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P-type doped material based on triaryl boron-nitrogen skeleton and preparation method and application thereof

A technology of triaryl boron nitrogen and doping materials, which is applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, compounds containing elements of Group 3/13 of the periodic table, etc., and can solve the shortage of high-efficiency P-type dopant materials , low luminous efficiency, fast aging speed and other problems, to achieve the effect of enhancing hole injection ability, improving luminous efficiency, and improving performance

Pending Publication Date: 2022-05-27
广东粤港澳大湾区黄埔材料研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the problems of low electroluminescent efficiency and fast aging speed of existing organic electroluminescent devices, and the lack of high-efficiency P-type dopant materials, the present invention provides a P-type dopant based on a triaryl boron-nitrogen skeleton. miscellaneous materials

Method used

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  • P-type doped material based on triaryl boron-nitrogen skeleton and preparation method and application thereof
  • P-type doped material based on triaryl boron-nitrogen skeleton and preparation method and application thereof
  • P-type doped material based on triaryl boron-nitrogen skeleton and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Preparation of compound 2

[0140] The chemical synthesis reaction scheme is as follows:

[0141]

[0142] Synthesis of Intermediate S1: A mixture of ethyl orthoformate (22.20 g, 150 mmol), yttrium trifluoromethanesulfonate (1.30 g, 2.5 mmol) and 100 mL of dimethyl sulfoxide was heated to 60 °C in batches and (about 0.50g each time, added within 10min) add 3,6-diamino-2,5-dibromo-1,4-hydroquinone (14.90g, 50mmol), stir overnight at 60°C, then cool to room temperature And dilute with water. The resulting precipitate was collected by filtration and washed with distilled water and cold ethanol, yield 75%. Molecular formula C 8 h 2 Br 2 N 2 O 2 , ESI(H + ): 316.8566.

[0143] Synthesis of Intermediate 2-1: Intermediate S1 (6.36g, 20mmol), p-fluorophenylboronic acid (3.08g, 22mmol), 300mL toluene and 80mL water mixture, add catalyst tetrakis (triphenylphosphine) palladium (0.12g , 0.1 mmol) and potassium carbonate (4.16 g, 30 mmol). The system was heated to ref...

Embodiment 2

[0151] Preparation of compound 12

[0152] The chemical synthesis reaction scheme is as follows:

[0153]

[0154] Synthesis of Intermediate 12-1: According to the synthesis of Intermediate 2-1, an equimolar amount of 2,4,6-trifluorophenylboronic acid was substituted for p-fluorophenylboronic acid, and the yield was 70%. Molecular formula C 14 H 4 BrF 3 N 2 O 2 , ESI(H + ): 368.9482.

[0155] Synthesis of Intermediate 12-2: According to the synthesis of Intermediate 2-2, intermediate 2-1 was replaced with an equimolar amount of Intermediate 12-1, and the yield was 82%. Molecular formula C 14 H 6 BF 3 N 2 O 4 , ESI(H + ): 335.0449.

[0156] Synthesis of Intermediate 12-3: According to the synthesis of Intermediate 2-4, intermediate 2-2 was replaced with an equimolar amount of Intermediate 12-2, and the yield was 68%. Molecular formula C 44 H 18 ClF 7 N 4 O 2 , MALDI-TOF (m / z): 802.23.

[0157] Synthesis of intermediate 12-4: According to the synthesis of...

Embodiment 3

[0161] Preparation of Compound 13

[0162] The chemical synthesis reaction scheme is as follows:

[0163]

[0164] Synthesis of Intermediate 13-1: According to the synthesis of Intermediate 2-1, an equimolar amount of 3,4,5-trifluorophenylboronic acid was substituted for p-fluorophenylboronic acid, and the yield was 68%. Molecular formula C 14 H 4 BrF 3 N 2 O 2 , ESI(H + ): 368.9484.

[0165] Synthesis of Intermediate 13-2: According to the synthesis of Intermediate 2-2, intermediate 2-1 was replaced with an equimolar amount of Intermediate 13-1, and the yield was 84%. Molecular formula C 14 H 6 BF 3 N 2 O 4 , ESI(H + ): 335.0452.

[0166] Synthesis of Intermediate 13-3: According to the synthesis of Intermediate 2-4, intermediate 2-2 was replaced with an equimolar amount of Intermediate 13-2, and the yield was 70%. Molecular formula C 44 H 18 ClF 7 N 4 O 2 , MALDI-TOF (m / z): 802.16.

[0167] Synthesis of Intermediate 13-4: According to the synthesis of...

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Abstract

The invention discloses a P-type doped material based on a triaryl boron-nitrogen skeleton and a preparation method and application thereof. According to the P-type doped material based on the triaryl boron-nitrogen skeleton, the triaryl boron-nitrogen resonance skeleton is taken as a core, different groups with strong electron-withdrawing capability are grafted on the periphery, the reduction potential of the material is enhanced, the LUMO energy level is reduced, the material has relatively good thermal stability and relatively strong reduction potential, and a hole transport layer can be efficiently assisted in hole injection. The preparation method disclosed by the invention can be used for preparing the P-type doped material based on the triaryl boron-nitrogen skeleton on a large scale, and is beneficial to large-scale application of the P-type doped material based on the triaryl boron-nitrogen skeleton. The P-type doping material based on the triaryl boron-nitrogen skeleton can be applied to the organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is effectively improved, the driving voltage of the organic electroluminescent device is reduced, and the performance of the organic electroluminescent device is improved.

Description

technical field [0001] The invention belongs to the field of organic semiconductor optoelectronic materials, and in particular relates to a P-type doped material based on a triaryl boron nitrogen skeleton, a preparation method and application thereof. Background technique [0002] In recent years, with the great application prospects in the fields of full-color display and solid-state white lighting, organic electroluminescent technology has received extensive research and attention in both scientific research circles and industrial circles. Compared with traditional technologies, organic light-emitting diodes (OLEDs) have many advantages such as self-luminescence, high resolution, wide viewing angle, rollability, and low energy consumption. [0003] Currently, organic electroluminescence display devices may be composed of a multilayer structure of three or more layers. In addition to the negative and positive electrodes containing metal, it also includes the organic layer ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02H01L51/50H01L51/54
CPCC07F5/027H10K85/654H10K85/657H10K85/322H10K50/11H10K2101/40H10K50/155H10K50/17Y02E10/549
Inventor 王淑萌于涵博曾天龙孟圣斐陈锴彬
Owner 广东粤港澳大湾区黄埔材料研究院
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