CN112321598B - Carbazole derivative and application thereof - Google Patents

Carbazole derivative and application thereof Download PDF

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CN112321598B
CN112321598B CN202011205068.5A CN202011205068A CN112321598B CN 112321598 B CN112321598 B CN 112321598B CN 202011205068 A CN202011205068 A CN 202011205068A CN 112321598 B CN112321598 B CN 112321598B
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organic electroluminescent
electroluminescent element
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carbazole derivative
compound
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CN112321598A (en
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曹建华
戴雄
唐怡杰
孙建波
边坤
王美艳
赵佳
王庆一
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to a carbazole derivative and its application, the structural formula of said carbazole derivative is shown as formula (I), said carbazole derivative has higher triplet state energy level, suitable for using as the material for organic electroluminescent element, the material for organic electroluminescent element comprising said carbazole derivative of the invention has low starting voltage, luminous efficiency and luminance are high, in addition, said carbazole derivative of the invention has good heat stability and film-forming property, apply to material, organic electroluminescent element, display device, lighting device for organic electroluminescent element, can lengthen the service life, thus can reduce the manufacturing cost of material, organic electroluminescent element, display device, lighting device for organic electroluminescent element.
Figure DDA0002756771450000011

Description

Carbazole derivative and application thereof
Technical Field
The invention belongs to the technical field of materials for organic electroluminescent elements, and particularly relates to a carbazole derivative and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the process of industrialization, many problems need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport properties, electroluminescent properties of materials, service life, color purity, matching among various materials and matching among various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1. It is urgent to use 75% of the energy of the triplet excitons. Forrest et al discovered in 1997 that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a carbazole derivative and use thereof, which is used as a raw material of a material for an organic electroluminescent element and can provide a material for an organic electroluminescent element and an organic electroluminescent element having a reduced starting voltage, improved luminous efficiency, and improved luminance.
The first object of the present invention is to provide a carbazole derivative, wherein the carbazole derivative has a structural formula shown in formula (I):
Figure GDA0002854977820000021
wherein R is 1 ～R 6 Identical or different from hydrogen, deuterium, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Or alkenyl or alkynyl, or one of an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R 1 ～R 6 Each group may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
x is selected from O or S;
w is the same or different at each occurrence and is selected from CR or N, and any two adjacent groups W represent a group of formula (1) or (2):
Figure GDA0002854977820000022
wherein G is C (R) 2 NR, oxygen or sulfur; z is the same or different at each occurrence, Z is CR or N, and "^" represents an adjacent group W;
r is the same or different at each occurrence and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 1 ) 2 、N(R 7 ) 2 、C(＝O)Ar 1 、C(＝O)R 7 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Or alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 80, preferably from 5 to 60, carbon atoms, or an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being able to be substitutedOne or more radicals R 7 By substitution, or combinations of these systems, in which one or more non-adjacent-CH is/are not adjacent 2 The radicals may be substituted by R 7 C＝CR 7 、C≡C、Si(R 7 ) 2 、Ge(R 7 ) 2 、Sn(R 7 ) 2 、C＝O、C＝S、C＝Se、C＝NR 7 、P(＝O)(R 7 )、SO、SO 2 、NR 7 O, S or CONR 7 And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R 7 Substitution;
R 7 identical or different at each occurrence and selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, N (Ar) 1 ) 2 、N(R 8 ) 2 、C(＝O)Ar 1 、C(＝O)R 8 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, R 7 Each radical in (A) may be substituted by one or more radicals R 8 By substitution, or combinations of these systems, in which one or more non-adjacent-CH is/are not adjacent 2 The radical may be represented by R 8 C＝CR 8 、C≡C、Si(R 8 ) 2 、Ge(R 8 ) 2 、Sn(R 8 ) 2 、C＝O、C＝S、C＝Se、C＝NR 8 、P(＝O)(R 8 )、SO、SO 2 、NR 8 O, S or CONR 8 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R may optionally be joined or fused to form a single ringOr polycyclic, aliphatic, aromatic or heteroaromatic ring systems which may be interrupted by one or more radicals R 8 Substitution;
Ar 1 identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R 8 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 3 Can also be selected from N (R) or through a single bond 8 )、C(R 8 ) 2 Oxygen or sulfur bridging groups;
R 8 selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C 1 ～C 20 An aliphatic hydrocarbon radical, an aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, R 8 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 8 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or S atoms. Thus, for example, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamines, diaryl ethers, etc., as well as systems in which two or more aryl groups are linked by, for example, short alkyl groups, are also to be understood as meaning aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains from 6 to 60 carbon atoms and heteroaryl in the sense of the present invention contains from 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which a single hydrogen atom or-CH 2 The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals whose radicals may also be substituted by the abovementioned radicals are preferably to be understood as meaning 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. Alkoxy, preferably alkoxy having 1 to 40 carbon atoms, is to be understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. 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, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where 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 aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R 8 Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure GDA0002854977820000051
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isoindole, spirotriindene, spiroisotridenzene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6,6 ] indole]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyrazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diaza pyrene, 2, 3-diaza pyrene, 1, 6-diaza pyrene, 1, 8-diaza pyrene, 4, 5-diaza pyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluor-red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.
Further, said R 1 ～R 6 Identical or different, selected from hydrogen, deuterium, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, R 1 ～R 6 Each group may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
x is selected from O or S;
w is the same or different at each occurrence and is selected from CR or N, and any two adjacent groups W represent a group of formula (1) or (2):
x is selected from O or S;
w is the same or different at each occurrence and is selected from CR or N, and any two adjacent groups W represent a group of formula (1) or (2):
Figure GDA0002854977820000061
wherein G is C (R) 2 NR, oxygen or sulfur; z is the same or different at each occurrence, Z is CR or N, and "^" represents an adjacent group W;
r is the same or different at each occurrence and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 1 ) 2 、N(R 7 ) 2 、C(＝O)Ar 1 、C(＝O)R 7 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Alkenyl or alkynyl groups of (a), aromatic rings having 5 to 80, preferably 5 to 60, carbon atoms orA heteroaromatic ring system, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 7 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 7 C＝CR 7 、C≡C、Si(R 7 ) 2 、Ge(R 7 ) 2 、Sn(R 7 ) 2 、C＝O、C＝S、C＝Se、C＝NR 7 、P(＝O)(R 7 )、SO、SO 2 、NR 7 O, S or CONR 7 And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R 7 Substitution;
R 7 identical or different at each occurrence and selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, nitrile groups, nitro groups, N (Ar) 1 ) 2 、N(R 8 ) 2 、C(＝O)Ar 1 、C(＝O)R 8 、P(＝O)(Ar 1 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, R 7 Each radical in (a) may be substituted by one or more radicals R 8 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 8 C＝CR 8 、C≡C、Si(R 8 ) 2 、Ge(R 8 ) 2 、Sn(R 8 ) 2 、C＝O、C＝S、C＝Se、C＝NR 8 、P(＝O)(R 8 )、SO、SO 2 、NR 8 O, S or CONR 8 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atomsA nitrile group or a nitro group, wherein two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 8 Substitution;
Ar 1 identical or different at each occurrence, from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be interrupted by one or more nonaromatic radicals R 8 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 3 Can also be selected from N (R) or through a single bond 8 )、C(R 8 ) 2 Oxygen or sulfur bridging groups;
R 8 selected from hydrogen atoms, deuterium atoms, fluorine atoms, nitrile groups, having C 1 ～C 20 An aliphatic hydrocarbon radical, an aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, R 8 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 8 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Further, the carbazole derivative has a specific structure as one of CJHK 486-CJHK 716:
Figure GDA0002854977820000081
Figure GDA0002854977820000091
Figure GDA0002854977820000101
Figure GDA0002854977820000111
Figure GDA0002854977820000121
Figure GDA0002854977820000131
Figure GDA0002854977820000141
Figure GDA0002854977820000151
Figure GDA0002854977820000161
Figure GDA0002854977820000171
Figure GDA0002854977820000181
Figure GDA0002854977820000191
Figure GDA0002854977820000201
Figure GDA0002854977820000211
wherein, X is selected from O or S independently.
The second object of the present invention is to provide a use of the carbazole derivative in a material for an organic element.
The material for organic devices of the present invention contains the compound of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The material for organic devices is a material for organic electroluminescent devices, a material for organic field effect transistors, or a material for organic thin film solar cells.
The compound of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
Further, the material for an organic electroluminescent element is a material for a light-emitting layer.
Furthermore, the material for the organic electroluminescent element is an electron transport layer material, a hole transport layer material or an encapsulation layer material.
A third object of the present invention is to provide an organic electroluminescent element comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, the at least one organic layer comprising the carbazole derivative.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-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 device 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, according to the invention, a compound 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 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-injecting and hole-transporting layer and in the electron-injecting and electron-transporting layer, all materials can be used in the manner conventionally used according to the prior art. A 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.
Preference is furthermore given to organic electroluminescent elements which are characterized in that one or more layers are 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 which are characterized in that one or more layers are applied by means of an organic vapor deposition method or by means of sublimation using a carrier gas, where 10 is -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 obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, 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 for producing an organic electroluminescent element according to the invention, characterized in that at least one layer is applied by means of a sublimation method and/or in that at least one layer is applied by means of an organic vapour deposition method or by means of carrier gas sublimation and/or in that at least one layer is applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a carbazole derivative comprising at least one of the above-indicated carbazole derivatives of the present invention. The same preferences as indicated above for the organic electroluminescent element apply to the carbazole derivative of the present invention. In particular, the carbazole derivative may preferably contain other compounds in addition. Processing the carbazole derivative according to the invention from the liquid phase, for example by spin coating or by printing methods, requires a formulation of the compound according to the invention. These formulations may be, for example, 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-xylene 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, α -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, tripropyl glycol, 1, 2-dimethyl benzyl glycol, 1, 2-octylbenzene, 2-dimethyl benzene ether, 2, 1, octylbenzene, or mixtures of these solvents.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
In a fourth aspect of the invention, there is provided a display device comprising the organic electroluminescent element.
In a fifth aspect of the present invention, there is provided a lighting device comprising the organic electroluminescent element.
Compared with the prior art, the invention has the beneficial effects that:
the carbazole derivative of the present invention has a high triplet level, is suitable for use as a material for an organic electroluminescent element, has a low activation voltage, and has high luminous efficiency and luminance.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of an example of top emission of the organic electroluminescent device of the present invention.
Reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transmission/electron blocking layer, 5-luminescent layer, 6-hole blocking/electron transmission layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without making any creative effort, shall fall within the protection scope of the present invention.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
The preparation method of the compound CJHK684 comprises the following steps:
first step, preparation of Compound Int-1
Figure GDA0002854977820000251
0.10mol of 1-dibenzofuran boronic acid or 1-dibenzothiophene boronic acid was dispersed in 150mL of toluene under nitrogen protection, and 0.1mol of 1, 8-dibromonaphthalene, 0.20mol of anhydrous sodium carbonate, and 0.5g of Pd (PPh) 3 ) 4 Adding 150mL of ethanol and 100mL of water into the catalyst, heating, refluxing, stirring and reacting for 8 hours, cooling to room temperature, adding 100mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a white solid with the yield of 83%.
The second step is that: preparation of Compound Int-2
Figure GDA0002854977820000252
25.0mmol of the intermediate Int-1 prepared in the first step, 7.5mmol of tricyclohexylphosphonium tetrafluoroborate, 5.0mmol of palladium acetate, 50.0mmol of anhydrous cesium carbonate and 80mL of dimethylacetamide, under the protection of nitrogen, heating, refluxing, stirring, reacting for 12 hours, cooling to room temperature, adding 200mL of water for dilution, extracting with ethyl acetate, collecting the organic phase, washing with saturated saline, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying with a silica gel column to obtain the compound Int-2 with the yield of 58%.
The third step: preparation of Compound Int-3
Figure GDA0002854977820000261
20.0mmol of the intermediate Int-2 prepared in the second step is dissolved in 100mL of dry tetrahydrofuran, the temperature is reduced to-80 ℃ by liquid nitrogen under the protection of nitrogen, 10.0mL of 2.5M butyl lithium n-hexane solution is added dropwise, stirring reaction is carried out for 1 hour, 30.0mmol of trimethyl borate solution in anhydrous tetrahydrofuran is added dropwise, stirring reaction is carried out for 1 hour, the temperature is raised to-10 ℃, 50mL of 2M dilute hydrochloric acid aqueous solution is added, stirring reaction is carried out for 30 minutes, ethyl acetate is used for extraction, an organic phase is collected, drying and filtering are carried out, filtrate is concentrated under reduced pressure and dried, petroleum ether is added for dispersion, and filtering is carried out, thus obtaining the compound Int-3 with the yield of 65%.
The fourth step: preparation of Compound Int-4
Figure GDA0002854977820000262
Under nitrogen protection, 20.0mmol of intermediate Int-3 was dispersed in 60mL of toluene, and 17.0mmol of o-nitrobromobenzene, 40.0mmol of anhydrous sodium carbonate, and 0.2g of Pd (PPh) were added 3 ) 4 Adding 30mL of ethanol and 30mL of water into the catalyst, heating, refluxing, stirring, reacting for 8 hours, cooling to room temperature, adding 100mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a yellow solid with the yield of 74%.
The fifth step: preparation of Compound Int-5
Figure GDA0002854977820000271
20.0mmol of the intermediate Int-4 prepared in the fourth step and 60.0mL of triethyl phosphite are mixed, heated, refluxed, stirred and reacted for 16 hours, cooled to room temperature, concentrated under reduced pressure to dryness, and separated and purified by a silica gel column to obtain the compound Int-5 as a yellow solid with the yield of 85%.
And a sixth step: preparation of compound CJHK684
Figure GDA0002854977820000272
10.0mmol of intermediate Int-5 prepared in the fifth step is dissolved in 50mL of dry dimethyl sulfoxide, cooled to 5 ℃ in an ice water bath under the protection of nitrogen, 12.0mmol of 65% sodium hydride is added in portions, stirred for reaction for 1 hour, then 12.0mmol of 2- ([ 1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine is added, the temperature is raised to room temperature, stirred for reaction for 12 hours, 200mL of water is added for dilution, filtering is carried out, a filter cake is washed by water and ethanol, and then separation and purification is carried out by a silica gel column, thus obtaining compound HK684, a yellow solid, and the yield is 60-70%.
Experimental data:
CJHK684-1(X＝O)：
MS(MALDI-TOF):m/z 689.2357[M+H]+；1HNMR(δ、CDCl3)：9.06～9.04(1H,m)；8.53～8.46(3H,m)；8.27～8.09(9H,m)；7.95～7.87(3H,m)；7.70～7.67(2H,m)；7.49～7.38(6H,m)；7.34～7.26(4H,m)。
CJHK684-2(X＝S)：
MS(MALDI-TOF):m/z 705.2131[M+H]+；1HNMR(δ、CDCl3)：8.97～8.95(1H,m)；8.52～8.45(4H,m)；8.37(1H,s)；8.25～8.07(10H,m)；7.70～7.67(2H,m)；7.49～7.46(2H,m)；7.42～7.36(4H,m)；7.34～7.36(4H,m)。
example 2
Preparation of the compounds CJHK663 to CJHK683 and CJHK685 to CJHK716, referring to the preparation method of example 1, various halides were replaced with the sixth step 2- ([ 1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine of example 1, and other experimental parameters were routinely adjusted.
Example 3
The preparation method of the compound CJHK644 comprises the following steps:
the first step is as follows: preparation of Compound Int-6
Figure GDA0002854977820000281
20.0mmol of the intermediate Int-2 prepared in the second step of example 1 was dissolved in 60mL of dry THF, cooled to 0 ℃ in an ice water bath under the protection of nitrogen, 22.0mmol of a 2.5M n-butyllithium n-hexane solution was added dropwise, stirred for reaction for 1 hour, warmed to room temperature and stirred for reaction for 5 hours, then 24.0mmol of a solution of iodine in THF was added dropwise, stirred for reaction for 2 hours, 20mL of a saturated aqueous solution of sodium bisulfite was added dropwise, extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and then separated and purified by a silica gel column to obtain the compound Int-6 as a white solid with a yield of 62%.
The second step is that: preparation of Compound Int-7
Figure GDA0002854977820000282
10.0mmol of the intermediate Int-6 prepared in the first step is dissolved in 80mL of N, N-dimethylformamide, 12.0mmol of o-chloroaniline, 10.0mmol of copper powder and 25.0mmol of anhydrous potassium carbonate are added under the protection of nitrogen, the mixture is heated to 100 ℃ and stirred for reaction for 8 hours, the mixture is cooled to room temperature and filtered, the filtrate is poured into 200mL of ice water and filtered, the filter cake is washed with water and ethanol, and the solid is separated and purified by a silica gel column to obtain the compound Int-7 as a yellow solid with the yield of 84%.
The third step: preparation of Compound Int-8
Figure GDA0002854977820000291
10.0mmol of the intermediate Int-7 prepared in the second step is dissolved in 80mL of toluene, under the protection of nitrogen, 15.0mmol of anhydrous cesium carbonate, 1.0mmol of cuprous iodide, 1.0mmol of palladium acetate and 2.0mmol of SPhos are added, the temperature is raised to 100 ℃, the mixture is stirred and reacted for 12 hours, the mixture is cooled to room temperature, 100mL of water is added for dilution, ethyl acetate is used for extraction, an organic phase is collected, dried and filtered, filtrate is concentrated under reduced pressure to be dry, and the dry filtrate is separated and purified by a silica gel column to obtain the compound Int-8 which is yellow solid with the yield of 88%.
The fourth step: preparation of Compound CJHK644
Figure GDA0002854977820000292
10.0mmol of the intermediate Int-8 prepared in the previous step is dissolved in 50mL of dry dimethyl sulfoxide, the temperature is reduced to 5 ℃ by using an ice water bath under the protection of nitrogen, 12.0mmol of 65% sodium hydride is added in batches, the mixture is stirred and reacted for 1 hour, 12.0mmol of 2-chloro-3-phenylquinoxaline is added, the temperature is increased to 60 ℃, the mixture is stirred and reacted for 12 hours, 200mL of water is added for dilution, the filtration is carried out, a filter cake is washed by water and ethanol, and then the mixture is separated and purified by using a silica gel column, so that a compound CJHK644 is obtained, a yellow solid is obtained, and the yield is 70-80%.
Experimental data:
CJHK644-1(X＝O)：
MS(MALDI-TOF):m/z 586.1937[M+H]+；1HNMR(δ、CDCl3)：8.72(1H,s)；8.52～8.49(1H,m)；8.29～8.23(4H,m)；8.04～7.89(8H,m)；7.81～7.77(3H,m)；7.56～7.46(4H,m)；7.28～7.24(1H,m)；7.16～7.13(1H,m)。
CJHK644-2(X＝S)：
MS(MALDI-TOF):m/z 602.1707[M+H]+；1HNMR(δ、CDCl3)：8.79(1H,s)；8.43～8.40(2H,m)；8.27～8.17(6H,m)；8.06～7.89(5H,m)；7.81～7.79(2H,m)；7.56～7.52(2H,m)；7.44～7.36(3H,m)；7.24～7.20(1H,m)；7.16～7.13(1H,m)。
example 4
The compounds CJHK612 to CJHK643 and CJHK645 to CJHK662 were prepared according to the preparation method of example 3 except that different halides were substituted for the 2-chloro-3-phenylquinoxaline of the fourth step in example 3 and other parameters were adaptively adjusted.
Example 5
The preparation method of the compound CJHK549 comprises the following steps:
the first step is as follows: preparation of Compound Int-9
Figure GDA0002854977820000301
Under the protection of nitrogen, 15.0mmol of 1-chloro-8-iodo-dibenzo [ b, d ]]Furan or 1-chloro-8-iodo-dibenzo [ b, d ]]Thiophene was dispersed in 60mL of toluene, and 16.0mmol of pinacol o-nitrobenzoate, 30.0mmol of anhydrous sodium carbonate, and 0.15g of Pd (PPh) 3 ) 4 Adding 30mL of ethanol and 30mL of water into the catalyst, heating, refluxing, stirring, reacting for 8 hours, cooling to room temperature, adding 100mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering,filtering, decompressing, concentrating and drying, separating and purifying by a silica gel column to obtain yellow solid with the yield of 82 percent.
The second step is that: preparation of Compound Int-10
Figure GDA0002854977820000302
Under the protection of nitrogen, 10.0mmol of intermediate Int-9 is dissolved in 60mL of N, N-dimethylformamide, 12.0mmol of pinacol diboride, 15.0mmol of anhydrous cesium carbonate, 45.0mg of palladium acetate catalyst and 0.2g of bis (diphenylphosphino) ferrocene are added, the temperature is raised to 90 ℃, the reaction is stirred for 8 hours, the mixture is cooled to room temperature, 100mL of water is added for dilution, ethyl acetate is used for extraction, the organic phase is collected, dried, filtered, decompressed, concentrated and dried, and separated and purified by a silica gel column to obtain yellow solid with the yield of 88%.
The third step: preparation of Compound Int-11
Figure GDA0002854977820000311
Under nitrogen protection, 10.0mmol of intermediate Int-10 was dissolved in 60mL of toluene, and 10.0mmol of 1, 8-dibromonaphthalene, 20.0mmol of anhydrous sodium carbonate, and 45.0mg of Pd (PPh) were added 3 ) 4 Heating a palladium catalyst, refluxing and stirring for reaction for 10 hours, cooling to room temperature, adding 100mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a yellow solid with the yield of 76%.
The fourth step: preparation of Compound Int-12
Figure GDA0002854977820000312
Under the protection of nitrogen, 10.0mmol of intermediate Int-11 is dissolved in 100mL of chlorobenzene, 30.0mmol of triphenyl phosphine is added, the temperature is increased, reflux and stirring are carried out for reaction for 15 hours, the reaction product is cooled to room temperature, reduced pressure concentration is carried out, 100mL of dichloromethane is added, filtration is carried out, and a filter cake is washed by methanol to obtain yellow solid with the yield of 75-80%.
The fifth step: preparation of Compound Int-13
Figure GDA0002854977820000313
Dissolving 15.0mmol of intermediate Int-12 in 60mL of dry N, N-dimethylformamide, cooling to 0 ℃ in an ice water bath under the protection of nitrogen, adding 18.0mmol of 65% sodium hydride in batches, stirring for reaction for 1 hour, adding 18.0mmol of N, N-dimethylformamide solution of 5-phenyl-2-bromochlorobenzyl chloride dropwise, heating to room temperature, stirring for reaction for 12 hours, adding 200mL of water for dilution, filtering, washing a filter cake with water and ethanol to obtain a compound Int-13, namely a yellow solid, wherein the yield is 85-90%.
And a sixth step: preparation of Compound Int-14
Figure GDA0002854977820000321
20.0mmol of intermediate Int-13 is dissolved in 80mL of N, N-dimethylformamide, under the protection of nitrogen, 3.0mmol of palladium acetate, 10.0mmol of benzyltrimethylammonium bromide, 60.0mmol of anhydrous cesium carbonate and 1.0mmol of SPhos ligand are added, the temperature is raised to 90 ℃, the reaction is stirred for 48 hours, the mixture is cooled to room temperature, 200mL of water is added for dilution, the filtration is carried out, a filter cake is washed by water and ethanol, and the solid is separated and purified by a silica gel column, so that the compound Int-14 is obtained and is yellow solid with the yield of 65%.
The seventh step: preparation of compound CJHK549
Figure GDA0002854977820000322
Dissolving 15.0mmol of intermediate Int-14 in 150mL of chloroform, adding 30.0mmol of potassium permanganate and 1.0g of 18-crown-6, heating, refluxing, stirring and reacting for 48 hours, cooling to room temperature, filtering, washing a filter cake with dichloromethane, collecting a filtrate, separating and purifying a solid by using a silica gel column, and recrystallizing with toluene-THF to obtain a compound CJHK549 in yellow solid with the yield of 65-70%.
Experimental data:
CJHK549-1(X＝O)：
MS(MALDI-TOF):m/z 560.1667[M+H]+；1HNMR(δ、CDCl3)：8.90～8.88(1H,m)；8.77～8.73(3H,m)；8.38～8.32(4H,m)；8.18～8.10(4H,m)；7.88～7.85(2H,m)；7.65～7.61(1H,m)；7.54～7.49(3H,m)；7.46～7.44(2H,m)；7.39～7.37(1H,m)。
CJHK549-2(X＝S)：
MS(MALDI-TOF):m/z 576.1440[M+H]+；1HNMR(δ、CDCl3)：8.75～8.72(2H,m)；8.68(1H,s)；8.65～8.63(1H,m)；8.45～8.42(1H,m)；8.21～8.12(7H,m)；7.97～7.95(1H,d)；7.92～7.90(1H,d)；7.69～7.65(1H,m)；7.54～7.49(3H,m)；7.47～7.44(2H,m)；7.39～7.37(1H,m)。
example 6
The preparation of CJHK547-548 and CJHK550-557 compounds CJHK549 in example 5 were prepared in accordance with the following method except that 5-phenyl-2-bromochlorobenzyl chloride in the fifth step of example 5 was replaced with different benzyl chloride and other experimental parameters were adaptively adjusted.
Example 7
The preparation method of the compound CJHK579 comprises the following steps:
the first step is as follows: preparation of Compound Int-15
Figure GDA0002854977820000331
Dissolving 15.0mmol of benzofuran or benzothiophene in 120mL of dry THF, cooling to-78 ℃ with liquid nitrogen under the protection of nitrogen, dropwise adding 18.0mmol of 2.5M n-butyllithium n-hexane solution, stirring for reaction for 1 hour, dropwise adding 12.5mmol of indole-3-formaldehyde solution in THF, heating to room temperature, stirring for reaction for 1 hour, dropwise adding 20mL of saturated ammonium chloride aqueous solution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying with a silica gel column to obtain the compound Int-15 with the yield of 95%.
The second step: preparation of Compound Int-16
Figure GDA0002854977820000341
Dissolving 15.0mmol of intermediate Int-15 in 80mL of dichloromethane, adding 18.0mmol of triethylsilane under the protection of nitrogen, slowly dropwise adding a solution of 15.0mmol of trifluoroacetic acid in dichloromethane, stirring for reacting for 2 hours, adding 40mL of 10% sodium hydroxide aqueous solution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying through a silica gel column to obtain a compound Int-16 with the yield of 80-90%.
The third step: preparation of Compound Int-17
Figure GDA0002854977820000342
10.0mmol of intermediate Int-16 are dissolved in 100mL of ethanol and 5.0mmol of intermediate Int-16 are added
Figure GDA0002854977820000344
Acid, then 10.0mmol of 8-bromo-1-naphthaldehyde is added, stirring and reacting are carried out for 12 hours, filtering is carried out, and a filter cake is washed by ethanol to obtain white solid with the yield of 90-95%.
The fourth step: preparation of Compound Int-18
Figure GDA0002854977820000343
20.0mmol of intermediate Int-17 was dispersed in 250mL of xylene, warmed to 100 deg.C, and added in portions with 0.20mol of manganese dioxide solids, warmed, refluxed, stirred, reacted for 24 hours, cooled to room temperature, filtered, the filtrate was concentrated to dryness under reduced pressure, and recrystallized with dichloromethane/ethanol to give a yellow solid with a yield of 85%.
The fifth step: preparation of Compound Int-19
Figure GDA0002854977820000351
Dissolving 10.0mmol of intermediate Int-18 in 50mL of dry N, N-dimethylformamide, cooling to 0 ℃ in an ice water bath under the protection of nitrogen, adding 12.0mmol of 65% sodium hydride in batches, stirring for reaction for 1 hour, adding 12.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, stirring for reaction for 12 hours, adding 100mL of water for dilution, filtering, washing a filter cake with water and ethanol, and obtaining a compound Int-19 as a yellow solid with the yield of 85-90%.
And a sixth step: preparation of compound CJHK579
Figure GDA0002854977820000352
Dissolving 10.0mmol of intermediate Int-19 in 60mL of xylene, adding 1.0mmol of cuprous iodide and 1.0mmol of palladium acetate under the protection of nitrogen, adding 15.0mmol of anhydrous cesium carbonate and 2.0mmol of SPhos ligand, heating to 110 ℃, stirring for reaction for 12 hours, cooling to room temperature, filtering, washing a filter cake with toluene, decompressing and concentrating a filtrate to dryness, and separating and purifying by using a silica gel column to obtain a compound CJHK579, a yellow solid with the yield of 76-85%.
Experimental data:
CJHK579-1(X＝O)：
MS(MALDI-TOF):m/z 613.2042[M+H]+；1HNMR(δ、CDCl3)：8.83～8.81(1H,m)；8.76～8.73(1H,m)；8.60(1H,s)；8.58～8.54(4H,m)；8.41～8.37(5H,m)；8.13～8.03(3H,m)；7.86～7.83(1H,m)；7.52～7.48(1H,m)；7.45～7.40(6H,m)；7.37～7.34(1H,m)。
CJHK579-2(X＝S)：
MS(MALDI-TOF):m/z 629.1818[M+H]+；1HNMR(δ、CDCl3)：8.92～8.89(1H,m)；8.73(1H,s)；8.59～8.54(5H,m)；8.44～8.24(7H,m)；8.16～8.12(2H,m)；7.53～7.49(1H,m)；7.44～7.40(6H,m)；7.36～7.32(1H,m)。
example 8
The compounds CJHK 558-CJHK 578 and CJHK 580-CJHK 611 refer to the preparation method of the compound CJHK579 in example 7 except that a different halide is substituted for the 2-chloro-4, 6-diphenyl-1, 3, 5-triazine of the fifth step in example 7 and other experimental parameters are adaptively adjusted.
Example 9
The preparation method of the compound CJHK497 comprises the following reaction steps:
the first step is as follows: preparation of intermediate Int-20
Figure GDA0002854977820000361
10.0mmol of the intermediate Int-12 prepared in the fourth step in example 5 was dissolved in 80mL of toluene, 15.0mmol of anhydrous potassium carbonate and 1.0mmol of cuprous iodide were added, 0.1mmol of palladium acetate and 0.2mmol of SPhos ligand were added, the mixture was heated to 100 ℃ and stirred for reaction for 12 hours, cooled to room temperature, filtered, the filter cake was washed with water, and the solid was separated and purified by a silica gel column to obtain intermediate Int-20 as a yellow solid with a yield of 75-80%.
The second step is that: preparation of compound CJHK497
Figure GDA0002854977820000362
Under the protection of nitrogen, 10.0mmol of intermediate Int-20 is dissolved in 60mL of toluene, 12.0mmol of 3-bromo-9-phenylcarbazole, 15.0mmol of sodium tert-butoxide and 0.1mmol of Pd2 (dba) 3 catalyst are added, 0.1mL of 10% tri-tert-butylphosphine toluene solution is added, the temperature is raised to 90 ℃, the mixture is stirred and reacted for 12 hours, the mixture is cooled to room temperature, 20mL of water is added, dichloromethane is used for extraction, an organic phase is collected, dried and filtered, and the filtrate is decompressed, concentrated and dried, and is separated and purified by a silica gel column to obtain a CJHK497 product, namely a pale yellow solid with the yield of 75-80%.
CJHK497-1(X＝O)：
MS(MALDI-TOF):m/z 623.2141[M+H]+；1HNMR(δ、CDCl3)：8.63～8.61(1H,m)；8.49～8.47(1H,m)；8.38～8.34(4H,m)；8.06～7.97(5H,m)；7.86～7.82(2H,m)；7.56～7.48(5H,m)；7.37～7.29(5H,m)；7.24～7.19(3H,m)。
CJHK497-2(X＝S)：
MS(MALDI-TOF):m/z 639.1912[M+H]+；1HNMR(δ、CDCl3)：8.55～8.53(2H,m)；8.43～8.42(1H,m)；8.35～8.26(5H,m)；8.17～8.12(4H,m)；8.07(1H,s)；7.54～7.47(5H,m)；7.38～7.28(5H,m)；7.23～7.18(3H,m)。
Example 10
The preparation of the compounds CJHK 486-CJHK 496 and CJHK 498-CJHK 546 was performed according to the preparation method of CJHK497 in example 9, except that different halides were substituted for 3-bromo-9-phenylcarbazole in the second step in example 9 and other experimental parameters were adaptively adjusted.
Preparation of organic electroluminescent element
Comparative example 1
An organic electroluminescent element was prepared as follows using a compound represented by the following formula a as a green host material, a compound represented by the following formula B as a green dopant material, a compound represented by the following formula C as a hole injection material, a compound represented by the following formula D as a hole transport material, a compound represented by the following formula E as a red host material, a compound represented by the following formula F as a red dopant material, a compound represented by the following formula G as an electron transport dopant material, and LiQ as an electron transport host material as comparative samples.
Figure GDA0002854977820000381
Will be of the chemical formula C
Figure GDA0002854977820000382
/D
Figure GDA0002854977820000383
/A+B(5％)
Figure GDA0002854977820000384
/LiQ+G(50％)
Figure GDA0002854977820000385
/LiF
Figure GDA0002854977820000386
Al (2 nm) was deposited on ITO glass by an EL deposition machine manufactured by DOV to prepare a green light element, and an organic electroluminescent element as a green light comparative example was prepared.
Will be the chemical formula C
Figure GDA0002854977820000387
/D
Figure GDA0002854977820000388
/E+F(5％)
Figure GDA0002854977820000389
/LiQ+G(50％)
Figure GDA00028549778200003810
/LiF
Figure GDA00028549778200003811
Al (2 nm) was deposited on ITO glass by an EL deposition machine manufactured by DOV to prepare a red light emitting element, and an organic electroluminescent element as a red light emitting comparative example was prepared.
Test example 1
An organic electroluminescent element was fabricated by the method of comparative example 1, substituting compound a with one of compounds CJHK486 to CJHK 716: ITO/C
Figure GDA0002854977820000391
/D
Figure GDA0002854977820000392
/[ inventive Compounds CJHK 486-CJHK 716]+B(5％)
Figure GDA0002854977820000393
/LiQ+G(50％)
Figure GDA0002854977820000394
/LiF
Figure GDA0002854977820000395
/Al(2nm)。
The results of measuring the properties of the obtained element are shown in Table 1, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm 2 Conditions were obtained and the voltage, LE, FWHM and LT90% were normalized to the reference.
Table 1: green light element performance detection result
Figure GDA0002854977820000396
As can be seen from the above, the green light device produced from the organic material of the present invention has a lower driving voltage, a higher current efficiency, and a good color purity than the device produced in comparative example 1, and the emission luminance of the device was initially 2000cd/cm 2 Under the initial conditions, the service life of the element using the compound of the invention as a green light host material is greatly improved.
The properties of only a portion of the compounds are listed in table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the table, and are not listed due to space limitation.
An organic electroluminescent element was fabricated in the same manner as in comparative example 1, except that the aforementioned compound E was replaced with the compounds CJHK486 to CJHK716 of the present invention: ITO/C
Figure GDA0002854977820000397
/D
Figure GDA0002854977820000398
/[ inventive Compounds CJHK 486-CJHK 716]+F(5％)
Figure GDA0002854977820000399
/LiQ+G(50％)
Figure GDA00028549778200003910
/LiF
Figure GDA00028549778200003911
/Al(2nm)。
The results of measuring the properties of the obtained element are shown in Table 2, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm 2 The conditions were obtained and the voltage, LE, FWHM and LT90% were normalized to the reference.
TABLE 2 detection results of red light element performance
Figure GDA0002854977820000401
As can be seen from the performance test results of the red light device in Table 2, the device prepared from the organic material of the present invention has significantly lower driving voltage, high current efficiency and good color purity of light emission compared to the red light device prepared in comparative example 1. At an initial luminance of 2000cd/cm 2 Under the initial conditions, the LT90% lifetime of the element using the compound of the present invention as a red host material is significantly improved.
Only some of the properties of the compounds are listed in table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the table, and are not listed any more due to space limitations.
As shown in fig. 1 and 2, which are a schematic view of a bottom emission example of the organic electroluminescent device of the present invention and a schematic view of a top emission example of the organic electroluminescent device, respectively, the carbazole derivative prepared in the present invention is contained in the light-emitting layer 5.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily think of the changes or substitutions within the technical scope of the present invention, and shall cover the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (8)

1. A carbazole derivative having a specific structure as one of CJHK 486-CJHK 716:
Figure FDA0003847345010000011
Figure FDA0003847345010000021
Figure FDA0003847345010000031
Figure FDA0003847345010000041
Figure FDA0003847345010000051
Figure FDA0003847345010000061
Figure FDA0003847345010000071
Figure FDA0003847345010000081
Figure FDA0003847345010000091
Figure FDA0003847345010000101
Figure FDA0003847345010000111
Figure FDA0003847345010000121
Figure FDA0003847345010000131
Figure FDA0003847345010000141
wherein, X is selected from O or S independently.
2. Use of the carbazole derivative as claimed in claim 1 in a material for an organic element.
3. The use according to claim 2, wherein the material for organic devices is a material for organic electroluminescent devices, a material for organic field effect transistors, or a material for organic thin film solar cells.
4. The use according to claim 3, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.
5. The use of claim 3, wherein the material for the organic electroluminescent element is an electron transport layer material, a hole transport layer material or an encapsulation layer material.
6. An organic electroluminescent element comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises the carbazole derivative as claimed in claim 1.
7. A display device comprising the organic electroluminescent element according to claim 6.
8. A lighting device comprising the organic electroluminescent element according to claim 6.
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