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(10) Patent No.: US 8.492,750 B2 Kohiro Et Al US00849275OB2 (12) United States Patent (10) Patent No.: US 8.492,750 B2 Kohiro et al. (45) Date of Patent: Jul. 23, 2013 (54) ORGANIC SEMICONDUCTOR (56) References Cited COMPOSITION, ORGANIC THIN FILMAND ORGANIC THIN FILMIELEMENT PROVIDED U.S. PATENT DOCUMENTS WITH ORGANIC THIN FILM 6,541,300 B1 4/2003 Chowdhuri et al. 2004/0038459 A1 2/2004 Brown et al. (75) Inventors: Kenji Kohiro, Tsukuba (JP); Shinichi 2004.006293.0 A1 4/2004 Roberts et al. 2005/00954.59 A1 5/2005 Chin et al. Yamate, Tsukuba (JP); Akiko 2005/O127354 A1 6/2005 Hanna et al. Nakazono, Tsukuba (JP) 2005/0156161 A1* 7/2005 Hanna et al. .................... 257/40 2006, O155040 A1 7/2006 Veres et al. (73) Assignee: Sumitomo Chemical Company, 2007. O158646 A1 7/2007 Reichmanis et al. Limited, Tokyo (JP) 2009/0001357 A1 1/2009 Takimiya et al. (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 GB 243.0546 A 3, 2007 U.S.C. 154(b) by 376 days. (Continued) (21) Appl. No.: 12/935,379 OTHER PUBLICATIONS “Solution-Processed Organic FET Using Low-Molecular Compound (22) PCT Filed: Mar. 24, 2009 (Solution-processed organic thin-film transistors based on Small mol PCT/P2009/055777 ecules)”, 54th Annual Academic Meeting of The Japan Society of (86). PCT No.: Applied Physics, 2007, 28a-W-10, with English translation. S371 (c)(1), B. Kosata et al., “Novel liquid crystals based on 1 benzothieno (2), (4) Date: Dec. 21, 2010 3.2-b1benzothiophene'. Liquid Crystals, vol.30, No. 5, 2003, pp. 603-610. (87) PCT Pub. No.: WO2009/122956 (Continued) PCT Pub. Date: Oct. 8, 2009 Primary Examiner — Anthony Ho (65) Prior Publication Data (74) Attorney, Agent, or Firm — Sughrue Mion, PLLC US 2011 FO108813 A1 May 12, 2011 (57) ABSTRACT (30) Foreign Application Priority Data An object of the present invention is to provide an organic semiconductor composition capable of forming an organic Mar. 31, 2008 (JP) ............................... P2008-0923O2 film having high carrier transportability. A preferable organic semiconductor composition contains a lower molecular (51) Int. Cl. weight compound and a higher molecular weight compound HOIL 35/24 (2006.01) having carrier transportability, and the solubility parameter of (52) U.S. Cl. the higher molecular weight compound and the Solubility USPC ..................................... 257/40; 257/E51.001 parameter of the lower molecular weight compound differ by (58) Field of Classification Search O6 to 15. USPC ............................................. 257/40, E51.001 See application file for complete search history. 10 Claims, 15 Drawing Sheets 3000 2 5 O O -500 O.OO O.50 1.00 1.50 2.00 2.50 3.00 3.50 ASP US 8,492,750 B2 Page 2 FOREIGN PATENT DOCUMENTS OTHER PUBLICATIONS JP 5-110069 A 4f1993 Shizuo Tokito et al., Control of Surfaces and Interfaces in Organic JP 2001-308415 A 11, 2001 Thin-FilmTransistors, NHK Science & Technical Research Labora JP 2004-006476 A 1, 2004 tories, Jan. 15, 2007, pp. 242-248, vol. 28, No. 5, Tokyo. JP 2004-158710 A 6, 2004 Extended European Search Report issued Apr. 11, 2012 in EP Patent JP 2006-514710 A 5, 2006 Application no. 09727837.8. WO O3,067667 A1 8, 2003 Office Action issued Mar. 13, 2013 in counterpart European Patent WO 2004/057688 A1 T 2004 Application No. 09727837.8. WO 2005/055 248 A2 6, 2005 WO 2007 100600 A2 9, 2007 * cited by examiner U.S. Patent Jul. 23, 2013 Sheet 1 of 15 US 8.492,750 B2 Fig.1 YZZZZZZZZZ Z3 <s 5 222222222 3 N. 1 U.S. Patent Jul. 23, 2013 Sheet 2 of 15 US 8.492,750 B2 Fig.2 YZZZZZZ73 -4 22%ZSSY)2, N U.S. Patent Jul. 23, 2013 Sheet 3 of 15 US 8.492,750 B2 Fig.3 3 N 1 U.S. Patent Jul. 23, 2013 Sheet 4 of 15 US 8.492,750 B2 Fig.4 2 5 2N, N N U.S. Patent Jul. 23, 2013 Sheet 5 Of 15 US 8.492,750 B2 Fig.5 6 2Z NYNNYNNNNN 2NZNZNZNNN NYNY ZZZZZZZZZZZZZZZ 2 N U.S. Patent Jul. 23, 2013 Sheet 6 of 15 US 8.492,750 B2 Fig.6 YZZZZZZZZZZZZZZZ 4 N U.S. Patent Jul. 23, 2013 Sheet 7 Of 15 US 8.492,750 B2 Fig. 7 N 1 U.S. Patent Jul. 23, 2013 Sheet 8 of 15 US 8.492,750 B2 Fig.8 NN-7bN %2 U.S. Patent Jul. 23, 2013 Sheet 9 Of 15 US 8.492,750 B2 Fig.9 %2 N U.S. Patent Jul. 23, 2013 Sheet 10 of 15 US 8.492,750 B2 Fig.10 NN-7b 2222222NNNNNNNNNNNNNN %2 N U.S. Patent Jul. 23, 2013 Sheet 11 of 15 US 8.492,750 B2 Fig.11 SN-7b N%22 U.S. Patent Jul. 23, 2013 Sheet 12 of 15 US 8.492.750 B2 3 W 4. U.S. Patent Jul. 23, 2013 Sheet 13 of 15 US 8.492.750 B2 -500 O.OO 0.50 100 1.50 2.00 2.50 3.00 3.50 ASP U.S. Patent Jul. 23, 2013 Sheet 14 of 15 US 8.492,750 B2 Fig.14 1-N 3 O O O 2500 2000 1500 1 OOO 500 O -500 0 1 0000 20000 30000 40000 50000 60000 70000 WEIGHT AVERAGE MOLECULAR WEIGHT (Mw) U.S. Patent Jul. 23, 2013 Sheet 15 of 15 US 8.492,750 B2 Fig.15 3000 2500 2000 1500 1000 500 O -500 0 1 0000 20000 30000 40000 50000 60000 70000 NUMBERAVERAGE MOLCULAR WEIGHT (Mn) US 8,492,750 B2 1. 2 ORGANIC SEMCONDUCTOR have increased, and even in a composition like that of the COMPOSITION, ORGANIC THIN FILMAND above-mentioned Patent Document 1, it is still difficult to ORGANIC THIN FILMIELEMENT PROVIDED obtain carrier transportability to a degree that is able to satisfy WITH ORGANIC THIN FILM Such requirements. CROSS REFERENCE TO RELATED On the other hand, the organic semiconductor thin film of APPLICATIONS Patent Document 2 is composed of crystal grains of a crys talline, low molecular weight organic semiconductor com This application is a National Stage of International Appli pound and an organic semiconductor component interposed cation No. PCT/JP2009/055777, filed on Mar. 24, 2009, in gaps between the crystal grains. However, the inventors of which claims priority from Japanese Patent Application No. the present invention found that in this thin film, the crystal 2008-092302, filed on Mar. 31, 2008, the contents of all of grains and the organic semiconductor component are not which are incorporated herein by reference in their entirety. always connected satisfactorily. Even if the crystal grains and organic semiconductor component appear to be connected, TECHNICAL FIELD 15 high carrier transportability cannot be obtained if they have The present invention relates to an organic semiconductor poor wettability or unable to satisfactorily carry out exchange composition, an organic film that uses the same, and an of charge. In addition, in the formation method of a thin film organic film element, organic film transistor, organic elec described in Patent Document 2, in addition to apply a coating troluminescence element, electronic tag and liquid crystal method in which an organic semiconductor thin film is pro display element provided with the organic film. duced from a solution and it being difficult to inexpensively manufacture devices having a large Surface area, it tended to BACKGROUND ART be difficult to obtain adequate carrier transportability with a single coating. Organic film elements provided with an organic film com Therefore, with the foregoing in view, an object of the posed of an organic semiconductor material are attracting 25 present invention is to provide an organic semiconductor attention as semiconductor elements provided with a semi composition that is able to form an organic film having high conductor thin film. In the manufacturing of these organic carrier transportability. In addition, an object of the present semiconductor elements, since an organic film can be easily invention is to provide an organic film that uses this organic formed by coating an organic semiconductor material, there semiconductor composition, and an organic film element, and is the advantage of being able to inexpensively produce 30 more specifically an organic film transistor, organic electrolu devices having a large Surface area. minescence element, electronic tag and liquid crystal display The properties of organic film elements are greatly depen element, provided with this organic film. dent on the carrier transportability of the organic film, and the higher this carrier transportability, the greater the demonstra Means for Solving the Problem tion of Superior properties as an organic film element. For 35 example, in the case of an organic field effect transistor pro In order to achieve the above-mentioned objects, the inven vided with a carrier transport layer composed of an organic tors of the present invention conducted Studies while focusing film, the higher the carrier transportability of the organic film, on the mixed State when mixing two or more types of organic the greater the current that is able to flow, and Superior prop semiconductor materials. As a result, the compatibility of two erties as a transistor, such as being able to increase the range 40 or more types of organic semiconductor materials was found of the adjustable amount of current, are obtained. Conse to greatly affect carrier transportability, thereby leading to quently, extensive studies are being conducted on organic completion of the present invention. semiconductor materials that allow the obtaining of high Namely, the organic semiconductor composition of the carrier transportability.
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