CN1324908A - 含有乙烯基醚和氨基甲酸酯或脲官能团的小片连接粘合剂 - Google Patents
含有乙烯基醚和氨基甲酸酯或脲官能团的小片连接粘合剂 Download PDFInfo
- Publication number
- CN1324908A CN1324908A CN01119710A CN01119710A CN1324908A CN 1324908 A CN1324908 A CN 1324908A CN 01119710 A CN01119710 A CN 01119710A CN 01119710 A CN01119710 A CN 01119710A CN 1324908 A CN1324908 A CN 1324908A
- Authority
- CN
- China
- Prior art keywords
- vinyl ether
- small pieces
- carbon atom
- line style
- polysiloxane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011230 binding agent Substances 0.000 title claims description 11
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title abstract description 26
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
- 150000003672 ureas Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 37
- -1 vinyl ether compound Chemical class 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 239000011231 conductive filler Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 11
- 230000001070 adhesive effect Effects 0.000 abstract description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 5
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 abstract description 4
- 238000004377 microelectronic Methods 0.000 abstract description 2
- 229960000834 vinyl ether Drugs 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000006471 dimerization reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- SGYAMNNIKRWVKZ-UHFFFAOYSA-N 6-(furan-2-yl)hexa-3,5-dien-2-one Chemical compound CC(=O)C=CC=CC1=CC=CO1 SGYAMNNIKRWVKZ-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229920013649 Paracril Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PSXNDMJWRZYVTM-UHFFFAOYSA-N octanoic acid butyl ester Natural products CCCCCCCC(=O)OCCCC PSXNDMJWRZYVTM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/6715—Unsaturated monofunctional alcohols or amines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/08—Copolymers with vinyl ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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Abstract
同时含有乙烯基醚和氨基甲酸酯、硫代氨基甲酸酯或脲官能团的化合物适用于微电子应用领域并且与不含氨基甲酸酯、硫代氨基甲酸酯或脲官能团的化合物相比具有提高了的粘结强度。
Description
本发明涉及含有包含乙烯基醚和或氨基甲酸酯、硫代氨基甲酸酯或是脲官能团的树脂的小片连接粘合剂。
粘合剂组合物，特别是导电性粘合剂广泛用于制造和组装半导体包封件和微电子器件。更突出的应用为将集成电路片粘结到引线框架或其它基材上，及将电路包封件或元件粘结到印刷电路板上。
现有包含乙烯基醚作为给体化合物的用于低模量粘合剂，特别是用于小片连接应用中的快速固化粘合剂中的电子受体/给体粘合剂。但是，含有市售乙烯基醚的小片连接粘合剂由于这些市售乙烯基醚的挥发性和非极性特性而经常存在粘性差、树脂流淌和流出。因此，需要利用含有极性官能团的乙烯基醚提供改进的小片连接粘合剂以解决这些性能问题。
本发明涉及含有在分子(小分子)或聚合体上包含乙烯基醚和极性官能团如氨基甲酸酯、硫代氨基甲酸酯或脲官能团的树脂的小片连接粘合剂组合物。小片连接粘合剂组合物可包含固化剂和一种或多种填料。
分子或聚合基团可以是支化、线型或环形的烷烃、硅氧烷、聚硅氧烷、C1-C4-烷氧基封端的硅氧烷或聚硅氧烷、聚醚、聚酯、聚氨酯、聚丁二烯、或芳族、多芳族、或杂芳族基团。
在另一个实施方案中，本发明为包含一种或多种极性乙烯基醚化合物和一种或多种可共聚电子受体化合物、及固化剂和一种或多种填料的小片连接粘合剂组合物。用于共聚的适宜电子受体化合物为富马酸酯和马来酸酯，例如马来酸二辛酯、马来酸二丁酯、富马酸二辛酯、富马酸二丁酯。含有丙烯酸酯和马来酰亚胺官能团的树脂或化合物为其它的适宜电子受体材料。
用于本发明小片连接粘合剂组合物中的极性乙烯基醚化合物为具有此处所述结构的化合物：
其中
n为1-6，且优选为1-3；
R1、R2和R3为氢、甲基或乙基，优选R1、R2和R3中的两个为氢而一个为甲基，且更优选全部为氢；
Q为含有1-12个碳原子的烷基或亚烷氧基线型或支化链或在环结构内含有3-10个碳原子的芳环或杂芳环或稠环，其中杂原子可以为N、O或S；
X和Y独立地为O、NR1或S，其中R1如上述，条件是X和Y都不能为氧或硫，并且
Z为其可包括环形部分的支化或线型烷烃、硅氧烷、聚硅氧烷、C1-C4-烷氧基封端的硅氧烷或聚硅氧烷、聚醚、聚酯、聚氨酯、聚丁二烯、或芳族、多芳族、或杂芳族基团。
用于制备的作为Z基团的起始原料可从许多供应商处购得；例如芳族和聚芳烃材料可从BASF或Bayer获得；硅氧烷和聚硅氧烷来自Gelest；聚醚来自BASF；聚酯来自Uniqema或Bayer；聚丁二烯来自Elf-Atochem；聚氨酯来自Bayer或BASF；而支化或线型烷烃来自Uniqema。这些来源中的一些会具有已经被官能化的Z材料以用于与含有包含乙烯基醚基团的起始材料的反应性官能团反应；在其它情况中，专业人员需要将材料官能化以准备与乙烯基醚起始原料反应。
Z的精确组成或分子量对本发明不是关键的并且可根据电子受体化合物的最终用途要求而广泛变化。可以选择Z的组成以在最终配方中给出特定材料性能，如流变性能、亲水或疏水性能、韧性、强度或柔韧性。例如，低水平交联及绕聚合键的自由旋转将赋予化合物柔韧性，而硅氧烷单元的存在将赋予疏水性和柔韧性。分子量和链长度将影响粘度，分子量越高且链长越长，则粘度越高。
这些极性乙烯基醚化合物可由本领域技术人员设计出的各种合成路线制备。一种适宜的方法是通过在分子或聚合体起始材料上乙烯基醚封端的醇、胺或硫醇与共反应性官能团如异氰酸酯之间的缩合或加成反应。乙烯基醚封端的醇及含聚氨酯低聚物的乙烯基醚的合成路线公开于转让给Allied Signal,Inc.的US专利4,749,807、4,751,273和4,775,732。
这些极性乙烯基醚化合物可与电子受体化合物如富马酸酯、马来酸酯、丙烯酸酯及马来酰亚胺共混以共聚形成具有广泛用途的固化粘合剂组合物。适宜的富马酸酯和马来酸酯为例如马来酸二辛酯、马来酸二丁酯、富马酸二辛酯、富马酸二丁酯。适宜的丙烯酸酯众多并且有市售，例如来自Sartomer。适宜的马来酰亚胺易于制备，例如根据Dershem的US专利6,034,194和6,034,195所述方法制备。
本发明的极性乙烯基醚化合物可配制到粘合剂、涂料、铸封料或封装组合物中，特别是配制到用于电子工业应用的组合物中。该组合物可包含一种或多种固化剂和导电或不导电的填料、以及稳定化化合物、粘结促进剂或偶联剂。
一般粘合剂组合物将包含电子给体极性乙烯基醚和电子受体的混合物。电子给体与电子受体的摩尔比通常在1∶2-2∶1范围，但其它范围可适用于特殊的最终用途。选择摩尔比以在最终固化组合物中获得特殊性能属于本领域技术人员无需过分实验的专业技术。对于含有填料的那些组合物，电子给体/受体体系一般以5-30wt％存在于粘合剂组合物中。对于不含填料的组合物，电子给体/受体混合物将是主要的组分。
这些组合物可热或辐射固化。示例性固化剂为以占组合物0.1-10wt％、优选0.1-3.0wt％的量存在的自由基引发剂和光引发剂。优选的自由基引发剂包括过氧化物，如过辛酸丁酯和过氧化二枯基，及偶氮化合物，如2,2’-偶氮二(2-甲基丙腈)和2,2’-偶氮二(2-甲基丁腈)。优选的光引发剂系列是以商标Irgacure由Ciba SpecialtyChemicals出售的。在某些配方中，可能热引发和光引发均需要，例如固化过程可由辐射开始，而在随后加工步骤中通过使用热进行热固化而完成固化。
一般这些组合物将在70-250℃范围内的温度固化，并且固化将在十秒至三小时的时间间隔内进行。每个配方的时间和温度固化曲线将随特殊的电子给体化合物及配方中的其它组分而变化；固化曲线的参数可由本领域技术人员无需过分实验而确定。
示例性导电填料为炭黑、石墨、金、银、铜、铂、钯、镍、铝、碳化硅、一氮化硼、金刚石和矾土。示例性不导电填料为蛭石、云母、钙硅石、碳酸钙、金红石、沙子、玻璃、熔凝硅石、煅制硅石、硫酸钡及卤化乙烯聚合物，如四氟乙烯、三氟乙烯、偏二氟乙烯、氟乙烯、偏二氯乙烯和氯乙烯颗粒。当填料存在时，其量一般占配制剂的70-95wt％。
示例性粘结促进剂或偶联剂为硅烷、硅酸盐酯、金属丙烯酸盐或甲基丙烯酸盐、钛酸盐及含有螯合配位体如膦、硫醇和乙酰乙酸酯的化合物。当偶联剂存在时，其用量最多占电子给体化合物的10wt％，优选用量占0.1-3.0wt％。
配制剂可包含赋予所得固化材料额外柔韧性和韧性的化合物。这种化合物可以是任何Tg为150℃或更小的热固性或热塑性材料并且一般为聚合物材料，如聚丙烯酸酯、聚丁二烯、聚THF(聚合四氢呋喃)、羧基封端的丁腈橡胶及聚丙二醇。当这些化合物存在时，其用量最多可占极性乙烯基醚化合物的约15wt％。
下列实施例给出了代表性极性乙烯基醚化合物、其制备反应及由这些化合物制备的粘合剂配制剂。反应产物通过1H-NMR和FT-IR光谱进行表征。OCN-C36-NCO代表通过油酸和亚油酸二聚然后转化为二异氰酸酯衍生物所得的异构体的混合物。C36代表含有36个碳原子的线型和支链烷基(由亚油酸和油酸二聚所得)的异构体的混合物。
实施例1
在1升装有机械搅拌、加料漏斗和氮气导入/出管的三颈烧瓶中将二聚二异氰酸酯(Henkel,DDI1410)(88.36g,0.147mol)溶解在甲苯(300ml)中。反应置于氮气氛下，并在将溶液加热到80℃时搅拌下加入0.04g二月桂酸二丁基锡(催化剂)。加料漏斗中加入溶解在甲苯(50ml)中的1,4-环己烷二甲醇单乙烯基醚(BASF)(50g,0.294mol)。在10分钟内将该溶液加入到异氰酸酯溶液中，并将所得混合物在80℃再加热3小时。当反应冷却到室温后，用蒸馏水洗涤混合物3次。分离出的有机层经MgSO4干燥、过滤并在真空下除去溶剂得到产率为94％的产物。
实施例2
在500ml装有机械搅拌、加料漏斗和氮气导入/出管的三颈烧瓶中将二聚二异氰酸酯(Henkel,DDI1410)(41.7g,0.069mol)溶解在甲苯(100ml)中。反应置于氮气氛下，并在将溶液加热到80℃时搅拌下加入0.03g二月桂酸二丁基锡(催化剂)。加料漏斗中加入溶解在甲苯(20ml)中的1,6-己醇乙烯基醚(BASF)(20g,0.139mol)。在10分钟内将该溶液加入到异氰酸酯溶液中，并将所得混合物在80℃再加热3小时。当反应冷却到室温后，用蒸馏水洗涤混合物3次。分离出的有机层经MgSO4干燥、过滤并在真空下除去溶剂得到产率为97％的产物。
实施例3
按实施例2进行相同的反应，使用丁醇乙烯基醚替代己醇乙烯基醚。
实施例4
在500ml装有机械搅拌、加料漏斗和氮气导入/出管的三颈烧瓶中将二聚二异氰酸酯(Henkel,DDI1410)(29.74g,0.049mol)溶解在甲苯(200ml)中。反应置于氮气氛下，并将溶液加热到50℃。加料漏斗中加入溶解在甲苯(50ml)中的3-氨基-1-丙醇乙烯基醚(Aldrich)(10g,0.099mol)。在10分钟内将该溶液加入到异氰酸酯溶液中，并将所得混合物在50℃再加热1小时。当反应冷却到室温后，用蒸馏水洗涤混合物3次。分离出的有机层经MgSO4干燥、过滤并在真空下除去溶剂得到产率为96％的产物。
实施例5
该实施例给出了配制到用作小片连接膏的粘合剂中的含有氨基甲酸酯官能团的乙烯基醚化合物的性能特征。
在DSC中使用2wt％的引发剂，来自实施例1和2的极性乙烯基醚化合物及二聚二乙烯基醚(DDVE)，各自以一比一摩尔比与作为电子受体的双马来酰亚胺反应。双马来酰亚胺具有如下结构：
每克含有极性乙烯基醚的配制剂放出的热等于或高于DDVE的，表示聚合程度相似或更大。含有极性乙烯基醚的配制剂的开始至出峰(onset-to-peak)的温度范围也与DDVE基配方的类似或更好，表示类似的固化动力学。结果列于下表中：
| 含有乙烯基醚的小片连接膏的出处 | 开始(℃) | 峰(℃) | 开始至出峰(℃) | ΔH(J/g) |
| 实施例1 | 97.78 | 113.99 | 16.21 | 239.5 |
| 实施例2 | 104.87 | 118.52 | 13.65 | 213.4 |
| DDVE | 101.49 | 119.01 | 17.52 | 207.2 |
以一比一摩尔比使用上述同样的双马来酰亚胺作为电子受体也将来自实施例1和2的乙烯基醚化合物及二聚二乙烯基醚配制到小片连接粘合剂组合物中。专业人员会意识到本说明书中所述的其它电子受体可替代马来酰亚胺。
小片连接粘合剂具有下列配方：
| 组分 | 重量％ |
| 双马来酰亚胺(电子受体) | 11.19 |
| 乙烯基醚(电子给体) | 10.31 |
| 马来酸酐8％(Ricon131) | 2.50 |
| 引发剂 | 0.50 |
| 粘结促进剂共混物 | 0.50 |
| 银屑 | 75.0 |
对上述三个配方(来自实施例1和2的电子受体及DDVE)进行用作小片粘结粘合剂的试验。每个配方分成两份，一份进行室温下粘结强度与电路小片剪切的试验，而第二份进行240℃下的电路小片剪切试验。将三种配方每一个的每份粘合剂配方的等分试样放置在120×120密耳的硅片之间并且各自带有Pd、Ag和Cu引线框。将每个引线框装置放置在200℃的热板上约60秒以固化粘合剂。固化后，在室温和240℃对电路小片侧施压直至出现剪切。以kg为单位测定小片剪切力。结果列于下表中并且显示其中乙烯基醚化合物含有极性官能团的实施例1和2的电路小片剪切值在室温下显示了比不含极性官能团的DDVE更优越的粘结强度。
| 化合物 | 室温电路小片剪切 | 240℃小片剪切 | ||||
| Pd | Ag | Cu | Pd | Ag | Cu | |
| 实施例1 | 13.2kg | 11.1kg | 11.7kg | 4.4kg | 3.8kg | 2.8kg |
| 实施例2 | 10.7kg | 8.6kg | 9.2kg | 4.2kg | 3.7kg | 2.5kg |
| DDVE | 7.0kg | 7.9kg | 7.2kg | 4.0kg | 3.3kg | 2.2kg |
Claims (7)
1．小片连接粘合剂，其包括
(a)5-30wt％含有极性官能团的乙烯基醚化合物和电子受体化合物的混合物，
(b)0.01-10.0wt％自由基引发剂或光引发剂，
(c)70-95wt％导电或不导电填料，
总和为100wt％，其中乙烯基醚具有下列结构：
其中
n为1-6；
R1、R2和R3为氢、甲基或乙基；
Q为含有1-12个碳原子的烷基或环烷基线型或支化链；含有1-12个碳原子的亚烷氧基链，或含有3-10个碳原子并任选还含有O、N或S杂原子的芳环或稠芳环；
X和Y独立地为O、NR1或S，条件是X和Y都不能为氧或硫；
Z为其可包括环形部分的支化或线型烷烃、硅氧烷、聚硅氧烷、C1-C4-烷氧基封端的硅氧烷或聚硅氧烷、聚醚、聚酯、聚氨酯、聚丁二烯、或芳族、多芳族、或杂芳族基团。
2．根据权利要求1的小片连接粘合剂，其中
R1、R2和R3为氢，
Q为含有1-12个碳原子的线型或支链烷基；并且
Z为含有最多36个碳原子的线型或支链烷基。
3．根据权利要求1的小片连接粘合剂，其中填料为银。
4．根据权利要求1的小片连接粘合剂，其中填料为四氟乙烯。
5．具有下列结构的乙烯基醚化合物：
其中
R1、R2和R3独立地为氢、甲基基团或乙基基团；
Q为含有1-12个碳原子的烷基或亚烷氧基线型或支化链；
Z为其可包括环形部分的支化或线型烷烃、硅氧烷、聚硅氧烷、C1-C4-烷氧基封端的硅氧烷或聚硅氧烷、聚醚、聚酯、聚氨酯、聚丁二烯、或芳族、多芳族、或杂芳族基团。
6．根据权利要求5的具有下列结构的乙烯基醚化合物：其中C36为36个碳的线型或支化链的异构体的混合物。
7．包含根据权利要求5的乙烯基醚化合物、自由基引发剂或光引发剂及任选还存在的的导电或不导电填料的粘合剂组合物。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57330300A | 2000-05-18 | 2000-05-18 | |
| US09/573303 | 2000-05-18 |
Publications (2)
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| CN1324908A true CN1324908A (zh) | 2001-12-05 |
| CN1180044C CN1180044C (zh) | 2004-12-15 |
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Family Applications (1)
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| CNB011197102A Expired - Fee Related CN1180044C (zh) | 2000-05-18 | 2001-05-16 | 含有乙烯基醚和氨基甲酸酯或脲官能团的小片连接粘合剂 |
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| US (2) | US20020032260A1 (zh) |
| EP (1) | EP1156068B1 (zh) |
| JP (1) | JP2002047475A (zh) |
| KR (1) | KR100789332B1 (zh) |
| CN (1) | CN1180044C (zh) |
| AT (1) | ATE291048T1 (zh) |
| CA (1) | CA2347872A1 (zh) |
| DE (1) | DE60109356T2 (zh) |
| HK (1) | HK1042316A1 (zh) |
| SG (1) | SG95650A1 (zh) |
| TW (1) | TWI301491B (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104247108A (zh) * | 2012-04-27 | 2014-12-24 | 旭硝子株式会社 | 蓄电装置用粘合剂 |
| CN108028385A (zh) * | 2015-11-23 | 2018-05-11 | 株式会社Lg化学 | 粘附性改善的锂二次电池用电极及其制造方法 |
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| CA2347872A1 (en) * | 2000-05-18 | 2001-11-18 | National Starch And Chemical Investment Holding Corporation | Die attach adhesives with vinyl ether and carbamate or urea functionality |
| US6831132B2 (en) * | 2002-03-28 | 2004-12-14 | Henkel Corporation | Film adhesives containing maleimide compounds and methods for use thereof |
| US20030232926A1 (en) * | 2002-05-14 | 2003-12-18 | Nikolic Nikola A. | Thermoset adhesive films |
| US7176044B2 (en) * | 2002-11-25 | 2007-02-13 | Henkel Corporation | B-stageable die attach adhesives |
| US8513375B2 (en) * | 2003-05-05 | 2013-08-20 | Designer Molecules, Inc. | Imide-linked maleimide and polymaleimide compounds |
| JP5328006B2 (ja) * | 2003-05-05 | 2013-10-30 | デジグナー モレキュールズ インコーポレイテッド | イミド−リンクしたマレインイミドおよびポリマレインイミド化合物 |
| US7884174B2 (en) | 2003-05-05 | 2011-02-08 | Designer Molecules, Inc. | Imide-linked maleimide and polymaleimide compounds |
| ES2426004T3 (es) * | 2004-05-02 | 2013-10-18 | Ashland Licensing And Intellectual Property Llc | Revestimientos curables por radiación para sustratos metálicos de oligómeros multifuncionales de acrilato |
| US20050267254A1 (en) * | 2004-05-28 | 2005-12-01 | Mizori Farhad G | Functionalized urethanes and methods for use thereof |
| US7285613B2 (en) * | 2004-06-04 | 2007-10-23 | Designer Molecules, Inc. | Free-radical curable polyesters and methods for use thereof |
| US7875688B2 (en) * | 2004-06-04 | 2011-01-25 | Designer Molecules, Inc. | Free-radical curable polyesters and methods for use thereof |
| US7875686B2 (en) * | 2004-08-18 | 2011-01-25 | Promerus Llc | Polycycloolefin polymeric compositions for semiconductor applications |
| WO2006049792A1 (en) * | 2004-10-28 | 2006-05-11 | Dow Corning Corporation | Conductive curable compositions |
| JP2006193666A (ja) * | 2005-01-14 | 2006-07-27 | Sumitomo Bakelite Co Ltd | 半導体用接着フィルム、半導体用接着フィルム付きキャリア材料および半導体装置 |
| US20060235137A1 (en) * | 2005-04-18 | 2006-10-19 | Eunsook Chae | Die attach adhesives with improved stress performance |
| KR101368874B1 (ko) * | 2005-09-21 | 2014-03-04 | 다우 코닝 코포레이션 | 오가노보란 아민 착물을 사용하는 주변 조건하의리소그래피 방법 |
| US8043534B2 (en) * | 2005-10-21 | 2011-10-25 | Designer Molecules, Inc. | Maleimide compositions and methods for use thereof |
| EP1837383B1 (en) * | 2006-03-06 | 2008-06-04 | Umicore AG & Co. KG | Die-attach composition for high power semiconductors |
| US20080262191A1 (en) * | 2007-01-26 | 2008-10-23 | Mizori Farhad G | Methods for the preparation of imides, maleimides and maleimide-terminated polyimide compounds |
| US7868113B2 (en) | 2007-04-11 | 2011-01-11 | Designer Molecules, Inc. | Low shrinkage polyester thermosetting resins |
| US8063161B2 (en) * | 2007-04-16 | 2011-11-22 | Designer Molecules, Inc. | Low temperature curing acrylate and maleimide based formulations and methods for use thereof |
| US8308892B2 (en) | 2008-04-09 | 2012-11-13 | Designer Molecules, Inc. | Di-cinnamyl compounds and methods for use thereof |
| US8158748B2 (en) | 2008-08-13 | 2012-04-17 | Designer Molecules, Inc. | Hetero-functional compounds and methods for use thereof |
| US8637611B2 (en) | 2008-08-13 | 2014-01-28 | Designer Molecules, Inc. | Amide-extended crosslinking compounds and methods for use thereof |
| GB201102035D0 (en) * | 2011-02-04 | 2011-03-23 | Zephyros Inc | Improvements in or relating to extrusion |
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| US5334456A (en) * | 1988-08-12 | 1994-08-02 | Stamicarbon B.V. | Free-radical curable compositions |
| AU4432789A (en) * | 1988-11-10 | 1990-05-17 | Loctite (Ireland) Limited | Polymerisable styryloxy resins and compositions thereof |
| US5183946A (en) * | 1989-02-08 | 1993-02-02 | Isp Investments Inc. | Vinyloxy hydroxyalkylcycloalkane and preparation therefor |
| US5084490A (en) * | 1990-12-10 | 1992-01-28 | Loctite (Ireland) Limited | Styryloxy compounds and polymers thereof |
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| ATE195510T1 (de) | 1993-08-09 | 2000-09-15 | Ciba Sc Holding Ag | Neue urethangruppenhaltige (meth)acrylate |
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| US5789757A (en) | 1996-09-10 | 1998-08-04 | The Dexter Corporation | Malemide containing formulations and uses therefor |
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| US5708129A (en) | 1995-04-28 | 1998-01-13 | Johnson Matthey, Inc. | Die attach adhesive with reduced resin bleed |
| US5633411A (en) | 1995-06-07 | 1997-05-27 | Loctite Corporation | Method for production of allyloxystyrene compounds |
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| US6265530B1 (en) * | 1998-07-02 | 2001-07-24 | National Starch And Chemical Investment Holding Corporation | Die attach adhesives for use in microelectronic devices |
| CA2347872A1 (en) * | 2000-05-18 | 2001-11-18 | National Starch And Chemical Investment Holding Corporation | Die attach adhesives with vinyl ether and carbamate or urea functionality |
-
2001
- 2001-05-16 CA CA002347872A patent/CA2347872A1/en not_active Abandoned
- 2001-05-16 KR KR1020010026769A patent/KR100789332B1/ko not_active IP Right Cessation
- 2001-05-16 CN CNB011197102A patent/CN1180044C/zh not_active Expired - Fee Related
- 2001-05-16 SG SG200102949A patent/SG95650A1/en unknown
- 2001-05-16 AT AT01111271T patent/ATE291048T1/de not_active IP Right Cessation
- 2001-05-16 JP JP2001146586A patent/JP2002047475A/ja active Pending
- 2001-05-16 EP EP01111271A patent/EP1156068B1/en not_active Expired - Lifetime
- 2001-05-16 DE DE60109356T patent/DE60109356T2/de not_active Expired - Lifetime
- 2001-05-17 TW TW090112030A patent/TWI301491B/zh not_active IP Right Cessation
- 2001-08-08 US US09/924,321 patent/US20020032260A1/en not_active Abandoned
- 2001-08-10 US US09/927,242 patent/US6699929B2/en not_active Expired - Fee Related
-
2002
- 2002-05-28 HK HK02103967A patent/HK1042316A1/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104247108A (zh) * | 2012-04-27 | 2014-12-24 | 旭硝子株式会社 | 蓄电装置用粘合剂 |
| CN108028385A (zh) * | 2015-11-23 | 2018-05-11 | 株式会社Lg化学 | 粘附性改善的锂二次电池用电极及其制造方法 |
| CN108028385B (zh) * | 2015-11-23 | 2021-06-11 | 株式会社Lg化学 | 粘附性改善的锂二次电池用电极及其制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1180044C (zh) | 2004-12-15 |
| JP2002047475A (ja) | 2002-02-12 |
| KR100789332B1 (ko) | 2007-12-28 |
| DE60109356D1 (de) | 2005-04-21 |
| CA2347872A1 (en) | 2001-11-18 |
| HK1042316A1 (en) | 2002-08-09 |
| EP1156068B1 (en) | 2005-03-16 |
| DE60109356T2 (de) | 2005-07-28 |
| US20020032257A1 (en) | 2002-03-14 |
| US20020032260A1 (en) | 2002-03-14 |
| TWI301491B (en) | 2008-10-01 |
| SG95650A1 (en) | 2003-04-23 |
| ATE291048T1 (de) | 2005-04-15 |
| KR20010106259A (ko) | 2001-11-29 |
| EP1156068A1 (en) | 2001-11-21 |
| US6699929B2 (en) | 2004-03-02 |
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