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Tri (1, 2-phenyl) diamine derivative organic photoelectric material and application thereof

A technology of diamine derivatives and phenyl, which is applied in the field of organic electroluminescent materials, can solve the problems that the working life of materials cannot meet the application requirements, and achieve the effects of improving luminous stability, broad application prospects, and high thermal stability

Pending Publication Date: 2022-06-21
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current research results show that: TADF materials are generally composed of electron-donating groups-electron-withdrawing groups connected through π bonds, and excitons are formed through intramolecular charge transfer. The working life of the materials cannot meet the application requirements, especially in the blue light industry. In terms of chemicalization, traditional fluorescent materials are still the mainstay. How to design and develop high-performance blue fluorescent materials has always been a hot spot in the industry.

Method used

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  • Tri (1, 2-phenyl) diamine derivative organic photoelectric material and application thereof
  • Tri (1, 2-phenyl) diamine derivative organic photoelectric material and application thereof
  • Tri (1, 2-phenyl) diamine derivative organic photoelectric material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] This example provides the specific synthesis method of the specific compound involved in the tris(1,2-phenyl)diamine derivative and the corresponding intermediate.

[0036] (1) Synthesis of Intermediate 1

[0037]

[0038] 300g of intermediate 1-1, 1330.0g of intermediate 1-2, 929.6g of sodium tert-butoxide, and 8L of toluene were successively added to the three-necked flask, and 38.2g of cuprous iodide was added after the air in the reaction flask was replaced by nitrogen. The reaction solution was heated to 110°C under reflux and stirred for 4 hours. TLC monitored the complete consumption of the raw material intermediate 1-1 and then stopped heating. After cooling to room temperature, the reaction solution was washed with water until neutral. The organic phase was dried with anhydrous sodium sulfate and purified by silica gel column. 149.8 g of intermediate 1 were obtained with a yield of 27.8%.

[0039] (2) Synthesis of Intermediate 1

[0040]

[0041]In the ...

Embodiment 2

[0103] In this example, T1 energy, HOMO and LUMO energy level tests are respectively performed on some compounds involved in the present invention and existing materials.

[0104] The triplet energies (T1) of the highest molecularly occupied orbital (HOMO) and the lowest molecularly unoccupied orbital (LUMO) are the data obtained from the simulation calculations, and the experimental results are shown in Table 1.

[0105] Table 1. Performance test of tris(1,2-phenyl)diamine derivatives and existing materials

[0106]

[0107]

[0108] 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 beneficial to carrier transport and energy in OLED devices The transfer of these compounds can be used as hole transport materials, can also be used as light-emitting materials. Without specific limitation, the above-mentioned organic electroluminescent device may be a phosphorescen...

Embodiment 3

[0110] This example takes part of the tris(1,2-phenyl)diamine derivatives provided by the present invention as an example, and applies them to organic electroluminescent devices as light-emitting materials or hole-transporting materials to verify the obtained Excellent effect.

[0111] Specifically, the excellent effect of the OLED material of the present invention applied in the device is described in detail through the device performance of Device Examples 1-15 and Comparative Example 1. Examples 1 to 15 of the device of the present invention and Comparative Example 1 have exactly the same manufacturing process, and use the same glass substrate and electrode material, and the film thickness of the electrode material is also the same, the difference is the light-emitting layer or the second hole transport layer. Adjustments have been made as follows.

[0112] Device Example 1

[0113] This embodiment provides an organic electroluminescence device, the structure of which is ...

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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 as 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 any one of substituted or unsubstituted amido, carbazolyl, phenoxazine group, acridinyl, 10H spiro [acridine-9, 9 '-fluorene] group, 10H spiro [acridine-9, 9'-xanthene] group, 5-phenyl-5, 10-dihydrophenazine group and 10H-phenothiazine group. The compound taking the tris (1, 2-phenyl) diamine as the donor provided by the invention has an electron donating characteristic, an appropriate HOMO / LUMO value and a relatively high triplet state energy value, and can be used for preparing a high-performance organic EL element.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to various tris(1,2-phenyl)diamine derivative organic optoelectronic materials and their applications in organic electroluminescent materials or components. Background technique [0002] Organic electroluminescence is a new type of optoelectronic information technology. As a self-luminous electronic component, the organic light-emitting diode (Organic Light Emission Diodes, OLED) display and lighting components have a light-emitting mechanism that directly converts electrical energy into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. OLED light emission colors can be individual red, green, blue, yellow light or a combination of white light. The biggest features of OLED light-emitting display technology are ultra-thin, fast response, ultra-light, surface-emitting and flexible ...

Claims

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Application Information

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IPC IPC(8): C07D487/08C07D519/00C09K11/06H01L51/54H01L51/50
CPCC07D487/08C07D519/00C09K11/06C09K2211/1044C09K2211/1033C09K2211/1029C09K2211/1037C09K2211/1088C09K2211/1011H10K85/622H10K85/636H10K85/633H10K85/631H10K85/615H10K85/6574H10K85/6572H10K85/657H10K50/15H10K50/11
Inventor 蔡亮张珍孙军张宏科刘凯鹏田密何海晓
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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