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Novel compound with spiral structure and application of same to OLED device

A technology of spiro ring structure and compound, applied in the field of organic electroluminescence display, can solve the problems of film uniformity destruction, low glass transition temperature, easy crystallization of materials, etc.

Active Publication Date: 2019-11-19
北京燕化集联光电技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The organic hole transport materials currently reported are generally small in molecular weight and have a low glass transition temperature. During the use of the material, repeated charging and discharging will easily crystallize the material and destroy the uniformity of the film, thus affecting the service life of the material.

Method used

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  • Novel compound with spiral structure and application of same to OLED device
  • Novel compound with spiral structure and application of same to OLED device
  • Novel compound with spiral structure and application of same to OLED device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Synthesis of (Compound 1-1)

[0061] The synthetic route is as follows:

[0062]

[0063] Including the following specific steps:

[0064] Synthesis of compound I-1

[0065] A 1-liter three-necked flask equipped with a magnetic stirrer, and potassium tert-butoxide (36.2 g, 0.376 mol), bis(4-tolyl)amine (41.37 g, 0.21 mol, purity 99%) and 100 ml of toluene were added sequentially after argon replacement. After replacing with argon again, 3.4 ml of tri-tert-butylphosphine and 0.5 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of (58.6g, 0.1mol, purity 99%) M1 and 100ml toluene, and control the temperature at 80-120°C. Cool down to 50°C, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF, and rotary steam to obtain 68.80g of white solid with a purity of 99.5% and a yield of about 84%.

[0...

Embodiment 2

[0068] Synthesis of (Compound 1-30)

[0069] The synthetic route is as follows:

[0070]

[0071] Synthesis of compound I-30

[0072] 1 liter three-neck flask, equipped with magnetic stirring, after argon replacement, add potassium tert-butoxide (36.2g, 0.376mol), 4-tolyl-2-naphthylamine (48.93g, 0.21mol, purity 99%) and toluene 100ml . After replacing with argon again, 3.4 ml of tri-tert-butylphosphine and 0.5 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of (58.6g, 0.1mol, purity 99%) M2 and 100ml toluene, and control the temperature at 80-120°C. Cool down to 50°C, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, boil the filter cake several times with DMF, and rotary evaporate to obtain 76.63g of white solid with a purity of 99.5% and a yield of about 86%.

[0073] Product MS (m / e): 890.28; Elemental analysis (C 63 h 42 N 2 S 2 ):...

Embodiment 3

[0075] Synthesis of (Compound I-76)

[0076] The synthetic route is as follows:

[0077]

[0078] Synthesis of compound I-76

[0079] A 1-liter three-neck flask equipped with a magnetic stirrer. After argon replacement, 19.93g (0.188mol) of sodium carbonate, 9,9-dimethyl-2-boronic acid (23.8g, 0.1mol, purity 99%) and 100ml of toluene were added in sequence. After replacing with argon again, 0.23g of Pd132 was added in sequence. After the addition, the temperature was raised to 80°C. Start to drop a solution consisting of (47.5g, 0.1mol, purity 99%) M3 and 100ml toluene, and control the temperature at 75-80°C. Cool down to room temperature, add 100ml of deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF to obtain 49.98g of white solid with a purity of 99.5% and a yield of about 85%.

[0080] Product MS (m / e): 588.21; Elemental analysis (C 44 h 28 o 2 ): theoretical value C: 89.77%, H: 4.79%, O: 5.44%; measure...

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PUM

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Abstract

The invention relates to a novel compound with a spiral structure. The novel compound has a structure represented by a general formula I which is described in the specification. In the general formulaI, E represents an O, S or Se atom; R1, R2, R3 and R4 each independently represent an H atom or an aromatic group containing n benzene rings and / or aromatic heterocycles and having an electron withdrawing property or neutrality; and n represents an integer in a range of 1-7. A novel material provided by the invention uses the compound with the spiral structure as a mother nucleus and an aromaticcompound as an end group; and an electron donating group or a neutral group with hole transport performance is introduced to the active position of the spiro compound, so a novel OLED material with hole transport performance is obtained. The material has high hole mobility, good film stability, proper molecular energy level and high luminous efficiency, can be applied to the field of organic electroluminescence, and is applicable as a hole transport material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and specifically relates to a novel organic material with a spiro ring structure and its application. Background technique [0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescent display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backlight, has a wid...

Claims

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Application Information

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IPC IPC(8): C07D493/10C07D495/10C07D517/10H01L51/54H01L51/50
CPCC07D517/10C07D493/10C07D495/10H10K85/624H10K85/615H10K85/636H10K85/626H10K85/633H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/15
Inventor 范洪涛呼建军梁现丽段陆萌黄春雪杭德余李仲庆曹占广刘阳班全志李继响罗忠林
Owner 北京燕化集联光电技术有限公司
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