TWI574988B - 矽烷化聚伸芳基 - Google Patents
矽烷化聚伸芳基 Download PDFInfo
- Publication number
- TWI574988B TWI574988B TW104141371A TW104141371A TWI574988B TW I574988 B TWI574988 B TW I574988B TW 104141371 A TW104141371 A TW 104141371A TW 104141371 A TW104141371 A TW 104141371A TW I574988 B TWI574988 B TW I574988B
- Authority
- TW
- Taiwan
- Prior art keywords
- aryl
- alkyl
- group
- oligomer
- bis
- Prior art date
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- 229920000412 polyarylene Polymers 0.000 title claims description 8
- 239000000178 monomer Substances 0.000 claims description 65
- -1 dimethylmethoxy Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 23
- 150000001345 alkine derivatives Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- FQQOMPOPYZIROF-UHFFFAOYSA-N cyclopenta-2,4-dien-1-one Chemical group O=C1C=CC=C1 FQQOMPOPYZIROF-UHFFFAOYSA-N 0.000 claims description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- VAWGEGHHXBHACH-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(C)(C)C)(C)C Chemical compound CC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(C)(C)C)(C)C VAWGEGHHXBHACH-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- WTXBAYPZJKPZHX-UHFFFAOYSA-N 2-methyldecan-2-ol Chemical compound CCCCCCCCC(C)(C)O WTXBAYPZJKPZHX-UHFFFAOYSA-N 0.000 claims description 4
- IBEFZCQGJJHIDA-UHFFFAOYSA-N COC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(OC)(OC)OC)(OC)OC Chemical compound COC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(OC)(OC)OC)(OC)OC IBEFZCQGJJHIDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- RYMFJEGYAFYEHI-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC(=CC(=C1)C#CCCCCCCCCCC(C)(C)C)C#CCCCCCCCCCC(C)(C)C)(C)C Chemical compound CC(CCCCCCCCCC#CC1=CC(=CC(=C1)C#CCCCCCCCCCC(C)(C)C)C#CCCCCCCCCCC(C)(C)C)(C)C RYMFJEGYAFYEHI-UHFFFAOYSA-N 0.000 claims description 3
- QDPDBELPCUAJQI-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(OC)(C)C)(OC)C Chemical compound CC(CCCCCCCCCC#CC1=CC(=CC=C1)C#CCCCCCCCCCC(OC)(C)C)(OC)C QDPDBELPCUAJQI-UHFFFAOYSA-N 0.000 claims description 3
- JIIJELSSHBLMLM-UHFFFAOYSA-N COC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(OC)(OC)OC)(OC)OC Chemical compound COC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(OC)(OC)OC)(OC)OC JIIJELSSHBLMLM-UHFFFAOYSA-N 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XOXNGAGTJIQXRP-UHFFFAOYSA-N C1(=CC=CC=C1)C#CC(C(OC)(OC)C#CC1=CC=CC=C1)CCCCCCCC Chemical compound C1(=CC=CC=C1)C#CC(C(OC)(OC)C#CC1=CC=CC=C1)CCCCCCCC XOXNGAGTJIQXRP-UHFFFAOYSA-N 0.000 claims description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002679 ablation Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 238000005553 drilling Methods 0.000 claims description 2
- 238000005530 etching Methods 0.000 claims description 2
- 238000001459 lithography Methods 0.000 claims description 2
- 238000001465 metallisation Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- PEVPFVJBSNAHFE-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC=CC=C1)(C)C Chemical compound CC(CCCCCCCCCC#CC1=CC=CC=C1)(C)C PEVPFVJBSNAHFE-UHFFFAOYSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 13
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
- 239000002318 adhesion promoter Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 150000005215 alkyl ethers Chemical class 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- NIEHEMAZEULEKB-UHFFFAOYSA-N ortho-ethylanisole Natural products CCC1=CC=CC=C1OC NIEHEMAZEULEKB-UHFFFAOYSA-N 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
- 238000005698 Diels-Alder reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 2
- SLVLLNWPHDEVTB-UHFFFAOYSA-N 2,3,4-triphenylcyclopenta-2,4-dien-1-one Chemical compound O=C1C=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SLVLLNWPHDEVTB-UHFFFAOYSA-N 0.000 description 2
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 2
- VUDYMATXCXKNSN-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(C)(C)C)(C)C Chemical compound CC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(C)(C)C)(C)C VUDYMATXCXKNSN-UHFFFAOYSA-N 0.000 description 2
- ORPHJMFRFYFBFS-UHFFFAOYSA-N CC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(OC)(C)C)(OC)C Chemical compound CC(CCCCCCCCCC#CC1=CC=C(C=C1)C#CCCCCCCCCCC(OC)(C)C)(OC)C ORPHJMFRFYFBFS-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BOLABFOEWQNYFN-UHFFFAOYSA-N O1CCCC1.C(CC)(=O)OC Chemical compound O1CCCC1.C(CC)(=O)OC BOLABFOEWQNYFN-UHFFFAOYSA-N 0.000 description 2
- FYDILJUKPRKLRZ-UHFFFAOYSA-N O1CCCC1.COC(CCC)=O Chemical compound O1CCCC1.COC(CCC)=O FYDILJUKPRKLRZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000008378 aryl ethers Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910000420 cerium oxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- MSDKIQILHSEFNE-UHFFFAOYSA-N methyl acetate;oxolane Chemical compound COC(C)=O.C1CCOC1 MSDKIQILHSEFNE-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 150000002923 oximes Chemical group 0.000 description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- HRWIFYPHGUZPKB-UHFFFAOYSA-N 1,1,2-trimethoxydodec-1-ene Chemical compound COC(=C(OC)OC)CCCCCCCCCC HRWIFYPHGUZPKB-UHFFFAOYSA-N 0.000 description 1
- KDTWXGUXWNBYGS-UHFFFAOYSA-N 1,2,3,3,4,4-hexamethyl-5H-diazepine Chemical compound CC1(C(N(N(C=CC1)C)C)(C)C)C KDTWXGUXWNBYGS-UHFFFAOYSA-N 0.000 description 1
- QWSJLHMWMAKOHP-UHFFFAOYSA-N 1,2,4-tris(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC(C=C1C#CC=2C=CC=CC=2)=CC=C1C#CC1=CC=CC=C1 QWSJLHMWMAKOHP-UHFFFAOYSA-N 0.000 description 1
- PNXLPYYXCOXPBM-UHFFFAOYSA-N 1,3-diethynylbenzene Chemical compound C#CC1=CC=CC(C#C)=C1 PNXLPYYXCOXPBM-UHFFFAOYSA-N 0.000 description 1
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- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 1
- UNDXPKDBFOOQFC-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UNDXPKDBFOOQFC-UHFFFAOYSA-N 0.000 description 1
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- 241000219495 Betulaceae Species 0.000 description 1
- QZOPUCDXHXZASN-UHFFFAOYSA-M C(C)(=O)[O-].C(C)CC#N.C(C)(C)O[Al+]OC(C)C Chemical compound C(C)(=O)[O-].C(C)CC#N.C(C)(C)O[Al+]OC(C)C QZOPUCDXHXZASN-UHFFFAOYSA-M 0.000 description 1
- XULVBJCAYKQNKY-UHFFFAOYSA-N C(C)OC(=C(OCC)OCC)CCCCCCCCCC Chemical compound C(C)OC(=C(OCC)OCC)CCCCCCCCCC XULVBJCAYKQNKY-UHFFFAOYSA-N 0.000 description 1
- FAGSQGBCQDFFBH-UHFFFAOYSA-N CCCCCCCCC(C#CC1=CC=CC=C1)C(C)(C)C#CC2=CC=CC=C2 Chemical compound CCCCCCCCC(C#CC1=CC=CC=C1)C(C)(C)C#CC2=CC=CC=C2 FAGSQGBCQDFFBH-UHFFFAOYSA-N 0.000 description 1
- PQWZXTDRJHHAMD-UHFFFAOYSA-N COC(CCCCCCCCCC#CC1=CC=CC=C1)(OC)OC Chemical compound COC(CCCCCCCCCC#CC1=CC=CC=C1)(OC)OC PQWZXTDRJHHAMD-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- WMOHXRDWCVHXGS-UHFFFAOYSA-N [La].[Ce] Chemical compound [La].[Ce] WMOHXRDWCVHXGS-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- BCZWPKDRLPGFFZ-UHFFFAOYSA-N azanylidynecerium Chemical compound [Ce]#N BCZWPKDRLPGFFZ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000008367 deionised water Substances 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 230000001376 precipitating effect Effects 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
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- 238000003892 spreading Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/16—Coating compositions based on 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; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/302—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2639—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing elements other than oxygen, nitrogen or sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
- C08L65/02—Polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
- C09D165/02—Polyphenylenes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
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- B32B2457/00—Electrical equipment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
- C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/46—Diels-Alder reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/74—Further polymerisation of the obtained polymers, e.g. living polymerisation to obtain block-copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/80—Functional group cleavage, e.g. removal of side-chains or protective groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Formation Of Insulating Films (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/569,811 US9481810B2 (en) | 2014-12-15 | 2014-12-15 | Silylated polyarylenes |
Publications (2)
| Publication Number | Publication Date |
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| TW201625711A TW201625711A (zh) | 2016-07-16 |
| TWI574988B true TWI574988B (zh) | 2017-03-21 |
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| EP (1) | EP3034487A1 (OSRAM) |
| JP (1) | JP6175480B2 (OSRAM) |
| KR (1) | KR101779401B1 (OSRAM) |
| CN (1) | CN105694005B (OSRAM) |
| TW (1) | TWI574988B (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170009006A1 (en) * | 2015-07-06 | 2017-01-12 | Rohm And Haas Electronic Materials Llc | Polyarylene materials |
| JP6447581B2 (ja) | 2016-06-17 | 2019-01-09 | コベルコ建機株式会社 | 連結ピン引抜用治具、およびクレーン |
| US10790146B2 (en) | 2016-12-05 | 2020-09-29 | Rohm And Haas Electronic Materials Llc | Aromatic resins for underlayers |
| US20180162967A1 (en) * | 2016-12-14 | 2018-06-14 | Rohm And Haas Electronic Materials Llc | Polyarylene resin compositions |
| US20180162992A1 (en) * | 2016-12-14 | 2018-06-14 | Rohm And Haas Electronic Materials Llc | Polyarylene compositions and methods |
| US20180171069A1 (en) * | 2016-12-19 | 2018-06-21 | Rohm And Haas Electronic Materials Llc | Polyarylene resins |
| CN109792003B (zh) * | 2016-12-22 | 2020-10-16 | 广州华睿光电材料有限公司 | 基于狄尔斯-阿尔德反应的可交联聚合物及其在有机电子器件中的应用 |
| KR102540955B1 (ko) * | 2017-03-31 | 2023-06-08 | 스미또모 가가꾸 가부시키가이샤 | 조성물 |
| US11746254B2 (en) * | 2019-11-19 | 2023-09-05 | Rohm And Haas Electronic Materials Llc | Tunable refractive index polymers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050014855A1 (en) * | 1998-11-24 | 2005-01-20 | Bruza Kenneth J. | Composition containing a cross-linkable matrix precursor and a poragen, and a porous matrix prepared therefrom |
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| US5668210A (en) | 1994-10-24 | 1997-09-16 | The Dow Chemical Company | Adhesion promoter and self-priming arylcyclobutene resin compositions |
| CN1103329C (zh) | 1995-09-12 | 2003-03-19 | 陶氏化学公司 | 乙炔基取代的芳族化合物,其合成,聚合物及其用途 |
| US5965679A (en) | 1996-09-10 | 1999-10-12 | The Dow Chemical Company | Polyphenylene oligomers and polymers |
| JP3928263B2 (ja) | 1998-06-09 | 2007-06-13 | Ｊｓｒ株式会社 | フェニレン基含有重合体およびその製造方法 |
| US6184284B1 (en) | 1998-08-24 | 2001-02-06 | The Dow Chemical Company | Adhesion promoter and self-priming resin compositions and articles made therefrom |
| JP2002534546A (ja) | 1999-01-08 | 2002-10-15 | ザ ダウ ケミカル カンパニー | 良好な接着性および靭性を有する低誘電率ポリマーおよび該ポリマーから作製された物品 |
| US6359091B1 (en) | 1999-11-22 | 2002-03-19 | The Dow Chemical Company | Polyarylene compositions with enhanced modulus profiles |
| JP4344903B2 (ja) * | 2000-06-06 | 2009-10-14 | Ｊｓｒ株式会社 | 半導体素子用の層間絶縁膜形成用材料 |
| EP1305356A1 (en) | 2000-07-19 | 2003-05-02 | Dow Global Technologies Inc. | Spin-on-dielectric compositions with coating enhancer |
| KR100411465B1 (ko) * | 2001-10-26 | 2003-12-18 | 한국과학기술연구원 | 폴리페닐렌을 갖는 플로렌계 화합물, 그 중합체 및 이들을포함하는 ｅｌ 소자 |
| WO2004073824A2 (en) | 2003-02-20 | 2004-09-02 | Dow Global Technologies Inc. | Method of synthesis of polyarylenes and the polyarylenes made by such method |
| KR100561699B1 (ko) * | 2003-04-22 | 2006-03-17 | 한국과학기술연구원 | 폴리아릴렌계 화합물과 그 중합체 및 이들을 이용한 ｅｌ소자 |
| US7626059B2 (en) * | 2003-10-21 | 2009-12-01 | Dow Global Technologies Inc. | Multifunctional ethynyl substituted monomers and polyarylene compositions therefrom |
| JP2005232211A (ja) * | 2004-02-17 | 2005-09-02 | Chisso Corp | 架橋ポリフェニレン、その薄膜および薄膜の形成方法 |
| JP2010070618A (ja) * | 2008-09-17 | 2010-04-02 | Fujifilm Corp | 絶縁膜形成用組成物、絶縁膜、および電子デバイス |
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2014
- 2014-12-15 US US14/569,811 patent/US9481810B2/en not_active Expired - Fee Related
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2015
- 2015-11-13 EP EP15194481.6A patent/EP3034487A1/en not_active Withdrawn
- 2015-12-09 TW TW104141371A patent/TWI574988B/zh not_active IP Right Cessation
- 2015-12-10 CN CN201510917120.2A patent/CN105694005B/zh not_active Expired - Fee Related
- 2015-12-11 JP JP2015242137A patent/JP6175480B2/ja not_active Expired - Fee Related
- 2015-12-14 KR KR1020150178669A patent/KR101779401B1/ko not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050014855A1 (en) * | 1998-11-24 | 2005-01-20 | Bruza Kenneth J. | Composition containing a cross-linkable matrix precursor and a poragen, and a porous matrix prepared therefrom |
Non-Patent Citations (1)
| Title |
|---|
| A Controlled, Iterative Synthesis and the Electronic Properties of Oligo[(p-phenyleneethynylene)-alt-(2,5-siloleneethynylene)]s, Andrew J. Boydston , Youshi Yin , and Brian L. Pagenkopf *, J. Am. Chem. Soc., 2004, 126 (33), pp 10350–10354 * |
Also Published As
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| JP2016121131A (ja) | 2016-07-07 |
| EP3034487A1 (en) | 2016-06-22 |
| US20160168419A1 (en) | 2016-06-16 |
| US9481810B2 (en) | 2016-11-01 |
| CN105694005B (zh) | 2018-03-16 |
| CN105694005A (zh) | 2016-06-22 |
| KR20160072806A (ko) | 2016-06-23 |
| JP6175480B2 (ja) | 2017-08-02 |
| KR101779401B1 (ko) | 2017-09-19 |
| TW201625711A (zh) | 2016-07-16 |
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