH)2 or Ar 1Ar2 NH was prepared by palladium catalyzed or base catalyzed coupling reactions.
The palladium catalyst which can be used for the palladium-catalyzed coupling reaction may be any one selected from ：Pd(P-tBu3)2、Pd(PPh3)4、Pd2(dba)3、Pd2(dba)3CHCl3、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd(OAc)2、Pd(acac)2、Pd/C、PdCl2、[Pd(allyl)Cl]2 and the like, or a mixture of two or more kinds may be used.
In addition, the base used for palladium-catalyzed or base-catalyzed coupling reactions may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amyl alcohol, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and mixtures of one or two or more thereof.
The coupling reaction may be carried out in an organic solvent, wherein the organic solvent may be selected from the group consisting of: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, and anisole, aromatic hydrocarbon solvents such as benzene, toluene, and xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and the like, and a mixture of one or more kinds of them may be used.
The invention also provides an organic electroluminescent material, which comprises the fluorene derivative; the organic electroluminescent material comprising the fluorene derivative of the present invention has a carrier transporting ability or a light extracting ability.
Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a light extraction layer material, or an electron blocking layer material.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a light extraction layer, and one or more organic layers interposed between the first electrode and the second electrode; at least one of the organic layer and the light extraction layer includes the fluorene derivative described above.
The organic electroluminescent element includes a first electrode, a second electrode, a light extraction layer, 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, electron-blocking layers, electron-transport layers, electron-injection layers, hole-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 element described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention 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 hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-transporting layer and the light-emitting layer and in the light-extracting layer, all materials can be used in the manner generally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process, wherein the material is applied by vapor deposition in a vacuum sublimation apparatus at an initial pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa.
Also preferred are organic electroluminescent elements, to which one or more layers can also be applied by means of an organic vapor deposition method or by means of sublimation of a carrier gas, wherein the material is applied at a pressure of between 10 -5 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 the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of preparations of the compounds of the invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl 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-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, 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.
The present invention also provides a use of an organic electroluminescent element for any one device selected from the following:
A flat panel display device;
a flexible display device;
a single color or white panel lighting device; or (b)
A single color or white flexible lighting device.
The beneficial effects obtained by the invention are as follows:
the fluorene derivative provided by the invention has a structure shown in a formula (I), and a mother nucleus group can effectively regulate and control the three-dimensional structure of molecules, so that the stacking density of the molecules is improved; meanwhile, the triarylamine structure and the fluorene structure act together, so that the compound has excellent hole transmission performance, the HOMO energy level of the compound is regulated and improved, the HOMO energy level of the compound is more matched with the energy level of an anode, the hole injection and transmission capacity of the compound is improved, the acquisition of low voltage is facilitated, and the stability of carrier transmission in an electric field environment is obviously improved. In addition, the special tetrahedral conjugated structure of the organic compound enables the organic compound to prepare a good amorphous film, so that the organic compound can be applied to an organic electroluminescent element to remarkably reduce the driving voltage, improve the luminous efficiency and prolong the service life.
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 layer 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 layer 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 layer 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of the device 100.
Detailed Description
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.
Any range recited in the present invention includes any numerical value between the end values and any sub-range formed by any numerical value between the end values or any numerical value between the end values unless specifically stated otherwise.
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 spectral scanner PhotoResearch PR-715;
Current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: the NEWPORT 1931-C test was used.
Example 1
A process for the preparation of compound D31 comprising the steps of:
The first step: preparation of intermediate Int-1
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22.0Mmol of SM-1 (CAS: 2667606-44-0), 20.0mmol of 5-chloro-2-bromo-benzoate, 60.0mmol of hydrated potassium phosphate, 0.1mmol of Pd0132, 80mL of 1, 4-dioxane and 25mL of water are mixed under the protection of nitrogen, the mixture is heated to reflux and stirred for reaction for 12 hours, cooled to room temperature, 100mL of saturated ammonium chloride aqueous solution is added, the mixture is extracted with ethyl acetate, an organic phase is collected, dried, concentrated under reduced pressure and separated and purified by a silica gel column to obtain a compound Int-1, white solid, yield: 75%.
And a second step of: preparation of Compound Int-2
Under the protection of nitrogen, 20.0mmol of intermediate Int-1 is dissolved in 60mL of dry THF, the temperature is reduced to 0 ℃, 60.0mmol of 1M methyl magnesium bromide THF solution is added dropwise, the temperature is raised to room temperature, stirring is carried out for 1 hour, 20mL of 3N diluted hydrochloric acid aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is collected, dried and concentrated under reduced pressure, and the compound Int-2 is obtained through separation and purification of a silica gel column, white solid is obtained, and the yield is: 83%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, 20.0mmol of intermediate Int-2 is dissolved in 60mL of dry dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride diethyl ether solution is added dropwise, the temperature is raised to room temperature, stirring is carried out for 12 hours, 20mL of water is added, an organic phase is separated, the water phase is extracted by dichloromethane, the organic phase is collected and washed by 5% sodium hydroxide aqueous solution, the water is washed, the organic phase is dried, reduced pressure concentration is carried out, and the compound Int-3 is obtained through separation and purification of a silica gel column, white solid is obtained in yield: 87%.
Fourth step: preparation of Compound D31
Under the protection of nitrogen, 22.0mmol of intermediate Int-3 is dissolved in 60mL of dry toluene, 20.0mmol of diarylamine, 30.0mmol of sodium tert-butoxide, 0.2mmol of Pd 2(dba)3 and 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution are added, the temperature is raised to 110 ℃ and stirred for reaction for 12 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by toluene, the organic phase is combined and dried, the filtration and the concentration of filtrate under reduced pressure are carried out, and the compound D31 is obtained by separating and purifying by a silica gel column;
t=o, white solid, yield ：80％,MS(MALDI-TOF)：m/z＝728.2889[M+H]+;1HNMR(δ、CDCl3)：8.83(1H,s);8.44～8.36(5H,m);8.11～8.09(1H,d);7.98～7.90(5H,m);7.79～7.72(5H,m);7.65～7.63(1H,m);7.61～7.52(4H,m);7.50～7.45(2H,m);7.40～7.33(6H,m);6.91～6.88(1H,m);1.79(6H,s).
T=cme 2, white solid, yield ：76％,MS(MALDI-TOF)：m/z＝754.3414[M+H]+;1HNMR(δ、CDCl3)：8.83(1H,s);8.44～8.36(5H,m);8.19～8.17(1H,d);8.11～8.06(4H,m);7.91～7.85(2H,m);7.78(1H,s);7.74～7.72(2H,m);7.61～7.59(1H,m);7.56～7.52(4H,m);7.50～7.45(2H,m);7.40～7.32(5H,m);7.30～7.26(2H,m);7.15～7.13(1H,d);1.73(6H,s);1.68(6H,s).
T=nph, white solid, yield ：72％,MS(MALDI-TOF)：m/z＝803.3394[M+H]+;1HNMR(δ、CDCl3)：8.83(1H,s);8.53(1H,s);8.42～8.36(5H,m);8.23～8.20(2H,d);8.11～8.06(4H,m);7.93～7.90(1H,m);7.79(1H,s);7.74～7.72(2H,m);7.63～7.57(4H,m);7.55～7.51(3H,m);7.48～7.43(4H,m);7.40～7.32(5H,m);7.24～7.21(2H,m);7.15～7.12(1H,m);1.74(6H,s).
T=fr (9, 9-fluorenyl), white solid, yield ：72％,MS(MALDI-TOF)：m/z＝876.3616[M+H]+;1HNMR(δ、CDCl3)：8.83(1H,s);8.42～8.36(5H,m);8.19～8.17(1H,d);8.11～8.06(4H,m);7.92～7.86(4H,m);7.78(1H,s);7.74～7.71(2H,m);7.62～7.58(1H,m);7.55～7.50(4H,m);7.48～7.43(4H,m);7.40～7.32(6H,m);7.29～7.21(5H,m);7.15～7.12(1H,m);1.74(6H,s).
Referring to the above-described similar synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
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Example 2
A process for the preparation of compound D89 comprising the steps of:
the first step: preparation of intermediate Int-4
Referring to the synthetic procedure of example 1, substituting only methyl 5-chloro-2-bromobenzoate in the first step of example 1 with 4-chloro-2-bromoiodobenzene, the compound Int-4 was prepared as a white solid in yield: 76%.
And a second step of: preparation of Compound Int-5
Under the protection of nitrogen, 20.0mmol of intermediate Int-4 is dissolved in 60mL of dry THF, the temperature is reduced to minus 78 ℃ by liquid nitrogen, 22.0mmol of 2.5M N-butyllithium N-hexane solution is added dropwise, stirring reaction is carried out for 30 minutes, 22.0mmol of fluorenone solution dissolved in THF is added dropwise, stirring reaction is carried out to a temperature of 2 hours, 20mL of 3N diluted hydrochloric acid aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtration and concentration of filtrate under reduced pressure are carried out, yellow solid is obtained and dissolved by 50mL of dichloromethane, the temperature is reduced to 0 ℃, 30.0mmol of boron trifluoride diethyl ether solution is added dropwise, stirring reaction is carried out to room temperature for 12 hours, 20mL of 25% sodium hydroxide aqueous solution is added, the organic phase is separated, drying and concentrating drying is carried out under reduced pressure, and separation and purification are carried out by a silica gel column, thus obtaining the compound Int-5, white solid, the yield: 74%.
And a third step of: preparation of Compound D89
Under the protection of nitrogen, 22.0mmol of intermediate Int-5 is dissolved in 80mL of dry toluene, 20.0mmol of bi-phenyl amine, 30.0mmol of tertiary sodium butoxide, 0.2mmol of Pd 2(dba)3 and 0.4mmol of 10% tri-tertiary butyl phosphorus toluene solution are added, the temperature is raised to 110 ℃ and stirred for reaction for 12 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by toluene, the organic phase is combined and dried, the filtrate is filtered, the filtrate is concentrated under reduced pressure to dryness, and the compound D89 is separated and purified by a silica gel column to obtain a white solid with the yield ：84％,MS(MALDI-TOF)：m/z＝836.3257[M+H]+;1HNMR(δ、CDCl3)：8.89(1H,s);8.42～8.36(4H,m);8.18～8.16(1H,d);8.11～8.06(4H,m);7.92～7.89(2H,m);7.78(1H,s);7.74～7.70(4H,m);7.64～7.62(1H,m);7.55～7.50(5H,m);7.48～7.42(5H,m);7.40～7.32(6H,m);7.29～7.21(5H,m);7.18～7.15(2H,m).
Referring to the above-described similar synthetic method, the following compounds shown in table 2 were prepared:
TABLE 2
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Example 3
A process for the preparation of compound D126 comprising the steps of:
the first step: preparation of Compound Int-6
Under the protection of nitrogen, 20.0mmol of SM-2 is dissolved in 80mL of dimethylbenzene, 50.0mmol of bis (p-bromophenyl) iodotriflate, 2.0mmol of palladium acetate and 20.0mmol of sodium tert-butoxide are added, the temperature is raised to 110 ℃, the reaction is carried out for 24 hours under stirring, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the aqueous phase is extracted by toluene, the organic phases are combined and dried, the filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-6 is obtained after separation and purification by a silica gel column, and the yield is yellow solid: 83%.
And a second step of: preparation of Compound Int-7
Under the protection of nitrogen, 24.4mmol of iodine is dissolved in 200mL of glacial acetic acid, 24.4mmol of 50% hypophosphorous acid is added dropwise, the temperature is raised to 100 ℃, the stirring reaction is carried out until red color disappears, 20.0mmol of Int-6 is added, the temperature is raised to reflux reaction for 6 hours, when about 50mL of ice water is remained after reduced pressure concentration, 200mL of ice water is added, filtration is carried out, a filter cake is washed with water and ethanol, and a yellow solid is obtained and is separated and purified by a silica gel column, so that a compound Int-7 is obtained, the white solid is obtained, and the yield is: 90%.
And a third step of: preparation of Compound Int-8
Under the protection of nitrogen, 20.0mmol of Int-7 is dissolved in 200mL of THF, 118.0mmol of potassium tert-butoxide is added, 79.0mmol of methyl iodide is added dropwise, stirring reaction is carried out at room temperature for 12 hours, 150mL of ice water is added, an organic phase is separated, the aqueous phase is extracted by methylene dichloride, the organic phases are combined and dried, filtration and reduced pressure concentration of filtrate are carried out, and separation and purification are carried out by a silica gel column to obtain a compound Int-8, white solid is obtained, and the yield: 85.5%.
Fourth step: preparation of Compound D126
Under the protection of nitrogen, 22.0mmol of intermediate Int-8 is dissolved in 120mL of dry toluene, 20.0mmol of biphenyl naphthylamine, 30.0mmol of sodium tert-butoxide, 0.2mmol of Pd 2(dba)3 and 0.4mmol of Xantphos are added, the temperature is raised to 110 ℃ and stirred for reaction for 12 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the water phase is extracted by toluene, the organic phase is combined and dried, the filtration and the filtrate concentration under reduced pressure are carried out, and the compound D126 is obtained by separation and purification by a silica gel column, white solid is obtained, the yield ：86％,MS(MALDI-TOF)：m/z＝688.3012[M+H]+;1HNMR(δ、CDCl3)：8.71(1H,s);8.55～8.48(3H,m);8.29～8.27(1H,d);8.13～8.06(2H,m);7.89～7.86(1H,m);7.72～7.62(5H,m);7.60～7.45(4H,m);7.41～7.36(2H,m);7.25～7.21(2H,m);7.18～7.07(7H,m);7.04(1H,s);7.01～6.98(2H,m);1.82(6H,s).
Referring to the above-described similar synthetic method, the following compounds shown in table 3 were prepared:
TABLE 3 Table 3
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Example 4
A process for the preparation of compound D166 comprising the steps of:
the first step: preparation of Compound Int-9
Under the protection of nitrogen, 20.0mmol of Int-6 is dissolved in 60mL of dry THF, the temperature is reduced to 0 ℃, 22.0mmol of phenylmagnesium bromide THF solution is added dropwise, the temperature is raised to room temperature, stirring is carried out for 2 hours, 20mL of 2N diluted hydrochloric acid aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtration and concentration of filtrate under reduced pressure are carried out, and compound Int-9 is obtained by separating and purifying by a silica gel column, yellow solid is obtained, and the yield is: 88%.
And a second step of: preparation of Compound Int-10
Under the protection of nitrogen, 20.0mmol of Int-9 is dissolved in 80mL of benzene, 40.0mmol of concentrated sulfuric acid is added dropwise, the temperature is raised to reflux for reaction for 12 hours, the temperature is reduced to room temperature, 50mL of ice water is added dropwise, an organic phase is separated, the aqueous phase is extracted by benzene, the organic phase is dried, filtered, and filtrate is concentrated under reduced pressure, and a green solid is obtained and is separated and purified by a silica gel column, so that a compound Int-10 is obtained as a white solid, and the yield is: 82%.
And a third step of: preparation of Compound D166
Referring to the synthesis of example 3, fourth step, compound D166 was prepared as a white solid in yield by substituting only Int-8 in example 3 for Int-10 and biphenylnaphthylamine for biphenylamine ：85％.MS(MALDI-TOF)：m/z＝838.3478[M+H]+;1HNMR(δ、CDCl3)：8.55～8.51(2H,m);8.29～8.22(2H,m);8.11(1H,s);7.64～7.59(3H,m);7.55～7.45(7H,m);7.40～7.32(6H,m);7.25～7.21(2H,m);7.15～7.07(8H,m);7.05～6.98(7H,m);6.95(1H,s);6.93～6.84(4H,m).
Referring to the above-described similar synthetic method, the following compounds shown in table 4 were prepared:
TABLE 4 Table 4
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In the above embodiments, T is selected from one of the following structures:
Example 5
An organic electroluminescent device 100, the structure of which is shown in fig. 1, comprises 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, and the element preparation method omitting the hole blocking layer 107 comprises the steps of:
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 a vacuum chamber, vacuumizing to less than 1× -5 Pa, evaporating metallic silver as anode layer on the ITO film, and evaporating film thickness to beVapor deposition compounds HI01 and HI102 were used as hole injection layers, wherein HI102 was 3% by mass of HI01, and the vapor deposition film thickness was/>
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) Vapor deposition of BH012 as a host material and BD022 as a dopant material were continued on the electron blocking layer, BD022 was 3% by mass of BH012, and the vapor deposition film thickness was set to be the organic light-emitting layer
6) Continuously evaporating a layer of LiQ and ET015 on the organic light-emitting layer as an electron transport layer, wherein the mass ratio of the LiQ to the ET015 is 50:50, and the thickness of the evaporated film 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, wherein the mass ratio of magnesium to silver is 1:10, and the film thickness of the evaporated film is
9) Evaporating a CPL layer with HTM as element on the transparent cathode layer to obtain an evaporated film thickness ofThe OLED element provided by the invention is obtained.
The structures of the compounds HI01, HI102, HTM, BH012, BD022, ET015 and LiQ used in example 5 are as follows:
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Example 6
An organic electroluminescent device 200, the structure of which is shown in fig. 2, comprises a substrate 201, an anode layer 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 layer 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.
Comparative example 1
By following the same procedure as in example 5, the compound represented by the formula (I) in step 4) was replaced with B-1 to obtain comparative element 1; the structural formula of B-1 is as follows:
Comparative example 2
By following the same procedure as in example 4, the compound represented by the formula (I) in step 4) was replaced with B-2 to obtain comparative element 2; the structural formula of the B-2 is as follows:
Comparative example 3
By following the same procedure as in example 4, the compound represented by the formula (I) in step 4) was replaced with B-3 to obtain comparative element 3; the structural formula of B-3 is as follows:
The performance test data of the obtained element were normalized with respect to comparative element 1, and the results are shown in Table 5, in which the driving voltage and luminous efficiency were obtained at a current density of 10mA/cm 2 for the element, and the LT95% lifetime of the element was measured at a starting condition at a current density of 50mA/cm 2.
TABLE 5 results of testing the performance of the elements
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In the table, me is methyl; ph is phenyl; phPh is biphenyl; nap is naphthyl; FR is 9, 9-fluorenyl.
As shown in Table 5, the luminescent device prepared by using the fluorene derivative as the electron blocking material of the present invention has a significantly reduced driving voltage compared with B-1, B-2 and B-3 under the condition of 10mA/cm 2, and has a significantly improved luminescence efficiency and LT95% lifetime performance, wherein the luminescence efficiency is as high as 1.4 times that of the comparative device, especially the LT95% lifetime is as high as 3 times that of the comparative device, which indicates that the compound of the present invention has an improved stability as the parent nucleus and is an electron blocking layer material with excellent performance.
Compared with the compound B-1 of the comparative example, the fluorene derivative is characterized in that the molecular plane of the B-1 is too large, the steric hindrance is large, the fluorene derivative is a tetrahedral conjugated plane, the steric hindrance is small, the fluorene derivative has excellent performance in molecular film formation and charge transmission, and the charge transmission in the element is more balanced, so that the element performance is improved, and the compound of the invention has more excellent performance in a light-emitting element.
Compared with the compounds B-2 and B-3 of the comparative example, the fluorene derivative is different in that both B-2 and B-3 are conjugated planar molecules, have no triarylamine group, have deeper HOMO energy level, cause unbalanced exciton transmission and larger carrier injection barrier in the element, and the unbalance leads to the increase of the driving voltage of the element and the reduction of the efficiency. The fluorene derivative has a triarylamine group, the carrier transmission performance is enhanced, the carrier injection barrier is reduced, the performance of the fluorene derivative in molecular film formation and charge transmission is excellent, exciton transmission in the element is more balanced, and therefore, the element performance is improved, and the compound of the invention is more excellent in the performance of a light-emitting element.
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 (5)

1. Fluorene derivative, characterized in that it is selected from the group consisting of the following D01 to D201:
Wherein-t— is selected from-O-, S-, or one of the following structures:
* -and- (x) represents a bond.
2. An organic electroluminescent material, characterized in that its raw material comprises the fluorene derivative as claimed in claim 1.
3. An organic electroluminescent element, characterized in that it comprises: a first electrode, a second electrode, a light extraction layer, and one or more organic layers interposed between the first electrode and the second electrode; at least one of the organic layer and the light extraction layer includes the fluorene derivative according to claim 1.
4. The organic electroluminescent element according to claim 3, wherein the organic layer comprises at least one of: a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer.
5. The organic electroluminescent element according to claim 3 or 4, wherein the organic electroluminescent element is used in any one of the following devices:
A flat panel display device or a flexible display device.
CN202211211985.3A 2022-09-30 2022-09-30 Fluorene derivative and organic light-emitting element comprising same Active CN115536535B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210048643A (en) * 2019-10-23 2021-05-04 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN112794842A (en) * 2019-11-14 2021-05-14 广州华睿光电材料有限公司 Polycyclic compound and use thereof
CN112794856A (en) * 2019-11-14 2021-05-14 广州华睿光电材料有限公司 Organic compounds, mixtures, compositions and uses thereof
CN115073501A (en) * 2021-03-10 2022-09-20 北京夏禾科技有限公司 Organic electroluminescent material and device thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210048643A (en) * 2019-10-23 2021-05-04 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN112794842A (en) * 2019-11-14 2021-05-14 广州华睿光电材料有限公司 Polycyclic compound and use thereof
CN112794856A (en) * 2019-11-14 2021-05-14 广州华睿光电材料有限公司 Organic compounds, mixtures, compositions and uses thereof
CN115073501A (en) * 2021-03-10 2022-09-20 北京夏禾科技有限公司 Organic electroluminescent material and device thereof

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