KR102595751B1 - 이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 - Google Patents
이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 Download PDFInfo
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- KR102595751B1 KR102595751B1 KR1020180092970A KR20180092970A KR102595751B1 KR 102595751 B1 KR102595751 B1 KR 102595751B1 KR 1020180092970 A KR1020180092970 A KR 1020180092970A KR 20180092970 A KR20180092970 A KR 20180092970A KR 102595751 B1 KR102595751 B1 KR 102595751B1
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- 239000000463 material Substances 0.000 title abstract description 40
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- 125000003118 aryl group Chemical group 0.000 claims description 116
- 125000001931 aliphatic group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 88
- 229910052760 oxygen Inorganic materials 0.000 claims description 60
- 229910052717 sulfur Inorganic materials 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- 229910052698 phosphorus Inorganic materials 0.000 claims description 56
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 51
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- 239000002019 doping agent Substances 0.000 description 7
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- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 3
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- WFQGENWZOASRDN-UHFFFAOYSA-N 18-bromo-21,21-dimethylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound CC1(C)c2cc(Br)ccc2-c2c1c1ccccc1c1ccccc21 WFQGENWZOASRDN-UHFFFAOYSA-N 0.000 description 1
- NYLZJEBTWCYOLU-UHFFFAOYSA-N 18-bromo-21-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=C(Br)C=C1O2 NYLZJEBTWCYOLU-UHFFFAOYSA-N 0.000 description 1
- ZAARQOHTIYBPNJ-UHFFFAOYSA-N 2,4-dichloro-6-naphthalen-2-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=C3C=CC=CC3=CC=2)=N1 ZAARQOHTIYBPNJ-UHFFFAOYSA-N 0.000 description 1
- FGJDRITYPHJFOH-UHFFFAOYSA-N 2-bromo-1-nitro-4-phenylbenzene Chemical group C1=C(Br)C([N+](=O)[O-])=CC=C1C1=CC=CC=C1 FGJDRITYPHJFOH-UHFFFAOYSA-N 0.000 description 1
- MQAIWWRJGVSXKV-UHFFFAOYSA-N 2-bromo-11,11-dimethylbenzo[b]fluorene Chemical compound C1=CC=C2C=C3C(C)(C)C4=CC(Br)=CC=C4C3=CC2=C1 MQAIWWRJGVSXKV-UHFFFAOYSA-N 0.000 description 1
- KRQFZBUWIOZDMP-UHFFFAOYSA-N 2-bromo-3-nitronaphthalene Chemical compound C1=CC=C2C=C(Br)C([N+](=O)[O-])=CC2=C1 KRQFZBUWIOZDMP-UHFFFAOYSA-N 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
- SXNOGSKQBHIZHE-UHFFFAOYSA-N 2-bromonaphtho[2,3-b][1]benzofuran Chemical compound C1=CC=C2C=C(C=3C(=CC=C(C=3)Br)O3)C3=CC2=C1 SXNOGSKQBHIZHE-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- SHQUCGSWCVZRSN-UHFFFAOYSA-N 2-naphthalen-1-yl-1,3,2-dioxaborolane Chemical compound O1CCOB1C1=CC=CC2=CC=CC=C12 SHQUCGSWCVZRSN-UHFFFAOYSA-N 0.000 description 1
- APMRBMVOHVFKDR-UHFFFAOYSA-N 3-(4-bromo-3-nitrophenyl)-9-phenylcarbazole Chemical compound BrC1=C(C=C(C=C1)C=1C=CC=2N(C3=CC=CC=C3C=2C=1)C1=CC=CC=C1)[N+](=O)[O-] APMRBMVOHVFKDR-UHFFFAOYSA-N 0.000 description 1
- VECLPBKDHAALGQ-UHFFFAOYSA-N 3-bromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 VECLPBKDHAALGQ-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- CILFAGAHAXTTLN-UHFFFAOYSA-N 4-bromo-12-oxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound BrC1=CC2=C(OC3=C2C=CC2=CC=CC=C23)C=2C=CC=CC1=2 CILFAGAHAXTTLN-UHFFFAOYSA-N 0.000 description 1
- QWJWPDHACGGABF-UHFFFAOYSA-N 5,5-dimethylcyclopenta-1,3-diene Chemical compound CC1(C)C=CC=C1 QWJWPDHACGGABF-UHFFFAOYSA-N 0.000 description 1
- MBEIUMZROARQFG-UHFFFAOYSA-N 5-bromonaphtho[1,2-b][1]benzothiole Chemical compound S1C2=C3C=CC=C[C]3C(Br)=CC2=C2[C]1C=CC=C2 MBEIUMZROARQFG-UHFFFAOYSA-N 0.000 description 1
- XHJCHUVWJCDJPN-UHFFFAOYSA-N 9-bromo-10-nitrophenanthrene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Br)C3=CC=CC=C3C2=C1 XHJCHUVWJCDJPN-UHFFFAOYSA-N 0.000 description 1
- OCABOBVDPZEMCC-UHFFFAOYSA-N 9-bromo-11-phenylbenzo[a]carbazole Chemical compound C=1C(Br)=CC=C(C2=C3C4=CC=CC=C4C=C2)C=1N3C1=CC=CC=C1 OCABOBVDPZEMCC-UHFFFAOYSA-N 0.000 description 1
- SCFYLUFGTCXFSI-UHFFFAOYSA-N 9-bromo-7-phenylbenzo[c]carbazole Chemical compound C=1C(Br)=CC=C(C2=C3C=CC=CC3=CC=C22)C=1N2C1=CC=CC=C1 SCFYLUFGTCXFSI-UHFFFAOYSA-N 0.000 description 1
- JEGZRTMZYUDVBF-UHFFFAOYSA-N Benz[a]acridine Chemical compound C1=CC=C2C3=CC4=CC=CC=C4N=C3C=CC2=C1 JEGZRTMZYUDVBF-UHFFFAOYSA-N 0.000 description 1
- MAWIMXZUWQPCJQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+]C=1N=C(C2=CC=CC=C2C=1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+]C=1N=C(C2=CC=CC=C2C=1)C1=CC=CC=C1 MAWIMXZUWQPCJQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 208000006930 Pseudomyxoma Peritonei Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- DYKOWEPRWGFRAF-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinazoline Chemical compound C1=NC=NC2=C3C4=CC=CC=C4OC3=CC=C21 DYKOWEPRWGFRAF-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- SWJXWSAKHXBQSY-UHFFFAOYSA-N benzo(c)cinnoline Chemical compound C1=CC=C2C3=CC=CC=C3N=NC2=C1 SWJXWSAKHXBQSY-UHFFFAOYSA-N 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- NHVNWPIMHDTDPP-UHFFFAOYSA-N dibenzothiophen-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3SC2=C1 NHVNWPIMHDTDPP-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical group C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 description 1
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical group C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
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KR1020180092970A KR102595751B1 (ko) | 2018-08-09 | 2018-08-09 | 이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 |
PCT/KR2019/008970 WO2020032424A1 (fr) | 2018-08-09 | 2019-07-19 | Élément électronique organique comprenant, en tant que matériau hôte, un mélange de différents types de composés, et dispositif électronique associé |
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KR1020180092970A KR102595751B1 (ko) | 2018-08-09 | 2018-08-09 | 이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 |
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CN110330506A (zh) * | 2019-04-29 | 2019-10-15 | 宁波卢米蓝新材料有限公司 | 一种稠合多环化合物及其制备方法和用途 |
EP3757100B1 (fr) * | 2019-06-25 | 2022-12-28 | Novaled GmbH | Composés de triazine substitués par des groupes volumineux |
KR20210146113A (ko) * | 2020-05-26 | 2021-12-03 | 엘티소재주식회사 | 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물 |
US20230284526A1 (en) | 2020-06-30 | 2023-09-07 | Nippon Steel Chemical & Material Co., Ltd. | Organic electroluminescent element |
KR20220013910A (ko) * | 2020-07-27 | 2022-02-04 | 엘티소재주식회사 | 헤테로고리 화합물, 및 이를 포함하는 유기 발광 소자 |
US20230240140A1 (en) * | 2020-08-04 | 2023-07-27 | Lg Chem, Ltd. | Organic light emitting device |
KR102536903B1 (ko) * | 2020-08-13 | 2023-05-26 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물 |
CN114315799B (zh) * | 2020-09-29 | 2023-11-14 | 江苏三月科技股份有限公司 | 一种含三嗪结构的化合物及其应用 |
US11800800B1 (en) * | 2020-10-26 | 2023-10-24 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
US11527727B2 (en) * | 2020-10-26 | 2022-12-13 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
KR20220059767A (ko) * | 2020-11-03 | 2022-05-10 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
KR102438159B1 (ko) * | 2021-05-24 | 2022-08-30 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102441537B1 (ko) * | 2021-05-24 | 2022-09-07 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN113801057B (zh) * | 2021-08-13 | 2023-04-18 | 浙江大学 | 䓛基氮杂[7]螺烯类化合物、制备方法及应用 |
WO2023096405A1 (fr) * | 2021-11-26 | 2023-06-01 | 주식회사 엘지화학 | Nouveau composé et dispositif électroluminescent organique le comprenant |
KR102377494B1 (ko) * | 2021-12-13 | 2022-03-22 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2024121133A1 (fr) | 2022-12-08 | 2024-06-13 | Merck Patent Gmbh | Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques |
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KR101754715B1 (ko) * | 2014-04-08 | 2017-07-10 | 롬엔드하스전자재료코리아유한회사 | 복수종의 호스트 재료와 이를 포함하는 유기 전계 발광 소자 |
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KR102501666B1 (ko) * | 2016-01-11 | 2023-02-21 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20180038834A (ko) * | 2016-10-07 | 2018-04-17 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
-
2018
- 2018-08-09 KR KR1020180092970A patent/KR102595751B1/ko active IP Right Grant
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2019
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KR20200017727A (ko) | 2020-02-19 |
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