JP6323171B2 - 有機el素子用水分捕獲体形成組成物、水分捕獲体および有機el素子 - Google Patents
有機el素子用水分捕獲体形成組成物、水分捕獲体および有機el素子 Download PDFInfo
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- JP6323171B2 JP6323171B2 JP2014110475A JP2014110475A JP6323171B2 JP 6323171 B2 JP6323171 B2 JP 6323171B2 JP 2014110475 A JP2014110475 A JP 2014110475A JP 2014110475 A JP2014110475 A JP 2014110475A JP 6323171 B2 JP6323171 B2 JP 6323171B2
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- 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
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Description
(B)酸発生剤および塩基発生剤からなる群より選択される少なくとも1種と
を含む有機EL素子用水分捕獲体形成組成物。
本発明の有機EL素子用水分捕獲体形成組成物は、(A)カルボン酸無水物と、(B)酸発生剤および塩基発生剤からなる群より選択される少なくとも1種とを含有する。また、本発明の有機EL素子用水分捕獲体形成組成物は、(C)硬化性化合物をさらに含有することが好ましい。
本発明の実施形態の水分捕獲体形成組成物は、(A)成分として、カルボン酸無水物を含有する。本実施形態の水分捕獲体形成組成物の(A)カルボン酸無水物としては、例えば、モノカルボン酸の無水物、ジカルボン酸無水物およびテトラカルボン酸二無水物が挙げられる。(A)カルボン酸無水物は、中性条件下においては水との反応性が低く安定であるが、酸または塩基の存在下では加水分解反応を容易に起こす。
モノカルボン酸の無水物としては、トリフルオロ酢酸無水物、安息香酸無水物、イサトイン酸無水物、イソペンタン酸無水物、イソ酪酸無水物、n−吉草酸無水物、クロトン酸無水物などが挙げられる。モノカルボン酸の無水物の炭素数は、加水分解により生成しうるカルボン酸の揮発性の観点から、好ましくは4〜20、より好ましくは4〜14である。
ジカルボン酸無水物としては、下記式(A−1)で表される化合物が挙げられる。
テトラカルボン酸二無水物としては、下記式(A−2)で表される化合物が挙げられる。
本発明の実施形態の水分捕獲体形成組成物の作用効果について、以下に説明する。
本発明の実施形態の水分捕獲体形成組成物は、(B)成分として、(B)酸発生剤および塩基発生剤からなる群より選択される少なくとも1種を含有する。以下、本実施形態の水分捕獲体形成組成物の(B)成分である酸発生剤および塩基発生剤をそれぞれ「酸発生剤(B1)」および「塩基発生剤(B2)」とも言う。
感放射線性酸発生剤および感放射線塩基発生剤は、これらに放射線を照射することにより、それぞれ酸性活性物質および塩基性活性物質を放出することができる化合物と定義することができる。
酸発生剤(B1)としては、例えば、ヨードニウム塩、スルホニウム塩、ホスホニウム塩等の光または熱カチオン硬化触媒、イミダゾール類、酸無水物等のアニオン硬化触媒を使用することができる。これらの中ではカチオン硬化触媒が好ましく、光カチオン硬化触媒がより好ましい。硬化速度が速いこと、また光を当てない限り重合反応が開始しないので、保存安定性が良好なためである。
塩基発生剤(B2)としては、感放射線性塩基発生剤が好ましく、感放射線性塩基発生剤としては、放射線の照射によりアミン等の塩基を発生する化合物である限り、特に限定されない。感放射線性塩基発生剤としては、例えば、コバルト等の遷移金属錯体、オルトニトロベンジルカルバメート類、アシルオキシイミノ類、α,α−ジメチル−3,5−ジメトキシベンジルカルバメート類が挙げられる。
本発明の実施形態の水分捕獲体形成組成物は、さらに(C)成分として、(C)硬化性化合物を含有することが好ましい。本発明の実施形態の水分捕獲体形成組成物が(C)硬化性化合物を含有することで架橋反応性を高めることができる。そして、この水分捕獲体形成組成物から形成される本発明の実施形態の水分捕獲体の膜強度および基板との密着性を向上させることができる。
単官能エポキシ化合物として、
グリシジルエーテル、ブチルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、ステアリルグリシジルエーテル、ラウリルグリシジルエーテル、ブトキシポリエチレングリコールグリシジルエーテル、フェノールポリエチレングリコールグリシジルエーテル、アリルグリシジルエーテル、フェニルグリシジルエーテル、p−メチルフェニルグリシジルエーテル、p−エチルフェニルグリシジルエーテル、p−sec−ブチルフェニルグリシジルエーテル、p−tert−ブチルフェニルグリシジル等、
多官能エポキシ化合物として、
ビスフェノールAジグリシジルエーテル、ビスフェノールFジグリシジルエーテル、ビスフェノールSジグリシジルエーテル、水添ビスフェノールAジグリシジルエーテル、水添ビスフェノールFジグリシジルエーテル、水添ビスフェノールADジグリシジルエーテル等のビスフェノールのポリグリシジルエーテル類;
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等の多価アルコールのポリグリシジルエーテル類;
エチレングリコール、プロピレングリコール、グリセリン等の脂肪族多価アルコールに1種または2種以上のアルキレンオキサイドを付加することにより得られるポリエーテルポリオールの脂肪族ポリグリシジルエーテル類;
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−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)、ラクトン変性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等の3,4−エポキシシクロヘキシル基を有する化合物等が挙げられる。
単官能オキセタン化合物として、
3−エチル−3−ヒドロキシメチルオキセタン(オキセタンアルコール)、2−エチルヘキシルオキセタン、3−エチル−3−(2−エチルヘキシロキシメチル)オキセタン、3−エチル−3−(ドデシロキシメチル)オキセタン、3−エチル−3−(オクタデシロキシメチル)オキセタン、3−エチル−3−(フェノキシメチル)オキセタン、3−エチル−3−ヒドロキシメチルオキセタン等、
多官能オキセタン化合物として、
キシリレンビスオキセタン、1−ブトキシ−2,2−ビス〔(3−エチルオキセタン−3−イル)メトキシメチル〕ブタン、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、1,1,1−トリス〔(3−エチルオキセタン−3−イル)メトキシメチル〕プロパン等が挙げられる。
本発明の実施形態の水分捕獲体形成組成物は、本発明の効果を損なわない範囲で、必要に応じて、(D)ラジカル重合開始剤、(E)微粒子および添加剤から選択される少なくとも1種の他の成分を含有してもよい。その他の任意成分は、1種単独で使用してもよく、2種以上を併用してもよい。尚、(D)ラジカル重合開始剤および(E)微粒子をそれぞれ、(D)成分および(E)成分ということがある。
本発明の実施形態の水分捕獲体形成組成物は、さらに(D)ラジカル重合開始剤を含有することができる。(D)ラジカル重合開始剤としては、活性光線、熱、酸または塩基によりラジカルを発生する化合物を意味し、例えば、熱ラジカル重合開始剤および光ラジカル重合開始剤等が挙げられる。(D)ラジカル重合開始剤を含有することで、例えば、上述の化学反応式に示す加水分解反応によって形成されたアルコール化合物および金属アルコキシド化合物が、前記組成物から形成される水分捕獲体中に効率良く固定化され、留まることが容易となる。
本発明の実施形態の水分捕獲体形成組成物は、さらに(E)微粒子を含有することができる。(E)微粒子は、本実施形態の水分捕獲体形成組成物を用いて形成される本発明の実施形態の水分捕獲体に光散乱性を付与するための成分である。したがって、(E)微粒子は、光散乱粒子であることが好ましい。本実施形態の水分捕獲体形成組成物がこのような微粒子を含有することで、耐熱性向上および光取り出し効率を向上させることができる。
本発明の実施形態の水分捕獲体形成組成物は、必要に応じて添加剤を含有してもよい。具体的には、増感剤、硬化促進剤、光増感剤、分散助剤、充填剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤、熱重合禁止剤、消泡剤、界面活性剤等が例示される。
本発明の有機EL素子用水分捕獲体形成組成物は、(A)カルボン酸無水物および(B)酸発生剤および塩基発生剤からなる群より選択される少なくとも1種を混合し、必要に応じて(C)硬化性化合物、(D)ラジカル重合開始剤、(E)微粒子および安定剤等を所定の割合で混合することにより調製することができる。
本発明の実施形態の水分捕獲体は、上述した本発明の実施形態の有機EL素子用水分捕獲体形成組成物から形成される。
本発明の実施形態の水分捕獲体形成組成物は、水分捕獲体を形成し、水分が特性を低下させる懸念のある本発明の実施形態の電子デバイスの構成に用いられる。本発明の実施形態の電子デバイスとしては、水分が特性を低下させる懸念のある電子デバイスであれば、いかなる電子デバイスであってもよい。そのような電子デバイスとしては、例えば、有機EL素子および液晶表示素子が挙げられる。有機EL素子である場合、例えば、高信頼の有機EL照明装置や有機EL表示素子を構成することができる。
アルカリ金属(例えばLi、Na、およびK等)およびそのフッ化物;
アルカリ土類金属(例えばMg、およびCa等)およびそのフッ化物;
金、銀、鉛、アルミニウム、ナトリウム−カリウム合金、およびこれらを含む混合金属;
リチウム−アルミニウム合金およびこれを含む混合金属;
LiF/Al合金およびこれを含む混合金属;
マグネシウム−銀合金およびこれを含む混合金属;
インジウム、およびイッテリビウム等の希土類金属等が挙げられる。
好ましくは仕事関数が4eV以下の材料であり、より好ましくはアルミニウム、リチウム−アルミニウム合金およびそれらの混合金属、マグネシウム−銀合金およびその混合金属等を挙げることができる。
および、
ポリチオフェン、ポリフェニレン、およびポリフェニレンビニレン等のポリマー化合物等が挙げられる。
酸化スズ、酸化亜鉛、酸化インジウム、および酸化インジウムスズ(ITO)等の導電性金属酸化物;
金、銀、クロム、およびニッケル等の金属;
ヨウ化銅および硫化銅などの他の無機導電性物質;
ポリアニリン、ポリチオフェン、PEDOT/PSS、およびポリピロール等の有機導電性物質;
およびこれらの混合物または積層物等が挙げられる。
アルカリ金属(例えばLi、Na、およびK等)およびそのフッ化物;
アルカリ土類金属(例えばMg、およびCa等)およびそのフッ化物;
金、銀、鉛、アルミニウム、ナトリウム−カリウム合金、およびこれらを含む混合金属;
リチウム−アルミニウム合金およびこれを含む混合金属;
LiF/Al合金およびこれを含む混合金属;
マグネシウム−銀合金およびこれを含む混合金属;
インジウム、およびイッテリビウム等の希土類金属等が挙げられる。
本実施例の各水分捕獲体形成組成物の調製に用いた(A)成分((A)カルボン酸無水物および従来の水分捕獲剤)、(B)成分(酸発生剤または塩基発生剤)、(C)成分(硬化性化合物)、(D)成分((D)ラジカル重合開始剤)および(E)成分((E)微粒子を以下に示す。尚、(A)成分のAS−1〜AS−6については、それぞれの融点(℃)も併せて示す。
AS−1:4−メチルヘキサヒドロフタル酸無水物(新日本理化(株)製)/−15℃
AS−2:4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(和光純薬工業(株)製)/244℃
AS−3:グリセリンビス アンヒドロトリメリテート モノアセテート(新日本理化(株)製)/65℃−85℃
AS−4:5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物(東京化成工業(株)製)/172℃
AS−5:3,3’,4,4’−ジフェニルスルホンテトラカルボン酸2無水物(新日本理化(株)製)/287℃
AS−6:テトラプロぺニル無水コハク酸(新日本理化(株)製)/−5℃
AS−7:アルミニウムトリイソプロポキシド(Al(i−PrO)3)(東京化成工業(株)製)
AS−8:酸化カルシウム(東京化成工業(株)製)
B−1:CPI−200K(サンアプロ社製)
B−2:サンエイド(登録商標)SI−80L(三新化学工業製)
C−1:エピコート(登録商標)828(三菱化学製)
C−2:デナコール(登録商標)EX−212(ナガセ製)
C−3:NKエステル9PG(新中村化学製)
D−1:ルシリン(登録商標)TPO(BASF社製)
D−2:V−601(和光純薬社製)
E−1:日産化学社製ナノユース(登録商標)OZ−S30K−AC(酸化ジルコニウムの一次粒径20nm、動的光散乱による平均粒径80nm、固形分濃度20質量%)、
E−2:シーアイ化成社製RTTCHN15WT%−E06(酸化チタニウムの一次粒径25nm、動的光散乱による平均粒径100nm、固形分濃度15質量%)
大気環境下で、(C)成分である(C−1)80質量部に、水分捕獲剤である(A)成分(AS−1)20質量部を添加して均一な溶液とした後、この溶液に(B)成分である(B−1)1質量部を加えて水分捕獲体形成組成物(JS−1)を調製した。使用した各成分および配合量は、後述する他の実施例とともに、表1にまとめて示す。
(水分捕獲体形成組成物(JS−2)〜(JS−17)の調製)
下記表1に示す種類および配合量の各成分を用いた以外は、実施例1と同様に操作し、各水分捕獲体形成組成物を調製した。
縦横25mm、厚さ0.7mmのガラス板に膜厚15nmのITO膜が幅2mmのパターンで形成されたガラス基板(旭硝子(株)製)上に、正孔注入材料としてポリ(3,4)エチレンジオキシチオフェン/ポリスチレンサルフォネイト(PEDOT/PSS)を含有する正孔注入層形成用塗液を3000rpmで50秒間スピンコートを行い、膜厚50nmの正孔注入層を形成した後、高純度窒素中、200℃で10分間加熱・乾燥を行った。ここで、正孔注入層形成用塗液としては、PEDOT/PSSを純水に固形分0.1質量%で溶解したものを用いた。正孔注入層上に、発光材料ポリフルオレン誘導体の1.0質量%溶液を2000rpmで50秒間スピンコートを行い、膜厚70nmの有機発光層を形成した後、60℃で10分間焼成した。有機発光層上に、10−5Paの圧力条件下、0.1nm/secの蒸着速度でLiFを10nm、0.1nm/secの蒸着速度でCaを20nm積層し、その上に20nm/secの蒸着速度でAlを100nm積層して陰極を形成した。
上記調製した実施例1〜実施例13および比較例1〜4の各水分捕獲体形成組成物の製膜性、各水分捕獲体の耐熱性、ガラス密着性、発光外観および光取出し効率を下記方法に従い評価した。その評価結果を表1に合わせて示す。
上記調製した各水分捕獲体形成組成物を用い、長辺66mm、短辺24mm、厚さ1.1mmのガラス基板に、長辺58mm、短辺13mm、深さ0.3mmの掘込みを設け、この堀込みに水分捕獲体形成組成物200μLを塗布した後、高圧水銀ランプを用いてUV照射(照射エネルギー:1J/cm2)により硬化させて水分捕獲体を形成し、目視により外観観察を行った。このとき、クラック及び凹凸が認められない場合、製膜性は良好「○」と、クラックまたは凹凸の少なくともいずれかが認められた場合、不良「×」と評価した。
サンプル管中に、上記調製した各水分捕獲体形成組成物を適量入れ、上述の[製膜性]の硬化条件と同じ条件で、膜厚2mmの水分捕獲体をサンプル管底部に形成した。次いで、形成した水分捕獲体を大気に暴露して十分吸湿させた後、サンプル管の蓋を閉めてシールし、サンプル管の底部が上(製膜面が上)となるように固定した状態で85℃の環境下に静置した。その後、336時間経過した時点の水分捕獲体の状態を観察した。このとき、水分捕獲体に全く変化が認められなかった場合、耐熱性は極良好「○」と評価し、極軽微な変化のみが認められた場合、良好「△」と評価し、水分捕獲体が下方へ垂れて変形が認められた場合、不良「×」と評価した。
上記調製した各水分捕獲体形成組成物を用い、長辺66mm、短辺24mm、厚さ1.1mmのガラス基板に、上述の[製膜性]の硬化条件と同じ条件で、膜厚2mmの水分捕獲体を形成した。大気中における、上記ガラス基板からの各水分捕獲体の剥離の有無を観察した。このとき、剥離が認められない場合、密着性は良好「○」と、剥離した場合、不良「×」と評価した。
上記[有機EL素子の製造]で得られたそれぞれの有機EL素子について、室温において順方向電流を10mA/cm2通電し、発光外観(ダークスポット、ムラ)を観察した。また、コニカミノルタセンシング(株)社製分光放射輝度計「CS−2000」により正面輝度を測定し、光散乱層を形成していない基板で作製した有機EL素子の正面輝度を基準とし、白色発光素子の正面輝度の向上率を算出した。
・発光外観(ダークスポット、ムラ)
ダークスポット、ムラが観察されない:良(○)、
ダークスポット、ムラが観察される:不可(×)
・光取出し効率
正面輝度向上率1.2倍以上:優(◎)、
正面輝度向上率1.0倍以上〜1.2倍未満:良(○)、
正面輝度向上率1.0倍未満:不良(×)
20 構造体
22 基板
24 封止用基板
26 シール材
30,130 水分捕獲体
40 ガスバリヤフィルム
100,200,300,400,500 有機EL素子
Claims (1)
- (A)カルボン酸無水物と、
(B)酸発生剤および塩基発生剤からなる群より選択される少なくとも1種と
を含む有機EL素子用水分捕獲体形成組成物であって、
該(A)カルボン酸無水物が、テトラカルボン酸二無水物から選ばれる少なくとも1種で
あることを特徴とする有機EL素子用水分捕獲体形成組成物。
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