WO2018048297A1 - Organosiloxane hybrid composition for encapsulation of light-emitting elements - Google Patents
Organosiloxane hybrid composition for encapsulation of light-emitting elements Download PDFInfo
- Publication number
- WO2018048297A1 WO2018048297A1 PCT/MY2017/050051 MY2017050051W WO2018048297A1 WO 2018048297 A1 WO2018048297 A1 WO 2018048297A1 MY 2017050051 W MY2017050051 W MY 2017050051W WO 2018048297 A1 WO2018048297 A1 WO 2018048297A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silane
- tetrakis
- cyclopentyloxy
- yloxy
- pyran
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 7
- 238000005538 encapsulation Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 15
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 229910021479 dubnium Inorganic materials 0.000 claims description 11
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 claims description 11
- -1 acetone nitride Chemical class 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 230000003301 hydrolyzing effect Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 7
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 claims description 6
- HRIRIVBGQKMZMI-UHFFFAOYSA-N 2H-pyran-4-yl-tris(2H-thiopyran-4-yloxy)silane Chemical compound S1CC=C(C=C1)O[Si](C1=CCOC=C1)(OC1=CCSC=C1)OC1=CCSC=C1 HRIRIVBGQKMZMI-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- FIYRWDHZSUBZAX-UHFFFAOYSA-N cyclohexyl-tri(cyclooctyloxy)silane Chemical compound C1(CCCCC1)[Si](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 FIYRWDHZSUBZAX-UHFFFAOYSA-N 0.000 claims description 6
- QIKKVFVQXVRHTI-UHFFFAOYSA-N cyclohexyloxy(tricyclopentyl)silane Chemical compound C1(CCCCC1)O[Si](C1CCCC1)(C1CCCC1)C1CCCC1 QIKKVFVQXVRHTI-UHFFFAOYSA-N 0.000 claims description 6
- QEZHKQUOOVJZAQ-UHFFFAOYSA-N cyclohexyloxy-tri(cyclooctyl)silane Chemical compound C1(CCCCC1)O[Si](C1CCCCCCC1)(C1CCCCCCC1)C1CCCCCCC1 QEZHKQUOOVJZAQ-UHFFFAOYSA-N 0.000 claims description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 6
- NUFVQEIPPHHQCK-UHFFFAOYSA-N ethenyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)C=C NUFVQEIPPHHQCK-UHFFFAOYSA-N 0.000 claims description 6
- ZECMUXGNURZWCW-UHFFFAOYSA-N tri(cycloheptyl)-cyclohexyloxysilane Chemical compound C1(CCCCCC1)[Si](OC1CCCCC1)(C1CCCCCC1)C1CCCCCC1 ZECMUXGNURZWCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- VSVVLQJZEVWKMX-UHFFFAOYSA-N cyclohexyl(tricyclopentyloxy)silane Chemical compound C1(CCCCC1)[Si](OC1CCCC1)(OC1CCCC1)OC1CCCC1 VSVVLQJZEVWKMX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- WPICOECJUFIURC-UHFFFAOYSA-N 2H-pyran-4-yl(tripyridin-4-yloxy)silane Chemical compound O1CC=C(C=C1)[Si](OC1=CC=NC=C1)(OC1=CC=NC=C1)OC1=CC=NC=C1 WPICOECJUFIURC-UHFFFAOYSA-N 0.000 claims description 4
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 4
- VULLMAXMBSQEBP-UHFFFAOYSA-N tri(cycloheptyloxy)-cyclohexylsilane Chemical compound C1(CCCCCC1)O[Si](C1CCCCC1)(OC1CCCCCC1)OC1CCCCCC1 VULLMAXMBSQEBP-UHFFFAOYSA-N 0.000 claims description 4
- VMRZXVMMIUSOQP-UHFFFAOYSA-N (pentacyclopentyloxy-lambda6-selanyl)oxycyclopentane Chemical compound C1(CCCC1)O[Se](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 VMRZXVMMIUSOQP-UHFFFAOYSA-N 0.000 claims description 3
- KKQWVFNBNHJSDG-UHFFFAOYSA-N (pentaphenoxy-lambda6-selanyl)oxybenzene Chemical compound O(C1=CC=CC=C1)[Se](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 KKQWVFNBNHJSDG-UHFFFAOYSA-N 0.000 claims description 3
- JBERJPRZLQHENZ-UHFFFAOYSA-N (trimethoxy-lambda4-tellanyl)oxymethane Chemical compound CO[Te](OC)(OC)OC JBERJPRZLQHENZ-UHFFFAOYSA-N 0.000 claims description 3
- IVFSVTFFRZIGCU-UHFFFAOYSA-N 1-(pentapropoxy-lambda6-selanyl)oxypropane Chemical compound C(CC)O[Se](OCCC)(OCCC)(OCCC)(OCCC)OCCC IVFSVTFFRZIGCU-UHFFFAOYSA-N 0.000 claims description 3
- RKILPNJBKQSTLD-UHFFFAOYSA-N 2-ethylbut-1-enyl(methoxy)silane Chemical compound CO[SiH2]C=C(CC)CC RKILPNJBKQSTLD-UHFFFAOYSA-N 0.000 claims description 3
- ANQJVPNQEXFVGG-UHFFFAOYSA-N 2-ethylbut-1-enyl(propoxy)silane Chemical compound C(CC)O[SiH2]C=C(CC)CC ANQJVPNQEXFVGG-UHFFFAOYSA-N 0.000 claims description 3
- SLFWKZACXXSDGO-UHFFFAOYSA-N 2-methylprop-1-enyl(propoxy)silane Chemical compound C(CC)O[SiH2]C=C(C)C SLFWKZACXXSDGO-UHFFFAOYSA-N 0.000 claims description 3
- ZHNBOHUULDVWCY-UHFFFAOYSA-N 2H-pyran-4-yl-(2H-pyran-4-yloxy)-bis(2H-thiopyran-4-yl)silane Chemical compound O1CC=C(C=C1)O[Si](C1=CCSC=C1)(C1=CCSC=C1)C1=CCOC=C1 ZHNBOHUULDVWCY-UHFFFAOYSA-N 0.000 claims description 3
- NQBDGISSOFEGES-UHFFFAOYSA-N 2H-pyran-4-yl-tris(2H-pyran-4-yloxy)silane Chemical compound O1CC=C(C=C1)O[Si](C1=CCOC=C1)(OC1=CCOC=C1)OC1=CCOC=C1 NQBDGISSOFEGES-UHFFFAOYSA-N 0.000 claims description 3
- VGVARNUPWMADBZ-UHFFFAOYSA-N 2H-thiopyran-4-yl-tris(2H-thiopyran-4-yloxy)silane Chemical compound S1CC=C(C=C1)O[Si](C1=CCSC=C1)(OC1=CCSC=C1)OC1=CCSC=C1 VGVARNUPWMADBZ-UHFFFAOYSA-N 0.000 claims description 3
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 claims description 3
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 3
- HGEKXQRHZRDGKO-UHFFFAOYSA-N 3-tripropoxysilylpropyl prop-2-enoate Chemical compound CCCO[Si](OCCC)(OCCC)CCCOC(=O)C=C HGEKXQRHZRDGKO-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- DZDTXXJMHALLJT-UHFFFAOYSA-N C(CC)O[Hf](OCCC)(OCCC)(OCCC)OCCC Chemical compound C(CC)O[Hf](OCCC)(OCCC)(OCCC)OCCC DZDTXXJMHALLJT-UHFFFAOYSA-N 0.000 claims description 3
- CJZPWDYHKUPFIG-UHFFFAOYSA-N C(CC)O[Nb](OCCC)(OCCC)(OCCC)(OCCC)OCCC Chemical compound C(CC)O[Nb](OCCC)(OCCC)(OCCC)(OCCC)OCCC CJZPWDYHKUPFIG-UHFFFAOYSA-N 0.000 claims description 3
- TVRWOYZAPXKPGN-UHFFFAOYSA-N C(CC)O[Se](OCCC)(OCCC)(OCCC)OCCC Chemical compound C(CC)O[Se](OCCC)(OCCC)(OCCC)OCCC TVRWOYZAPXKPGN-UHFFFAOYSA-N 0.000 claims description 3
- WPTRFCFLCBNDKA-UHFFFAOYSA-N C(CCC)O[Se](OCCC)(OCCC)(OCCC)OCCC Chemical compound C(CCC)O[Se](OCCC)(OCCC)(OCCC)OCCC WPTRFCFLCBNDKA-UHFFFAOYSA-N 0.000 claims description 3
- AIKJHPMWNBCNPM-UHFFFAOYSA-N C1(CCCC1)O[Hf](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Hf](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 AIKJHPMWNBCNPM-UHFFFAOYSA-N 0.000 claims description 3
- OBUZNJKTVKLPQO-UHFFFAOYSA-N C1(CCCC1)O[Nb](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Nb](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 OBUZNJKTVKLPQO-UHFFFAOYSA-N 0.000 claims description 3
- KSYKAKGSQDMCQP-UHFFFAOYSA-N C1(CCCC1)O[Nb](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Nb](OC1CCCC1)(OC1CCCC1)OC1CCCC1 KSYKAKGSQDMCQP-UHFFFAOYSA-N 0.000 claims description 3
- XNGDXGWUIFJYDF-UHFFFAOYSA-N C1(CCCC1)O[Rf](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Rf](OC1CCCC1)(OC1CCCC1)OC1CCCC1 XNGDXGWUIFJYDF-UHFFFAOYSA-N 0.000 claims description 3
- LDVUPPKJUZCRIH-UHFFFAOYSA-N C1(CCCC1)O[Ta](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Ta](OC1CCCC1)(OC1CCCC1)OC1CCCC1 LDVUPPKJUZCRIH-UHFFFAOYSA-N 0.000 claims description 3
- LLADBCWDTDFWLZ-UHFFFAOYSA-N C1(CCCC1)O[V](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[V](OC1CCCC1)(OC1CCCC1)OC1CCCC1 LLADBCWDTDFWLZ-UHFFFAOYSA-N 0.000 claims description 3
- LBRXUUYWHPQUOF-UHFFFAOYSA-N C1(CCCC1)[Si](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)[Si](OC1CCCC1)(OC1CCCC1)OC1CCCC1 LBRXUUYWHPQUOF-UHFFFAOYSA-N 0.000 claims description 3
- DGNDLYSXCIKILF-UHFFFAOYSA-N C1(CCCCC1)O[Nb](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 Chemical compound C1(CCCCC1)O[Nb](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 DGNDLYSXCIKILF-UHFFFAOYSA-N 0.000 claims description 3
- CWXYWJZIWPWXLL-UHFFFAOYSA-N C1(CCCCC1)O[Rf](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 Chemical compound C1(CCCCC1)O[Rf](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 CWXYWJZIWPWXLL-UHFFFAOYSA-N 0.000 claims description 3
- QGMSRDZOZJQINA-UHFFFAOYSA-N C1(CCCCC1)O[Ta](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 Chemical compound C1(CCCCC1)O[Ta](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 QGMSRDZOZJQINA-UHFFFAOYSA-N 0.000 claims description 3
- TXELPSMNCXOBLC-UHFFFAOYSA-N C1(CCCCC1)O[V](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 Chemical compound C1(CCCCC1)O[V](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 TXELPSMNCXOBLC-UHFFFAOYSA-N 0.000 claims description 3
- PIKJMKXSEPGCAG-UHFFFAOYSA-N C1(CCCCCC1)O[Nb](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 Chemical compound C1(CCCCCC1)O[Nb](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 PIKJMKXSEPGCAG-UHFFFAOYSA-N 0.000 claims description 3
- SWTSAHMTUKOGQY-UHFFFAOYSA-N C1(CCCCCC1)O[Ta](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 Chemical compound C1(CCCCCC1)O[Ta](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 SWTSAHMTUKOGQY-UHFFFAOYSA-N 0.000 claims description 3
- AQLZWZKCYZKCCZ-UHFFFAOYSA-N C1(CCCCCC1)O[V](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 Chemical compound C1(CCCCCC1)O[V](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 AQLZWZKCYZKCCZ-UHFFFAOYSA-N 0.000 claims description 3
- HLHXWEZIPMVPOM-UHFFFAOYSA-N C1(CCCCCC1)O[Zr](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 Chemical compound C1(CCCCCC1)O[Zr](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 HLHXWEZIPMVPOM-UHFFFAOYSA-N 0.000 claims description 3
- OSVLQBOMIUUICP-UHFFFAOYSA-N C1(CCCCCCC1)O[Nb](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 Chemical compound C1(CCCCCCC1)O[Nb](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 OSVLQBOMIUUICP-UHFFFAOYSA-N 0.000 claims description 3
- SSNNHXJFTIHDNJ-UHFFFAOYSA-N C1(CCCCCCC1)O[V](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 Chemical compound C1(CCCCCCC1)O[V](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 SSNNHXJFTIHDNJ-UHFFFAOYSA-N 0.000 claims description 3
- CVZZDSPVTXGPLO-UHFFFAOYSA-N C1(CCCCCCC1)O[Zr](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 Chemical compound C1(CCCCCCC1)O[Zr](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 CVZZDSPVTXGPLO-UHFFFAOYSA-N 0.000 claims description 3
- XVHPJZMXIGEZKF-UHFFFAOYSA-N C1CCC(C1)O[Ti](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1CCC(C1)O[Ti](OC1CCCC1)(OC1CCCC1)OC1CCCC1 XVHPJZMXIGEZKF-UHFFFAOYSA-N 0.000 claims description 3
- YUXHGAATYJJCAW-UHFFFAOYSA-N C1CCC(C1)O[Zr](OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1CCC(C1)O[Zr](OC1CCCC1)(OC1CCCC1)OC1CCCC1 YUXHGAATYJJCAW-UHFFFAOYSA-N 0.000 claims description 3
- QVFSDFCPKJYIDU-UHFFFAOYSA-N C1CCC(CC1)O[Zr](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 Chemical compound C1CCC(CC1)O[Zr](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 QVFSDFCPKJYIDU-UHFFFAOYSA-N 0.000 claims description 3
- GEYZKHSNKPQEOD-UHFFFAOYSA-N C1CCCC(CC1)O[Ti](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 Chemical compound C1CCCC(CC1)O[Ti](OC1CCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 GEYZKHSNKPQEOD-UHFFFAOYSA-N 0.000 claims description 3
- HWUCXOUOEUYMAJ-UHFFFAOYSA-N C1CCCC(CCC1)O[Ti](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 Chemical compound C1CCCC(CCC1)O[Ti](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 HWUCXOUOEUYMAJ-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- ORZIYGOZOXNZKS-UHFFFAOYSA-I O(C1=CC=CC=C1)[Hf](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)[Hf](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 ORZIYGOZOXNZKS-UHFFFAOYSA-I 0.000 claims description 3
- MCSBIYKAZJFSNU-UHFFFAOYSA-H O(C1=CC=CC=C1)[Nb](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)[Nb](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 MCSBIYKAZJFSNU-UHFFFAOYSA-H 0.000 claims description 3
- UUJNNOQGKSWPEG-UHFFFAOYSA-N O(C1=CC=CC=C1)[Se](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)[Se](OC1=CC=CC=C1)(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1 UUJNNOQGKSWPEG-UHFFFAOYSA-N 0.000 claims description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 3
- SROUYBUBLOMZDE-UHFFFAOYSA-N bis(2H-pyran-4-yl)-bis(2H-pyran-4-yloxy)silane Chemical compound O1CC=C(C=C1)O[Si](C1=CCOC=C1)(C1=CCOC=C1)OC1=CCOC=C1 SROUYBUBLOMZDE-UHFFFAOYSA-N 0.000 claims description 3
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- YINIGTXAPWABHB-UHFFFAOYSA-N cycloheptyl-tri(cyclooctyloxy)silane Chemical compound C1(CCCCCC1)[Si](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 YINIGTXAPWABHB-UHFFFAOYSA-N 0.000 claims description 2
- PMZVUUJJFBLIDG-UHFFFAOYSA-N cyclohexyl(tricyclohexyloxy)silane Chemical compound C1CCCCC1O[Si](C1CCCCC1)(OC1CCCCC1)OC1CCCCC1 PMZVUUJJFBLIDG-UHFFFAOYSA-N 0.000 claims description 2
- UJFGAVKJNDBELS-UHFFFAOYSA-N cyclooctyl(tricyclopentyloxy)silane Chemical compound C1(CCCCCCC1)[Si](OC1CCCC1)(OC1CCCC1)OC1CCCC1 UJFGAVKJNDBELS-UHFFFAOYSA-N 0.000 claims description 2
- ZNCXVGUMNOTGJH-UHFFFAOYSA-N cyclooctyl-tri(cyclooctyloxy)silane Chemical compound C1(CCCCCCC1)[Si](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 ZNCXVGUMNOTGJH-UHFFFAOYSA-N 0.000 claims description 2
- WXBSMVNBLMOCDC-UHFFFAOYSA-N cyclooctyloxy(tricyclopentyl)silane Chemical compound C1(CCCCCCC1)O[Si](C1CCCC1)(C1CCCC1)C1CCCC1 WXBSMVNBLMOCDC-UHFFFAOYSA-N 0.000 claims description 2
- BXUVCTUOUSIUNT-UHFFFAOYSA-N di(cyclooctyl)-di(cyclooctyloxy)silane Chemical compound C1(CCCCCCC1)[Si](OC1CCCCCCC1)(OC1CCCCCCC1)C1CCCCCCC1 BXUVCTUOUSIUNT-UHFFFAOYSA-N 0.000 claims description 2
- RNMQJIRTOAJYER-UHFFFAOYSA-N dicyclohexyl(dicyclohexyloxy)silane Chemical compound C1CCCCC1O[Si](C1CCCCC1)(C1CCCCC1)OC1CCCCC1 RNMQJIRTOAJYER-UHFFFAOYSA-N 0.000 claims description 2
- BFIMXCBKRLYJQO-UHFFFAOYSA-N ethanolate;hafnium(4+) Chemical compound [Hf+4].CC[O-].CC[O-].CC[O-].CC[O-] BFIMXCBKRLYJQO-UHFFFAOYSA-N 0.000 claims description 2
- CGAFRZVAXRQUEI-UHFFFAOYSA-N niobium(5+);propan-1-olate Chemical compound [Nb+5].CCC[O-].CCC[O-].CCC[O-].CCC[O-].CCC[O-] CGAFRZVAXRQUEI-UHFFFAOYSA-N 0.000 claims description 2
- ISBMZZPCHKPNTI-UHFFFAOYSA-N pyridin-4-yl(tripyridin-4-yloxy)silane Chemical compound N1=CC=C(C=C1)[Si](OC1=CC=NC=C1)(OC1=CC=NC=C1)OC1=CC=NC=C1 ISBMZZPCHKPNTI-UHFFFAOYSA-N 0.000 claims description 2
- HLSJAWGOZCTYAC-UHFFFAOYSA-N pyridin-4-yl-tris(2H-thiopyran-4-yloxy)silane Chemical compound S1CC=C(C=C1)O[Si](C1=CC=NC=C1)(OC1=CCSC=C1)OC1=CCSC=C1 HLSJAWGOZCTYAC-UHFFFAOYSA-N 0.000 claims description 2
- NNLHWMYRXASGFA-UHFFFAOYSA-N tri(cycloheptyloxy)-cyclooctylsilane Chemical compound C1(CCCCCC1)O[Si](C1CCCCCCC1)(OC1CCCCCC1)OC1CCCCCC1 NNLHWMYRXASGFA-UHFFFAOYSA-N 0.000 claims description 2
- CLASPBLRSRLCKM-UHFFFAOYSA-N tri(cyclooctyl)-cyclooctyloxysilane Chemical compound C1(CCCCCCC1)[Si](OC1CCCCCCC1)(C1CCCCCCC1)C1CCCCCCC1 CLASPBLRSRLCKM-UHFFFAOYSA-N 0.000 claims description 2
- OSJBHWGUIDLEPC-UHFFFAOYSA-N tri(cyclooctyloxy)-cyclopentylsilane Chemical compound C1(CCCCCCC1)O[Si](C1CCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 OSJBHWGUIDLEPC-UHFFFAOYSA-N 0.000 claims description 2
- OVAJQVNXZKJXEJ-UHFFFAOYSA-N tricyclohexyl(cyclohexyloxy)silane Chemical compound C1(CCCCC1)[Si](OC1CCCCC1)(C1CCCCC1)C1CCCCC1 OVAJQVNXZKJXEJ-UHFFFAOYSA-N 0.000 claims description 2
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 claims description 2
- AGEMWAPSRBMBNP-UHFFFAOYSA-N C1(CCCC1)O[Se](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 Chemical compound C1(CCCC1)O[Se](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1 AGEMWAPSRBMBNP-UHFFFAOYSA-N 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 abstract description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 6
- WJKVFIFBAASZJX-UHFFFAOYSA-N dimethyl(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C)(C)C1=CC=CC=C1 WJKVFIFBAASZJX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- FPIHWRABKKYUOW-UHFFFAOYSA-N C1(CCCC1)O[Se+](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1.[O-]CCC.[Nb+5].[O-]CCC.[O-]CCC.[O-]CCC.[O-]CCC.[O-]CCC Chemical compound C1(CCCC1)O[Se+](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1.[O-]CCC.[Nb+5].[O-]CCC.[O-]CCC.[O-]CCC.[O-]CCC.[O-]CCC FPIHWRABKKYUOW-UHFFFAOYSA-N 0.000 description 1
- MWIINWLWJUEALA-UHFFFAOYSA-N C1(CCCCCCC1)O[Hf](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 Chemical compound C1(CCCCCCC1)O[Hf](OC1CCCCCCC1)(OC1CCCCCCC1)OC1CCCCCCC1 MWIINWLWJUEALA-UHFFFAOYSA-N 0.000 description 1
- MJJKSAAUJDKLSL-UHFFFAOYSA-N CC(C)[O-].CC(C)O.CC(C)O.CC(C)O.CC(C)O.CC(C)O.C(CC1)CC1O[Se+](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1.[SeH2] Chemical compound CC(C)[O-].CC(C)O.CC(C)O.CC(C)O.CC(C)O.CC(C)O.C(CC1)CC1O[Se+](OC1CCCC1)(OC1CCCC1)(OC1CCCC1)OC1CCCC1.[SeH2] MJJKSAAUJDKLSL-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JBHAIXJNXXNJAH-UHFFFAOYSA-N methoxy(2-methylprop-1-enyl)silane Chemical compound CO[SiH2]C=C(C)C JBHAIXJNXXNJAH-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910021481 rutherfordium Inorganic materials 0.000 description 1
- YGPLJIIQQIDVFJ-UHFFFAOYSA-N rutherfordium atom Chemical compound [Rf] YGPLJIIQQIDVFJ-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 125000002211 silanetriyl group Chemical group [H][Si](*)(*)* 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 238000004383 yellowing Methods 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
- 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
- C09D183/14—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 at least two but not all the silicon atoms are connected by linkages other than oxygen 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/58—Metal-containing linkages
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Definitions
- the present invention relates to a composition suitable for use as an encapsulating material for an optoelectronic device and a method of producing the same.
- Light-emitting diode can be used as a back-light source of a display, as a portable light source or as street light.
- light extraction efficiency is one major concern of an LED.
- Light extraction efficiency is reduced because light is not fully released from a light-emitting chip of the device. Such problem arise due to a difference in refractive index between a light-emitting chip in the device and its environment. This could cause part of the light produced from the chip being trapped there within, instead of fully being emitted therefrom.
- thermosetting epoxy resins and silicone-based materials are generally used as the encapsulating material for an LED.
- thermosetting epoxy resins Despite excellent optical transparency in the visible range and low gas permeability, thermosetting epoxy resins generally have low refractive index and they cannot maintain their transparency at operating temperature of an LED, thereby resulting in heat-induced yellowing.
- US 7985476 B2 disclosed a composition for sealing a light emitting element comprising a zirconia particle-containing resin, in which zirconia particle is used as high refractive index filler being dispersed in a matrix of silicone, epoxy or acrylic resin. Nevertheless, the zirconia particles were limited to tetragonal zirconia particles with a particle diameter of 20 nm or less to reduce the extent of light scattering and maintaining transparency of the composition.
- this invention provides a composition having an alkoxide of element from Group 4, 5 or 16 and an ethylenically unsaturated monomer comprising an isobornyl group or an organosilane being chemically bonded to a phenyl silicone resin system.
- Such material has a refractive index ranging from 1.59 to 1.65 and it works as an excellent encapsulating material for an LED.
- One object of this invention is to provide a composition which can be made into an LED encapsulation material, in which the material could achieve an optical transparency of more than 95% at wavelength between300 to 800nm with a thickness between 1 mm, but not limited thereto.
- Another object of this invention is to provide a composition which is stable and capable of withstanding heat from a soldering treatment, usually conducted at approximately 260 °C for at least 1 minute, but not limited thereto.
- the composition further comprises an ethylenically unsaturated monomer comprising an isobornyl group.
- the ethylenically unsaturated monomer comprising an isobornyl group is isobornyl methacrylate or acrylate or a mixture thereof.
- the reaction product can be made in the absence or presence of a solvent.
- a solvent is selected from methanol, ethanol, propanol, butanol, ethyl acetate, acetone, isopropyl alcohol, dichloromethane, chloroform, dimethylformamide, dimethyl sulfoxide and/or acetone nitride.
- the organoalkoxysilane compound having a formula (R 2 ) m - Si-(OR 3 )n, wherein m and n are positive integers 0 to 4, R 2 and R 3 are independently selected from a group consisting of Ci to C3 alkyl, C 2 to C3 alkenyl, C5 to C 8 cycloalkyl, C 6 aryl, C 6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
- the organoalkoxysilane is selected from any one or a mixture of two or more of tetracyclopentylorthosilicate, tetracyclohexylorthosilicate, tetracycloheptylorthosilicate, tetracyclooctylorthosilicate, cyclopentyltris(cyclopentyloxy)silane, cyclohexyltris(cyclohexyloxy)silane, cycloheptyltris(cycloheptyloxy)silane, cyclooctyltris(cyclooctyloxy)silane, dicyclopentylbis(cyclopentyloxy)silane, dicyclohexylbis(cyclohexyloxy)silane, dicycloheptylbis(cycloheptyloxy)silane, dicyclooctylbis(cyclooctyloxy)
- the compound having formula M-COR 1 ⁇ is selected from any one or a mixture of two or more of tetramethoxytitanium, tetraethoxytitanium, tetrapropoxytitanium, tetrabutoxytitanium, tetrabutoxyhafnium, tetrapropoxyhafnium, tetraefhoxyhafnium, tetramethoxyhafnium, tetramethoxyrutherfordium,
- the catalyst is hydrochloric acid, sulfuric acid, trifilic acid, nitric acid, phosphoric acid, ethanoic acid, potassium hydroxide, sodium hydroxide or barium hydroxide.
- the compound having formula M-COR 1 ⁇ is present in an amount of 10 to 70 mole % of the composition.
- the ethylenically unsaturated monomer comprising an isobornyl group is present in an amount of 10 to 50 mole % of the composition.
- the organosilane is present in an amount of 10 to 50 mole % of the composition.
- the organoalkoxysilane compound is present in an amount of 10 to 80 mole % of the composition.
- the method further comprising a step of reacting an ethylenically unsaturated compound comprising an isobornyl group with the hydrolysed organoalkoxysilane compound.
- the organoalkoxysilane compound has a formula (R 2 ) m -Si-(OR 3 ) n , wherein m and n are positive integers 0 to 4, R 2 and R 3 are independently selected from a group consisting of Ci to C 3 alkyl, C 2 to C 3 alkenyl, C 5 to C 8 cycloalkyl, C 6 aryl, C 6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
- the composition has a refractive index of 1.59 to 1.65 at 589 nm.
- Fig. 1 is a diagram of an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an isobornyl group without using a catalyst.
- Fig. 2 is a diagram of an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an isobornyl group in the presence of a catalyst.
- Fig. 3 is a diagram for an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an organosilane in the presence of a catalyst.
- a sol-gel process is adapted to produce the organosiloxane composition as described hereinafter. Hydrolysis kinetics of a sol is manipulated to obtain a desired gel structure. Relevant variables in manipulating the kinetics are, but not limited to, concentration of reactant used, reaction medium used, concentration of catalyst used and reaction temperature.
- Fig.3 Molecular structure of an exemplified reaction product derived from the method is shown in Fig.3.
- the method further comprises a step of reacting an ethylenically unsaturated monomer comprising an isobornyl group with the hydrolysed organoalkoxysilane.
- a step of reacting an ethylenically unsaturated monomer comprising an isobornyl group with the hydrolysed organoalkoxysilane is shown in Fig.1 and 2.
- the method can be conducted in the absence of solvent.
- solvent can be used to adjust viscosity of the mixture. It is preferred that the solvent is inert to the compounds in the present invention.
- the preferred solvent can be selected from methanol, ethanol, propanol, butanol, ethyl acetate, acetone, isopropyl alcohol, dichloromethane, chloroform, dimethylformamide, dimethyl sulfoxide and/or acetone nitride.
- the step of hydrolysing is preferably conducted in the presence of a catalyst.
- a catalyst can be an acid catalyst selected from hydrochloric acid, sulfuric acid, trifilic acid, nitric acid, phosphoric acid and/or ethanoic acid.
- hydrochloric acid is most preferred.
- An exemplary structure of the composition made in the presence of hydrochloric acid is shown in Fig. 2.
- the step of hydrolysing can be conducted using basic catalyst selected from potassium hydroxide, sodium hydroxide and/or barium hydroxide.
- the basic catalyst barium hydroxide is most preferred. Structure of the composition made in the presence of basic catalyst is not shown. Nevertheless, it shall be noted that hydrolysation using acid or basic catalyst give rise to a similar hydrolysed structure. In the event where basic catalyst is used, the rate of hydrolysation is relatively slower due to possible reversible reaction under a basic condition. Only a small amount of catalyst is required for the hydrolysing step. In the preferred embodiment, 0.01-10 mole % of hydrochloric acid is used to hydrolyse the organoalkoxysilane.
- the organoalkoxysilane compound has a formula (R 2 ) m -Si-(OR 3 ) n , wherein m and n are positive integers 0 to 4, R 2 and R 3 are independently selected from a group consisting of d to C 3 alkyl, C 2 to C 3 alkenyl, C 5 to C 8 cycloalkyl, Ce aryl, C 6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
- the organoalkoxysilane compound can be selected from any one or a mixture of two or more of tetracyclopentylorthosilicate, tetracyclohexylorthosilicate, tetracycloheptylorthosilicate, tetracyclooctylorthosilicate, cyclopentyltris(cyclopentyloxy)silane, cyclohexyltris(cyclohexyloxy si] ane, cycloheptyltris(cycloheptyloxy)silane, cyclooctyltris(cyclooctyloxy si] ane, dicyclopentylbis(cyclopentyloxy)silane, dicyclohexylbis(cyclohexyloxy si ane, dicycloheptylbis(cycloheptyloxy)silane, dicyclooctylbis(cyclooctyloxy
- the organosilane can be any one or a mixture of two of more of methoxydimethyl(vinyl)silane, ethoxydiethyl(vinyl)silane, vinylsilanol, trimethoxy(vinyl)silane, triethoxy(vinyl)silane, phenoxydiphenyl(vinyl)silane, dicyclopentyl(cyclopentyloxy)(vinyl)silane, dicyclohexyl(cyclohexyloxy)(vinyl)silane, dicyclopentyl(methoxy)(vinyl)silane, dicyclohexyl(methoxy)(vinyl)silane, methoxydiphenyl(vinyl)silane, ethoxydiphenyl(vinyl)silane and diphenyl(propoxy)(vinyl)silane.
- triethoxy(vinyl)silane is preferably used.
- the organoalkoxysilane is present in an amount of 10 to 70 mole % and the organosilane is present in an amount of 10 to 50 mole % of the composition.
- the composition is rendered being photo-curable and thermally stable by adding an ethylenically unsaturated monomer comprising an isobornyl group. More particularly, the ethylenically unsaturated monomer comprising an isobornyl group is isobornyl methacrylate or acrylate or a mixture thereof. More preferably, isobornyl acrylate ( ⁇ 30 ⁇ ) is used in an amount of 10 to 50 mole % in the composition.
- the composition is rendered having an improved refractive index (RI) by adding a compound having formula in a dropwise manner, to the organoalkoxysilane compound.
- a compound having formula x is an integer 4 to 6
- M is an element selected from Group 4, 5 or 16
- R 1 is selected from Ci to C 4 alkyl, C 5 to C 8 cycloalkyl, C 6 aryl, C6 heterocycloalkyl containing element N
- S or O can be selected from any one or a mixture of two or more of tetramethoxytitanium, tetraethoxytitanium, tetrapropoxytitanium, tetrabutoxytitanium, tetrabutoxyhafnium, tetrapropoxyhafnium, tetraethoxyhafnium, tetramethoxyhafnium, tetramethoxyrutherfordium, tetraethoxyrutherfordium, tetraeth
- tetraethoxyselenium tetrapropoxyselenium, tetrabutoxyselenium, tetramethoxytellurium, tetraethoxytellurium, tetrapropoxytellurium, tetrabutoxytellurium, tetramethoxypolonium, tetraethoxypolonium, tetrapropoxypolonium, tetrabutoxypolonium, pentakis(cyclopentyloxy)hafnium, pentaphenoxyhafnium, butoxytetrapropoxyhafnium, pentapropoxyhafnium, hexapropoxyniobium, hexaphenoxyniobium, hexakis(cyclopentyloxy)niobium, niobium n-propoxide pentakis(cyclopentyloxy)selenium, pentaphenoxyselenium, butoxytetrapropoxyselen
- elements from period 4 to 7 are preferred due to the presence of vacant orbitals which can be involved in formation of coordination bond.
- tetraethoxyselenium can be used in an amount of 10 to 70 mole % in the composition.
- the compound having formula the present invention can be provided in solid or fluid form. In the case where solid form is provided, it is preferably added to the same solvent as it might be used during the previous step, such that the compound having formula can be added into the organoalkoxysilane compound in a dropwise manner.
- a resinous composition can be obtained and it is preferably filtered and vacuum heated to remove any volatile components therein.
- the step of hydrolysing the organoalkoxysilane, reacting it with the ethylenically unsaturated monomer and the compound having formula conducted in an inert condition at a temperature of 0 to 200 °C under a pressure of 0 to 5 atm. Temperature exceeding 200 °C may cause decomposition and melting of the reaction product.
- EXAMPLE 2 22.3 g of diphenyldimethylsilane (DOS) having a molecular weight of 383.68 g/mol was mixed with 2.5 g of hydrochloric acid (HCl) and 12 g of ethanol. The mixture was left to react for 15 minutes. Subsequently, 4.16 g of isobornyl acrylate ( ⁇ ) having a molecular weight of 208.3 g mol was added therein and left to react for another 1 hour. Then, 7.67 g of zirconium propoxide (ZPO) having a molecular weight of 383.68 g/mol was added therein and left to react for another 1 hour. Thereinafter, the mixture was subject to neutralisation using sodium carbonate, followed by filtration to remove unreacted zirconium particles. The filtrate appeared clear. Further, the filtrate has refractive index (RI) of approximately 1.59-1.65 at 589nm.
- RI refractive index
- DDS diphenyldimethylsilane
- HCl hydrochloric acid
- ethanol aqueous ethanol
- ZPO zirconium propoxide
- the mixture was subjected to neutralisation using sodium carbonate, followed by filtration to remove unreacted zirconium particles.
- the filtrate appeared clear. Further, the filtrate has a refractive index (RI) of approximately 1.59-1.65 at 589 nm.
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Abstract
This invention relates to a composition suitable for use as an encapsulating material for an optoelectronic device and a method of producing the same. More particularly, the organosiloxane composition for use as an encapsulating material for a light emitting element comprising a reaction product of: (a) a compound having formula M-(OR1)x, where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from C1 to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O; (b) an organoalkoxysilane compound; and (c) an organosilane having formula (R4)-0-Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of C1 to C3 alkyl, C1 to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl in the presence of a catalyst.
Description
ORGANOSILOXANE HYBRID COMPOSITION FOR ENCAPSULATION OF
LIGHT-EMITTING ELEMENTS
FIELD OF TECHNOLOGY
The present invention relates to a composition suitable for use as an encapsulating material for an optoelectronic device and a method of producing the same.
BACKGROUND OF THE INVENTION
Light-emitting diode (LED) can be used as a back-light source of a display, as a portable light source or as street light. However, light extraction efficiency is one major concern of an LED. Light extraction efficiency is reduced because light is not fully released from a light-emitting chip of the device. Such problem arise due to a difference in refractive index between a light-emitting chip in the device and its environment. This could cause part of the light produced from the chip being trapped there within, instead of fully being emitted therefrom.
Use of light encapsulating material is one of the possible solutions to the abovementioned problem. Thermosetting epoxy resins and silicone-based materials are generally used as the encapsulating material for an LED. Despite excellent optical transparency in the visible range and low gas permeability, thermosetting epoxy resins generally have low refractive index and they cannot maintain their transparency at operating temperature of an LED, thereby resulting in heat-induced yellowing.
In view of the above, attempts are made to increase refractive index of a thermosetting epoxy composite resin. One of the example of such attempts can be exemplified by United States Patent No. US 7985476 B2. Particularly, US 7985476 B2 disclosed a composition
for sealing a light emitting element comprising a zirconia particle-containing resin, in which zirconia particle is used as high refractive index filler being dispersed in a matrix of silicone, epoxy or acrylic resin. Nevertheless, the zirconia particles were limited to tetragonal zirconia particles with a particle diameter of 20 nm or less to reduce the extent of light scattering and maintaining transparency of the composition.
Alternatively, this invention provides a composition having an alkoxide of element from Group 4, 5 or 16 and an ethylenically unsaturated monomer comprising an isobornyl group or an organosilane being chemically bonded to a phenyl silicone resin system. Such material has a refractive index ranging from 1.59 to 1.65 and it works as an excellent encapsulating material for an LED.
SUMMARY OF THE INVENTION One object of this invention is to provide a composition which can be made into an LED encapsulation material, in which the material could achieve an optical transparency of more than 95% at wavelength between300 to 800nm with a thickness between 1 mm, but not limited thereto. Another object of this invention is to provide a composition which is stable and capable of withstanding heat from a soldering treatment, usually conducted at approximately 260 °C for at least 1 minute, but not limited thereto.
At least one of the preceding objects is met, in whole or in part, by the present invention, in which one of the embodiments of the present invention is an organosiloxane composition for use as an encapsulating material for a light emitting element comprising a reaction product of: (a) a compound having formula
where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from Ci to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or 0;(b) an
organoalkoxysilane compound; and (c) an organosilane having formula (R4)-0- Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of Ci to C3 alkyl, Ci to C3 alkoxy, hydrogen, C6 aryl and or C5 to C8 cycloalkyl in the presence of a catalyst.
Preferably, the composition further comprises an ethylenically unsaturated monomer comprising an isobornyl group.
In the preferred embodiment, the ethylenically unsaturated monomer comprising an isobornyl group is isobornyl methacrylate or acrylate or a mixture thereof.
The reaction product can be made in the absence or presence of a solvent. In the case where a solvent is present, the solvent is selected from methanol, ethanol, propanol, butanol, ethyl acetate, acetone, isopropyl alcohol, dichloromethane, chloroform, dimethylformamide, dimethyl sulfoxide and/or acetone nitride.
In the preferred embodiment, the organoalkoxysilane compound having a formula (R2)m- Si-(OR3)n, wherein m and n are positive integers 0 to 4, R2 and R3 are independently selected from a group consisting of Ci to C3 alkyl, C2 to C3 alkenyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
In the preferred embodiment, the organoalkoxysilane is selected from any one or a mixture of two or more of tetracyclopentylorthosilicate, tetracyclohexylorthosilicate, tetracycloheptylorthosilicate, tetracyclooctylorthosilicate, cyclopentyltris(cyclopentyloxy)silane, cyclohexyltris(cyclohexyloxy)silane, cycloheptyltris(cycloheptyloxy)silane, cyclooctyltris(cyclooctyloxy)silane, dicyclopentylbis(cyclopentyloxy)silane, dicyclohexylbis(cyclohexyloxy)silane, dicycloheptylbis(cycloheptyloxy)silane, dicyclooctylbis(cyclooctyloxy)silane,
tricyclopentyl(cyclopentyloxy)silane, tricyclohexyl(cyclohexyloxy)silane, tricycloheptyl(cycloheptyloxy)silane, tricyclooctyl(cyclooctyloxy)silane, tris(cycloheptyloxy)(cyclopentyl)silane, tris(cyclooctyloxy)(cyclopentyl)silane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxy)(cyclohexyl)silane, cyclohexyltris(cyclooctyloxy)silane, cycloheptyltris(cyclopentyloxy)silane, cycloheptyltris(cyclohexyloxy)silane, cycloheptyltris(cyclooctyloxy)silane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxy)(cyclohexyl)silane, cyclohexyltris(cyclooctyloxy)silane, cyclooctyltris(cyclopentyloxy)silane, tris(cyclohexyloxy)(cyclooctyl)silane, tris(cycloheptyloxy)(cyclooctyl)silane, bis(cyclohexyloxy)dicyclopentylsilane, bis(cycloheptyloxy)dicyclopentylsilane, bis(cyclooctyloxy)dicyclopentylsilane, dicyclohexylbis(cyclopentyloxy)silane, bis(cycloheptyloxy)dicyclohexylsilane, dicyclohexylbis(cyclooctyloxy)silane, dicycloheptylbis(cyclopentyloxy)silane, dicycloheptylbis(cyclohexyloxy)silane, dicycloheptylbis(cyclooctyloxy)silane, dicyclooctylbis(cyclopentyloxy)silane, bis(cyclohexyloxy)dicyclooctylsilane, bis(cycloheptyloxy)dicyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cycloheptyloxytricyclopentylsilane, cycloheptyloxytricyclohexylsilane, cycloheptyloxytricyclooctylsilane, cyclooctyloxytxicyclopentylsilane, tricyclohexyl(cyclooctyloxy)silane, tricycloheptyl(cyclooctyloxy)silane, tetrapyridin-4-yl orthosilicate, tetra(2H-pyran-4-yl) orthosilicate, tetra(2H-thiopyran-4-yl) orthosilicate, 4,4',4"-(pyridin-4-ylsilanetriyl)tris(oxy)tripyridine, tris(2H-pyran-4-yloxy)(2H-pyran-4- yl)silane, tris(2H-thiopyran-4-yloxy)(2H-thiopyran-4-yl)silane, 4-(tris(2H-pyran-4- yloxy)silyl)pyridine, 4-(tris(2H-thiopyran-4-yloxy)silyl)pyridine, 4,4',4"-((2H-pyran-4- yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H-pyran-4-yl)silane, 4,4\4''-((2H-pyran-4-yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H- pyran-4-yl)silane, dipyridin-4-ylbis(pyridin-4-yloxy)silane, bis(2H-pyran-4-yloxy)di(2H- pyran-4-yl)silane, bis(2H-thiopyran-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran-
4-yloxy)dipyridin-4-ylsilane, bis(2H-thiopyran-4-yloxy)dipyridin-4-ylsilane, di(2H- pyran-4-yl)bis(pyridin-4-yloxy)silane, bis(2H-thiopyran-4-yloxy)di(2H-pyran-4-yl)silane, bis(pyridin-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran-4-yloxy)di(2H-thiopyran- 4-yl)silane, 4,4',4"-((pyridin-4-yloxy)silanetriyl)tripyridine, (2H-pyran-4-yloxy)tri(2H- pyran-4-yl)silane, (2H-thiopyran-4-yloxy)tri(2H-thiopyran-4-yl)silane, 4,4'-((2H-pyran-4- yloxy)(2H-pyran-4-yl)silanediyl)dipyridine, 4,4'-((2H-thiopyran-4-yloxy)(2H-thiopyran- 4-yl)silanediyl)dipyridine, 4-(di(2H-pyran-4-yl)(pyridin-4-yl)silyloxy)pyridine, (2H- thiopyran-4-yloxy)di(2H-pyran-4-yl)(2H-thiopyran-4-yl)silane, 4-(pyridin-4-yldi(2H- thiopyran-4-yl)silyloxy)pyridine, (2H-pyran-4-yloxy)(2H-pyran-4-yl)di(2H-thiopyran-4- yl)silane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane,ethyltrimethoxysilane, ethyltriethoxysilane, ethyltripopoxysilane, propyltrimethoxysilane,
propyltriethoxysilane, propyltripropoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, phenyltrimethoxysilane, 3-acryloxypropyl trimethoxysilane, 3- acryloxypropyl triethoxysilane, 3-acryloxypropyl tripropoxysilane, methoxydimethylvinylsilane, ethoxydimethylvinylsilane, propoxydimethylvinylsilane, methoxydiethylvinylsilane, ethoxydiethylvinylsilane, propoxydiethylvinylsilane, methoxydipropylvinylsilane, ethoxydipropylvinylsilane, propoxydipropylvinylsilane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldipropoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldipropoxysilane, dipropyldimethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane and diphenyldipropoxysilane.
In the preferred embodiment, the compound having formula M-COR1^ is selected from any one or a mixture of two or more of tetramethoxytitanium, tetraethoxytitanium, tetrapropoxytitanium, tetrabutoxytitanium, tetrabutoxyhafnium, tetrapropoxyhafnium, tetraefhoxyhafnium, tetramethoxyhafnium, tetramethoxyrutherfordium,
tetraethoxyrutherfordium, tetrapropoxyrutherfordium, tetrabutoxyrutherfordium, tetrabutoxyvanadium, tetrapropoxyvanadium, tetraethoxyvanadium,
tetramethoxyvanadium, tetramethoxyniobium, tetraethoxyniobium, tetrapropoxyniobium, tetrabutoxyniobium, tetrabutoxytantalum, tetrapropoxytantalum, tetraethoxytantalum, tetramethoxytantalum, tetramethoxydubnium, tetraethoxydubnium,
tetrapropoxydubnium, tetrabutoxydubnium,tetraphenoxytitanium,
tetraphenoxyzirconium, tetraphenoxyhafnium, tetraphenoxyrutherfordium,
tetraphenoxyvanadium, tetraphenoxyniobium, tetraphenoxytantalum,
tetraphenoxydubnium, tetrakis(cyclopentyloxy)titanium,
tetrakis(cyclopentyloxy)zirconium, tetrakis(cyclopentyloxy)hafhium,
tetrakis(cyclopentyloxy)rutherfordium, tetrakis(cyclopentyloxy)vanadium,
tetrakis(cyclopentyloxy)niobium, tetrakis(cyclopentyloxy)tantalum,
tetrakis(cyclopentyloxy)dubnium, tetrakis(cyclohexyloxy)titanium,
tetrakis(cyclohexyloxy)zirconium, tetrakis(cyclohexyloxy)hafhium,
tetrakis(cyclohexyloxy)rutherfordium, tetrakis(cyclohexyloxy)vanadium,
tetrakis(cyclohexyloxy)niobium, tetrakis(cyclohexyloxy)tantalum,
tetrakis(cyclohexyloxy)dubnium, tetrakis(cycloheptyloxy)titanium,
tetrakis(cycloheptyloxy)zirconium, tetrakis(cycloheptyloxy)hafhium,
tetrakis(cycloheptyloxy)vanadium, tetrakis(cycloheptyloxy)niobium,
tetrakis(cycloheptyloxy)tantalum, tetrakis(cycloheptyloxy)dubnium,
tetrakis(cyclooctyloxy)titanium, tetrakis(cyclooctyloxy)zirconium,
tetrakis(cyclooctyloxy)hafhium, tetrakis(cyclooctyloxy)rutherfordium,
tetrakis(cyclooctyloxy)vanadium, tetrakis(cyclooctyloxy)niobium, niobium n-propoxide ,tetraMs(cyclooctyloxy)tantalum,tetralds(cyclooctyloxy)dubnium,tetramethoxyselenium, tetraethoxyselenium, tetrapropoxyselenium, tetrabutoxyselenium, tetramethoxytellurium, tetraethoxytellurium, tetrapropoxytellurium, tetrabutoxytellurium, tetramethoxypolonium, tetraethoxypolonium, tetrapropoxypolonium, tetrabutoxypolonium, pentakis(cyclopentyloxy)hafnium, pentaphenoxyhafnium, butoxytetrapropoxyhafhium, pentapropoxyhafnium, hexapropoxyniobium, hexaphenoxyniobium, hexakis(cyclopentyloxy)niobium, selenium hexa-iso-propoxide pentakis(cyclopentyloxy)selenium, pentaphenoxyselenium, butoxytetrapropoxyselenium,
pentapropoxyselenium, hexapropoxyselenium, hexaphenoxyselenium, hexakis(cyclopentyloxy)selenium, tetrapropoxyzirconium, zirconium ethoxide, zirconium propoxide, zirconium isopropoxide, zirconium butoxide, and zirconium t-butoxide.
In the preferred embodiment, the organosilane having formula (R4)-0-Si(C=C)(R5)2 is any one or a mixture of two of more of methoxydimethyl(vinyl)silane, ethoxydiethyl(vinyl)silane, vinylsilanol, trimethoxy(vinyl)silane, triethoxy(vinyl)silane, phenoxydiphenyl(vinyl)silane, dicyclopentyl(cyclopentyloxy)(vinyl)silane, dicyclohexyl(cyclohexyloxy)(vinyl)silane, dicyclopentyl(methoxy)(vinyl)silane, dicyclohexyl(methoxy)(vinyl)silane, methoxydiphenyl(vinyl)silane, ethoxydiphenyl(vinyl)silane and diphenyl(propoxy)(vinyl)silane.
Preferably, the catalyst is hydrochloric acid, sulfuric acid, trifilic acid, nitric acid, phosphoric acid, ethanoic acid, potassium hydroxide, sodium hydroxide or barium hydroxide.
Preferably, the compound having formula M-COR1^ is present in an amount of 10 to 70 mole % of the composition.
Preferably, the ethylenically unsaturated monomer comprising an isobornyl group is present in an amount of 10 to 50 mole % of the composition.
Preferably, the organosilane is present in an amount of 10 to 50 mole % of the composition.
Preferably, the organoalkoxysilane compound is present in an amount of 10 to 80 mole % of the composition.
At least one of the preceding objects is met, in whole or in part, by the present invention, in which one of the embodiments of the present invention is a method of producing the organosiloxane composition, comprising steps of:(a) hydrolysing an organoalkoxysilane compound in a pH environment of 1 to 12; (b) reacting an organosilane having formula (R4)-0-Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of Ci to C3 alkyl, Ci to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl with the hydrolysed organoalkoxysilane compound; and (c) adding a compound having formula M- where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from O to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O into the reacted organoalkoxysilane compound , in which the hydrolysing, reacting and adding steps are conducted in an inert condition at a temperature of 0 to 200 °C under a pressure of 0 to 5 atm.
Preferably, the method further comprising a step of reacting an ethylenically unsaturated compound comprising an isobornyl group with the hydrolysed organoalkoxysilane compound.
Preferably, the organoalkoxysilane compound has a formula (R2)m-Si-(OR3)n, wherein m and n are positive integers 0 to 4, R2 and R3 are independently selected from a group consisting of Ci to C3 alkyl, C2 to C3 alkenyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
In accordance to the preceding description, the composition has a refractive index of 1.59 to 1.65 at 589 nm.
BRIEF DESCRIPTION OF THE DRAWINGS
For the purpose of facilitating an understanding of the invention, there is illustrated in the accompanying drawing the preferred embodiments from an inspection of which when considered in connection with the following description, the invention, its construction and operation and many of its advantages would be readily understood and appreciated.
Fig. 1 is a diagram of an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an isobornyl group without using a catalyst.
Fig. 2 is a diagram of an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an isobornyl group in the presence of a catalyst.
Fig. 3 is a diagram for an exemplary embodiment of this invention made in the presence of an ethylenically unsaturated monomer comprising an organosilane in the presence of a catalyst.
BRIEF DESCRIPTION OF THE INVENTION
Exemplary, non-limiting embodiments of the present invention is described in detail with references to Figs. 1 to 3. However, it is to be understood that limiting the description to the preferred embodiments of the invention is merely to facilitate discussion of the present invention and it is envisioned that those skilled in the art may devise various modifications without departing from the scope of the appended claim. A sol-gel process is adapted to produce the organosiloxane composition as described hereinafter. Hydrolysis kinetics of a sol is manipulated to obtain a desired gel structure. Relevant variables in manipulating the kinetics are, but not limited to, concentration of reactant used, reaction medium used, concentration of catalyst used and reaction temperature.
The method comprising steps of: acid or base-catalysed hydrolysing an organoalkoxysilane; reacting an organosilane having a formula (R4)-0-Si(C=C)(R5)2, where R4 and R5 are independently selected from a group consisting of Ci to C3 alkyl, Ci to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl group with the hydrolysed organoalkoxysilane; and adding a compound having formula M-fOR1)* into the reacted mixture, where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, where R1 is selected from Ci to C alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O. Molecular structure of an exemplified reaction product derived from the method is shown in Fig.3.
In another preferred embodiment, the method further comprises a step of reacting an ethylenically unsaturated monomer comprising an isobornyl group with the hydrolysed organoalkoxysilane. Molecular structure of an exemplified reaction products derived from the method is shown in Fig.1 and 2.
The method can be conducted in the absence of solvent. If necessary, solvent can be used to adjust viscosity of the mixture. It is preferred that the solvent is inert to the compounds in the present invention. The preferred solvent can be selected from methanol, ethanol, propanol, butanol, ethyl acetate, acetone, isopropyl alcohol, dichloromethane, chloroform, dimethylformamide, dimethyl sulfoxide and/or acetone nitride.
In accordance to the preceding description, the step of hydrolysing is preferably conducted in the presence of a catalyst. An exemplary structure of the composition made in the absence of catalyst is shown in Fig. 1 as a comparison. The catalyst can be an acid catalyst selected from hydrochloric acid, sulfuric acid, trifilic acid, nitric acid, phosphoric acid and/or ethanoic acid. Amongst the acid catalyst, hydrochloric acid is most preferred. An exemplary structure of the composition made in the presence of hydrochloric acid is shown in Fig. 2. On the other hand, the step of hydrolysing can be conducted using basic catalyst
selected from potassium hydroxide, sodium hydroxide and/or barium hydroxide. Amongst the basic catalyst, barium hydroxide is most preferred. Structure of the composition made in the presence of basic catalyst is not shown. Nevertheless, it shall be noted that hydrolysation using acid or basic catalyst give rise to a similar hydrolysed structure. In the event where basic catalyst is used, the rate of hydrolysation is relatively slower due to possible reversible reaction under a basic condition. Only a small amount of catalyst is required for the hydrolysing step. In the preferred embodiment, 0.01-10 mole % of hydrochloric acid is used to hydrolyse the organoalkoxysilane.
The organoalkoxysilane compound has a formula (R2)m-Si-(OR3)n, wherein m and n are positive integers 0 to 4, R2 and R3 are independently selected from a group consisting of d to C3 alkyl, C2 to C3 alkenyl, C5 to C8 cycloalkyl, Ce aryl, C6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group. Preferably, the organoalkoxysilane compound can be selected from any one or a mixture of two or more of tetracyclopentylorthosilicate, tetracyclohexylorthosilicate, tetracycloheptylorthosilicate, tetracyclooctylorthosilicate, cyclopentyltris(cyclopentyloxy)silane, cyclohexyltris(cyclohexyloxy si] ane, cycloheptyltris(cycloheptyloxy)silane, cyclooctyltris(cyclooctyloxy si] ane, dicyclopentylbis(cyclopentyloxy)silane, dicyclohexylbis(cyclohexyloxy si ane, dicycloheptylbis(cycloheptyloxy)silane, dicyclooctylbis(cyclooctyloxy) si ane, tricyclopentyl(cyclopentyloxy)silane, tricyclohexyl(cyclohexylox si] ane, tricycloheptyl(cycloheptyloxy)silane, tricyclooctyl(cyclooctylox si ane, tris(cycloheptyloxy)(cyclopentyl)silane, tris(cyclooctyloxy)(cyclopentyl si ane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxyXcyclohexyl) si ane, cyclohexyltris(cyclooctyloxy)silane, cycloheptyltris(cyclopentyloxy) si ane, cycloheptyltris(cyclohexyloxy)silane, cycloheptyltris(cyclooctyloxy si ane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxy) (cyclohexyl] si ane, cyclohexyltris(cyclooctyloxy)silane, cyclooctyltris(cyclopentyloxy si ane, tris(cyclohexyloxy)(cyclooctyl)silane, tris(cycloheptyloxy)(cyclooctylj si ane,
bis(cyclohexyloxy)dicyclopentylsilane, bis(cycloheptyloxy)dicyclopentylsilane, bis(cyclooctyloxy)dicyclopentylsilane, dicyclohexylbis(cyclopentyloxy)silane, bis(cycloheptyloxy)dicyclohexylsilane, dicyclohexylbis(cyclooctyloxy)silane, dicycloheptylbis(cyclopentyloxy)silane, dicycloheptylbis(cyclohexyloxy)silane, dicycloheptylbis(cyclooctyloxy)silane, dicyclooctylbis(cyclopentyloxy)silane, bis(cyclohexyloxy)dicyclooctylsilane, bis(cycloheptyloxy)dicyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cycloheptyloxytricyclopentylsilane, cycloheptyloxytricyclohexylsilane, cycloheptyloxytricyclooctylsilane, cyclooctyloxytricyclopentylsilane, tricyclohexyl(cyclooctyloxy)silane, tricycloheptyl(cyclooctyloxy)silane, tetrapyridin-4-yl orthosilicate, tetra(2H-pyran-4-yl) orthosilicate, tetra(2H-thiopyran-4-yl) orthosilicate, 4,4 4''-(pyridin-4-ylsilanetriyl)ttis(oxy)tripyridine, tris(2H-pyran-4-yloxy)(2H-pyran-4- yl)silane, tris(2H-thiopyran-4-yloxy)(2H-thiopyran-4-yl)silane, 4-(tris(2H-pyran-4- yloxy)silyl)pyridine, 4-(ttis(2H-thiopyran-4-yloxy)silyl)pyridine, 4,4',4"-((2H-pyran-4- yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H-pyran-4-yl)silane, 4,4 4,'-((2H^yran-4-yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H- pyran-4-yl)silane, dipyridin-4-ylbis(pyridin-4-yloxy)silane, bis(2H-pyran-4-yloxy)di(2H- pyran-4-yl)silane, bis(2H-t dopyran-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran- 4-yloxy)dipyridin-4-ylsilane, bis(2H-thiopyran-4-yloxy)dipyridin-4-ylsilane, di(2H- pyran-4-yl)bis(pyridin-4-yloxy)silane, bis(2H-thiopyran-4-yloxy)di(2H-pyran-4-yl)silane, bis(pyridin-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran-4-yloxy)di(2H-thiopyran- 4-yl)silane, 4,4',4"-((pyridin-4-yloxy)silanetriyl)tripyridine, (2H-pyran-4-yloxy)tri(2H- pyran-4-yl)silane, (2H-thiopyran-4-yloxy)tri(2H-thiopyran-4-yl)silane, 4,4'-((2H-pyran-4- yloxy)(2H-pyran-4-yl)silanediyl)dipyridine, 4,4'-((2H-thiopyran-4-yloxy)(2H-thiopyran- 4-yl)silanediyl)dipyridine, 4-(di(2H-pyran-4-yl)(pyridin-4-yl)silyloxy)pyridine, (2H- thiopyran-4-yloxy)di(2H-pyran-4-yl)(2H-thiopyran-4-yl)silane, 4-(pyridin-4-yldi(2H- thiopyran-4-yl)silyloxy)pyridine, (2H-pyran-4-yloxy)(2H-pyran-4-yl)di(2H-thiopyran-4-
yl)silane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane,ethyltrimethoxysilane, ethyltriethoxysilane, ethyltripopoxysilane, propyltrimethoxysilane,
propyltnethoxysilane, propyltripropoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, phenyltrimethoxysilane, 3-acryloxypropyl trimethoxysilane, 3- acryloxypropyl triethoxysilane, 3-acryloxypropyl tripropoxysilane, methoxydimethylvinylsilane, ethoxydimethylvinylsilane, propoxydimethylvinylsilane, methoxydiethylvinylsilane, ethoxydiethylvinylsilane, propoxydiethylvinylsilane, methoxydipropylvinylsilane, ethoxydipropylvinylsilane, propoxydipropylvinylsilane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldipropoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldipropoxysilane, dipropyldimethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane and diphenyldipropoxysilane. In the preferred embodiment, the organoalkoxysilane compound is present in an amount of 10 to 80 mole % of the composition.
With reference to Fig. 3, the composition is rendered more viscous and with improved clarity by adding an organosilane having formula (R4)-0-Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of Ci to C3 alkyl, Ci to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl. The organosilane can be any one or a mixture of two of more of methoxydimethyl(vinyl)silane, ethoxydiethyl(vinyl)silane, vinylsilanol, trimethoxy(vinyl)silane, triethoxy(vinyl)silane, phenoxydiphenyl(vinyl)silane, dicyclopentyl(cyclopentyloxy)(vinyl)silane, dicyclohexyl(cyclohexyloxy)(vinyl)silane, dicyclopentyl(methoxy)(vinyl)silane, dicyclohexyl(methoxy)(vinyl)silane, methoxydiphenyl(vinyl)silane, ethoxydiphenyl(vinyl)silane and diphenyl(propoxy)(vinyl)silane. Amongst the foregoing, triethoxy(vinyl)silane is preferably used. In the preferred embodiment, the organoalkoxysilane is present in an amount of 10 to 70 mole % and the organosilane is present in an amount of 10 to 50 mole % of the composition.
Γη the present invention, the composition is rendered being photo-curable and thermally stable by adding an ethylenically unsaturated monomer comprising an isobornyl group. More particularly, the ethylenically unsaturated monomer comprising an isobornyl group is isobornyl methacrylate or acrylate or a mixture thereof. More preferably, isobornyl acrylate (Π30Α) is used in an amount of 10 to 50 mole % in the composition.
In the preferred embodiment, the composition is rendered having an improved refractive index (RI) by adding a compound having formula
in a dropwise manner, to the organoalkoxysilane compound. A compound having formula
x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from Ci to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O can be selected from any one or a mixture of two or more of tetramethoxytitanium, tetraethoxytitanium, tetrapropoxytitanium, tetrabutoxytitanium, tetrabutoxyhafnium, tetrapropoxyhafnium, tetraethoxyhafnium, tetramethoxyhafnium, tetramethoxyrutherfordium, tetraethoxyrutherfordium, tetrapropoxyrutherfordium, tetrabutoxyrutherfordium, tetrabutoxyvanadium, tetrapropoxyvanadium, tetraethoxyvanadium, tetramethoxyvanadium, tetramethoxyniobium, tetraethoxyniobium, tetrapropoxyniobium, tetrabutoxyniobium, tetrabutoxytantalum, tetrapropoxytantalum, tetraethoxytantalum, tetramethoxytantalum, tetramethoxydubnium, tetraethoxydubnium, tetrapropoxydubnium, tetrabutoxydubnium,tetraphenoxytitanium, tetraphenoxyzirconium, tetraphenoxyhafnium, tetraphenoxyrutherfordium, tetraphenoxyvanadium, tetraphenoxyniobium, tetraphenoxytantalum, tetraphenoxydubnium, tetrakis(cyclopentyloxy)titanium, tetrakis(cyclopentyloxy)zirconium, tetrakis(cyclopentyloxy)hafnium, tetrakis(cyclopentyloxy)rutherfordium, tetrakis(cyclopentyloxy)vanadium, tetrakis(cyclopentyloxy)niobium, tetrakis(cyclopentyloxy)tantalum, tetrakis(cyclopentyloxy)dubnium, tetrakis(cyclohexyloxy)titanium, tetrakis(cyclohexyloxy)zirconium, tetrakis(cyclohexyloxy)hafhium, tetrakis(cyclohexyloxy)rutherfordium, tetrakis(cyclohexyloxy)vanadium, tetrakis(cyclohexyloxy)niobium,
tetrakis(cyclohexyloxy)tantalum, tetrakis(cyclohexyloxy)dubnium, tetrakis(cycloheptyloxy)titanium, tetrakis(cycloheptyloxy)zirconium, tetrakis(cycloheptyloxy)hafnium, tetrakis(cycloheptyloxy)vanadium, tetrakis(cycloheptyloxy)niobium, tetrakis(cycloheptyloxy)tantalum, tetrakis(cycloheptyloxy)dubnium, tetrakis(cyclooctyloxy)titanium, tetrakis(cyclooctyloxy)zirconium, tetrakis(cyclooctyloxy)hafnium, tetxakis(cyclooctyloxy)rutherfordium, tetrakis(cyclooctyloxy)vanadium, tetrakis(cyclooctyloxy)niobium,
tetralds(cyclooctyloxy)tantalum,tetrakis(cyclooctyloxy)du^
tetraethoxyselenium, tetrapropoxyselenium, tetrabutoxyselenium, tetramethoxytellurium, tetraethoxytellurium, tetrapropoxytellurium, tetrabutoxytellurium, tetramethoxypolonium, tetraethoxypolonium, tetrapropoxypolonium, tetrabutoxypolonium, pentakis(cyclopentyloxy)hafnium, pentaphenoxyhafnium, butoxytetrapropoxyhafnium, pentapropoxyhafnium, hexapropoxyniobium, hexaphenoxyniobium, hexakis(cyclopentyloxy)niobium, niobium n-propoxide pentakis(cyclopentyloxy)selenium, pentaphenoxyselenium, butoxytetrapropoxyselenium, pentapropoxyselenium, hexapropoxyselenium, hexaphenoxyselenium, selenium hexa-iso- propoxide, hexakis(cyclopentyloxy)selenium, tetrapropoxyzirconium, zirconium ethoxide, zirconium propoxide, zirconium isopropoxide, zirconium butoxide, and zirconium t- butoxide.
Amongst the elements in Group 16, elements from period 4 to 7 (Se, Te, Po and Lv) are preferred due to the presence of vacant orbitals which can be involved in formation of coordination bond. For example, tetraethoxyselenium can be used in an amount of 10 to 70 mole % in the composition.
The compound having formula
the present invention can be provided in solid or fluid form. In the case where solid form is provided, it is preferably added to the same solvent as it might be used during the previous step, such that the compound having formula
can be added into the organoalkoxysilane compound in a dropwise manner. A resinous composition can be obtained and it is preferably filtered and vacuum heated to remove any volatile components therein. In the present invention, the step of hydrolysing the organoalkoxysilane, reacting it with the ethylenically unsaturated monomer and the compound having formula
conducted in an inert condition at a temperature of 0 to 200 °C under a pressure of 0 to 5 atm. Temperature exceeding 200 °C may cause decomposition and melting of the reaction product.
EXAMPLE
The examples of a precursor for LED encapsulating material formed from the composition and its method of producing the precursor will now be described. The following examples and experiments are for illustrative purposes only and not intended to limit the scope of this disclosure.
EXAMPLE 1
22.3 g of diphenyldimethylsilane (DDS) having a molecular weight of 383.68 g/mol was mixed with 12 g of ethanol. The mixture was left to react for 15 minutes. Subsequently, 0.04 g of isobornyl acrylate (IBOA) having a molecular weight of 208.3 g/mol was added therein and left to react for another 1 hour. Then, 11.5 g of zirconium propoxide having a molecular weight of 383.68 g/mol was added in a dropwise manner therein and left to react for another 1 hour. Thereinafter, the mixture was subjected to filtration to remove unreacted zirconium particles. The filtrate appeared clear. Further, the filtrate has a refractive index (RI) of approximately 1.59-1.65 at 589 nm.
EXAMPLE 2
22.3 g of diphenyldimethylsilane (DOS) having a molecular weight of 383.68 g/mol was mixed with 2.5 g of hydrochloric acid (HCl) and 12 g of ethanol. The mixture was left to react for 15 minutes. Subsequently, 4.16 g of isobornyl acrylate (ΓΒΟΑ) having a molecular weight of 208.3 g mol was added therein and left to react for another 1 hour. Then, 7.67 g of zirconium propoxide (ZPO) having a molecular weight of 383.68 g/mol was added therein and left to react for another 1 hour. Thereinafter, the mixture was subject to neutralisation using sodium carbonate, followed by filtration to remove unreacted zirconium particles. The filtrate appeared clear. Further, the filtrate has refractive index (RI) of approximately 1.59-1.65 at 589nm.
EXAMPLE 3
22.3 g of diphenyldimethylsilane (DDS) having a molecular weight of 248.3 g/mol was mixed with 2.5 g of hydrochloric acid (HCl) and 12 g of ethanol. The mixture was left to react for 15 minutes. Thereinafter, 2.6 g of methoxy(dimethyl)vinylsilane having a molecular weight of 130.2 g/mol was further added therein and left to react for another 1 hour. Subsequently, 11.5 g of zirconium propoxide (ZPO) having a molecular weight of 383.68 g/mol was added in a dropwise manner therein and left to react for another 1 hour. Thereinafter, the mixture was subjected to neutralisation using sodium carbonate, followed by filtration to remove unreacted zirconium particles. The filtrate appeared clear. Further, the filtrate has a refractive index (RI) of approximately 1.59-1.65 at 589 nm.
Claims
1. An organosiloxane composition for use as an encapsulating material for a light emitting element comprising a reaction product of:
(a) a compound having formula M-COR1)^ where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from O to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O;
(b) an organoalkoxysilane compound; and
(c) an organosilane having formula (R4)-0-Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of Ci to C3 alkyl, Ci to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl in the presence of a catalyst.
2. A composition according to claim 1 further comprising an ethylenically unsaturated monomer comprising an isobornyl group.
3. A composition according to claim 2, wherein the ethylenically unsaturated monomer comprising an isobornyl group is isobornyl methacrylate or acrylate or a mixture thereof.
4. A composition according to claim 1 or 2 is a reaction product made in the presence of a solvent selected from methanol, ethanol, propanol, butanol, ethyl acetate, acetone, isopropyl alcohol, dichloromethane, chloroform, dimethylformamide, dimethyl sulfoxide and/or acetone nitride.
5. A composition according to claim 1 or 2, wherein the organoalkoxysilane compound having a formula (R2)m-Si-(OR3)n, wherein m and n are positive integers 0 to 4, R2and R3 are independently selected from a group consisting of Ci to C3 alkyl, C2 to C3
alkenyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or 0, where each of which may have a vinyl or acryloyl functional group.
6. A composition according to any one of claims 1 to 5, wherein the organoalkoxysilane is selected from any one or a mixture of two or more of tetracyclopentylorthosilicate, tetracyclohexylorthosilicate, tetracycloheptylorthosilicate, tetracyclooctylorthosilicate, cyclopentyltris(cyclopentyloxy)silane, cyclohexyltris(cyclohexyloxy)silane, cycloheptyltris(cycloheptyloxy)silane, cyclooctyltris(cyclooctyloxy)silane, dicyclopentylbis(cyclopentyloxy)silane, dicyclohexylbis(cyclohexyloxy)silane, dicycloheptylbis(cycloheptyloxy)silane, dicyclooctylbis(cyclooctyloxy)silane, tricyclopentyl(cyclopentyloxy)silane, tricyclohexyl(cyclohexyloxy)silane, tricycloheptyl(cycloheptyloxy)silane, tricyclooctyl(cyclooctyloxy)silane, tris(cycloheptyloxy)(cyclopentyl)silane, tris(cyclooctyloxy)(cyclopentyl)silane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxy)(cyclohexyl)silane, cyclohexyltris(cyclooctyloxy)silane, cycloheptyltris(cyclopentyloxy)silane, cycloheptyltris(cyclohexyloxy)silane, cycloheptyltris(cyclooctyloxy)silane, cyclohexyltris(cyclopentyloxy)silane, tris(cycloheptyloxy)(cyclohexyl)silane, cyclohexyltris(cyclooctyloxy)silane, cyclooctyltris(cyclopentyloxy)silane, tris(cyclohexyloxy)(cyclooctyl)silane, tris(cycloheptyloxy)(cyclooctyl)silane, bis(cyclohexyloxy)dicyclopentylsilane, bis(cycloheptyloxy)dicyclopentylsilane, bis(cyclooctyloxy)dicyclopentylsilane, dicyclohexylbis(cyclopentyloxy)silane, bis(cycloheptyloxy)dicyclohexylsilane, dicyclohexylbis(cyclooctyloxy)silane, dicycloheptylbis(cyclopentyloxy)silane, dicycloheptylbis(cyclohexyloxy)silane, dicycloheptylbis(cyclooctyloxy)silane, dicyclooctylbis(cyclopentyloxy)silane, bis(cyclohexyloxy)dicyclooctylsilane, bis(cycloheptyloxy)dicyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cyclohexyloxytricyclopentylsilane, tricycloheptyl(cyclohexyloxy)silane, cyclohexyloxytricyclooctylsilane, cycloheptyloxytricyclopentylsilane,
cycloheptyloxytricyclohexylsilane, cycloheptyloxytricyclooctylsilane, cyclooctyloxytricyclopentylsilane, tricyclohexyl(cyclooctyloxy)silane, tricycloheptyl(cyclooctyloxy)silane, tetrapyridin-4-yl orthosilicate, tetra(2H-pyran-4-yl) orthosilicate, tetra(2H-thiopyran-4-yl) orthosilicate, 4,4',4"-(pyridin-4- ylsilanetriyl)tris(oxy)tripyridine, tris(2H-pyran-4-yloxy)(2H-pyran-4-yl)silane, tris(2H- thiopyran-4-yloxy)(2H-thiopyran-4-yl)silane, 4-(tris(2H-pyran-4-yloxy)silyl)pyridine, 4- (tris(2H-thiopyran-4-yloxy)silyl)pyridine, 4,4',4"-((2H-pyran-4- yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H-pyran-4-yl)silane, 4,4',4"-((2H-pyran-4-yl)silanetriyl)tris(oxy)tripyridine, tris(2H-thiopyran-4-yloxy)(2H- pyran-4-yl)silane, dipyridin-4-ylbis(pyridin-4-yloxy)silane, bis(2H-pyran-4-yloxy)di(2H- pyran-4-yl)silane, bis(2H-thiopyran-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran- 4-yloxy)dipyridin-4-ylsilane, bis(2H-thiopyran-4-yloxy)dipyridin-4-ylsilane, di(2H- pyran-4-yl)bis(pyridin-4-yloxy)silane, bis(2H-thiopyran-4-yloxy)di(2H-pyran-4-yl)silane, bis(pyridin-4-yloxy)di(2H-thiopyran-4-yl)silane, bis(2H-pyran-4-yloxy)di(2H-thiopyran- 4-yl)silane, 4,4',4"-((pyridin-4-yloxy)silanetriyl)tripyridine, (2H-pyran-4-yloxy)tri(2H- pyran-4-yl)silane, (2H-thiopyran-4-yloxy)tri(2H-thiopyran-4-yl)silane, 4,4'-((2H-pyran-4- yloxy)(2H-pyran-4-yl)silanediyl)dipyridine, 4,4'-((2H-thiopyran-4-yloxy)(2H-thiopyran- 4-yl)silanediyl)dipyridine, 4-(di(2H-pyran-4-yl)(pyridin-4-yl)silyloxy)pyridine, (2H- thiopyran-4-yloxy)di(2H-pyran-4-yl)(2H-thiopyran-4-yl)silane, 4-(pyridin-4-yldi(2H- thiopyran-4-yl)silyloxy)pyridine, (2H-pyran-4-yloxy)(2H-pyran-4-yl)di(2H-thiopyran-4- yl)silane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane,ethyltrimethoxysilane, ethyltriethoxysilane, ethyltripopoxysilane, propyltrimethoxysilane,
propyltriethoxysilane, propyltripropoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, phenyltrimethoxysilane, 3-acryloxypropyl trimethoxysilane, 3- acryloxypropyl triethoxysilane, 3-acryloxypropyl tripropoxysilane, methoxydimethylvinylsilane, ethoxydimethylvinylsilane, propoxydimethylvinylsilane, methoxydiethylvinylsilane, ethoxydiethylvinylsilane, propoxydiethylvinylsilane, methoxydipropylvinylsilane, ethoxydipropylvinylsilane, propoxydipropylvinylsilane,
dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldipropoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldipropoxysilane, dipropyldimethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane and diphenyldipropoxysilane.
7. A composition according to any one of claims 1 to 6, wherein the compound having formula
selected from any one or a mixture of two or more of tetramethoxytitamum, tetraethoxytitanium, tetrapropoxytitamum, tetrabutoxytitamum, tetrabutoxyhafnium, tetrapropoxyhafnium, tetraethoxyhafnium, tetramethoxyhafnium, tetramethoxyrutherfordium, tetraethoxyrutherfordium, tetrapropoxyrutherfordium, tetrabutoxyrutherfordium, tetrabutoxyvanadium, tetrapropoxyvanadium,
tetraethoxyvanadium, tetramethoxyvanadium, tetramethoxyniobium, tetraethoxyniobium, tetrapropoxyniobium, tetrabutoxyniobium, tetrabutoxytantalum, tetrapropoxytantalum, tetraethoxytantalum, tetxamethoxytantalum, tetramethoxydubnium, tetraethoxydubmum, tetrapropoxydubnium, tetrabutoxydubnium,tetraphenoxytitanium,
tetraphenoxyzirconium, tetraphenoxyhafnium, tetraphenoxyrutherfordium,
tetraphenoxyvanadium, tetraphenoxyniobium, tetraphenoxytantalum,
tetraphenoxydubnium, tetrakis(cyclopentyloxy)titanium,
tetrakis(cyclopentyloxy)zirconium, tetrakis (cyclopentyloxy)hafnium,
tetrakis(cyclopentyloxy)rutherfordium, tetrakis(cyclopentyloxy)vanadium,
tetrakis(cyclopentyloxy)niobium, tetrakis(cyclopentyloxy)tantalum,
tetrakis(cyclopentyloxy)dubnium, tetrakis(cyclohexyloxy)titanium,
tetrakis(cyclohexyloxy)zirconium, tetrakis(cyclohexyloxy)hafnium,
tetrakis (cyclohexyloxy)rutherfordium, tetrakis(cyclohexyloxy) vanadium,
tetrakis(cyclohexyloxy)niobium, tetrakis(cyclohexyloxy)tantalum,
tetrakis(cyclohexyloxy)dubnium, tetrakis(cycloheptyloxy)titanium,
tetrakis(cycloheptyloxy)zirconium, tetrakis(cycloheptyloxy)hafnium,
tetrakis(cycloheptyloxy)vanadium, tetrakis(cycloheptyloxy)niobium,
tetrakis(cycloheptyloxy)tantalum, tetrakis(cycloheptyloxy)dubnium,
tetrakis(cyclooctyloxy)titanium, tetrakis(cyclooctyloxy)zirconium, tetrakis(cyclooctyloxy)hafhium, tetrakis(cyclooctyloxy)rutherfordium,
tetrakis(cyclooctyloxy)vanadium, tetrakis(cyclooctyloxy)niobium,
tetrakis(cyclooctyloxy)tantalum,tettalds(cyclooctyloxy)dubnium,telTamethoxyseleni tetraethoxyselenium, tetrapropoxyselenium, tetrabutoxyselenium, tetramethoxytellurium, tetraethoxytellurium, tetrapropoxytellurium, tetrabutoxytellurium, tetramethoxypolonium, tetraethoxypolonium, tetrapropoxypolonium, tetrabutoxypolonium,
pentakis(cyclopentyloxy)hafnium, pentaphenoxyhafnium, butoxytetrapropoxyhafnium, pentapropoxyhafnium, hexapropoxyniobium, hexaphenoxyniobium,
hexakis(cyclopentyloxy)niobium, niobium n-propoxide,
pentakis(cyclopentyloxy)selenium, pentaphenoxyselenium, butoxytetrapropoxyselenium, pentapropoxyselenium, hexapropoxyselenium, hexaphenoxyselenium, selenium hexa- iso-propoxide, hexakis(cyclopentyloxy)selenium, tetrapropoxyzirconium, zirconium ethoxide, zirconium propoxide, zirconium isopropoxide, zirconium butoxide and zirconium t-butoxide.
8. A composition according to any one of claims 1 to 7, wherein the organosilane having formula (R4)-0-Si(C=C)(R5)2 is any one or a mixture of two of more of methoxydimethyl(vinyl)silane, ethoxydiethyl(vinyl)silane, vinylsilanol, trimethoxy(vinyl)silane, triethoxy(vinyl)silane, phenoxydiphenyl(vinyl)silane, dicyclopentyl(cyclopentyloxy)(vinyl)silane, dicyclohexyl(cyclohexyloxy)(vinyl)silane, dicyclopentyl(methoxy)(vinyl)silane, dicyclohexyl(methoxy)(vinyl)silane, methoxydiphenyl(vinyl)silane, ethoxydiphenyl(vinyl)silane and diphenyl(propoxy)(vinyl)silane.
9. A composition according to any one of claims 1 to 8, wherein the catalyst is hydrochloric acid, sulfuric acid, trifilic acid, nitric acid, phosphoric acid, ethanoic acid, potassium hydroxide, sodium hydroxide or barium hydroxide.
10. A composition according to any one of claims 1 to 9, wherein the a compound having formula M-iOR1^ is present in an amount of 10 to 70 mole % of the composition.
11. A composition according to any one of claims 1 to 10, wherein the ethylenically unsaturated monomer comprising an isobornyl group is present in an amount of 10 to 50 mole % of the composition.
12. A composition according to any one of claims 1 to 11, wherein the organosilane is present in an amount of 10 to 50 mole % of the composition.
13. A composition according to any one of claims 1 to 12, wherein the organoalkoxysilane compound is present in an amount of 10 to 80 mole % of the composition.
14. A method of producing an organosiloxane composition according to any one of the preceding claims, comprising steps of:
(a) hydrolysing an organoalkoxysilane compound in a pH environment of 1 to 12;
(b) reacting an organosilane having formula (R4)-0-Si(C=C)(R5)2, R4 and R5 are independently selected from a group consisting of G to C3 alkyl, G to C3 alkoxy, hydrogen, C6 aryl and/or C5 to C8 cycloalkyl with the hydrolysed organoalkoxysilane compound; and
(c) adding a compound having formula M-fOR1^, where x is an integer 4 to 6, M is an element selected from Group 4, 5 or 16, R1 is selected from G to C4 alkyl, C5 to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O into the reacted organoalkoxysilane compound, in which the hydrolysing, reacting and adding steps are conducted in an inert condition at a temperature of 0 to 200 °C under a pressure of 0 to 5 atm.
15. A method according to claim 14 further comprising a step of reacting an ethylenically unsaturated monomer comprising an isobornyl group with the hydrolysed organoalkoxysilane compound.
16. A method according to claim 14 or 15, wherein the organoalkoxysilane has a formula (R2)m-Si-(OR3)n, wherein m and n are positive integers 0 to 4, R2 and R3 are independently selected from a group consisting of Ci to C3 alkyl, C2to C3 alkenyl, Cs to C8 cycloalkyl, C6 aryl, C6 heterocycloalkyl containing element N, S or O, where each of which may have a vinyl or acryloyl functional group.
17. A method according to any one of claims 14 to 16, wherein the composition has a refractive index of 1.59 to 1.65 at 589 nm.
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