Fluorene derivative organic electroluminescence device

A technology of fluorene compounds and substituents, applied in the field of organic electroluminescent devices, can solve problems such as uneven molecular weight distribution, unbalanced distribution of electrons and holes, and reduced luminous efficiency

Inactive Publication Date: 2019-09-13
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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  • Fluorene derivative organic electroluminescence device
  • Fluorene derivative organic electroluminescence device
  • Fluorene derivative organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The preparation method of compound FP31 comprises the following reaction steps:

[0073] Step 1: Preparation of Intermediate Int.-1

[0074]

[0075] The 3-bromo-2-iodophenol of 10.0g (33.4mmol) mixes with 80ml toluene, adds the palladium catalyst Pd ( PPh 3 ) 4 , then add 40ml of ethanol and 40ml of water, heat up and reflux and stir for 12 hours, cool to room temperature, extract with ethyl acetate, dry the organic phase, filter, concentrate the filtrate to dryness under reduced pressure, separate and purify on a silica gel column, and obtain 7.7g of pink solid Int. -1, 92% yield.

[0076] The second step: the preparation of intermediate Int.-2

[0077]

[0078] 10.0g (40.1mmol) of Int.-1 prepared in the first step was dissolved in 150ml of dry THF, under the protection of nitrogen, 4.5g (40.1mmol) of potassium tert-butoxide was added, and the temperature was lowered to -78°C with liquid nitrogen. Add 19.3ml of 2.5M n-butyllithium n-hexane solution dropwise...

Embodiment 2

[0092] Preparation of Compounds FP01~FP30, FP32~FP66 and FP102~FP108

[0093] Referring to the synthesis method of Example 1, the compounds shown in FP01~FP30, FP32~FP66 and FP102~FP108 were prepared, the difference is that according to the different products, different intermediates were selected to replace the intermediate in the sixth step of Synthesis Example 1 The corresponding compounds FP01-FP30, FP32-FP66 and FP102-FP108 were prepared from body L01.

Embodiment 3

[0095] The preparation method of compound FP67 comprises the following reaction steps:

[0096] The first step: the preparation of intermediate Int.-6

[0097]

[0098] 5.0g (23.3mmol) of intermediate Int.-2 and 80ml of tetrahydrofuran were mixed, and 4.2g (19.5mmol) of methyl o-bromobenzoate, 12.4g (46.6mmol) of potassium phosphate hydrate, 0.16g of palladium catalyst Pd were added (PPh 3 ) 4 , then add 20ml of water, heat up to reflux and stir for 12 hours, cool to room temperature, add 100ml of water to dilute, extract with ethyl acetate, dry the organic phase, filter, concentrate the filtrate to dryness under reduced pressure, separate and purify on a silica gel column, and obtain 4.3g of yellow Solid Int.-6, 72% yield.

[0099] The second step: the preparation of intermediate Int.-7

[0100]

[0101] 8.0g (26.3mmol) of the intermediate Int.-6 prepared in the first step was dissolved in 120ml of dry tetrahydrofuran, and under the protection of nitrogen, the tempe...

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PUM

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Abstract

The invention discloses fluorene compounds represented by a formula I shown in the description, a material containing the fluorene compounds and an organic electroluminescence device containing the fluorene compounds. The fluorene compounds provided by the invention have a special fluorene ring structure, can effectively block intramolecular conjugation, and increase the energy level width; the organic electroluminescent device prepared by utilizing the material provided by the invention has higher component efficiency and luminescence service life; and in addition, the fluorene compounds havehigher molecular rigidity and higher glass transition temperature, when the compounds are applied to an industrial process, the compounds have the advantages of having better thermal stability, and being easy to prepare and easy to purify, and the compounds are ideal choice as the organic electroluminescence device material.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials. More specifically, it relates to a fluorene compound, and an organic electroluminescent device comprising the fluorene compound. Background technique [0002] After more than 20 years of development, organic EL materials have fully realized red, blue, and green luminescence, and the application field has also expanded from small molecules to polymers and metal complexes. In recent years, the organic electroluminescence display technology has become mature. The traditional vacuum evaporation method is used to prepare lighting or display equipment. Some products have entered the market, but the material utilization rate is low and the yield rate is low, resulting in high production costs. The OLED solution process, which belongs to the third-generation technology, uses the RGB light-emitting materials sprayed by printing inkjet equipment to form pixels, and the three R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07D209/86C07D209/88C07D401/12C07D213/38C07D251/24C07D401/10C07D401/14C07D403/10C07D239/26C07D213/16C07D519/00C07C15/28C07C15/38C07F9/53C07F9/58C07F9/6512C07F9/6521C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07D209/86C07D209/88C07D401/12C07D213/38C07D251/24C07D401/10C07D401/14C07D403/10C07D239/26C07D213/16C07D519/00C07C15/28C07C15/38C07F9/5325C07F9/58C07F9/6512C07F9/6521C07F9/6561C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C07C2603/42C07C2603/94C07C2603/18C07C2603/24C07C2603/26H10K85/615H10K85/622H10K85/624H10K85/626H10K85/636H10K85/633H10K85/654H10K85/6572H10K50/11H10K50/15H10K50/16H10K50/18
Inventor 曹建华郭剑王士波隋岩贾敏慧唐永顺
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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