CN112334474B - 化合物及包含其的有机发光器件 - Google Patents

化合物及包含其的有机发光器件 Download PDF

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Publication number: CN112334474B
Authority: CN; China
Prior art keywords: substituted; unsubstituted; group; chemical formula; layer
Prior art date: 2018-11-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

CN201980043267.XA

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English (en)

Chinese (zh)

Other versions

CN112334474A (zh

Inventor

金明坤

琴水井

徐尚德

李东勋

洪玩杓

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

LG Chem Ltd

Original Assignee

LG Chem Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2018-11-13

Filing date

2019-11-06

Publication date

2023-07-21

2019-11-06 Application filed by LG Chem Ltd filed Critical LG Chem Ltd

2021-02-05 Publication of CN112334474A publication Critical patent/CN112334474A/zh

2023-07-21 Application granted granted Critical

2023-07-21 Publication of CN112334474B publication Critical patent/CN112334474B/zh

Status Active legal-status Critical Current

2039-11-06 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 title claims abstract description 85
239000000126 substance Substances 0.000 claims abstract description 139
239000010410 layer Substances 0.000 claims description 166
229910052805 deuterium Inorganic materials 0.000 claims description 61
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 60
125000003118 aryl group Chemical group 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 41
239000012044 organic layer Substances 0.000 claims description 39
238000002347 injection Methods 0.000 claims description 37
239000007924 injection Substances 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 31
125000001072 heteroaryl group Chemical group 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
230000000903 blocking effect Effects 0.000 claims description 18
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 18
230000005525 hole transport Effects 0.000 claims description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002560 nitrile group Chemical group 0.000 claims description 7
125000000732 arylene group Chemical group 0.000 claims description 5
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125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
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230000015572 biosynthetic process Effects 0.000 description 64
238000003786 synthesis reaction Methods 0.000 description 64
238000000034 method Methods 0.000 description 46
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MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 26
230000032258 transport Effects 0.000 description 24
239000000463 material Substances 0.000 description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
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OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
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125000002950 monocyclic group Chemical group 0.000 description 8
125000001624 naphthyl group Chemical group 0.000 description 8
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125000005509 dibenzothiophenyl group Chemical group 0.000 description 7
239000002019 doping agent Substances 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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125000000008 (C1-C10) alkyl group Chemical group 0.000 description 6
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239000002184 metal Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
150000004982 aromatic amines Chemical class 0.000 description 5
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PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
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IDGRUXUQFTUJOT-UHFFFAOYSA-N 2-(10-phenylanthracen-9-yl)dibenzofuran Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(OC=2C3=CC=CC=2)C3=C1 IDGRUXUQFTUJOT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NVCQMRCDIJQSAP-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)NC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C Chemical compound C(C)(C)(C)C1=CC=C(C=C1)NC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C NVCQMRCDIJQSAP-UHFFFAOYSA-N 0.000 description 3
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
239000000956 alloy Substances 0.000 description 3
229910045601 alloy Inorganic materials 0.000 description 3
239000010405 anode material Substances 0.000 description 3
125000005264 aryl amine group Chemical group 0.000 description 3
125000005605 benzo group Chemical group 0.000 description 3
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
229940125797 compound 12 Drugs 0.000 description 3
229920001940 conductive polymer Polymers 0.000 description 3
150000004696 coordination complex Chemical class 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
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229910052733 gallium Inorganic materials 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
238000004770 highest occupied molecular orbital Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
125000005561 phenanthryl group Chemical group 0.000 description 3
125000003367 polycyclic group Chemical group 0.000 description 3
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229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
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125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
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YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
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239000011248 coating agent Substances 0.000 description 2
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239000003599 detergent Substances 0.000 description 2
125000002720 diazolyl group Chemical group 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002219 fluoranthenes Chemical class 0.000 description 2
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150000002391 heterocyclic compounds Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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150000004706 metal oxides Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
238000005240 physical vapour deposition Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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229920000767 polyaniline Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
239000010453 quartz Substances 0.000 description 2
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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150000003852 triazoles Chemical class 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
KVSFGDUAHLJIBU-UHFFFAOYSA-N 2,4-dibromo-9,9-dimethyl-7,8-dihydrophenalene-1,5-diol Chemical compound CC(C)(CCC1=CC(O)=C2Br)C3=C1C2=CC(Br)=C3O KVSFGDUAHLJIBU-UHFFFAOYSA-N 0.000 description 1
UHZJDYJZKSTNTO-UHFFFAOYSA-N 2,5-dibromo-9,9-dimethyl-7,8-dihydrophenalene-1,4-diol Chemical compound CC1(CCC2=CC(=C(C3=CC(=C(C1=C23)O)Br)O)Br)C UHZJDYJZKSTNTO-UHFFFAOYSA-N 0.000 description 1
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229930192474 thiophene Natural products 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 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
125000001425 triazolyl group Chemical group 0.000 description 1
238000001771 vacuum deposition Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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]
- H10K50/14—Carrier transporting layers
- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Optics & Photonics (AREA)
Electroluminescent Light Sources (AREA)
Plural Heterocyclic Compounds (AREA)

CN201980043267.XA 2018-11-13 2019-11-06 化合物及包含其的有机发光器件 Active CN112334474B (zh)

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WO2018128470A1 (ko) *	2017-01-05	2018-07-12	머티어리얼사이언스 주식회사	유기전계발광소자

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KR102256782B1 (ko) *	2018-03-23	2021-05-26	주식회사 엘지화학	다환 화합물 및 이를 포함하는 유기 발광 소자

2019
- 2019-11-06 WO PCT/KR2019/014951 patent/WO2020101252A1/ko active Application Filing
- 2019-11-06 CN CN201980043267.XA patent/CN112334474B/zh active Active
- 2019-11-06 KR KR1020190140710A patent/KR102328788B1/ko active IP Right Grant

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JP2011204843A (ja) *	2010-03-25	2011-10-13	Toray Ind Inc	発光素子
KR20180018404A (ko) *	2016-08-09	2018-02-21	주식회사 엘지화학	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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