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Triphenylene derivative, light-emitting element material and light-emitting element

A derivative, triphenylene technology, applied to triphenylene derivatives, can solve problems such as lack of materials, and achieve the effects of easy availability of raw materials, high-efficiency luminescence performance, and reduction of vibration energy loss

Pending Publication Date: 2021-09-17
ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, host materials with both high triplet energy levels and good hole mobility are still lacking.

Method used

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  • Triphenylene derivative, light-emitting element material and light-emitting element
  • Triphenylene derivative, light-emitting element material and light-emitting element
  • Triphenylene derivative, light-emitting element material and light-emitting element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of compound 1

[0068]

[0069] Under an argon atmosphere, 50.5 grams (100 mmol) of N-(7,10-dibromoterphenyl-2-yl) benzamide and 12.5 grams (120 mmol) of 2-chloropyridine were added to the reaction flask, and 300 ml of methylene chloride was cooled to -78°C, then 31.0 g (110 mmol) of trifluoromethanesulfonic anhydride was added, and the reaction mixture was placed in an ice-water bath and heated to 0°C. 11 g (110 mmol) of benzonitrile was added. The reaction mixture was heated to 45°C and reacted for 6 hours, then cooled to room temperature and triethylamine was added to neutralize trifluoromethanesulfonate. The volatiles were removed under reduced pressure, and 51.9 g of 3,6-dibromo-11,13-diphenylphenanthroquinazoline were obtained by flash column chromatography (eluent: 10% ethyl acetate in hexane), Yield 88%, HPLC purity 99.6%.

[0070] 1 HNMR(DMSO): δ9.10(s, 1H), 8.93(s, 1H), 8.81(d, 1H), 8.35(m, 2H), 8.29(s, 1H), 8.12(s, 1H), 8.05 ~7.99(m, 3H), 7.8...

Embodiment 2

[0074] Synthesis of compound 20

[0075]

[0076] Under an argon atmosphere, 50.5 grams (100 mmol) of N-(7,10-dibromoterphenyl-2-yl) benzamide and 12.5 grams (120 mmol) of 2-chloropyridine were added to the reaction flask, and 300 ml of methylene chloride was cooled to -78°C, then 31.0 g (110 mmol) of trifluoromethanesulfonic anhydride was added, and the reaction mixture was placed in an ice-water bath and heated to 0°C. 11 g (110 mmol) of benzonitrile was added. The reaction mixture was heated to 45°C and reacted for 6 hours, then cooled to room temperature and triethylamine was added to neutralize trifluoromethanesulfonate. The volatiles were removed under reduced pressure, and 51.9 g of 3,6-dibromo-11,13-diphenylphenanthroquinazoline were obtained by flash column chromatography (eluent: 10% ethyl acetate in hexane), Yield 88%, HPLC purity 99.6%.

[0077] 1 HNMR(DMSO): δ9.10(s, 1H), 8.93(s, 1H), 8.81(d, 1H), 8.35(m, 2H), 8.29(s, 1H), 8.12(s, 1H), 8.05 ~7.99(m, 3H), 7....

Embodiment 3

[0082] Synthesis of Compound 28

[0083]

[0084] Under an argon atmosphere, add 46.0 grams (100 mmol) of N-(7-bromo-10-chlorobenzo-2-yl) benzamide and 12.5 grams (120 mmol) of 2-chloropyridine to 300 ml of dichloromethane in the reaction flask, and cool down to -78°C, then added 31.0 g (110 mmol) of trifluoromethanesulfonic anhydride, and placed the reaction mixture in an ice-water bath and heated to 0°C. Added 11 g (110 mmol) of benzonitrile. The reaction mixture was heated to 45°C and reacted for 6 hours, then cooled to room temperature and triethylamine was added to neutralize trifluoromethanesulfonate. The volatiles were removed under reduced pressure and flash column chromatography (eluent: 10% ethyl acetate in hexane) gave 46.3 g of 6-bromo-3-chloro-11,13-diphenylphenanthroquinazoline , yield 85%, HPLC purity 99.4%.

[0085] 1 HNMR(DMSO): δ9.10(s, 1H), 8.93(s, 1H), 8.81(d, 1H), 8.35(m, 2H), 8.29(s, 1H), 8.12(s, 1H), 8.05 ~7.99(m, 3H), 7.80(d, 2H), 7.65(t, 2H), 7....

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Abstract

The present invention relates to a triphenylene derivative for an organic light-emitting element, a light-emitting element material containing the triphenylene derivative, and a light-emitting element, and more specifically, to a soluble organic compound having excellent color purity and high brightness and light-emitting efficiency, and an OLED device using the compound. The compound is characterized by being represented by a general formula (1).

Description

technical field [0001] The present invention relates to triphenylene derivatives for organic light-emitting elements, light-emitting device materials and light-emitting devices containing triphenylene derivatives, more specifically, to a soluble organic compound with excellent color purity, high brightness and luminous efficiency, and its use OLED devices of this compound. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, referred to as OLED). The light-emitting device has attracted attention because of its thin profile, high-intensity light emission at a low driving voltage, and multi-color light emission by selecting a light-emitting material. [0003] Since C.W.Tang of Kodak Company revealed that organic thin film components can emit light with high brightness, a large number of researchers in the OLED industry have done a lot of research and advancement on its application. Organic thin film light-emitting devices are widely used ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D409/14C07D409/04C07D405/04C07D239/70C07D403/04C07D403/14C07D413/14C07D417/14C07D417/04C07D413/04C07D401/14C07D401/04C09K11/06H01L51/54H01L51/50
CPCC07D405/14C07D409/14C07D409/04C07D405/04C07D239/70C07D403/04C07D403/14C07D413/14C07D417/14C07D417/04C07D413/04C07D401/14C07D401/04C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092H10K85/622H10K85/624H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15H10K50/16H10K50/17H10K50/171H10K50/11Y02E10/549
Inventor 王鹏
Owner ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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