CN109593042B - Organic electroluminescent material and organic electroluminescent device comprising same - Google Patents

Organic electroluminescent material and organic electroluminescent device comprising same Download PDF

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CN109593042B
CN109593042B CN201811581701.3A CN201811581701A CN109593042B CN 109593042 B CN109593042 B CN 109593042B CN 201811581701 A CN201811581701 A CN 201811581701A CN 109593042 B CN109593042 B CN 109593042B
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CN109593042A (en
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马天天
杨雷
李红燕
冯震
孙占义
王亚龙
李健
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The invention provides an organic electroluminescent material and an organic electroluminescent device comprising the same, and belongs to the technical field of electroluminescence. According to the invention, on the basis of a bis (triarylamine) symmetrical structure, adamantane is introduced as a new core group, the molecular form is changed, and the structural symmetry is reduced, so that the film-forming property of the material is improved; the adamantyl group has larger steric hindrance and a rigid structure, and the non-conjugated molecular structure of the adamantyl group does not influence the electronic energy level of triarylamine, so that the hole transport performance of the material is ensured; the compound containing the adamantyl group has excellent hole transport performance, can be used for manufacturing organic electroluminescent devices, particularly used as a hole transport layer material in the organic electroluminescent devices, and can effectively improve the luminous efficiency and prolong the service life of the organic electroluminescent devices.

Description

Organic electroluminescent material and organic electroluminescent device comprising same
Technical Field
The invention relates to an organic electroluminescent material and application thereof as a hole transport layer material in an organic electroluminescent device, in particular to the organic electroluminescent material and the organic electroluminescent device comprising the organic electroluminescent material, belonging to the field of electroluminescence.
Background
Electroluminescence (EL) is a physical phenomenon in which an electric field is generated by a voltage applied to two electrodes, electrons excited by the electric field collide with a luminescence center, and the electrons undergo transition, change, and recombination between energy levels to emit light. In recent years, Organic electroluminescent devices (OLEDs) have been gradually introduced into the human field of vision as a new generation of display technology. An OLED is an electroluminescent device formed of a multi-layered organic thin film structure in which an organic thin film is a film of an organic light emitting material formed on a substrate using an evaporation, or spin coating process. Compared with the traditional display technology, the display technology has the advantages of voltage characteristic, light-emitting brightness, light-emitting efficiency, color quality, response speed, viewing angle and the like, and has low cost, thereby having wide market prospect.
In order to improve the luminance, efficiency and lifetime of organic electroluminescent devices, a multilayer structure is generally used in the devices. These multilayer structures include: the organic layers have the functions of improving the injection efficiency of carriers (holes and electrons) between the interfaces of each layer, balancing the capability of the carriers to be transmitted between each layer, and thus improving the brightness and the efficiency of the device.
At present, although a large number of organic electroluminescent materials with excellent performance have been developed, the technology still has many problems, and how to design new materials with better performance to adjust, so that all devices can achieve the effects of reducing voltage, improving efficiency and prolonging life, is a problem to be solved by those skilled in the art.
Disclosure of Invention
The purpose of the present invention is to provide an organic electroluminescent material which has high heat resistance and excellent chemical stability and can be used as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or the like.
Another object of the present invention is to provide an organic light emitting device including the organic electroluminescent material, which has a lower driving voltage, higher light emitting efficiency and a longer service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic electroluminescent material, the structural formula of which is shown in chemical formula 1:
Figure BDA0001918079770000021
Ar1、Ar2、Ar5and Ar6The same or different, each is selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted alkynyl with 2-24 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 carbon atoms, substituted or unsubstitutedOne of a heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
Ar3and Ar4The same or different, each is independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 24 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaralkylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 15 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 15 carbon atoms, One of substituted or unsubstituted heteroalkynylene groups having 2 to 15 carbon atoms;
ar is1、Ar2、Ar3、Ar4、Ar5And Ar6The substituents (B) are the same or different and each is independently selected from deuterium, a cyano group, a nitro group, a halogen, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having a halogen atom, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having a halogen atom, A substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 20 carbon atoms,One of a substituted or unsubstituted aralkylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 24 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 20 carbon atoms.
In a further development of the invention, Ar is1、Ar2、Ar5And Ar6The same or different, each independently selected from a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms.
In a further development of the invention, Ar is3、Ar4One member selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 30 carbon atoms, and a substituted or unsubstituted heteroaralkylene group having 2 to 30 carbon atoms.
In a further improvement of the present invention, the chemical formula 1 is one of the following structures:
Figure BDA0001918079770000031
Figure BDA0001918079770000041
Figure BDA0001918079770000051
Figure BDA0001918079770000061
Figure BDA0001918079770000071
Figure BDA0001918079770000081
in a further development of the invention, Ar is3、Ar4And (b) one selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
An organic electroluminescent device comprising a cathode, an anode and one or more organic layers between the cathode and the anode, at least one of the one or more organic layers between the cathode and the anode comprising an electroluminescent material as hereinbefore described.
In a further development of the invention, the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.
In a further development of the invention, the organic layer comprising the electroluminescent material as claimed in claim 1 is a hole transport layer.
Compared with the prior art, the invention has the following beneficial effects:
1. according to the invention, on the basis of a bis (triarylamine) symmetrical structure, adamantane is introduced as a new core group, the molecular form is changed, and the structural symmetry is reduced, so that the film-forming property of the material is improved;
2. the adamantyl group has larger steric hindrance and a rigid structure, and the non-conjugated molecular structure of the adamantyl group does not influence the electronic energy level of triarylamine, so that the hole transport performance of the material is ensured;
3. the adamantane group at the central position of the molecule can also be protected by triarylamine at two sides, and can inhibit the isomerization/dehydrogenation reaction at high temperature to a certain extent, so that the purity of the material and the performance of a device are improved;
4. the compound containing the adamantyl group has excellent hole transport performance, can be used for manufacturing organic electroluminescent devices, particularly used as a hole transport layer material in the organic electroluminescent devices, and can effectively improve the luminous efficiency and prolong the service life of the organic electroluminescent devices.
Drawings
FIG. 1 is a schematic structural diagram of an organic electroluminescent material according to the present invention.
Detailed Description
The present invention will be described in further detail below with reference to examples. However, the following examples are merely illustrative of the present invention and are not intended to limit the present invention.
Referring to fig. 1, an organic electroluminescent material according to the present invention has a structural formula shown in chemical formula 1:
Figure BDA0001918079770000091
Ar1、Ar2、Ar5and Ar6The same or different, each is independently selected from one of substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted heteroaralkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
Ar3and Ar4The same or different, each is independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 24 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having a carbon atom number ofIs one of a heterocycloalkylene group of 2 to 20, a substituted or unsubstituted aralkylene group of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaralkylene group of 2 to 30 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group of 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkenylene group of 3 to 15 carbon atoms, a substituted or unsubstituted heteroalkenylene group of 2 to 15 carbon atoms, and a substituted or unsubstituted heteroalkynylene group of 2 to 15 carbon atoms;
ar is1、Ar2、Ar3、Ar4、Ar5And Ar6The substituents (B) are the same or different and each is independently selected from deuterium, a cyano group, a nitro group, a halogen, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having a halogen atom, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having a halogen atom, One of a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 24 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 20 carbon atoms.
Specifically, Ar is1、Ar2、Ar5And Ar6The same or different, each is independently selected from the group consisting of a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryl groupAnd one of substituted heteroaryl groups having 1 to 30 carbon atoms.
Specifically, Ar is3、Ar4One member selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 30 carbon atoms, and a substituted or unsubstituted heteroaralkylene group having 2 to 30 carbon atoms.
Specifically, the chemical formula 1 is one of the following structures:
Figure BDA0001918079770000101
Figure BDA0001918079770000111
Figure BDA0001918079770000121
Figure BDA0001918079770000131
ar in the invention3、Ar4And (b) one selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
An organic electroluminescent device based on the organic electroluminescent material comprises a cathode, an anode and more than one organic layers arranged between the cathode and the anode, wherein at least one of the more than one organic layers contains the electroluminescent material.
The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The organic layer containing the organic electroluminescent material is a hole transport layer.
The "alkyl group" unsubstituted in the present invention means an alkyl group having 1 to 20 carbon atoms, and includes a straight-chain alkyl group having 1 to 20 carbon atoms or a branched-chain alkyl group having 1 to 6 carbon atoms. For example, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl and the like. The substituted alkyl group having 1 to 20 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group, or the like.
The unsubstituted alkenyl group in the present invention refers to an alkenyl group having 2 to 20 carbon atoms, a straight-chain alkenyl group having 2 to 20 carbon atoms containing a carbon-carbon double bond, or a branched-chain alkenyl group having 1 to 6 carbon atoms. For example: vinyl, propenyl, allyl, isopropenyl, 2-butenyl, and the like. The substituted alkenyl group having 2 to 20 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group, or the like. The unsubstituted alkynyl group in the present invention refers to an alkynyl group having 2 to 24 carbon atoms, a straight-chain alkynyl group having 2 to 24 carbon atoms containing a carbon-carbon triple bond, or a branched-chain alkynyl group having 1 to 7 carbon atoms. For example: ethynyl, 2-propynyl, and the like. The substituted alkynyl group having 2 to 24 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group or the like.
The unsubstituted aryl group in the present invention means an aryl group having 6 to 30 carbon atoms. For example: phenyl, naphthyl, pyrenyl, dimethylfluorenyl, anthracenyl, phenanthrenyl,
Figure BDA0001918079770000141
Mesityl, azunyl, acenaphthenyl, biphenyl, benzanthryl, spirobifluorenyl, perylenyl, indenyl, and the like. The substituted aryl group having 6 to 30 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group, or the like.
The unsubstituted aralkyl group in the present invention means an aralkyl group having 7 to 30 carbon atoms. For example: tolyl, dimethylfluorenyl, and the like. The substituted aralkyl group having 7 to 30 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group, or the like.
The unsubstituted heteroaryl group in the present invention means a heteroaryl group having 2 to 30 carbon atoms. For example: pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, indolyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, and the like. Substituted heteroaryl having 2 to 30 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl, nitro, amino, or the like.
The unsubstituted cycloalkyl group in the present invention means a cycloalkyl group having 3 to 20 carbon atoms. For example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl and the like. The substituted cycloalkyl group having 3 to 20 carbon atoms means that at least one hydrogen atom is substituted with deuterium atom, F, Cl, I, CN, hydroxyl group, nitro group, amino group or the like.
Synthesis of Compound 1
Figure BDA0001918079770000151
1, 3-adamantanediol (5.0g,29.7mmol) and bromobenzene (10.3g,65.4mmol) were dissolved in dichloromethane (70mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under the nitrogen protection at 0 ℃, the mixture was stirred for 8 hours while maintaining the temperature and warmed to room temperature, and a 2mol/L aqueous solution of sodium hydroxide was added dropwise to the reaction mixture so that the pH of the reaction mixture became 7. Then, liquid separation is carried out, the organic phase is washed by water, magnesium sulfate is added for drying, and the solvent is removed under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as the mobile phase and then recrystallized using a dichloromethane/n-heptane system to give 6.8g of intermediate 1-A as a white solid with a yield of 51%.
Figure BDA0001918079770000152
2-bromotoluene (10.0g,58.5mmol), 2-amino-9, 9-dimethylfluorene (13.5g,64.3mmol), tris (dibenzylideneacetone) dipalladium (1.1g,1.2mmol), 2-dicyclohexyl-phosphorus-2, 4, 6-triisopropylbiphenyl (1.1g,2.3mmol) and sodium tert-butoxide (8.4g,87.7mmol) were added to toluene (150mL), heated to reflux temperature under nitrogen and stirred for 2 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/ethanol system to give 11.3g of light yellow solid intermediate 1-B in 65% yield.
Figure BDA0001918079770000161
Adding the intermediate 1-A (6.8g,15.2mmol), 1-B (10.0g,33.5mmol), tris (dibenzylideneacetone) dipalladium (0.6g, 0.6mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.5g,1.2mmol) and sodium tert-butoxide (4.4g,45.7mmol) into toluene (50mL), heating to reflux temperature under nitrogen protection, and stirring for 16 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization from dichloroethane to give 5.6g of compound 1 as a white solid in a yield of 42%. Mass spectrum M/z 883.5(M + H)+)
Synthesis of Compound 2
Figure BDA0001918079770000162
Adding 2-bromo-9, 9-dimethylfluorene (15.0g,54.9mmol), 4-aminobiphenyl (10.2g,60.4mmol), tris (dibenzylideneacetone) dipalladium (1.0g,1.1mmol), 2-dicyclohexyl-phosphorus-2, 4, 6-triisopropylbiphenyl (1.0g,2.2mmol) and sodium tert-butoxide (7.9g,82.4mmol) into toluene (200mL), heating to reflux temperature under nitrogen protection, stirring for 2 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give 14.4g of intermediate 2-B as a white solid in 73% yield.
Figure BDA0001918079770000171
Adding the intermediate 1-A (5.0g,11.2mmol), 2-B (8.9g,24.7mmol), tris (dibenzylideneacetone) dipalladium (0.4g, 0.4mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,0.9mmol) and sodium tert-butoxide (3.2g,33.6mmol) into toluene (50mL), heating to reflux temperature under nitrogen protection, and stirring for 12 h; then cooling to room temperature, filtering to obtain a solid, washing the solid with water and ethanol, and drying; the crude product was purified by recrystallization from dichloroethane to give 6.8g of compound 2 as a white solid in a yield of 60%. Mass spectrum M/z 1007.5(M + H)+)
Synthesis of Compound 3
Figure BDA0001918079770000172
Adding 2-bromo-9, 9-dimethylfluorene (15.0g,54.9mmol), 2-aminobiphenyl (10.2g,60.4mmol), tris (dibenzylideneacetone) dipalladium (1.0g,1.1mmol), 2-dicyclohexyl-phosphorus-2, 4, 6-triisopropylbiphenyl (1.0g,2.2mmol) and sodium tert-butoxide (7.9g,82.4mmol) into toluene (200mL), heating to reflux temperature under nitrogen protection, and stirring for 5 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford 11.9g of light brown solid intermediate 3-B in 60% yield.
Figure BDA0001918079770000173
Adding the intermediate 1-A (5.0g,11.2mmol), 3-B (8.9g,24.7mmol), tris (dibenzylideneacetone) dipalladium (0.4g, 0.4mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,0.9mmol) and sodium tert-butoxide (3.2g,33.6mmol) into toluene (50mL), heating to reflux temperature under nitrogen protection, and stirring for 16 h; then cooled to the chamberWashing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization from methylene chloride to give 5.2g of compound 3 as a white solid in a yield of 46%. Mass spectrum M/z 1007.5(M + H)+)
Synthesis of Compound 4
Figure BDA0001918079770000181
1, 3-adamantanediol (5.0g,29.7mmol) and 2-bromotoluene (11.2g,65.4mmol) were dissolved in dichloromethane (70mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under a nitrogen protection condition at 0 ℃, the mixture was stirred for 8 hours while maintaining the temperature and then warmed to room temperature, and a 2mol/L aqueous solution of sodium hydroxide was added dropwise to the reaction mixture so that the pH of the reaction mixture became 7. Then, liquid separation is carried out, the organic phase is washed by water, magnesium sulfate is added for drying, and the solvent is removed under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as the mobile phase and then recrystallized using a dichloromethane/n-heptane system to give 6.0g of intermediate 4-A as a white solid with a yield of 43%.
Figure BDA0001918079770000182
Bromobenzene (10g,63.7mmol), 2-amino-9, 9-dimethylfluorene (14.7g,70.1mmol), tris (dibenzylideneacetone) dipalladium (1.2g,1.3mmol), 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (1.2g,2.5mmol) and sodium tert-butoxide (9.2g,95.5mmol) were added to toluene (150mL), heated to reflux temperature under nitrogen protection, and stirred for 2 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/ethanol system to give 14.5g of intermediate 4-B as a white solid with a yield of 80%.
Figure BDA0001918079770000191
Adding the intermediate 4-A (6.0g,12.7mmol), 4-B (7.9g,27.8mmol), tris (dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,1.0mmol) and sodium tert-butoxide (3.6g,38.0mmol) into toluene (50mL), heating to reflux temperature under nitrogen protection, and stirring for 16 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give 6.1g of compound 4 as a white solid in 55% yield. Mass spectrum M/z 883.5(M + H)+)
Synthesis of Compound 5
Figure BDA0001918079770000192
1, 3-adamantanediol (5.0g,29.7mmol) and 2-fluorobromobenzene (11.4g,65.4mmol) were dissolved in dichloromethane (80mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under a nitrogen protection condition at 0 ℃, the mixture was stirred for 12 hours while maintaining the temperature and then warmed to room temperature, and a 2mol/L aqueous solution of sodium hydroxide was added dropwise to the reaction mixture so that the pH of the reaction mixture became 7. Then, liquid separation is carried out, the organic phase is washed by water, magnesium sulfate is added for drying, and the solvent is removed under reduced pressure; after purification of the crude product by silica gel column chromatography using n-heptane as the mobile phase, recrystallization was carried out using a dichloromethane/n-heptane system to obtain 8.1g of intermediate 5-A as a white solid in a yield of 57%.
Figure BDA0001918079770000201
Adding the intermediate 5-A (4.0g,8.3mmol), 4-B (5.2g,18.2mmol), tris (dibenzylideneacetone) dipalladium (0.3g, 0.3mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.3g,0.7mmol) and sodium tert-butoxide (2.4g,24.9mmol) into toluene (30mL), heating to reflux temperature under nitrogen protection, and stirring for 12 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; make itThe crude product was purified by recrystallization from dichloroethane to give 6.1g of compound 5 as a white solid in 83% yield. Mass spectrum M/z 891.5(M + H)+)
Synthesis of Compound 6
Figure BDA0001918079770000202
1, 3-adamantanediol (5.0g,29.7mmol) and 4-bromobiphenyl (15.2g,65.4mmol) were dissolved in dichloromethane (100mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under a nitrogen protection condition at 0 ℃, the mixture was stirred for 4 hours while maintaining the temperature and then warmed to room temperature, and a 2mol/L aqueous solution of sodium hydroxide was added dropwise to the reaction mixture so that the pH of the reaction mixture became 7. Then, the reaction solution was filtered to obtain a solid, which was washed with water and ethanol and dried, and the crude solid was purified by recrystallization using dichloromethane to obtain 7.7g of intermediate 6-A as a white solid with a yield of 43%.
Figure BDA0001918079770000211
Adding 2-bromonaphthalene (15.0g,72.4mmol), 2-methylaniline (8.5g,79.7mmol), tris (dibenzylideneacetone) dipalladium (1.3g, 1.4mmol), 2-dicyclohexylphosphorus-2, 4, 6-triisopropylbiphenyl (1.4g,2.9mmol) and sodium tert-butoxide (10.4g, 108.7mmol) into toluene (200mL), heating to reflux temperature under nitrogen protection, stirring for 3 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give 13.1g of intermediate 6-B as a white solid in 78% yield.
Figure BDA0001918079770000212
Intermediate 6-A (7.7g,12.9mmol), 6-B (6.6g,28.3mmol), tris (dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2-dicyclohexylphosphonium-2, 6-dimethoxybiphenyl (0.4g,1.0mmol) and tert-butylbenzeneAdding sodium alkoxide (3.7g,38.6mmol) into toluene (60mL), heating to reflux temperature under the protection of nitrogen, and stirring for 20 h; then cooling to room temperature, filtering the reaction solution to obtain a solid, washing with water and ethanol, and drying; the crude product was then purified by recrystallization from toluene to give 5.4g of compound 6 as a white solid in a yield of 46%. Mass spectrum M/z 903.5(M + H)+)
Synthesis of Compound 7
Figure BDA0001918079770000221
1, 3-adamantanediol (5.0g,29.7mmol) and 2-bromodibenzofuran (16.2g,65.4mmol) were dissolved in dichloromethane (100mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under the protection of nitrogen at-10 ℃, the mixture was stirred at the temperature for 4 hours, the mixture was warmed to room temperature, 2mol/L aqueous sodium hydroxide solution was added dropwise to the reaction mixture to adjust the pH of the reaction mixture to 7, the reaction mixture was filtered to obtain a solid, the solid was washed with water and ethanol and then dried, and the crude product was recrystallized and purified using dichloromethane to obtain 9.2g of intermediate 7-a as a white solid with a yield of 49%.
Figure BDA0001918079770000222
Bromobenzene (10.0g,63.7mmol), 4-aminobiphenyl (11.9g,70.1mmol), tris (dibenzylideneacetone) dipalladium (1.2g,1.3mmol), 2-dicyclohexylphosphorus-2, 4, 6-triisopropylbiphenyl (1.2g,2.5mmol) and sodium tert-butoxide (9.2g,95.5mmol) were added to toluene (150mL), heated to reflux temperature under nitrogen and stirred for 1 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/ethanol system to give 11.7g of intermediate 7-B as a pale yellow solid with a yield of 75%.
Figure BDA0001918079770000223
Adding the intermediate 7-A (9.2g,14.7mmol), 7-B (7.9g,32.3mmol), tris (dibenzylideneacetone) dipalladium (0.5g, 0.6mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.5g,1.2mmol) and sodium tert-butoxide (4.2g,44.1mmol) into toluene (80mL), heating to reflux temperature under nitrogen protection, and stirring for 8 h; then cooling to room temperature, filtering the reaction solution to obtain a solid, washing with water and ethanol, and drying; the crude product was then purified by recrystallization from dichloroethane to give 7.0g of compound 7 as a white solid in 50% yield. Mass Spectrum M/z 955.4(M + H)+)
Synthesis of Compound 8
Figure BDA0001918079770000231
1, 3-adamantanediol (5.0g,29.7mmol) and 2-bromodibenzothiophene (xxg, xxmmol) were dissolved in dichloromethane (100mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under the protection of nitrogen at-10 ℃, the mixture was stirred at the temperature for 6 hours, the mixture was warmed to room temperature, 2mol/L aqueous sodium hydroxide solution was added dropwise to the reaction mixture so that the pH of the reaction mixture became 7, the reaction mixture was filtered to obtain a solid, the solid was dried after washing with water and ethanol, and the crude product was purified by recrystallization using dichloroethane to obtain 7.6g of intermediate 8-a as a white solid with a yield of 39%.
Figure BDA0001918079770000232
Adding 2-bromotoluene (15.0g,87.7mmol), aniline (9.0g,96.5mmol), tris (dibenzylideneacetone) dipalladium (1.6g, 1.8mmol), 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (1.7g,3.5mmol) and sodium tert-butoxide (12.6g, 131.5mmol) into toluene (200mL), heating to reflux temperature under nitrogen protection, stirring for 1 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; after purification of the crude product by silica gel column chromatography using dichloromethane/n-heptane as eluent, recrystallization from ethanol gave 10.2g of light brown solid intermediate 8-B in 63% yield.
Figure BDA0001918079770000241
Adding the intermediate 8-A (7.6g,11.5mmol), 8-B (4.7g,25.4mmol), tris (dibenzylideneacetone) dipalladium (0.4g, 0.5mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,0.9mmol) and sodium tert-butoxide (3.3g,34.6mmol) into toluene (60mL), heating to reflux temperature under nitrogen protection, and stirring for 12 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give 4.7g of compound 8 as a white solid in 47% yield. Mass spectrum M/z 863.4(M + H)+)
Synthesis of Compound 9
Figure BDA0001918079770000242
1, 3-adamantanediol (5.0g,29.7mmol) and 2-bromonaphthalene (13.5g,65.4mmol) were dissolved in dichloromethane (80mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under the protection of nitrogen at-20 ℃, the mixture was stirred at the temperature for 4 hours, the mixture was warmed to room temperature, 2mol/L aqueous sodium hydroxide solution was added dropwise to the reaction mixture to adjust the pH of the reaction mixture to 7, a solid was obtained by filtration, the solid was washed with water and ethanol and dried, and the crude product was recrystallized and purified with dichloromethane to obtain 6.9g of intermediate 9-a as a white solid in a yield of 42%.
Figure BDA0001918079770000251
2-bromotoluene (10.0g,58.5mmol), 4-aminobiphenyl (10.9g,64.3mmol), tris (dibenzylideneacetone) dipalladium (1.1g,1.2mmol), 2-dicyclohexylphosphorus-2, 4, 6-triisopropylbiphenyl (1.1g,2.3mmol) and sodium tert-butoxide (8.4g,87.7mmol) were added to toluene (150mL), heated to reflux temperature under nitrogen protection and stirred for 2 h; then cooling to room temperature, filtering the reaction solution to obtain a solid, washing with water and ethanol, and drying; the crude product was then purified by recrystallization from toluene to give 7.0g of compound 9 as a white solid in 50% yield.
Figure BDA0001918079770000252
Adding intermediate 9-A (6.9g, xxmmol), 9-B (7.2g,27.8mmol), tris (dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,1.0mmol) and sodium tert-butoxide (3.6g,37.9mmol) into toluene (60mL), heating to reflux temperature under nitrogen, stirring for 16 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloroethane system to give 6.1g of compound 9 as a white solid in 53% yield. Mass spectrum M/z 903.5(M + H)+)
Synthesis of Compound 10
Figure BDA0001918079770000261
1, 3-adamantanediol (5.0g,29.7mmol) and 2-bromo-9, 9-dimethylfluorene (17.9g,65.4mmol) were dissolved in dichloromethane (100mL), trifluoromethanesulfonic acid (11.2g,74.3mmol) was slowly added dropwise under a nitrogen protection condition at-10 ℃, stirred for 4 hours under heat preservation, and then warmed to room temperature, and a 2mol/L aqueous solution of sodium hydroxide was added dropwise to the reaction solution so that the pH of the reaction solution became 7. Then, liquid separation is carried out, the organic phase is washed by water, magnesium sulfate is added for drying, and the solvent is removed under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as the mobile phase and then recrystallized using a dichloromethane/n-heptane system to give 8.9g of intermediate 10-A as a white solid with a yield of 44%.
Figure BDA0001918079770000262
Adding the intermediate 10-A (8.9g,13.1mmol), diphenylamine (4.9g,29mmol), tris (dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2-dicyclohexyl phosphorus-2, 6-dimethoxy-biphenyl (0.4g,1.0mmol) and sodium tert-butoxide (3.8g,39.3mmol) into toluene (70mL), heating to reflux temperature under nitrogen protection, and stirring for 6 h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization from toluene to give 6.9g of compound 10 as a white solid in 62% yield. Mass spectrum M/z 855.5(M + H)+)
Example 1: fabrication of organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0001918079770000263
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
On the experimental substrate (anode) was vacuum-evaporated m-MTDATA to form a Hole Injection Layer (HIL) having a thickness, and on the hole injection layer was vacuum-evaporated compound 1 to form a hole injection layer having a thickness
Figure BDA0001918079770000271
A Hole Transport Layer (HTL).
Depositing TCTA on the hole transport layer to a thickness of
Figure BDA0001918079770000272
Electron Blocking Layer (EBL).
Using alpha, beta-AND as main body, simultaneously doping 4,4' - (3, 8-diphenylpyrene-1, 6-diylbis (N, N-diphenylaniline) to form a layer with thickness of
Figure BDA0001918079770000273
The light emitting layer (EML).
DBimiBphen and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0001918079770000274
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0001918079770000275
Then magnesium (Mg) and silver (Ag) were mixed at a ratio of 9:1, and vacuum-evaporated on the electron injection layer to form an Electron Injection Layer (EIL) having a thickness of
Figure BDA0001918079770000276
The cathode of (1).
Further, N- (4- (9H-carbazol-9-yl) phenyl) -4'- (9H-carbazol-9-yl) -N-phenyl- [1,1' -biphenyl ] -4-amine having a thickness of 65nm was deposited on the cathode to form a capping layer (CPL), thereby completing the production of an organic light-emitting device.
Examples 2 to 10
Organic electroluminescent devices were produced in the same manner as in example 1, except that the compounds shown in table 1 were each used in forming the hole transport layer.
That is, the compound 2 was used in example 2 to fabricate an organic electroluminescent device, the compound 3 was used in example 3 to fabricate an organic electroluminescent device, and the corresponding compounds 4 to 10 were used in examples 4 to 10 to fabricate an organic electroluminescent device, respectively, and the device properties are shown in table 1.
Comparative examples 1 to 3
In the above example 1, an organic electroluminescent device was manufactured in the same manner as in example 1, except that NPB, compound a, and compound B were used as the hole transport layer instead of compound 1.
Namely, comparative example 1 produced an organic electroluminescent device using NPB, comparative example 2 produced an organic electroluminescent device using compound a, and comparative example 3 produced an organic electroluminescent device using compound B, and the device properties are shown in table 1.
For the organic electroluminescent device prepared as above, at 10mA/cm2The device performance was analyzed under the conditions of (1), and the results are shown in table 1 below.
Figure BDA0001918079770000281
TABLE 1 device Performance
Examples Compound (I) V lm/W Cd/A Cd/m2 Colour(s) EQE(％) T50(hr)
1 Compound 1 3.95 5.7 7.1 772.3 Blue color 14.4 3000
2 Compound 2 3.90 6 7.4 745.2 Blue color 14.7 3050
3 Compound 3 3.88 6.1 7.5 758.9 Blue color 14.9 2900
4 Compound 4 3.89 5.5 6.9 751.8 Blue color 13.8 3300
5 Compound 5 3.89 6.2 7.7 724.5 Blue color 14.9 2900
6 Compound 6 3.88 5.3 6.9 728.4 Blue color 13.3 3400
7 Compound 7 3.89 5.4 7.0 734.7 Blue color 13.8 3100
8 Compound 8 3.89 6 7.4 717.7 Blue color 14.4 3000
9 Compound 9 3.87 5.2 6.4 730.1 Blue color 13.1 3400
10 Compound 10 3.90 6 7.4 732.4 Blue color 14.7 2980
Comparative example 1 NPB 4.00 5.6 6.5 549 Blue color 6.9 1650
Comparative example 2 Compound A 4.10 6.0 6.7 627 Blue color 10.9 2600
Comparative example 3 Compound B 3.91 5.7 6.8 665.5 Blue color 10.9 2850
Referring to Table 1, in the case of examples 1 to 10 using the compound of the present invention as a hole transporting layer, the voltage (V), the current efficiency (Cd/A), the luminance (Cd/m) were compared with those of comparative examples 1 to 32) And External Quantum Efficiency (EQE) and half-life (T50) exhibit better characteristics. Therefore, the device manufactured by using the compound of the invention has the characteristics of reducing the driving voltage, improving the luminous efficiency and prolonging the service life.
In conclusion, the compound of the present invention is used as a hole transport layer of an organic electroluminescent device, so that the organic electroluminescent device comprising the compound has lower driving voltage, higher luminous efficiency and better lifetime.
As can be seen from table 1 of the results of the organic electroluminescent device of the example, the compound of the present invention introduces adamantane as a new core group based on the bis (triarylamine) symmetry structure, changes the molecular morphology, and decreases the symmetry of the structure. When it is used as a hole transporting material, the hole transporting performance of the material can be further improved. Therefore, an organic electroluminescent device having excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency, and half-life can be manufactured.
The above examples are merely further illustrative of the compounds of the present invention and the scope of the invention as claimed is not limited thereto. It will be apparent to those skilled in the art that various additions and modifications can be made to the present invention without departing from the scope of the technical idea of the present invention as set forth in the claims of the present invention.

Claims (4)

1. An organic electroluminescent material, characterized in that the material is one of the following structures:
Figure FDA0003177854020000011
2. an organic electroluminescent device comprising a cathode, an anode and one or more organic layers between the cathode and the anode, wherein at least one of the one or more organic layers between the cathode and the anode comprises the electroluminescent material of claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
4. The organic electroluminescent device according to claim 2, wherein the organic layer containing the electroluminescent material according to claim 1 is a hole transport layer.
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