CN114644637A - 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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CN114644637A
CN114644637A CN202210308192.7A CN202210308192A CN114644637A CN 114644637 A CN114644637 A CN 114644637A CN 202210308192 A CN202210308192 A CN 202210308192A CN 114644637 A CN114644637 A CN 114644637A
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phenyl
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蔡亮
张珍
孙军
张宏科
刘凯鹏
田密
何海晓
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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 a formula (I); wherein, the substituent L is a single bond or aryl, and the substituent D is an electron donating group; the electron-donating group is selected from substituted or unsubstituted amine group, carbazolyl, phenoxazinyl, acridinyl, 10H spiro [ acridine-9, 9' -fluorene]10H spiro [ acridine-9, 9' -xanthene]Any one of a 5-phenyl-5, 10-dihydrophenazinyl group and a 10H-phenothiazinyl group. The compound using tri (1, 2-phenyl) diamine as a donor has an electron donating propertyThe organic EL material has proper HOMO/LUMO value and higher triplet state energy value, and can be used for preparing high-performance organic EL elements.
Figure DDA0003566612730000011

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 derivative organic photoelectric materials 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 Emission Diode (OLED) display and lighting component is to directly convert electric energy into Light energy by means of an Organic semiconductor functional material under the action of a direct current electric field. The color of the emitted light of the OLED can be red, green, blue, yellow alone or in combination with white light. 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 backlight sources of liquid crystal displays.
Organic electroluminescent devices (organic EL devices) are classified into fluorescent type and phosphorescent type according to the principle of light emission. When a voltage is applied to the organic EL element, holes from the anode and electrons from the cathode are injected, and these holes are recombined in the light-emitting layer to form excitons, which undergo radiative transition to produce a light-emitting phenomenon. According to the electron spin statistics, singlet excitons and triplet excitons are generated at a ratio of 25: 75. The fluorescent organic electroluminescent material uses singlet excitons to emit light, so that the internal quantum efficiency thereof can only reach 25%. The phosphorescent organic electroluminescent material is composed of heavy metal elements, and can simultaneously utilize singlet state energy and triplet state energy through intersystem 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 intersystem 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 results of the current study show that: the TADF material is generally formed by connecting an electron donating group and an electron withdrawing group through a pi bond, an exciton is formed by intramolecular charge transmission, the service life of the material cannot meet the application requirement, particularly, the TADF material is mainly made of the traditional fluorescent material in the blue light industrialization aspect, and how to design and develop the high-performance blue light fluorescent material is always a hot spot in the industry.
Due to the specific rigidity and spatial three-dimensional structure of the tri (1, 2-phenyl) diamine, pi-pi accumulation can be effectively inhibited, quenching and molecular vibration caused by molecular aggregation are reduced, and the molecular structure is more stable. The nitrogen atom in the molecule has the electron-withdrawing characteristic different from C, Si and P atoms, the tri (1, 2-phenyl) diamine parent nucleus structure has an amino property due to the existence of two N atoms, a hole can be effectively transferred under an excited state, and the tri (1, 2-phenyl) diamine parent nucleus structure is further connected with an electron-donating group to construct a material with a hole transmission property, the material has a proper molecular front linear orbit energy level and higher triplet state energy (T1), can be used as a hole transmission material and a luminescent material, and has wide application market prospect.
Disclosure of Invention
The invention aims to provide a series of tri (1, 2-phenyl) diamine derivatives, wherein electron-donating groups such as amino and carbazolyl are further introduced into a tri (1, 2-phenyl) diamine parent nucleus, and the constructed compounds have typical electron-donating characteristics. The tri (1, 2-phenyl) diamine derivative provided by the invention is applied to an organic electroluminescent device as a hole transport material or a luminescent layer material, and can remarkably improve the device performance of the organic electroluminescent device.
In one aspect, the present invention relates to a tris (1, 2-phenyl) diamine derivative having the general structural formula shown in formula (I):
Figure BDA0003566612710000031
wherein, the substituent L is a single bond or aryl, and the substituent D is an electron-donating group;
the electron donating group is any one selected from the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted 10H spiro [ acridine-9, 9 '-fluorene ] group, a substituted or unsubstituted 10H spiro [ acridine-9, 9' -xanthene ] group, a substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, and a substituted or unsubstituted 10H-phenothiazinyl group.
Further, in the tris (1, 2-phenyl) diamine derivative provided by the present invention, the substituent L is L1～L4Any one of:
Figure BDA0003566612710000032
further, in the tris (1, 2-phenyl) diamine derivative provided by the present invention, the substituent D is any one of D1 to D7:
Figure BDA0003566612710000041
wherein Ar is1Or Ar2Is any one of aryl and heteroaryl; r1Or R2Is any one of aryl, alkyl and heteroaryl; x is oxygen atom, sulfur atom, C-m1m2Or N-m3M is one of1Or m2Is any one of hydrogen atom, methyl, phenyl and biphenyl, and m is3Is phenyl; y is any one of a carbon atom, a nitrogen atom and an oxygen atom.
Further preferably, in the tris (1, 2-phenyl) diamine derivative provided by the present invention, Ar is1Or Ar2Is any one of phenyl, biphenyl, carbazolyl and furyl, and R is1Or R2Is any one of methyl, ethyl, tert-butyl, phenyl, biphenyl, carbazolyl and furyl.
Further, the invention provides a specific structure of the tri (1, 2-phenyl) diamine derivative, which is any one of compounds 1 to 50:
Figure BDA0003566612710000042
Figure BDA0003566612710000051
Figure BDA0003566612710000061
Figure BDA0003566612710000071
in another aspect, the present invention relates to an organic electroluminescent material comprising the tris (1, 2-phenyl) diamine derivative according to the present invention.
In another aspect, the present invention relates to an organic electroluminescent element made of the organic electroluminescent material according to the present invention.
In a preferred embodiment, the organic electroluminescent device 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 hole transport layer, a light-emitting layer, and an electron transport layer, and the hole transport layer or the light-emitting layer contains 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.
In another aspect, 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 derivatives. According to the invention, electron-donating groups such as amino groups and carbazolyl groups are further introduced on the basis of a tri (1, 2-phenyl) diamine parent nucleus, and the constructed compound has a typical electron-donating characteristic, has 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 with the spatial three-dimensional structure has higher thermal stability, can obviously improve the luminous stability of a light-emitting device, can be used as a hole transport material and a luminous layer material, and has wide application prospect in OLED (organic light-emitting diode) luminous devices and display devices.
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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 reference numerals: 1. the cathode layer 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, including obvious variations or modifications based thereon.
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
This example provides specific synthetic methods for specific compounds and corresponding intermediates involved in the tris (1, 2-phenyl) diamine derivatives.
(1) Synthesis of intermediate 1
Figure BDA0003566612710000091
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-necked flask, nitrogen is introduced to replace air in the reaction flask, 38.2g of cuprous iodide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the intermediate 1-1 is completely consumed, 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 then purified by a silica gel column to obtain 149.8g of intermediate 1, and the yield is 27.8%.
(2) Synthesis of intermediate 1
Figure BDA0003566612710000101
60g of intermediate 1, 120.5g of intermediate 2-1, 62.0g of potassium acetate and 1L of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace air in the reaction flask, 4.6g of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride is added, the reaction solution is heated to 110 ℃ and stirred under reflux for 6 hours, TLC monitors that the intermediate 1 is completely consumed, 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 then purified by a silica gel column to obtain 76.3g of intermediate 2, and the yield is 63.2%.
(3) Synthesis of Compound 1
Figure BDA0003566612710000102
10g of intermediate 2, 9.3g of compound 1-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, stopping heating after TLC monitors that the raw material intermediate 2 is completely consumed, 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 9.3g of a compound 1 with the yield of 71.6%.
1H NMR(400MHz,CDCl3)δ8.19(d,J＝7.2Hz,2H),7.91-7.94(m,6H),7.50(t,J＝7.2Hz,2H),7.33(d,J＝7.6Hz,1H),7.23(s,1H),7.21(m,3H),7.14(d,J＝7.6Hz,4H),6.95(d,J＝7.6Hz,4H)。
(4) Synthesis of Compound 6
Figure BDA0003566612710000111
10g of the intermediate 1, 5.5g of the intermediate 6-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace air in the reaction flask, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the intermediate 1 is completely consumed, heating is stopped after the reaction solution is cooled to room temperature, the reaction solution is washed to be neutral, the organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 9.6g of the compound 6, and the yield is 76.2%.
1H NMR(400MHz,CDCl3)δ8.19(d,J＝7.2Hz,2H),7.94(d,J＝7.2Hz,2H),7.50(d,J＝7.2Hz,2H),7.35(d,J＝7.6Hz,1H),7.28(d,J＝7.6Hz,1H),7.20(d,J＝7.2Hz,2H),7.14(d,J＝7.6Hz,4H),7.12(s,1H),6.95(d,J＝7.6Hz,4H)。
(5) Synthesis of Compound 17
Figure BDA0003566612710000112
10g of the intermediate 1, 13.9g of the intermediate 17-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace air in the reaction flask, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the raw material intermediate 1 is completely consumed, heating is stopped after the raw material intermediate 1 is completely consumed, the reaction solution is washed to be neutral after being cooled to room temperature, an organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 16.5g of the compound 17, and the yield is 81.9%.
1H NMR(400MHz,CDCl3)δ8.09(d,J＝6.4Hz,2H),8.06(d,J＝6.4Hz,2H),7.99(d,J＝6.4Hz,2H),7.63(t,J＝6.4Hz,2H),7.60(t,J＝6.4Hz,2H),7.55(m,6H),7.37(m,6H),7.14(d,J＝7.6Hz,4H),7.10(d,J＝7.6Hz,1H),6.95(d,J＝7.6Hz,4H),6.80(m,2H)。
(6) Synthesis of Compound 18
Figure BDA0003566612710000121
10g of intermediate 2, 9.3g of compound 18-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, stopping heating after TLC monitors that the raw material intermediate 2 is completely consumed, 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 10.0g of a compound 18 with the yield of 76.3%.
1H NMR(400MHz,CDCl3)δ7.55(d,J＝7.2Hz,2H),7.37(d,J＝7.2Hz,2H),7.33(d,J＝7.6Hz,1H),7.21-7.24(m,6H),7.14(d,J＝7.6Hz,4H),7.08(d,J＝7.2Hz,4H),7.00(t,J＝7.2Hz,2H),6.95(d,J＝7.6Hz,4H)。
(7) Synthesis of Compound 22
Figure BDA0003566612710000131
10g of intermediate 2, 11.9g of compound 22-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, stopping heating after TLC monitors that the raw material intermediate 2 is completely consumed, 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 10.1g of a compound 22 with the yield of 65.8%.
1H NMR(400MHz,CDCl3)δ8.22(s,1H),7.98(d,J＝7.2Hz,1H),7.54-7.56(m,4H),7.39(t,J＝7.2Hz,1H),7.37(d,J＝7.2Hz,2H),7.33(d,J＝7.6Hz,1H),7.31(t,J＝7.2Hz,1H),7.21-7.24(m,4H),7.14(d,J＝7.2Hz,4H),7.00(d,J＝7.2Hz,1H),6.97(d,J＝7.6Hz,1H),6.95(d,J＝7.2Hz,4H)。
(8) Synthesis of Compound 23
Figure BDA0003566612710000132
10g of intermediate 2, 12.6g of compound 23-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, stopping heating after TLC monitors that the raw material intermediate 2 is completely consumed, 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 10.2g of a compound 23 with the yield of 63.1%.
1H NMR(400MHz,CDCl3)δ7.90(d,J＝6.8Hz,1H),7.62(s,1H),7.55(m,3H),7.51(d,J＝7.2Hz,1H),7.38(m,3H),7.33(d,J＝7.6Hz,1H),7.28(t,J＝6.8Hz,1H),7.21-7.24(m,4H),7.14(d,J＝7.2Hz,4H),7.08(d,J＝6.8Hz,2H),7.06(d,J＝7.2Hz,1H),7.00(d,J＝6.8Hz,1H),6.95(d,J＝7.2Hz,4H),1.69(s,6H)。
(9) Synthesis of Compound 24
Figure BDA0003566612710000141
10g of intermediate 2, 14.0g of compound 24-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, monitoring by TLC that the raw material intermediate 2 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 11.9g of a compound 24, wherein the yield is 68.3%.
1H NMR(400MHz,CDCl3)δ7.62(d,J＝6.8Hz,2H),7.58(d,J＝6.8Hz,1H),7.54(m,4H),7.50(d,J＝6.8Hz,2H),7.37(d,J＝6.8Hz,2H),7.33-7.35(m,5H),7.21-7.24(m,4H),7.16(t,J＝7.2Hz,1H),7.14(d,J＝7.2Hz,4H),7.08(d,J＝6.8Hz,2H),7.00(t,J＝6.8Hz,1H),6.95(d,J＝7.2Hz,4H)。
(10) Synthesis of Compound 28
Figure BDA0003566612710000151
10g of the intermediate 1, 17.2g of the intermediate 28-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace air in the reaction flask, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the intermediate 1 is completely consumed, heating is stopped after the reaction solution is cooled to room temperature, the reaction solution is washed to be neutral, the organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 12.3g of the compound 28, and the yield is 52.9%.
1H NMR(400MHz,CDCl3)δ7.89(d,J＝6.8Hz,3H),7.62(s,2H),7.51(m,4H),7.45(d,J＝6.8Hz,2H),7.38(t,J＝6.8Hz,2H),7.26-7.28(m,6H),7.14(d,J＝7.2Hz,4H),7.10(d,J＝7.2Hz,4H),7.06(d,J＝6.8Hz,2H),6.95(d,J＝7.2Hz,4H),6.80(m,2H),1.69(s,6H)。
(11) Synthesis of Compound 29
Figure BDA0003566612710000152
10g of the intermediate 1, 9.4g of the intermediate 29-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace air in the reaction flask, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the intermediate 1 is completely consumed, heating is stopped after the reaction solution is cooled to room temperature, the reaction solution is washed to be neutral, the organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 13.5g of the compound 29, and the yield is 83.7%.
1H NMR(400MHz,CDCl3)δ7.90(d,J＝6.8Hz,1H),7.62(s,1H),7.55(d,J＝6.8Hz,1H),7.51(d,J＝6.8Hz,1H),7.38(t,J＝6.8Hz,1H),7.28(t,J＝6.8Hz,1H),7.24(t,J＝6.8Hz,2H),7.14(d,J＝7.2Hz,4H),7.10(d,J＝7.2Hz,1H),7.08(d,J＝6.8Hz,2H),7.06(d,J＝6.8Hz,1H),7.00(d,J＝6.8Hz,1H),6.95(d,J＝7.2Hz,4H),6.80(m,2H),1.69(s,6H)。
(12) Synthesis of Compound 30
Figure BDA0003566612710000161
10g of the intermediate 1, 11.9g of the intermediate 30-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked bottle, nitrogen is introduced to replace air in the reaction bottle, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, TLC monitors that the intermediate 1 is completely consumed, heating is stopped after the reaction solution is cooled to room temperature, the reaction solution is washed to be neutral, the organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 14.0g of the compound 30, and the yield is 76.2%.
1H NMR(400MHz,CDCl3)δ7.90(d,J＝6.8Hz,1H),7.75(d,J＝6.4Hz,2H),7.62(s,1H),7.55(m,3H),7.51(d,J＝6.8Hz,1H),7.49(d,J＝6.4Hz,2H),7.41(t,J＝6.4Hz,1H),7.37(m,3H),7.28(t,J＝6.8Hz,1H),7.14(d,J＝7.2Hz,4H),7.10(d,J＝7.2Hz,1H),7.06(d,J＝6.8Hz,1H),6.95(d,J＝7.2Hz,4H),6.80(m,2H),1.69(s,6H)。
(13) Synthesis of Compound 33
Figure BDA0003566612710000171
10g of intermediate 1, 6.9g of intermediate 33-1, 4.3g of sodium tert-butoxide, 67mg of palladium acetate and 200mL of toluene are sequentially added into a three-neck flask, nitrogen is introduced to replace the air in the reaction flask, 2.0mL of 10% toluene solution of tri-tert-butylphosphine is added, the reaction solution is heated to 110 ℃ for reflux stirring reaction for 4 hours, TLC monitors that the intermediate 1 is completely consumed, heating is stopped after the intermediate 1 is completely consumed, the reaction solution is washed to be neutral after being cooled to room temperature, an organic phase is dried by anhydrous sodium sulfate and then purified by a silica gel column to obtain 8.8g of compound 33, and the yield is 63.7%.
1H NMR(400MHz,CDCl3)δ7.19(t,J＝7.2Hz,2H),7.17(d,J＝7.2Hz,2H),7.14(m,6H),7.10(d,J＝7.6Hz,1H),6.95(m,6H),6.80(m,2H),1.69(s,6H)。
(14) Synthesis of Compound 37
Figure BDA0003566612710000172
10g of intermediate 2, 14.0g of compound 37-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, monitoring by TLC that the raw material intermediate 2 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 11.2g of a compound 37, wherein the yield is 64.9%.
1H NMR(400MHz,CDCl3)δ7.90(d,J＝6.8Hz,2H),7.55(m,4H),7.37(m,4H),7.33(d,J＝7.6Hz,1H),7.28(t,J＝6.8Hz,2H),7.23(s,1H),7.21(d,J＝7.6Hz,1H),7.17-7.19(m,4H),7.14(m,6H),6.95(m,6H)。
(15) Synthesis of Compound 38
Figure BDA0003566612710000181
10g of intermediate 2, 10.4g of compound 38-1, 7.2g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order 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 reaction for 6 hours, stopping heating after TLC monitors that the raw material intermediate 2 is completely consumed, 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 10.0g of a compound 38 with the yield of 71.2%.
1H NMR(400MHz,CDCl3)δ7.55(d,J＝6.8Hz,2H),7.37(d,J＝6.8Hz,2H),7.33(d,J＝7.6Hz,1H),7.23(s,1H),7.17-7.21(m,5H),7.14(m,6H),6.95(m,6H),1.69(s,6H)。
(16) Synthesis of Compound 44
Figure BDA0003566612710000182
10g of intermediate 1, 9.4g of compound 44-1, 8.3g of potassium carbonate, 200mL of toluene, 40mL of ethanol, and 20mL of water were added in this order to a three-necked flask. Introducing nitrogen to replace air in a reaction bottle, adding 0.34g of tetrakis (triphenylphosphine) palladium, heating the reaction solution to 80 ℃, refluxing and stirring for reaction for 6 hours, stopping heating after TLC monitors that the intermediate 1 is completely consumed, 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 10.9g of a compound 44 with the yield of 73.5%.
1H NMR(400MHz,CDCl3)δ7.94-7.99(m,4H),7.89(s,1H),7.62(t,J＝6.8Hz,2H),7.58(t,J＝6.8Hz,1H),7.50(d,J＝6.8Hz,2H),7.33(d,J＝7.6Hz,1H),7.23(s,1H),7.21(d,J＝7.6Hz,1H),7.16(m,2H),7.14(d,J＝7.2Hz,4H),6.95(d,J＝7.2Hz,4H)。
(17) Synthesis of Compound 46
Figure BDA0003566612710000191
10g of the intermediate 1, 10.9g of the intermediate 46-1, 4.3g of sodium tert-butoxide and 200mL of toluene are sequentially added into a three-necked flask, nitrogen is introduced to replace the air in the reaction flask, 0.4g of cuprous bromide is added, the reaction solution is heated to 110 ℃, reflux and stirring are carried out for reaction for 4 hours, the heating is stopped after the TLC monitors that the intermediate 1 is completely consumed, the reaction solution is washed to be neutral after being cooled to the room temperature of 19 ℃, the organic phase is dried by anhydrous sodium sulfate and then is purified by a silica gel column to obtain 13.4g of the compound 46, and the yield is 76.2%.
1H NMR(400MHz,CDCl3)δ7.62(t,J＝6.8Hz,2H),7.58(m,3H),7.55(m,3H),7.50(m,4H),7.40(s,1H),7.35(d,J＝7.6Hz,1H),7.28(d,J＝7.6Hz,1H),7.16(t,J＝7.2Hz,2H),7.14(d,J＝7.2Hz,4H),7.12(s,1H),6.95(d,J＝7.2Hz,4H)。
Example 2
In this example, T1 energy and HOMO and LUMO energy level tests were performed on a part of the compounds according to the present invention and a conventional material, respectively.
The lowest molecular occupied orbital (HOMO) and lowest molecular unoccupied orbital (LUMO) triplet energies (T1) were data obtained from simulation calculations, and the results of the experiments are shown in table 1.
TABLE 1 Performance testing of tris (1, 2-phenyl) diamine derivatives and existing materials
Figure BDA0003566612710000201
Figure BDA0003566612710000211
As can be seen 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 hole transport materials and also as light emitting materials. The organic electroluminescent device may be, without particular limitation, a phosphorescent device, a fluorescent device, or a Thermally Activated Delayed Fluorescence (TADF) material device. Therefore, after the compound taking the tri (1, 2-phenyl) diamine as the donor is applied to an OLED device, the luminous efficiency, the service life and other properties of the device can be effectively improved.
Example 3
In this embodiment, a part of tris (1, 2-phenyl) diamine derivatives provided by the present invention is taken as an example, and is applied to an organic electroluminescent device as a light emitting material or a hole transport material to verify the excellent effects obtained by the present invention.
The excellent effect of the OLED material in the invention applied to the device is detailed by the device performances of device examples 1-15 and comparative example 1. The manufacturing processes of the devices of examples 1 to 15 of the invention are completely the same as those of comparative example 1, and the same glass substrate and electrode material are adopted, and the film thickness of the electrode material is also kept consistent, except that the luminescent layer or the second hole transport layer is adjusted 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 5 nm; NPB is selected as the material of the first hole transport layer 4, and the thickness is 60 nm; the material of the second hole transport layer 5 is HT-2, and the thickness is 15 nm; the light-emitting layer 6 used compound 1 as a light-emitting material and BH1 as a host material, and had a doping ratio of 3% and a thickness of 30 nm; HB1 is selected as the material of the hole blocking layer 7, and the thickness is 10 nm; the material of the electron transport layer 8 is ET-1, and the thickness is 35 nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2 nm; the cathode layer is made of Al and has a thickness of 100 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0003566612710000221
Figure BDA0003566612710000231
the organic electroluminescent device is prepared by the following specific steps:
1) cleaning an ITO anode on a transparent glass substrate, respectively ultrasonically cleaning the ITO anode 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 HT-2 on the first hole transport layer NPB in a vacuum evaporation mode, wherein the thickness of the hole transport material HT-2 is 15nm, and the layer serves as a second hole transport layer;
5) co-evaporating a light-emitting layer on the second hole transport layer by a vacuum evaporation mode, wherein the compound 1 is used as a light-emitting material, BH1 is used as a main body material, the doping amount ratio is 3%, and the thickness is 30 nm;
6) depositing a hole blocking material HB1 on the light-emitting layer by vacuum deposition to obtain a layer with a thickness of 10nm 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 layer is used 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 100nm, and the layer was used as a cathode conductive electrode.
Device example 2
Same as device example 1, except that: compound 22 was used as a light-emitting material in place of compound 1.
Device example 3
Same as device example 1, except that: compound 23 was used as a light-emitting material in place of compound 1.
Device example 4
Same as device example 1, except that: compound 24 was used as a light-emitting material in place of compound 1.
Device example 5
Same as device example 1, except that: compound 29 was used as the light-emitting material in place of compound 1.
Device example 6
Same as device example 1, except that: compound 30 was used as a light-emitting material in place of compound 1.
Device example 7
Same as device example 1, except that: compound 33 was used as a light-emitting material in place of compound 1.
Device example 8
Same as device example 1, except that: compound 6 was used as a hole transport layer instead of HT-2, and BD01 was used as a light emitting material instead of compound 1.
Device example 9
Same as device example 1, except that: compound 17 was used as a hole transport layer instead of HT-2, and BD01 was used as a light emitting material instead of compound 1.
Device example 10
Same as device example 1, except that: compound 18 was used as a hole transport layer instead of HT-2, and BD01 was used as a light emitting material instead of compound 1.
Device example 11
Same as device example 1, except that: compound 28 was used as a hole transport layer instead of HT-2, BD01 was used as a light emitting material instead of compound 1.
Device example 12
Same as device example 1, except that: the compound 37 is used as a hole transport layer to replace HT-2, and the BD01 is used as a light-emitting material to replace the compound 1.
Device example 13
Same as device example 1, except that: the compound 38 is used as a hole transport layer to replace HT-2, and the BD01 is used as a light-emitting material to replace the compound 1.
Device example 14
Same as device example 1, except that: the compound 44 is used as a hole transport layer to replace HT-2, and the BD01 is used as a light-emitting material to replace the compound 1.
Device example 15
Same as device example 1, except that: compound 46 was used as a hole transport layer instead of HT-2, and BD01 was used as a light emitting material instead of compound 1.
Comparative example 1
Same as device example 1, except that: BD01 was used as the luminescent material instead of compound 1.
The composition of the devices prepared in inventive device examples 1 to 15 and comparative example 1 is shown in Table 2.
TABLE 2 comparison table of components of each organic electroluminescent device
Figure BDA0003566612710000261
Figure BDA0003566612710000271
The groups of organic electroluminescent devices described in table 2 were connected to the cathode and anode using a driving circuit, and the voltage-efficiency-current density relationship of the OLED devices was tested by a standard method using a Keithley2400 power supply in combination with a PR670 photometer. The test results are shown in table 3:
TABLE 3 Performance results of organic electroluminescent devices of the respective device examples
Figure BDA0003566612710000272
Figure BDA0003566612710000281
As can be seen from table 3, the compounds provided by the present invention have excellent performance when applied to OLED light emitters as light emitting materials and second hole transport layer materials. Compared with the comparative example 1BD01, the compound 30 in the device example 6 as the luminescent material has the advantages that the luminous efficiency and the brightness are both remarkably improved, the luminous efficiency is improved by 19.3%, and the brightness at the voltage of 6V is improved by 29.2%; the compound 28 of example 11 as the second hole transport layer material showed an increase in luminous efficiency of 17.4% and an increase in luminance at 6V of 28.4% over HT-2 of comparative example 1. In conclusion, the compound of the invention is selected as a luminescent material or a hole transport material of an OLED device, compared with an OLED luminescent device applied by the existing material, the photoelectric properties of the device, such as luminous efficiency, brightness and the like, have good performances, and the compound has great application value and commercial prospect in the application of the OLED device and good industrial prospect.
As described above, the present invention can be preferably implemented, and the above-mentioned embodiments only describe the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various changes and modifications of the technical solution of the present invention made by those skilled in the art without departing from the design spirit of the present invention shall fall within the protection scope defined by the present invention.

Claims (10)

1. The tri (1, 2-phenyl) diamine derivative has a structural general formula shown in formula (I):
Figure FDA0003566612700000011
wherein, the substituent L is a single bond or aryl, and the substituent D is an electron-donating group;
the electron donating group is any one selected from the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted 10H spiro [ acridine-9, 9 '-fluorene ] group, a substituted or unsubstituted 10H spiro [ acridine-9, 9' -xanthene ] group, a substituted or unsubstituted 5-phenyl-5, 10-dihydrophenazinyl group, and a substituted or unsubstituted 10H-phenothiazinyl group.
2. The tris (1, 2-phenyl) diamine derivative according to claim 1, wherein the substituent L is L1～L4Any one of:
Figure FDA0003566612700000012
3. the tris (1, 2-phenyl) diamine derivative according to claim 1, wherein the substituent D is any one of D1 to D7:
Figure FDA0003566612700000013
Figure FDA0003566612700000021
wherein Ar is1Or Ar2Is any one of aryl and heteroaryl; r1Or R2Is any one of aryl, alkyl and heteroaryl; x is oxygen atom, sulfur atom, C-m1m2Or N-m3M is one of1Or m2Is any one of hydrogen atom, methyl, phenyl and biphenyl, and m is3Is phenyl; y is any one of carbon atom, nitrogen atom and oxygen atom.
4. The tris (1, 2-phenyl) diamine derivative according to claim 3, wherein Ar is Ar1Or Ar2Is any one of phenyl, biphenyl, carbazolyl and furyl, and R is1Or R2Is any one of methyl, ethyl, tert-butyl, phenyl, biphenyl, carbazolyl and furyl.
5. The tris (1, 2-phenyl) diamine derivative according to claim 1, which is any one of the compounds 1 to 50:
Figure FDA0003566612700000022
Figure FDA0003566612700000031
Figure FDA0003566612700000041
Figure FDA0003566612700000051
6. an organic electroluminescent material comprising the tris (1, 2-phenyl) diamine derivative according to any one of claims 1 to 5.
7. An organic electroluminescent element made of the organic electroluminescent material as claimed in claim 6.
8. The organic electroluminescent element according to claim 7, comprising an anode and a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer comprises a hole transport layer, a light-emitting layer, and an electron transport layer, and the hole transport layer or the light-emitting layer contains the organic electroluminescent material.
9. The organic electroluminescent element according to claim 8, wherein the light-emitting layer is any one of a phosphorescent device, a fluorescent device, and a thermally activated delayed fluorescent device.
10. Use of the organic electroluminescent material according to claim 6 or the organic electroluminescent element according to claim 7 in an organic electroluminescent display.
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