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D-A type conjugated polymer containing condensed ring lactone, and preparation method and application thereof

A conjugated polymer, D-A technology, applied in the field of electrochemical materials, can solve problems such as affecting photoelectric performance, increasing steric hindrance, and not being able to fully utilize the value of ester groups

Active Publication Date: 2019-11-05
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although D-A conjugated polymers containing ester groups have achieved excellent results in the construction of donor materials, due to the increased steric hindrance of donor materials based on ester groups, their preparation as donor materials has been greatly affected. The optoelectronic performance of the device structure does not give full play to the value of the ester group in the donor material

Method used

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  • D-A type conjugated polymer containing condensed ring lactone, and preparation method and application thereof
  • D-A type conjugated polymer containing condensed ring lactone, and preparation method and application thereof
  • D-A type conjugated polymer containing condensed ring lactone, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Synthesis of D-A Conjugated Polymer P1 Containing Fused Lactone

[0139] The synthetic route is:

[0140]

[0141] (1) Synthesis of intermediate B1

[0142] Add 5H-dithieno[3,2-B:2',3'-D]pyran-5-one (150mg), N-bromosuccinimide (NBS) (746mg ), chloroform (10mL) and N,N-dimethylformamide (DMF) (5mL), react at room temperature in the dark for 48h. The chloroform was removed by rotary evaporation under reduced pressure, and the crude product was purified by column chromatography, using a mixed solvent of dichloromethane and sherwood oil with a volume ratio of 1:2 as an eluent to obtain a white solid product B1 (214mg, yield 81% ).

[0143] NMR and MS data of intermediate B1: 1 H NMR (CDCl 3 ,400MHz,δ / ppm):7.57(s,1H),7.11(s,1H). 13 C NMR (CDCl 3 ,100MHz,δ / ppm):155.88,151.39,145.40,128.86,122.33,121.11,115.71,113.67,111.97.Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS)(m / z):366.04(M + ).

[0144] (2) Synthesis of interm...

Embodiment 2

[0155] Synthesis of D-A Conjugated Polymer P2 Containing Fused Lactone

[0156] The synthetic route is:

[0157]

[0158] Steps (1), (2) and (3) of this embodiment are the same as in Embodiment 1.

[0159] (4) Synthesis of D-A type conjugated polymer P1 containing fused ring lactone

[0160] Add D1 (64 mg), (4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5 -b']dithiophene-2,6-diyl)bis(trimethylstannane) (compound E1) (70mg), Pd 2 (dba) 3 (2.72mg) and P(o-Tol) 3 (7.24mg), reacted at 110°C for 24h under the protection of nitrogen. After cooling to room temperature, the reaction solution was added dropwise to 150 mL of methanol for chromatography, and the precipitate was filtered to obtain the crude product, which was transferred to a Soxhlet extractor, extracted with n-hexane, dichloromethane and chloroform in sequence, and concentrated Finally, the obtained chloroform extract was obtained, which was dropped into methanol for further chromatography, and fi...

Embodiment 3

[0164] Synthesis of D-A Conjugated Polymer P3 Containing Fused Lactone

[0165] The synthetic route is:

[0166]

[0167](1) Synthesis of Intermediate B3

[0168] Add 2,7-dibromo-9-fluorenone (501.4mg), sodium perborate monohydrate (2961.2mg) and trifluoroacetic acid (40mL) sequentially into a 200mL Schlenck tube, and react in the dark at 68°C for 12 hours under nitrogen protection . The trifluoroacetic acid was removed by rotary evaporation under reduced pressure, and the crude product was purified by column chromatography, using a mixed solvent of dichloromethane and sherwood oil with a volume ratio of 2:1 as an eluent to obtain a white solid product B3 (446mg, yield 85%). Intermediate B3 mass spectrometry data: MALDI-TOF MS (m / z): 354.0 (M + ).

[0169] (2) Synthesis of intermediate C3

[0170] Intermediate B3 (113 mg), (4-(2-butyloctyl)thiophene-2-trimethyltin reagent (397.5 mg), Pd(PPh 3 ) 4 (29.5mg) and toluene (10ml), refluxed overnight under nitrogen protect...

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Abstract

The invention provides a D-A type conjugated polymer containing a condensed ring lactone, and a preparation method and an application thereof. The structural formula of the D-A type conjugated polymercontaining the condensed ring lactone is represented by formula I. The condensed ring lactone group is introduced to the conjugated main chain of a polymer, so the molecular conjugate plane of the polymer is widened, the intermolecular pi-pi stacking interaction is promoted, and the intermolecular steric hindrance of the polymer is reduced. The D-A type conjugated polymer containing the condensedring lactone has the advantages of good solubility, good photoelectric properties, excellent light absorption and carrier transport performances, and realization of a high short circuit current and ahigh energy conversion efficiency in organic solar batteries.

Description

technical field [0001] The invention belongs to the field of electrochemical materials, and relates to a D-A type conjugated polymer containing fused ring lactone, a preparation method and application thereof. Background technique [0002] Organic solar cells, which use organic conjugated molecules as active materials, have many advantages such as light weight, flexibility, wide source of raw materials, solution processing and large-scale preparation, etc., and have become one of the focuses of global academic and industrial circles in recent years. The development and continuous progress of conjugated molecular materials is the driving force for the performance improvement of organic solar cells. At present, many types of organic conjugated compounds, including conjugated polymers, conjugated small molecules, and fullerenes, have been applied to the active layer of the battery. In recent years, among many materials, D-A conjugated polymer donor materials containing ester gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/145C08G2261/18C08G2261/3243C08G2261/3223C08G2261/3247C08G2261/146C08G2261/414C08G2261/91H10K85/151H10K85/113H10K30/00Y02E10/549
Inventor 丁黎明肖作
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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