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Binaphthyl derivative, and material and organic electroluminescent device which contain binaphthyl derivative

A technology of binaphthalene derivatives and organic light-emitting layer, applied in the field of binaphthalene derivatives, can solve the problems of accelerated device degradation, poor device life, unstable thin films, etc.

Inactive Publication Date: 2018-10-09
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, many blue-light materials have been reported in the literature, and the structures of these materials can be roughly classified into anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene and spirofluorene, among which anthracene Derivatives such as 9,10-diphenylanthracene (DPA) and 9,10-bis(2-naphthyl)anthracene (ADN) are the progenitor materials used in organic electroluminescent components, although they have high fluorescence quantum efficiency and Good stability and other advantages, but its unstable film is one of the important reasons for accelerating device degradation and causing poor device life

Method used

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  • Binaphthyl derivative, and material and organic electroluminescent device which contain binaphthyl derivative
  • Binaphthyl derivative, and material and organic electroluminescent device which contain binaphthyl derivative
  • Binaphthyl derivative, and material and organic electroluminescent device which contain binaphthyl derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Embodiment 1, the preparation of compound formula DN-01

[0091] The first step, the preparation of intermediate Int.-1, the preparation route is as follows:

[0092]

[0093] The specific operation process of preparation:

[0094]20.0g (69.93mol) of raw material SM-0 was dissolved in 300ml of anhydrous dichloromethane, 27.5g (0.35mol) of pyridine and 1.5g of DMAP were added, and 43.4g (0.15mol) of trifluoromethanesulfonium was slowly added dropwise Acid anhydride dissolved in dichloromethane solution, stirred at room temperature for 8 hours, added 300ml of water and stirred for 30 minutes, collected organic phase and concentrated to dryness under reduced pressure, separated and purified with silica gel column, concentrated to dryness under reduced pressure to obtain 36.5g of white solid, yield 95 %.

[0095] The second step, the preparation of intermediate Int.-2, the preparation route is as follows:

[0096]

[0097] The specific operation process of preparat...

Embodiment 2

[0110] Embodiment 2, compound formula DN-02, DN-04, DN-16, DN-49, DN-57, DN-60, DN-66, DN-80, DN-99, DN-100, DN-101, Preparation of DN-109

[0111] Referring to the synthesis method of Example 1, the compounds DN-02, DN-04, DN-16, DN-49, DN-57, DN-60, DN-66, DN-80, DN-99, DN-100, DN-101, DN-109, that is, the method steps are the same as in Example 1, the only difference is that according to the desired product, different reactants are used to replace the phenylboronic acid in the second step of Example 1 according to actual needs, replacing Example 1 The phenylboronic acid of the 4th step; And change the quality consumption of this compound according to molar weight.

Embodiment 3

[0112] Embodiment 3, the preparation of compound formula DN-36

[0113] The first step, the preparation of intermediate Int.-4, the preparation route is as follows:

[0114]

[0115] The specific operation process of preparation:

[0116] Dissolve 10.0g (24.6mmol) of the intermediate Int.-2 in the second step of Example 1 with 200ml of dichloromethane, cool down to 0°C in an ice-salt bath, and slowly add 3.9g (24.6mmol) of bromine to dissolve in 10ml The solution of dichloromethane was stirred and reacted for 6 hours, 20ml of saturated aqueous sodium bisulfite solution was added, stirred and reacted for 10 minutes, the organic phase was collected, concentrated under reduced pressure to dryness, separated and purified by silica gel column, concentrated under reduced pressure to dryness, and 10.2g White solid, yield 86%.

[0117] The second step, the preparation of compound formula DN-36, the preparation route is as follows:

[0118]

[0119] The specific operation proc...

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Abstract

The invention discloses a binaphthyl derivative, and a material and an organic electroluminescent device which contain the binaphthyl derivative. The structure of the binaphthyl derivative is represented by formula I. The binaphthyl derivative represented by formula I possesses deep blue fluorescence performance, is capable of avoiding aggregation-caused quenching effect of fluorescent materials,and is relatively high in vitrification point, heat stability, and excellent in luminescent performance. The synthesis process is simple; a purification method is simple and is suitable for large-scale production; the luminescent performance and heat stability of products can be adjusted through connection with different groups; and the binaphthyl derivative is an ideal selection for organic luminescent layers of organic electroluminescent devices. The OLED devices prepared from the fluorescence material are high in fluorescent layer fluorescence efficiency, and stability, so that device fluorescence efficiency and service life are capable of satisfying practical requirements.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence. More specifically, it relates to a binaphthyl derivative, a material comprising the binaphthyl 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 flat panel displays...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/24C07D307/91C07C15/27C07C15/38C07D251/24C07C15/20C07D239/26C07D401/10C07D213/16C07C15/30C07C15/28C07C211/58C07C211/61C07D219/02C07D223/22C07D241/46C07D265/38C07D209/88C07B59/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07B59/001C07B59/002C07C15/20C07C15/24C07C15/27C07C15/28C07C15/30C07C15/38C07C211/58C07C211/61C07D209/88C07D213/16C07D219/02C07D223/22C07D239/26C07D241/46C07D251/24C07D265/38C07D307/91C07D401/10C07B2200/05C09K2211/1059C09K2211/1033C09K2211/1044C09K2211/1014C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1088H10K85/624H10K85/622H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/654H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor 曹建华王士波董梁张建川隋岩唐永顺
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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