CN115677513A - Polysubstituted naphthalene derivative and application thereof - Google Patents

Polysubstituted naphthalene derivative and application thereof Download PDF

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CN115677513A
CN115677513A CN202211251465.5A CN202211251465A CN115677513A CN 115677513 A CN115677513 A CN 115677513A CN 202211251465 A CN202211251465 A CN 202211251465A CN 115677513 A CN115677513 A CN 115677513A
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substituted
unsubstituted
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naphthalene derivative
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曹建华
姜卫东
刘殿君
郭文龙
李程辉
王振宇
唐伟
刘赛赛
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a polysubstituted naphthalene derivative and an organic light-emitting element comprising the polysubstituted naphthalene derivative. The polysubstituted naphthalene derivative increases the plane conjugation capability, and improves the thermal stability of the material and the capability of transporting carriers; the polysubstituted naphthalene 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.
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Description

Polysubstituted naphthalene derivative and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a polysubstituted naphthalene derivative and application thereof in an organic electroluminescent element.
Background
In recent years, optoelectronic devices based on organic materials are becoming more popular, and compared with inorganic materials, the inherent flexibility of organic materials makes them suitable for manufacturing on flexible substrates, and various optoelectronic products can be designed and produced according to requirements. Currently known organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like; among them, OLEDs have advantages of self-luminescence, high contrast, wide color gamut, flexibility, low power consumption, etc., have been developed particularly rapidly, have been commercially successful, and are 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 thin film structure arranged between the two electrodes, the core of the OLED element is the thin film structure containing various organic functional materials, and the common organic functional materials comprise: 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 material (dopant material), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, to generate excitons and emit light. In an OLED element, organic functional materials directly affect the light emitting properties of the device.
The hole transport material is used as a universal layer material of the OLED element, and the core indexes of the element, such as voltage, efficiency, service life and the like, are influenced by adjusting the injection and transport performance of holes. At present, hole transport materials for commercial mass production are mainly arylamine materials, and due to different material collocation of devices, the problems of OLED product efficiency, service life, cost and the like cannot be completely solved by the currently used materials and element structures.
Accordingly, in order to overcome the above-described problems of the conventional techniques and further improve the characteristics of the organic electroluminescent element, development of a more stable and effective substance which can be used as a hole-forming material in the organic electroluminescent element is continuously required.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a polysubstituted naphthalene derivative, which has good photoelectric characteristics, and an organic electroluminescent element prepared by using the polysubstituted naphthalene derivative, in particular an element used as a hole transport material and/or an electron blocking material, can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life; the invention also aims to provide the application of the polysubstituted naphthalene derivative in an organic electroluminescent element.
Specifically, the invention provides the following technical scheme:
the invention provides a polysubstituted naphthalene derivative, which has a structural formula shown in a formula (I):
Figure BDA0003888381700000011
wherein:
R 1 、R 2 、R 3 、R 4 each independently selected from hydrogen, deuterium, C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; any adjacent two or more substituents may be optionally joined or fused to form a substituted or unsubstituted ring;
Ar 1 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Ar 2 selected from the group consisting of C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
n is an integer of 0 to 5;
L 1 selected from single bond, substituted or unsubstituted C 6 -C 60 Or substituted or unsubstituted C 2 -C 60 A heteroarylene group.
In the present invention, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring formed by bonding adjacent groups to each other.
Preferably, R is 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen, C 1 -C 40 Or any adjacent two fused to form a ring.
Preferably, ar is 1 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups.
Preferably, ar is 2 Selected from the group consisting of C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups.
Preferably, n is 0, 1 or 2.
Alkyl in the sense of the present invention contains 1 to 40 carbon atoms and where the individual hydrogen atoms or-CH 2 The aliphatic hydrocarbon radicals whose radicals may also be substituted by deuterium, fluorine or heteroatoms such as N, O, S are preferably taken to mean the following radicals: 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, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutyloxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylbutyloxyHexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy groups. Heteroalkyl is preferably alkyl having 1 to 40 carbon atoms, meaning that the individual hydrogen atoms or-CH 2 The radicals which may be substituted by oxygen, sulfur, halogen atoms, are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, 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, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH may be present 2 The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.
The "aryl" according to the invention refers to and includes monocyclic aromatic hydrocarbon radicals and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbyl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. Preferred aryl groups are those containing from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms. Especially preferred are aryl groups having six carbons, ten carbons, or twelve carbons. Suitable aryl groups include phenyl, biphenyl, and the like terphenyl, triphenylene, tetraphenylene,Naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene,
Figure BDA0003888381700000021
And azulenes, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted.
"heteroaryl" in the sense of the present invention means and includes monocyclic aromatic groups and polycyclic aromatic ring systems comprising at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases, oxygen, sulfur or nitrogen are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic with 5 or 6 ring atoms, and rings may have one to six heteroatoms. A heteropolycyclic system can have two or more rings in which two atoms are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles and/or heteroaryls. The heteropolyaromatic ring system may have from one to six heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothienopyridine, benzonaphthopyridine, selenophene bipyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzothiophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborane, 1, 4-azaalkyne, and their analogs. In addition, the heteroaryl group may be optionally substituted.
As used herein, "a combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
In one example, the term substituted includes combinations of two to four of the listed groups.
The fused aryl group used in the present invention is a monovalent functional group obtained by combining two or more aromatic hydrocarbons having 6 to 60 carbon atoms and removing one hydrogen atom. In this case, two or more rings may be attached to each other simply or in a condensed form. As non-limiting examples thereof, may be mentioned phenanthryl, anthracyl, fluoranthyl, pyrenyl, triphenylenyl, perylenyl, perylene, etc,
Figure BDA0003888381700000031
And the like.
The arylamine group used in the present invention means an amine substituted with an aryl group having 6 to 60 carbon atoms, and non-limiting examples of the arylamine group include a diphenylamino group, an N-phenyl-1-naphthylamino group, an N- (1-naphthyl) -2-naphthylamino group and the like. The heteroarylamine 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 non-limiting examples of the heteroarylamine group include an N-phenylpyridine-3-amine group, an N- ([ 1,1 '-biphenyl ] -4-yl) dibenzo [ b, d ] furan-2-amine group, an N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluorene-2-amine group, and the like.
Preferably, said aryl, heterocyclic aryl, in particular refers to groups derived from: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl,
Figure BDA0003888381700000032
A phenyl group, a peryleneyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a triphenylenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a cis-or trans-indenocarbazolyl group, a cis-or trans-indolocarbazolyl group, a triindenylgroup, an isotridecylindenyl group, a spiroisotridecylindenyl group, a furanyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo [5,6 ] group]Quinolyl, benzo [6,7 ]]Quinolyl, benzo [7,8 ]]Quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazenanthrenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorerynyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, carbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 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 radicals or derivatives thereofA combination of systems.
Further, said R 1 、R 2 、R 3 、R 4 Each is hydrogen.
Further, said Ar 1 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
Further, said Ar 2 Selected from the group consisting of tert-butyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
Preferably, said L is 1 Selected from a single bond or a group consisting of the following groups III-1 to III-23:
Figure BDA0003888381700000041
wherein the dotted line represents the attachment site of the group.
In the present invention, the term "substituted or unsubstituted" means a compound selected from the group consisting of hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, and C 1 -C 40 Alkyl of (C) 2 -C 40 Alkenyl of, C 2 -C 40 An alkynyl group of,C 1 -C 40 Alkoxy group of (C) 3 -C 40 Cycloalkyl of (C) 3 -C 40 Cycloalkenyl group of (A), C 6 -C 60 Aryl of (C) 6 -C 60 Aryloxy group of (1), C 6 -C 60 And C 2 -C 60 The heterocyclic aryl group of (1) is substituted or unsubstituted or substituted or unsubstituted with a substituent in which 2 or more substituents among the above-exemplified substituents are bonded.
Preferably, the structural formula of the polysubstituted naphthalene derivative is selected from the group consisting of D01 to D207 below:
Figure BDA0003888381700000042
Figure BDA0003888381700000051
Figure BDA0003888381700000061
Figure BDA0003888381700000071
Figure BDA0003888381700000081
Figure BDA0003888381700000091
Figure BDA0003888381700000101
Figure BDA0003888381700000111
Figure BDA0003888381700000121
Figure BDA0003888381700000131
Figure BDA0003888381700000141
Figure BDA0003888381700000151
wherein, x-T 1 —*、*—T 2 -O-, S-, or one of the following structures:
Figure BDA0003888381700000152
preferably, said x-T 1 —*、*—T 2 -is selected from-O, -S, -or one of the following structures:
Figure BDA0003888381700000153
further, said T-T 1 —*、*—T 2 -is selected from-O-, -S-, or one of the following structures:
Figure BDA0003888381700000154
the foregoing represents a bond.
The invention provides a synthetic route of a compound shown as a formula (I), which is shown as follows:
Figure BDA0003888381700000155
wherein X 1 、X 2 Represents I, br, cl, OTf, boronic acid or boronic acid pinacol ester; the other symbols used are as defined above.
The raw materials for synthesizing the compound shown in the formula (I) can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and other means are well known by the synthesizers in the field, and the synthesis process can be completely realized to obtain the target product.
Specifically, the compound of the formula (I) is prepared from substituted o-nitrile-group halogenated benzene through Glaser coupling reaction, addition ring reaction, diazotization reaction, SUZUKI coupling reaction, reduction reaction, substitution reaction, buchwald-Hartwig coupling reaction and the like. Intermediate Ar 3 Ar 4 N-(L 1 ) n B(OH) 2 Or Ar 3 Ar 4 The NH is prepared by a palladium-catalyzed or base-catalyzed coupling reaction.
As palladium catalysts which may be used in the palladium-catalyzed coupling reaction, there may be selected: pd (P- t Bu 3 ) 2 、Pd(PPh 3 ) 4 、Pd 2 (dba) 3 、Pd 2 (dba) 3 CHCl 3 、PdCl 2 (PPh 3 ) 2 、PdCl 2 (CH 3 CN) 2 、Pd(OAc) 2 、Pd(acac) 2 、Pd/C、PdCl 2 、[Pd(allyl)Cl] 2 And the like, or a mixture of two or more thereof is used.
In addition, the base used in the palladium-catalyzed coupling reaction or base-catalyzed coupling reaction may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, 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: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, or anisole, aromatic hydrocarbon solvents such as benzene, toluene, or xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and one or a mixture of two or more thereof may be used.
The invention also provides an organic electroluminescent material, the raw material of which comprises the fluorene derivative; the organic electroluminescent material comprising the fluorene derivative of the present invention has carrier transporting ability or 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 electroluminescence element including: a first electrode, a second electrode, a light extraction layer, and one or more organic layers disposed 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-injecting layers, hole-transporting layers, functional layers having both hole-transporting and electron-blocking functions, electron-transporting layers, electron-injecting layers, hole-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not 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 are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the compounds of the invention according to the invention.
Further, the organic electroluminescent element according to the 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 the anode and/or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and the light-emitting layer and in the capping layer, all materials can be used in the manner conventionally 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 light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10% -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10 is at -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermography, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
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 pharmaceutical compositions comprising at least one compound of the invention as indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. Processing of the compounds of the invention from the liquid phase, for example by spin coating or by printing processes, requires the processing of formulations of the compounds of the invention which may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchytone, 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, a-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 dibutyl glycol methyl ether, triethyl glycol, tripropyl glycol, 1, 2-dimethyl benzyl ether, 1, 2-octylbenzene glycol, 1, 2-dimethyl-octylbenzene ether, 1, octylbenzene glycol, or mixtures of these solvents.
The present invention also provides an application of an organic electroluminescent element used in any one device selected from the following devices:
a flat panel display device;
a flexible display device;
a monochromatic or white flat panel lighting device; or
A monochromatic or white flexible lighting device.
The invention has the following beneficial effects:
the polysubstituted naphthalene derivative provided by the invention has a structure that at least 1,2,3 positions of naphthalene are trisubstituted at the same time, and aryl or heteroaryl groups can effectively regulate the three-dimensional structure of molecules, so that the stacking density of the molecules is improved; meanwhile, the triarylamine structure and the 1, 3-disubstituted naphthalene structure have a resonance effect, so that the compound has excellent hole transport performance, the HOMO energy level of the compound is regulated, controlled and improved, the HOMO energy level of the compound is more matched with the energy level of an anode, the hole injection and transport capacity of the compound are improved, the low voltage acquisition is facilitated, and the stability of the compound for transporting carriers in an electric field environment is obviously improved. Moreover, the organic compound has a special conjugated structure, so that a good amorphous film can be prepared, and therefore, when the organic compound is applied to an organic electroluminescent element, the driving voltage can be remarkably reduced, the luminous efficiency can be improved, and the service life can be prolonged.
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, an emissive 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 described layers.
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 light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer 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 intended to illustrate the invention but are not intended to limit the scope of the invention.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience in describing the present invention and simplifying the description, but do not indicate or imply that the referred devices or elements must have a specific orientation, be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The experimental raw materials and the relevant equipment used in the following examples are commercially available unless otherwise specified, and the percentages are by mass unless otherwise specified.
In addition, unless otherwise specified, any range recited herein includes any value between the endpoints and any sub-range defined by any value between the endpoints or any value between the endpoints.
The following test instruments and methods for performance testing of OLED materials and devices were used in the examples as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing by using a spectrum scanner PhotoResearhPR-715;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1
A process for the preparation of compound D10 comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
Figure BDA0003888381700000181
Under the protection of nitrogen, 20.0mmol of SM-1 (prepared by the synthesis method of the example in patent CN 113429395A) is dissolved in 60mL of acetonitrile, the temperature is reduced to 0 ℃, 60.0mmol of p-toluenesulfonic acid is added in batches, the mixture is stirred and reacted for 30 minutes, an aqueous solution of 40.0mmol of sodium nitrite mixed with 50.0mmol of potassium iodide is slowly added dropwise, the mixture is heated to room temperature and stirred and reacted for 12 hours, 50mL of saturated sodium thiosulfate aqueous solution is added dropwise, the ethyl acetate is used for extraction, an organic phase is collected, dried, concentrated under reduced pressure and dried, and separated and purified by a silica gel column to obtain a compound Int-1, a yellow solid, and the yield: 66 percent.
The second step is that: preparation of Compound Int-2
Figure BDA0003888381700000182
20.0mmol of intermediate Int-1 was dissolved in 40mL of toluene under nitrogen, 22.0mmol of 2-naphthalene boronic acid, 60.0mmol of sodium bicarbonate and 0.01mmol of Pd (PPh) were added 3 ) 4 Adding 20mL of ethanol and 20mL of water, heating, refluxing, stirring, reacting for 5 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, and adding waterExtracting the phases with ethyl acetate, collecting the organic phase, drying, concentrating under reduced pressure, separating and purifying by a silica gel column to obtain a compound Int-2, a yellow solid, and the yield: 83 percent.
The third step: preparation of Compound Int-3
Figure BDA0003888381700000191
Under the protection of nitrogen, 20.0mmol of intermediate Int-2 is dissolved in 80mL of ethanol, 0.5g of 5% palladium/carbon is added, hydrogen is introduced at normal pressure, the mixture is stirred and reacted for 12 hours at room temperature, the mixture is filtered, and the filtrate is concentrated under reduced pressure to be dry to obtain a compound Int-3, namely a yellow solid, the yield is as follows: 100 percent.
The fourth step: preparation of Compound D10
Figure BDA0003888381700000192
Under the protection of nitrogen, 20.0mmol of intermediate Int-3 is dissolved in 80mL of dry toluene, and 50.0mmol of 4-bromobiphenyl, 60.0mmol of sodium tert-butoxide and 0.1mmol of Pd are added 2 (dba) 3 And 0.2mmol of 10% tri-tert-butylphosphonium toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, extracting a water phase with toluene, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound D10, a white solid, and the yield: 78%, MS (MALDI-TOF): m/z =706.3488[ m + H ]] + ； 1 HNMR(δ、CDCl 3 )：8.61(1H，s)；8.19(1H，s)；8.08～7.91(5H，m)；7.78～7.75(2H，m)；7.70～7.64(3H，m)；7.62～7.55(5H，m)；7.53～7.45(6H，m)；7.40～7.35(2H，m)；7.21～7.16(5H，m)；7.07～7.03(4H，m)；1.29(9H，s)。
Example 2
A process for the preparation of compound D113, comprising the steps of:
the first step is as follows: preparation of intermediate Int-4
Figure BDA0003888381700000193
Referring to the synthesis method of example 1, only substituting 2-naphthoic acid in the second step of example 1 with 9, 9-dimethylfluorene-2-boronic acid or 9,9' -spirobifluorene-2-boronic acid or dibenzofuran-3-boronic acid or dibenzothiophene-3-boronic acid or 9-substituted carbazole-2-boronic acid or 5, 5-dimethylsilafluorene-3-boronic acid was prepared to obtain compound Int-4, a yellow solid, yield: 75 to 85 percent.
The second step is that: preparation of Compound Int-5
Figure BDA0003888381700000194
Referring to the synthesis method of the third step in example 1, only Int-2 in the third step in example 1 is replaced with Int-4 to prepare amino intermediate Int-5 with a yield of 96% -100%.
The third step: preparation of Compound Int-6
Figure BDA0003888381700000195
Under the protection of nitrogen, 22.0mmol of intermediate Int-5 is dissolved in 80mL of dry toluene, and 20.0mmol of 2-bromo-9, 9-dimethylfluorene or 2-bromo-9, 9' -spirobifluorene or 3-bromo-dibenzofuran or 3-bromo-dibenzothiophene or 2-bromo-9-substituted carbazole or 3-bromo-5, 5-dimethylsilylfluorene, 30.0mmol of sodium tert-butoxide, 0.1mmol of Pd 2 (dba) 3 And 0.2mmol of Xantphos, heating to 90 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 20mL of water, separating an organic phase, extracting the aqueous phase with dichloromethane, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-6, a white solid, and the yield: 84 percent.
The fourth step: preparation of Compound D113
Figure BDA0003888381700000201
20.0mmol of intermediate Int-6 are dissolved in 60mL of dry toluene under nitrogen, 22.0mmol of 4-bromobiphenyl, 30.0mmol of sodium tert-butoxide, 0.1mmol of Pd2 (dba) are added 3 Heating to 100 ℃ with 0.2mmol of 10% tri-tert-butylphosphine toluene solution, stirring for reaction for 12 hours, cooling to room temperature, adding 20mL of water, separating an organic phase, extracting a water phase with dichloromethane, combining the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound D113;
T 1 、T 2 ：CMe 2 white solid, yield: 86%, MS (MALDI-TOF): m/z =756.3644[ M + H ]] + ； 1 HNMR(δ、CDCl 3 )：8.56(1H，s)；8.26～8.24(2H，d)；8.06～8.04(1H，d)；7.95～7.86(5H，m)；7.78～7.75(3H，m)；7.72～7.64(3H，m)；7.62～7.59(2H，m)；7.53～7.45(4H，m)；7.39～7.33(2H，m)；7.31～7.28(2H，m)；7.25～7.16(5H，m)；7.03(1H，s)；7.08～7.05(2H，m)；1.72(6H，s)；1.68(6H，s)。
T 1 ：NPh、T 2 ：CMe 2 White solid, yield: 86%, MS (MALDI-TOF): m/z =805.3588[ m + H ]] + ； 1 HNMR(δ、CDCl 3 )：8.65(1H，s)；8.27(1H，s)；8.17～8.12(3H，m)；7.88～7.83(3H，m)；7.78～7.75(2H，m)；7.69～7.64(2H，m)；7.61～7.54(4H，m)；7.52～7.45(6H，m)；7.40～7.26(7H，m)；7.24～7.16(5H，m)；7.12～7.09(2H，m)；7.06～7.02(2H，m)；1.68(6H，s)。
Referring to a similar synthetic method to the above examples 1 and 2, the following compounds shown in table 1 were prepared:
TABLE 1
Figure BDA0003888381700000202
Figure BDA0003888381700000211
Figure BDA0003888381700000221
Figure BDA0003888381700000231
Figure BDA0003888381700000241
Figure BDA0003888381700000251
Figure BDA0003888381700000261
Figure BDA0003888381700000271
Figure BDA0003888381700000281
Figure BDA0003888381700000291
Figure BDA0003888381700000301
Figure BDA0003888381700000311
Figure BDA0003888381700000321
Figure BDA0003888381700000331
Figure BDA0003888381700000341
Figure BDA0003888381700000351
In the above examples 1 and 2, — T 1 —*、*—T 2 Each independently selected from-O-, -S-, or one of the following structures:
Figure BDA0003888381700000352
example 3
An organic electroluminescent element 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 preparation method of the element without the hole blocking layer 107 comprises the following steps:
1) And (3) carrying out ultrasonic treatment on the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, washing in deionized water, carrying out ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baking in a clean environment until the glass substrate is completely dried, irradiating for 10 minutes by using an ultraviolet cleaning machine, and bombarding the surface by using low-energy cation beams.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to less than 1 × 10 -5 Pa, depositing silver on the ITO film as anode layer to obtain a deposited film with a thickness of
Figure BDA0003888381700000353
Depositing HI01 and HI102 as hole injection layer, wherein HI102 is 3% of HI01 mass, and the thickness of the deposited film is
Figure BDA0003888381700000354
3) Continuously depositing a compound represented by the formula (I) of the present invention on the hole injection layer as a hole transport layer to a thickness of
Figure BDA0003888381700000355
4) Continuously depositing a compound EBM on the hole transport layer to form an electron blocking layer, wherein the thickness of the deposited layer is
Figure BDA0003888381700000356
5) RH022 as a host material and RD028 as a dopant material were continuously vapor-deposited on the electron blocking layer, RD028 was 3% by mass of RH022, and the organic light-emitting layer was formed by vapor-deposition to a film thickness of 3% by mass
Figure BDA0003888381700000357
6) And continuously evaporating a layer of LiQ and ET015 on the organic light-emitting layer to form an electron transport layer, wherein the mass ratio of LiQ to ET015 is 50:50, the thickness of the deposition film is
Figure BDA0003888381700000358
7) Continuously evaporating a layer of LiF on the electron transport layer to form an electron injection layer, wherein the thickness of the evaporated film is
Figure BDA0003888381700000359
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 thickness of the evaporated film is
Figure BDA00038883817000003510
9) Evaporating a layer of the same compound as the step 3) as an element on the transparent cathode layerA capping layer of the member having a thickness of
Figure BDA00038883817000003511
The OLED element provided by the invention is obtained.
The structures of the compounds HI01, HI102, EBM, RH022, RD028, ET015 and LiQ used in example 3 are as follows:
Figure BDA0003888381700000361
example 4
An organic electroluminescent device 200, as 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, a charge generation layer 206, a second light-emitting layer 207, an electron transport layer 208, an electron injection layer 209, a cathode 210 and a capping layer 211. The device 200 can be prepared by sequentially depositing the described layers by the method of example 3. Since the most common OLED devices have one light emitting layer, while the device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer 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
Following the same procedure as in example 3, the compound represented by formula (I) in step 3) was replaced with H-1 to give comparative element 1; the structural formula of H-1 is as follows:
Figure BDA0003888381700000362
comparative example 2
Following the same procedure as in example 3, the compound represented by formula (I) in step 3) was replaced with H-2 to give comparative element 2; the structural formula of H-2 is as follows:
Figure BDA0003888381700000363
comparative example 3
Following the same procedure as in example 3, the compound represented by formula (I) in step 3) was replaced with H-3 to give comparative element 3; the structural formula of H-3 is as follows:
Figure BDA0003888381700000364
the performance test data of the obtained element was normalized with reference to comparative element 1, and the results are shown in Table 2, in which the driving voltage and the luminous efficiency were measured at a current density of 10mA/cm 2 Under the conditions, the LT95% lifetime of the element was determined at a current density of 50mA/cm 2 Measured under the starting conditions of (a).
TABLE 2 test results of the performance of each element
Figure BDA0003888381700000371
Figure BDA0003888381700000381
Figure BDA0003888381700000391
Figure BDA0003888381700000401
Figure BDA0003888381700000411
In the table, me is methyl; ph is phenyl; FR is 9,9-fluorenyl.
As can be seen from Table 2, the light-emitting device produced using the polysubstituted naphthalene derivative of the invention as a hole transport layer material was also at 10mA/cm 2 Under the condition, the driving voltage is obviously reduced compared with H-1, H-2 and H-3, the luminous efficiency and LT95% service life performance are greatly improved, the luminous efficiency can reach as much as 1.2 times of that of a comparison element, and especially the LT95% service life is greatly improved, which shows that the polysubstituted naphthalene derivative is a hole transport layer material with excellent performance.
Compared with the compound H-1 of the comparative example, the polysubstituted naphthalene derivative is different in that H-1 has no substituent at the 3-position of naphthalene, the conjugated plane of the naphthalene is weak, while the polysubstituted naphthalene derivative simultaneously introduces substituents at the 1,2 and 3-positions of the naphthalene, particularly introduces triarylamine groups at the 2-position, the carrier transmission is enhanced, the charge transmission inside the element is more balanced, and therefore, the element performance is improved, and the polysubstituted naphthalene derivative is more excellent in performance of a light-emitting element.
Compared with the compounds H-2 and H-3 of the comparative examples, the polysubstituted naphthalene derivative of the invention is different in that H-2 and H-3 are weak plane conjugated molecules, which causes the imbalance of exciton transmission in the element and larger carrier injection potential barrier, and the imbalance causes the increase of the driving voltage of the element and the reduction of the efficiency. Due to the special conjugated structure, the polysubstituted naphthalene derivative has enhanced carrier transmission performance, reduces carrier injection potential barrier, has excellent performance on molecular film formation and charge transmission, and ensures that exciton transmission in the element is more balanced, so that the element performance is improved, and the compound has more excellent performance on a light-emitting element.
Although the invention has been described in detail with respect to the general description and the specific embodiments thereof, it will be apparent to those skilled in the art that modifications and improvements can be made based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. A polysubstituted naphthalene derivative is characterized in that the structural formula is shown as the formula (I):
Figure FDA0003888381690000011
wherein:
R 1 、R 2 、R 3 、R 4 each independently selected from hydrogen, deuterium, C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; any adjacent two or more substituents may be optionally joined or fused to form a substituted or unsubstituted ring;
Ar 1 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Ar 2 selected from the group consisting of C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
n is an integer of 0 to 5;
L 1 selected from single bond, substituted or unsubstituted C 6 -C 60 Or substituted or unsubstituted C 2 -C 60 A heteroarylene group.
2. The polysubstituted naphthalene derivative according to claim 1, wherein said R is selected from the group consisting of 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen, C 1 -C 40 Or an alkyl group ofMeaning that two adjacent fused rings form a ring;
Ar 1 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Ar 2 is selected from the group consisting of C 1 -C 40 Alkyl of (C) 3 -C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
n is 0, 1 or 2.
3. The polysubstituted naphthalene derivative according to claim 1, wherein said R is selected from the group consisting of 1 、R 2 、R 3 、R 4 Each is hydrogen;
Ar 1 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
Ar 2 selected from the group consisting of a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl 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 dibenzothiophenyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group.
4. The polysubstituted naphthalene derivative of any one of claims 1 to 3, wherein said L 1 Selected from a single bond or a group consisting of the following groups III-1 to III-23:
Figure FDA0003888381690000021
Figure FDA0003888381690000031
wherein the dotted line represents the attachment site of the group.
5. The polysubstituted naphthalene derivative according to any one of the claims 1 to 4, wherein the structural formula of said polysubstituted naphthalene derivative is selected from the group consisting of D01 to D207:
Figure FDA0003888381690000032
Figure FDA0003888381690000041
Figure FDA0003888381690000051
Figure FDA0003888381690000061
Figure FDA0003888381690000071
Figure FDA0003888381690000081
Figure FDA0003888381690000091
Figure FDA0003888381690000101
Figure FDA0003888381690000111
Figure FDA0003888381690000121
Figure FDA0003888381690000131
wherein, -T 1 -*、*-T 2 Each is independently selected from-O-, -S-, or one of the following structures:
Figure FDA0003888381690000132
preferably, said x-T 1 -*、*-T 2 Is selected from-O-, -S-or one of the following structures:
Figure FDA0003888381690000141
* -and-represent a connecting bond.
6. The polysubstituted naphthalene derivative according to claim 5, wherein said T-T 1 -*、*-T 2 Is selected from-O-, -S-or one of the following structures:
Figure FDA0003888381690000142
* -and-represent a connecting bond.
7. An organic electroluminescent material, characterized in that its raw material comprises the polysubstituted naphthalene derivatives according to any one of claims 1 to 6.
8. An organic electroluminescent element, characterized by comprising: the organic light-emitting diode comprises a first electrode, a second electrode, a capping layer and more than one organic layer arranged between the first electrode and the second electrode; at least one of the organic layer and the capping layer comprises a polysubstituted naphthalene derivative according to any one of claims 1 to 6.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises at least one of the following layers: 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; the selected one or more layers among the respective layers are formed through a deposition process or a solution process.
10. The organic electroluminescent element according to claim 8 or 9, wherein the organic electroluminescent element is used in any one device selected from the group consisting of:
a flat panel display device;
a flexible display device;
a monochromatic or white flat panel lighting device; or
A monochromatic or white flexible lighting device.
CN202211251465.5A 2022-10-13 2022-10-13 Polysubstituted naphthalene derivative and application thereof Pending CN115677513A (en)

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US20190140177A1 (en) * 2017-11-08 2019-05-09 Sfc Co., Ltd. Amine-substituted naphthalene derivatives and organic light emitting diodes including the same
CN111039799A (en) * 2018-10-12 2020-04-21 三星显示有限公司 Organic electroluminescent device and amine compound for organic electroluminescent device
CN113745415A (en) * 2020-05-27 2021-12-03 三星显示有限公司 Organic electroluminescent device and amine compound for organic electroluminescent device
CN116023354A (en) * 2021-10-25 2023-04-28 三星显示有限公司 Light-emitting element and amine compound for light-emitting element

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190140177A1 (en) * 2017-11-08 2019-05-09 Sfc Co., Ltd. Amine-substituted naphthalene derivatives and organic light emitting diodes including the same
CN111039799A (en) * 2018-10-12 2020-04-21 三星显示有限公司 Organic electroluminescent device and amine compound for organic electroluminescent device
CN113745415A (en) * 2020-05-27 2021-12-03 三星显示有限公司 Organic electroluminescent device and amine compound for organic electroluminescent device
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