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Heat-resistant organic semiconductor

An organic and organic compound technology, applied in the field of heat-resistant organic semiconductor materials, can solve problems such as poor solubility and difficult film formation

Inactive Publication Date: 2014-10-08
GUANMAT OPTOELECTRONICS MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, the literature (Appl. Phys. Lett., 2007, 90, 183503, etc.) reported hole transport materials composed of biphenyl and aromatic amines, but the solubility was poor and film formation was difficult.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1: Synthesis of compound (2) and compound (16).

[0106] (1) Synthesis of compound SM1

[0107]

[0108] Step1: Synthesis of compound TM1:

[0109] Weigh (14.8g, 40mmol) of 2,7-dibromophenanthrenequinone, (9.2g, 44mmol) of dipropiophenone in a 500ml three-neck flask, measure 200mL of methanol into the flask, add 2.5g of KOH, and heat up Reaction at 50° C. for 1 h, vacuum filtration to remove the solvent to obtain a gray-green solid, put into an oven and dry to obtain 18.0 g of product, yield = 82.4%;

[0110] Step2: Synthesis of compound TM2:

[0111] Weigh (3.0g, 40mmol) TM1, (0.6g, 6.1mmol) trimethylsilylacetylene 250ml three-neck flask, measure 20mL xylene in the flask, heat up to reflux, continue stirring overnight, and concentrate under reduced pressure To dryness, separated and purified by silica gel column chromatography to obtain 1.2 grams of product, yield = 35%;

[0112] Step3: Synthesis of compound SM1:

[0113] Weigh (0.9g, 1.5mmol) of TM2...

Embodiment 2

[0120] Example 2: Synthesis of compound (11), compound (36) and compound (36).

[0121] (1) Synthesis of compound SM2:

[0122]

[0123] Step1: Synthesis of compound TM1:

[0124] Weigh (21.2g, 60mmol) 2,7-dibromophenanthrenequinone, (13.2g, 66mmol) dipropiophenone in a 500ml three-neck flask, measure 300mL of methanol into the flask, add 3.7g of KOH, and heat up Reaction at 50°C for 1 h, vacuum filtration to remove the solvent to obtain a gray-green solid, put into an oven to dry to obtain 30 g of product, yield = 85%;

[0125] Step2: Synthesis of compound TM2:

[0126] Weigh (12g, 22mmol) TM1, (2.4g, 24.5mmol) trimethylsilylacetylene 250ml three-neck flask, measure 90mL xylene in the flask, heat up to reflux, continue stirring overnight, and concentrate under reduced pressure to Dry, separate and purify by silica gel column chromatography to obtain 4.3 grams of product, yield=32%;

[0127] Step3: Synthesis of compound SM2:

[0128] Weigh (4.3g, 7mmol) of TM2 into...

Embodiment 3

[0140] Embodiment 3: device application example.

[0141] OLED preparation and comparison: in a background vacuum up to 10 -5 Pa's multi-source evaporation OLED preparation equipment adopts the following device structure: ITO / mTDATA (100 ?) / HTL (400 ?) / Host: 5% luminescent dopant 6% (300 ?) / TPBi (300 ?) / LiF(10 ?) / Al, using different HTL or different blue-emitting dopant OLED light-emitting devices for comparison. Wherein the vacuum deposition speed of each organic layer and electrode is listed in Table 2 at time.

[0142] Table 2: Preparation conditions of OLED devices (doping wt concentration in the light-emitting layer is 9%)

[0143] 。

[0144] Table 3: OLED device performance (1000 Cd / cm 2 )

[0145]

[0146] Table 3 shows that in the green triplet OLED (device B) as an example of compound 11 of the present invention, the HTL used as the hole transport layer is higher than that of the green OLED (device A) using classical NPB as the HTL at 2000 nits 70 o In t...

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Abstract

The invention discloses an organic semiconductor material. The organic semiconductor material is characterized in that a benzophenanthrene derivative is used as an inner core of arylamine, so that the organic semiconductor material has hole transport luminescence property, heat stability and excellent electrochemical stability; when the material is applied to organic light emitting diodes, devices can obtain heat resistance and excellent working life.

Description

technical field [0001] The invention relates to an organic light-emitting material and its application in an organic light-emitting device, in particular to a heat-resistant organic semiconductor material, which can be applied to an organic light-emitting OLED device to improve device performance. Background technique [0002] Organic semiconductor materials are new types of optoelectronic materials. Its large-scale research originated in 1977 when Hideki Shirakawa, A. Heeger and A. McDiamid jointly discovered doped polyacetylene with a conductivity up to copper level. Subsequently, in 1987, C. Tang of KodaK Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R. Friend and A. Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S. Forrest and M. Thomson invented a more efficient organic phosphorescent light-emitting diode PHOLED. Because organic semiconductor materials have a structure that can be ea...

Claims

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Application Information

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IPC IPC(8): C07D333/20C07D333/36C07C211/61C07C209/10C07C217/84H01L51/54
CPCC07C211/54C07C211/58C07C211/61C07C217/92C07D333/20C07D333/36H10K85/655H10K85/636H10K85/633H10K85/631
Inventor 李晓常吴江
Owner GUANMAT OPTOELECTRONICS MATERIALS INC
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