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Conjugated polymers and their use in optoelectronic devices

A technology of copolymerization and devices, applied in the field of conjugated polymers and their use in optoelectronic devices

Inactive Publication Date: 2012-05-30
POLYERA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, P3HT / PCBM-based solar cells have several fundamental limitations

Method used

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  • Conjugated polymers and their use in optoelectronic devices
  • Conjugated polymers and their use in optoelectronic devices
  • Conjugated polymers and their use in optoelectronic devices

Examples

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[0186] In one aspect, the present invention relates to a method for the synthesis of oligomeric or polymeric compounds comprising repeating units of formula I, Ia or Ib in their backbone. Generally, an oligomeric or polymeric compound of the invention can be prepared having the following repeating units:

[0187]

[0188] The oligomeric or polymeric compounds are prepared in part from the following starting compounds:

[0189]

[0190] The starting compound is then functionalized to contain (a) the solubilizing group R a (eg by alkylation) and / or (b) a polymerizable group capable of self-polymerization or copolymerization with one or more other units. Such self-polymerization and copolymerization can be achieved by various polymerization systems, including metal-catalyzed coupling reactions well known to those skilled in the art, such as Stille coupling, Suzuki coupling, Negishi coupling, Kumada coupling and Yamamoto coupling. For example, the polymerizable group may b...

Embodiment 1a

[0217] Example 1a: 3,6-Bis-thieno[3,2-b]thien-2-yl-2,5-dihydro-pyrrolo Preparation of [3,4-c]pyrrole-1,4-dione

[0218] Step 1: Preparation of 3a,6a-dihydro-thieno[3,2-b]thiophene-2-carboxylic acid amide

[0219]

[0220]Heating 3a,6a-dihydro-thieno[3,2-b]thiophene-2-carboxylic acid 1 (5.0g, 26.8mmol, Fuller et al., J.Chem.Soc. (Journal of the Chemical Society), Perkin Trans 1, 3465-3470), dissolved in 50ml of thionyl chloride (SOCl 2 ) formed mixture, which was refluxed for 3 hours, and then the excess SOCl 2 Remove by rotary evaporator. Dichloromethane (125ml) was added and the resulting solution was added dropwise to NH2O in an ice / salt bath. 4 OH (150ml, 28-30%) was dissolved in a mixture formed by 200ml of dichloromethane, and the reaction temperature was kept below -5°C. A white precipitate formed immediately. The mixture was stirred for 20 minutes. The precipitate was collected by vacuum filtration and washed three times with water, and weighed after vacu...

Embodiment 1b

[0227] Example 1b: 2,5-bis-(2-butyl-octyl)-3,6-bis-thieno[3,2-b]thiophene-2- Preparation of yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione

[0228]

[0229] 3,6-bis-thieno[3,2-b]thiophen-2-yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 4 (1.2g, 2.9mmol), 5-iodomethyl-undecane (2.59g, 8.7mmol), Cs 2 CO 3 (3.13g, 9.6mmol) was injected into a 100ml flask, then argon was bubbled in for 10 minutes, followed by the addition of 50ml of dimethylformamide (DMF). The resulting mixture was heated at 60°C for 36 hours and then cooled to room temperature. Add 50ml of chloroform. The organic layer was washed with water (50ml×3), then washed with anhydrous Na 2 SO 4 dry. The solvent was removed and a precipitate formed from methanol to give a black solid. The product was purified by column chromatography using chloroform / hexane mixture (1:1 v / v) as eluent and weighed after drying to obtain 0.78 g (yield 36%). 1 H NMR (CDCl 3 , 500MHz): δ9.28(s, 2H), 7.61(d, 2H, J=5.5), 7.30(d...

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Abstract

Disclosed are certain oligomeric and polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and / or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The disclosed compounds can provide high power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on / off current ratios, and / or air stability when used in photovoltaic cells or transistors. The disclosed compounds can have good solubility in common solvents enabling device fabrication via solution processes.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to and the benefit of U.S. Provisional Patent Application US61 / 180,256, filed May 21, 2009, and U.S. Provisional Patent Application US61 / 323,152, filed April 12, 2010, the disclosures of both of these U.S. Provisional Patent Applications All are incorporated herein by reference in their entirety. Background technique [0003] A new generation of optoelectronic devices, such as organic photovoltaics (OPV) and organic light-emitting transistors (OLET), are fabricated using organic semiconductors as their active components. To be commercially meaningful, such organic semiconductor-based devices should be cost-effectively processable. [0004] Bulk heterojunction (BHJ) solar cells are generally considered to be the most promising OPV structures because they can be fabricated using roll-to-roll and mass production methods. BHJ solar cells comprise a photoactive layer disposed between an ano...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01B1/12H01L51/00H10N10/856
CPCC08G61/125B82Y10/00H01L51/5012H01L51/0036H01L51/0545H01L51/0047H01L51/5048C08G2261/91C08G2261/3243C08G2261/122C08G2261/3246H01L51/0037H01L51/0043C08G2261/3223C08G61/126H01L51/4253C08G2261/92Y02E10/549H10K85/113H10K85/1135H10K85/151H10K85/215H10K10/466H10K30/30H10K50/14H10K50/11H10K30/50C08G61/12C08L65/00H01B1/12H10K85/111
Inventor 潘华龙颜河姚彦吕少峰朱正国安东尼欧·菲奇提
Owner POLYERA CORP
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