Oxidized thieno-bi-carbazole derivative and applications thereof

A technology of dicarbazole and derivatives, which is applied in the field of oxidative thienodicarbazole derivatives, can solve the problems of increasing the cost of device fabrication, achieve high glass transition temperature and decomposition temperature, good thermal stability, and improve luminous efficiency Effect

Active Publication Date: 2014-02-05
VALIANT CO LTD
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  • 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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  • Oxidized thieno-bi-carbazole derivative and applications thereof
  • Oxidized thieno-bi-carbazole derivative and applications thereof
  • Oxidized thieno-bi-carbazole derivative and applications thereof

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 under nitrogen gas for 1 hour 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 thieno-bi-carbazole derivative and applications thereof, which belong to the field of organic photoelectric materials. In a compound, an electron withdrawing group -SO- or -SO2- is introduced at 7- and carbazole derivatives are introduced at two ends so as to form the oxidized thieno-bi-carbazole derivative; the general formula of the oxidized thieno-bi-carbazole derivative is as shown in the specification, wherein -SO- or -SO2- has excellent electron transportation performance, thereby enhancing the electron affinity of the compound and the compound stability in air; simultaneously carbazoles with excellent hole transportation performance are introduced at the two ends, so that a transportation material with double polarity is formed. The oxidized thieno-bi-carbazole derivative can serve as a transportation material and a light emitting material of an OLED (Organic Light Emitting Diode) 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-methylphe nyl)-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 Applications(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
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