KR100843744B1 - 유-무기 복합구조를 갖는 반도체용 절연막 및 이의제조방법 - Google Patents
유-무기 복합구조를 갖는 반도체용 절연막 및 이의제조방법 Download PDFInfo
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- KR100843744B1 KR100843744B1 KR1020070023063A KR20070023063A KR100843744B1 KR 100843744 B1 KR100843744 B1 KR 100843744B1 KR 1020070023063 A KR1020070023063 A KR 1020070023063A KR 20070023063 A KR20070023063 A KR 20070023063A KR 100843744 B1 KR100843744 B1 KR 100843744B1
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 51
- 239000002131 composite material Substances 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 239000004642 Polyimide Substances 0.000 claims abstract description 31
- 229920001721 polyimide Polymers 0.000 claims abstract description 31
- 229920000620 organic polymer Polymers 0.000 claims abstract description 26
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 11
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 10
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 10
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000004693 Polybenzimidazole Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 229920002480 polybenzimidazole Polymers 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920002577 polybenzoxazole Polymers 0.000 claims description 3
- 229920001955 polyphenylene ether Polymers 0.000 claims description 3
- -1 polyquinoxaline Polymers 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 19
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 8
- 239000011147 inorganic material Substances 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 7
- 239000011229 interlayer Substances 0.000 abstract description 5
- 239000010410 layer Substances 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 36
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 11
- 238000001723 curing Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920005575 poly(amic acid) Polymers 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000002861 polymer material Substances 0.000 description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 229910021432 inorganic complex Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical class C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910017059 organic montmorillonite Inorganic materials 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 229920003209 poly(hydridosilsesquioxane) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Formation Of Insulating Films (AREA)
Abstract
Description
실시예 1 | 실시예 2 | 실시예 3 | 실시예 4 | 실시예 5 | 실시예 6 | |
유전상수 | 2.38 | 2.19 | 2.29 | 2.05 | 2.22 | 1.91 |
Claims (13)
- 말단기가 에폭시기로 치환된 다면체 구조의 반응성 실세시퀴옥산이 유기 고분자 내에 분산되어 유-무기 복합구조를 갖는 반도체용 절연막으로서,상기 반응성 실세시퀴옥산이 화학식 1로 표시되는 유-무기 복합구조를 갖는 반도체용 절연막:[화학식 1]R8[Si8O12]상기 식에서, [Si8O12]는 육면체 구조의 옥타실록산이며, R은 에폭시를 갖는 지방족 알킬 그룹이다.
- 삭제
- 제1항에 있어서, 상기 반응성 실세시퀴옥산의 함량은 유기 고분자의 함량을 기준으로 하여 1 내지 25 중량%인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막.
- 제1항에 있어서, 상기 유기 고분자는 폴리이미드(polyimide), 폴리벤즈이미다졸(polybenzimidazole), 폴리퀴녹살린(polyquinoxaline), 방향족 폴리에테르케톤(aromatic polyetherketone) 및 폴리페닐렌에테르(polyphenylene ethers)로 이루어진 군으로부터 선택된 하나 이상인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막.
- 제4항에 있어서, 상기 폴리이미드가 피로메리틱디안하이드리드-코-4,4'-옥시디아닐린 (pyromellitic dianhydride-co-4,4'-oxydianiline:PMDA-ODA) 폴리이미드 또는 비페닐디안하이드리드-코-1,4-페닐렌디아민(biphenyl dianhydride-co-1,4-phenylene diamine:BPDA-PDA) 폴리이미드인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막.
- a) 말단기가 에폭시기로 치환된 다면체 구조를 갖는 반응성 실세시퀴옥산을 형성하는 단계;b) 유기 고분자를 유기 용매에 반응시키고, 상기 a)단계에서 형성된 반응성 실세시퀴옥산을 첨가하여 혼합액을 제조하고 혼합액을 교반하는 단계; 및c) 상기 혼합액을 질소 기류하에서 열경화하는 단계;를 포함하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법.
- 제6항에 있어서, 상기 반응성 실세시퀴옥산은 화학식 1로 표시되는 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법:[화학식 1]R8[Si8O12]상기 식에서, [Si8O12]는 육면체 구조의 옥타실록산이며, R은 에폭시를 갖는 지방족 알킬 그룹이다.
- 제6항에 있어서, 상기 반응성 실세시퀴옥산의 함량은 유기 고분자의 함량을 기준으로 하여 1 내지 25 중량%인 것을 특징으로 하는 유-무기 복합구조의 반도체용 절연막의 제조방법.
- 제6항에 있어서, 상기 반응성 실세시퀴옥산을 형성하는 공정은,a) 옥타비닐펜타사이클로-옥타실록산을 용매에 넣은 후 글리시딜 메타크릴레이트를 첨가하고 교반하는 단계; b) 1-하이드록시사이클로헥실페닐케톤 (HCPK)을 a) 단계의 용액에 넣고 교반하는 단계; c) 상기 b) 단계의 용액에 자외선을 조사하여 옥타비닐펜타사이클로-옥타실록산과 글리시딜 메타크릴레이트가 결합되도록 반응시키는 단계;를 포함하는 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법.
- 제6항에 있어서, 상기 유기 고분자는 폴리이미드(polyimide), 폴리벤즈이미다졸(polybenzimidazole), 폴리퀴녹살린(polyquinoxaline), 폴리벤즈옥사졸 (polybenzoxazole), 방향족 폴리에테르케톤(aromatic polyetherketone) 및 폴리페 닐렌에테르(polyphenylene ethers)로 이루어진 군으로부터 선택된 하나 이상인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법.
- 제6항에 있어서, 상기 폴리이미드가 피로메리틱디안하이드리드-코-4,4'-옥시디아닐린 (pyromellitic dianhydride-co-4,4'-oxydianiline:PMDA-ODA) 폴리이미드 또는 비페닐디안하이드리드-코-1,4-페닐렌디아민(biphenyl dianhydride-co-1,4-phenylene diamine:BPDA-PDA) 폴리이미드인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법.
- 제6항 또는 제9항에 있어서, 상기 용매는 메탄올, 에탄올, 테트라히드로퓨란, 디메틸포름아미드, 메틸에틸케톤, 메틸이소부틸케톤, 및 N-메틸피롤리돈(NMP) 로 이루어진 군에서 선택된 하나 이상인 것을 특징으로 하는 유-무기 복합구조를 갖는 반도체용 절연막의 제조방법.
- 제1항 내지 제5항 중 어느 한 항에 따른 유-무기 복합구조를 갖는 반도체용 절연막을 채용한 것을 특징으로 하는 집적회로세트 디바이스.
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2001189109A (ja) * | 2000-01-05 | 2001-07-10 | Sumitomo Bakelite Co Ltd | 絶縁材用樹脂組成物およびこれを用いた絶縁材 |
KR100397372B1 (ko) * | 2000-09-09 | 2003-09-13 | 학교법인 포항공과대학교 | 다면체 구조의 실세시퀴옥산을 포함하는 저유전재료 및이를 이용한 초저유전박막의 제조방법 |
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JP2001189109A (ja) * | 2000-01-05 | 2001-07-10 | Sumitomo Bakelite Co Ltd | 絶縁材用樹脂組成物およびこれを用いた絶縁材 |
KR100397372B1 (ko) * | 2000-09-09 | 2003-09-13 | 학교법인 포항공과대학교 | 다면체 구조의 실세시퀴옥산을 포함하는 저유전재료 및이를 이용한 초저유전박막의 제조방법 |
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