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OLED material with carrier transmittability as well as preparation method and application thereof

A technology of transport ability and carrier, which is applied in the preparation of organic compounds, luminescent materials, and preparation of carboxylic acid nitriles, etc.

Active Publication Date: 2013-12-25
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, organic electroluminescent display technology has become mature, and some products have entered the market. However, in the process of industrialization, there are still many problems to be solved, especially the carrier injection of various organic materials used to make devices. , transmission performance, material electroluminescence performance, service life, color purity, matching between various materials and electrodes, etc., there are still many problems that have not yet been resolved.

Method used

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  • OLED material with carrier transmittability as well as preparation method and application thereof
  • OLED material with carrier transmittability as well as preparation method and application thereof
  • OLED material with carrier transmittability as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] Preparation of compound LM005:

[0145] 1.1 Preparation of Intermediate S-1:

[0146]

[0147] Add 0.1mol titanium trichloride-aluminum chloride (78.5%) and 200ml anhydrous THF to the reaction flask, add 0.05mol lithium aluminum hydride under stirring at room temperature, and stir for 10 minutes; then slowly drop 0.049mol triethylamine into In the reaction flask, and stirred for 1 hour; then 10mmol of raw material 5-dibenzocycloheptenone (S-0) and 10mmol of 2,7-dibromo-9-fluorenone were added to the reaction flask, heated to reflux and stirred React for 20 hours; after the reflux reaction is completed, cool to room temperature, slowly drop 200ml of water into the reaction flask, and suction filter after stirring; The residue obtained after drying was recrystallized from ethanol to obtain 3.84 g of a yellow solid, namely intermediate S-1; the yield was 75%.

[0148] 1.2 Preparation of compound LM005:

[0149]

[0150] Add 4mmol of intermediate S-1, 8.6mmol of ...

Embodiment 2

[0157] Preparation of compound LM052:

[0158] 2.1 Preparation of intermediate S-1:

[0159] Intermediate S-1 was prepared with reference to step 1.1 in Example 1, the difference being that the raw material 5-dibenzocycloheptenone in step 1.1 of Example 1 was replaced by 3,7-difluoro-5-dibenzo Cycloheptenone, its consumption is constant.

[0160] 2.2 Preparation of compound LM052:

[0161]

[0162] Add 3.6mmol of intermediate S-1, 9mmol of 4-pyridineboronic acid, 21.7mmol of anhydrous potassium carbonate, 50mg of Pd(PPh 3 ) 4 Catalyst, 100ml of toluene, 50ml of ethanol and 50ml of water, under the protection of nitrogen, heat up and reflux for 24 hours; after the reaction, cool to room temperature; The organic phases were combined; the organic phase was concentrated to dryness under reduced pressure, and the obtained residue was separated and purified with a silica gel column to finally obtain 1.4 g of a yellow solid, namely compound LM052; the yield was 71%.

[0163...

Embodiment 3

[0169] Preparation of compound LM006:

[0170] 3.1 Preparation of Intermediate S-1:

[0171] Intermediate S-1 was prepared referring to step 1.1 in Example 1.

[0172] 3.2 Preparation of compound LM052:

[0173]

[0174] Add 4mmol of intermediate S-1, 9.6mmol of carbazole, 11.4mmol of sodium tert-butoxide and 100ml of xylene into the reaction flask, and then add 25mg of Pd(OAc) under stirring 2 Catalyst and 45mg of tert-butylphosphine, under the condition of nitrogen protection, reflux reaction for 10-12 hours; after the reaction, cool to room temperature, add 50ml of water to the reaction bottle, stir and separate the layers, separate the organic phase, and use the water phase Extract with dichloromethane; collect and combine organic phases, add anhydrous MgSO 4 Drying and suction filtration; the filtrate was concentrated to dryness under reduced pressure, and the obtained residue was separated and purified with a silica gel column; the obtained product was recrystall...

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Abstract

The invention discloses an OLED (Organic Light-Emitting Diode) material with carrier transmittability, and the structure of the OLED material is shown in formula I. The OLED material is excellent in performance as the carrier transmittability and the luminous efficiency of a device are improved. The invention further discloses a preparation method and application of the OLED material. A synthetic route of the OLED material is simple and easy to operate, and the reaction yield is higher, so that the OLED material has excellent industrialization prospect; an OLED prepared by using the OLED material can realize high luminance, high efficiency and low voltage, can effectively avoid screen dim spots, and has better performance.

Description

technical field [0001] The invention relates to a novel OLED material with carrier transport capability, which belongs to the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescence (EL for short) is a phenomenon in which organic materials are excited by electrical energy to emit light. As early as 1963, M. Pope et al. of New York University first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Dr. C.W.Tang of Kodak Corporation of the United States used the principle of organic electroluminescence to use 8-hydroxyquinoline aluminum (Alq 3 ) as the light-emitting layer, vacuum evaporation made a low driving voltage (about 10V), high efficiency (1.5lm / W), high brightness (1000cd / m 2 )’s multilayer structure organic light-emitting device (OrganicLight-EmittingDiode, referred to as OLED), which has aroused great interest of scholars from all over the world, and has s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/61C07C209/10C07D209/86C07D307/91C07D209/88C07D333/76C07D209/08C07D207/323C07D207/325C07D213/06C07D401/04C07D239/26C07D237/08C07D333/08C07F9/53C07F7/08C07F7/12C07F7/10C07D213/26C07D333/12C07C255/58C07C253/30C07C255/34C07C255/35C07C255/52C07D213/57C07D333/24C07D249/08C07D271/107C07D235/18H01L51/54
Inventor 曹建华华瑞茂逄辉王士波黄红亮李雅敏
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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