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A kind of oxidized thienodicarbazole derivative and its application

A technology of dicarbazole and derivatives, which is applied in the field of oxidized thienodicarbazole derivatives, can solve the problems of increased device manufacturing costs, achieve high glass transition temperature and decomposition temperature, improve luminous efficiency, and good thermal stability Effect

Active Publication Date: 2016-03-09
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to balance the carrier injection rate and improve the luminous efficiency of the device, an electron transport layer composed of an electron transport material and a hole transport layer composed of a hole transport material are usually introduced into the light emitting device, but the electron and hole transport The introduction of layers often leads to an increase in the cost of device fabrication

Method used

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  • A kind of oxidized thienodicarbazole derivative and its application
  • A kind of oxidized thienodicarbazole derivative and its application
  • A kind of oxidized thienodicarbazole derivative and its application

Examples

Experimental program
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Effect test

Embodiment 15

[0058] Example 15, Synthesis of 9-diphenyl-5,9-dihydrothieno[2,3-b:5,4-b']dicarbazole-7,7-dioxide (Compound 1):

[0059] Take 5,9-dihydrothieno[2,3-b:5,4-b']dicarbazole-7,7-dioxide (19.7g, 50.0mmol) and sodium hydride (6.0g, 150mmol, 60% content), dissolved in 60mL N,N-dimethylformamide, and stirred for 1 hour under nitrogen gas to remove the oxygen in the reaction flask. Below 0°C, bromobenzene (23.0 g, 150 mmol) was added dropwise, and the reaction process was tracked and detected by TLC. After reacting for 3 hours, 150 mL of deionized water was slowly added to the reaction solution, and 26.3 g of off-white solid powder was obtained by filtration. The crude product was sublimated and purified in a chemical vapor deposition system at 320°C to obtain 24.6 g of off-white solid powder, with a yield of 90%. ). Using DEI-MS to identify the compound, formula C 36 h 22 N 2 o 2 S, detection value [M+1] + =546.96, the calculated value is 546.64.

Embodiment 25

[0060] Example 25,9-two (naphthalene-1-yl)-5,9-dihydrothieno[2,3-b:5,4-b']dicarbazole-7,7-dioxide (compound 2)

[0061] Use 5,9-dihydrothieno[2,3-b:5,4-b']dicarbazole-7,7-dioxide and 1-bromonaphthalene as starting materials according to compound 1 in Example 1 prepared by synthetic method. Using DEI-MS to identify the compound, formula C 44 h 26 N 2 o 2 S, detection value [M+1] + =647.33, the calculated value is 646.75.

Embodiment 35

[0062] Example 35, 9-bis(naphthalene-1-yl)-5,9-dihydrothieno[2,3-b:5,4-b']dicarbazole-7-oxide (compound 3)

[0063] Use 5,9-dihydrothieno[2,3-b:5,4-b'] dicarbazole-7-oxide and 1-bromonaphthalene as starting materials according to the synthetic method of compound 1 in Example 1 preparation. Using HR-MS to identify the compound, formula C 44 h 26 N 2 OS, detection value [M+1] + =631.29, the calculated value is 630.76.

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Abstract

The invention relates to an oxidized thienodicarbazole derivative and an application thereof, belonging to the field of organic photoelectric materials. In this compound, an electron-withdrawing group -SO- or -SO2- is introduced at the 7-position, and a carbazole derivative is introduced at both ends to form an oxidized thienodicarbazole derivative. The general formula is: where, -SO- or - SO2- has good electron transport properties, which increases the electron affinity of the compound and its stability in the air; at the same time, carbazole with good hole transport properties is introduced at both ends to form a bipolar transport material. The oxidized thienobiscarbazole derivative of the invention can be used as a transmission material and a luminescent material of an OLED light-emitting device, and the prepared OLED device has the effect characteristics of high brightness, high efficiency and low voltage.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an oxidized thienobiscarbazole derivative and its application. Background technique [0002] The study of organic electroluminescent devices began in the 1930s. In 1936, Destriau dispersed organic fluorescent compounds in polymers to make thin films, and obtained the earliest electroluminescent devices. However, due to the thicker films , the turn-on voltage was very high, and it did not attract everyone's attention at that time; but in 1982, P.S.Vincett et al. prepared a 0.6μm thick anthracene film by vacuum deposition, and reduced the driving voltage of the device to below 30V, which began to attract attention. In 1987, it was a milestone year for organic electroluminescent devices. C.W.Tang et al. used ultra-thin film technology to use a diamine derivative N,N,-diphenyl-N,N ,-bis(3-methylphenyl)-1,1,biphenyl-4,4,diamine(TPD) was used as the hole transport layer ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C09K11/06H01L51/54
CPCC09K11/06C07D495/14C09K2211/1029C09K2211/1092H10K85/615H10K85/654H10K85/657H10K85/6572
Inventor 林存生郭文波付文岗任辉彩刘英瑞石宇董凯
Owner VALIANT CO LTD