Thiaxanthene derivative and application thereof

A derivative, the technology of thioxanthene, applied in the field of organic electroluminescent materials, can solve the problems of low thermal stability and high driving voltage, and achieve the goal of reducing starting voltage, improving luminous efficiency and brightness, improving thermal stability and transporting electrons effect of ability

Active Publication Date: 2021-09-24
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, CN103833507B, CN107573328B, CN107556310B publicly authorized by the Chinese Patent Office and TPBI recorded in U.S. Patent No. 5,645,948 published by Kodak in 1996 are materials for the electron transport layer with imidazole groups. In its structure, 1 of benzene , There are three N-phenylbenzimidazolyl groups in the 3,5 substitution position. In terms of function, it not only has the ability to transport electrons, but also has the function of blocking holes from the light-emitting layer, but in practical applications When used in components, there are problems of low thermal stability and high driving voltage

Method used

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  • Thiaxanthene derivative and application thereof
  • Thiaxanthene derivative and application thereof
  • Thiaxanthene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The preparation method of compound CJHL814 comprises the following steps:

[0082] The first step: preparation of intermediate Int-1

[0083]

[0084] 50.0 mmol of 4-bromo-1-mercaptonaphthalene (CAS: 62648-52-6), 75.0 mmol of tolan (CAS: 501-65-5), 2.5 mmol of [(Cp*RhCl 2 ] 2 Catalyst (CAS: 12354-85-7), 0.1 mol of copper acetate monohydrate and 10.0 mmol of anhydrous sodium acetate were put into a pressure-resistant reactor, then 200 mL of dry acetonitrile was added, and the temperature was raised to 130°C under the protection of nitrogen The reaction was stirred for 12 hours, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain Int-1 as a yellow solid, yield: 46%.

[0085] The second step: the preparation of intermediate Int-2

[0086]

[0087] 50.0 mmol of Int-1 was dissolved in 120 mL of dichloromethane, under nitrogen protection, 5.0 mmol of anhydrous ferric chloride was added, sti...

Embodiment 2

[0106] The preparation of compound CJHL830 (with T 2 =CMe 2 example):

[0107]

[0108] 20.0 mmol of Int-2, 18.0 mmol of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (CAS: 897671-69- 1), 0.2 mmol of Pd 2 (dba) 3 Catalyst, 0.4 mmol of Xanphos and 30.0 mmol of sodium tert-butoxide, then add 80 mL of dry toluene, under the protection of nitrogen, raise the temperature to 100 °C and stir for 12 hours, then cool down to room temperature, add 50 mL of water, and use ethyl acetate Extract, collect the organic phase, concentrate to dryness under reduced pressure, separate and purify with silica gel column, and recrystallize with dichloromethane-ethanol to obtain yellow solid CJHL830, yield: 78%, MS (MALDI-TOF): m / z 694.2582[ M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.92~8.90 (1H, d); 8.86~8.84 (1H, d); 8.55~8.53 (1H, d); 8.33~8.27 (2H, m); 7.93~7.91 (1H, d); 7.69~7.57 (6H, m); 7.53~7.48 (4H, m); 7.45~7.38 (5H, m); 7.36~7.28 (5H, m); 7.26 (1H, s); 7.21~7.17 (2H, m); 1.68 (...

Embodiment 3

[0115] Preparation of compound CJHL847:

[0116]

[0117] Mix 50 mL of DMSO and 30.0 mmol of potassium hydroxide, stir at room temperature for 30 minutes, add 18.0 mmol of 9H-3,9'-biscarbazole (CAS: 18628-07-4), stir for 30 minutes, and then Add 20.0 mmol of Int-4, under the protection of nitrogen, raise the temperature to 80°C and stir for 5 hours, cool down to room temperature, add 200 mL of water, filter, wash the filter cake with water and ethanol, separate and purify with silica gel column, and then use two Chloromethane-THF recrystallization gave yellow solid CJHL847, yield: 88%, MS (MALDI-TOF): m / z 666.2018[M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.93~8.91 (1H, d); 8.86~8.84 (1H, d); 8.63~8.61 (1H, d); 8.36~8.34 (1H, d); 8.20 (1H, s); , m); 7.96 (1H, s); 7.89~7.79 (3H, m); 7.71~7.62 (2H, m); 7.58~7.44 (3H, m); 7.38~7.23 (9H, m); 7.21~7.17 (1H, m).

[0118] With reference to the above-mentioned similar synthetic method, the following compounds were prepared:

[0119]

...

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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a thiaxanthene derivative as shown in a formula I and application thereof. The thiaxanthene derivative as shown in the formula I provided by the invention has a tribenzothiaxanthene ring, so that the pi-pi conjugation strength of molecules is increased, and the thermal stability and the electron transporting capability of the material are improved. For an organic electroluminescent device prepared from the material, the starting voltage can be significantly reduced, and the luminous efficiency and the brightness can be improved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a thioxanthene derivative and its application. Background technique [0002] In general, the organic light-emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance. That is, when an organic layer is arranged between an anode and a cathode, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to the ground state, light and heat are emitted. [0003] As a method of effectively manufacturing organic electroluminescent elements, research has been carried out to replace the organic layer in a single-layer manufacturing element with a multilayer structure. In 1987, Tan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/04C07D409/10C07D409/14C07D409/04C07D409/12C07D495/04C07D519/00C07D495/06C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07D335/04C07D409/10C07D409/14C07D409/04C07D409/12C07D495/04C07D519/00C07D495/06C07F7/0816C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/104C09K2211/1096H10K85/622H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/40H10K85/6572H10K50/171H10K50/18H10K50/15H10K50/16H10K50/17H10K50/11
Inventor 赵雷韩洪波刘殿君唐怡杰边坤郭文龙邸庆童何连贞
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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