CN112110885B - Hole transport material, organic electroluminescent device and display device - Google Patents

Hole transport material, organic electroluminescent device and display device Download PDF

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CN112110885B
CN112110885B CN202011049616.XA CN202011049616A CN112110885B CN 112110885 B CN112110885 B CN 112110885B CN 202011049616 A CN202011049616 A CN 202011049616A CN 112110885 B CN112110885 B CN 112110885B
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hole transport
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organic electroluminescent
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CN112110885A (en
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邢其锋
丰佩川
陈雪波
单鸿斌
胡灵峰
陈跃
马艳
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Yantai Xianhua Chem Tech Co ltd
Yantai Jingshi Materials Genomic Engineering Research Institute
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Yantai Jingshi Materials Genomic Engineering Research Institute
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Abstract

The invention discloses a hole transport material with a general formula I, which can be used as a hole transport layer of an organic electroluminescent device in a display device. The hole transport material has the parent structure of the diarylamine of fluorene substituted trimellitic benzene, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong hole transition capability, can effectively reduce the voltage of a device when being used as a hole transport layer material, and improves the service life of the material.

Description

Hole transport material, organic electroluminescent device and display device
Technical Field
The invention relates to the technical field of luminous display, in particular to a hole transport material, an organic electroluminescent device and a display device.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by current and voltage under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (OLED) has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, etc., compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, the response speed can reach 1000 times of the liquid crystal display, and the manufacturing cost is lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advancement of OLED technology in the two fields of illumination and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is usually the result of the optimized collocation of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, film can be formed on any substrate by a vapor deposition or spin coating method, and flexible display and large-area display can be realized; the optical properties, electrical properties, stability, etc. of the materials can be tuned by changing the structure of the molecules, and the choice of materials has a large space, and in the most common OLED device structures, the following types of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, a light emitting material (dye or doped guest material) of each color, a corresponding host material, and the like.
Disclosure of Invention
In order to improve the luminous efficiency and prolong the life of an organic light-emitting electroluminescent device, the invention provides a hole transport material, an organic electroluminescent device and a display device.
The hole transport material has a structure shown as a formula I:
a in formula I has a structure shown in formula II:
wherein,,
Ar 1 -Ar 3 selected from C unsubstituted or substituted by Ra 6 -C 30 Aryl or C which is unsubstituted or substituted by Ra 3 -C 30 A heteroaromatic group;
l is selected from chemical bond, C 6 -C 30 Arylene group or C of (C) 3 -C 30 Is a heteroarylene group;
R 1 、R 2 selected from C 1 -C 10 Alkyl, C 1 -C 6 Cycloalkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 A heteroaromatic group;
x is selected from O, S, CR 3 R 4 Or NR (NR) 5 ，Z 1 -Z 8 Selected from CR or N;
R 3 、R 4 independently selected from C 1 -C 10 Alkyl, C 1 -C 6 Cycloalkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl;
R 5 selected from C substituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl;
r is selected from hydrogen, C 6 -C 30 Arylene group or C of (C) 3 -C 30 Is a heteroarylene group;
the substituents Ra of the individual radicals may be identical or different from one anotherIndependently selected from hydrogen, halogen, nitro, cyano, and C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
Preferably Ar 1 -Ar 3 Selected from one of the following unsubstituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, aromatic amines, or carbazolyl; r is R 1 、R 2 Selected from methyl, ethyl, cyclopentyl, cyclohexyl, one of the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, aromatic amines, or carbazolyl; r is R 3 、R 4 Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, or carbazolyl; r is R 5 Selected from one of the following groups, unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carboAn azole group; l is selected from a bond, or one of the subunits of the following compounds, unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, or carbazole.
The invention also discloses a specific structure of the hole transport material shown in the formulas A1-A30:
the hole transport material has the parent structure of the diarylamine of fluorene substituted trimellitic benzene, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong hole transition capability, can effectively reduce the voltage of a device when being used as a hole transport layer material, and improves the service life of the material.
The fluorene-substituted benzene-trimellitic biaryl amine derivative is applied to a hole transport layer, has a proper energy level with adjacent layers, is favorable for hole injection and migration, can effectively reduce the starting voltage, has a higher hole migration rate, and can realize good luminous efficiency in a device. The compound provided by the invention has a larger conjugate plane, is favorable for molecular accumulation, shows good thermodynamic stability, and shows long service life in a device.
The present invention also provides an organic electroluminescent device comprising at least an anode electrode, a hole transporting layer, a light emitting layer and a cathode electrode, wherein the hole transporting layer is at least one selected from the above compounds, and in the present invention, the kind and structure of the organic electroluminescent device are not particularly limited as long as the hole transporting material provided by the present invention can be used.
For convenience, the present application will be described with respect to an organic light emitting diode, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the organic luminescent material of the present invention are within the scope of the present invention.
In general, an organic light emitting diode includes first and second electrodes on a substrate, and an organic material layer between the electrodes, and the organic material layer may have a multi-layered structure, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the present invention, the substrate is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, such as glass, polymer materials, glass with TFT devices, polymer materials, and the like, may be used.
In the present invention, the anode electrode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) The transparent conductive material such as zinc oxide (ZnO) may be a metal material such as silver or an alloy thereof, aluminum or an alloy thereof, an organic conductive material such as PEDOT (poly 3, 4-ethylenedioxythiophene) or a multilayer structure of the above materials. The cathode material is not particularly limited and may be selected from, but not limited to, metals such as magnesium silver mixture, liF/Al, ITO, al, metal mixtures, oxides, and the like.
The hole transport layer located between the light emitting layer and the anode may be selected from at least one of the hole transport materials obtained in the present invention. The present invention also enumerates the materials that are currently commonly used as hole transport layers, as represented by formulas HT-1 through HT-32:
the light emitting layer light emitting material may include a host material and a light emitting dye, and the host material may be selected from at least one of the following GPH-1 to GPH-80 compounds:
preferably, the light emitting layer 5 contains a phosphorescent dopant, and the dopant may be at least one selected from the following RPD-1 to RPD-28 compounds, and the amount of the dopant is not particularly limited and may be an amount known to those skilled in the art.
The electron transport layer may comprise at least one of the following known electron transport materials ET-1 to ET-57:
an electron injection layer located between the electron transport layer and the cathode may be further included, and the electron injection layer is not particularly limited, and electron injection materials known in the art may be used, for example, may include, but not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 At least one of materials such as BaO, na, li, ca.
A third aspect of the present invention provides a display device comprising the above organic electroluminescent device, the display device of the present invention including, but not limited to, an organic light emitting diode, a display, a television, a tablet computer, a mobile communication terminal, etc.
Detailed Description
The invention is described below in connection with examples which are given solely for the purpose of illustration and are not intended to limit the scope of the invention.
1. Synthesis of hole transport materials
Synthesis of example 1, A1
Into a reaction flask were charged 100mmol of 3-chloro-5-bromophenol, 100mmol of 2- (9, 9-dimethylfluorene) -boric acid, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh) 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of 3-chloro-5-bromophenol;
100mmol of M1, 100mmol of diphenylamine, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of dimethylbenzene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture to react for 12 hours at 120 ℃, the reactant is cooled to room temperature after the reaction is finished, water is added into the mixture, the mixture is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2, wherein the addition amount of Pd (dba) is 1mol% of M1;
100mmol of M2, 200ml of dichloromethane and 100mmol of triethylamine are added into a reaction bottle, 100mmol of trifluoromethanesulfonic anhydride is dropwise added at 0 ℃ to react for 12 hours at room temperature, water is added after the reaction is finished, an organic phase is separated, and the mixture is concentrated to obtain an intermediate M3;
100mmol of p-bromoiodobenzene, 100mmol of 2-bromodibenzofuran-aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of dimethylbenzene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture, the mixture is reacted for 12 hours at 120 ℃, after the reaction is finished, the reactant is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4, wherein the addition amount of Pd (dba) is 1mol% of p-bromoiodobenzene;
into a reaction flask were charged 100mmol of M4, 120mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 1mol% of Pd (dppf) Cl 2 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing with toluene to obtain white powder M5, wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M4;
into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A1, wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
The results of the hydrogen spectrum characterization of A1 are as follows:
1 H NMR(400MHz,Chloroform)δ8.15(d,J＝12.0Hz,2H),8.08(dd,J＝10.8,8.4Hz,4H),7.90(s,1H),7.79(d,J＝12.0Hz,2H),7.63–7.52(m,8H),7.46(s,1H),7.35(dd,J＝8.8,7.2Hz,4H),7.28–7.21(m,7H),7.08(s,2H),7.00(s,1H),1.69(s,6H).
the reaction scheme is as follows:
synthesis of examples 2 and A5
Into a reaction flask were charged 100mmol of 3-chloro-5-bromophenol, 100mmol of 2- (9, 9-dimethylfluorene) -boric acid, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh) 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of 3-chloro-5-bromophenol;
100mmol of M1, 100mmol of 4-biphenyl-aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of xylene are added into a reaction bottle, 1mol% of Pd (dba) is added, the reaction is carried out for 12 hours at 120 ℃, after the reaction is finished, the reactant is cooled to room temperature, water is added, filtration and water washing are carried out, the obtained solid is recrystallized and purified by toluene, and white powder M2 is obtained, wherein the addition amount of Pd (dba) is 1mol% of M1;
100mmol of M2, 200ml of dichloromethane and 100mmol of triethylamine are added into a reaction bottle, 100mmol of trifluoromethanesulfonic anhydride is dropwise added at 0 ℃ to react for 12 hours at room temperature, water is added after the reaction is finished, an organic phase is separated, and the mixture is concentrated to obtain an intermediate M3;
100mmol of p-bromoiodobenzene, 100mmol of 2-bromodibenzofuran-2-naphthylamine, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of dimethylbenzene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture to react for 12 hours at 120 ℃, after the reaction is finished, the reactant is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4, wherein the addition amount of Pd (dba) is 1mol% of p-bromoiodobenzene;
into a reaction flask were charged 100mmol of M4, 120mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 1mol% of Pd (dppf) Cl 2 Reacting at 120deg.C for 12h, and after the reactionThe reaction was cooled to room temperature, water was added, filtration and washing with water, and the resulting solid was purified by recrystallization from toluene to give a white powder M5 in which Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M4;
into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A5, wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
The results of the hydrogen spectrum characterization of A5 are as follows:
1 H NMR(400MHz,Chloroform)δ8.22(s,1H),8.09(s,1H),7.98(s,1H),7.94(d,J＝10.0Hz,2H),8.07–7.69(m,10H),7.62(s,1H),7.61–7.48(m,9H),7.46–7.29(m,9H),7.24(d,J＝8.4Hz,3H),7.13–7.03(m,4H),7.00(s,1H),1.69(s,6H).
the reaction scheme is as follows:
example 3 Synthesis of A12
Into a reaction flask were charged 100mmol of 3-chloro-5-bromophenol, 100mmol of 2- (9, 9-dimethylfluorene) -boric acid, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh) 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of 3-chloro-5-bromophenol;
100mmol of M1, 100mmol of 2-naphthyl-aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of xylene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture, the mixture is reacted for 12 hours at 120 ℃, after the reaction is finished, the mixture is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2, wherein the addition amount of Pd (dba) is 1mol% of M1;
100mmol of M2, 200ml of dichloromethane and 100mmol of triethylamine are added into a reaction bottle, 100mmol of trifluoromethanesulfonic anhydride is dropwise added at 0 ℃ to react for 12 hours at room temperature, water is added after the reaction is finished, an organic phase is separated, and the mixture is concentrated to obtain an intermediate M3;
100mmol of M-bromoiodobenzene, 100mmol of 2-bromodibenzofuran-aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of dimethylbenzene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture, the mixture is reacted for 12 hours at 120 ℃, after the reaction is finished, the reactant is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M4, wherein the addition amount of Pd (dba) is 1mol% of p-bromoiodobenzene;
into a reaction flask were charged 100mmol of M4, 120mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 1mol% of Pd (dppf) Cl 2 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing with toluene to obtain white powder M5, wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M4;
into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A12, wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
The results of the A12 hydrogen spectrum are shown below:
1 H NMR(400MHz,Chloroform)δ8.16(d,J＝12.0Hz,2H),8.00(d,J＝8.4Hz,2H),7.90(s,1H),7.86(s,1H),7.78(s,1H),7.71(s,1H),7.39(dd,J＝12.0,8.0，8H),7.64–7.45(m,7H),7.25(dd,J＝12.0,8.0Hz,6H),7.20–7.10(m,7H),7.08(s,1H),7.00(s,2H),1.69(s,6H).
the reaction scheme is as follows:
example 4 Synthesis of A23
Into a reaction flask were charged 100mmol of 3-chloro-5-bromophenol, 100mmol of 2- (9, 9-dimethylfluorene) -boric acid, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh) 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of 3-chloro-5-bromophenol;
100mmol of M1, 100mmol of 2-naphthyl-aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of xylene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture, the mixture is reacted for 12 hours at 120 ℃, after the reaction is finished, the mixture is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2, wherein the addition amount of Pd (dba) is 1mol% of M1;
100mmol of M2, 200ml of dichloromethane and 100mmol of triethylamine are added into a reaction bottle, 100mmol of trifluoromethanesulfonic anhydride is dropwise added at 0 ℃ to react for 12 hours at room temperature, water is added after the reaction is finished, an organic phase is separated, and the mixture is concentrated to obtain an intermediate M3;
into a reaction flask were charged 100mmol of 3-chloro-5-bromoiodobenzene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M4, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of 3-chloro-5-bromoiodobenzene;
100mmol of M4, 100mmol of 2- (9, 9-dimethylfluorene) -aniline, 28.8g of sodium tert-butoxide (300 mmol) and 800ml of xylene are added into a reaction bottle, 1mol% of Pd (dba) is added into the mixture, the mixture is reacted for 12 hours at 120 ℃, after the reaction is finished, the mixture is cooled to room temperature, water is added into the mixture, the mixture is filtered and washed with water, and the obtained solid is recrystallized and purified by toluene to obtain white powder M5, wherein the addition amount of Pd (dba) is 1mol% of M4;
into a reaction flask were charged 100mmol of M5, 120mmol of pinacol diboronate, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 1mol% of Pd (dppf) Cl 2 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing with toluene to obtain white powder M6, wherein Pd (dppf) Cl 2 The amount of (2) added is 1mol% of M5;
into a reaction flask were charged 100mmol of M3, 100mmol of M6, 41.4g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water and Pd (PPh 3 ) 4 Reacting at 120deg.C for 12 hr, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A23, wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M3.
The results of the A23 hydrogen spectrum are shown below:
1 H NMR(400MHz,Chloroform)δ8.29(s,1H),8.09(s,1H),7.90(s,2H),7.86(s,1H),7.82–7.73(m,4H),7.71(s,1H),7.62(s,1H),7.60–7.47(m,8H),7.47–7.31(m,11H),7.24(d,J＝6.4Hz,4H),7.10(t,J＝7.6Hz,6H),7.00(s,2H),1.69(s,12H).
the reaction scheme is as follows:
2. preparation of organic electroluminescent device
Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
placing the above glass substrate with anode in vacuum cavity, and vacuumizing to less than 10 -5 Torr, aboveVacuum evaporation HT-4 and 3% of p-type dopant (p-doping) by mass ratio on the anode layer film, wherein the evaporation rate is 0.1nm/s, the evaporation film thickness is 10nm, and the material of the hole injection layer and the p-type dopant are as follows:
vacuum evaporating the hole transport materials obtained in examples 1 to 4 as a hole transport layer on the hole injection layer at an evaporation rate of 0.1nm/s and an evaporation total film thickness of 80nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporating by utilizing a multi-source co-evaporation method, adjusting the evaporation rate of the main material GHP-16 to be 0.1nm/s, wherein the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total evaporation film thickness is 30nm;
vacuum evaporating an electron transport layer on the light-emitting layer, wherein a material ET42 is selected as the electron transport material, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an aluminum layer with the thickness of 150nm is used as a cathode of the device.
Comparative example 1
The hole transport material of the organic electroluminescent device was replaced with HT27, and the rest was unchanged.
The organic electroluminescent devices of examples 1 to 4 and comparative example 1 were subjected to the following performance measurements:
under the same brightness, using a digital source meter and a brightness meter to measure the driving voltage and current efficiency of the organic electroluminescent device and the service life of the device, specifically, increasing the voltage at a rate of 0.1V per second to measure that the brightness of the organic electroluminescent device reaches 5000cd/m 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: at 5000cd/m using a luminance meter 2 Maintaining constant current at brightness, measuring the electromechanical systemThe brightness of the light-emitting device was reduced to 4750cd/m 2 Time in hours. The results are shown in Table 1.
TABLE 1 organic electroluminescent device Performance
Required brightness (cd/m) 2 ) Drive voltage/V Current efficiency (cd/A) Lifetime (LT 95)/h
Example 1 5000.00 3.7 40.5 190
Example 2 5000.00 3.8 40.3 188
Example 3 5000.00 3.8 39.6 192
Example 4 5000.00 3.7 38.8 188
Comparative example 1 5000.00 4.0 35.2 140
As can be seen from Table 1, the hole transport materials obtained in examples 1 to 4 are effective in reducing the driving voltage, improving the current efficiency, and prolonging the lifetime of the device, and are excellent hole transport materials.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.

Claims (3)

1. A hole transport material characterized by having the structure shown below:
2. an organic electroluminescent device comprising an anode electrode, a hole transport layer, a light emitting layer, and a cathode electrode, wherein the hole transport layer comprises at least one of the hole transport materials of claim 1.
3. A display device comprising the organic electroluminescent device of claim 2.
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WO2016072691A1 (en) * 2014-11-05 2016-05-12 덕산네오룩스 주식회사 Organic electronic device and display device using composition for organic electronic device
KR20160059609A (en) * 2014-11-19 2016-05-27 덕산네오룩스 주식회사 Display device using a composition for organic electronic element, and an organic electronic element thereof
CN107275519A (en) * 2016-04-06 2017-10-20 三星显示有限公司 Organic light emitting apparatus

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WO2016072691A1 (en) * 2014-11-05 2016-05-12 덕산네오룩스 주식회사 Organic electronic device and display device using composition for organic electronic device
KR20160059609A (en) * 2014-11-19 2016-05-27 덕산네오룩스 주식회사 Display device using a composition for organic electronic element, and an organic electronic element thereof
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