KR20120116269A - 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents

신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDF

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Publication number: KR20120116269A
Authority: KR; South Korea
Prior art keywords: substituted; unsubstituted; compound; alkyl; organic
Prior art date: 2011-04-12

Application number

KR1020110033910A

Other languages

English (en)

Korean (ko)

Inventor

안희춘

윤석근

김희숙

양수진

이경주

김남균

조영준

권혁주

김봉옥

Original Assignee

롬엔드하스전자재료코리아유한회사

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.)

2011-04-12

Filing date

2011-04-12

Publication date

2012-10-22

2011-04-12 Application filed by 롬엔드하스전자재료코리아유한회사 filed Critical 롬엔드하스전자재료코리아유한회사

2011-04-12 Priority to KR1020110033910A priority Critical patent/KR20120116269A/ko

2012-04-12 Priority to JP2014505079A priority patent/JP2014513083A/ja

2012-04-12 Priority to PCT/KR2012/002762 priority patent/WO2012141499A1/fr

2012-04-12 Priority to CN201280028741.XA priority patent/CN103619833A/zh

2012-04-12 Priority to TW101112951A priority patent/TW201249960A/zh

2012-04-12 Priority to EP12771699.1A priority patent/EP2697216A4/fr

2012-10-22 Publication of KR20120116269A publication Critical patent/KR20120116269A/ko

Links

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239000002019 doping agent Substances 0.000 claims abstract description 22
239000011368 organic material Substances 0.000 claims abstract description 13
239000000126 substance Substances 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims description 43
125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 39
-1 cyano, carbazolyl Chemical group 0.000 claims description 31
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125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
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229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
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125000001424 substituent group Chemical group 0.000 claims description 8
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239000011593 sulfur Chemical group 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
125000005566 carbazolylene group Chemical group 0.000 claims 1
125000005584 chrysenylene group Chemical group 0.000 claims 1
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239000007787 solid Substances 0.000 description 28
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238000002360 preparation method Methods 0.000 description 22
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
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239000008213 purified water Substances 0.000 description 13
239000011734 sodium Substances 0.000 description 13
ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 12
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235000019439 ethyl acetate Nutrition 0.000 description 10
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TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 9
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DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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0 C*(cc1)cc(c2cc(-c3ccccc3)ccc22)c1[n]2-c1ccccc1 Chemical compound C*(cc1)cc(c2cc(-c3ccccc3)ccc22)c1[n]2-c1ccccc1 0.000 description 5
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150000001204 N-oxides Chemical class 0.000 description 2
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235000019270 ammonium chloride Nutrition 0.000 description 2
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
229910052761 rare earth metal Inorganic materials 0.000 description 2
150000002910 rare earth metals Chemical class 0.000 description 2
230000027756 respiratory electron transport chain Effects 0.000 description 2
150000003839 salts Chemical group 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
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 1
TWOIWLFSUGLFHY-UHFFFAOYSA-N 1,4-diphenylbenzimidazole Chemical compound C1=NC2=C(C=3C=CC=CC=3)C=CC=C2N1C1=CC=CC=C1 TWOIWLFSUGLFHY-UHFFFAOYSA-N 0.000 description 1
MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-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
YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
ZCUPSHZNFJPULB-UHFFFAOYSA-N C(CC1)CC(C2C3)=C1NC2C=CC3c(cc1)cc2c1[o]c1ccccc21 Chemical compound C(CC1)CC(C2C3)=C1NC2C=CC3c(cc1)cc2c1[o]c1ccccc21 ZCUPSHZNFJPULB-UHFFFAOYSA-N 0.000 description 1
UTKOSVNHQBEKNR-UHFFFAOYSA-N C(CC1)CC(C2C3)=C1NC2C=CC3c(cc1)cc2c1[s]c1ccccc21 Chemical compound C(CC1)CC(C2C3)=C1NC2C=CC3c(cc1)cc2c1[s]c1ccccc21 UTKOSVNHQBEKNR-UHFFFAOYSA-N 0.000 description 1
SALKGZPYZJYHMX-UHFFFAOYSA-N C(CC1)CC2=C1NC1C=CC(c(cc3)cc4c3[s]c3ccccc43)=CC21 Chemical compound C(CC1)CC2=C1NC1C=CC(c(cc3)cc4c3[s]c3ccccc43)=CC21 SALKGZPYZJYHMX-UHFFFAOYSA-N 0.000 description 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
HNYNOKDUWSXYIX-UHFFFAOYSA-N CC1(C)c(ccc(C2C=CC3NC(CCCC4)=C4C3C2)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(C2C=CC3NC(CCCC4)=C4C3C2)c2)c2-c2ccccc12 HNYNOKDUWSXYIX-UHFFFAOYSA-N 0.000 description 1
229910004261 CaF 2 Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229910018068 Li 2 O Inorganic materials 0.000 description 1
YCAIECYQFONUCH-UHFFFAOYSA-N NC(CCCC1)C1C(C1C=CC(c(cc2)cc(c3ccc(CCC=C4)c4c33)c2[n]3-c2ccccc2)=CC1)[Mn] Chemical compound NC(CCCC1)C1C(C1C=CC(c(cc2)cc(c3ccc(CCC=C4)c4c33)c2[n]3-c2ccccc2)=CC1)[Mn] YCAIECYQFONUCH-UHFFFAOYSA-N 0.000 description 1
QWKFYAGZLGBCIE-UHFFFAOYSA-N OC(C(BC=C1)=C1C1=COC=C1)=O Chemical compound OC(C(BC=C1)=C1C1=COC=C1)=O QWKFYAGZLGBCIE-UHFFFAOYSA-N 0.000 description 1
229910003564 SiAlON Inorganic materials 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-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
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
150000001602 bicycloalkyls Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000005137 deposition process Methods 0.000 description 1
125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
HSSPXXSSTKINGH-UHFFFAOYSA-L dilithium quinoline-2-carboxylate Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Li+].[Li+].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] HSSPXXSSTKINGH-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
238000004020 luminiscence type Methods 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000001725 pyrenyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000010409 thin film Substances 0.000 description 1
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
238000002061 vacuum sublimation Methods 0.000 description 1

Classifications

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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

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

KR1020110033910A 2011-04-12 2011-04-12 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 KR20120116269A (ko)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
KR1020110033910A KR20120116269A (ko)	2011-04-12	2011-04-12	신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2014505079A JP2014513083A (ja)	2011-04-12	2012-04-12	有機電子材料のための新規化合物およびこれらを使用した有機エレクトロルミネセント素子
PCT/KR2012/002762 WO2012141499A1 (fr)	2011-04-12	2012-04-12	Nouveau composé pour matériau électronique organique et dispositif électroluminescent organique l'utilisant
CN201280028741.XA CN103619833A (zh)	2011-04-12	2012-04-12	用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件
TW101112951A TW201249960A (en)	2011-04-12	2012-04-12	Novel compounds for organic electronic material and organic electroluminescent device using the same
EP12771699.1A EP2697216A4 (fr)	2011-04-12	2012-04-12	Nouveau composé pour matériau électronique organique et dispositif électroluminescent organique l'utilisant

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KR1020110033910A KR20120116269A (ko)	2011-04-12	2011-04-12	신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자

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KR1020110033910A KR20120116269A (ko)	2011-04-12	2011-04-12	신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자

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EP (1)	EP2697216A4 (fr)
JP (1)	JP2014513083A (fr)
KR (1)	KR20120116269A (fr)
CN (1)	CN103619833A (fr)
TW (1)	TW201249960A (fr)
WO (1)	WO2012141499A1 (fr)

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KR20160037107A (ko) *	2014-09-26	2016-04-05	롬엔드하스전자재료코리아유한회사	유기 전계 발광 화합물, 및 이를 포함하는 유기 전계 발광 재료 및 유기 전계 발광 소자
KR20160056337A (ko) *	2014-11-10	2016-05-20	엘지디스플레이 주식회사	헤테로 화합물 및 이를 포함하는 유기전계발광소자
WO2020071860A1 (fr) *	2018-10-04	2020-04-09	주식회사 엘지화학	Composé et diode électroluminescente organique le comprenant
KR20210046613A (ko) *	2014-11-10	2021-04-28	엘지디스플레이 주식회사	헤테로 화합물 및 이를 포함하는 유기전계발광소자

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WO2015137471A1 (fr) *	2014-03-12	2015-09-17	出光興産株式会社	Composé, matériau pour élément électroluminescent organique, composition d'encre, élément électroluminescent organique et dispositif électronique
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WO2016048109A1 (fr) *	2014-09-26	2016-03-31	Rohm And Haas Electronic Materials Korea Ltd.	Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant
JP2018525331A (ja)	2015-06-10	2018-09-06	メルクパテントゲーエムベーハー	有機エレクトロルミネッセンス素子のための材料
TWI734694B (zh) *	2015-07-29	2021-08-01	德商麥克專利有限公司	含茀結構的化合物
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KR102515298B1 (ko) *	2017-07-10	2023-03-29	도레이 카부시키가이샤	발광 소자, 그것을 포함하는 디스플레이, 조명 장치 및 센서
CN108424420B (zh) *	2017-09-30	2021-01-12	北京绿人科技有限责任公司	含有硅原子的三嗪化合物及其应用和一种有机电致发光器件
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2011
- 2011-04-12 KR KR1020110033910A patent/KR20120116269A/ko not_active Application Discontinuation
2012
- 2012-04-12 CN CN201280028741.XA patent/CN103619833A/zh active Pending
- 2012-04-12 TW TW101112951A patent/TW201249960A/zh unknown
- 2012-04-12 EP EP12771699.1A patent/EP2697216A4/fr not_active Withdrawn
- 2012-04-12 JP JP2014505079A patent/JP2014513083A/ja active Pending
- 2012-04-12 WO PCT/KR2012/002762 patent/WO2012141499A1/fr active Application Filing

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Also Published As

Publication number	Publication date
JP2014513083A (ja)	2014-05-29
CN103619833A (zh)	2014-03-05
TW201249960A (en)	2012-12-16
EP2697216A4 (fr)	2014-10-15
WO2012141499A1 (fr)	2012-10-18
EP2697216A1 (fr)	2014-02-19

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Publication	Publication Date	Title
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KR20120116269A (ko)	2012-10-22	신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101427611B1 (ko)	2014-08-11	신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
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