JP7270635B2 - 有機エレクトロルミネッセンス表示素子用封止剤 - Google Patents
有機エレクトロルミネッセンス表示素子用封止剤 Download PDFInfo
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- JP7270635B2 JP7270635B2 JP2020549233A JP2020549233A JP7270635B2 JP 7270635 B2 JP7270635 B2 JP 7270635B2 JP 2020549233 A JP2020549233 A JP 2020549233A JP 2020549233 A JP2020549233 A JP 2020549233A JP 7270635 B2 JP7270635 B2 JP 7270635B2
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- organic electroluminescence
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- 238000000034 method Methods 0.000 claims description 26
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- 238000004519 manufacturing process Methods 0.000 claims description 16
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 15
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 14
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- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 3
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- MAOCPIDAEMTJLK-UHFFFAOYSA-N tris(4-fluorophenyl)sulfanium Chemical compound C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 MAOCPIDAEMTJLK-UHFFFAOYSA-N 0.000 description 1
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- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/873—Encapsulations
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- 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
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- C—CHEMISTRY; METALLURGY
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/52—Phosphorus bound to oxygen only
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- C—CHEMISTRY; METALLURGY
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- C08K5/54—Silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
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Description
(A)成分は、カチオン重合性を有する化合物であり、カチオン重合性基を有する化合物ということもできる。カチオン重合性基としては、環状エーテル基(例えば、エポキシ基(オキシラン環)、オキセタン基(オキセタン環)等)、カチオン重合性ビニル基等が挙げられる。
(A1)成分は、エポキシ基及び脂環基を有する化合物である。(A1)成分は、エポキシ基を1個有する化合物であってよく、2個以上有する化合物であってもよい。(A1)成分は、エポキシ基を2個以上有することが好ましく、エポキシ基を2個有することがより好ましい。(A1)成分は、芳香環を有しない化合物であってよい。(A1)成分は1種を単独で又は二種以上を組み合わせて用いることができる。
・溶媒(移動相):THF
・脱気装置:ERMA社製ERC-3310
・ポンプ:日本分光社製PU-980
・流速:1.0ml/min
・オートサンプラ:東ソー社製AS-8020
・カラムオーブン:日立製作所製L-5030
・設定温度:40℃
・カラム構成:東ソー社製TSKguardcolumnMP(×L)6.0mmID×4.0cm 2本、及び東ソー社製TSK-GELMULTIPORE HXL-M 7.8mmID×30.0cm 2本、計4本
・検出器:RI 日立製作所製L-3350
・データ処理:SIC480データステーション
(A2)成分は、エポキシ基及び芳香環を有する化合物である。(A2)成分は、エポキシ基を1個有する化合物であってよく、2個以上有する化合物であってもよい。(A2)成分は、エポキシ基を2個以上有することが好ましく、エポキシ基を2個有することがより好ましい。(A2)成分は、脂環基を有しない化合物であってよい。(A2)成分は1種を単独で又は二種以上を組み合わせて用いることができる。
(A)成分は、(A1)成分及び(A2)成分以外の他の化合物((A3)成分)を更に含有していてもよい。(A3)成分は、カチオン重合性基を有する化合物であればよく、例えば、環状エーテル基を有する化合物、カチオン重合性ビニル基を有する化合物等であってよい。(A3)成分は、カチオン重合性基を1個有する化合物であってよく、2個以上有する化合物であってもよい。(A3)成分は、カチオン重合性基を2個以上有することが好ましく、カチオン重合性基を2個有することがより好ましい。(A3)成分は、脂環基及び芳香環を有しない化合物であってよい。(A3)成分は1種を単独で又は二種以上を組み合わせて用いることができる。
(B)成分は、光によって活性化して、(A)成分のカチオン重合を開始させることができる成分であればよい。(B)成分は、一種を単独で又は二種以上を組み合わせて用いることができる。
メチル基、エチル基、プロピル基、ブチル基、ペンチル基、オクチル基、デシル基、ドデシル基、テトラデシル基、ヘキサデシル基、オクダデシル基等の炭素数1~18の直鎖アルキル基;
イソプロピル基、イソブチル基、sec-ブチル基、tert-ブチル基、イソペンチル基、ネオペンチル基、tert-ペンチル基、イソヘキシル基等の炭素数1~18の分岐アルキル基;
シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等の炭素数3~18のシクロアルキル基;
ヒドロキシ基;
メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、sec-ブトキシ基、tert-ブトキシ基、ヘキシルオキシ基、デシルオキシ基、ドデシルオキシ基等の炭素数1~18の直鎖又は分岐のアルコキシ基;
アセチル基、プロピオニル基、ブタノイル基、2-メチルプロピオニル基、ヘプタノイル基、2-メチルブタノイル基、3-メチルブタノイル基、オクタノイル基、デカノイル基、ドデカノイル基、オクタデカノイル基等の炭素数2~18の直鎖又は分岐のアルキルカルボニル基;
ベンゾイル基、ナフトイル基等の炭素数7~11のアリールカルボニル基;
メトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、イソプロポキシカルボニル基、ブトキシカルボニル基、イソブトキシカルボニル基、sec-ブトキシカルボニル基、tert-ブトキシカルボニル基、オクチロキシカルボニル基、テトラデシルオキシカルボニル基、オクタデシロキシカルボニル基等の炭素数2~19の直鎖又は分岐のアルコキシカルボニル基;
フェノキシカルボニル基、ナフトキシカルボニル基等の炭素数7~11のアリールオキシカルボニル基;
フェニルチオカルボニル基、ナフトキシチオカルボニル基等の炭素数7~11のアリールチオカルボニル基;
アセトキシ基、エチルカルボニルオキシ基、プロピルカルボニルオキシ基、イソプロピルカルボニルオキシ基、ブチルカルボニルオキシ基、イソブチルカルボニルオキシ基、sec-ブチルカルボニルオキシ基、tert-ブチルカルボニルオキシ基、オクチルカルボニルオキシ基、テトラデシルカルボニルオキシ基、オクタデシルカルボニルオキシ基等の炭素数2~19の直鎖又は分岐のアシロキシ基;
フェニルチオ基、2-メチルフェニルチオ基、3-メチルフェニルチオ基、4-メチルフェニルチオ基、2-クロロフェニルチオ基、3-クロロフェニルチオ基、4-クロロフェニルチオ基、2-ブロモフェニルチオ基、3-ブロモフェニルチオ基、4-ブロモフェニルチオ基、2-フルオロフェニルチオ基、3-フルオロフェニルチオ基、4-フルオロフェニルチオ基、2-ヒドロキシフェニルチオ基、4-ヒドロキシフェニルチオ基、2-メトキシフェニルチオ基、4-メトキシフェニルチオ基、1-ナフチルチオ基、2-ナフチルチオ基、4-[4-(フェニルチオ)ベンゾイル]フェニルチオ基、4-[4-(フェニルチオ)フェノキシ]フェニルチオ基、4-[4-(フェニルチオ)フェニル]フェニルチオ基、4-(フェニルチオ)フェニルチオ基、4-ベンゾイルフェニルチオ基、4-ベンゾイル-2-クロロフェニルチオ基、4-ベンゾイル-3-クロロフェニルチオ基、4-ベンゾイル-3-メチルチオフェニルチオ基、4-ベンゾイル-2-メチルチオフェニルチオ基、4-(4-メチルチオベンゾイル)フェニルチオ基、4-(2-メチルチオベンゾイル)フェニルチオ基、4-(p-メチルベンゾイル)フェニルチオ基、4-(p-エチルベンゾイル)フェニルチオ4-(p-イソプロピルベンゾイル)フェニルチオ基、4-(p-tert-ブチルベンゾイル)フェニルチオ基等の炭素数6~20のアリールチオ基;
メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、イソブチルチオ基、sec-ブチルチオ基、tert-ブチルチオ基、ペンチルチオ基、イソペンチルチオ基、ネオペンチルチオ基、tert-ペンチルチオ基、オクチルチオ基、デシルチオ基、ドデシルチオ基等の炭素数1~18の直鎖又は分岐のアルキルチオ基;
フェニル基、トリル基、ジメチルフェニル基、ナフチル基等の炭素数6~10のアリール基;
チエニル基、フラニル基、ピラニル基、ピロリル基、オキサゾリル基、チアゾリル基、ピリジル基、ピリミジル基、ピラジニル基、インドリル基、ベンゾフラニル基、ベンゾチエニル基、キノリル基、イソキノリル基、キノキサリニル基、キナゾリニル基、カルバゾリル基、アクリジニル基、フェノチアジニル基、フェナジニル基、キサンテニル基、チアントレニル基、フェノキサジニル基、フェノキサチイニル基、クロマニル基、イソクロマニル基、ジベンゾチエニル基、キサントニル基、チオキサントニル基、ジベンゾフラニル等の炭素数4~20の複素環基;
フェノキシ基、ナフチルオキシ基等の炭素数6~10のアリールオキシ基;
メチルスルフィニル基、エチルスルフィニル基、プロピルスルフィニル基、イソプロピルスルフィニル基、ブチルスルフィニル基、イソブチルスルフィニル基、sec-ブチルスルフィニル基、tert-ブチルスルフィニル基、ペンチルスルフィニル基、イソペンチルスルフィニル基、ネオペンチルスルフィニル基、tert-ペンチルスルフィニル基、オクチルスルフィニル基等の炭素数1~18の直鎖又は分岐のアルキルスルフィニル基;
フェニルスルフィニル基、トリルスルフィニル基、ナフチルスルフィニル基等の炭素数6~10のアリールスルフィニル基;
メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、イソプロピルスルホニル基、ブチルスルホニル基、イソブチルスルホニル基、sec-ブチルスルホニル基、tert-ブチルスルホニル基、ペンチルスルホニル基、イソペンチルスルホニル基、ネオペンチルスルホニル基、tert-ペンチルスルホニル基、オクチルスルホニル基等の炭素数1~18の直鎖又は分岐のアルキルスルホニル基;
フェニルスルホニル基、トリルスルホニル基(トシル基)、ナフチルスルホニル基等の炭素数の6~10のアリールスルホニル基;
下記式(B-1-2)で表されるアルキレンオキシ基;
無置換のアミノ基、並びに、炭素数1~5のアルキル及び/又は炭素数6~10のアリールでモノ置換若しくはジ置換されているアミノ基;
シアノ基;
ニトロ基;
フッ素、塩素、臭素、ヨウ素等のハロゲン基等が挙げられる。
ジフェニルフェナシルスルホニウム、ジフェニル4-ニトロフェナシルスルホニウム、ジフェニルベンジルスルホニウム、ジフェニルメチルスルホニウム等のジアリールスルホニウム;
フェニルメチルベンジルスルホニウム、4-ヒドロキシフェニルメチルベンジルスルホニウム、4-メトキシフェニルメチルベンジルスルホニウム、4-アセトカルボニルオキシフェニルメチルベンジルスルホニウム、2-ナフチルメチルベンジルスルホニウム、2-ナフチルメチル(1-エトキシカルボニル)エチルスルホニウム、フェニルメチルフェナシルスルホニウム、4-ヒドロキシフェニルメチルフェナシルスルホニウム、4-メトキシフェニルメチルフェナシルスルホニウム、4-アセトカルボニルオキシフェニルメチルフェナシルスルホニウム、2-ナフチルメチルフェナシルスルホニウム、2-ナフチルオクタデシルフェナシルスルホニウム、9-アントラセニルメチルフェナシルスルホニウム等のモノアリールスルホニウム;
ジメチルフェナシルスルホニウム、フェナシルテトラヒドロチオフェニウム、ジメチルベンジルスルホニウム、ベンジルテトラヒドロチオフェニウム、オクタデシルメチルフェナシルスルホニウム等のトリアルキルスルホニウム等が挙げられる。
封止剤は、(X)成分として、リン酸系硬化遅延剤((C)成分)、エーテル系硬化遅延剤((D)成分)、金属錯体系硬化遅延剤((E)成分)及びニトロキシラジカル系硬化遅延剤((F)成分)からなる群より選択される二種以上を含む。
リン酸系硬化遅延剤は、リン酸エステル((C1)成分)及び亜リン酸エステル((C2)成分)からなる群より選択される硬化遅延剤である。(C)成分は一種を単独で又は二種以上を組み合わせて用いることができる。
(D)成分は、エーテル結合を有する硬化遅延剤である。(D)成分は、一種を単独で又は二種以上を組み合わせて用いることができる。
(E)成分は、硬化遅延剤として機能する金属錯体であればよい。(E)成分としては、例えば、金属アセチルアセトナート等が挙げられる。(E)成分は、一種を単独で又は二種以上を組み合わせて用いることができる。
(F)成分は、ニトロキサイド基を有する硬化遅延剤である。(F)成分は、一種を単独で又は二種以上を組み合わせて用いることができる。
4-アミノ-TEMPO、2,2,5,5-テトラメチル-1-ピロリジニルオキシ(以下、PROXYLと表す)又はその誘導体である3-カルボキシル-PROXYL、3-カルバモイル-PROXYL、2,2-ジメチル-4,5-シクロヘキシル-PROXYL、3-オキソ-PROXYL、3-ヒドロキシルイミン-PROXYL、3-アミノメチル-PROXYL、3-メトキシ-PROXYL、3-t-ブチル-PROXYL、3-マレイミド-PROXYL、3,4-ジ―t―ブチル-PROXYL、3-カルボキシリック-2,2,5,5-テトラメチル-1-ピロリジニルオキシ等;
ジアルキルニトロキシサイドラジカル又はその誘導体であるジフェニルニトロキサイド、ジ-t-ブチルニトロキサイド、t-ブチル-t-アミルニトロキサイド等;
4、4-ジメチル-1-オキサゾリジニルオキシ(DOXYL)又はその誘導体である2-ジ-t-ブチル-DOXYL、5-デカン-DOXYL、2-シクロヘキサン-DOXYL等;などが挙げられる。
<封止剤の調製>
表1~4に示す各成分を、表1~4に記載の組成割合(質量部)で混合し、実施例及び比較例の封止剤を調製した。得られた封止剤について、以下に示す評価方法で封止剤の粘度変化率、弾性率変化率及びアウトガス量を評価した。また、得られた封止剤を、以下に示す光硬化条件で硬化して硬化体を形成し、以下に示す評価方法で硬化体の透湿度及び引張剪断接着強さを評価した。
(a1-1)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(ダイセル化学社製「セロキサイド2021P」)
(a1-2)水添ビスフェノールA型エポキシ樹脂(分子量380~430、三菱化学社製「YX8000」)
(a1-3)3,4-エポキシシクロヘキシルメチルメタアクリレート(ダイセル社製「サイクロマーM100」)
(a2-1)ビスフェノールA型エポキシ樹脂(分子量360~390、三菱化学社製「jER828」)
(a2-2)ビスフェノールF型エポキシ樹脂(分子量320~340、三菱化学社製「jER806」)
(a2-3)ビスフェノールF型エポキシ樹脂(分子量360~380、三井化学社製「YL983U」)
(a2-4)ビスフェノールF型エポキシ樹脂(分子量340~380、ADEKA社製「KRM-2490」)
(a3-1)トリプロピレングリコールジグリシジルエーテル(共栄社化学社製「エポライト200P」)
(a3-2)ジ(1-エチル-(3-オキセタニル))メチルエーテル(東亞合成社製「アロンオキセタンOXT-221」)
(a3-3)シクロヘキサンジメタノールジビニルエーテル(日本カーバイド社製「CHDVE」)
(b-1)トリアリールスルホニウム塩ヘキサフルオロアンチモネート(ADEKA社製「アデカオプトマーSP-170」、アニオン種はヘキサフルオロアンチモネート)
(b-2)トリアリールスルホニウム塩(ジフェニル4-チオフェノキシフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、サンアプロ社製「CPI-200K」、アニオン種はリン化合物)
(c1-1)トリス(2-エチルヘキシル)ホスフェート(大八化学工業社製「TOP」)
(c2-1)トリデシルホスファイト(城北化学工業社製「JP-310」)
(c2-2)ビス(デシル)ペンタエリスリトールジホスファイト(城北化学工業社製「JPE-10」)
(c2-3)ビス(2-エチルヘキシル)ハイドロゲンホスファイト(城北化学工業社製「JPE-208」)
(c2-4)ジフェニルモノデシルホスファイト(城北化学工業社製「JPM-311」)
(c4)トリ-n-オクチルホスフィン(城北化学工業社製「TOCP」(登録商標))
(d-1)18-クラウン-6-エーテル(日本曹達社製「クラウンエーテル O-18」)
(d-2)15-クラウン-5-エーテル(日本曹達社製「クラウンエーテル O-15」)
(d-3)ポリオキシエチレン-ジメチルエーテル(日本曹達社製「ユニオックス MM-400」)
(e-1)アルミニウムアセチルアセトナート(川研ファインケミカル社製「アルミキレートA」)
(f-1)2,2,6,6-テトラメチル-1-ピペリジニルオキシ(東京化成社製「TEMPO」)
(g-1)9,10-ジブトキシアントラセン(川崎化成工業社製「ANTHRACURE UVS-1331)
(h-1)γ-グリシドキシプロピルトリメトキシシラン(信越シリコーン社製「KBM-403」)
粘度は、E型粘度計(コーンロータ:1°34’×R24、BROOKFIELD社製「DV3T」)を用い、温度25℃、回転数10rpmの条件下で測定した。
封止剤をガラス基板の上に単位面積当たりの塗布量が10mg/cm2となるように塗布し、その基板に紫外線照射装置(HOYA社製、超高圧水銀ランプ照射装置「UL-750」)を用いて波長365nm、100mW/cm2の紫外線を10秒間照射した。紫外線を照射し終えてから20分後において、粘度を測定した。そして、光照射前の粘度をV0、光照射後の粘度をVνとしたとき、式:Vν/V0にしたがって粘度変化率を求めた。なお、粘度変化率は、遅硬化性が良好な点で、10以下が好ましい。
封止剤をガラス基板の上に単位面積当たりの塗布量が10mg/cm2となるように塗布し、その基板に紫外線照射装置(HOYA社製、超高圧水銀ランプ照射装置「UL-750」)を用いて波長365nm、100mW/cm2の紫外線を10秒間照射した。次いで、80℃雰囲気下で10分間養生した。養生終了後において、回転式レオメーター(アントンパール社製)を用い、平板間隔0.7mm、周波数0.16Hzの条件下で弾性率を測定した。そして、高温養生前の弾性率をY0、高温養生後の弾性率をYνとしたとき、式:Yν/Y0にしたがって弾性率変化率を求めた。なお、弾性率変化率は、熱硬化性が良好な点で、10以上が好ましい。
封止剤をガラス基板の上に単位面積当たりの塗布量が10mg/cm2となるように塗布し、その基板に紫外線照射装置(HOYA社製、超高圧水銀ランプ照射装置「UL-750」)を用いて波長365nm、100mW/cm2の紫外線を10秒間照射した。その後、80℃で60分間加熱し、発生したガス成分を捕集・濃縮して、GC/MS(Agilent Technology社製、「GC/MS 7890B/5977B」)でアウトガス量を測定した。
無電極放電メタルハライドランプ搭載UV硬化装置(フュージョン社製)を用いて、波長365nm、積算光量1,000mJ/cm2の条件にて、封止剤を光硬化させた。次いで、80℃のオーブン中で30分間の加熱処理を実施し、硬化体を作製した。
厚さ0.1mmのシート状の硬化体を、上記硬化条件にて作製した。JIS Z0208「防湿包装材料の透湿度試験方法(カップ法)」に準じ、吸湿剤として塩化カルシウム(無水)を用い、雰囲気温度60℃、相対湿度90%の条件で、硬化体の透湿度を測定した。結果を表5~8に示す。なお、透湿度は120g/(m2・24hr)以下が好ましい。
被着材としてホウ珪酸ガラス試験片(縦25mm×横25mm×厚2.0mm、「テンパックス(登録商標)ガラス」)を用い、接着面積0.5cm2、接着厚み80μmとなるようにして、封止剤を用いて2枚のホウ珪酸ガラス試験片を貼り合わせた。次いで、上記の硬化条件にて封止剤を硬化させ、試験片を作製した。作製した試験片について、引張試験機(インストロン社製)を用いて、温度23℃、相対湿度50%の環境下、引張速度10mm/分で引張剪断接着強さを測定した。
封止剤の初期粘度(V0、封止剤調製直後の粘度)を測定した後、容器に入れて蓋をした状態(密閉系)で約40℃の高温環境下における促進試験で4週間後の組成物の粘度(V4)を測定した。そして、式:V4/V0にしたがって粘度変化率を求めた。なお、粘度変化率は、保存安定性が良好な点で、1.5以下が好ましい。
まず、有機EL表示素子基板を作製した。ITO電極付きガラス基板をアセトン、イソプロパノールそれぞれを用いて洗浄した。その後、真空蒸着法にて以下の化合物を薄膜となるように順次蒸着し、陽極/正孔注入層/正孔輸送層/発光層/電子注入層/陰極の層構成を有する有機EL表示素子基板を得た。各層の構成は以下の通りである。
・陽極:ITO、厚さ250nm
・正孔注入層:銅フタロシアニン、厚さ30nm
・正孔輸送層:N,N’-ジフェニル-N,N’-ジナフチルベンジジン(α-NPD)、厚さ20nm
・発光層:トリス(8-ヒドロキシキノリナト)アルミニウム(金属錯体系材料)、厚さ1000Å
・電子注入層:フッ化リチウム、厚さ1nm
・陰極:アルミニウム、厚さ250nm
作製した直後の有機EL表示素子の発光状態を目視と顕微鏡で観察し、ダークスポットの直径を測定した。また、作製した直後の有機EL表示素子を、85℃、相対湿度85質量%の条件下にて1000時間暴露した後、6Vの電圧を印加した。この有機EL表示素子の発光状態を目視と顕微鏡で観察し、ダークスポットの直径を測定した。なお、ダークスポットの直径は、200μm以下が好ましく、50μm以下がより好ましく、ダークスポットはないことが更に好ましい。
Claims (16)
- エポキシ基を有する脂環式化合物及びエポキシ基を有する芳香族化合物を含有するカチオン重合性化合物と、
光カチオン重合開始剤と、
リン酸系硬化遅延剤と、
エーテル系硬化遅延剤と、
を含み、
前記リン酸系硬化遅延剤が、式(C1-1)で表される化合物、式(C1-2)で表される化合物、式(C1-3)で表される化合物、式(C2-1)で表される化合物、式(C2-2)で表される化合物、式(C2-3)で表される化合物、式(C2-4)で表される化合物、式(C2-5)で表される化合物及び式(C2-6)で表される化合物からなる群より選択される少なくとも一種を含有する、
有機エレクトロルミネッセンス表示素子用封止剤。
[式中、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 及びR 17 はそれぞれ独立にアルキル基を示す。] - 前記エーテル系硬化遅延剤として、環状エーテルを含む、請求項1に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 前記芳香族化合物が、ビスフェノールA型エポキシ樹脂及びビスフェノールF型エポキシ樹脂からなる群から選択される少なくとも一種を含む、請求項1又は2に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 前記光カチオン重合開始剤がオニウム塩化合物を含有する、請求項1~3のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 前記リン酸系硬化遅延剤の含有量が、前記カチオン重合性化合物100質量部に対して0.01~2質量部である、請求項1~4のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 前記エーテル系硬化遅延剤の含有量D1に対する前記リン酸系硬化遅延剤の含有量C1の比(C1/D1)が、0.05~2である、請求項1~5のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 前記光カチオン重合開始剤の含有量が、前記カチオン重合性化合物100質量部に対して0.1~5質量部である、請求項1~6のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 光増感剤を更に含有する、請求項1~7のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- シランカップリング剤を更に含有する、請求項1~8のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤。
- 請求項1~9のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤の硬化体。
- 請求項10に記載の硬化体を含む、有機エレクトロルミネッセンス表示素子用封止材。
- 有機エレクトロルミネッセンス表示素子と、
請求項11に記載の有機エレクトロルミネッセンス表示素子用封止材と、を含む、有機エレクトロルミネッセンス表示装置。 - 第一の部材に、請求項1~9のいずれか一項に記載の有機エレクトロルミネッセンス表示素子用封止剤を付着させる付着工程と、
付着させた前記有機エレクトロルミネッセンス表示素子用封止剤に光を照射する照射工程と、
光照射された前記有機エレクトロルミネッセンス表示素子用封止剤を介して、前記第一の部材と第二の部材とを貼り合わせる貼合工程と、
を備える、有機エレクトロルミネッセンス表示装置の製造方法。 - 前記第一の部材が有機エレクトロルミネッセンス表示素子であり、
前記第二の部材が基板である、請求項13に記載の有機エレクトロルミネッセンス表示装置の製造方法。 - 前記第一の部材が基板であり、
前記第二の部材が有機エレクトロルミネッセンス表示素子である、請求項13に記載の有機エレクトロルミネッセンス表示装置の製造方法。 - 前記基板がカラーフィルターである、請求項14又は15に記載の有機エレクトロルミネッセンス表示装置の製造方法。
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