KR20150110310A - composition comprising boron-containing compound, boron-containing thin film and method for manufacturing boron-containing thin film - Google Patents
composition comprising boron-containing compound, boron-containing thin film and method for manufacturing boron-containing thin film Download PDFInfo
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- KR20150110310A KR20150110310A KR1020150017921A KR20150017921A KR20150110310A KR 20150110310 A KR20150110310 A KR 20150110310A KR 1020150017921 A KR1020150017921 A KR 1020150017921A KR 20150017921 A KR20150017921 A KR 20150017921A KR 20150110310 A KR20150110310 A KR 20150110310A
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- boron
- thin film
- alkyl
- aryl
- heterocycloalkyl
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- 229910052796 boron Inorganic materials 0.000 title claims abstract description 111
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 239000010409 thin film Substances 0.000 title claims abstract description 68
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 21
- 125000006707 (C3-C12) heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 17
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002243 precursor Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 16
- 238000000151 deposition Methods 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229910052582 BN Inorganic materials 0.000 description 8
- 230000008033 biological extinction Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000005530 etching Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 230000010354 integration Effects 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910003460 diamond Inorganic materials 0.000 description 4
- 239000010432 diamond Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012495 reaction gas Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OITIYEGGDISXGX-UHFFFAOYSA-N CNB(NC)N(C)C Chemical compound CNB(NC)N(C)C OITIYEGGDISXGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000231 atomic layer deposition Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ODXMMDJMDRNJRH-UHFFFAOYSA-N B1NCCN1 Chemical class B1NCCN1 ODXMMDJMDRNJRH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229910003697 SiBN Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PPWPWBNSKBDSPK-UHFFFAOYSA-N [B].[C] Chemical compound [B].[C] PPWPWBNSKBDSPK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 1
- 229910021402 lonsdaleite Inorganic materials 0.000 description 1
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/04—Coating on selected surface areas, e.g. using masks
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/34—Nitrides
- C23C16/342—Boron nitride
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/36—Carbonitrides
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
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- General Chemical & Material Sciences (AREA)
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- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Inorganic Chemistry (AREA)
Abstract
Description
본 발명은 붕소함유 화합물을 포함하는 조성물, 이를 이용하여 제조된 붕소함유 박막 및 이를 이용하는 붕소함유 박막의 제조방법에 관한 것으로, 보다 상세하게는 붕소함유 박막의 전구체로 유용하게 사용될 수 있는 붕소함유 화합물을 포함하는 조성물, 이를 이용한 붕소함유 박막 및 붕소함유 박막의 제조방법에 관한 것이다.The present invention relates to a composition containing a boron-containing compound, a boron-containing thin film prepared using the same, and a method for producing a boron-containing thin film using the same, and more particularly to a boron-containing thin film which can be usefully used as a precursor of a boron- A boron-containing thin film using the boron-containing thin film, and a method for producing the boron-containing thin film.
반도체 제조 기술의 발달로 반도체 소자의 크기는 소형화되고 소자의 집적도는 빠르게 증가되고 있다. 그러나, 집적도가 증가하게 되면 도선들간의 간섭에 의한 신호의 전달이 지연되기 때문에 소자의 성능은 배선 속도에 좌우되게 된다. 이에 저항과 정전용량을 적게 하기 위해서는 반도체 층간 절연막의 정전용량을 낮추는 것이 필요하다. 종래에는 반도체 층간 절연막으로 유전율이 약 k=4.0 정도의 실리콘산화막(SiO2)이 사용되어 왔으나 반도체 집적도의 향상에 따라 실리콘산화막의 유전율을 갖는 절연막은 이제 한계에 도달하여 새로운 절연막을 사용해야 한다. 절연층 두께를 키우면 정전용량은 줄어들지만, 고집적화의 방해요소가 되기 때문에 궁극적인 해결책은 유전율의 최소화에서 찾을 수밖에 없다. With the development of semiconductor manufacturing technology, the size of semiconductor devices is becoming smaller and the degree of integration of devices is rapidly increasing. However, as the degree of integration increases, the signal transmission due to the interference between the conductors is delayed, so the performance of the device depends on the wiring speed. In order to reduce the resistance and the electrostatic capacity, it is necessary to lower the electrostatic capacitance of the semiconductor interlayer insulating film. Conventionally, a silicon oxide film (SiO 2 ) having a dielectric constant of about k = 4.0 has been used as a semiconductor interlayer insulating film. However, an insulating film having a dielectric constant of a silicon oxide film with an increase in semiconductor integration degree has reached the limit and a new insulating film must be used. Increasing the insulation layer thickness reduces the capacitance, but it is an obstacle to high integration, so the ultimate solution is to minimize the permittivity.
또한 소자의 고집적도로 인해 소자의 패턴 크기 및 간격이 점점 감소하면서 패턴의 미세화가 동시에 진행 되고 있으며, 패턴의 미세화를 구현하기 위해서는 패터닝에 요구되는 식각 기술이 요구된다. In addition, due to the high integration of the device, pattern size and spacing of the device are gradually reduced, and pattern miniaturization is progressing at the same time. In order to realize pattern miniaturization, etching technique required for patterning is required.
그러나 식각 기술에서 패터닝을 위한 포토레지스트의 두께가 얇아지면서 포토레지스트가 후속 식각 공정을 위한 마스크로서의 기능을 다하지 못하고 있다. 이의 해결방안으로 산화막, 폴리실리콘막, 비정질 탄소막등을 도입하여 피식각층과 포토레지스트 사이에 하드마스크를 도입하여 식각마진을 확보하는 기술이 제안되었으나, 공정과정이 복잡하고 공정비용이 증가하는 문제점이 있다.However, as the thickness of the photoresist for patterning in the etching technique becomes thinner, the photoresist does not function as a mask for a subsequent etching process. As a solution to this problem, there has been proposed a technique of introducing an oxide film, a polysilicon film, an amorphous carbon film, etc., and introducing a hard mask between the etching layer and the photoresist to secure the etching margin. However, have.
따라서 최근에는 스핀 코팅 방식을 이용하여 공정과정의 단순화, 비용감소를 시도하고 있으나, 식각 선택비가 낮기 때문에 기능을 충분히 발휘하지 못하고 있는 실정이다.Recently, the spin coating method has been used to simplify the process and reduce the cost. However, since the etching selectivity is low, the function is not sufficiently exhibited.
이에 최근 들어서 붕소함유 박막이 저 유전율 소자 및 하드마스크 소자에 대한 도입의 연구가 이루어지고 있다(Japanese Journal of Applied Physics 49(2010)04DB10-1-04DB10-4), (Diamond & Related Materials 18 (2009) 1048-1051)., (Materials Science and Engineering B47 (1997) 257-262). 붕소 포함 박막은 저밀도상의 육각형 질화붕소(h-BN), 마름모형 질화붕소(r-BN), 고밀도상의 육방정계 질화붕소(w-BN), 입방 질화붕소(cubic-BN)등의 여러가지 결정 구조로 구분하여 진다. w-질화붕소는 다이아몬드의 hexagonal 형태인 lonsdaleite와 유사한 구조이고, c-질화붕소는 다이아몬드와 유사한 구조이다. 이와 같은 다양한 구조의 붕소 포함 박막은 하드-머터리얼로 알려져 있으며, 특히 붕소탄소질화막(BCN)의 young modulus 값은 20GPA 이상의 높은 기계적 강도 , 1.8 이하의 낮은 유전상수 및 낮은 저항 값(6×1012Ωcm)을 가지고 있다. (Japanese Journal of Applied Physics 49(2010)04DB10-1~04DB10-4).Recently, boron-containing thin films have been studied for introduction into low-permittivity devices and hard mask devices ( Japanese Journal of Applied Physics 49 (2010) 04DB10-1-04DB10-4), ( Diamond & Related Materials 18 ) 1048-1051), ( Materials Science and Engineering B47 (1997) 257-262). The boron-containing thin film has various crystal structures such as hexagonal boron nitride (h-BN), rhombic boron nitride (r-BN), hexagonal boron nitride (w-BN) and cubic boron nitride . w-boron nitride has a structure similar to lonsdaleite, which is a hexagonal form of diamond, and c-boron nitride has a structure similar to diamond. The boron-containing thin film of the same variety of structures may be stored on the hard-known as meoteo real, especially boron young modulus value of the carbon nitride (BCN) is a low dielectric constant and a low resistance value of the above high mechanical strength, 1.8 or less 20GPA (6 × 10 12 Ωcm). ( Japanese Journal of Applied Physics 49 (2010) 04DB10-1 ~ 04DB10-4).
그러나 여전히 wide band gap, negative electron affinity, 우수한 전기적 특성, 높은 기계적 강도 및 낮은 누설전류값을 가지는 붕소화합물의 개발이 요구된다.However, it is still required to develop a boron compound having a wide band gap, a negative electron affinity, an excellent electrical characteristic, a high mechanical strength and a low leakage current value.
본 발명은 붕소를 함유한 박막의 선구물질로 사용가능한 붕소함유 화합물을 함유하는 조성물을 제공한다.The present invention provides a composition containing a boron-containing compound usable as a precursor of a thin film containing boron.
또한 본 발명은 본 발명의 붕소함유 화합물을 포함하는 조성물을 이용하여 제조된 붕소함유 박막과 이의 제조방법을 제공한다.The present invention also provides a boron-containing thin film prepared by using the composition containing the boron-containing compound of the present invention and a method for producing the same.
본 발명은 높은 기계적 강도, 낮은 누설전류값등의 기계적, 화학적 전기적 특성이 우수한 붕소함유 박막을 형성하기 위한 선구물질로 매우 유용한 붕소함유 화합물을 포함하는 조성물, 구체적으로 붕소함유 박막증착용 조성물을 제공하는 것으로, 본 발명의 붕소함유 화합물은 하기 화학식 1로 표시된다.The present invention relates to a composition containing a boron-containing compound which is very useful as a precursor for forming a boron-containing thin film having excellent mechanical strength, low leakage current value and the like, excellent in mechanical and chemical electrical properties, The boron-containing compound of the present invention is represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
[상기 화학식 1에서,[In the above formula (1)
상기 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있으며; Wherein R 1 to R 4 independently represent hydrogen, (C1-C10) alkyl, (C1-C10) alkoxy, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl, R 1 alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl to R 4 is methyl, halogen, trifluoromethyl (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3- C20) heteroaryl; < / RTI >
n은 1 내지 9의 정수이다.] and n is an integer of 1 to 9.]
바람직하게 본 발명의 상기 화학식 1은 하기 화학식 2로 표시될 수 있다.Preferably, Formula 1 of the present invention can be represented by Formula 2 below.
[화학식 2](2)
[상기 화학식 2에서,[In the formula (2)
R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있다.]R 1 to R 4 are each independently of the other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, Alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl of R 1 to R 4 are independently selected from the group consisting of halogen, trifluoromethyl, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3-C20) ) Heteroaryl. ≪ / RTI >
바람직하게 상기 화학식 2에서 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬일 수 있으며, Preferably, R 1 to R 4 are independently of each other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10)
보다 바람직하게는 R1 및 R2는 서로 독립적으로 (C1-C10)알킬, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 또는 (C3-C20)헤테로아릴이며;More preferably, R 1 and R 2 are each independently of the other (C 1 -C 10) alkyl, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, (C 6 -C 20) Aryl;
R3 및 R4는 서로 독립적으로 (C1-C10)알킬일 수 있다.R 3 and R 4 may independently of each other be (C 1 -C 10) alkyl.
본 발명의 붕소함유 화합물을 포함하는 조성물에서 붕소함유 화합물은 하기 구조에서 선택될 수 있으나, 이에 한정이 있는 것은 아니다.In the composition containing the boron-containing compound of the present invention, the boron-containing compound may be selected from the following structures, but is not limited thereto.
또한 본 발명은 본 발명의 붕소함유 화합물을 포함하는 조성물을 이용하여 제조되는 붕소함유 박막 및 붕소함유 박막의 제조방법을 제공한다.The present invention also provides a process for producing a boron-containing thin film and a boron-containing thin film which are produced by using the composition containing the boron-containing compound of the present invention.
본 발명의 조성물은 붕소함유 박막의 전구체로 사용되며, 상온에서 액체로 휘발성이 높고 열적 안정성이 매우 우수한 붕소함유 화합물을 포함하여 이를 이용하여 제조되는 붕소함유 박막은 높은 순도와 내구성을 가진 저유전소자 및 하드마스크로 이용가능하다.The composition of the present invention comprises a boron-containing compound which is used as a precursor of a boron-containing thin film and has a high volatility as a liquid at room temperature and an excellent thermal stability, and a boron-containing thin film produced by using the boron-containing compound has a high purity and durability. And a hard mask.
본 발명의 붕소함유 박막의 제조방법은 본 발명의 붕소함유 화합물을 포함하는 조성물을 스핀코팅과 같은 단순한 용액공정으로 용이하게 박막형성이 가능하다.The method for producing a boron-containing thin film of the present invention can easily form a thin film by a simple solution process such as spin coating of a composition containing the boron-containing compound of the present invention.
본 발명의 붕소함유 박막은 높은 휘발성 및 열 안정성을 가지는 본 발명의 붕소함유 화합물을 포함하는 조성물을 이용하여 제조됨으로써 높은 순도와 내구성을 가진다.The boron-containing thin film of the present invention has high purity and durability by being produced using a composition containing the boron-containing compound of the present invention having high volatility and thermal stability.
도 1은 실시예 1에서 제조된 1,3-디메틸-2-디메틸아미노디아자보란의 1H-NMR 그래프이며,
도 2는 실시예 1에서 제조된 1,3-디메틸-2-디메틸아미노디아자보란의 증기압 그래프이며,
도 3은 실시예 1에서 제조된 1,3-디메틸-2-디메틸아미노디아자보란의 열중량(TGA)그래프이며,
도 4는 실시예 1에서 제조된 1,3-디메틸-2-디메틸아미노디아자보란을 이용하여 증착된 붕소함유 박막의 적외선 분광계 스펙트럼을 나타낸 도면이며,
도 5는 실시예 1에서 제조된 1,3-디메틸-2-디메틸아미노디아자보란을 이용하여 증착된 붕소함유 박막의 깊이에 따른 조성 변화를 나타낸 그래프이다.1 is a 1 H-NMR chart of 1,3-dimethyl-2-dimethylaminodiazaborane prepared in Example 1,
2 is a graph showing the vapor pressure of 1,3-dimethyl-2-dimethylaminoadazaborane prepared in Example 1,
3 is a thermogravimetric (TGA) graph of 1,3-dimethyl-2-dimethylaminoadazaborane prepared in Example 1,
4 is an infrared spectrometry spectrum of a boron-containing thin film deposited using 1,3-dimethyl-2-dimethylaminodiazaborane prepared in Example 1,
FIG. 5 is a graph showing the compositional change according to the depth of a boron-containing thin film deposited using 1,3-dimethyl-2-dimethylaminodiazaborane prepared in Example 1. FIG.
본 발명은 상온에서 액체이며, 휘발성이 높고 열적 안정성이 높아 붕소함유 박막형성에 매우 유용한 붕소함유 화합물을 포함하는 조성물을 제공하는 것으로, 본 발명의 붕소함유 화합물은 하기 화학식 1로 표시된다.The present invention provides a composition containing a boron-containing compound which is liquid at room temperature, has high volatility and high thermal stability and is very useful for forming a boron-containing thin film, and the boron-containing compound of the present invention is represented by the following formula (1).
[화학식 1][Chemical Formula 1]
[상기 화학식 1에서,[In the above formula (1)
상기 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있으며; Wherein R 1 to R 4 independently represent hydrogen, (C1-C10) alkyl, (C1-C10) alkoxy, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl, R 1 alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl to R 4 is methyl, halogen, trifluoromethyl (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3- C20) heteroaryl; < / RTI >
n은 1 내지 9의 정수이다.] and n is an integer of 1 to 9.]
본 발명의 조성물에 포함된 붕소함유 화합물은 1,3,2-디아자보롤리딘(1,3,2-diazaborolidine)의 골격을 가지고 붕소에 치환되거나 치환되지 않은 아민기를 작용기로 가지고 있어 상온에서 액체 또는 녹는점이 낮아 휘발성이 높기 때문에 붕소함유 박막형성에 매우 유용하게 사용할 수 있다.The boron-containing compound contained in the composition of the present invention has a skeleton of 1,3,2-diazaborolidine and has an amine group substituted or unsubstituted in boron as a functional group, Or has a low melting point and a high volatility, it can be very usefully used for forming a boron-containing thin film.
나아가 본 발명의 붕소함유 화합물은 열적으로도 매우 안정하며, 이를 포함하는 조성물을 이용하여 형성된 붕소함유 박막은 기계적 특성 또한 매우 높다.Further, the boron-containing compound of the present invention is very stable even thermally, and the boron-containing thin film formed using the composition containing the boron-containing compound has a very high mechanical property.
본 발명의 붕소함유 화합물을 포함하는 조성물은 구체적으로 붕소함유 박막을 형성하기 위한 전구체로 상기 화학식 1로 표시되는 붕소함유 화합물을 포함한다.The composition containing the boron-containing compound of the present invention specifically includes a boron-containing compound represented by the above formula (1) as a precursor for forming a thin film containing boron.
(C1-C10)알킬은 탄소수 1 내지 10의 알킬 유니트를 가지는 알킬기를 의미하며, 바람직하게는 탄소수 1 내지 7, 보다 바람직하게는 1 내지 5의 알킬 유니트를 가진다.(C1-C10) alkyl means an alkyl group having an alkyl unit of 1 to 10 carbon atoms, preferably an alkyl unit having 1 to 7 carbon atoms, more preferably 1 to 5 carbon atoms.
본 명세서에 기재된 "할로겐"은 할로겐족 원소를 나타내며, 예컨대, 플루오로, 클로로, 브로모 및 요오도를 포함한다. As used herein, the term "halogen" refers to a halogen group element and includes, for example, fluoro, chloro, bromo and iodo.
본 명세서에 기재된 "헤테로시클로알킬"은 헤테로원자로서 고리 내에 산소, 황 또는 질소를 포함하는 지환족고리를 의미하며, 헤테로원자의 개수는 1-4이며, 바람직하게는 1-2이다. 헤테로시클로알킬에서 시클로알킬은 바람직하게는 모노시클로알킬 또는 비시클로알킬이며, 방향족고리인 아릴 또는 헤테로아릴이 융합되어 있는 경우도 포함한다. "Heterocycloalkyl" as used herein means an alicyclic ring containing hetero atom, oxygen, sulfur or nitrogen in the ring, and the number of heteroatoms is 1-4, preferably 1-2. Cycloalkyl in heterocycloalkyl is preferably monocycloalkyl or bicycloalkyl, including those in which an aromatic ring, aryl or heteroaryl, is fused.
또한 본 발명에 기재된 "아릴"은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐 등을 포함하지만, 이에 한정되지 않는다. "Aryl" according to the present invention is an organic radical derived from aromatic hydrocarbons by the removal of one hydrogen, in which each ring is optionally substituted by a single or fused ring containing from 4 to 7, preferably 5 or 6 ring atoms A ring system, and a form in which a plurality of aryls are connected by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, and the like.
본 발명에 기재된 "헤테로아릴"은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다."Heteroaryl" as used herein includes 1-4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring backbone atoms, and the remaining aromatic ring backbone atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond.
바람직하게 본 발명의 상기 화학식 1로 표시되는 붕소함유 화합물은 하기 화학식 2로 표시될 수 있다.Preferably, the boron-containing compound represented by
[화학식 2](2)
[상기 화학식 2에서,[In the formula (2)
R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있다.]R 1 to R 4 are each independently of the other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, Alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl of R 1 to R 4 are independently selected from the group consisting of halogen, trifluoromethyl, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3-C20) ) Heteroaryl. ≪ / RTI >
바람직하게는 본 발명의 일 실시예에 따른 상기 화학식 2에서 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬일 수 있으며, 우수한 열적 안정성과 높은 휘발성을 가지기 위한 측면에서 보다 바람직하게는 R1 및 R2는 서로 독립적으로 (C1-C10)알킬, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 또는 (C3-C20)헤테로아릴이며;Preferably, in formula (2), R 1 to R 4 independently of one another are hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) (C6-C20) aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl, and they may have a higher thermal stability and higher volatility Preferably, R 1 and R 2 are independently from each other selected from the group consisting of (C 1 -C 10) alkyl, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, (C 6 -C 20) aryl or (C 3 -C 20) ;
R3 및 R4는 서로 독립적으로 (C1-C10)알킬일 수 있다.R 3 and R 4 may independently of each other be (C 1 -C 10) alkyl.
보다 바람직하게는 상기 화학식 2에서 R1 및 R2는 서로 독립적으로 (C1-C10)알킬이며;More preferably in Formula 2 R 1 and R 2 are independently (C1-C10) alkyl with one another;
R3 및 R4는 서로 독립적으로 (C1-C10)알킬일 수 있다.R 3 and R 4 may independently of each other be (C 1 -C 10) alkyl.
본 발명의 일 실시예에 따른 붕소함유 화합물은 한정이 있는 것은 아니나, 구체적으로 하기 화합물에서 선택될 수 있다.The boron-containing compound according to one embodiment of the present invention is not limited, but may be specifically selected from the following compounds.
본 발명의 조성물에 포함되는 붕소함유 화합물은 하기 화학식 3과 하기 화학식 4를 반응시켜 상기 화학식 1로 표시되는 붕소함유 화합물을 제조하는 단계;를 포함하여 제조될 수 있다.The boron-containing compound contained in the composition of the present invention can be prepared by reacting the following formula (3) with the following formula (4) to prepare the boron-containing compound represented by the formula (1).
[화학식 3](3)
MAMA
[화학식 4][Chemical Formula 4]
[상기 화학식 3 및 화학식 4에서,[In the above formulas (3) and (4)
상기 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있으며; Wherein R 1 to R 4 independently represent hydrogen, (C1-C10) alkyl, (C1-C10) alkoxy, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl, R 1 alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl to R 4 is methyl, halogen, trifluoromethyl (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3- C20) heteroaryl; < / RTI >
M는 알칼리금속이온이며;M is an alkali metal ion;
A는 
X1은 할로겐이며;X 1 is halogen;
n은 1 내지 9의 정수이다.] and n is an integer of 1 to 9.]
본 발명의 붕소함유 화합물의 제조방법은 매우 단순한 공정으로 높은 순도의 붕소함유 화합물을 높은 수율로 제조할 수 있어 매우 효과적이며 경제적이다.The process for producing the boron-containing compound of the present invention is very effective and economical because it can produce a boron-containing compound of high purity at a high yield by a very simple process.
본 발명의 일 실시예에 따른 상기 화학식 1의 제조방법에서 M은 알칼리금속이온이라면 한정이 있지는 않으나 Li+가 바람직하다.In the production method of
본 발명의 일 실시예에 따른 상기 화학식 3과 화학식 4를 반응시켜 상기 화학식 1을 제조할 시 반응은 15 내지 60℃에서 6 내지 12시간동안 수행될 수 있으며, 반응효율측면에서 바람직하게는 15 내지 40℃에서 8 내지 12시간동안 수행될 수 있다.When the compound of formula (3) is reacted with the compound of formula (4) according to an embodiment of the present invention, the reaction may be carried out at 15 to 60 ° C for 6 to 12 hours, RTI ID = 0.0 > 40 C < / RTI > for 8 to 12 hours.
본 발명의 붕소함유 화합물의 제조방법의 일 실시예에 따른 상기 화학식 4는 염기하에 하기 화학식 5와 하기 화학식 6을 반응시켜 제조될 수 있다.According to one embodiment of the process for preparing a boron-containing compound of the present invention, Formula 4 may be prepared by reacting a compound represented by Formula 5 below with a compound represented by Formula 6 under a base.
[화학식 5][Chemical Formula 5]
B(X1)3 B (X 1 ) 3
[화학식 6][Chemical Formula 6]
[상기 화학식 5 및 6에서,[In the above formulas (5) and (6)
R1 및 R2는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있으며; R 1 and R 2 are independently from each other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, Alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl of R 1 to R 4 are independently selected from the group consisting of halogen, trifluoromethyl, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3-C20) ) Heteroaryl; < / RTI >
X1은 할로겐이며;X 1 is halogen;
n은 1 내지 9의 정수이다.]and n is an integer of 1 to 9.]
본 발명의 붕소함유 화합물의 제조방법의 일 실시예에 따른 염기는 유기합성에서 통상적으로 사용되는 염기이면 모두 가능하나, 하기 화학식 7로 표시되는 화합물일 수 있다.The base according to one embodiment of the method for producing the boron-containing compound of the present invention may be any of the bases conventionally used in organic synthesis, but may be a compound represented by the following general formula (7).
[화학식 7](7)
N(R11)(R12)(R13)N (R 11 ) (R 12 ) (R 13 )
[상기 화학식 7에서,[Formula 7]
R11 내지 R13은 서로 독립적으로 수소 또는 (C1-C10)알킬이다.]R 11 to R 13 independently from each other are hydrogen or (C 1 -C 10) alkyl]
본 발명의 붕소함유 화합물의 제조방법에서 사용되는 용매는 통상의 유기용매중 출발물질과 반응하지 않는 용매이면 모두 가능하나, 일례로 노말헥산(n-Hexane), 사이클로헥산(Cyclohexane), 노말펜탄(n-Pentane), 다이에틸에테르(Ether), 톨루엔(Toluene), 테트라하이드로퓨란(THF), 다이클로로메탄(M.C), 트리클로로메탄(Chloroform)으로 이루어진 군으로부터 선택되는 1종 이상이 선택될 수 있다.The solvent used in the process for preparing the boron-containing compound of the present invention may be any solvent that does not react with the starting material in the conventional organic solvent. Examples of the solvent include n-hexane, cyclohexane, at least one selected from the group consisting of n-pentane, diethyl ether, toluene, tetrahydrofuran (THF), dichloromethane (MC) and trichloromethane have.
본 발명의 붕소함유 화합물을 포함하는 조성물은 본 발명의 붕소함유 화합물을 박막증착용 전구체로 포함하며 이의 조성물내 붕소함유 화합물의 함량은 박막의 성막조건 또는 박막의 두께, 특성등을 고려하여 당업자가 인식할 수 있는 범위내로 포함될 수 있다.The composition containing the boron-containing compound of the present invention contains the boron-containing compound of the present invention as a thin film deposition precursor, and the content of the boron-containing compound in the composition is not particularly limited as long as a thin film is formed, It can be included within a recognizable range.
또한 본 발명은 본 발명의 붕소함유 화합물을 포함하는 조성물을 이용하여 제조되는 붕소함유 박막을 제공한다.The present invention also provides a boron-containing thin film produced using the composition comprising the boron-containing compound of the present invention.
본 발명의 붕소함유 박막은 통상적인 방법으로 제조될 수 있으며, 일례로 유기금속 화학기상 증착법(MOCVD), 원자층 증착법(ALD) 공정, 저압 기상 증착법(LPCVD), 플라즈마 강화 기상 증착법 (PECVD) 또는 플라즈마 강화 원자층 증착법(PEALD)등을 들 수 있다.The boron-containing thin film of the present invention can be manufactured by a conventional method, and examples thereof include metal organic chemical vapor deposition (MOCVD), atomic layer deposition (ALD), low pressure vapor deposition (LPCVD), plasma enhanced vapor deposition Plasma enhanced atomic layer deposition (PEALD), and the like.
본 발명의 붕소함유 박막은 본 발명의 붕소함유 화합물을 이용하여 제조되는 것으로, 한정이 있는 것은 아니나 일례로 붕소질화막(BN), 붕소산화막(B2O3), 붕소탄소질화막(BCN), 규소붕소질화막(SiBN)일 수 있다.The boron-containing thin film of the present invention is produced by using the boron-containing compound of the present invention. The boron-containing thin film may be a boron nitride film (BN), a boron oxide film (B 2 O 3 ), a boron carbon nitride film (BCN) A boron nitride film (SiBN).
본 발명의 붕소함유 박막은 높은 휘발성과 높은 열적 안정성을 가지는 본 발명의 붕소함유 화합물을 포함하는 조성물을 사용하여 제조됨으로써 물리적, 전기적, 화학적 특성이 매우 우수하다.The boron-containing thin film of the present invention is excellent in physical, electrical and chemical properties by being produced using the composition containing the boron-containing compound of the present invention having high volatility and high thermal stability.
또한 본 발명은 본 발명의 붕소함유 화합물을 포함하는 조성물을 이용하여 제조되는 붕소함유 박막을 제공한다.The present invention also provides a boron-containing thin film produced using the composition comprising the boron-containing compound of the present invention.
본 발명의 붕소함유 박막의 제조방법에서 본 발명의 붕소함유 화합물의 주입온도는 5 내지 120℃일 수 있으며, 본 발명의 붕소함유 화합물의 높은 휘발성으로인해 붕소함유 화합물이 증착될 기판의 온도는 100 내지 450℃, 챔버내부 압력은 0.1 내지 10 torr일 수 있다.In the process for preparing the boron-containing thin film of the present invention, the boron-containing compound of the present invention may be implanted at a temperature of 5 to 120 캜, and the boron-containing compound of the present invention has a high volatility, To 450 < 0 > C, and the pressure in the chamber may be 0.1 to 10 torr.
본 발명의 붕소함유 박막의 제조방법에서 사용되는 반응가스는 한정이 있는 것은 아니나, 수소(H2), 히드라진(N2H4), 오존(O3), 암모니아(NH3), 질소(N2), 실란(SiH4), 보란(BH3), 디보란(B2H6) 및 포스핀(PH3)에서 선택되는 하나 또는 하나이상의 혼합기체일 수 있다.
The reaction gas used in the method for producing the boron-containing thin film of the present invention is not limited, but hydrogen (H 2 ), hydrazine (N 2 H 4 ), ozone (O 3 ), ammonia (NH 3 ) 2 ), silane (SiH 4 ), borane (BH 3 ), diborane (B 2 H 6 ) and phosphine (PH 3 ).
아래에 실시 예를 통하여 본 발명을 더 구체적으로 설명한다. 이에 앞서, 본 명세서 및 청구범위에 사용된 용어나 단어는 통상적이거나 사전적인 의미로 한정해서 해석되어서는 아니 되며, 발명자는 그 자신의 발명을 가장 최선의 방법으로 설명하기 위해 용어의 개념을 적절하게 정의할 수 있다는 원칙에 입각하여 본 발명의 기술적 사상에 부합하는 의미와 개념으로 해석되어야만 한다. 따라서, 본 명세서에 기재된 실시 예와 도면에 도시된 구성은 본 발명의 가장 바람직한 일 실시 예에 불과할 뿐이고 본 발명의 기술적인 사상을 모두 대변하는 것은 아니므로, 본 출원시점에 있어서 이들은 대체할 수 있는 다양한 균등물과 변형 예들이 있음을 이해하여야 한다.Hereinafter, the present invention will be described in more detail by way of examples. Prior to this, terms and words used in the present specification and claims should not be construed as limited to ordinary or dictionary terms, and the inventor should appropriately interpret the concepts of the terms appropriately It should be interpreted in accordance with the meaning and concept consistent with the technical idea of the present invention based on the principle that it can be defined. Therefore, the embodiments described in the present specification and the configurations shown in the drawings are only the most preferred embodiments of the present invention, and not all of the technical ideas of the present invention are described. Therefore, It should be understood that there are numerous equivalents and variations.
이하 모든 화합물 실시예는 글로브 박스 또는 슐랭크 관을 이용하여 무수 및 비활성 분위기 하에서 수행 하였으며, 생성물은 양성자 핵자기 공명 분광법(1H Nuclear Magnetic Resonance, NMR, 400MHz Ultrashield, Buruker), 열무게 분석법(thermogravimetric analysis, TGA, L81-II, LINSEIS) 및 가스 크래마토그래피(Gas Chromatography, GC, 7890A, Agilent Technologies)를 이용하여 분석 하였으며, 증착한 박막은 적외선 분광법(infrared spectroscopy, IFS66V/S & Hyperion 3000, Bruker Optiks) 및 오제전자분광기(Microlab 350, Thermo Electron)를 이용하여 막 성분을 분석 하였다.All the compound examples below were carried out in an anhydrous and inert atmosphere using a glove box or a syringe tube and the product was analyzed by proton nuclear magnetic resonance spectroscopy ( 1 H Nuclear Magnetic Resonance, NMR, 400 MHz Ultrashield, Buruker), thermogravimetric (IFS66V / S & Hyperion 3000, Bruker (R)) were used for the analysis of the deposited films. The films were analyzed by infrared spectroscopy (IFS66V / S & Hyperion 3000, LINSEIS) and Gas Chromatography (GC, 7890A, Agilent Technologies) Optiks) and an electrophoretic spectrometer (Microlab 350, Thermo Electron).
[실시예 1] 1,3-디메틸-2-디메틸아미노디아자보란 합성 [Example 1] Synthesis of 1,3-dimethyl-2-dimethylaminoadaborane
불꽃 건조 된 3000ml 플라스크 질소 분위기 하에서 노르말 헥산 2000ml 주입하고 -30℃ 냉각 후 트리클로로 보론(BCl3) 300g (2.56mol)을 첨가하였다. 이 후 트리에틸아민 570g(5.63mol)을 1시간에 걸쳐 천천히 첨가하고 25℃ 까지 온도를 올린 후 1시간동안 교반시켰다. 교반 후 40℃로 승온후 N,N′-디메틸에틸렌디아민 225.7g(2.56mol)을 3시간에 걸쳐 서서히 주입하였다. 그 후 40℃-50℃ 온도 유지하며 12시간 교반시켰다. 부산물로 나온 (TEAㅇHCl)을 여과하고, 1,3-디메틸-2-클로로-1,3,2-디아자보란 노르말헥산 용액을 수득하였다. 그 후 용액을 -30℃로 냉각 후 리튬 디메틸아마이드 130g(2.56mol)을 2시간에 걸쳐 천천히 주입하였다.In a flame-dried 3000 ml flask, 2000 ml of n-hexane was introduced under a nitrogen atmosphere, and after cooling at -30 ° C, 300 g (2.56 mol) of trichloroborane (BCl 3) was added. Then, 570 g (5.63 mol) of triethylamine was added slowly over 1 hour, the temperature was raised to 25 ° C, and the mixture was stirred for 1 hour. After stirring, the temperature was raised to 40 캜, and 225.7 g (2.56 mol) of N, N'-dimethylethylenediamine was slowly added over 3 hours. Thereafter, the mixture was stirred at a temperature of 40 ° C-50 ° C for 12 hours. Filtration of the by-product (TEA HCl) yielded a solution of 1,3-dimethyl-2-chloro-1,3,2-diazaborane in n-hexane. Thereafter, the solution was cooled to -30 캜, and 130 g (2.56 mol) of lithium dimethylamide was slowly injected over 2 hours.
주입 후 25℃ 까지 온도를 올린 후 10시간동안 교반시켰다. 교반 후 불순물로 LiCl을 걸러 거른 용액을 진공을 이용하여 용매를 제거하였다. 용매를 제거한 후 남은 액체를 순도를 높이기 위해 감압 하에서 증류(34℃, 3.0mmHg)하여 무색 액체의 표제 화합물 180.5g(수율 50%)을 수득하였다.After the injection, the temperature was raised to 25 DEG C and stirred for 10 hours. After stirring, LiCl was filtered out as an impurity and the solvent was removed by using a vacuum. After removing the solvent, the remaining liquid was distilled under reduced pressure (34 DEG C, 3.0 mmHg) to increase the purity to obtain 180.5 g (yield 50%) of the title compound as a colorless liquid.
1H NMR (C6D6): δ 2.53(6H), 2.62(6H), 2.98(4H), 1 H NMR (C 6 D 6 ):? 2.53 (6H), 2.62 (6H), 2.98 (4H)
[실시예 2] 붕소함유 박막의 제조[Example 2] Production of boron-containing thin film
플라즈마 화학기상증착법(Plasma Enhancement CVD)에 의해 실리콘 기판 온도 400℃, 챔버 내 공정압력 2Torr에서 실시예 1의 붕소함유 화합물을 증기 상태로 주입하여 기판 위에 붕소함유 박막을 형성하였다. 증착 시 붕소함유 화합물을 운반하는 아르곤 가스 100sccm, 반응 가스로 암모니아(NH3)가스 80sccm과 질소(N2)가스 20sccm, RF 파워 500W를 인가하여 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing compound of Example 1 was injected in a vapor state at a silicon substrate temperature of 400 DEG C and a chamber pressure of 2 Torr by a plasma enhanced chemical vapor deposition (CVD) method to form a boron-containing thin film on the substrate. A boron-containing thin film was deposited by applying an argon gas for transporting a boron-containing compound at a deposition rate of 100 sccm, an ammonia (NH 3 ) gas of 80 sccm as a reaction gas, a nitrogen (N 2 ) gas of 20 sccm and an RF power of 500 W, The film showed the deposition rate and optical properties (refractive index, extinction coefficient) as shown in Table 1.
도 4는 실시예 2에 따라 실리콘 기판 상에 증착된 붕소함유 박막을 적외선 분광계 분석을 통하여 증착된 박막을 분석하였다. 상기와 같이 형성된 박막은 붕소함유 박막이 형성된 것으로 나타났으며, 수분과의 흡습에 의한 O-H 피크는 관찰되지 않았다. FIG. 4 is a diagram illustrating a thin film deposited on a silicon substrate according to Example 2 through infrared spectrometry analysis of a thin film containing boron. FIG. The thin film formed as described above showed a thin film containing boron, and no O-H peak due to moisture absorption with moisture was observed.
도 5는 실시예 2에 따라 실리콘 기판 상에 증착된 붕소함유 박막의 오제이전자분광기 스펙트럼을 나타낸 도면이며, 상기와 같이 형성된 붕소함유 박막은 붕소(B) 49%, 질소(N) 44%, 탄소(C) 5%, 산소(O) 2%의 조성을 갖는 것으로 관찰되었다.5 is a graph showing the OJS spectra of a boron-containing thin film deposited on a silicon substrate according to Example 2. The boron-containing thin film formed as described above contains 49% of boron (B), 44% of nitrogen (N) (C) 5%, and oxygen (O) 2%.
[실시예 3] 붕소함유 박막의 제조[Example 3] Production of boron-containing thin film
반응 가스를 암모니아(NH3) 50sccm, 질소(N2)50sccm으로 한 것을 제외하고는 실시예 2와 동일하게 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing thin film was deposited in the same manner as in Example 2 except that the reaction gas was 50 sccm of ammonia (NH 3 ) and 50 sccm of nitrogen (N 2 ). The boron-containing thin film formed as described above had a deposition rate Optical properties (refractive index, extinction coefficient).
[실시예 4] 붕소함유 박막의 제조[Example 4] Production of boron-containing thin film
반응 가스를 암모니아(NH3) 20sccm, 질소(N2) 80sccm으로 한 것을 제외하고는 실시예 2와 동일하게 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing thin film was deposited in the same manner as in Example 2 except that the reaction gas was changed to 20 sccm of ammonia (NH 3 ) and 80 sccm of nitrogen (N 2 ). The boron-containing thin film formed as described above had a deposition rate Optical properties (refractive index, extinction coefficient).
[실시예 5] 붕소함유 박막의 제조[Example 5] Production of boron-containing thin film
공정 압력을 1.5Torr로 한 것을 제외하고는 실시예 2와 동일하게 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing thin film was deposited in the same manner as in Example 2 except that the process pressure was set to 1.5 Torr. The boron-containing thin film thus formed exhibited the deposition rate and optical characteristics (refractive index, extinction coefficient) as shown in Table 1.
[실시예 6] 붕소함유 박막의 제조[Example 6] Production of boron-containing thin film
공정 압력을 1.2Torr로 한 것을 제외하고는 실시예 2와 동일하게 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing thin film was deposited in the same manner as in Example 2 except that the process pressure was 1.2 Torr. The boron-containing thin film thus formed exhibited the deposition rate and optical characteristics (refractive index, extinction coefficient) as shown in Table 1.
[실시예 7] 붕소함유 박막의 제조[Example 7] Production of boron-containing thin film
공정 압력을 1Torr로 한 것을 제외하고는 실시예 2와 동일하게 붕소함유 박막을 증착하였으며, 상기와 같이 형성된 붕소함유 박막은 표 1과 같이 증착률 및 광특성(굴절률, 흡광계수)을 보였다.The boron-containing thin film was deposited in the same manner as in Example 2 except that the process pressure was 1 Torr. The boron-containing thin film thus formed exhibited the deposition rate and optical characteristics (refractive index, extinction coefficient) as shown in Table 1.
하기 표 1에 실시예 2 내지 7에 따라 증착된 붕소함유 박막의 증착률 및 광특성(굴절률, 흡광계수)을 나타내었다.The deposition rates and optical characteristics (refractive index, extinction coefficient) of the boron-containing thin films deposited according to Examples 2 to 7 are shown in Table 1 below.
(sccm)NH 3
(sccm)
(sccm)N 2
(sccm)
압력
(Torr)fair
pressure
(Torr)
(Å/min)Deposition rate
(Å / min)
(@248㎚)Refractive index
(@ 248 nm)
(@248㎚)Extinction coefficient
(@ 248 nm)
상기 표 1에서 보이는 바와 같이 본 발명에 따른 붕소함유 박막은 고투명성 박막 특성을 갖는 것을 알 수 있다.As shown in Table 1, the boron-containing thin film according to the present invention has a high transparency thin film characteristic.
Claims (7)
[화학식 1]
[상기 화학식 1에서,
상기 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있으며;
n은 1 내지 9의 정수이다.] 1. A composition comprising a boron-containing compound represented by the following formula (1).
[Chemical Formula 1]
[In the above formula (1)
Wherein R 1 to R 4 independently represent hydrogen, (C1-C10) alkyl, (C1-C10) alkoxy, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl, R 1 alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl to R 4 is methyl, halogen, trifluoromethyl (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3- C20) heteroaryl; < / RTI >
and n is an integer of 1 to 9.]
상기 화학식 1은 하기 화학식 2로 표시되는 붕소함유 화합물인 조성물.
[화학식 2]
[상기 화학식 2에서,
R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬이며, R1 내지 R4의 알킬, 알콕시, 시클로알킬, 헤테로시클로알킬, 아릴 및 헤테로아릴은 할로겐, 트리플루오로메틸, 아미노, 시아노, 하이드록시, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 및 (C3-C20)헤테로아릴에서 선택되는 하나이상의 치환기로 더 치환될 수 있다.]The method according to claim 1,
(1) is a boron-containing compound represented by the following formula (2).
(2)
[In the formula (2)
R 1 to R 4 are each independently of the other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, Alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl of R 1 to R 4 are independently selected from the group consisting of halogen, trifluoromethyl, (C3-C12) cycloalkyl, (C3-C12) heterocycloalkyl, (C6-C20) aryl and (C3-C20) ) Heteroaryl. ≪ / RTI >
상기 화학식 2에서 R1 내지 R4는 서로 독립적으로 수소, (C1-C10)알킬, (C1-C10)알콕시, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴, (C3-C20)헤테로아릴 또는 (C6-C20)아릴(C1-C10)알킬인 조성물.3. The method of claim 2,
Wherein R 1 to R 4 are independently of each other hydrogen, (C 1 -C 10) alkyl, (C 1 -C 10) alkoxy, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, ) Aryl, (C3-C20) heteroaryl or (C6-C20) aryl (C1-C10) alkyl.
상기 화학식 2에서 R1 및 R2는 서로 독립적으로 (C1-C10)알킬, (C3-C12)시클로알킬, (C3-C12)헤테로시클로알킬, (C6-C20)아릴 또는 (C3-C20)헤테로아릴이며;
R3 및 R4는 서로 독립적으로 (C1-C10)알킬인 조성물.The method of claim 3,
Wherein R 1 and R 2 are independently selected from the group consisting of (C 1 -C 10) alkyl, (C 3 -C 12) cycloalkyl, (C 3 -C 12) heterocycloalkyl, (C 6 -C 20) Aryl;
R 3 and R 4 are independently of each other (C 1 -C 10) alkyl.
상기 화학식 2는 하기구조에서 선택되는 붕소함유 화합물인 조성물.
Wherein the formula (2) is a boron-containing compound selected from the following structures.
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