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(12) United States Patent (10) Patent No.: US 8,298,686 B2 Uetani (45) Date of Patent: Oct US008298686B2 (12) United States Patent (10) Patent No.: US 8,298,686 B2 Uetani (45) Date of Patent: Oct. 30, 2012 (54) COMPOSITION AND ORGANIC JP 2008-266459 A 11, 2008 PHOTOELECTRC CONVERTER USING THE WO 2008/O16091 A1 2/2008 SAME WO 2008/044585 A1 4, 2008 WO 2008/093822 A1 8/2008 (75) Inventor: Yasunori Uetani, Tsukuba (JP) WO 2008/0938.23 A1 8/2008 WO 2008/093831 A1 8/2008 (73) Assignee: Sumitomo Chemical Company, Limited, Tokyo (JP) OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this Youngkyoo Kim, et al., Organic Photovoltaic Devices Based on patent is extended or adjusted under 35 Blends of Regioregular Poly(3-hexylthiophene) and Poly(9.9- U.S.C. 154(b) by 124 days. dioctylfluorene-co-benzothiadiazole), Chemistry of Materials, vol. 16, No. 3, Nov. 1, 2004, pp. 4812-4818. (21) Appl. No.: 12/867,799 O. Inganäs, et al., "Low bandgap alternating polyfluorene copoly (22) PCT Filed: Feb. 17, 2009 mers in plastic photodiodes and Solar cells'. Applied Physics A: Materials Science & Processing, vol. 79, No. 1, Jun. 1, 2004, pp. (86). PCT No.: PCT/UP2009/053126 31-35. S371 (c)(1), Extended European Search Report issued Mar. 29, 2012 in European (2), (4) Date: Aug. 16, 2010 Patent Application No. 09713439.9. Christopher R. McNeill, et al., “Dual electron donor/electron accep (87) PCT Pub. No.: WO2009/104781 tor character of a conjugated polymer in efficient photovoltaic PCT Pub. Date: Aug. 27, 2009 diodes'. Applied Physics Letters, vol. 90, No. 19, May 9, 2007, pp. 193506-1-193506-3. (65) Prior Publication Data * cited by examiner US 2010/032.7271 A1 Dec. 30, 2010 Primary Examiner —Nathan Ha (30) Foreign Application Priority Data (74) Attorney, Agent, or Firm — Sughrue Mion, PLLC Feb. 18, 2008 (JP) ................................. 2008-035579 (57) ABSTRACT Mar. 3, 2008 (JP) ................................. 2008-051810 An organic photoelectric converter having excellent photo Aug. 22, 2008 (JP) ................................. 2008-213692 electric conversion efficiency can be produced by using a composition containing a polymer compound A having a (51) Int. Cl. repeating unit represented by formula (1) and a polymer HOIL 5/54 (2006.01) compound B having a repeating unit represented by formula (52) U.S. Cl. .......................................... 428/690; 257/40 (2): (58) Field of Classification Search .................... 257/40; 428/690-693, 917 (1) See application file for complete search history. (56) References Cited U.S. PATENT DOCUMENTS 6,353,083 B1 3/2002 Inbasekaran et al. 7,037.599 B2 * 5/2006 Culligan et al. .............. 428,690 7,112,649 B2 * 9/2006 Liu et al. ....................... 528,373 7,180,110 B2 2/2007 Komatsu et al. 7,605,225 B2 * 10/2009 Marks et al. .................. 528/377 wherein R' and R respectively represent a hydrogenatom, a 7,893,160 B2 * 2/2011 Inbasekaran et al. ......... 525, 191 fluorine atom, an alkyl group, an alkoxy group, an alkylthio 7.910,684 B2 * 3/2011 Li ................................. 528,163 group, an aryl group, an aryloxy group, an arylthio group, an 8,039,121 B2 * 10/2011 Iwakuma et al. ............. 428,690 arylalkyl group, an arylalkoxy group or an arylalkylthio 2003, OO64174 A1 4/2003 Miteva et al. 2003/0066950 A1 4/2003 Halls et al. grOup, 2004/O115473 A1 6/2004 Burroughes et al. 2006/0174937 A1 8, 2006 Zhou (2) 2008.0003422 A1 1/2008 Ueda 2010,000 1263 A1 1/2010 Noguchi et al. 2010, 0006154 A1 1/2010 Kitazawa et al. 2010.0033085 A1 2/2010 Nakatani et al. 2010, 0096.980 A1 4/2010 Nakatani et al. 2010, 0108993 A1 5, 2010 Moriwaki et al. FOREIGN PATENT DOCUMENTS wherein RandR' respectively represent a hydrogenatom, a JP 2002-536492 A 10, 2002 fluorine atom, an alkyl group, an alkoxy group, an alkylthio JP 2003-176420 A 6, 2003 group, an aryl group, an aryloxy group, an arylthio group, an JP 2004-534863. A 11, 2004 JP 2004-3629.10 A 12, 2004 arylalkyl group, an arylalkoxy group or an arylalkylthio JP 2006-063334 A 3, 2006 group, and p represents an integer of 2 to 10. JP 2006-222429 A 8, 2006 JP 2008-266.307 A 11, 2008 14 Claims, No Drawings US 8,298,686 B2 1. COMPOSITION AND ORGANIC PHOTOELECTRC CONVERTER USING THE (1) SAME CROSS REFERENCE TO RELATED APPLICATIONS This application is a National Stage of International Appli cation No. PCT/JP2009/053126 filed Feb. 17, 2009, which claims priority from Japanese Patent Application Nos. 2008 10 wherein R' and Reach independently represent a hydrogen 035579, 2008-051810 and 2008-213692, filed on Feb. 18, atom, a fluorine atom, an alkyl group, an alkoxy group, an 2008, Mar. 3, 2008 and Aug. 22, 2008, respectively, the con alkylthio group, an aryl group, an aryloxy group, an arylthio tents of all of which are incorporated herein by reference in group, an arylalkyl group, an arylalkoxy group or an aryla their entirety. 15 lkylthio group, and the hydrogen atom contained in these groups may be substituted with a fluorine atom, and TECHNICAL FIELD (2) The present invention relates to a composition, and an organic photoelectric converter using the same. BACKGROUND ART Recently, the use of an organic semiconductor material as a material of an active layer of an organic photoelectric con 25 wherein RandR each independently represent a hydrogen Verter (organic Solar battery, optical sensor, etc.) has been atom, a fluorine atom, an alkyl group, an alkoxy group, an intensively studied. Since an active layer can be made by an alkylthio group, an aryl group, an aryloxy group, an arylthio inexpensive coating method when a polymer compound is group, an arylalkyl group, an arylalkoxy group or an aryla used as an organic semiconductor material, various polymer lkylthio group, and the hydrogen atom contained in these compounds and compositions containing the polymer com 30 groups may be substituted with a fluorine atom; p represents pounds have been studied. For example, it is described that a an integer of 2 to 10; a plurality of R's may be the same or composition including a fullerene derivative and a copolymer different; and a plurality of R's may be the same or different. containing a repeating unit (M) shown below and a repeating Second, the present invention provides an organic photo unit (N) shown below is used for an organic solar battery electric converter comprising an organic layer containing the (Applied Physics Letters Vol. 84, No. 10 1653-1655 (2004)). 35 composition of the present invention. Third, the present invention provides an organic photoelec tric converter comprising a pair of electrodes, at least one of which is transparent or translucent; a first organic layer con taining the composition of the present invention provided 40 between the electrodes; and a second organic layer containing OO an electron-donating compound provided adjacent to the first organic layer. Fourth, the present invention provides an organic photo Repeating unit (M) electric converter comprising a pair of electrodes, at least one 45 of which is transparent or translucent; a first organic layer S containing an electron-accepting compound provided between the electrodes; and a second organic layer containing the composition of the present invention provided adjacent to the first organic layer. 50 Fifth, the present invention provides an organic photoelec tric converter comprising a pair of electrodes, at least one of Repeating unit (N) which is transparent or translucent; and an organic layer containing the composition of the present invention and an electron-donating compound provided between the elec DISCLOSURE OF THE INVENTION 55 trodes. Sixth, the present invention provides an organic photoelec However, an organic photoelectric converter using the tric converter comprising a pair of electrodes, at least one of composition, Such as an organic Solar battery, was not neces which is transparent or translucent; and an organic layer sarily sufficient in photoelectric conversion efficiency. containing an electron-accepting compound and the compo An object of the present invention is to provide a compo 60 sition of the present invention provided between the elec sition which can impart excellent photoelectric conversion trodes. efficiency to an organic photoelectric converter when used in the production of the converter. MODE FOR CARRYING OUT THE INVENTION First, the present invention provides a composition com prising a polymer compound A containing a repeating unit 65 The present invention will be described in detail below. represented by the formula (1) and a polymer compound B The composition of the present invention comprises a poly containing a repeating unit represented by the formula (2): mer compound A containing a repeating unit represented by US 8,298,686 B2 3 4 the formula (1) and a polymer compound B containing a 20 carbonatoms or a cycloalkyl group having 1 to 20 carbon repeating unit represented by the formula (2). atoms in a structure thereof, and a group represented by the <Polymer Compound Ad formula (15). In the polymer compound A used in the present invention, R" and R in the formula (1) each independently represent a (15) hydrogen atom, a fluorine atom, an alkyl group, an alkoxy In the formula (15), g represents an integer of 1 to 6, and h group, an alkylthio group, an aryl group, an aryloxy group, an represents an integer of 0 to 5. arylthio group, an arylalkyl group, an arylalkoxy group or an Examples of the aryl group include a phenyl group, a arylalkylthio group, and the hydrogen atom contained in 10 C-C alkoxyphenyl group (C-C means that the number these groups may be substituted with a fluorine atom. of carbon atoms is from 1 to 12, the same shall apply herein In the formula (1), the alkyl group represented by RandR after), a C-C alkylphenyl group, a 1-naphthyl group, a may be linear or branched, or a cycloalkyl group.
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