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(12) United States Patent (10) Patent No.: US 9,490.433 B2 Miyawaki Et Al

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(12) United States Patent (10) Patent No.: US 9,490.433 B2 Miyawaki Et Al USOO9490433B2 (12) United States Patent (10) Patent No.: US 9,490.433 B2 Miyawaki et al. (45) Date of Patent: Nov. 8, 2016 (54) BENZOTHIENOBENZOTHIOPHENE 51/0067; H01L 29/786; H01L 51/0068; DERIVATIVE, ORGANIC SEMICONDUCTOR H01L 51/0558; C07D 495/04 MATERIAL AND ORGANIC TRANSISTOR See application file for complete search history. (71) Applicants: DIC Corporation, Tokyo (JP); (56) References Cited TOKYO INSTITUTE OF TECHNOLOGY, Tokyo (JP) U.S. PATENT DOCUMENTS 2011 0031487 A1 2/2011 Saito et al. (72) Inventors: Atsuhisa Miyawaki, Sakura-shi (JP); 2011/0040 107 A1 2/2011 Goto et al. Tetsuo Kusumoto, Kitaadachi-gun (JP); 2012/O161109 A1 6/2012 Wigglesworth et al. Yoshio Aoki, Kitaadachi-gun (JP); Aya 2014f0081028 A1 3/2014 Hanna et al. Ishizuka, Sakura-shi (JP); Yoshinobu 2014/O128983 A1 5/2014 Flaherty et al. Sakurai, Sakura-shi (JP); Yasuyuki Watanabe, Sakura-shi (JP); Jun-ichi FOREIGN PATENT DOCUMENTS Hanna, Tokyo (JP) JP 2008-010541. A 1, 2008 JP 2009-073,780 A 4/2009 (73) Assignees: DIC CORPORATION, Tokyo (JP); JP 2009-275032. A 11/2009 TOKYO INSTITUTE OF JP 2009-286781 A 12/2009 TECHNOLOGY, Tokyo (JP) JP 2010-177644 A 8, 2010 JP 2011-24.1331 A 12/2011 JP 2012-001442 A 1, 2012 (*) Notice: Subject to any disclaimer, the term of this JP 2012-134482 A T 2012 patent is extended or adjusted under 35 WO 2006/077888 A1 T 2006 U.S.C. 154(b) by 9 days. WO 2008/047896 A1 4/2008 WO 2009,125704 A1 10/2009 (21) Appl. No.: 14/426,862 WO 2009,125721 A1 10/2009 WO 2012/121393 A1 9, 2012 (22) PCT Filed: Sep. 10, 2013 OTHER PUBLICATIONS (86). PCT No.: PCT/UP2013/074364 S 371 (c)(1), International Search Report dated Oct. 8, 2013, issued in corre (2) Date: Mar. 9, 2015 sponding application No. PCT/JP2013/074364. (87) PCT Pub. No.: WO2014/038708 Primary Examiner — Samantha Shterengarts Assistant Examiner — Matt Mauro PCT Pub. Date: Mar. 13, 2014 (74) Attorney, Agent, or Firm — Westerman, Hattori, (65) Prior Publication Data Daniels & Adrian, LLP US 2015/0228913 A1 Aug. 13, 2015 (57) ABSTRACT (30) Foreign Application Priority Data The present invention, the present invention relates to an organic semiconductor material having a benzothienoben Sep. 10, 2012 (JP) ................................. 2012-1984.15 Zothiophene skeleton, an organic semiconductor ink con taining the organic semiconductor material, and an organic (51) Int. Cl. transistor using the organic semiconductor material. An HOIL 5L/00 (2006.01) object of the present invention is to provide an organic HOIL 29/786 (2006.01) semiconductor material that easily provides a film having a CO7D 495/04 (2006.01) high carrier mobility without the need for a complicated HOIL 5L/05 (2006.01) process. It was found that a BTBT derivative having a (52) U.S. Cl. particular arylene acetylene structure is crystallized by way CPC ......... HOIL 51/0074 (2013.01); C07D 495/04 of a high-order liquid crystal phase having a highly ordered (2013.01); HOIL 29/786 (2013.01); HOIL molecular arrangement, and thus the BTBT derivative easily 51/0052 (2013.01); HOIL 51/0067 (2013.01); forms a film having a high mobility without requiring HOIL 51/0068 (2013.01); HOIL 51/0558 complicated heat treatment even when the film is formed by (2013.01) printing. This finding led to the achievement of the object. (58) Field of Classification Search CPC ........... H01L 51/0074; H01L 51/0052; H01L 7 Claims, 8 Drawing Sheets U.S. Patent Nov. 8, 2016 Sheet 1 of 8 US 9,490,433 B2 - (a) M (b) U.S. Patent Nov. 8, 2016 Sheet 2 of 8 US 9,490.433 B2 FIG 7 (b) U.S. Patent Nov. 8, 2016 Sheet 3 of 8 US 9,490,433 B2 FG. 8 F.G. 10 (b) U.S. Patent Nov. 8, 2016 Sheet 4 of 8 US 9,490.433 B2 U.S. Patent Nov. 8, 2016 Sheet S of 8 US 9,490,433 B2 FG. 4 (a) (b) F.G. 5 (b) FG 16 U.S. Patent Nov. 8, 2016 Sheet 6 of 8 US 9,490,433 B2 F.G. 17 (b) F.G. 18 (b) FG. 19 U.S. Patent Nov. 8, 2016 Sheet 7 of 8 US 9,490,433 B2 ( o FG FG 22 ( ) (b ) U.S. Patent Nov. 8, 2016 Sheet 8 of 8 US 9,490,433 B2 US 9,490,433 B2 1. 2 BENZOTHENOBENZOTHOPHENE precursor of an organic semiconductor material and a pre DERIVATIVE, ORGANIC SEMICONDUCTOR cursor of an organic semiconductor polymer. MATERIAL AND ORGANIC TRANSISTOR PTL 7 describes compounds that have various BTBT Skeletons and exhibit a high-order liquid crystal phase. TECHNICAL FIELD However, derivatives according to the present invention are not known. The present invention relates to a benzothienobenzothio PTL 8 describes a compound for an organic thin-film phene derivative, an organic semiconductor material using transistor, the compound having a structure including an the same, an organic semiconductor ink containing the same, aromatic heterocyclic ring as a skeleton. However, deriva and an organic transistor using the same. 10 tives according to the present invention are not described. According to the description of Examples, the order of the BACKGROUND ART field-effect mobility is about 10 to 10° (cm/Vs). Hitherto, thin-film transistors (TFTs) formed by using PTL 9 describes that a specific organic compound having, amorphous silicon, or polycrystalline silicon have been 15 at the center, an aromatic hydrocarbon group or an aromatic widely used as Switching elements of a liquid crystal display heterocyclic group and an acetylene structure can be used in device, an organic electroluminescence (EL) display device an organic thin-film transistor. However, it is not described and the like. However, chemical vapor deposition (CVD) whether or not the compound exhibits a high-order liquid apparatuses used for producing such TFTs using silicon are crystal phase, which is an object of the present invention. expensive. Thus, the production of large TFT elements As described above, many organic semiconductor mate results in an increase in the production cost. In addition, rials having an improved mobility have been reported. since silicon materials are deposited at high temperatures, in However, in the case where an organic semiconductor thin view of a problem of heat resistance, these materials cannot film is formed by printing, it is difficult to obtain an organic be applied to plastic Substrates, which are likely candidates semiconductor film having a high mobility because the for substrates of flexible displays in the future. To solve this 25 organic semiconductor molecules are arranged randomly at problem, organic TFTs have been proposed in which, instead the time of printing, and thus a flow path through which of a silicon semiconductor, an organic semiconductor is used carriers flow is not formed. Accordingly, in this application, in a channel semiconductor layer. an organic semiconductor material that provides a film in By preparing a solution of an organic semiconductor, a which organic semiconductor molecules are easily oriented film of the organic semiconductor can be formed by printing 30 in one direction at the time of film formation by printing and at a low temperature. Accordingly, organic semiconductors through which carriers easily flow is required. do not require large-scale manufacturing facilities, and can also be applied to plastics, which have poor heat resistance. CITATION LIST Thus, organic semiconductors are expected to take the lead in flexible displays. On the other hand, organic semicon 35 Patent Literature ductors have a problem in practical application in that carrier mobilities of organic semiconductors are lower than those of PTL 1: International Publication No. WO 2006-077388 silicon semiconductors, resulting in a decreased response PTL 2: International Publication No. WO 2008-47896 speed of TFTs. Recently however, organic semiconductors PTL 3: Japanese Unexamined Patent Application Publica having mobilities equivalent to that of amorphous silicon 40 tion No. 2009-73780 have been developed. PTL 4: Japanese Unexamined Patent Application Publica For example, PTL 1 describes a compound having a tion No. 2012-134482 2.7-substituted 1 benzothieno 3.2-b1benzothiophene PTL 5: Japanese Unexamined Patent Application Publica skeleton (hereinafter, 1 benzothieno 3.2-b1benzothio tion No. 2003-286781 phene is abbreviated as “BTBT). PTL 1 describes com 45 PTL 6: Japanese Unexamined Patent Application Publica pounds having, as the Substituents, Substituents selected tion No. 2012-1442 from halogens, C-C alkyls, C-C alkyls having halo PTL 7: International Publication No. WO 2012-121393 gens, C-Cs alkyloxys, C-Cs alkylthios, aryls, and aryls PTL 8: International Publication No. WO 2009-125704 having at least one selected from halogens, C-C alkyls. PTL 9: International Publication No. WO 2009-125721 C-C alkyls having halogens, C-C alkyloxys, and 50 C-Cls alkylthios. It is described that the mobility (cm/Vs) SUMMARY OF INVENTION of these compounds is 0.17 to 0.31 cm/Vs. PTL 2 describes a compound having a 2.7-substituted Technical Problem BTBT skeleton. PTL 2 describes compounds having, as the Substituents, Substituents selected from a hydrogen atom and 55 However, many existing materials have a mobility of less halogeno-Substituted C-C aliphatic hydrocarbon groups. than 1 cm/Vs, which is insufficient to drive liquid crystal It is described that the mobility (cm/Vs) of these com display devices and organic EL devices. Although the com pounds is 0.12 to 4.5 cm/Vs. pounds described in PTL 2, which have been reported to PTL 3 describes a compound having a 2.7-substituted have high mobilities, can be formed into a film by spin BTBT skeleton having a chalcogenophene ring.
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