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A Method of Producing a Semiconducting Material

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A Method of Producing a Semiconducting Material Europaisches Patentamt J» European Patent Office Office europeen des brevets (TT) Publication number : 0 632 086 A2 EUROPEAN PATENT APPLICATION (2i) Application number: 94304431.3 © mt. ci.6: C08G 77/60, C09D 183/16 (22) Date of filing: 17.06.94 (30) Priority: 18.06.93 JP 172358/93 (72) Inventor : Ikai, Keizo 8 Chidori-cho, Naka-ku ui) Date of publication of application Yokohama-shi, Kanagawa-ken (JP) 04.01.95 Bulletin 95/01 Inventor : Matsuno, Mitsuo 8 Chidori-cho, Naka-ku (S) Designated Contracting States : Yokohama-shi, Kanagawa-ken (JP) DE FR GB Inventor : Minami, Masaki 8 Chidori-cho, Naka-ku 7i) Applicant : NIPPON OIL CO., LTD. Yokohama-shi, Kanagawa-ken (JP) 1-3-12, Nishishimbashi Minato-ku Tokyo (JP) 74) Representative : Topley, Paul et al G.F. Redfern & Co. Redfern House 149/151 Tarring Road Worthing West Sussex BN11 4HE (GB) A method of producing a semiconducting material. A method of producing a semiconducting material comprises reacting one or more of halogenosi- lanes with an alkali metal and/or an alkaline earth metal in an inert solvent to give a condensate and thermally decomposing the condensate. The condensate is dissolved in a suitable solvent such as toluene and tetrahydrofuran and applied by casting to a suitable substrate. The resulting semiconductor material in its film form has an optical band-gap (EO) of usually 0.1-4.0 eV. CO o CM CO LU Jouve, 18, rue Saint-Denis, 75001 PARIS EP 0 632 086 A2 This invention relates to a method of producing a semiconducting material for use in the formation of di- odes, transistors, field effect transistors, thyristors and like semiconductor elements. Agas-phase crystal growth procedure has found extensive use in the production of thin films of amorphous silicone or compound semiconductors in which their low molecular weight feedstock in gaseous phase is ther- 5 mally decomposed or chemically reacted in high vacuum to deposit on a substrate. This method howeverwould involve prohibitive costs to reduce to practice for making large semiconductor films because there will be re- quired large-scale vacuum devices on one hand and there is a limitation imposed upon the rate of film depos- ition on the other. With the foregoing drawbacks of the prior art in view, the present invention seeks to provide an improved w method of producing semiconducting materials at a maximum rate of efficiency and a minimum of costs. According to the invention, there is provided a method of producing semiconducting materials which com- prises reacting one or more of halogenosilanes of the group consisting of : a halogenomonosilane of the formula 15 20 X - Si - X (I) R2 25 wherein R1 and R2 are identical or different and each include C3-C12 secondary alkyl, tertiary alkyl and cycloalkyl groups, C8-C12 primary, secondary and tertiary aralkyl groups, silyl groups of the formula R3 R4 R5 Si- (I') wherein R3, R4 and R5 are identical or different and each include CrC8 alkyl groups and C6-C10 aryl 30 groups, and X which is chlorine, bromine or iodine, a halogenodisilane of the formula R« R« I I X - Si - Si - Ri° (II) I I 40 R7 Ro wherein R6-R10 are identical or different and each include C3-C12 secondary alkyl, tertiary alkyl and cy- 45 cloalkyl groups, C8-C12 primary, secondary and tertiary aralkyl groups, said silyl groups (I') and X which is chlor- ine, bromine or iodine, either one of R6-R10 being invariably X, and a halogenotrisilane of the formula 50 Rl* R13 R16 X - Si - Si - Si - R** i I i R12 R14 R16 2 EP 0 632 086 A2 wherein R11-R17 are identical or different and each include C3-C12 secondary alkyl, tertiary alkyl and cycloalkyl groups, C8-C12 primary, secondary and tertiary aralkyl groups, said silyl groups (I') and X which is chlorine, bromine or iodine, either one of R11-R17 being invariably X, with an alkali metal and/or an alkaline earth metal to give a condensate, and thermally decomposing said con- 5 densate. The term halogenomonosilane of the formula (I) according to the invention preferably includes tetrachlor- osilane, i-propyltrichlorosilane, t-butyltrichlorosilane, (i-methylpropyl)trichlorosilane, cyclohexyltrichlorosi- lane, (1,1,2-trimethylpropyl)trichlorosilane, a-phenethyltrichlorosilane, cumenyltrichlorosilane, (trimethylsi- lyl)trichlorosilane, di-i-propyldichlorosilane, di-t-butyldichlorosilane, di(1-methylpropyl)dichlorosilane, dicyclo- w hexyldichlorosilane, di-a-phenethyldichlorosilane and bis(trimethylsilyl)dichlorosilane, and further includes tetrabromosilane, i-propyltribromosilane, t-butyltribromosilane, (i-methylpropyl)tribromosilane, cyclohexyltri- bromosilane, (1,1,2-trimethylpropyl)tribromosilane, a-phenethyltribromosilane, cumenyltribromosilane, (tri- methylsilyl)tribromosilane, di-i-propyldibromosilane, di-t-butyldibromosilane, di(1-methylpropyl)dibromosi- lane, dicyclohexyldibromosilane, di-a-phenethyldibromosilane, bis(trimethylsilyl)dibromosilane, tetraiodosi- 15 lane, 1-propyltriiodosilane, t-butyltriiodosilane, (i-methylpropyl)triiodosilane, cyclohexyltriiodosilane, (1,1,2- trimethylpropyl)triiodosilane, a-phenethyltriiodosilane, cumenyltriiodosilane, (trimethylsilyl)triiodosilane, di-i- propyldiiodosilane, di-t-butyldiiodosilane,di(1-methylpropyl)diiodosilane, dicyclohexyldiiodosilane, di-a-phe- nethyldiiodosilane and bis(trimethylsilyl)diiodosilane. Halogenodisilanes of the formula (II) preferably include hexachlorodisilane, 1-propylpentachlorodisilane, 20 t-butylpentachlorodisilane, (i-methylpropyl)pentachlorodisilane, cyclohexylpentachlorodisilane, (1,1,2-trime- thylpropyl)pentachlorodisilane, a-phenethylpentachlorodisilane, cumenylpentachlorodisilane, (trimethylsi- lyl)pentachlorodisilane, 1,1-di-i-propyltetrachlorodisilane, 1,1-di-t-butyltetrachlorodisilane, 1,1-di(1-methyl- propyl)tetrachlorodisilane, 1,1-dicyclohexyltetrachlorodisilane, 1,1-di-a-phenethyltetrachlorodisilane, 1,1- bis(trimethylsilyl)tetrachlorodisilane, 1 ,2-di-i-propyltetrachlorodisilane, 1 ,2-di-t-butyltetrachlorodisilane, 1 ,2- 25 di(1-methylpropyl)tetrachlorodisilane, 1,2-dicylohexyltetrachlorodisilane, 1,2-di-a-phenethyltetrachlorodisi- lane and 1,2-bis(trimethylsilyl)tetrachlorodisilane. They further include 1,1,1-tri-i-propyltrichlorodisilane, 1,1,1-tri-t-butyltrichlorodisilane, 1,1,1-tri(1-methylpropyl)trichlorodisilane, 1,1-tricyclohexyltrichlorodisilane, 1,1,1-tri-a-phenethyltrichlorodisilane, 1,1,1-tris(trimethylsilyl)trichlorodisilane, 1,1,2-tri-i-propyltrichlorodisi- lane, 1,1,2-tri-t-butyltrichlorodisilane, 1,1,2-tri(1-methylpropyl)trichlorodisilane, 1,1,2-tricyclohexyltrichlorodi- 30 silane, 1,1,2-tri-a-phenethyltrichlorodisilane, 1,1,2-tris(trimethylsilyl)trichlorodisilane, hexabromodisilane, i- propylpentabromodisilane, t-butylpentabromodisilane, (i-methylpropyl)pentabromodisilane, cyclohexylpen- tabromodisilane, (1,1,2-trimethylpropyl)pentabromodisilane, a-phenethylpentabromodisilane, cumenylpen- tabromodisilane, (trimethylsilyl)pentabromodisilane, 1,1-di-i-propyltetrabromodisilane, 1,1-di-t-butyltetrabro- modisilane, 1,1-di(1-methylpropyl)tetrabromodisilane, 1,1-dicyclohexyltetrabromodisilane, 1,1-di-a-phenethyl- 35 tetrabromodisilane, 1,1-bis(trimethylsilyl)tetrabromodisilane, 1,12-di-i-propyltetrabromodisilane, 1,2-di-t-bu- tyltetrabromodisilane, 1,2-di(1-methylpropyl)tetrabromodisilane, 1,2-dicyclohexyltetrabromodisilane, 1,2-di- a-phenethyltetrabromodisilane, 1,2-bis(trimethylsilyl)tetrabromodisilane, 1,1,1-tri-i-propyltribromodisilane, 1,1,1-tri-t-butyltribromodisilane, 1,1,1-tri(1-methylpropyl)tribromodisilane, 1,1,1-tricyclohexyltribromodisi- lane, 1,1,1-tri-a-phenethyltribromodisilane, 1,1,1-tris(trimethylsilyl)tribromodisilane, 1,1,2-tri-i-propyltribro- 40 modisilane, 1,1,2-tri-t-butyltribromodisilane, 1,1,2-tri(1-methylpropyl)tribromodisilane, 1,1,2-tricyclohexyltri- bromodisilane, 1,1,2-tri-a-phenethyltribromodisilane, 1,1,2-tris(trimethylsilyl)tribromodisilane, hexaiododisi- lane, i-propylpentaiododisilane, t-butylpentaiododisilane, (i-methylpropyl)pentaiododisilane, cyclohexylpen- taiododisilane, (1,1,2-trimethylpropyl)pentaiododisilane, a-phenethylpentaiododisilane, cumenylpentaiododi- silane, (trimethylsilyl)pentaiododisilane, 1,1-di-i-propyltetraiododisilane, 1,1-di-t-butyltetraiododisilane, 1,1- 45 di(1-methylpropyl)tetraiododisilane, 1,1-dicyclohexyltetraiododisilane, 1,1-di-a-phenethyltetraiododisilane, 1,1-bis(trimethylsilyl)tetraiododisilane, 1,2-di-i-propyltetraiododisilane, 1,2-di-t-butyltetraiododisilane, 1,2- di(1-methylpropyl)tetraiododisilane, 1 ,2-dicyclohexyltetraiododisilane, 1 ,2-di-a-phenethyltetraiododisilane, 1,2-bis(trimethylsilyl)tetraiododisilane, 1,1,1-tri-i-propyltriiododisilane, 1,1,1 -tri-t-butyltriiododislane, 1,1,1- tri(1-methylpropyl)triiododisilane, 1,1,1-tricyclohexyltriiododisilane, 1,1,1-tri-a-phenethyltriiododisilane, 1,1 so ,1-tris(trimethylsilyl)triiododisilane, 1 ,1 ,2-tri-i-propyltriiododisilane, 1,1,2-tri-t-butyltriiododisilane, 1,1,2-tri(1- methylpropyl)triiododisilane, 1,1,2-tricyclohexyltriiododisilane, 1,1,2-tri-a-phenethyltriiododisilane and 1,1,2- tris(trimethylsilyl)triiododisilane. Halogenotrisilanes of the formula (III) preferably include octachlorotrisilane, 1-i-propylheptachlorotrisi- lane, 1-t-butylheptachlorotrisilane, 1-(1-methylpropyl)heptachlorotrisilane, 1-cyclohexylheptachlorotrisilane, 55 1-(1,1,2-trimethylpropyl)heptachlorotrisilane, 1-a-phenethylheptachlorotrisilane, 1-cumenylheptachlorotrisi- lane, 1-(trimethylsilyl)heptachlorotrisilane, 2-i-propylheptachlorotrisilane, 2-t-butylheptachlorotrisilane, 2-(1- methylpropyl)heptachlorotrisilane, 2-cyclohexylheptachlorotrisilane, 2-(1,1,2-trimethylpropyl)heptachlorotri-
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