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*derivatives, materials containing the same and organic electroluminescent devices

A derivative, electromechanical technology, applied in the field of organic electroluminescent devices, can solve problems such as unstable thin films, accelerated device degradation, and poor device life

Active Publication Date: 2018-09-28
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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  • *derivatives, materials containing the same and organic electroluminescent devices
  • *derivatives, materials containing the same and organic electroluminescent devices
  • *derivatives, materials containing the same and organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1, the preparation of compound formula A-1

[0089] The first step, 11-(4-bromophenyl)-3-chloro The preparation, preparation route is as follows:

[0090]

[0091] The specific operation process of preparation:

[0092] 20.0g (0.07mol) of raw material SM-0 was dissolved in 360ml of anhydrous dichloromethane, cooled to 0°C in an ice-salt bath, 13.5g (46.8mmol) of raw material SM-1 was added, and 11.2g (74.9mmol) of SM-1 was slowly added dropwise. ) of trifluoromethanesulfonic acid dissolved in dichloromethane, stirred for 1 hour, heated to 30 ° C, stirred for 18 hours, concentrated under reduced pressure to dryness, separated and purified with silica gel column, concentrated under reduced pressure to dryness, and obtained 13.2 g of white Solid, yield 45%.

[0093] The second step, the preparation of 2-bromo-4,4'-dibromomethylene biphenyl, the preparation route is as follows:

[0094]

[0095] The specific operation process of preparation:

[0096] ...

Embodiment 2

[0100] Embodiment 2, the preparation of compound formula A-17

[0101] The first step, intermediate 2,9-dichloro-5-(1-naphthyl) The preparation, preparation route is as follows:

[0102]

[0103] The specific operation process of preparation:

[0104] Referring to the preparation method in the first step of Example 1, SM-1 in the first step of Example 1 was replaced with SM-4 to obtain the intermediate Int.-2, a white solid, with a yield of 38%.

[0105] The second step, the preparation of compound formula A-17, the preparation route is as follows:

[0106]

[0107] The specific operation process of preparation:

[0108] The palladium catalyst Pd(PPh 3 ) 4 And the sodium carbonate of 10g (94.3mmol), then add the toluene of 60ml, the ethanol of 20ml and the water of 20ml, under the protection of nitrogen, heat up and reflux and stir reaction for 12 hours, cool to room temperature, extract with ethyl acetate, organic phase with Dry over sodium sulfate, filter, and c...

Embodiment 3

[0112] Embodiment 3, the preparation of compound formula A-33

[0113] The first step, intermediate 11-([1,1'-biphenyl]-2-yl)-2-chloro The preparation, preparation route is as follows:

[0114]

[0115] The specific operation process of preparation:

[0116] Referring to the preparation method of the first step of Example 1, SM-0 in the first step of Example 1 was replaced by SM-5, and SM-1 was replaced by SM-6 to obtain the intermediate Int.-3, a white solid, obtained as rate 47%.

[0117] The second step, the preparation of compound formula A-33, the preparation route is as follows:

[0118]

[0119] The specific operation process of preparation:

[0120] Referring to the preparation method of the second step of Example 2, replace Int.-2 in the second step of Example 2 with Int.-3, and replace phenylboronic acid with 2-phenylphenylboronic acid to obtain product A-33, a white solid , yield 88%.

[0121] Experimental data:

[0122] (1) 1 HNMR (δ, CDCl3): 9.06(d,...

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Abstract

The invention discloses a type of (the formula is shown in the formula) derivative, material comprising this (the formula is shown in the formula) derivative and organic electroluminescent device. The(the formula is shown in the formula) structural formula of the derivative is shown in the following formula I: (the formula is shown in the formula) The derivative (the formula is shown in the formula) provided by the derivatives, materials containing the same and organic electroluminescent devices as shown by the formula I, has the deep blue fluorescent property, which overcomes the fluorescentaggregation quenching effect of the fluorescent material, and has higher glass transition temperature, high thermal stability and excellent luminescence performance. The properties such as simple synthesis process, simple purification method suitable for large-scale production, and the properties such as product luminescence performance and thermal stability adjustable by connecting different groups, make the derivative an ideal choice for the organic light-emitting layer material of the organic electroluminescent device. The light-emitting layer of the OLED device using the fluorescent material has high fluorescence efficiency and good stability, so that the light-emitting efficiency and the service life of the device can reach the practical requirements.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence. More specifically, it involves derivatives, including the Derivative materials and organic electroluminescent devices. 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 and surface light sources...

Claims

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Application Information

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IPC IPC(8): C07C15/38C07C15/20C07C211/61C07C211/54C07C13/66C07C13/72C07D307/91C07D307/79C07C43/275C07C317/14C07D407/10C07D311/82C07D213/06C07D251/24C07D405/10C07D213/16C07D263/57C07D209/86C07D235/08C07D307/81C07D215/04C07D401/10C07D471/04C07D333/48C07D333/08C07D311/96C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C13/66C07C13/72C07C15/20C07C15/38C07C43/275C07C211/54C07C211/61C07C317/14C07D209/86C07D213/06C07D213/16C07D215/04C07D235/08C07D251/24C07D263/57C07D307/79C07D307/81C07D307/91C07D311/82C07D311/96C07D333/08C07D333/48C07D401/10C07D405/10C07D407/10C07D471/04C07C2603/97C07C2603/54C07C2603/24C07C2603/50C07C2603/26C07C2603/20C07C2603/48C07C2603/18C07B2200/05C09K2211/1059C09K2211/1044C09K2211/1033C09K2211/1029C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1092C09K2211/1088H10K85/622H10K85/624H10K85/633H10K85/655H10K85/631H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/11
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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