JP2019176020A - 水素バリア剤、水素バリア膜形成用組成物、水素バリア膜、水素バリア膜の製造方法、及び電子素子 - Google Patents
水素バリア剤、水素バリア膜形成用組成物、水素バリア膜、水素バリア膜の製造方法、及び電子素子 Download PDFInfo
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- 239000001257 hydrogen Substances 0.000 title claims abstract description 131
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- HZEBHPIOVYHPMT-UHFFFAOYSA-N polonium atom Chemical compound [Po] HZEBHPIOVYHPMT-UHFFFAOYSA-N 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
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- 229920006393 polyether sulfone Polymers 0.000 description 1
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- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical class COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000006679 α-naphthoxycarbonyl group Chemical group 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000006680 β-naphthoxycarbonyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/18—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
電子素子が有機EL素子である場合、機能性膜としては、例えば、パッシベーション膜、透明電極膜、透明絶縁層、平坦化膜、有機発光膜、保護膜等が挙げられる。
このように、有機EL素子等の電子素子では、内部での水素の発生により、TFTや金属配線等の部材が悪影響をうける場合がある。
このため、電子素子がもともと備える機能層に配合することによって、機能層に水素バリア性を付与することができる水素バリア剤や、当該水素バリア剤を用いて形成される水素バリア膜が求められている。
なお、本発明の「水素バリア」性能の対象となる“水素”とは、H2分子、Hラジカル、H+(プロトン)の各種成分及び個々の成分の組み合わせからなる混合成分全体の両方を意味する。
で表される化合物からなる、水素バリア剤である。
第2の態様にかかる水素バリア膜形成用組成物であって、基材成分(A)が、アルカリ可溶性樹脂(A1)と、光重合性化合物(A2)とを含み、さらに、光重合開始剤(C)を含む、水素バリア膜形成用組成物を基板上に塗布して塗布膜を形成することと、
塗布膜を露光することと、を含む、水素バリア膜の製造方法である。
水素バリア剤は、下式(1)で表される化合物からなる。水素バリア剤は、種々の材料に配合されることにより種々の物品に水素バリア性を付与する。
上記環式の含窒素脂肪族カチオンとしては、環を構成する原子として窒素原子以外のヘテロ原子(例えば、酸素原子、イオウ原子等)を含んでいてもよい。
上記非環式若しくは環式の含窒素脂肪族カチオンとしては、下記式(2)〜(4)のいずれかで表されるカチオンが好ましい。
置換基を有してもよいシクロアルキル基としては、炭素原子数5以上30以下のシクロアルキル基が好ましい。置換基を有してもよいシクロアルキル基の具体例としては、シクロペンチル基、及びシクロヘキシル基等が挙げられる。
置換基を有してもよいアルキニル基としては、炭素原子数2以上10以下のアルキニル基が好ましい。置換基を有してもよいアルキニル基の具体例としては、エチニル基、プロピニル基、及びプロパルギル基等が挙げられる。
置換基を有してもよいアリール基としては、炭素原子数6以上30以下のアリール基が好ましい。置換基を有してもよいアリール基の具体例としては、フェニル基、ビフェニル基、1−ナフチル基、2−ナフチル基、9−アンスリル基、9−フェナントリル基、1−ピレニル基、5−ナフタセニル基、1−インデニル基、2−アズレニル基、9−フルオレニル基、ターフェニル基、クオーターフェニル基、o−トリル基、m−トリル基、p−トリル基、キシリル基、o−クメニル基、m−クメニル基、p−クメニル基、メシチル基、ペンタレニル基、ビナフタレニル基、ターナフタレニル基、クオーターナフタレニル基、ヘプタレニル基、ビフェニレニル基、インダセニル基、フルオランテニル基、アセナフチレニル基、アセアントリレニル基、フェナレニル基、フルオレニル基、アントリル基、ビアントラセニル基、ターアントラセニル基、クオーターアントラセニル基、アントラキノリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、ナフタセニル基、プレイアデニル基、ピセニル基、ペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、ヘプタフェニル基、ヘプタセニル基、及びピラントレニル基、オバレニル基等が挙げられる。
置換基を有してもよい複素環基としては、窒素原子、酸素原子、硫黄原子、リン原子を含む、芳香族あるいは脂肪族の複素環が好ましい。複素環の具体例としては、チエニル基、ベンゾ[b]チエニル基、ナフト[2,3−b]チエニル基、チアントレニル基、フリル基、ピラニル基、イソベンゾフラニル基、クロメニル基、キサンテニル基、フェノキサチイニル基、2H−ピロリル基、ピロリル基、イミダゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、インドリジニル基、イソインドリル基、3H−インドリル基、インドリル基、1H−インダゾリル基、プリニル基、4H−キノリジニル基、イソキノリル基、キノリル基、フタラジニル基、ナフチリジニル基、キノキサニリル基、キナゾリニル基、シンノリニル基、プテリジニル基、4aH−カルバゾリル基、カルバゾリル基、β−カルボリニル基、フェナントリジニル基、アクリジニル基、ペリミジニル基、フェナントロリニル基、フェナジニル基、フェナルサジニル基、イソチアゾリル基、フェノチアジニル基、イソキサゾリル基、フラザニル基、フェノキサジニル基、イソクロマニル基、クロマニル基、ピロリジニル基、ピロリニル基、イミダゾリジニル基、イミダゾリニル基、ピラゾリジニル基、ピラゾリニル基、ピペリジル基、ピペラジニル基、インドリニル基、イソインドリニル基、キヌクリジニル基、モルホリニル基、及びチオキサントリル基等が挙げられる。
(式(3)中、R21はそれぞれ独立に水素原子、アルキル基又はシクロアルキル基を表し、R22はそれぞれ独立に水素原子、アルキル基、シクロアルキル基、−C(=NR23)−NR23 2(3個のR23はそれぞれ独立に水素原子、アルキル基又はシクロアルキル基)、又は、=C(−NR24 2)2(4個のR24はそれぞれ独立に水素原子又は有機基)を表す。)
R21〜R23についてのシクロアルキル基としては、炭素原子数5以上30以下のシクロアルキル基が好ましい。シクロアルキル基の具体例としては、シクロペンチル基、及びシクロヘキシル基等が挙げられる。
R24についての有機基としては、アルキル基、シクロアルキル基、アラルキル基、及びアリール基等が挙げられる。
式(3)で表されるカチオンとしては、1,2−ジイソプロピル−3−[ビス(ジメチルアミノ)メチレン]グアニジウム、1−メチルビグアニジウム、1−n−ブチルビグアニジウム、1−(2−エチルヘキシル)ビグアニジウム、1−n−オクタデシルビグアニジウム、1,1−ジメチルビグアニジウム、1,1−ジエチルビグアニジウム、1−シクロヘキシルビグアニジウム、2−エチル−1,1,3,3−テトラメチルグアニジウム、1−ベンジルグアニジウム、1,3−ジベンジルグアニジウム、1−ベンジル−2,3−ジメチルグアニジウム、1−フェニルグアニジウム等が挙げられ、1,2−ジイソプロピル−3−[ビス(ジメチルアミノ)メチレン]グアニジウムが好ましい。
R31についての有機基としては、アルキル基、シクロアルキル基、アラルキル基、及びアリール基等が挙げられる。上記アルキル基、上記シクロアルキル基、上記アラルキル基、及び上記アリール基は、置換基を有していてもよい。上記置換基としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等のハロゲン原子;シアノ基;ニトロ基;メトキシ基、エトキシ基、及びtert−ブトキシ基等のアルコキシ基;フェノキシ基、及びp−トリルオキシ基等のアリールオキシ基;アセトキシ基、プロピオニルオキシ基、及びベンゾイルオキシ基等のアシルオキシ基;メトキシカルボニル基、及びブトキシカルボニル基等のアルコキシカルボニル基;フェノキシカルボニル基等のアリールオキシカルボニル基;ビニルオキシカルボニル基、及びアリルオキシカルボニル基等のアルケニルオキシカルボニル基;アセチル基、ベンゾイル基、イソブチリル基、アクリロイル基、メタクリロイル基、及びメトキサリル基等のアシル基;メチルスルファニル基、及びtert−ブチルスルファニル基等のアルキルスルファニル基;フェニルスルファニル基、及びp−トリルスルファニル基等のアリールスルファニル基;メチルアミノ基、及びシクロヘキシルアミノ基等のし脂肪族第二級アミノ基;ジメチルアミノ基、ジエチルアミノ基、モルホリノ基、及びピペリジノ基等の脂肪族第三級アミノ基;フェニルアミノ基、p−トリルアミノ基等の芳香族第二級アミノ基;メチル基、エチル基、tert−ブチル基、及びドデシル基等のアルキル基;フェニル基、p−トリル基、キシリル基、クメニル基、ナフチル基、アンスリル基、フェナントリル基等のアリール基;ヒドロキシ基;カルボキシ基;スルホンアミド基;ホルミル基;メルカプト基;スルホ基;メシル基;p−トルエンスルホニル基;第一級アミノ基;ニトロソ基;トリフルオロメチル基、及びトリクロロメチル基等のハロゲン化アルキル基;トリメチルシリル基;ホスフィニコ基;ホスホノ基;アルキルスルホニル基;アリールスルホニル基;トリアルキルアンモニウム基;ジメチルスルホニウミル基;トリフェニルフェナシルホスホニウミル基等が挙げられる。
sは3以上5以下の整数であることが好ましく、3又は4であることがより好ましい。
R41及びR42は互いに結合して環を形成していてもよい。少なくとも2つのR41は互いに結合して環を形成していてもよい。R43、及びR44は互いに結合して環を形成していてもよい。2つのR43は互いに結合して環を形成していてもよい。少なくとも2つのR45は互いに結合して環を形成していてもよい。少なくとも2つのR46は互いに結合して環を形成していてもよい。少なくとも2つのR47は互いに結合して環を形成していてもよい。R48、及びR49は互いに結合して環を形成していてもよい。少なくとも2つのR48は互いに結合して環を形成していてもよい。少なくとも2つのR50は互いに結合して環を形成していてもよい。少なくとも2つのR51は互いに結合して環を形成していてもよい。少なくとも2つのR52は互いに結合して環を形成していてもよい。)
RH、及びR41〜R52についてのアルキル基としては、直鎖アルキル基であっても、分岐鎖アルキル基であってもよい。当該アルキル基の炭素原子数は特に限定されない。アルキル基の炭素原子数は、1以上20以下が好ましく、1以上10以下がより好ましく、1以上5以下が特に好ましい。
RH、及びR41〜R52についてのアルキル基の具体例としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、tert−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、2−エチル−n−ヘキシル基、n−ノニル基、n−デシル基、n−ウンデシル基、n−ドデシル基、n−トリデシル基、n−テトラデシル基、n−ペンタデシル基、n−ヘキサデシル基、n−ヘプタデシル基、n−オクタデシル基、n−ノナデシル基、及びn−イコシル基が挙げられる。
R41〜R52についてのアルケニル基としては、炭素原子数2以上10以下のアルケニル基が好ましい。アルケニル基の具体例としては、ビニル基、アリル基、及びスチリル基等が挙げられる。
R41〜R52についてのアルキニル基としては、炭素原子数2以上10以下のアルキニル基が好ましい。アルキニル基の具体例としては、エチニル基、プロピニル基、及びプロパルギル基等が挙げられる。
RHの具体例及び好ましい例としては、上述した具体例及び好ましい例と同様のものが挙げられる。
RH及びR53〜R55についてのアルキル基としてはRH、及びR41〜R52についてのアルキル基として上述した具体例及び好ましい例と同様のアルキル基が挙げられる。
R53〜R55についてのシクロアルキル基としてはR41〜R52についてのシクロアルキル基としては上述した具体例及び好ましい例と同様のシクロアルキル基が挙げられる。
R56についてのアルキレン基としては、炭素原子数1以上5以下のアルキレン基が挙げられる。アルキレン基の具体例としては、メチレン基、エチレン基、プロピレン基、及びブチレン基等が挙げられる。
上記典型金属元素としては、アルカリ金属元素(周期表1族のうち水素を除く元素からなる金属元素、例えば、ナトリウム、カリウム)、アルカリ土類金属元素(周期表2族の元素からなる金属元素、例えば、マグネシウム)、周期表12族の元素からなる金属元素(例えば、亜鉛)、周期表13族のうちホウ素を除く元素からなる金属元素(例えば、アルミニウム)、周期表14族のうち炭素、ケイ素を除く元素からなる金属元素(例えば、スズ)、周期表15族のうち窒素、リン、ヒ素を除く元素からなる金属元素(例えば、アンチモン)、周期表16族のうち酸素、硫黄、セレン、テルルを除く元素からなる金属元素(例えば、ポロニウム)が挙げられる。
上記遷移金属元素としては、周期表3〜11族の元素からなる金属元素(例えば、ハフニウム)が挙げられる。
上記半金属元素としては、ホウ素、ケイ素、砒素、セレン、テルル等が挙げられる。
上記金属原子を含む原子団のカチオンとしては、金属原子と非金属原子の両方を含む原子団等が挙げられる。具体的には、[ZrO]2+、[(C2H5O)Al]2+、[(n−C4H9)2Sn−O−Sn(n−C4H9)2]2+等が挙げられる。
−O−R9
(R9は水素原子又は有機基である。)
上記式(1)で表される化合物の製造方法としては特に制限はない。例えば、下記式(10)で表される化合物と、m価の対カチオンXm+を形成し得る塩基とを溶媒中若しくは非溶媒中にて中和反応させることにより上記式(1)で表される化合物を製造することができる。
m価の対カチオンXm+を形成し得る塩基としては、上記式(2)〜(4)のいずれかで表される非環式若しくは環式の含窒素脂肪族カチオン、上記式(5)〜(13)のいずれかで表される含窒素芳香族カチオン、上記式(14)〜(16)のいずれかで表される含窒素脂肪族カチオン、又は典型金属元素、遷移金属元素及び半金属元素からなる群より選択される金属原子のカチオン若しくは上記金属原子を含む原子団のカチオンを形成し得る塩基であることがより好ましい。
上記極性溶媒としては、アルコールが挙げられる。具体的には、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、t−ブタノール等が挙げられる。
加熱下(例えば、40℃以上、好ましくは50℃以上、より好ましくは55℃以上)において、上記式(10)で表される化合物と、上記塩基とを上記溶媒に溶解して混合することができる。
加熱時の温度の上限としては特に制限はないが、上記溶媒の沸点以下であることが好ましい。
非加熱下、上記式(10)で表される化合物又は上記塩基が溶媒に溶解し難い場合であっても、中和反応及び塩形成が進行するに従い溶媒への溶解性も進行し得る。
水素バリア膜形成用組成物は、基材成分(A)と、前述の水素バリア剤(B)とを含む。以下、水素バリア膜形成用組成物に含まれる得る成分と、水素バリア膜形成用組成物として好適な組成物とについて説明する。
基材成分(A)は、水素バリア膜形成用組成物に、そのままで溶融加工法等の周知の方法で所望する形状の膜を製造可能な製膜性か、露光、加熱、水との反応等の処理により所望する形状の膜を製造可能な製膜性を付与する成分である。
基材成分(A)は、水素バリア膜形成用組成物に所望する製膜性を与えることができる材料であれば特に限定されない。
基材成分(A)としては、典型的には高分子化合物からなる樹脂材料、加熱により架橋して高分子化合物を生じたり、加熱により分子内環化等の化学変性が生じたりすることにより硬化する熱硬化性材料、露光により硬化し得る光重合性の化合物、組成物中や雰囲気中の水分により加水分縮合する加水分解縮合性のシラン化合物等が用いられる。
加水分解縮合性のシラン化合物としては、テトラメトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、エチルトリメトキシシラン、メチルトリエトキシラン、エチルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、ジメチルジメトキシシラン、ジエチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン等のアルコキシシラン化合物等が挙げられる。加水分解縮合性シラン化合物は、これらのシラン化合物の部分加水分解縮合物であってもよい。
基材成分(A)のうち、樹脂材料の例としては、ポリアセタール樹脂、ポリアミド樹脂、ポリカーボネート樹脂、ポリエステル樹脂(ポリブチレンテレフタレート、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリアリレート等)、FR−AS樹脂、FR−ABS樹脂、AS樹脂、ABS樹脂、ポリフェニレンオキサイド樹脂、ポリフェニレンサルファイド樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリエーテルエーテルケトン樹脂、フッ素系樹脂、ポリイミド樹脂、ポリアミドイミド樹脂、ポリアミドビスマレイミド樹脂、ポリエーテルイミド樹脂、ポリベンゾオキサゾール樹脂、ポリベンゾチアゾール樹脂、ポリベンゾイミダゾール樹脂、シリコーン樹脂、BT樹脂、ポリメチルペンテン、超高分子量ポリエチレン、FR−ポリプロピレン、(メタ)アクリル樹脂(例えば、ポリメチルメタクリレート等)、及びポリスチレン等が挙げられる。
製膜方法としては、Tダイ法(キャスト法)、インフレーション法、プレス法等の溶融加工法や、溶液を用いるキャスト法等が挙げられる。
キャスト法では、樹脂材料と水素バリア剤(B)とを含む溶液を基板上に塗布又は流涎して溶液からなる膜を形成した後、当該膜から加熱等の方法により溶媒を除去して水素バリア膜が形成される。
樹脂材料を用いて得られた水素バリア膜には、必要に応じて一軸延伸や二軸延伸等の延伸処理が施されてもよい。
また、水素バリア膜形成用組成物がキャスト用の組成物である場合、水素バリア膜形成用組成物は溶剤を含んでいてもよい。溶剤の種類は、樹脂材料の種類に応じて、適宜選択される。
熱硬化性材料としては、従来から広く用いられている種々の熱硬化性樹脂の前駆体材料が挙げられる。熱硬化性樹脂の具体例としては、フェノール樹脂、エポキシ樹脂、オキセタン樹脂、メラミン樹脂、尿素樹脂、不飽和ポリエステル樹脂、アルキド樹脂、ポリウレタン樹脂、ポリイミド樹脂、ポリベンゾオキサゾール樹脂、ポリベンゾイミダゾール樹脂等が挙げられる。
以下、熱硬化性材料について、基材成分(A)として特に好適な前駆体材料について説明する。
エポキシ樹脂前駆体としては、従来から広く知られる種々のエポキシ化合物を用いることができる。かかるエポキシ化合物の分子量は特に限定されない。エポキシ化合物の中では、耐熱性、耐化学薬品性、機械的特性等に優れる水素バリア膜を形成しやすいことから、分子内に2以上のエポキシ基を有する多官能エポキシ化合物が好ましい。エポキシ樹脂前駆体は、単独又は2種以上組み合わせて用いることができる。
基材成分(A)としては、加熱により、分子内での芳香環形成反応、及び/又は分子間での架橋反応を生じさせる樹脂である前駆体樹脂が好ましい。
分子間での架橋反応によれば、樹脂を構成する分子鎖が相互に架橋され、三次元架橋構造が形成される。このため、加熱により架橋反応を生じさせる、分子中に、水酸基、カルボン酸無水物基、カルボキシ基、及びエポキシ基から選択される基を有する樹脂を基材成分(A)として用いると、耐熱性及び機械的特性に優れる水素バリア膜が得られる。
スチレン−マレイン酸共重合体の種類は、本発明の目的を阻害しない範囲で特に限定されない。スチレン−マレイン酸共重合体における、スチレン/マレイン酸の共重合比率(質量比)は、1/9以上9/1以下が好ましく、2/8以上8/1以下がより好ましく、1/1以上8/1以下が特に好ましい。スチレン−マレイン酸共重合体の分子量は特に限定されないが、ポリスチレン換算の質量平均分子量として、1000以上100000以下であるのが好ましく、5000以上12000以下であるのがより好ましい。
エポキシ基含有樹脂を基材成分(A)として用いると、必要に応じて硬化剤や硬化促進剤の存在下に加熱することで、エポキシ基含有樹脂が有するエポキシ基同士が架橋される。その結果、耐熱性や機械的特性に優れる硬化物が得られる。エポキシ基含有樹脂は、エポキシ基を有する分子から構成される樹脂であれば特に限定されない。
また、製膜を容易にするため、水素バリア膜形成用組成物は溶剤を含んでいてもよい。溶剤の種類は、熱硬化性材料の種類に応じて、適宜選択される。
従来知られる感光性組成物には、種々の光硬化性の化合物や、アルカリ可溶性樹脂、露光されることでアルカリに対する溶解性が高まる樹脂等が基材成分(A)として含まれる。
感光性の水素バリア膜形成用組成物は、露光により現像液に対して不溶化するネガ型の感光性組成物であってもよく、露光により現像液に対して可溶化するポジ型の感光性組成物であってもよい。
以下、好適な感光性組成物について説明する。
第1の態様の感光性組成物は、アルカリ可溶性樹脂(A1)、光重合性化合物(A2)、及び光重合開始剤(C)とともに、水素バリア剤(B)、及び有機溶剤を含有するネガ型感光性組成物である。
第1の態様の感光性組成物では、アルカリ可溶性樹脂(A1)と、光重合性化合物(A2)とが基材成分(A)に該当する。
なお、本明細書においてアルカリ可溶性樹脂とは、樹脂濃度20質量%の樹脂溶液(溶媒:プロピレングリコールモノメチルエーテルアセテート)により、膜厚1μmの樹脂膜を基板上に形成し、2.38質量%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液に1分間浸漬した際に、膜厚0.01μm以上溶解する樹脂をいう。
また、上記式(a−1)中、mは、0以上20以下の整数を示す。
なお、本明細書において、「(メタ)アクリル酸」は、アクリル酸とメタクリル酸との両方を意味する。同様に、「(メタ)アクリレート」は、アクリレートとメタクリレートとの両方を意味する。
脂環式基を有するエポキシ基含有不飽和化合物としては、前述の式(a05−1)〜(a05−15)で表される化合物が挙げられる。
脂環式基を有さないエポキシ基含有不飽和化合物としては、グリシジル(メタ)アクリレート、2−メチルグリシジル(メタ)アクリレート、3,4−エポキシブチル(メタ)アクリレート、6,7−エポキシヘプチル(メタ)アクリレート等のエポキシアルキル(メタ)アクリレート;2−グリシジルオキシエチル(メタ)アクリレート、3−グリシジルオキシ−n−プロピル(メタ)アクリレート、4−グリシジルオキシ−n−ブチル(メタ)アクリレート、5−グリシジルオキシ−n−ペンチル(メタ)アクリレート、6−グリシジルオキシ−n−ヘキシル(メタ)アクリレート等のエポキシアルキルオキシアルキル(メタ)アクリレート;α−エチルアクリル酸グリシジル、α−n−プロピルアクリル酸グリシジル、α−n−ブチルアクリル酸グリシジル、α−エチルアクリル酸6,7−エポキシヘプチル等のα−アルキルアクリル酸エポキシアルキルエステル類;o−ビニルベンジルグリシジルエーテル、m−ビニルベンジルグリシジルエーテル、p−ビニルベンジルグリシジルエーテル等のグリシジルエーテル類;等が挙げられる。これらの中でも、共重合反応性、硬化後の樹脂の強度等の点から、グリシジル(メタ)アクリレート、2−メチルグリシジル(メタ)アクリレート、6,7−エポキシヘプチル(メタ)アクリレート、o−ビニルベンジルグリシジルエーテル、m−ビニルベンジルグリシジルエーテル、及びp−ビニルベンジルグリシジルエーテルが好ましい。
これらのエポキシ基含有不飽和化合物は、単独又は2種以上組み合わせて用いることができる。
これらのアルカリ可溶性樹脂を用いる場合、機械的に強度に優れ、基板への密着性に優れる水素バリア膜を形成することができる。
また、不飽和カルボン酸に由来する構成単位と、エポキシ基含有不飽和化合物に由来する構成単位とを有する共重合体におけるエポキシ基の少なくとも一部と、不飽和カルボン酸とを反応させることでも、光重合性化合物(A2)との重合可能部位を有する構成単位を有する共重合体を調製することができる。
単官能モノマーとしては、(メタ)アクリルアミド、メチロール(メタ)アクリルアミド、メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、プロポキシメチル(メタ)アクリルアミド、ブトキシメトキシメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、(メタ)アクリル酸、フマル酸、マレイン酸、無水マレイン酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、クロトン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、tert−ブチルアクリルアミドスルホン酸、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、2−フェノキシ−2−ヒドロキシプロピル(メタ)アクリレート、2−(メタ)アクリロイルオキシ−2−ヒドロキシプロピルフタレート、グリセリンモノ(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ジメチルアミノ(メタ)アクリレート、グリシジル(メタ)アクリレート、2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、フタル酸誘導体のハーフ(メタ)アクリレート等が挙げられる。これらの単官能モノマーは、単独又は2種以上組み合わせて用いることができる。
n1は0以上4以下の整数であり、
n2は0、又は1であり、
Rc2は、置換基を有してもよいフェニル基、又は置換基を有してもよいカルバゾリル基であり、
Rc3は、水素原子、又は炭素原子数1以上6以下のアルキル基である。)
また、Rc7が水素原子であると、透明性が良好となる傾向があり好ましい。なお、Rc7が水素原子であり且つRc10が後述の式(c4a)又は(c4b)で表される基であると透明性はより良好となる傾向がある。
アルキル基が有してもよい置換基は、本発明の目的を阻害しない範囲で特に限定されない。置換基の好適な例としては、シアノ基、ハロゲン原子、環状有機基、及びアルコキシカルボニル基が挙げられる。ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。これらの中では、フッ素原子、塩素原子、臭素原子が好ましい。環状有機基としては、シクロアルキル基、芳香族炭化水素基、ヘテロシクリル基が挙げられる。シクロアルキル基の具体例としては、Rc7がシクロアルキル基である場合の好適な例と同様である。芳香族炭化水素基の具体例としては、フェニル基、ナフチル基、ビフェニリル基、アントリル基、及びフェナントリル基等が挙げられる。ヘテロシクリル基の具体例としては、Rc7がヘテロシクリル基である場合の好適な例と同様である。Rc7がアルコキシカルボニル基である場合、アルコキシカルボニル基に含まれるアルコキシ基は、直鎖状でも分岐鎖状でもよく、直鎖状が好ましい。アルコキシカルボニル基に含まれるアルコキシ基の炭素原子数は、1以上10以下が好ましく、1以上6以下がより好ましい。
−CORc11で表されるアシル基を与えるアシル化剤としては、(Rc11CO)2Oで表される酸無水物や、Rc11COHal(Halはハロゲン原子)で表される酸ハライドが挙げられる。
C.I.ピグメントオレンジ1(以下、「C.I.ピグメントオレンジ」は同様であり、番号のみを記載する。)、5、13、14、16、17、24、34、36、38、40、43、46、49、51、55、59、61、63、64、71、73;
C.I.ピグメントバイオレット1(以下、「C.I.ピグメントバイオレット」は同様であり、番号のみを記載する。)、19、23、29、30、32、36、37、38、39、40、50;
C.I.ピグメントレッド1(以下、「C.I.ピグメントレッド」は同様であり、番号のみを記載する。)、2、3、4、5、6、7、8、9、10、11、12、14、15、16、17、18、19、21、22、23、30、31、32、37、38、40、41、42、48:1、48:2、48:3、48:4、49:1、49:2、50:1、52:1、53:1、57、57:1、57:2、58:2、58:4、60:1、63:1、63:2、64:1、81:1、83、88、90:1、97、101、102、104、105、106、108、112、113、114、122、123、144、146、149、150、151、155、166、168、170、171、172、174、175、176、177、178、179、180、185、187、188、190、192、193、194、202、206、207、208、209、215、216、217、220、223、224、226、227、228、240、242、243、245、254、255、264、265;
C.I.ピグメントブルー1(以下、「C.I.ピグメントブルー」は同様であり、番号のみを記載する。)、2、15、15:3、15:4、15:6、16、22、60、64、66;
C.I.ピグメントグリーン7、C.I.ピグメントグリーン36、C.I.ピグメントグリーン37;
C.I.ピグメントブラウン23、C.I.ピグメントブラウン25、C.I.ピグメントブラウン26、C.I.ピグメントブラウン28;
C.I.ピグメントブラック1、C.I.ピグメントブラック7。
特に、第1の態様の感光性組成物を使用してブラックマトリクスを形成する場合には、ブラックマトリクスの膜厚1μm当たりのOD値が4以上となるように、感光性組成物における遮光剤の量を調整することが好ましい。ブラックマトリクスにおける膜厚1μm当たりのOD値が4以上あれば、液晶表示ディスプレイのブラックマトリクスに用いた場合に、十分な表示コントラストを得ることができる。
第2の態様の感光性組成物は、ポジ型感光性組成物である。第2の態様の感光性組成物が、化学増幅型ポジ型感光性組成物の場合、活性光線又は放射線の照射により酸を発生する酸発生剤(以下、光酸発生剤とも記す。)と、酸の作用によりアルカリに対する溶解性が増大する樹脂(以下、感光性樹脂とも記す。)とを含有する。感光性樹脂組成物は、必要に応じて、アルカリ可溶性樹脂、酸拡散抑制剤、及び有機溶剤等の成分を含んでいてもよい。他の第2の態様の感光性組成物としては、キノンジアジド基含有化合物とノボラックフェノール樹脂等のアルカリ可溶性樹脂(例えば後述のノボラック樹脂(C1)等)を含むポジ型感光性組成物が挙げられる。
以下、第2の態様の感光性組成物において好適に使用される光酸発生剤の好適な例について説明する。
−R27a−(O)a−R28a−(O)b−Y1−R29a・・・(c−5a)
(式(c−5a)中、Y1は、単結合又は炭素原子数1以上4以下のアルカンジイル基である。R27a及びR28aは、それぞれ、ハロゲン原子で置換されてもよい炭素原子数2以上6以下のアルカンジイル基、又はハロゲン原子で置換されてもよい炭素原子数6以上20以下のアリーレン基である。R29aは、ハロゲン原子で置換されてもよい炭素原子数1以上18以下のアルキル基、炭素原子数3以上12以下の脂環式炭化水素基、ハロゲン原子で置換されてもよい炭素原子数6以上20以下のアリール基、ハロゲン原子で置換されてもよい炭素原子数7以上20以下のアラルキル基である。a及びbは、それぞれ0又は1であり、a及びbの少なくとも一方は1である。)
で表される基が挙げられる。
炭素原子数1以上18以下のアルキルチオ基としては、メチルチオ基、エチルチオ基、n−プロピルチオ基、イソプロピルチオ基、n−ブチルチオ基、sec−ブチルチオ基、tert−ブチルチオ基、イソブチルチオ基、n−ペンチルチオ基、イソペンチルチオ基、tert−ペンチルチオ基、n−ヘキシルチオ基、n−ヘプチルチオ基、イソヘプチルチオ基、tert−ヘプチルチオ基、n−オクチルチオ基、イソオクチルチオ基、tert−オクチルチオ基、2−エチルヘキシルチオ基、n−ノニルチオ基、n−デシルチオ基、n−ウンデシルチオ基、n−ドデシルチオ基、n−トリデシルチオ基、n−テトラデシルチオ基、n−ペンタデシルチオ基、n−ヘキサデシルチオ基、n−ヘプタデシルチオ基、及びn−オクタデシルチオ基が挙げられる。
また、当該脂肪族炭化水素基の構造は特に限定されず、直鎖状であっても、分岐鎖状であっても、環状であっても、これらの構造の組み合わせであってもよい。
式(c−5a)において、Y1で表される炭素原子数1以上4以下のアルカンジイル基としては、メチレン基、エタン−1,2−ジイル基、エタン−1,1−ジイル基、プロパン−1,3−ジイル基、プロパン−1,2−ジイル基、ブタン−1,4−ジイル基、ブタン−1,3−ジイル基、ブタン−2,3−ジイル基、ブタン−1,2−ジイル基が挙げられる。
式(c−5a)において、R27a又はR28aで表される炭素原子数2以上6以下のアルカンジイル基としては、エタン−1,2−ジイル基、プロパン−1,3−ジイル基、プロパン−1,2−ジイル基、ブタン−1,4−ジイル基、ブタン−1,3−ジイル基、ブタン−2,3−ジイル基、ブタン−1,2−ジイル基、ペンタン−1,5−ジイル基、ペンタン−1,3−ジイル基、ペンタン−1,4−ジイル基、ペンタン−2,3−ジイル基、ヘキサン−1,6−ジイル基、ヘキサン−1,2−ジイル基、ヘキサン−1,3−ジイル基、ヘキサン−1,4−ジイル基、ヘキサン−2,5−ジイル基、ヘキサン−2,4−ジイル基、ヘキサン−3,4−ジイル基が挙げられる。
また、当該アルコキシ基の酸素原子に隣接しない任意の位置のメチレン基が−CO−で置換された基も好ましい。
当該アルコキシ基が−O−CO−結合、又は−O−CO−NH−結合で中断された基も好ましい。なお、−O−CO−結合及び−O−CO−NH−結合の左端が、アルコキシ基中のナフタル酸母核に近い側である。
さらに、脂環式炭化水素基、複素環基、又はハロゲン原子で置換されてもよく、分岐を有してもよい炭素原子数4以上18以下のアルキルチオ基も、R23a〜R26aとして好ましい。
当該アルキルチオ基の硫黄原子に隣接しない任意の位置のメチレン基が−CO−で置換された基も好ましい。
当該アルキルチオ基が−O−CO−結合、又は−O−CO−NH−結合で中断された基も好ましい。なお、−O−CO−結合及び−O−CO−NH−結合の左端が、アルキルチオ基中のナフタル酸母核に近い側である。
アルコキシ基又はアルキルチオ基を置換する複素環基、又はヘテロシクリルオキシ基に含まれる複素環基としては、上記の複素環から水素原子を1つ除いた基が好ましい。
これらの光酸発生剤は、単独又は2種以上組み合わせて用いることができる。
ノボラック樹脂(B1)としては、下記式(b1)で表される構成単位を含む樹脂を使用することができる。
ポリヒドロキシスチレン樹脂(B2)としては、下記式(b4)で表される構成単位を含む樹脂を使用することができる。
アクリル樹脂(B3)としては、下記式(b5)〜(b7)で表される構成単位を含む樹脂を使用することができる。
脂肪族環式基の具体例としては、モノシクロアルカン、ビシクロアルカン、トリシクロアルカン、テトラシクロアルカン等のポリシクロアルカンから1個以上の水素原子を除いた基が挙げられる。具体的には、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロオクタン等のモノシクロアルカンや、アダマンタン、ノルボルナン、イソボルナン、トリシクロデカン、テトラシクロドデカン等のポリシクロアルカンから1個の水素原子を除いた基が挙げられる。特に、シクロヘキサン、アダマンタンから1個の水素原子を除いた基(さらに置換基を有していてもよい)が好ましい。
アルカリ可溶性樹脂としては、ノボラック樹脂(C1)、ポリヒドロキシスチレン樹脂(C2)、及びアクリル樹脂(C3)からなる群より選ばれる少なくとも1種の樹脂であることが好ましい。
ノボラック樹脂は、例えばフェノール性水酸基を有する芳香族化合物(以下、単に「フェノール類」という。)とアルデヒド類とを酸触媒下で付加縮合させることにより得られる。
上記アルデヒド類としては、例えば、ホルムアルデヒド、フルフラール、ベンズアルデヒド、ニトロベンズアルデヒド、アセトアルデヒド等が挙げられる。
付加縮合反応時の触媒は、特に限定されないが、例えば酸触媒では、塩酸、硝酸、硫酸、蟻酸、シュウ酸、酢酸等が使用される。
ポリヒドロキシスチレン樹脂(C2)を構成するヒドロキシスチレン系化合物としては、p−ヒドロキシスチレン、α−メチルヒドロキシスチレン、α−エチルヒドロキシスチレン等が挙げられる。
さらに、ポリヒドロキシスチレン樹脂(C2)は、スチレン樹脂との共重合体とすることが好ましい。このようなスチレン樹脂を構成するスチレン系化合物としては、スチレン、クロロスチレン、クロロメチルスチレン、ビニルトルエン、α−メチルスチレン等が挙げられる。
アクリル樹脂(C3)としては、エーテル結合を有する重合性化合物から誘導された構成単位、及びカルボキシ基を有する重合性化合物から誘導された構成単位を含むことが好ましい。
含窒素化合物(D1)としては、トリメチルアミン、ジエチルアミン、トリエチルアミン、ジ−n−プロピルアミン、トリ−n−プロピルアミン、トリ−n−ペンチルアミン、トリベンジルアミン、ジエタノールアミン、トリエタノールアミン、n−ヘキシルアミン、n−ヘプチルアミン、n−オクチルアミン、n−ノニルアミン、エチレンジアミン、N,N,N’,N’−テトラメチルエチレンジアミン、テトラメチレンジアミン、ヘキサメチレンジアミン、4,4’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルエーテル、4,4’−ジアミノベンゾフェノン、4,4’−ジアミノジフェニルアミン、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、プロピオンアミド、ベンズアミド、ピロリドン、N−メチルピロリドン、メチルウレア、1,1−ジメチルウレア、1,3−ジメチルウレア、1,1,3,3,−テトラメチルウレア、1,3−ジフェニルウレア、イミダゾール、ベンズイミダゾール、4−メチルイミダゾール、8−オキシキノリン、アクリジン、プリン、ピロリジン、ピペリジン、2,4,6−トリ(2−ピリジル)−S−トリアジン、モルホリン、4−メチルモルホリン、ピペラジン、1,4−ジメチルピペラジン、1,4−ジアザビシクロ[2.2.2]オクタン、ピリジン等を挙げることができる。これらは単独で用いてもよく、2種以上を組み合わせて用いてもよい。
有機カルボン酸、又はリンのオキソ酸若しくはその誘導体(D2)のうち、有機カルボン酸としては、具体的には、マロン酸、クエン酸、リンゴ酸、コハク酸、安息香酸、サリチル酸等が好適であり、特にサリチル酸が好ましい。
第3の態様の感光性組成物は、フェノール性水酸基を有するアルカリ可溶性樹脂、酸架橋性物質、光酸発生剤、水素バリア剤(B)、及び有機溶剤を含有するネガ型感光性組成物である。
ポリヒドロキシスチレン系樹脂は、ヒドロキシスチレンに由来する構成単位を少なくとも有する。
ここで「ヒドロキシスチレン」とは、ヒドロキシスチレン、及びヒドロキシスチレンのα位に結合する水素原子がハロゲン原子、アルキル基、ハロゲン化アルキル基等の他の置換基に置換されたもの、並びにそれらの誘導体のヒドロキシスチレン誘導体(モノマー)を含む概念とする。
「ヒドロキシスチレン誘導体」は、少なくともベンゼン環とこれに結合する水酸基とが維持されており、例えば、ヒドロキシスチレンのα位に結合する水素原子が、ハロゲン原子、炭素原子数1以上5以下のアルキル基、ハロゲン化アルキル基等の他の置換基に置換されたもの、並びにヒドロキシスチレンの水酸基が結合したベンゼン環に、さらに炭素原子数1以上5以下のアルキル基が結合したものや、この水酸基が結合したベンゼン環に、さらに1個以上2個以下の水酸基が結合したもの(このとき、水酸基の数の合計は2以上3以下である。)等を包含するものとする。
ハロゲン原子としては、塩素原子、フッ素原子、臭素原子等が挙げられ、フッ素原子が好ましい。
なお、「ヒドロキシスチレンのα位」とは、特に断りがない限り、ベンゼン環が結合している炭素原子のことをいう。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、フッ素原子が好ましい。
ハロゲン化アルキル基としては、上述した炭素原子数1以上5以下のアルキル基の水素原子の一部又は全部がハロゲン原子で置換された基である。この中でも、水素原子の全部がフッ素原子で置換されたアルキル基が好ましい。また、直鎖状又は分岐鎖状のフッ素化アルキル基が好ましく、トリフルオロメチル基、ヘキサフルオロエチル基、ヘプタフルオロプロピル基、ノナフルオロブチル基等がより好ましく、トリフルオロメチル基(−CF3)が最も好ましい。
Rb1としては、水素原子又はメチル基が好ましく、水素原子がより好ましい。
qは0以上2以下の整数である。これらの中でも0又は1であることが好ましく、工業上は特に0であることが好ましい。
Rb2の置換位置は、qが1である場合にはオルト位、メタ位、パラ位のいずれでもよく、さらに、qが2の場合には任意の置換位置を組み合わせることができる。
pは1以上3以下の整数であり、好ましくは1である。
水酸基の置換位置は、pが1である場合にはオルト位、メタ位、パラ位のいずれでもよいが、容易に入手可能で低価格であることからパラ位が好ましい。さらに、pが2又は3の場合には任意の置換位置を組み合わせることができる。
ここで「スチレンに由来する構成単位」とは、スチレン及びスチレン誘導体(但し、ヒドロキシスチレンは含まない。)のエチレン性二重結合が開裂してなる構成単位を包含すると定義される。
「スチレン誘導体」は、スチレンのα位に結合する水素原子が、ハロゲン原子、アルキル基、ハロゲン化アルキル基等の他の置換基に置換された誘導体、並びにスチレンのフェニル基の水素原子が、炭素原子数1以上5以下のアルキル基等の置換基に置換されている誘導体等を包含すると定義される。
ハロゲン原子としては、塩素原子、フッ素原子、臭素原子等が挙げられ、フッ素原子が好ましい。
なお、「スチレンのα位」とは、特に断りがない限り、ベンゼン環が結合している炭素原子のことをいう。
qは0以上2以下の整数である。これらの中でも0又は1であることが好ましく、工業上は特に0であることが好ましい。
Rb2の置換位置は、qが1である場合にはオルト位、メタ位、パラ位のいずれでもよく、さらに、qが2の場合には任意の置換位置を組み合わせることができる。
これらのフェノール類の中でも、m−クレゾール、p−クレゾールが好ましく、m−クレゾールとp−クレゾールとを併用することがより好ましい。この場合、両者の配合割合を調整することにより、感度等の諸特性を調整することができる。
これらの酸架橋性物質は、単独又は2種以上組み合わせて用いることができる。
これらの化合物は、単独又は2種以上組み合わせて用いることができる。
有機溶剤の含有量は、第3の態様の感光性組成物の固形分濃度が1質量%以上50質量%以下となる量が好ましく、5質量%以上30質量%以下となる量がより好ましい。
第3の態様の感光性組成物は、第1の態様の感光性組成物と同様に、必要に応じて、上記の各種添加剤を含有してもよい。
第4の態様の感光性組成物は、エポキシ化合物、及び水素バリア剤(B)を含有し、さらに任意で有機溶剤を含有してもよい。
有機溶剤を含有する場合の有機溶剤の含有量は、第4の態様の感光性組成物の固形分濃度が1質量%以上50質量%以下となる量が好ましく、5質量%以上30質量%以下となる量がより好ましい。
第5の態様の感光性組成物は、エポキシ基含有ポリカルボン酸樹脂、光酸発生剤、水素バリア剤(B)、及び有機溶剤を含有するネガ型感光性組成物である。
光酸発生剤の含有量は、第5の態様の感光性組成物の固形分に対して0.5質量%以上30質量%以下であることが好ましく、1質量%以上20質量%以下であることがより好ましい。上記の範囲とすることにより、感光性組成物の硬化性が良好になる。
有機溶剤の含有量は、第5の態様の感光性組成物の固形分濃度が1質量%以上50質量%以下となる量が好ましく、5質量%以上30質量%以下となる量がより好ましい。
充填剤の含有量は、各組成物の固形分に対して60質量%以下であることが好ましく、5質量%以上40質量%以下であることがより好ましい。
フ
また、水素バリア膜形成用組成物又は第1〜5の態様の感光性組成物は、任意の添加剤として、1−(N,N−ジ(2−エチルヘキシル)アミノ)メチル−1H−ベンゾトリアゾール、1−(N,N−ジ(2−エチルヘキシル)アミノ)メチル−1H−メチルベンゾトリアゾール、カルボキシベンゾトリアゾール、ベンゾトリアゾール、メチルベンゾトリアゾール、ジハイドロキシプロピルベンゾトリアゾール、ビスアミノメチルベンゾトリアゾール等のベンゾトリアゾール誘導体等を単独又は2種以上組み合わせて用いてもよい。
感光性組成物は、上記の各成分を撹拌機で混合することにより調製される。なお、調製された感光性組成物が均一になるよう、メンブランフィルタ等を用いて濾過してもよい。
以上説明した、水素バリア剤(B)を含む水素バリア膜形成用組成物を用いることにより、水素バリア剤(B)を含む水素バリア膜を形成することができる。
水素バリア膜形成用組成物を基板上に塗布して塗布膜を形成することと、
塗布膜を露光することと、を含む方法により水素バリア膜が製造される。
乾燥方法は特に限定されず、例えば、(1)ホットプレートにて80℃以上120℃以下、好ましくは90℃以上100℃以下の温度にて60秒以上120秒以下の間、プリベークを行う方法、(2)室温にて数時間以上数日以下の間放置する方法、(3)温風ヒータや赤外線ヒータ中に数十分間以上数時間以下の間入れて溶剤を除去する方法等が挙げられる。
露光を位置選択的に行う場合、電磁波は、ポジ型又はネガ型のマスクを介して照射してもよく、直接照射してもよい。露光量は、感光性組成物の組成によっても異なるが、例えば5mJ/cm2以上500mJ/cm2以下程度が好ましい。
露光が位置選択的に行われた場合、露光後の塗布膜を、現像液により現像することによって所望の形状にパターニングされた水素バリア膜が得られる。
現像方法は、特に限定されず、例えば、浸漬法、スプレー法等を用いることができる。現像液としては、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等の有機系の現像液や、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、アンモニア、4級アンモニウム塩等の水溶液が挙げられる。
以上説明した水素バリア膜形成用組成物を用いて形成された水素バリア膜は、パッシベーション膜を備える電子素子において好適に用いられる。
パッシベーション膜は、半導体層等の機能層をイオンやガス等や物理的なダメージ等から保護するために設けられる膜である。
電子素子の好適な具体例としては、LED素子及び有機EL素子等の発光素子と、半導体素子と、太陽電池素子と、固体撮像素子とが挙げられる。
これらの材料の中でも、Si、Al、In、Sn、Zn、及びTiから選ばれる金属の酸化物、窒化物、又は酸窒化物が好ましく、Si、又はAlの酸化物、又は窒化物がより好ましく、特に窒化シリコン(Si窒化物)が好ましい。
これらは、副次的な成分として他の元素を含有していてもよい。例えば、窒化シリコンは水素を含んで水素化窒化シリコンとなっていてもよく、さらに酸素を含んで水素化酸窒化シリコンとなっていてもよい。
Siの酸化物膜、又は窒化物膜は、ポリシラザン、ポリシロキサン、ポリシロキサザン、又はポリシラン等のケイ素含有ポリマー含有組成物の塗膜の焼成による酸化物膜、又は窒化物膜であってもよい。
パッシベーション膜の保護性能の点からは、パッシベーション膜は窒化ケイ素(SiN)を含むのが好ましい。
窒化ケイ素を含むパッシベーション膜は特に水素ガスを発生させやすい。
TFTは、水素ガスとの接触による還元反応により機能が損なわれるおそれがあり、金属配線についても水素ガスによる還元によって電気的特性が変化するおそれがある。
パッシベーション膜から発生する水素ガスを水素バリア膜で遮蔽し、水素ガスによる影響を受ける部材での悪影響の発生を抑制できる。
水素バリア膜は、例えば、TFT等の水素から保護したい対象物と、水素の発生源との間に設けられるのが好ましい。
電子素子の外部環境中に存在する水素が、電子素子内の保護対象物に侵入するおそれがある場合、電子素子が外部環境に触れる面に設けられるハードコート層に水素バリア剤を配合して、水素バリア膜としてもよい。
また、パッシベーション膜等の水素発生源となる膜から発生する水素から、電子素子内のTFT等の保護対象物を保護する場合、水素発生源となる膜と、保護対象物との間に水素バリア膜が形成されるのが好ましい。この場合、例えば、平坦化膜を水素バリア膜としてよい。
1H−NMR(重DMSO,400MHz):カチオンδ(ppm)=3.48(CH2,2H),3.40(CH2,2H),3.15(CH2,2H),2.65(CH2,2H),1.82(CH2,2H),1.70−1.45(CH2,6H)、
アニオンδ(ppm)=7.70(CH,1H),7.22(Ph,2H),7.15(CH,1H),6.85(Ph,2H),6.80(CH,1H),5.63(CH,1H),3.70(CH3,3H),2.85−2.65(CH2,2H)
1H−NMR(重DMSO,400MHz):カチオンδ(ppm)=3.55(CH2,2H),3.40−3.25(CH2,4H),2.81(CH2,2H),2.00(CH2,2H),1.88(CH2,2H)
アニオンδ(ppm)=7.70(CH,1H),7.22(Ph,2H),7.15(CH,1H),6.85(Ph, 2H),6.80(CH,1H),5.63(CH,1H),3.70(CH3,3H),2.85−2.65(CH2,2H)
1H−NMR(重DMSO,400MHz):カチオンδ(ppm)=7.03(CH,2H),7.65(CH,1H)
アニオンδ(ppm)=7.86(CH,1H),7.35(3H),6.99(3H),5.70(CH,1H),3.71(CH3,3H),3.35−3.16(CH2,2H)
*使用X線 :回転対陰極型X線発生源由来CuKα線、45kV−200mA
*走査速度(2θ):4.0°/min
*発散スリット:(2/3)°
*散乱スリット:(2/3)°
その他、パッケージ測定「汎用測定>汎用(集中法)」の標準条件設定による。
1H−NMR(重DMSO,500MHz):カチオンδ(ppm)=9.20(NH,1H),3.27−3.22(6H),3.17−3.15(2H),2.90(CH3,3H),1.92−1.89(2H),1.81−1.79(2H)
アニオンδ(ppm)=7.67(CH,1H),7.21(2H),7.12(1H),6.84(2H),6.79(1H),5.62(CH,1H),3.71(CH3,3H),2.73−2.61(CH2,2H)
1H−NMR(重DMSO,500MHz):カチオンδ(ppm)=10.48(NH,2H),3.22−3.17(4H),3.10−3.07(4H),1.86−1.81(4H)
アニオンδ(ppm)=7.71(CH,1H),7.25(2H),7.17(1H),6.86(2H),6.80(1H),5.65(CH,1H),3.71(CH3,3H),2.87−2.73(CH2,2H)
1H−NMR(重DMSO,500MHz):カチオンδ(ppm)=2.84(6H)
アニオンδ(ppm)=7.67(CH,1H),7.21(2H),7.12(1H),6.85(2H),6.79(1H),5.62(CH,1H),3.71(CH3,3H),2.28−2.64(CH2,2H)
1H−NMR(重DMSO,500MHz):カチオンδ(ppm)=2.63(9H),2.61,9H),
アニオンδ(ppm)=7.65(CH,1H),7.18(2H),7.10(1H),6.84(2H),6.84(1H),5.61(CH,1H),3.71(CH3,3H),2.28−2.64(CH2,2H)
下記構造のアルカリ可溶性樹脂12質量部と、ジペンタエリスリトールヘキサアクリレート6質量部と、下記構造の光重合開始剤1.0質量部と、表面調整剤(BYK−310、ポリエステル変性ポリジメチルシロキサン、ビックケミー・ジャパン株式会社製)0.04質量部と、水素バリア剤(前述の化合物3)2.0質量部とを、混合溶剤中に溶解させて、加工性組成物を得た。
ガス発生量の測定時の加熱は、50℃から280℃まで、10℃/分の速度で昇温させて行った。280℃到達時に加熱を終了した。
これらの気体の発生量(ピーク強度)を表1に示す。
硬化膜が形成されていないSiN基板について、実施例1と同様にして、分子量1の成分(水素ラジカル又は水素イオン)と、分子量2の成分(水素ガス)と、分子量18の成分(水蒸気)との発生量を測定した。
これらの気体の発生量(ピーク強度)を表1に示す。
なお、発生ガス量は、SiN表面からの発生ガス量である。
水素バリア剤を用いないことの他は、実施例1と同様にして感光性組成物を得た。得られた感光組成物を用いて、実施例1と同様にして、SiN基板上に硬化膜を形成した。
硬化膜を備えるSiN基板について、実施例1と同様にして、分子量1の成分(水素ラジカル又は水素イオン)と、分子量2の成分(水素ガス)と、分子量18の成分(水蒸気)との発生量を測定した。
これらの気体の発生量(ピーク強度)を表1に示す。
固形分中の比率が20質量%となるように、感光性組成物に市販のモレキュラーシーブ粉末を加え均一になるよう分散することの他は、実施例1と同様にして感光性組成物を得た。得られた感光組成物を用いて、実施例1と同様にして、SiN基板上に硬化膜を形成した。
硬化膜を備えるSiN基板について、実施例1と同様にして、分子量1の成分(水素ラジカル又は水素イオン)と、分子量2の成分(水素ガス)と、分子量18の成分(水蒸気)との発生量を測定した。
これらの気体の発生量(ピーク強度)を表1に示す。
他方、比較例3と、比較例1及び2との比較によれば、感光性組成物を用いて形成される硬化膜にモレキュラーシーブ等の水素ガスや水を吸着し得る材料を加えても、SiNから発生するガスの透過を、硬化膜によりほとんど抑制できないことが分かる。
[実施例2]
実施例1のアルカリ可溶性樹脂のエポキシ基含有構成単位を、グリシジルメタクリレート由来の構成単位に置き換えた樹脂を用いた他は、実施例1と同様にして、水素バリア膜形成用組成物を得た。
上記構造の水素バリア剤を用いなかった他は、実施例2と同様にして、比較用の膜形成組成物を得た。
実施例1のアルカリ可溶性樹脂のエポキシ基含有構成単位を、3,4−エポキシシクロヘキシルメチルメタアクリレート由来の構成単位に置き換えた樹脂を用いた他は、実施例1と同様にして、水素バリア膜形成用組成物を得た。
上記構造の水素バリア剤を用いなかった他は、実施例3と同様にして、比較用の膜形成組成物を得た。
実施例1の水素バリア剤の添加量を、0.6質量部とした他は、実施例1と同様にして、水素バリア膜形成用組成物を得た。
得られた各硬化膜を備えるSiN基板について、実施例1と同様にして、各ガスの発生量を比較したところ、実施例に係る硬化膜2〜3では、対応する比較硬化膜4〜5よりも、効果的にガスの透過を抑制出来ていた。また実施例に係る硬化膜4においても、比較例2より効果的にガスの透過を抑制出来ていた。
[実施例5]
基材成分として下記式(A−2)で表される化合物を100質量部と、1質量部の下記式(a1−2−1)で表される硬化剤及び10質量部の水素バリア剤(前述の化合物3)とを混合して水素バリア膜形成用組成物を得た。
水素バリア剤を用いなかった他は、実施例5と同様にして、比較用の膜形成組成物を得た。
水素バリア剤を用いなかった他は、実施例6と同様にして、比較用の膜形成組成物を得た。
得られた各硬化膜を備えるSiN基板について、実施例1と同様にして、各ガスの発生量を比較したところ、実施例に係る硬化膜5〜6では、対応する比較硬化膜6〜7よりも、効果的にガスの透過を抑制出来ていた。
[実施例7]
基材成分として、下記式(A−3)及び下記式(A−4)で表される混合樹脂成分(質量比(A−3):(A−4)=70:30)を100質量部、下記式(a1−2−2)で表される硬化剤(ナフタル酸誘導体)を5質量部、水素バリア剤(前述の化合物3)を15質量部を、プロピレングリコールモノメチルエーテルアセテート700質量部を用いて混合して、水素バリア膜形成用組成物を得た。
水素バリア剤を用いなかった他は、実施例7と同様にして、比較用の膜形成組成物を得た。
基材成分として、混合樹脂成分を下記式(A−5)及び下記式(A−6)で表される混合樹脂成分(質量比(A−5):(A−6)=70:30)100質量部とした他は、実施例7と同様にして、水素バリア膜形成用組成物を得た。
水素バリア剤を用いなかった他は、実施例8と同様にして、比較用の膜形成組成物を得た。
得られた各組成物を、SiN基板(シリコンウエハ上にSiN層を有する積層体)上に塗膜した後、塗布膜を80℃120秒間プリベークした。プレベークされた塗布膜を、紫外線硬化機を用いて露光量50mJ/cm2で全面露光(ghi線ブロードバンド)し、塗布膜を硬化させた。露光後の塗布膜を、100℃で20分間ベークすることで、膜厚2.0μmの硬化膜を得た。それぞれ硬化膜7〜8、及び比較硬化膜8〜9とする。
得られた各硬化膜を備えるSiN基板について、実施例1と同様にして、各ガスの発生量を比較したところ、実施例に係る硬化膜7〜8では、対応する比較硬化膜8〜9よりも、効果的にガスの透過を抑制出来ていた。
Claims (8)
- 基材成分(A)と、請求項1に記載の水素バリア剤(B)とを含む、水素バリア膜形成用組成物。
- 前記基材成分(A)が、アルカリ可溶性樹脂(A1)と、光重合性化合物(A2)とを含み、
さらに、光重合開始剤(C)を含む、請求項2に記載の水素バリア膜形成用組成物。 - 請求項1に記載の水素バリア剤(B)を含む、水素バリア膜。
- 請求項3に記載の水素バリア膜形成用組成物の硬化物からなる水素バリア膜。
- 請求項3に記載の水素バリア膜形成用組成物を基板上に塗布して塗布膜を形成することと、
前記塗布膜を露光することと、を含む、水素バリア膜の製造方法。 - パッシベーション膜と、請求項4又は5に記載の水素バリア膜とを含む、電子素子。
- さらに、TFTを含む、請求項7に記載の電子素子。
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US16/362,344 US11142629B2 (en) | 2018-03-28 | 2019-03-22 | Hydrogen barrier agent, hydrogen barrier film forming composition, hydrogen barrier film, method for producing hydrogen barrier film, and electronic element |
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JP7269721B2 (ja) * | 2018-12-12 | 2023-05-09 | 東京応化工業株式会社 | 感エネルギー性樹脂組成物、硬化物及び硬化物の製造方法 |
CN112382827A (zh) * | 2020-11-24 | 2021-02-19 | 河北金力新能源科技股份有限公司 | 具有优良绝缘性能和耐热性能的隔膜及其制备方法 |
CN116200742A (zh) * | 2023-04-25 | 2023-06-02 | 鑫鹏源(聊城)智能科技有限公司 | 钛合金基体用阻氢渗透的复合玻璃质壁垒层及其制备方法和应用 |
CN116200743A (zh) * | 2023-04-25 | 2023-06-02 | 鑫鹏源(聊城)智能科技有限公司 | 不锈钢基体用阻氢渗透的复合玻璃质壁垒层及其制备方法和应用 |
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