JP2014533767A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP2014533767A JP2014533767A JP2014543430A JP2014543430A JP2014533767A JP 2014533767 A JP2014533767 A JP 2014533767A JP 2014543430 A JP2014543430 A JP 2014543430A JP 2014543430 A JP2014543430 A JP 2014543430A JP 2014533767 A JP2014533767 A JP 2014533767A
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- JP
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- Prior art keywords
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- chemical formula
- organopolysiloxane
- carbon atoms
- sio
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 141
- 229920001296 polysiloxane Polymers 0.000 claims description 105
- 239000000126 substance Substances 0.000 claims description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 47
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 44
- 125000003700 epoxy group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 229910052710 silicon Inorganic materials 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000004065 semiconductor Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000004448 titration Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 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
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- 238000001746 injection moulding Methods 0.000 description 1
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- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
Description
(R1R2 2SiO1/2)a(R3R4SiO2/2)b(R5SiO3/2)c(SiO2)d
(R1R2 2SiO1/2)a(R6R7SiO2/2)l(R8R9SiO2/2)m(R5SiO3/2)c
[ReSiO3/2]
[RaRb 2SiO1/2]p[ReSiO3/2]q
(RaRb 2Si)2O
R3SiO(R2SiO)nSiR3
(R3SiO1/2)h(R2SiO2/2)i(RSiO3/2)j(SiO2)k
(R3SiO1/2)d(R2SiO2/2)e(RSiO3/2)f(SiO4/2)g
(R16 3SiO1/2)i(R17 2SiO2/2)j
オルガノポリシロキサンに対する1H−NMR分析は、次の条件で行った。
〈1H−NMR分析内容〉
測定器機:Varian Unity Inova 500MHz NMR
使用溶媒:acetone−d6
測定条件:
Pulse sequence:s2pul
Sweep width:8012.8hz
Acquisition time:2.045 sec
Delay time:2 sec
Pulse width:45 degree pulse(8.10 usec)
Number of scan:16
トルエン500mL、イソプロピルアルコール(IPA)495mL及び水(distilled water)5mLを配合し、測定用溶媒を製造した。また、ベース溶媒(base solution)として0.1Nの濃度のKOH溶液(溶媒:イソプロピルアルコール(IPA))を準備し、標識子(indicator)としては、アルファ−ナフトルベンゼイン(alpha−naphtholbenzein)(pH:0.8〜8.2 yellow、10.0 blue green)を準備した。次いで、試料約1〜2gを採取し、測定用溶媒6gに溶かした後、標識子を添加した後、ベース溶媒で滴定した。滴定完了時点で使用されたベース溶媒の量で酸価(acid value)をmgKOH/gの単位で求めた。
ポリフタルアミド(PPA)で製造された3017 LEDパッケージを使用して素子特性を評価する。具体的に、ポリフタルアミドカップ内に硬化性組成物をディスフェンシングし、70℃で1時間維持した後、さらに150℃で1時間維持して硬化させて、表面実装型LEDを製造する。
(1)熱衝撃テスト
製造されたLEDを−40℃で30分間維持し、さらに100℃で30分間維持することを1サイクルにして、上記を50回、すなわち50サイクル繰り返した後、室温で維持し、剥離状態を調査し、耐熱衝撃性を評価する。評価時には、同一硬化性組成物で製造されたLED 10個に対してそれぞれ上記のような試験を行い、剥離されたLEDの数を下記表1に記載した。
製造されたLEDを85℃及び85%相対湿度の条件で維持した状態で20mAの電流を流しながら300時間動作させる。次いで、動作前の初期輝度に比べて上記動作後の後期輝度の減少率を測定し、下記基準によって評価する。
〈評価基準〉
○:初期輝度に比べて輝度減少率が10%以下
×:初期輝度に比べて輝度減少率が10%超過
オクタメチルシクロテトラシロキサン(octamethylcyclotetrasiloxane)60.00g、オクタフェニルシクロテトラシロキサン(octaphenylcyclotetrasiloxane)106.96g、オクタフェニル−POSS(octaphenyl−polyhedral oligomericsil sesquioxane)10.0gオクタグリシジル−POSS(octaglycidyl−polyhedral oligomeric silsesquioxane)21.0g及びジビニルテトラメチルジシロキサン(divinyltetramethyldisiloxane)12.56gを混合し、上記混合物に触媒としてテトラメチルアンモニウムヒドロキシド(TMAH;tetramethylammonium hydroxide)0.63mLを配合した。その後、上記触媒が配合された混合物を115℃の温度で反応させて、下記化学式Cで表示される透明なオイル形態のポリシロキサンを収得した。上記ポリシロキサンの25℃での粘度は、20,000cPであり、分子量は、約5,400であった。また、1H−NMRで測定されるスペクトル上でアルコキシ基から由来するピークは観察されず、酸価は、約0.006mgKOH/gと測定された。
[ViMe2SiO1/2]2[Me2SiO2/2]22[Ph2SiO2/2]15[PhSiO3/2]2[EpSiO3/2]4
オクタメチルシクロテトラシロキサン及びオクタフェニルシクロテトラシロキサンを使用せず、その代わりに、テトラメチルテトラフェニルシクロテトラシロキサン(tetramethyltetraphenylcyclotetrasiloxane)183。71gを配合し、ジビニルテトラメチルジシロキサンの配合量を12.10gに変更したことを除いて、合成例3と同一の方式でポリシロキサンを合成した。上記ポリシロキサンは、下記化学式Hで表示され、透明なオイル形態であった。上記ポリシロキサンの25℃での粘度は、18,800cPであり、分子量は、約4,300であった。また、1H−NMRで測定されるスペクトル上でアルコキシ基から由来するピークは、観察されず、酸価は、約0.008mgKOH/gと測定された。
[ViMe2SiO1/2]2[MePhSiO2/2]32[PhSiO3/2]4[EpSiO3/2]4
合成例1で製造されたオルガノポリシロキサン(A)に公知の方式で合成したものであって、それぞれ下記の化学式G〜Hで表示される化合物を混合し、ヒドロシリル化反応によって硬化することができる硬化性組成物を製造した(配合量:オルガノポリシロキサン(A):25g、化学式Gの化合物:50g、化学式Hの化合物:18g)。次いで、上記組成物にPt(0)の含量が2ppmになるように触媒(Platinum(0)−1、3−divinyl−1、1、3、3−tetramethyldisiloxane)を配合し、均一に混合した後、脱泡器で気泡を除去し、硬化性組成物を製造した。
(HMe2SiO1/2)(PhSiO3/2)3.5
(HMe2SiO1/2)2(Ph2SiO2/2)1.2
合成例2で製造されたオルガノポリシロキサン(B)に公知の方式で合成したものであって、下記化学式I及びJで表示される化合物を混合し、ヒドロシリル化反応によって硬化することができる硬化性組成物を製造した(配合量:オルガノポリシロキサン(B):25g、化学式Iの化合物:50g、化学式Jの化合物:18g)。次いで、上記組成物にPt(0)の含量が2ppmになるように触媒(Platinum(0)−1、3−divinyl−1、1、3、3−tetramethyldisiloxane)を配合し、均一に混合した後、脱泡器で気泡を除去し、硬化性組成物を製造した。
(ViMe2SiO1/2)(PhSiO3/2)3.5
(HMe2SiO1/2)3(Ph2SiO2/2)1.2
オルガノポリシロキサン(A)を使用しないことを除いて、実施例1と同一に硬化性組成物を製造した。
オルガノポリシロキサン(A)の代わりに、下記化学式Pのオルガノポリシロキサンを使用したことを除いて、実施例1と同一に硬化性組成物を製造した。
[ViMe2SiO1/2]2[Me2SiO2/2]22[Ph2SiO2/2]15[PhSiO3/2]2
オルガノポリシロキサン(B)の代わりに、下記化学式Qのオルガノポリシロキサンを使用したことを除いて、実施例2と同一に硬化性組成物を製造した。
[ViMe2SiO1/2]2[MePhSiO2/2]32
Claims (18)
- (A)下記化学式1の平均組成式を有するオルガノポリシロキサン;及び
(B)ケイ素原子に結合された水素原子を含むオルガノポリシロキサンを含む硬化性組成物:
[化学式1]
(R1R2 2SiO1/2)a(R3R4SiO2/2)b(R5SiO3/2)c(SiO2)d
上記化学式1で、R1は、エポキシ基または炭素数2以上の1価炭化水素基であり、R2は、エポキシ基または炭素数1〜4のアルキル基であり、R3及びR4は、それぞれ、独立して炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、エポキシ基または炭素数6〜25のアリール基であり、R5は、炭素数1〜20のアルキル基、エポキシ基または炭素数6〜25のアリール基であり、R1、R3及びR4のうち少なくとも1つは、アルケニル基であり、R1〜R5のうち少なくとも1つは、エポキシ基であり、aは、正の数であり、bは、0または正の数であり、cは、正の数であり、dは、0または正の数であり、b/aは、5以上であり、b/cは、5以上である。 - (A)オルガノポリシロキサンに含まれる全体ケイ素原子に対する上記(A)オルガノポリシロキサンに含まれる全体アルケニル基のモル比(Ak/Si)が0.02〜0.2である、請求項1に記載の硬化性組成物。
- (A)オルガノポリシロキサンに含まれる全体ケイ素原子に対する上記(A)オルガノポリシロキサンに含まれる全体エポキシ基のモル比(Ep/Si)が0.4以下である、請求項1に記載の硬化性組成物。
- (A)オルガノポリシロキサンに含まれる全体ケイ素原子に対する上記(A)オルガノポリシロキサンに含まれる全体アリール基のモル比(Ar/Si)が0.3以上である、請求項1に記載の硬化性組成物。
- 化学式1のb/(a+b+c+d)が0.5以上である、請求項1に記載の硬化性組成物。
- 化学式1のb/(b+c)が0.5以上である、請求項1に記載の硬化性組成物。
- (A)オルガノポリシロキサンは、下記化学式2の平均組成式を有する、請求項1に記載の硬化性組成物:
[化学式2]
(R1R2 2SiO1/2)a(R6R7SiO2/2)l(R8R9SiO2/2)m(R5SiO3/2)c
上記化学式2で、R1、R2及びR5は、化学式8で定義した通りであり、R6は、エポキシ基または炭素数6〜25のアリール基であり、R7、R8及びR9は、それぞれ、独立して炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、エポキシ基または炭素数6〜25のアリール基であり、R1、R7、R8及びR9のうち少なくとも1つは、アルケニル基であり、R1、R2及びR5〜R9のうち少なくとも1つは、エポキシ基であり、a+l+m+cを1に換算したとき、aは、0.01〜0.10であり、lは、0〜0.90であり、mは、0〜0.90であり、cは、0.01〜0.30であり、(l+m)/aは、5以上であり、(l+m)/cは、5以上である。 - (A)オルガノポリシロキサンは、1H NMRスペクトルでケイ素原子に結合されたアルケニル基から由来する面積(Ak)に対してケイ素原子に結合されたアルコキシ基から由来するピークの面積(OR)の比率(OR/Ak)が0.05以下である、請求項1に記載の硬化性組成物。
- (A)オルガノポリシロキサンは、KOH滴定による酸価が0.05mgKOH/g以下である、請求項1に記載の硬化性組成物。
- (B)オルガノポリシロキサンは、下記化学式9の化合物または下記化学式10の平均組成式を有する化合物である、請求項1に記載の硬化性組成物:
[化学式9]
R15 3SiO(R15 2SiO)nSiR15 3
上記化学式9で、R15は、それぞれ、独立して水素または1価の炭化水素基であり、R15のうち1つまたは2つ以上は、水素原子であり、R15のうち少なくとも1つは、アリール基であり、nは、1〜100である:
[化学式10]
(R16 3SiO1/2)h(R16 2SiO2/2)i(R16SiO3/2)j(SiO2)k
上記化学式10で、R16は、それぞれ、独立して水素または1価の炭化水素基であり、R16のうち1つまたは2つ以上は、水素原子であり、R16のうち少なくとも1つは、アリール基であり、h+i+j+kを1に換算したとき、hは、0.1〜0.8であり、iは、0〜0.5であり、jは、0.1〜0.8であり、kは、0〜0.2であり、但し、i及びkは、同時に0ではない。 - 下記化学式11の平均組成式を有するオルガノポリシロキサンをさらに含む、請求項1に記載の硬化性組成物:
[化学式11]
(R14 3SiO1/2)d(R14 2SiO2/2)e(R14SiO3/2)f(SiO4/2)g
上記化学式10で、R14は、それぞれ、独立して1価炭化水素基であり、但し、R14のうち少なくとも1つは、アルケニル基であり、R14のうち少なくとも1つは、アリール基であり、d+e+f+gを1に換算したとき、dは、0.05〜0.5であり、eは、0〜0.3であり、fは、0.6〜0.95であり、gは、0〜0.2であり、但し、f及びgは、同時に0ではなく、(d+e)/(d+e+f+g)は、0.2〜0.7であり、e/(e+f+g)は、0.3以下であり、f/(f+g)は、0.8以上である。 - 請求項1に記載の硬化性組成物の硬化物で封止された半導体素子。
- 請求項1に記載の硬化性組成物の硬化物で封止された発光ダイオード。
- 請求項16に記載の発光ダイオードを含む液晶ディスプレイ。
- 請求項16に記載の発光ダイオードを含む照明器具。
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