JP2009531491A - 新規な孔形成前駆体組成物及びそれから得られる多孔誘電層 - Google Patents
新規な孔形成前駆体組成物及びそれから得られる多孔誘電層 Download PDFInfo
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- JP2009531491A JP2009531491A JP2009502025A JP2009502025A JP2009531491A JP 2009531491 A JP2009531491 A JP 2009531491A JP 2009502025 A JP2009502025 A JP 2009502025A JP 2009502025 A JP2009502025 A JP 2009502025A JP 2009531491 A JP2009531491 A JP 2009531491A
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- 239000002243 precursor Substances 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 13
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 13
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- RFFOTVCVTJUTAD-UHFFFAOYSA-N 1,4-cineole Chemical compound C1CC2(C)CCC1(C(C)C)O2 RFFOTVCVTJUTAD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims abstract description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 7
- 239000010703 silicon Substances 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 238000005229 chemical vapour deposition Methods 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000011159 matrix material Substances 0.000 claims description 20
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 claims description 8
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229960005233 cineole Drugs 0.000 claims description 7
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 6
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 claims description 5
- -1 2,4-dimethyl-3-cyclohexenyl group Chemical group 0.000 claims description 5
- 150000004756 silanes Chemical class 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 239000011148 porous material Substances 0.000 abstract description 3
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- 238000010438 heat treatment Methods 0.000 description 6
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 6
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 4
- 229940087305 limonene Drugs 0.000 description 4
- 235000001510 limonene Nutrition 0.000 description 4
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- 230000003647 oxidation Effects 0.000 description 4
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- 239000011343 solid material Substances 0.000 description 4
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- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 238000010849 ion bombardment Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
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- 238000003860 storage Methods 0.000 description 2
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- RFFOTVCVTJUTAD-AOOOYVTPSA-N 1,4-cineole Chemical compound CC(C)[C@]12CC[C@](C)(CC1)O2 RFFOTVCVTJUTAD-AOOOYVTPSA-N 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical group CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007517 polishing process Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
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- 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
- C23C16/56—After-treatment
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- 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
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- 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
- C23C16/401—Oxides containing silicon
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- H01L21/02123—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 characterised by the material of the layer the material containing silicon
- H01L21/02126—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 characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- H01L21/02107—Forming insulating materials on a substrate
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- 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
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
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- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
- H01L21/02274—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition in the presence of a plasma [PECVD]
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
- H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
- H01L21/02337—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to a gas or vapour
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/314—Inorganic layers
- H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
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Abstract
【化1】
Description
または、少なくとも1つの次の孔形成化合物の何れかを含む前駆体混合物に関し、
式(II)の1-メチル-4-(1-メチルエチル)-7-オキサビシクロ[2,2,1]ヘプタン:
または、少なくとも1つの次の孔形成化合物の基板上への低誘電率kの化学気相堆積における孔形成化合物のとしての使用に関する。
Claims (7)
- 珪素、炭素、酸素及び水素原子を有する少なくとも1つの膜母材前駆体化合物と、少なくとも1つの式(I)の孔形成化合物
式(II)の1-メチル-4-(1-メチルエチル)-7-オキサビシクロ[2,2,1]ヘプタン:
- 前記膜母材前駆体化合物が、シロキサン若しくはシラン誘導体から選択される、請求項1又は2記載の方法。
- 前記膜母材前駆体化合物が、TMCT(1,3,5,7-テトラメチルシクロテトラシロキサン)、OMCTS(オクタメチルシクロテトラシロキサン)及びDEOMS(ジエトキシメチルシラン)から選択される、請求項3記載の方法。
- 珪素、炭素、酸素及び水素原子を有する少なくとも1つの膜母材前駆体化合物と、少なくとも1つの式(I)の孔形成化合物(ここで、Rは、直鎖或いは分岐、飽和或いは不飽和炭化水素基若しくは環状飽和或いは不飽和炭化水素基の何れかであり、前記環状或いは非環状基は、1〜4個の炭素原子を有する直鎖或いは分岐アルキル基、1〜4個の炭素原子を有する直鎖或いは分岐アルカノイル基、1〜4個の炭素原子を有する直鎖或いは分岐アルカノイルオキシ基から選ばれる1以上の基により置換されるか置換されないものである。)か、
式(II)の1-メチル-4-(1-メチルエチル)-7-オキサビシクロ[2,2,1]ヘプタン:
- 式(1)の化合物
式(II)の1-メチル-4-(1-メチルエチル)-7-オキサビシクロ[2,2,1]ヘプタン:
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0651126A FR2899379B1 (fr) | 2006-03-31 | 2006-03-31 | Nouveaux precurseurs porogenes et couches dielectriques poreuses obtenues a partir de ceux-ci |
FR0651126 | 2006-03-31 | ||
FR0653576A FR2905517B1 (fr) | 2006-09-05 | 2006-09-05 | Nouveaux precurseurs porogenes et couches dielectriques poreuses obtenues a partir de ceux-ci |
FR0653576 | 2006-09-05 | ||
PCT/EP2007/052661 WO2007113104A1 (en) | 2006-03-31 | 2007-03-20 | Novel pore-forming precursors composition and porous dielectric layers obtained there from |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009531491A true JP2009531491A (ja) | 2009-09-03 |
JP4960439B2 JP4960439B2 (ja) | 2012-06-27 |
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Application Number | Title | Priority Date | Filing Date |
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JP2009502025A Active JP4960439B2 (ja) | 2006-03-31 | 2007-03-20 | 新規な孔形成前駆体組成物及びそれから得られる多孔誘電層 |
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US (1) | US20090136667A1 (ja) |
EP (1) | EP2004872A1 (ja) |
JP (1) | JP4960439B2 (ja) |
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JP5304983B2 (ja) * | 2008-02-12 | 2013-10-02 | Jsr株式会社 | ケイ素含有膜形成用組成物 |
US8298965B2 (en) | 2008-09-03 | 2012-10-30 | American Air Liquide, Inc. | Volatile precursors for deposition of C-linked SiCOH dielectrics |
US8753986B2 (en) | 2009-12-23 | 2014-06-17 | Air Products And Chemicals, Inc. | Low k precursors providing superior integration attributes |
TWI550121B (zh) | 2010-02-17 | 2016-09-21 | 液態空氣喬治斯克勞帝方法研究開發股份有限公司 | SiCOH低K膜之氣相沈積法 |
US20130216859A1 (en) * | 2012-02-20 | 2013-08-22 | Bayer Materialscience Ag | Multilayer assembly as reflector |
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JP2004274052A (ja) * | 2003-03-04 | 2004-09-30 | Air Products & Chemicals Inc | Uv照射による高密度及び多孔質有機ケイ酸塩材料の機械的強化 |
JP2005019980A (ja) * | 2003-05-29 | 2005-01-20 | Air Products & Chemicals Inc | 低誘電率有機ケイ酸塩ガラス膜の作製方法 |
JP2006100833A (ja) * | 2004-09-28 | 2006-04-13 | Air Products & Chemicals Inc | 多孔質の低誘電率組成物並びにそれを作製及び使用するための方法 |
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US6846515B2 (en) * | 2002-04-17 | 2005-01-25 | Air Products And Chemicals, Inc. | Methods for using porogens and/or porogenated precursors to provide porous organosilica glass films with low dielectric constants |
US7384471B2 (en) * | 2002-04-17 | 2008-06-10 | Air Products And Chemicals, Inc. | Porogens, porogenated precursors and methods for using the same to provide porous organosilica glass films with low dielectric constants |
US7727401B2 (en) * | 2004-11-09 | 2010-06-01 | Air Products And Chemicals, Inc. | Selective purification of mono-terpenes for removal of oxygen containing species |
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- 2007-03-20 WO PCT/EP2007/052661 patent/WO2007113104A1/en active Application Filing
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JP2004274052A (ja) * | 2003-03-04 | 2004-09-30 | Air Products & Chemicals Inc | Uv照射による高密度及び多孔質有機ケイ酸塩材料の機械的強化 |
JP2005019980A (ja) * | 2003-05-29 | 2005-01-20 | Air Products & Chemicals Inc | 低誘電率有機ケイ酸塩ガラス膜の作製方法 |
JP2006100833A (ja) * | 2004-09-28 | 2006-04-13 | Air Products & Chemicals Inc | 多孔質の低誘電率組成物並びにそれを作製及び使用するための方法 |
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EP2004872A1 (en) | 2008-12-24 |
JP4960439B2 (ja) | 2012-06-27 |
US20090136667A1 (en) | 2009-05-28 |
WO2007113104A1 (en) | 2007-10-11 |
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