Carbazole derivative and material and organic light-emitting device comprising same

A carbazole derivative, C6-C60 technology, applied in the field of carbazole derivatives, can solve the problems of unbalanced distribution of electrons and holes, uneven molecular weight distribution, and reduced luminous efficiency.

Active Publication Date: 2018-08-24
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most polymer materials have uneven molecular weight distribution and are hole transport materials, resulting in an unbalanced distribution of electrons and holes in the light-emitting layer, which reduces the luminous efficiency.

Method used

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  • Carbazole derivative and material and organic light-emitting device comprising same
  • Carbazole derivative and material and organic light-emitting device comprising same
  • Carbazole derivative and material and organic light-emitting device comprising same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] The preparation of embodiment 1 compound formula S-1 (synthetic scheme 1)

[0080] The structural formula of compound S-1 is shown in the following formula:

[0081]

[0082] The first step, the preparation of 2-nitro-4,4'-dimethylbiphenyl (Int.-1):

[0083]

[0084] Add 20g of 4,4'-dimethylbiphenyl S-0 in batches to 360ml of 85% nitric acid and 360ml of acetic acid mixed solution, control the temperature and stir at 40°C for 30 minutes, then pour the reaction solution into 2500ml of ice water , extracted three times with dichloromethane, and the organic phase was washed with anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated to dryness under reduced pressure, and recrystallized with methanol to obtain 23 g of Int.-1 as a yellow solid, with a yield of 92.5%.

[0085] The second step, the preparation of intermediate Int.-2:

[0086]

[0087] Mix 15g of the first-step intermediate Int.-1 with 100ml of dichlorobenzene, add 86.5g of t...

Embodiment 2

[0112] Embodiment 2, the preparation of compound formula S-8 (synthetic route 2)

[0113] The structural formula of compound S-8 is shown in the following formula:

[0114]

[0115] The first step, the preparation of intermediate Int.-8:

[0116]

[0117] 15g of the intermediate Int.-2 prepared in the second step of Example 1 was dissolved in 150ml of dry N,N-dimethylformamide, and under nitrogen protection, the temperature was cooled to 0°C with an ice-water bath, and 3.4g of NBS was stirred and reacted for 2 hours, then poured into ice water, filtered, the filter cake was washed with water, separated and purified by silica gel column to obtain 19.0 g of intermediate Int.-8, a white solid, with a yield of 90%.

[0118] The second step, the preparation of intermediate Int.-9:

[0119]

[0120] The first step intermediate Int.-8 of 10.0g is dissolved in the tetrahydrofuran of 80ml, under nitrogen protection, add the anhydrous sodium carbonate of 11.0g SM020 and 15.5g...

Embodiment 3

[0136] Embodiment 3, the preparation of compound formula S-25

[0137] The structural formula of compound S-25 is shown in the following formula:

[0138]

[0139] The first step, the preparation of intermediate Int.-12:

[0140]

[0141] 5.0 g of the seventh step product Int.-7 of Example 1, 2.3 g of raw material SM050, 4.0 g of sodium tert-butoxide, 42 mg of cuprous iodide and 60 ml of dry xylene were mixed, and deoxidized under vacuum for 10 minutes , under the protection of nitrogen, add 0.1ml of 10% tri-tert-butylphosphonium toluene solution, heat up and reflux for 24 hours, cool to room temperature, add 50ml of water to the reaction solution for dilution, separate the organic phase, and concentrate to dryness under reduced pressure. The residue was separated and purified by silica gel column to obtain 4.9 g of the intermediate formula Int.-12 as a yellow solid with a yield of 79%.

[0142] Second step, the preparation of compound formula S-25:

[0143]

[014...

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Abstract

The invention discloses a carbazole derivative and a material and an organic light-emitting device comprising the same. The carbazole derivative adopts a structural formula as follows: FORMULA. The carbazole derivative provided by the invention is soluble in an organic solvent, and has relatively high glass transition temperature, high heat stability and good carrier transport capacity. The carbazole derivative has a simple synthesis technology and a simple purification method and has the characteristics of suitability for large-scale production and the like, and through connection with different groups, the molecular energy level can be adjusted and the light-emitting property, the heat stability and the like are regulated, so that the carbazole derivative is an ideal choice as an organiclight-emitting device material. The light-emitting device prepared from the carbazole derivative provided by the invention has high light-emitting efficiency, good stability and a longer service life, so that the light-emitting efficiency and the service life of the device can meet a requirement on practicality.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent display and lighting. More specifically, it relates to a carbazole derivative, a material comprising the carbazole derivative, and an organic electroluminescent device. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D487/04C07D519/00C09K2211/1044C09K2211/1059C09K2211/1007C09K2211/1011C09K2211/1029H10K85/615H10K85/624H10K85/654H10K85/6572H10K50/00
Inventor 曹建华王士波张建川董梁隋岩唐永顺华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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