JP6768240B2 - コーティング組成物、これを用いた有機電界発光素子の製造方法およびこれにより製造された有機電界発光素子 - Google Patents
コーティング組成物、これを用いた有機電界発光素子の製造方法およびこれにより製造された有機電界発光素子 Download PDFInfo
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- JP6768240B2 JP6768240B2 JP2019532911A JP2019532911A JP6768240B2 JP 6768240 B2 JP6768240 B2 JP 6768240B2 JP 2019532911 A JP2019532911 A JP 2019532911A JP 2019532911 A JP2019532911 A JP 2019532911A JP 6768240 B2 JP6768240 B2 JP 6768240B2
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- ether
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- 125000002524 organometallic group Chemical group 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 21
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- 125000004185 ester group Chemical group 0.000 claims description 2
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
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- 230000032258 transport Effects 0.000 description 32
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- -1 benzodiathiazine Chemical compound 0.000 description 16
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
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- 239000011572 manganese Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000009718 spray deposition Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08F16/00—Homopolymers and 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/30—Monomers containing sulfur
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
- C08F28/00—Homopolymers and 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 bond to sulfur or by a heterocyclic ring containing sulfur
- C08F28/02—Homopolymers and 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 bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions based on homopolymers or 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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/10—Homopolymers or copolymers of unsaturated ethers
-
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Description
遷移金属の有機金属錯体;
下記化学式1の単位を含む高分子;および
有機溶媒を含む有機電界発光素子の正孔注入または輸送層コーティング組成物を提供する:
Aは、置換もしくは非置換のアルキレン基であり、アルキレン鎖のCのうち少なくとも1つの代わりに、芳香族炭化水素環、ヘテロ環、O、S、C(=O)、S(=O)、またはS(=O)2が位置してもよいし、
X1は、OまたはSであり、X2は、CR5R6、O、またはSであり、nは、1〜10の整数であり、pは、1〜10の整数であり、mは、0〜10の整数であり、
Yは、SO3H、SO3Li、SO3Na、SO3K、SO3Rb、またはSO3Csであり、
R1〜R6は、それぞれ独立に、水素、フッ素、アルキル基、またはフルオロアルキル基であり、ただし、R1およびR2の少なくとも1つは、フッ素である。
基板を準備するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に、前述した実施態様に係るコーティング組成物を用いて正孔注入または輸送層をコーティング方法で形成するステップをさらに含む有機電界発光素子の製造方法を提供する。
第1電極と、第2電極と、前記第1電極と前記第2電極との間に備えられる1層以上の有機物層とを含む有機電界発光素子であって、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に備えられ、前述した実施態様に係るコーティング組成物を用いて形成された正孔注入または輸送層をさらに含む有機電界発光素子を提供する。
第1電極と、第2電極と、前記第1電極と前記第2電極との間に備えられる1層以上の有機物層とを含む有機電界発光素子であって、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に備えられ、遷移金属酸化物および前記化学式1の単位を含む高分子を含む正孔注入または輸送層をさらに含む有機電界発光素子を提供する。
Aは、置換もしくは非置換のアルキレン基であり、アルキレン鎖のCのうち少なくとも1つの代わりに、芳香族炭化水素環、ヘテロ環、O、S、C(=O)、S(=O)、またはS(=O)2が位置してもよいし、
X1は、OまたはSであり、X2は、CR5R6、O、またはSであり、nは、1〜10の整数であり、pは、1〜10の整数であり、mは、0〜10の整数であり、
Yは、SO3H、SO3Li、SO3Na、SO3K、SO3Rb、またはSO3Csであり、
R1〜R6は、それぞれ独立に、水素、フッ素、アルキル基、またはフルオロアルキル基であり、ただし、R1およびR2の少なくとも1つは、フッ素である。
基板を準備するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に、前述した実施態様に係るコーティング組成物を用いて正孔注入または輸送層をコーティング方法で形成するステップをさらに含む。
ITOコーティングされたガラス基板を水、イソプロパノールで順次に洗浄した後、MoO2(acac)2とNafion(下記構造式A)を9:1の比率で混合してエチレングリコールモノメチルエーテルに溶かした溶液を、ITOが蒸着された基材上に3000rpmで30秒間スピンコーティングした。得られた薄膜を、酸素雰囲気下、200℃で15分間熱処理して、非常に均一な30nmの厚さの正孔注入層を形成した。
前記実施例1において、薄膜を窒素雰囲気で処理したことを除けば、同様の方法で素子を作製した。
前記実施例1において、Nafionに代えて、3M社のEW825(下記化学式D)を用いたことを除けば、同様の方法で素子を作製した。
前記実施例1において、Nafionに代えて、下記の化合物E(Mw=1,000,000)を用いたことを除けば、同様の方法で作製した。下記の化合物Eにおけるn:mの比率は2:8であった。
前記実施例1において、Nafionに代えて、下記の化合物F(Mw=500,000)を用いたことを除けば、同様の方法で作製した。下記の化合物Fにおけるl:mの比率は1:9であった。
前記実施例1において、添加剤なしにMoO2(acac)2のみを用いて正孔注入層を形成したことを除けば、同様の方法で素子を作製した。この実験では、素子の寿命特性が低下することを確認することができた。
前記実施例1において、MoO2(acac)2を用いず、Nafionのみを用いて正孔注入層を形成したことを除けば、同様の方法で素子を作製した。MoO2(acac)2のような有機金属錯体を含まず、Nafionのみを用いて形成された層は絶縁特性を示す。したがって、製造された素子の電圧特性が低下し、効率特性および寿命特性も低下することを確認することができた。
前記実施例1において、Nafionに代えて、ポリスチレンスルホン酸(polystyrene sulfonic acid、分子量Mw=75,000)(下記化学式G)を混合したことを除けば、同様の方法で素子を作製した。
前記実施例1において、Nafionに代えて、ポリビニルフェノール(polyvinylphenol)を用いたことを除けば、同様の方法で素子を作製した。この実験では、効率特性および寿命特性が低下することを確認することができた。
前記実施例1において、Nafionに代えて、デュポン社のZonyl FSN−100(下記化学式H、分子量=〜950)をアルドリッチ社から購入して用いたことを除けば、同様の方法で素子を作製した。
前記実施例1において、スルホニル基を含むNafionの代わりに、アミン基を含む単分子のドデシルアミンを9:1の比率で添加することを除けば、同様の方法で素子を作製した。この実験では、コーティング特性が相対的に不均一な現象が観察され、駆動電圧が増加する現象が観察された。
201:アノード
301:正孔注入層
401:正孔輸送層
501:発光層
601:電子輸送層
701:カソード
Claims (12)
- 遷移金属の有機金属錯体;
下記化学式1の単位を含む高分子;および
下記化学式5で表される溶媒を含有する有機溶媒を含む有機電界発光素子の正孔注入または輸送層コーティング組成物であって、
前記コーティング組成物中の遷移金属の有機金属錯体の含有量が、0.01〜50重量%である、コーティング組成物。
Aは、置換もしくは非置換のアルキレン基であり、アルキレン鎖のCのうち少なくとも1つの代わりに、芳香族炭化水素環、ヘテロ環、O、S、C(=O)、S(=O)、またはS(=O)2が位置してもよいし、
X1は、OまたはSであり、X2は、CR5R6、O、またはSであり、nは、1〜10の整数であり、pは、1〜10の整数であり、mは、0〜10の整数であり、
Yは、SO3H、SO3Li、SO3Na、SO3K、SO3Rb、またはSO3Csであり、
R1〜R6は、それぞれ独立に、水素、フッ素、アルキル基、またはフルオロアルキル基であり、ただし、R1およびR2の少なくとも1つは、フッ素である;
- 前記遷移金属の有機金属錯体の遷移金属は、3族〜11族の遷移金属である、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 前記遷移金属の有機金属錯体の遷移金属は、Mo、W、V、Re、Mn、またはRhである、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 前記化学式1の単位を含む高分子は、重量平均分子量2,000以上のものである、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 前記化学式1の前記Aは、アルキレン基を構成する少なくとも1つの炭素がフッ素で置換されたものである、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 前記化学式1は、下記化学式1−1または1−2で表されるものである、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物:
- 前記高分子の含有量は、コーティング組成物全体に対して0.01〜50重量%である、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 前記有機溶媒は、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノペンチルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジプロピルエーテル、エチレングリコールジブチルエーテル、エチレングリコールジペンチルエーテル、エチレングリコールジヘキシルエーテル、1,2プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,2−ブタンジオール、1,3−ブタンジオール、ジエチレングリコール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレンジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジブチルエーテル、エチレングリコールジアセテート、PEG600、およびトリエチレングリコールのうちの少なくとも1つを含むものである、請求項1に記載の有機電界発光素子の正孔注入または輸送層コーティング組成物。
- 基板を準備するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に、請求項1〜8のいずれか1項に記載のコーティング組成物を用いて正孔注入または輸送層をコーティング方法で形成するステップをさらに含む有機電界発光素子の製造方法。 - 前記コーティング組成物を用いて形成された正孔注入または輸送層の厚さは、1nm〜1,000nmである、請求項9に記載の有機電界発光素子の製造方法。
- 前記コーティング組成物を用いて形成された正孔注入または輸送層を形成した後、アニーリングするステップをさらに含む、請求項9に記載の有機電界発光素子の製造方法。
- 第1電極と、第2電極と、前記第1電極と前記第2電極との間に備えられる1層以上の有機物層とを含む有機電界発光素子であって、
前記第1電極と有機物層との間、または前記第2電極と有機物層との間に備えられ、請求項1〜8のいずれか1項に記載のコーティング組成物を用いて形成された正孔注入または輸送層をさらに含む有機電界発光素子。
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EP3498740B1 (en) | 2022-10-12 |
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US20200127202A1 (en) | 2020-04-23 |
KR101975352B1 (ko) | 2019-08-28 |
CN109715679B (zh) | 2021-10-15 |
WO2018084681A1 (ko) | 2018-05-11 |
KR102186092B1 (ko) | 2020-12-03 |
US11081646B2 (en) | 2021-08-03 |
KR20180051332A (ko) | 2018-05-16 |
JP2019534579A (ja) | 2019-11-28 |
EP3498740A1 (en) | 2019-06-19 |
EP3498740A4 (en) | 2019-08-21 |
KR102186093B1 (ko) | 2020-12-03 |
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