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Benzotriazolyl-containing copolymer, preparation method and organic electroluminescent devices thereof

A benzotriazole-based and copolymer technology, which is applied in electric solid devices, light-emitting materials, electrical components, etc., can solve the problems of narrow doping concentration range, difficult device preparation, low luminous efficiency, etc., and achieve stable luminous performance, The effect of reducing the manufacturing cost and simplifying the synthesis process

Inactive Publication Date: 2012-11-21
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the doping concentration is high, these doped red light-emitting materials are easily aggregated on the solid film, which usually leads to fluorescence quenching; when the doping concentration is low, the energy transfer cannot be completely from the host material to the red In light-emitting materials, this usually results in low purity of light emission from the device
As a result, the optimal doping concentration is usually low and the effective doping concentration range is narrow, resulting in low luminous efficiency and difficult device fabrication

Method used

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  • Benzotriazolyl-containing copolymer, preparation method and organic electroluminescent devices thereof
  • Benzotriazolyl-containing copolymer, preparation method and organic electroluminescent devices thereof
  • Benzotriazolyl-containing copolymer, preparation method and organic electroluminescent devices thereof

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preparation example Construction

[0023] Another object of the present invention is to provide a method for preparing a benzotriazole-based copolymer, such as figure 1 shown, including the following steps:

[0024] Step S1, providing compounds A and B represented by the following structural formula,

[0025]

[0026] Among them, R 1 for C 1 ~C 20 the alkyl group, R 2 for C 1 ~C 20 Alkyl; preferably, R 1 for C 8 ~C 16 the alkyl group, R 2 for C 6 ~C 12 the alkyl group;

[0027] Step S2, under an oxygen-free environment (consisting of nitrogen or inert gas), compound A and B are added in the organic solvent containing catalyst, carry out Stille coupling reaction 12~48h at 90~120 ℃, obtain following structural formula (I ) said benzotriazole-based copolymer represented by:

[0028]

[0029] In the formula, n is an integer of 10-100.

[0030] The benzotriazole-based copolymer prepared above also contains a lot of impurities, and it needs to be purified, that is, the preparation method also inc...

Embodiment 1

[0041] The benzotriazole-based copolymer of the present embodiment is poly{4,8-bis(2-ethylhexyloxy)-benzodithiophene-2-dodecylbenzotriazole}, wherein, R 1 is 2-ethylhexyl, R 2 Be dodecyl, n=63; The structural formula of this copolymer is as follows:

[0042]

[0043] The preparation steps of above-mentioned polymer are as follows:

[0044] The preparation of step 1, 2-n-dodecylbenzotriazole, reaction formula is as follows:

[0045]

[0046] The specific process is as follows: 1,2,3-benzotriazole (5.0g, 42mmol), potassium hydroxide (5.6g, 100mmol) and dodecane bromide (12.2g, 49mmol) were dissolved in 50mL of methanol, Heat to reflux for 24 hours; stop stirring after cooling to room temperature, and remove the solvent by rotary evaporation.

[0047] The crude product was separated by silica gel column chromatography using petroleum ether as the eluent to obtain a colorless oily substance, namely 2-dodecylbenzotriazole, with a yield of 31%.

[0048] 1 H NMR (400MHz, CD...

Embodiment 2

[0060] The benzotriazole-based copolymer of the present embodiment is poly{4,8-bis(dodecyloxy)-benzodithiophene-2-hexylbenzotriazole}; wherein, R 1 for dodecyl, R 2 Be hexane group, n=65; The structural formula of this copolymer is as follows:

[0061]

[0062] The preparation steps of above-mentioned polymer are as follows:

[0063] Step 1, the difference with step 1 in Example 1 is: replace bromododecane with hexyl bromide, and other steps are all the same;

[0064] Step 2 is the same as Step 2 in Example 1;

[0065] Step 3, the preparation of poly{4,8-bis(dodecyloxy)-benzodithiophene-2-hexylbenzotriazole}, the reaction formula is as follows:

[0066]

[0067] Under the protection of argon, 2,6-ditrimethyltin-4,8-bis(dodecyloxy)-benzodithiophene (265.8 mg, 0.3 mmol), 2-n-hexyl-4,7-bis Bromo-benzotriazole (107.7mg, 0.3mmol) and 10mL N,N-dimethylformamide were respectively added to a 50mL two-necked bottle, and after argon was fully exhausted for about 20min, 15mg di...

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Abstract

The present invention belongs to the technical field of organic photoelectric materials, and discloses a benzotriazolyl-containing copolymer, a preparation method and an application thereof. The benzotriazolyl-containing copolymer has the following general formula (I), wherein R1 and R2 are respectively C1-C20 alkyl, and n is an integer of 10-100. The benzotriazolyl-containing copolymer of the present invention has the following advantages that: a synthesis process is simple, manufacturing cost is reduced, and mass production of the benzotriazolyl-containing copolymer can be achieved; and electroluminescent devices of the benzotriazolyl-containing copolymer have characteristics of high purity and stable luminescence performance, and can be used as red-light emitting polymers.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a benzotriazole-based copolymer used as an organic semiconductor material, a preparation method and application thereof. The invention also relates to an organic electroluminescent device using the benzotriazole-based copolymer as a light-emitting layer. Background technique [0002] In 1990, J.H.Burroughes of the University of Cambridge in the United Kingdom introduced PPV polymer light-emitting diodes for the first time, pioneering the preparation of devices by solution processing, and foreseeing the possibility of using them as flexible displays. The successful development of polymer light-emitting diodes has confirmed the feasibility of this technology and made people see the hope of using this technology as a flat panel display or a large-area flexible display screen. As we all know, it is very necessary for electroluminescent materials to emit high-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54H01L51/50
Inventor 周明杰王平张振华张娟娟
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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