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CN114044778B - Tris (1,2-phenyl) diamine derivative organic photoelectric material and its use - Google Patents

Tris (1,2-phenyl) diamine derivative organic photoelectric material and its use Download PDF

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CN114044778B
CN114044778B CN202111403767.5A CN202111403767A CN114044778B CN 114044778 B CN114044778 B CN 114044778B CN 202111403767 A CN202111403767 A CN 202111403767A CN 114044778 B CN114044778 B CN 114044778B
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孙军
袁江波
胡宗学
田密
杨丹丹
何海晓
刘凯鹏
李江楠
张宏科
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Xi'an Manareco New Materials Co ltd
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Abstract

The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a tri (1,2-phenyl) diamine derivative, which has a structural general formula shown in formula (I). Wherein, the substituent L is a single bond or aryl, and the substituent A is an electron-withdrawing group; the electron-withdrawing group is selected from any one of substituted or unsubstituted triazinyl, pyrimidinyl, pyridyl, pyrazinyl, spirobifluorenyl, phosphoxy, sulfoxyl, boron-containing ligand, imidazolyl, buprenorphine Luo Linji. The compound taking the tri (1,2-phenyl) diamine as the donor has a donor-acceptor structure, has a small delta Est energy value, a proper HOMO/LUMO value and a high triplet state energy value, and can be used for preparing a high-performance organic EL element.
Figure DDA0003372003830000011

Description

Tris (1,2-phenyl) diamine derivative organic photoelectric material and its use
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a plurality of tri (1,2-phenyl) diamine derivatives and application thereof in organic electroluminescent materials or elements.
Background
Organic electroluminescence is a new type of optoelectronic information technology. As a self-luminous electronic component, the Light-emitting mechanism of an Organic Light Emitting Diode (OLED) display and lighting component is to directly convert electrical energy into Light energy by means of an Organic semiconductor functional material under the action of a dc electric field. The emission color of the OLED can be red, green, blue, yellow alone or combined white. The OLED light-emitting display technology has the biggest characteristics of ultra-thin property, high response speed, ultra-light weight, surface light-emitting property and flexible display, can be used for manufacturing monochromatic or full-color displays, and can also be used for manufacturing illumination, display products or liquid crystal displays.
Organic electroluminescent devices (organic EL devices) are classified into fluorescent type and phosphorescent type according to the principle of light emission. A voltage is applied to the organic EL element, and holes from the anode and electrons from the cathode are injected, which are recombined in the light-emitting layer to form excitons. According to the electron spin statistical method, singlet excitons and triplet excitons are generated in a ratio of 25. The fluorescent organic electroluminescent material uses singlet excitons to emit light, and thus its internal quantum efficiency is only 25%. The phosphorescence organic electroluminescent material is composed of heavy metal elements, and can simultaneously utilize singlet state energy and triplet state energy through gap crossing, and the internal quantum efficiency can reach 100%.
A Thermally Active Delayed Fluorescence (TADF) material is a third generation organic light emitting material developed after organic fluorescent materials and organic phosphorescent materials. The material generally has smaller singlet-triplet energy level difference (delta Est), triplet excitons can be converted into singlet excitons through reverse gap crossing to emit light, the singlet excitons and the triplet excitons formed under electric excitation can be fully utilized, the internal quantum efficiency of the device can reach 100 percent, meanwhile, the material has controllable structure and stable property, is low in price, does not need noble metals such as iridium, platinum and the like, and has wide application prospect in the field of OLEDs. The research result shows that: the TADF material can be used not only as a luminescent material (emitter) in a luminescent layer, but also as a host material or an auxiliary host material in the luminescent layer to sensitize the emitter, which is helpful for improving the efficiency of the conventional device, improving the color purity of the device, and increasing the working life of the device, and is an organic electroluminescent functional material with a wide application prospect. The TADF material is generally formed by connecting electron donating groups and electron withdrawing groups through a pi bond in structure, but the electron donating groups which can be utilized at present are not many in types, so that the design of a novel electron donating group to develop a novel TADF material is very important, and the development of a donor-acceptor type bipolar material as a luminescent layer main body material can be used for more effectively compounding holes and electrons in a luminescent layer, so that the photoelectric properties such as the efficiency of a device are improved.
The tri (1,2-phenyl) diamine can effectively inhibit pi-pi accumulation due to the specific rigidity and spatial structure, reduce quenching and molecular vibration caused by molecular aggregation, and has more stable molecular structure. The nitrogen atoms in the molecules can effectively transfer holes and are further connected with electron-withdrawing groups to construct donor-acceptor type bipolar materials, and the materials have proper molecular front linear orbital energy level and higher triplet state energy (T1), can be used as phosphorescent main materials and TADF luminescent materials, and have wide application market prospects.
Disclosure of Invention
The invention aims to provide a series of tri (1,2-phenyl) diamine derivatives which are applied to an organic electroluminescent device as a luminescent layer material and can remarkably improve the device performance of the organic electroluminescent device.
The tri (1,2-phenyl) diamine derivative has a structural general formula shown in a formula (I):
Figure BDA0003372003810000021
wherein, the substituent L is a single bond or aryl, and the substituent A is an electron-withdrawing group;
the electron withdrawing group is selected from any one of substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phosphoxy, substituted or unsubstituted sulfoxido, substituted or unsubstituted boron-containing ligand, substituted or unsubstituted imidazolyl, substituted or unsubstituted lophine Luo Linji.
Further preferably, the tri (1,2-phenyl) diamine derivative has any of the substituents of triazinyl, pyrimidinyl, pyridyl, pyrazinyl, spirobifluorenyl, phosphorus oxy, sulfoxide, boron-containing ligand, imidazolyl, phenanthroline Luo Linji being alkyl, cyano, trifluoromethyl, aryl, heteroaryl.
Further preferably, the tris (1,2-phenyl) diamine derivative in which the substituent L is L 1 -L 4 Any one of:
Figure BDA0003372003810000031
further preferably, the substituent a is any one of A1 to a 20:
Figure BDA0003372003810000032
the invention further provides a specific structure of the tri (1,2-phenyl) diamine derivative, which is any one of compounds 1-55:
Figure BDA0003372003810000041
Figure BDA0003372003810000051
Figure BDA0003372003810000061
Figure BDA0003372003810000071
the invention also provides an organic electroluminescent material which contains the tri (1,2-phenyl) diamine derivative.
Further, the present invention provides an organic electroluminescent element made of the organic electroluminescent material according to the present invention.
In a preferred embodiment, the organic electroluminescent element comprises an anode and a cathode, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer containing the organic electroluminescent material.
In a preferred embodiment, the light-emitting layer of the organic electroluminescent element is any one of a phosphorescent device, a fluorescent device, and a thermally activated delayed fluorescent device.
The invention also provides the application of the organic electroluminescent material or the organic electroluminescent element in organic electroluminescent display.
Compared with the prior art, the invention has the following beneficial effects or advantages.
The invention provides a plurality of tri (1,2-phenyl) diamine derivatives and provides a synthetic method of the tri (1,2-phenyl) diamine derivative. The compound taking the tri (1,2-phenyl) diamine as the donor has a donor-acceptor structure, has a small delta Est energy value, a proper HOMO/LUMO value and a high triplet state energy value, and can be used for preparing a high-performance organic EL element. Meanwhile, the tri (1,2-phenyl) diamine derivative has higher thermal stability, can remarkably improve the luminous stability of a light-emitting device, can be used as a main material of a luminous layer or a thermal activity delayed fluorescence luminous material, and has wide application prospects in OLED luminous devices and display devices.
Drawings
The present invention will now be described in detail by reference to the embodiments shown in the drawings, which are provided for illustration only and are not to be construed as limiting the invention in any way.
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention.
Description of the reference numerals: 1. the light-emitting diode comprises a substrate, 2, an anode layer, 3, a hole injection layer, 4, a first hole transport layer, 5, a second hole transport layer, 6, a light-emitting layer, 7, a hole blocking layer, 8, an electron transport layer, 9, an electron injection layer, 10 and a cathode layer.
Detailed Description
The following detailed description of the embodiments of the present invention refers to the accompanying drawings. It is to be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention, which is defined by the appended claims, as may be amended or modified based upon the breadth to which they are applied.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1 preparation of a tris (1,2-phenyl) diamine derivative
This example provides a specific method for the synthesis of several intermediates corresponding to the above compounds, and illustrates the preparation of several tris (1,2-phenyl) diamine derivatives.
(1) Synthesis of intermediates 1 to 3
Figure BDA0003372003810000091
300g of intermediate 1-1, 1330.0g of intermediate 1-2, 929.6g of sodium tert-butoxide and 8L of toluene are sequentially added into a three-neck flask, nitrogen is introduced to replace air in a reaction flask, 38.2g of cuprous iodide is added, the reaction solution is heated to 110 ℃ for reflux stirring reaction for 4 hours, TLC is used for monitoring the complete consumption of the raw material intermediate 1-1, heating is stopped after the reaction solution is cooled to room temperature, the reaction solution is washed to be neutral by water, an organic phase is dried by anhydrous sodium sulfate and purified by a silica gel column to obtain 149.8g of intermediate 1-3, and the yield is 27.8 percent.
(2) Synthesis of intermediate 1
Figure BDA0003372003810000092
140g of intermediate 1-3, 281.2g of intermediate 1-4, 144.6g of potassium acetate and 2L of toluene are sequentially added into a three-mouth bottle, nitrogen is introduced to replace the air in the reaction bottle, 10.8g of [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride is added, the reaction liquid is heated to 110 ℃ and refluxed and stirred for reaction for 6h, the heating is stopped after TLC monitors that the intermediate 1-3 is completely consumed, the reaction liquid is washed to be neutral after being cooled to the room temperature, and an organic phase is dried by anhydrous sodium sulfate and purified by a silica gel column to obtain 178.1g of intermediate 1 with the yield of 63.2%.
(3) Synthesis of Compound 1
Figure BDA0003372003810000093
10g of intermediate 1,9.0g of compound 1 to 1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, stopping heating after TLC monitors that the raw material intermediate 1 is completely consumed, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 8.6g of the compound 1 with the yield of 67.7%.
1H NMR(400MHz,CDCl3)δ8.36(d,J＝8.0Hz,4H),7.67(d,J＝7.6Hz,4H),7.50(m,6H),7.33(d,J＝7.6Hz,1H),7.23(s,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(4) Synthesis of Compound 2
Figure BDA0003372003810000101
10g of intermediate 1, 11.1g of compound 2-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 10.8g of a compound 2, wherein the yield is 73.6%.
1H NMR(400MHz,CDCl3)δ8.36(d,J＝8.0Hz,4H),7.96(d,J＝7.6Hz,2H),7.50(m,6H),7.33(d,J＝7.2Hz,1H),7.21-7.25(m,4H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(5) Synthesis of Compound 9
Figure BDA0003372003810000102
10g of intermediate 1, 13.3g of compound 9-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 12.2g of compound 9, wherein the yield is 72.9%.
1H NMR(400MHz,CDCl3)δ8.30(d,J＝8.0Hz,2H),8.23(s,1H),7.94-7.96(m,4H),7.85(d,J＝7.6Hz,2H),7.75(d,J＝7.6Hz,2H),7.55(t,J＝7.6Hz,2H),7.49(m,3H),7.41(d,J＝7.6Hz,1H),7.33(d,J＝7.2Hz,1H),7.25(d,J＝8.0Hz,2H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(6) Synthesis of Compound 17
Figure BDA0003372003810000111
10g of intermediate 1,6.9g of compound 17-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 7.8g of a compound 17 with the yield of 65.2%.
1H NMR(400MHz,CDCl3)δ8.13(d,J＝8.4Hz,1H),7.83(m,2H),7.80(d,J＝8.0Hz,2H),7.67(m,3H),7.58(t,J＝8.0Hz,1H),7.49(d,J＝7.6Hz,1H),7.33(d,J＝7.2Hz,1H),7.23(s,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(7) Synthesis of Compound 18
Figure BDA0003372003810000121
10g of intermediate 1, 10.4g of compound 18-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water are added in this order in a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 10.7g of a compound 18 with the yield of 76.3%.
1H NMR(400MHz,CDCl3)δ8.13(d,J＝8.4Hz,1H),7.96(d,J＝8.0Hz,2H),7.83(m,2H),7.80(d,J＝8.0Hz,2H),7.65(t,J＝8.0Hz,2H),7.58(t,J＝8.0Hz,1H),7.49(d,J＝7.6Hz,1H),7.33(d,J＝7.2Hz,1H),7.25(d,J＝8.0Hz,2H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(8) Synthesis of Compound 21
Figure BDA0003372003810000122
10g of intermediate 1, 11.3g of compound 21-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water are added in this order in a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by using anhydrous sodium sulfate, and purifying by using a silica gel column to obtain 11.8g of a compound 21 with the yield of 79.3%.
1H NMR(400MHz,CDCl3)δ8.18(s,1H),7.90(m,3H),7.68(d,J＝7.2Hz,1H),7.55(d,J＝7.2Hz,2H),7.45(d,J＝7.2Hz,2H),7.38(t,J＝7.2Hz,1H),7.33(d,J＝7.2Hz,1H),7.28(m,5H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(9) Synthesis of Compound 24
Figure BDA0003372003810000131
10g of intermediate 1, 10.2g of compound 24-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 8.5g of a compound 24 with the yield of 61.2%.
1H NMR(400MHz,CDCl3)δ7.97(d,J＝8.4Hz,4H),7.77(d,J＝8.4Hz,4H),7.51(m,6H),7.33(d,J＝7.2Hz,1H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(10) Synthesis of Compound 26
Figure BDA0003372003810000132
10g of intermediate 1,8.5g of compound 26-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 6.6g of a compound 26, wherein the yield is 53.7%.
1H NMR(400MHz,CDCl3)δ7.95(d,J＝8.4Hz,2H),7.80(d,J＝8.4Hz,2H),7.79(d,J＝8.4Hz,2H),7.56(d,J＝8.4Hz,2H),7.54(t,J＝7.6Hz,1H),7.33(d,J＝7.2Hz,1H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(11) Synthesis of Compound 28
Figure BDA0003372003810000141
10g of intermediate 1, 11.6g of compound 28-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water are added in this order in a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 10.8g of a compound 28 with the yield of 71.2%.
1H NMR(400MHz,CDCl3)δ7.94(d,J＝8.0Hz,2H),7.77(d,J＝8.0Hz,2H),7.33(d,J＝7.2Hz,1H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95-6.97(m,8H),2.33(s,12H),2.18(s,6H)。
(12) Synthesis of Compound 29
Figure BDA0003372003810000142
10g of intermediate 1,7.8g of compound 29-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water are added in sequence into a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 6.2g of a compound 29 with the yield of 52.9%.
1H NMR(400MHz,CDCl3)δ8.56(d,J＝7.2Hz,1H),7.81(d,J＝8.0Hz,1H),7.67(d,J＝7.2Hz,1H),7.62(t,J＝7.2Hz,1H),7.53(t,J＝7.2Hz,1H),7.48(t,J＝7.2Hz,2H),7.38(d,J＝7.2Hz,2H),7.33(d,J＝7.2Hz,1H),7.28(t,J＝7.2Hz,1H),7.23(s,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(13) Synthesis of Compound 30
Figure BDA0003372003810000151
10g of intermediate 1, 10.0g of compound 30-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 9.5g of a compound 30 with the yield of 69.1%.
1H NMR(400MHz,CDCl3)δ8.56(d,J＝7.2Hz,1H),7.96(d,J＝7.6Hz,2H),7.81(d,J＝8.0Hz,1H),7.62(t,J＝7.2Hz,1H),7.53(t,J＝7.2Hz,1H),7.48(t,J＝7.2Hz,2H),7.38(d,J＝7.2Hz,2H),7.33(d,J＝7.2Hz,1H),7.28(t,J＝7.2Hz,1H),7.25(d,J＝7.6Hz,2H),7.23(s,1H),7.21(d,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(14) Synthesis of Compound 37
Figure BDA0003372003810000152
10g of intermediate 1,9.6g of compound 37-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 10.1g of a compound 37, wherein the yield is 75.6%.
1H NMR(400MHz,CDCl3)δ8.33(d,J＝7.6Hz,2H),8.71(d,J＝8.4Hz,2H),8.20(d,J＝8.4Hz,2H),7.78(d,J＝7.6Hz,1H),7.62(s,1H),7.55(t,J＝7.6Hz,2H),7.49(d,J＝7.6Hz,1H),7.33(d,J＝7.2Hz,1H),7.29(d,J＝8.4Hz,2H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(15) Synthesis of Compound 45
Figure BDA0003372003810000161
10g of intermediate 1,8.2g of compound 45-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water were sequentially added to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 8.2g of a compound 45 with the yield of 68.5%.
1H NMR(400MHz,CDCl3)δ8.03(d,J＝8.0Hz,2H),7.95(d,J＝7.6Hz,1H),7.80(d,J＝8.4Hz,2H),7.76(s,1H),7.67(t,J＝8.4Hz,2H),7.59(d,J＝7.6Hz,1H),7.32(d,J＝8.0Hz,2H),7.37(d,J＝7.6Hz,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(16) Synthesis of Compound 53
Figure BDA0003372003810000162
10g of intermediate 1, 10.7g of compound 53-1,7.2g of potassium carbonate, 200ml of toluene, 40ml of ethanol and 20ml of water are added in this order in a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.3g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for 6h, monitoring by TLC that the raw material intermediate 1 is completely consumed, stopping heating, cooling to room temperature, washing the reaction solution to be neutral, drying an organic phase by anhydrous sodium sulfate, and purifying by a silica gel column to obtain 8.1g of the compound 53, wherein the yield is 56.8%.
1H NMR(400MHz,CDCl3)δ8.98(d,J＝8.4Hz,2H),8.11(d,J＝8.4Hz,2H),7.68(t,J＝8.4Hz,2H),7.67(d,J＝7.6Hz,1H),7.62(m,3H),7.48(t,J＝7.2Hz,2H),7.38(d,J＝7.2Hz,2H),7.33(d,J＝7.6Hz,1H),7.23(s,1H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
Example 2 performance verification of tris (1,2-phenyl) diamine derivatives
The T1 level, HOMO level and LUMO level were measured for some of the compounds provided in example 1 and the conventional materials, respectively, and the results are shown in table 1. The triplet energy (T1) of the highest molecular occupied orbital (HOMO) and the lowest molecular unoccupied orbital (LUMO) is obtained by simulation calculation by using B3LYP hybridization functional with the basis set of 6-31g (d, p).
TABLE 1 Performance testing of tris (1,2-phenyl) diamine derivatives and existing materials
Figure BDA0003372003810000171
From table 1, the tris (1,2-phenyl) diamine derivatives of the present invention have higher triplet energy and more suitable HOMO/LUMO, which are favorable for carrier transport and energy transfer in OLED devices, and these compounds can be used as phosphorescent host materials and also as TADF light emitting materials. The organic electroluminescent device may be, without particular limitation, a phosphorescent device or a Thermally Active Delayed Fluorescence (TADF) material device. Therefore, after the compound taking the tri (1,2-phenyl) diamine as the donor is applied to the light-emitting layer of the OLED device, the light-emitting efficiency, the service life and other properties of the device can be effectively improved.
Example 3
The invention provides a part of tri (1,2-phenyl) diamine derivative as an example, which is applied to an organic electroluminescent device as a luminescent layer material (host material and/or doped dye) to verify the excellent effect.
The excellent effect of the OLED materials of the present invention in the application of the devices is detailed by the device properties of device examples 1-14 and comparative examples 1-2. The manufacturing processes of the device examples 1 to 14 of the invention and the comparative examples 1 to 2 are completely the same, and the same glass substrate and electrode material are adopted, the film thickness of the electrode material is also kept consistent, except that the material of the luminescent layer is adjusted, which is specifically as follows.
Device example 1
The present embodiment provides an organic electroluminescent device, which has a structure as shown in fig. 1, and includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are sequentially stacked.
Wherein, the anode layer 2 is made of Indium Tin Oxide (ITO) with high common function, the hole injection layer 3 is made of HAT-CN with the thickness of 5nm; NPB is selected as the material of the first hole transport layer 4, and the thickness is 60nm; TCTA is selected as the material of the second hole transport layer 5, and the thickness is 15nm; the luminescent layer 6 used GD01 as a luminescent material and compound 2 as a host material, with a doping amount ratio of 6% and a thickness of 30nm; HB1 is selected as the material of the hole blocking layer 7, and the thickness is 10nm; the material of the electron transport layer 8 is ET-1, and the thickness is 35nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2nm; the cathode layer is made of Al and has a thickness of 120nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0003372003810000181
Figure BDA0003372003810000191
the organic electroluminescent device is prepared by the following specific steps:
1) Cleaning an ITO anode on a transparent glass substrate, respectively carrying out ultrasonic cleaning for 20 minutes by using deionized water, acetone and ethanol, and then carrying out Plasma (Plasma) treatment for 5 minutes in an oxygen atmosphere;
2) Evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer is used as a hole injection layer;
3) Evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is used as a first hole transport layer;
4) Evaporating a hole transport material TCTA on the first hole transport layer NPB in a vacuum evaporation mode, wherein the thickness of the TCTA is 15nm, and the TCTA serves as a second hole transport layer;
5) Co-evaporating a light-emitting layer on the second hole transport layer by a vacuum evaporation method, wherein a compound 2 is used as a host material, GD01 is used as a light-emitting material, the doping amount ratio is 6%, and the thickness is 30nm;
6) A hole blocking material HB1 is evaporated on the light-emitting layer in a vacuum evaporation mode, the thickness of the hole blocking material HB1 is 10nm, and the layer serves as a hole blocking layer;
7) Evaporating an electron transport material ET-1 on the hole blocking layer in a vacuum evaporation mode, wherein the thickness of the electron transport material ET-1 is 35nm, and the electron transport material ET-1 serves as an electron transport layer;
8) Evaporating an electron injection material Liq with the thickness of 2nm on the electron transmission layer in a vacuum evaporation way, wherein the layer is used as an electron injection layer;
9) On the electron injection layer, a cathode Al was deposited by vacuum deposition to a thickness of 120nm, and the layer was used as a cathode conductive electrode.
Device example 2
Same as device example 1, except that: compound 9 was used as the host instead of compound 2.
Device example 3
Same as device example 1, except that: compound 17 was used as the host instead of compound 2.
Device example 4
Same as device example 1, except that: compound 18 was used as the host instead of compound 2.
Device example 5
Same as device example 1, except that: compound 21 was used as the host instead of compound 2.
Device example 6
Same as device example 1, except that: compound 24 was used as the host instead of compound 2.
Device example 7
Same as device example 1, except that: compound 26 was used as the host instead of compound 2.
Device example 8
Same as device example 1, except that: compound 29 was used as the host instead of compound 2.
Device example 9
Same as device example 1, except that: compound 30 was used as the host instead of compound 2.
Device example 10
Same as device example 1, except that: compound 53 was used as the host instead of compound 2.
Device example 11
Same as device example 1, except that: the compound BH1 is used as a main body to replace the compound 2, and the compound 1 is used as a luminescent material to replace GD01.
Device example 12
Same as device example 1, except that: compound BH1 was used as a host instead of compound 2, and compound 28 was used as a light-emitting material instead of GD01.
Device example 13
Same as device example 1, except that: the compound BH1 is used as a main body to replace the compound 2, and the compound 37 is used as a luminescent material to replace GD01.
Device example 14
Same as device example 1, except that: compound BH1 was used as a host instead of compound 2, and compound 45 was used as a light-emitting material instead of GD01.
Comparative example 1
Same as device example 1, except that: CPB was used as the host material instead of compound 2.
Comparative example 2
Same as device example 11, except that: BD01 as the doping material instead of compound 1.
The composition of the various devices prepared in inventive device examples 1 to 14 and comparative examples 1 to 2 is shown in Table 2.
TABLE 2 comparison table of components of each organic electroluminescent device
Figure BDA0003372003810000211
Figure BDA0003372003810000221
Groups of organic electroluminescent devices were connected to the cathode and anode using a known drive circuit and the voltage-efficiency-current density relationship of the OLED devices was tested by standard methods using a Keithley2400 power supply in combination with a PR670 photometer. The service life of the device is tested by a constant current method under the condition that the constant current density is 10mA/cm 2 The time for the test brightness to decay to 95% of the initial brightness is the device LT 95 And (4) service life. The test results are shown in table 3:
TABLE 3 Performance results of organic electroluminescent devices of the respective device examples
Figure BDA0003372003810000222
As can be seen from Table 3, the compounds provided by the present invention are excellent in performance when applied to OLED emitters as host materials and light-emitting materials for light-emitting layers. Compared with the CPB of the comparative example 1, the compound 21 in the device example 5 serving as the phosphorescent main body material has the advantages that the luminous efficiency and the service life are remarkably improved, the luminous efficiency is improved by about 16.7%, and the service life is improved by 36.2%; as compared with BD01 in comparative example 2, the compound 1 as a light-emitting material in device example 11 has an improved luminous efficiency of about 18.2%, an improved lifetime of 48.8%, and excellent color coordinates. Compared with the OLED light-emitting device applied by the existing material, the compound provided by the invention has good photoelectric properties such as light-emitting efficiency, service life and the like, and has great application value and commercial prospect in the application of the OLED device, and good industrial prospect.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, without departing from the principle of the present invention, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall into the protection scope of the present invention.

Claims (9)

1. The tri (1,2-phenyl) diamine derivative has a structural general formula shown in formula (I):
Figure FDA0004070117140000011
wherein, the substituent L is a single bond or aryl, and the substituent A is an electron-withdrawing group; with the proviso that A-L-is not
Figure FDA0004070117140000012
The electron withdrawing group is selected from any one of substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phosphoxy, substituted or unsubstituted sulfoxido, substituted or unsubstituted boron-containing ligand, substituted or unsubstituted imidazolyl, substituted or unsubstituted phenanthroline Luo Linji;
the substituent of the triazinyl, pyrimidinyl, pyridyl, pyrazinyl, spirobifluorenyl, phosphorus oxy, sulfoxide, boron-containing ligand, imidazolyl, and phenanthroline Luo Linji is any one of alkyl, cyano, trifluoromethyl, aryl and heteroaryl.
2. The tris (1,2-phenyl) diamine derivative of claim 1, wherein the substituent L is L 1 -L 4 Any one of:
Figure FDA0004070117140000013
3. the tris (1,2-phenyl) diamine derivative of claim 1, wherein the substituent a is any of A1-a 20:
Figure FDA0004070117140000014
Figure FDA0004070117140000021
4. the tris (1,2-phenyl) diamine derivative of claim 1 which is any of compounds 1-55:
Figure FDA0004070117140000022
Figure FDA0004070117140000031
Figure FDA0004070117140000041
Figure FDA0004070117140000051
Figure FDA0004070117140000061
5. an organic electroluminescent material comprising the tris (1,2-phenyl) diamine derivative as claimed in any one of claims 1 to 4.
6. An organic electroluminescent element made of the organic electroluminescent material as claimed in claim 5.
7. The organic electroluminescent element according to claim 6, comprising an anode and a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer comprises a light-emitting layer containing the organic electroluminescent material.
8. The organic electroluminescent element according to claim 7, wherein the light-emitting layer is any one of a phosphorescent device, a fluorescent device, and a thermally activated delayed fluorescent device.
9. Use of the organic electroluminescent material according to claim 5 or the organic electroluminescent element according to claim 6 in an organic electroluminescent display.
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