CN111548353B - Organic luminescent material and organic electroluminescent device - Google Patents

Organic luminescent material and organic electroluminescent device Download PDF

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CN111548353B
CN111548353B CN202010453418.3A CN202010453418A CN111548353B CN 111548353 B CN111548353 B CN 111548353B CN 202010453418 A CN202010453418 A CN 202010453418A CN 111548353 B CN111548353 B CN 111548353B
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reaction
luminescent material
organic luminescent
electroluminescent device
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CN111548353A (en
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邢其锋
丰佩川
单鸿斌
胡灵峰
陈跃
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The invention relates to an organic luminescent material, which has a structure shown in the following general formula (I):

Description

Organic luminescent material and organic electroluminescent device
Technical Field
The invention relates to an organic luminescent material and an organic electroluminescent device, belonging to the technical field of luminescent materials.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light under the excitation of electric current and 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 property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the material has a large space to select. In the most common OLED device structures, the following classes 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
The invention provides an organic luminescent material and an organic electroluminescent device using the same, aiming at the defects of the prior art.
The technical scheme for solving the technical problems is as follows: an organic light-emitting material having a structure represented by the following general formula (I):
Figure BDA0002508406240000011
/>
Figure BDA0002508406240000021
wherein Ar is 1 ，Ar 2 Selected from C unsubstituted or substituted by Ra 6 -C 30 An aromatic group of (a);
R 1 -R 4 identical or different and independently of one another selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl, wherein, adjacent R 1 -R 4 Can be connected into a ring;
l is selected from chemical bond, C 6 -C 30 Or C 3 -C 30 Is a heteroarylene group;
x and Y are selected from O, S, CR 5 R 6 、NR 7 ；
R 5 、R 6 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 is R 7 Selected from C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl;
a is selected from the group consisting of formula (II) wherein Z 1 -Z 8 Any one of the (B) is a connecting site of a formula (II) and a formula (I);
Z 1 -Z 8 selected from CR or N, R is selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, wherein adjacent R can be connected to form a ring;
the substituents Ra of the various groups are the same or different and are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 Alkyl group of (C),Phenyl, biphenyl, terphenyl, or naphthyl.
Preferably, said Ar 1 ，Ar 2 Selected from any one of the following substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, and carbazolyl.
Preferably, said R 1 -R 4 Independently of each other, selected from any of the following groups, which are 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, carbazole groups.
Preferably, said R 5 And R is 6 Independently of each other, selected from any one of the following groups, which are 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, carbazole groups.
Preferably, said R 7 Any one of the following groups, which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinolylAn oxinyl group, cinnolinyl group, naphthyridinyl group, triazinyl group, pyridopyrazinyl group, furyl group, benzofuryl group, dibenzofuryl group, aza-dibenzofuryl group, thienyl group, benzothienyl group, dibenzothienyl group, aza-dibenzothienyl group, 9-dimethylfluorenyl group, spirofluorenyl group, arylamine, carbazole group.
Preferably, L is selected from a bond, or a subunit of any one 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, carbazole.
Preferably, said R is selected from hydrogen, methyl, ethyl, cyclopentyl, cyclohexyl, any 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, carbazole groups.
Preferably, the organic light emitting material is selected from any one of the following compounds A1 to a 30:
Figure BDA0002508406240000031
/>
Figure BDA0002508406240000041
the invention also discloses an organic electroluminescent device, which comprises the organic luminescent material.
The organic light emitting material is used as a hole transporting material of the organic electroluminescent device.
The beneficial effects of the invention are as follows:
the organic luminescent material disclosed by the invention has a parent structure of diversified condensed heterocycles, has high bond energy among atoms and good thermal stability, and can effectively reduce the voltage of a device and prolong the service life of the material when being used as a hole transport layer material.
The organic luminescent material is a derivative of diversified condensed heterocycles, is applied to a hole transport layer, has proper energy level with adjacent layers, is favorable for hole injection and migration, can effectively reduce the starting voltage, has 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.
Meanwhile, the preparation process of the organic luminescent material is simple and feasible, raw materials are easy to obtain, and the organic luminescent material is suitable for industrial production.
Detailed Description
The following detailed description of the present invention will provide further details in order to make the above-mentioned objects, features and advantages of the present invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The present invention may be embodied in many other forms than described herein and similarly modified by those skilled in the art without departing from the spirit of the invention, whereby the invention is not limited to the specific embodiments disclosed below.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The organic luminescent material can be used as a hole transport material in an organic electroluminescent device.
In the present application, the kind and structure of the organic electroluminescent device are not particularly limited as long as the organic luminescent material provided in the present application 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. For example, the organic material layer may include 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 application, the substrate is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, glass with TFT devices, polymer materials, and the like can be used.
In the present application, the anode material is not particularly limited, and may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) The transparent conductive material such as zinc oxide (ZnO), the metal material such as silver and its alloy, aluminum and its alloy, the organic conductive material such as PEDOT (poly 3, 4-ethylenedioxythiophene), the multilayer structure of the above materials, and the like.
In the present application, the cathode material is not particularly limited, and may be selected from, for example, materials such as magnesium silver mixture, liF/Al, ITO, etc., metal mixtures, oxides, etc.
In this application, the organic electroluminescent diode (OLED) may further include a hole injection layer, a hole transport layer, etc. between the light emitting layer and the anode, and these layers may be used, but are not limited to, at least one of HT-1 to HT-31 listed below, and these materials may be used singly or in combination of two or more.
Figure BDA0002508406240000061
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Figure BDA0002508406240000071
In the present application, the device light-emitting layer may comprise a host material and a light-emitting dye, wherein the host material includes, but is not limited to, a combination of one or more of the conventional materials shown in GPH-1 through GPH-80, below.
Figure BDA0002508406240000072
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Figure BDA0002508406240000081
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Figure BDA0002508406240000091
In a preferred embodiment of the present invention, the light-emitting layer employs phosphorescence-electroluminescence technology. The light emitting layer thereof is doped with a phosphorescent dopant which may be selected from, but is not limited to, one or more combinations of the below listed RPD-1 through RPD-28.
Figure BDA0002508406240000101
The electron transport material includes, but is not limited to, a combination of one or more of the following listed ET-1 to ET-57 materials. The electron transport materials of the present application may be used in combination with one or more of these materials.
Figure BDA0002508406240000111
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Figure BDA0002508406240000121
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Figure BDA0002508406240000131
In addition, the OLED device may further include an electron injection layer between the electron transport layer and the cathode, the material of the electron injection layer is not particularly limited, and may include, for example, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 BaO, na, li, ca, etc. or a combination of several materials.
In this application, HT-28 was used for comparison experiments with the organic luminescent materials of the present invention.
The method for synthesizing the compound of the present application is not particularly limited, and may be synthesized by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of Compound A1
Figure BDA0002508406240000141
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 1-dibenzofuran boric acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorene) -4-aminobiphenyl, 40g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-tert-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with xylene to obtain yellow powder A1. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
M/Z: theory, 692.86; experimental values, 692.3.
1 H NMR(400MHz,Chloroform)δ8.16-8.02(m,2H),7.90-7.75(m,4H),7.62(s,1H),7.61–7.46(m,6H),7.43–7.29(m,4H),7.24(s,1H),7.19(d,J＝7.2Hz,8H),7.01-6.83(m,4H),1.69(s,6H).
Synthesis example 2: synthesis of Compound A5
Figure BDA0002508406240000151
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 1-dibenzothiophene boronic acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorenamine) -3- (N-phenylcarbazole), 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with xylene to obtain yellow powder A5. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ8.19(d,J＝9.2Hz,2H),7.92(dd,J＝12.0,8.4Hz,4H),7.63(d,J＝10.8Hz,3H),7.57(d,J＝10.0Hz,3H),7.49(d,J＝10.0Hz,2H),7.40(s,1H),7.38–7.29(m,7H),7.24(s,1H),7.19(d,J＝10.0Hz,4H),7.01-6.88(m,6H),1.69(s,6H).
M/Z: theory, 798.02; experimental values, 797.8.
Synthesis example 3: synthesis of Compound A9
Figure BDA0002508406240000161
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 4-N-phenylcarbazole boron ester, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, and passingThe solid obtained was purified by recrystallization from toluene after filtration and washing with water to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorenamine) -2- (dibenzothiophene), 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder A9. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ8.50(d,J＝10.0Hz,2H),7.90(s,1H),7.80(d,J＝8.4Hz,3H),7.71–7.54(m,5H),7.54–7.48(m,4H),7.42–7.14(m,6H),7.09(d,J＝12.0Hz,4H),7.01(s,1H),6.58-6.40(m,7H),1.69(s,6H).
M/Z: theory, 798.02; experimental values, 797.9.
Synthesis example 4: synthesis of Compound A17
Figure BDA0002508406240000171
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 4-N-phenylcarbazole boron ester, 40g of potassium carbonate (300 mmol), 800ml THF and 200ml water, and 1mol% Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chloro-benzoate, 100mmol of 3-pyridineboronic acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) bromo-5-chloro-benzoic acid methyl ester added was 1mol%.
M4 (100 mmol,1 eq), glacial acetic acid 200ml,100ml concentrated sulfuric acid were heated to reflux and reacted for 12h. After the reaction, water was added, and the precipitated solid was filtered to obtain intermediate M5.
100mmol of intermediate M5 is dissolved in 500ml of THF, the temperature is reduced to 0 ℃, 220mmol of methyl magnesium chloride is added dropwise, and the temperature is naturally raised after the dropwise addition is completed, and the reaction is carried out for 8 hours. After the reaction, water is added into the reaction liquid, and the organic phase is extracted and concentrated to obtain an intermediate M6.
Into the reaction flask were charged 100mmol of M6, 100mmol of 2 aminobiphenyl, 40g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-tert-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder M7. Wherein, the addition amount of Pd (dba) is 1mol% of M6.
Into the reaction flask were charged 100mmol of M3, 100mmol of M7, 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder a17. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1 H NMR(CDCl3,400MHz)δ8.64(s,1H),8.17(d,J＝7.2Hz,2H),7.95(d,J＝8.0Hz,4H),7.74(s,1H),7.67(d,J＝10.0Hz,2H),7.58-7.50(m,5H),7.48–7.33(m,6H),7.33(d,J＝6.8Hz,2H),7.32–7.07(m,4H),7.11(d,J＝10.0Hz,1H),7.08-7.01(m,2H),1.75(s,6H).
M/Z: theory, 693.85; experimental values, 693.2.
Other compounds of the present application can be synthesized by selecting appropriate starting materials according to the concepts of examples 1-4, and any other appropriate methods and starting materials can be selected for synthesis.
The invention also discloses an organic electroluminescent device which comprises the organic luminescent material.
In the present application, the method of manufacturing the OLED device is not particularly limited, and may be manufactured using any method known in the art.
Application example 1
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;
the above-mentioned anode is provided withIs placed in a vacuum cavity, vacuumized to be less than 10 -5 Vacuum evaporating HT-11 on the anode layer film as a hole injection layer at an evaporation rate of 0.1nm/s and an evaporation film thickness of 10nm;
vacuum evaporating A1 material on the hole injection layer to serve as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 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 luminescent layer, wherein a material ET-26 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 Al layer with the thickness of 150nm serves as a cathode of the device.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples and comparative examples were measured using a digital source meter and a luminance meter at the same luminance, specifically, the luminance of the organic electroluminescent devices was measured to be 5000cd/m by increasing the voltage at a rate of 0.1V per second 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 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 4750cd/m 2 Time in hours.
Application examples 2 to 6
The organic light-emitting materials A4, A9, a17 according to the present invention were used as hole transport materials, respectively, and the rest was the same as in example 1. The test results are shown in Table 1.
Comparative examples of application
HT-28 was used as a hole transporting material, and the rest was the same as in application example 1, and the test results are shown in Table 1.
TABLE 1 organic electroluminescent device Performance results
Figure BDA0002508406240000191
From the data in the table 1, the novel organic material prepared by the invention is used for hole transport materials of organic electroluminescent devices, can effectively reduce the voltage at take off and landing, improve the current efficiency, prolong the service life of the devices, and is a hole transport material with good performance.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.

Claims (4)

1. An organic luminescent material, characterized in that the organic luminescent material has a structure shown in the following general formula (I):
Figure QLYQS_1
wherein Ar is as described 1 Selected from phenyl;
ar as described 2 Selected from any one of the following substituted or unsubstituted: biphenyl, dibenzothienyl, 9-dimethylfluorenyl;
R 1 -R 4 independently of each other selected from hydrogen;
l is selected from a bond;
x is selected from S, NR 7 The method comprises the steps of carrying out a first treatment on the surface of the Y is selected from O, S, CR 5 R 6 、NR 7 ；
R 5 、R 6 Independently selected from C 1 -C 10 An alkyl group; r is R 7 Selected from unsubstituted C 6 An aryl group;
a is selected from formula (II);
Z 1 -Z 8 selected from CR or N, R is selected from hydrogen.
2. An organic luminescent material as claimed in claim 1, wherein the organic luminescent material is selected from any one of the following compounds:
Figure QLYQS_2
/>
Figure QLYQS_3
3. an organic electroluminescent device, characterized in that it comprises the organic luminescent material according to any one of claims 1-2.
4. An organic electroluminescent device as claimed in claim 3, characterized in that the organic luminescent material is used as a hole transport material for the organic electroluminescent device.
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