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Amine compound and application thereof in organic electroluminescent device

A technology of amine compounds and chemical structures, applied in the fields of electric solid-state devices, organic chemistry, luminescent materials, etc., can solve the problems of insufficient molecular stability, mobility and crystallization temperature, so as to improve the glass transition temperature and increase the stability , the effect of increasing the mobility

Pending Publication Date: 2022-05-17
上海钥熠电子科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Spiro[fluorene-9,9'-oxanthene], spiro[fluorene-9,9'-thiaxanthene] and other spirofluorene compounds have relatively good hole transport and suitable conjugation. Good thermal stability is used as a hole transport material, but when spirofluorene compound is used as a hole transport material, it is still found that the molecular stability, mobility and crystallization temperature are not good enough

Method used

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  • Amine compound and application thereof in organic electroluminescent device
  • Amine compound and application thereof in organic electroluminescent device
  • Amine compound and application thereof in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Embodiment 1: the synthesis of compound A1

[0115]

[0116] The synthetic method of M1-3:

[0117] In a 2L reaction flask, weigh M1-1 (100g, 555mmol), M1-2 (148g, 555mmol), tetrakistriphenylphosphopalladium (12.8g, 11.1mmol) and potassium carbonate (153g, 1110mmol) Add to the reaction flask, add 700mL of toluene, 150mL of ethanol and 150mL of deionized water, replace the system with nitrogen three times, heat the reaction mixture to reflux, and continue stirring for 3 hours. The reaction mixture was cooled to 50°C, allowed to stand and separated, and the upper organic phase was washed with 150 mL of deionized water; the organic phase was passed through a column (toluene:petroleum ether=1:10). The solvent was concentrated, and the rest was passed through a silica gel column (toluene:petroleum ether=1:10), and the solvent was concentrated to obtain 150 g of a solid compound. Yield: 83%.

[0118] Synthesis of M1-4

[0119] To a clean 1L reaction flask, M1-3 (100g, ...

Embodiment 2

[0126] Embodiment 2: the synthesis of compound A21:

[0127]

[0128] The synthesis method, types of auxiliary materials, equivalent ratio of raw materials and auxiliary materials, and operation method of compound A21 are exactly the same as those of A1. The difference is that the reaction raw material M2-1 replaces M1-1, M2-2 replaces M1-2 raw materials, and M2-3 replaces M1-3 raw materials were replaced, M2-4 replaced M1-4 raw materials, M2-5 replaced M1-5 raw materials, M2-6 replaced M1-6 raw materials, and A21-1 replaced A1-1 raw materials. The total yield is 19.7%. The details are as follows:

[0129] The synthetic method of M2-3:

[0130] In a 2L reaction flask, weigh M2-1 (100g, 555mmol), M2-2 (175g, 555mmol), tetrakistriphenylphosphopalladium (12.8g, 11.1mmol) and potassium carbonate (153g, 1110mmol) Add to the reaction flask, add 700mL of toluene, 150mL of ethanol and 150mL of deionized water, replace the system with nitrogen three times, heat the reaction mixtu...

Embodiment 3

[0139] Embodiment 3: the synthesis of compound A22:

[0140]

[0141] The synthesis method, types of excipients, equivalent ratio of raw and excipient materials, and operation method of compound A22 are exactly the same as those of A1, the difference is that the reaction raw material M3-1 replaces M1-1, M3-2 replaces the raw material of M1-2, and M3-3 replaces M1-3 raw materials were replaced, M3-4 replaced M1-4 raw materials, M3-5 replaced M1-5 raw materials, M3-6 replaced M1-6 raw materials, and A22-1 replaced A1-1 raw materials. The total yield is 21.1%. The M / Z of compound A22 was measured by LCMS (ESI ion source): 651.5.

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Abstract

The invention relates to the field of organic electroluminescent materials, in particular to an amine compound and application thereof in an organic electroluminescent device. The chemical structure of the amine compound is shown in the specification. The amine compound provided by the invention has extremely high stability, mobility, glass transition temperature and crystallinity resistance, and can obtain a good device effect in OLED devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an amine compound and its application in organic electroluminescent devices. Background technique [0002] OLED hole transport materials require high hole transport capacity, high glass transition temperature, strong crystallization resistance, and stable molecular structure. Especially for the hole transport material where the hole transport layer is in contact with the light-emitting layer, the requirements for molecular stability and glass transition temperature are higher. The hole transport material generally uses aromatic amine amine compounds, which can better donate electrons and have high hole mobility. Spiro[fluorene-9,9'-oxanthene], spiro[fluorene-9,9'-thiaxanthene] and other spirofluorene compounds have relatively good hole transport and suitable conjugation. Good thermal stability is used as a hole transport material, but when spirofluorene compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D405/14C07D311/96C07D335/04C07D409/04C07D409/14C09K11/06H01L51/54
CPCC07D405/04C07D405/14C07D311/96C07D335/04C07D409/04C07D409/14C09K11/06C09K2211/1088C09K2211/1092C09K2211/1029H10K85/6576H10K85/6574H10K85/6572Y02E10/549
Inventor 王湘成何睦王鹏何为
Owner 上海钥熠电子科技有限公司