JP2014019800A - エネルギー線硬化型樹脂組成物及びその硬化物 - Google Patents
エネルギー線硬化型樹脂組成物及びその硬化物 Download PDFInfo
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- JP2014019800A JP2014019800A JP2012160182A JP2012160182A JP2014019800A JP 2014019800 A JP2014019800 A JP 2014019800A JP 2012160182 A JP2012160182 A JP 2012160182A JP 2012160182 A JP2012160182 A JP 2012160182A JP 2014019800 A JP2014019800 A JP 2014019800A
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- curable resin
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- acrylate
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- 125000003118 aryl group Chemical group 0.000 claims description 17
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
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- SOLUNJPVPZJLOM-UHFFFAOYSA-N trizinc;distiborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-][Sb]([O-])([O-])=O.[O-][Sb]([O-])([O-])=O SOLUNJPVPZJLOM-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Abstract
可視光透過率、耐光性に優れ、Tgが高く、硬化収縮率、水蒸気透過度の低い、エネルギー線硬化型樹脂組成物を提供する。
【解決手段】
(1)分子中に2つ以上のオキセタン環を有する化合物(A)を2種類以上含有するエネルギー線硬化型樹脂組成物
(2)エネルギー線硬化型樹脂組成物の反応性基を有さない有機化合物成分において、重量平均分子量10,000g/mol以上の有機化合物成分の含有量が1.5重量%未満であることを特徴とする請求項1に記載のエネルギー線硬化型樹脂組成物。
(3)分子中に2つ以上のオキセタン環を有する化合物(A)が少なくとも下記一般式(1)及び/または下記一般式(2)で表されるオキセタン環を有する化合物である(1)または(2)のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
【選択図】なし
Description
(1)分子中に2つ以上のオキセタン環を有する化合物(A)を2種類以上含有するエネルギー線硬化型樹脂組成物。
(2)エネルギー線硬化型樹脂組成物の反応性基を有さない有機化合物成分において、重量平均分子量10,000g/mol以上の有機化合物成分の含有量が1.5重量%未満であることを特徴とするエネルギー線硬化型樹脂組成物。
(3)分子中に2つ以上のオキセタン環を有する化合物(A)が少なくとも下記一般式(1)で表されるオキセタン環を有する化合物である(1)または(2)のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
(5)(1)に記載の分子中に2つ以上のオキセタン環を有する化合物(A)として、上記式(1)記載の化合物及び上記式(2)記載の化合物を含有する(1)に記載のエネルギー線硬化型樹脂組成物。
(6)分子中に2つ以上のオキセタン環を有する化合物(A)を2種類以上含有し、エネルギー線硬化型樹脂組成物の全有機化合物成分が重量平均分子量10,000g/mol以下で20℃〜80℃で可溶な成分から構成された(1)〜(5)のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
(7)エポキシ化合物(B)を含有する(1)乃至(6)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(8)エポキシ化合物(B)が脂環式エポキシ化合物である(1)乃至(7)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(9)エポキシ化合物(B)が分子中に2個以上のエポキシ基を有する化合物である(1)乃至(8)に記載のエネルギー線硬化型樹脂組成物。
(10)エポキシ化合物(B)を20〜70質量部含有する(1)乃至(9)に記載のエネルギー線硬化型樹脂組成物。
(11)分子中に2つ以上のオキセタン環を有する化合物(A)を30〜80質量部含有する(1)乃至(10)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(12)光カチオン重合開始剤(C)を含有する(1)乃至(11)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(13)光カチオン重合開始剤(C)がスルホニウム塩、ヨードニウム塩、ホスホニウム塩、アンモニウム塩、アンチモン酸塩から選択される(1)乃至(12)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(14)微粒子(D)を含有する(1)乃至(13)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(15)微粒子(D)の一次粒径が100nm以下である(14)に記載のエネルギー線硬化型樹脂組成物。
(16)E型粘度計で測定した25℃での粘度が10mPa・s以上である(1)乃至(15)の何れか一項に記載のエネルギー線硬化型樹脂組成物。
(17)(1)乃至(16)の何れか一項に記載の封止材用エネルギー線硬化型樹脂組成物。
(18)(1)乃至(17)の何れか一項に記載の有機ELディスプレイ封止材用エネルギー線硬化型樹脂組成物。
(19)(1)乃至(18)の何れか一項に記載のエネルギー線硬化型樹脂組成物を硬化せしめて得られる硬化物。
(20)厚み100μmでの水蒸気透過率が200g/m2・day/60℃以下である(19)に記載の硬化物。
(21)(16)または(20)の何れか一項に記載の硬化物を搭載する有機ELディスプレイ。
上記の構成により、2種類の2官能のオキセタンが硬化時に相互に硬化系に導入されることとなり、1種類では達成できなかった耐熱性、剛性、屈折率制御、耐水性、低収縮率の効果を達成することが可能となる。
即ち、1種類の2官能のオキセタン化合物のみを使用した場合と相違し、2種類のオキセタン化合物を使用することで、1種類のみを使用した場合と比較して、耐熱性、剛性、屈折率、耐水性を維持しつつ、2種類以上のオキセタン化合物同士が硬化系に複雑に導入されていくため、相乗効果として1種類のみでは達成し得なかった極めて高い耐熱性を奏する硬化物の提供が可能となることが見出された。更に、2種類以上使用することで、耐熱性、剛性、屈折率、収縮率について、制御を行うことが極めて容易になる。
(式中、R1はそれぞれ独立して直接結合または炭素数1〜6の直鎖または分岐鎖状炭化水素基を示し、R2は炭素数1〜15の直鎖若しくは分岐鎖状炭化水素基、または脂環、芳香環、複素環若しくは縮合環を含む炭化水素基を示し、R3はそれぞれ独立して炭素数1〜3の直鎖または分岐鎖状炭化水素基を示す。nは平均値で1〜5の整数を表す。)。
R1としては、炭素数1〜6の直鎖または分岐鎖状炭化水素基が好ましく、炭素数1〜6のアルキレン基がより好ましく、炭素数1〜3のアルキレン基が特に好ましい。
R2としては、炭素数1〜12の直鎖アルキレン基、炭素数1〜12の分岐鎖状アルキレン基、炭素数3〜12のフェニレン基またはシクロアルキレン基を有するアルキレン基が好ましく、炭素数6〜12のフェニレン基を有するアルキレン基が特に好ましい。
R3としては、炭素数1〜3のアルキル基が好ましい。
nとしては、1〜3が好ましい。
尚、上記式(1)の化合物において、R2に脂環、芳香環、複素環、縮合環といった環構造(例えば、フェニレン基、ナフタレン基、炭素数3〜8のシクロアルキレン基)を有するオキセタン化合物を用いると硬化物のTg(ガラス転移点)、剛性、屈折率が向上するため好ましい。
ここで、上記式(1)の化合物において、特に好ましい具体的としては、下記一般式(3)
で表される化合物である。
ここで、特に好ましくは、Zはフェニレン基である。
上記式(2)の化合物を用いることで、硬化収縮率が低く保つことが可能となる。
上記式(2)において、R4は炭素数1〜6の直鎖炭化水素基、さらに好ましくは炭素数1〜3のアルキレン基である。
R5においては、炭素数1〜3の直鎖炭化水素基が好ましく、特に好ましくは炭素数1〜3のアルキル基である。
ジグリシジルエーテル、水添ビスフェノールSジグリシジルエーテル、3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、2−(3,4−エポキシシクロヘキシル−5,5−スピロ−3,4−エポキシ)シクロヘキサン−メタン−ジオキサン、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、ビニルシクロヘキセンオキサイド、4−ビニルエポキシシクロヘキサン、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート、3,4−エポキシ−6−メチルシクロヘキシル−3’,4’−エポキシ−6’−メチルシクロヘキサンカルボキシレート、メチレンビス(3,4−エポキシシクロヘキサン)、ジシクロペンタジエンジエポキサイド、エチレングリコールのジ(3,4−エポキシシクロヘキシルメチル)エーテル、エチレンビス(3,4−エポキシシクロヘキサンカルボキシレート)、エポキシヘキサヒドロフタル酸ジオクチル、エポキシヘキサヒドロフタル酸ジ−2−エチルヘキシル、1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、グリセリントリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル類、1,1,3−テトラデカジエンジオキサイド、リモネンジオキサイド、1,2,7,8−ジエポキシオクタン、1,2,5,6−ジエポキシシクロオクタン等が挙げられる。
さらに、環境及び人体への有害性、ならびに各国の規制を鑑みると、アンチモン元素を含有しないジフェニル[4−(フェニルチオ)フェニル]スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニドを使用することが最も好ましい。本発明の成分(C)の含有量は成分(A)+成分(B)の総量100質量部に対して、0.1〜10質量部であり、好ましくは0.5〜3質量部である。なお、本発明の樹脂組成物においては、光カチオン重合開始剤(C)は単独で用いてもよいし、複数種を混合して用いてもよい。
また、ラジカル型光重合開始剤を併用できる。ラジカル型光重合開始剤であれば、どの光重合開始剤でもよいが、例えば、2−ヒドロキシ−2−メチル−フェニルプロパン−1−オン、1−ヒドロキシシクロヘキシル−フェニルケトンが挙げられる。
尚、透過率(特に、380nm〜780nmでの透過率)を向上させる観点からは、微粒子を含有させないことが好ましい。
本発明においては、1次粒径が100nm以下であることが好ましい。そして、5〜100nmである微粒子が好適に使用できる。100nm以下であることにより、耐擦傷性を付与しつつ、透過率が高い硬化物を提供することが可能となる。
光開始剤の含有割合は通常、樹脂組成物100重量部に対して0.001〜10重量部であり、0.01〜8重量部が好ましい。
各種添加剤の含有量は、通常樹脂組成物100重量部に対して0.001〜10重量部であり、0.01〜8重量部が好ましい。
可塑剤ないし柔軟化剤の含有量は、通常樹脂組成物100重量部に対して1〜90重量部であり、2〜80重量部が好ましい。
本発明の樹脂組成物においては、厚み100μmの60℃での水蒸気透過率が200g/m2・day以下であることが好ましく、100g/m2・dayであることがより好ましく、60g/m2・dayであることが特に好ましい。当該範囲にあることで、水分の透過により、素子にダメージを与えることを有効に防ぐことが可能となる。
(1)下部電極/発光層/上部電極
(2)下部電極/電子輸送層/発光層/上部電極
(3)下部電極/発光層/正孔輸送層/上部電極
(4)下部電極/電子輸送層/発光層/正孔輸送層/上部電極
例えば、上記(4)の層構造を有する有機EL素子は、基板の片面上に、Al−Li合金等からなる下部電極(陰極)を抵抗加熱蒸着法またはスパッタ法によって形成し、次いで有機EL層として、オキサジアゾール誘導体やトリアゾール誘導体等からなる電子輸送層、発光層、TPD等からなる正孔輸送層及び上部電極(陽極)を抵抗加熱蒸着法又はイオンビームスパッタ法等の薄膜形成方法によって順次積層することによって作製することが可能である。なお、有機EL素子の層構造、又は材料は表示素子として機能するものであれば特に限定されるものではない。また、本発明による固体封止方法はいかなる構造の有機EL素子であっても適用可能である。
これを、JIS K7112 B法に準拠し、硬化物の比重(DS)を測定した。また、23±2℃で樹脂組成物の比重(DL)を測定し、次式により硬化収縮率を算出した。測定結果は4回の測定結果の平均値で示す。
硬化収縮率(%)=(DS−DL)/DS×100
○・・・クラックの発生無し
×・・・クラックの発生有り
OXT−221:東亞合成(株)製3−エチル−3{[(3−エチルオキセタン−3−イル)メトキシ]メチル}オキセタン
SEJ−01R:日本化薬(株)製3,4−エポキシシクロヘキセニルメチル−3’,4’−エポキシシクロヘキセンカルボキシレート
GSID 26−1:BASFジャパン(株)製(トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド
SZR−K:堺化学工業(株)製MEK分散酸化ジルコニウム(固形分濃度30% 一次粒径4nm)
OXT−101:東亞合成(株)製3−エチル−3−ヒドロキシメチルオキセタン
Claims (21)
- 分子中に2つ以上のオキセタン環を有する化合物(A)を2種類以上含有するエネルギー線硬化型樹脂組成物。
- エネルギー線硬化型樹脂組成物の反応性基を有さない有機化合物成分において、重量平均分子量10,000g/mol以上の有機化合物成分の含有量が1.5重量%未満であることを特徴とする請求項1に記載のエネルギー線硬化型樹脂組成物。
- 分子中に2つ以上のオキセタン環を有する化合物(A)が少なくとも下記一般式(1)または下記一般式(2)で表されるオキセタン環を有する化合物である請求項1または請求項2のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
(式中、R1はそれぞれ独立して直接結合または炭素数1〜6の直鎖または分岐鎖状炭化水素基を示し、R2は炭素数1〜15の直鎖若しくは分岐鎖状炭化水素基、または脂環、芳香環、複素環若しくは縮合を含む炭化水素基を示し、R3はそれぞれ独立して炭素数1〜6の直鎖または分岐鎖状炭化水素基を示す。nは平均値で1〜5の整数を表す。)
(式中、R4及びR5はそれぞれ独立して炭素数1〜6の直鎖または分岐鎖状炭化水素基を表し、同一でも異なっていてもよい。) - 分子中に2つ以上のオキセタン環を有する化合物(A)が少なくとも分子中に脂環または芳香環を有する化合物である請求項1〜請求項3の何れか一項に記載のエネルギー線硬化型樹脂組成物
- (1)に記載の分子中に2つ以上のオキセタン環を有する化合物(A)として、上記式(1)記載の化合物及び上記式(2)記載の化合物を含有する請求項1〜請求項4のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
- 分子中に2つ以上のオキセタン環を有する化合物(A)を2種類以上含有し、エネルギー線硬化型樹脂組成物の全有機化合物成分が重量平均分子量10,000g/mol以下で20℃〜80℃で可溶な成分から構成された請求項1〜請求項5のいずれか一項に記載のエネルギー線硬化型樹脂組成物。
- エポキシ化合物(B)を含有する請求項1乃至請求項6の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- エポキシ化合物(B)が脂環式エポキシ化合物である請求項1乃至請求項7の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- エポキシ化合物(B)が分子中に2個以上のエポキシ基を有する化合物である請求項1乃至請求項8に記載のエネルギー線硬化型樹脂組成物。
- エポキシ化合物(B)を20〜70質量部含有する請求項1乃至請求項9に記載のエネルギー線硬化型樹脂組成物。
- 分子中に2つ以上のオキセタン環を有する化合物(A)を30〜90質量部含有する請求項1乃至請求項10の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- 光カチオン重合開始剤(C)を含有する請求項1乃至請求項11の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- 光カチオン重合開始剤(C)がスルホニウム塩、ヨードニウム塩、ホスホニウム塩、アンモニウム塩、アンチモン酸塩から選択される請求項1乃至請求項12の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- 微粒子(D)を含有する請求項1乃至請求項13の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- 微粒子(D)の一次粒径が100nm以下である請求項14に記載のエネルギー線硬化型樹脂組成物。
- E型粘度計で測定した25℃での粘度が10mPa・s以上である請求項1乃至請求項15の何れか一項に記載のエネルギー線硬化型樹脂組成物。
- 請求項1乃至請求項16の何れか一項に記載の封止材用エネルギー線硬化型樹脂組成物。
- 請求項1乃至請求項17の何れか一項に記載の有機ELディスプレイ封止材用エネルギー線硬化型樹脂組成物。
- 請求項1乃至請求項18の何れか一項に記載のエネルギー線硬化型樹脂組成物を硬化せしめて得られる硬化物。
- 厚み100μmでの水蒸気透過率が200g/m2・day/60℃以下である請求項19に記載の硬化物。
- 請求項16または請求項20の何れか一項に記載の硬化物を搭載する有機ELディスプレイ。
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Also Published As
Publication number | Publication date |
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KR101980560B1 (ko) | 2019-05-21 |
WO2014013716A1 (ja) | 2014-01-23 |
TW201410660A (zh) | 2014-03-16 |
TWI603963B (zh) | 2017-11-01 |
KR20150036071A (ko) | 2015-04-07 |
CN104470971B (zh) | 2018-06-22 |
JP5916220B2 (ja) | 2016-05-11 |
CN104470971A (zh) | 2015-03-25 |
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