JP5213303B2 - 光硬化性吸湿性組成物及び有機el素子 - Google Patents
光硬化性吸湿性組成物及び有機el素子 Download PDFInfo
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- JP5213303B2 JP5213303B2 JP2006008628A JP2006008628A JP5213303B2 JP 5213303 B2 JP5213303 B2 JP 5213303B2 JP 2006008628 A JP2006008628 A JP 2006008628A JP 2006008628 A JP2006008628 A JP 2006008628A JP 5213303 B2 JP5213303 B2 JP 5213303B2
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- 239000000203 mixture Substances 0.000 title claims description 36
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- 150000002902 organometallic compounds Chemical class 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- -1 cyclic aluminum compound Chemical class 0.000 description 44
- 239000010408 film Substances 0.000 description 36
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 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 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- VEQCTDMBEVLHOF-UHFFFAOYSA-N 1-(2-benzoylphenyl)prop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 VEQCTDMBEVLHOF-UHFFFAOYSA-N 0.000 description 1
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 1
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- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/287—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polypropylene oxide in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/057—Metal alcoholates
Description
(a)湿気反応性有機金属化合物、
(b)(メタ)アクリレート、
(c)カルボキシル基含有重合性モノマー、及び
(d)光重合開始剤
を含み、湿気反応性有機金属化合物(a)の割合が全組成物中5〜70wt%であり、カルボキシル基含有重合性モノマー(c)の割合が、湿気反応性有機金属化合物(a)に対して0.1〜50モル%である、光硬化性吸湿性組成物が提供される。
M(OR)n
で表される金属アルコキシドであり、式中MはAl、B、Ti、又はZrであり、Rはアルキル基、アルケニル基、アリール基、シクロアルキル基、複素環基、又はアシル基であり、nはMの原子価である。このような金属アルコキシドは、通常多量体として存在する。
M(OR)n+xH2O → M(OH)x(OR)n-x+xROH
片末端に水酸基を有するポリオキシエチレンモノメチルエーテル(Mw350、Sigma Aldrich社製)30gを、窒素置換した100mLのシュレンク管内に入れ、水冷し、28.6gのエチルアルミニウムのヘキサン溶液を徐々に加えた。エタンガスの発生が終了後、室温に戻し、さらに24時間攪拌を続けた。溶媒を減圧留去し、湿気反応性有機金属化合物1(トリス(ポリオキシエチレンオキシ)アルミニウム)を得た。また、上記ポリオキシエチレンモノメチルエーテルに代えてトリプロピレングリコールエーテル(Mw287、Sigma Aldrich社製)、ポリジメチルシロキサンプロポキシエタノール(チッソ社製、SILAPLANE FM0411)、オクタドデカノール(花王社製)、及び1−(ヒドロキシエチル)−2−ピロリドン(東京化成社製)を用いて湿気反応性有機金属化合物2(トリス(ポリオキシエチレンオキシ)アルミニウム)、3(トリス(ポリジメチルシロキサンプロポキシエトキシ)アルミニウム)、4(トリス(オクタドデシルオキシ)アルミニウム)、及び5(トリス(2−ピロリドン−1−エチル−2−オキシ)アルミニウム)を得た。
光硬化性吸湿性組成物の調製
(メタ)アクリレートとしてポリオキシエチレンモノメチルエーテルアクリレート(新中村化学社製、AM90G)8.0g及びポリオキシエチレンジアクリレート(新中村化学社製、A−600)2.0gを用い、これらを窒素置換した30mLの管に入れた。次いで上記で調製した湿気反応性有機金属化合物1(10g)を徐々に加えた攪拌した。さらに光開始剤(チバガイギー社製、ダロキュア1173)0.1g及びカルボキシル基含有重合性モノマーとしてアクリル酸(和光純薬社製)0.1gを加え均一になるまで攪拌し、光硬化性吸湿性組成物A−1を得た。
上記光硬化性吸湿性組成物1をポリエチレンテレフタレート(PET)フィルム(ルミラーT−60、厚さ50μm、東レ社製)及びシリコーン剥離処理PETフィルム(SP−PET−01、50BU、厚さ50μm、パナック社製)でラミネートし、ナイフギャップを通過させてフィルムとした。このフィルムに紫外線照射装置(ウシオ電機社製、UVC183)を用いて1000mJ/cm2の紫外線を照射し、総厚み150μmの吸湿性フィルムを得た。
表1に示す材料を用いて実施例1と同様にして光硬化性吸湿性組成物A−2〜A−8を調製し、この組成物を用いて吸湿性フィルムを作製した。
モノアクリレートとジアクリレートの比率を変えた以外は実施例1と同様に行った。
アクリル酸を加えないことを除き、実施例4と同様に行った。
吸湿性化合物として酸化カルシウム粉末を用いた。
モノアクリレート1:ポリオキシエチレンモノメチルエーテルアクリレート(新中村化学製AM90G)
モノアクリレート2:ポリオキシプロピレンアクリレート(日本油脂社製AP800)
モノアクリレート3:イソボルニルアクリレート(共栄社油脂社製IBX-A)
モノアクリレート4:フェノキシエチルアクリレート(大阪有機化学工業社製ビスコート#192)
ジアクリレート1:ポリオキシエチレンジアクリレート(新中村化学社製A600)
ジアクリレート2:ビス−A・30EOジメタクリレート(日本油脂社製BLEMMER PDBE-1300)
ジアクリレート3:ポリ(EO)ジアクリレート(日本油脂社製BLEMMER DA-800AU)
ジアクリレート4:ポリオキシプロピレンジアクリレート(新中村化学社製APG700)
ジアクリレート5:ポリ(PO)ジアクリレート(日本油脂社製BLEMMER DA-800)
ジアクリレート6:シリコーンジメタクリレート(チッソ社製SILAPLANE FM7725)
ジアクリレート7:水素化ポリブタジエンジアクリレート(日本曹達社製TEAL1000)
光重合開始剤1:チバガイギー社製、Darocure 1173
光重合開始剤2:チバガイギー社製、Irgacure 651
得られた吸湿性フィルムについて、吸湿性、透過率、及び可撓性を以下のようにして測定した。
吸湿性フィルムを30mm×40mm角に切り出し、シリコーン剥離処理PETフィルムを剥がし、直ちに容積400mLの温湿度計付きステンレス容器に入れ金属製の蓋を閉めた。このステンレス容器内の相対湿度が10%低下するまでの時間を測定した。測定結果を表2に示す。
透過率の測定は日立製Spectrophotometer U-4100を用いて行った。測定用のサンプルは上記の方法で作製した50μmのPET付きフィルムを相対湿度50%の空気中気温25℃で3日間放置し、十分吸湿したものを用いた。解析では、PETフィルムをベースラインとした。波長域400nm〜800nmの範囲の最低透過率を表2に示す。
上記で用いたフィルムを鉄棒(R=10mm)に沿って曲げ、目視により観察した。10回繰り返したが、実施例1のフィルムにおいては表面にクラックの発生はまったくみられなかった。
2 封止キャップ
3 電極
4 有機機能層
5 電極
6 吸湿性フィルム
7 封止接着剤
Claims (2)
- (a)湿気反応性有機金属化合物、
(b)(メタ)アクリレート、
(c)カルボキシル基含有重合性モノマー、及び
(d)光重合開始剤
を含み、湿気反応性有機金属化合物(a)の割合が全組成物中5〜70wt%であり、カルボキシル基含有重合性モノマー(c)の割合が、湿気反応性有機金属化合物(a)に対して0.1〜50モル%であり、前記湿気反応性有機金属化合物が下式
M(OR) n
で表される金属アルコキシドであり、式中MはAl、B、Ti、又はZrであり、Rはアルキル基、アルケニル基、アリール基、シクロアルキル基、複素環基、又はアシル基であり、nはMの原子価であり、前記(メタ)アクリレートがモノ(メタ)アクリレートもしくは多官能(メタ)アクリレート、又はこの両者を含み、前記多官能(メタ)アクリレートを含む場合、この多官能(メタ)アクリレートの割合が、この多官能(メタ)アクリレートの(メタ)アクリロイル基が全組成物100gに対して0.05モル以下となるような量である、光硬化性吸湿性組成物。 - 有機材料からなる有機発光材料層が互いに対向する一対の電極間に挟持されてなる積層体と、この積層体を外気から遮断する構造体と、この構造体内に配置された乾燥手段とを有する有機EL素子であって、前記乾燥手段が請求項1に記載の光硬化性吸湿性組成物より形成された吸湿性フィルムを含むことを特徴とする有機EL素子。
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PCT/US2007/000861 WO2007084386A1 (en) | 2006-01-17 | 2007-01-12 | Photocurable hygroscopic composition and organic el device |
KR1020087019934A KR101366884B1 (ko) | 2006-01-17 | 2007-01-12 | 광경화성 흡습성 조성물 및 유기 전계발광 소자 |
CNA2007800031510A CN101374896A (zh) | 2006-01-17 | 2007-01-12 | 光致固化型吸湿性组合物以及有机电致发光器件 |
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- 2007-01-12 WO PCT/US2007/000861 patent/WO2007084386A1/en active Application Filing
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US10556974B2 (en) | 2014-08-05 | 2020-02-11 | Furukawa Electric Co., Ltd. | Curable and hygroscopic resin composition for sealing electronic devices, sealing resin, and electronic device |
US10079360B2 (en) | 2014-12-08 | 2018-09-18 | Furukawa Electric Co., Ltd. | Resin composition for sealing electronic devices, and electronic device |
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KR20080091368A (ko) | 2008-10-10 |
US20090045729A1 (en) | 2009-02-19 |
JP2007191511A (ja) | 2007-08-02 |
WO2007084386A1 (en) | 2007-07-26 |
US7923480B2 (en) | 2011-04-12 |
CN101374896A (zh) | 2009-02-25 |
KR101366884B1 (ko) | 2014-02-24 |
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