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D (A-Ar) 2 type organic photoelectric compound based on carbazole eleven-membered fused ring planar nucleus and a preparation method and application thereof

A compound, carbazole technology, applied in the field of organic optoelectronics, can solve the problems of low carrier mobility, narrow absorption spectrum, low efficiency, etc., and achieve the effects of wide ultraviolet absorption, high batch repeatability, and molecular weight determination

Active Publication Date: 2019-07-05
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, based on organic small molecule solar cell materials, there are still scientific problems such as narrow absorption spectrum, low carrier mobility, low efficiency and poor stability, so it is necessary to develop new high-performance small molecule donor materials

Method used

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  • D (A-Ar) 2 type organic photoelectric compound based on carbazole eleven-membered fused ring planar nucleus and a preparation method and application thereof
  • D (A-Ar) 2 type organic photoelectric compound based on carbazole eleven-membered fused ring planar nucleus and a preparation method and application thereof
  • D (A-Ar) 2 type organic photoelectric compound based on carbazole eleven-membered fused ring planar nucleus and a preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] D(A-Ar) based on 11-membered fused ring core of carbazole 2 The synthetic route of the intermediates (DPP-Cz, Br-DPP-Cz, DPP-Th, Br-DPP-Th, DPP-ST, Br-DPP-ST) of the linear small molecules of organic optoelectronic compounds is shown in the figure below.

[0089]

[0090] 1.1, 2,5-bis-(2-hexyldecyl)-3-(5-(9-octylcarbazol-3-yl)thiophen-2-yl)-6-(thiophen-2-yl) Synthesis of pyrrolo[3,4-c]pyrrole-1,4-dione (DPP-Cz)

[0091] Add 2,5-bis(2-hexyldecyl)-3-(5-bromothiophen-2-yl)-6-(thiophen-2-yl)pyrrolo[3,4 -c] pyrrole-1,4-dione (Br-DPP) (0.50 g, 0.60 mmol), 30 mL of toluene, tetrakis (triphenylphosphine) palladium (Pd (PP 3 ) 4 , 35mg, 0.03mmol), 9-octyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-carbazole (267mg, 0.66 mmol), potassium carbonate solution (2M, 3mL) and Aliquant 336 (4 drops). Reflux for 24 hours, cool down, extract with 3×25mL chloroform, combine the organic phases, wash with 3×40mL saturated brine, dry the organic phase with anhydrous magnesium sul...

Embodiment 2

[0103] Based on D(A-Ar) 2 TBTDBC-[Sn(CH 3 ) 3 ] 2 The synthetic route of is shown in the figure below.

[0104]

[0105] 2.1 Synthesis of 2,7-dibromo-3,6-diiodo-9-(2-octyldodecyl)carbazole (M1)

[0106] In a 100mL three-necked flask, add 2,7-dibromo-carbazole (3g, 4.97mmol) and 50mL acetic acid successively, pass nitrogen for deoxygenation replacement three times, stir magnetically, dissolve the reactants at 80°C, and quickly weigh potassium iodide (2.22 g, 13.41mmol) and potassium periodate (1.43g, 6.71mmol), and sequentially added to the reaction system, reflux for 12h. After the reaction was complete, it was cooled to room temperature, and the mixture was quenched by pouring into 100 mL of water, and extracted with chloroform (100 mL×3) and washed with saturated sodium sulfite solution (100 mL×3). Combine the organic phases and wash with anhydrous MgSO 4 Dry overnight, filter, and spin off the solvent under reduced pressure to give a gray crude product. The concen...

Embodiment 3

[0116] D(A-Ar) based on 11-membered fused ring core of carbazole 2 Type target compound TBTDBC(DPP) 2 , TBTDBC (DPP-Cz) 2 , TBTDBC (DPP-Th) 2 and TBTDBC (DPP-ST) 2 The synthetic route of is shown in the figure below.

[0117]

[0118] where Ar is:

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Abstract

The invention relates to a D (A-Ar) 2 type organic photoelectric compound based on carbazole eleven-membered fused ring planar nucleus and a preparation method and application thereof. The preparationmethod comprises the steps that ternary carbazole central ring units are coupled with thiophene and benzothiophene derivatives through ring closing reaction and coupling reaction to obtain derivatives of a carbazole group-containing eleven-membered fused ring conjugated planar structure aromatic compound and D (A-Ar) 2 type linear organic small molecule photovoltaic material containing carbazolemulti-membered fused ring central nucleus. The derivatives of the eleven-membered large fused ring conjugated planar structure compound and the corresponding D (A-Ar) 2 type linear organic small molecule photovoltaic material have high thermal stability and high hole mobility. Through the development and application of the materials, high-efficiency organic solar cells, organic electroluminescentdiodes, organic field effect transistors and organic near-infrared photoelectric detector materials are obtained.

Description

technical field [0001] The present invention specifically relates to a molecular backbone donor core comprising a carbazole eleven-membered fused ring planar core D(A-Ar) 2 The linear small molecule material can be applied in the field of organic optoelectronic technology. Background technique [0002] Organic solar cells have become a research hotspot in the field of photovoltaics due to their advantages of low cost, light weight and large area preparation. [0003] As an organic small molecule donor material in the photosensitive active layer that absorbs sunlight and converts it into electrical energy, it has great potential due to its outstanding advantages such as simple purification, monodispersity, clear structure, easy modification and good batch reproducibility. market application prospects. Therefore, organic solar cells have attracted increasing attention. [0004] At present, organic small molecule solar cell materials still have scientific problems such as na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K11/06H01L51/00H01L51/46H10K99/00
CPCC07D519/00C09K11/06C09K2211/1092C09K2211/1029H10K85/655H10K85/657H10K85/6572Y02E10/549
Inventor 刘煜高辉山刘座吉朱卫国杨振
Owner CHANGZHOU UNIV
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