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Conjugated polymers

A polymer, acceptor unit technology, applied in conductive materials, conductive materials, conductors, etc.

Active Publication Date: 2016-02-10
RAYNERGY TEK INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the polymers disclosed in the prior art for use in OPV or OPD devices still leave room for further improvement, such as lower bandgap, better processability (especially from solution), more High OPV cell efficiency and higher stability

Method used

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  • Conjugated polymers
  • Conjugated polymers
  • Conjugated polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0420] Example 1 - Polymer 1

[0421]

[0422] to 20cm 3 Add 2,6-dibromo-benzo[1,2-b; 4,5-b']dithiophene-4,8-dicarboxylate bis-dodecyl ester (309.1 mg; 0.4000 mg mol; 1.000 equiv), 2,5-bis-trimethylstannyl-thiophene (327.8 mg; 0.8000 mmol; 2.000 equiv), 4,7-dibromo-5,6-bis-octyloxy-benzene And[1,2,5]thiadiazole (165.1mg; 0.3000mmol; 0.7500eq), 4,8-dibromo-6-(2-ethyl-hexyl)-[1,2,5]thiadiazole Azolo[3,4-e]isoindole-5,7-dione (47.5mg; 0.100mmol; 0.250eq), tris(dibenzylideneacetone)dipalladium(0) (14.7mg; 0.0160mM mol; 0.0400 eq) and tri-o-tolyl-phosphine (19.5 mg; 0.0640 mmol; 0.160 eq). The vessel was emptied and purged three times with nitrogen, and degassed chlorobenzene (5.00 cm 3 ), and the reaction mixture was further degassed for 5 minutes. The reaction mixture was heated sequentially at 140°C (60 sec), 160°C (60 sec) and 170°C (1800 sec) in a microwave reactor (Initator, Biotage). Immediately after the completion of the polymerization, the reaction mixture was ...

Embodiment 2

[0423] Example 2 - Polymer 2

[0424]

[0425] to 5cm 3 Add 2,6-dibromo-benzo[1,2-b; 4,5-b']dithiophene-4,8-dicarboxylate bis-dodecyl ester (193.2 mg; 0.2500 mg mol; 1.000 equiv), 2,5-bis-trimethylstannyl-thiophene (204.9 mg; 0.5000 mmol; 2.000 equiv), 4,8-dibromo-6-(2-ethyl-hexyl)- [1,2,5]thiadiazolo[3,4-e]isoindole-5,7-dione (118.8 mg; 0.2500 mmol; 1.000 equiv), tris(dibenzylideneacetone)dipalladium (0) (9.2 mg; 0.0100 mmol; 0.040 equiv) and tri-o-tolyl-phosphine (12.2 mg; 0.0400 mmol; 0.160 equiv). The vessel was emptied and purged three times with nitrogen, and degassed chlorobenzene (2.1 cm 3 ), and the reaction mixture was further degassed for 5 minutes. The reaction mixture was heated sequentially at 140 °C (60 sec), 160 °C (60 sec) and 175 °C (1800 sec) in a microwave reactor (Initator, Biotage). Immediately after completion of the reaction, the reaction mixture was cooled to 65 °C and precipitated into stirred methanol (100 cm 3 )middle. The polymer was co...

Embodiment 3

[0426] Example 3 - Polymer 3

[0427]

[0428] to 5cm 3 Add 1,4-bis-(5-bromo-7,7-bis-(2-ethyl-hexyl)-7H-3,4-dithia-7-sila-cyclopenta[a ]cyclopentadien-2-yl)-2,3,5,6-tetrafluorobenzene (285.3 mg; 0.2500 mmol; 1.000 equivalents), 2,5-bis-trimethylstannyl-thiophene (204.9 mg; 0.5000 mmol; 2.000 equiv), 4,8-dibromo-6-(2-ethyl-hexyl)-[1,2,5]thiadiazolo[3,4-e]isoindole- 5,7-Diketone (118.8mg; 0.2500mmol; 1.000eq), tris(dibenzylideneacetone)dipalladium(0) (9.2mg; 0.0100mmol; 0.040eq) and tris-o-tolyl- Phosphine (12.2 mg; 0.0400 mmol; 0.160 equiv). The vessel was emptied and purged three times with nitrogen, and degassed chlorobenzene (2.1 cm 3), and the reaction mixture was further degassed for 5 minutes. The reaction mixture was heated sequentially at 140 °C (60 sec), 160 °C (60 sec) and 175 °C (1800 sec) in a microwave reactor (Initator, Biotage). Immediately after completion of the reaction, the reaction mixture was cooled to 65 °C and precipitated into stirred methanol...

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Abstract

The invention relates to novel conjugated polymers containing one or more [1,2,5]Thiadiazolo[3,4-e]isoindole-5,7-dione (TID) repeating units, to methods for their preparation and educts or intermediates used therein, to polymer blends, mixtures and formulations containing them, to the use of the polymers, polymer blends, mixtures and formulations as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these polymers, polymer blends, mixtures or formulations.

Description

technical field [0001] The present invention relates to novel conjugated polymers comprising one or more [1,2,5]thiadiazolo[3,4-e]isoindole-5,7-dione (TID) repeating units, the preparation of which Process and educts or intermediates used therein, polymer blends, mixtures and formulations comprising them, polymers, polymer blends, mixtures and formulations as organic semiconductors in or for the preparation of organic electronics (OE ) devices, especially organic photovoltaic (photovoltaic) (OPV) devices and organic photodetectors (OPD), and OEs, OPVs, and OEs, OPVs, and OPD devices. Background technique [0002] In recent years, organic semiconductor (OSC) materials have been developed to yield more versatile lower-cost electronic devices. Such materials are used in a variety of devices or devices, including organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs), organic photodetectors (OPDs), organic photovoltaic (OPV) cells, sensors, to name a f...

Claims

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Application Information

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IPC IPC(8): C09K11/00C08G61/12H01B1/00H01L51/00
CPCH01B1/127H01B1/128C08G61/123C08G61/124C08G61/126C08G2261/1412C08G2261/1424C08G2261/149C08G2261/3223C08G2261/3243C08G2261/344C08G2261/364C08G2261/411C08G2261/91Y02E10/549H10K85/111H10K85/215H10K85/113H10K85/151H10K30/20H10K50/171H10K30/50H10K30/30C08G61/12C09K11/00H01B1/00H10K85/40H10K10/23H10K10/484H10K50/11H10K50/15H10K50/16H10K50/17H10K50/18C08G2261/12C08G2261/1426C08G2261/18C08G2261/3246
Inventor N·布劳因A·普罗恩G·莫斯L·南森M·克罗姆皮克S·贝尔尼
Owner RAYNERGY TEK INC
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