JP2017510074A - 電子バッファリング材料及び有機電界発光デバイス - Google Patents
電子バッファリング材料及び有機電界発光デバイス Download PDFInfo
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- JP2017510074A JP2017510074A JP2016556986A JP2016556986A JP2017510074A JP 2017510074 A JP2017510074 A JP 2017510074A JP 2016556986 A JP2016556986 A JP 2016556986A JP 2016556986 A JP2016556986 A JP 2016556986A JP 2017510074 A JP2017510074 A JP 2017510074A
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- Prior art keywords
- substituted
- unsubstituted
- alkyl
- heteroaryl
- membered
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- 230000003139 buffering effect Effects 0.000 title claims abstract description 126
- 239000000463 material Substances 0.000 title claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims description 104
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 42
- -1 or NR 13 Chemical compound 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000005104 aryl silyl group Chemical group 0.000 claims description 31
- 125000001769 aryl amino group Chemical group 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Chemical group 0.000 claims description 12
- 239000011593 sulfur Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 6
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical class C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 221
- 230000032258 transport Effects 0.000 description 63
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 35
- 238000002347 injection Methods 0.000 description 31
- 239000007924 injection Substances 0.000 description 31
- 239000002019 doping agent Substances 0.000 description 30
- 230000005525 hole transport Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 238000001771 vacuum deposition Methods 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 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 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 150000004866 oxadiazoles Chemical class 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910016036 BaF 2 Inorganic materials 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- DWDHOTUTUOTLFA-UHFFFAOYSA-M cesium;quinoline-2-carboxylate Chemical compound [Cs+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 DWDHOTUTUOTLFA-UHFFFAOYSA-M 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002258 gallium Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 150000003854 isothiazoles Chemical class 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- JYILWUOXRMWVGD-UHFFFAOYSA-M potassium;quinoline-2-carboxylate Chemical compound [K+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 JYILWUOXRMWVGD-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- PLTCLMZAIZEHGD-UHFFFAOYSA-M sodium;quinoline-2-carboxylate Chemical compound [Na+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 PLTCLMZAIZEHGD-UHFFFAOYSA-M 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 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
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- RKLROMDZXDQSDF-UHFFFAOYSA-N 1-phenylphenanthrene Chemical compound C1=CC=CC=C1C1=CC=CC2=C1C=CC1=CC=CC=C21 RKLROMDZXDQSDF-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- LBWODEDBUKZKFS-UHFFFAOYSA-N [Li].N1=C(C(=O)O)C(C(=O)O)=CC=C1 Chemical compound [Li].N1=C(C(=O)O)C(C(=O)O)=CC=C1 LBWODEDBUKZKFS-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- 150000001450 anions Chemical class 0.000 description 1
- 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 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005878 benzonaphthofuranyl group Chemical group 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
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- LCPYTQFVQRPZCV-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 LCPYTQFVQRPZCV-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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- 150000002475 indoles Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 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
- 238000001931 thermography Methods 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
- 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
100:有機電界発光デバイス
101:基板
110:第1の電極
120:有機層
122:正孔注入層
123:正孔輸送層
125:発光層
126:電子バッファリング層
127:電子輸送層
128:電子注入層
129:電子輸送ゾーン
130:第2の電極
Claims (9)
- 以下の式1によって表される化合物を含む電子バッファリング材料であって、
Aは、置換もしくは非置換(5〜30員)ヘテロアリールを表し、
Lは、単結合、置換もしくは非置換(C6−C30)アリーレン、または置換もしくは 非置換(5〜30員)ヘテロアリーレンを表し、
R1は、以下の式2aまたは2bを表し、
R3は、水素、重水素、ハロゲン、シアノ、置換もしくは非置換(C1−C30)アルキル、置換もしくは非置換(C6−C30)アリール、置換もしくは非置換(5〜30員)ヘテロアリール、置換もしくは非置換(C3−C30)シクロアルキル、置換もしくは非置換(C1−C30)アルコキシ、置換もしくは非置換トリ(C1−C30)アルキルシリル、置換もしくは非置換トリ(C6−C30)アリールシリル、置換もしくは非置換ジ(C1−C30)アルキル(C6−C30)アリールシリル、置換もしくは非置換(C1−C30)アルキルジ(C6−C30)アリールシリル、置換もしくは非置換モノもしくはジ(C1−C30)アルキルアミノ、置換もしくは非置換モノもしくはジ(C6−C30)アリールアミノ、または置換もしくは非置換(C1−C30)アルキル(C6−C30)アリールアミノを表し、
R4、R5、R7、及びR10は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換(C1−C30)アルキル、置換もしくは非置換(C6−C30)アリール、置換もしくは非置換(5〜30員)ヘテロアリール、置換もしくは非置換(C3−C30)シクロアルキル、置換もしくは非置換(C1−C30)アルコキシ、置換もしくは非置換トリ(C1−C30)アルキルシリル、置換もしくは非置換トリ(C6−C30)アリールシリル、置換もしくは非置換ジ(C1−C30)アルキル(C6−C30)アリールシリル、置換もしくは非置換(C1−C30)アルキルジ(C6−C30)アリールシリル、置換もしくは非置換モノもしくはジ(C1−C30)アルキルアミノ、置換もしくは非置換モノもしくはジ(C6−C30)アリールアミノ、または置換もしくは非置換(C1−C30)アルキル(C6−C30)アリールアミノを表すか、あるいは隣接する置換基(複数可)に連結して置換もしくは非置換(C3−C30)の単環式もしくは多環式の脂環式もしくは芳香族環を形成し、その炭素原子(複数可)は窒素、酸素、及び硫黄から選択される少なくとも1個のヘテロ原子と置き換えられてもよく、
R6、R8、及びR9は、それぞれ独立して、置換もしくは非置換(C1−C30)アルキル、置換もしくは非置換(C6−C30)アリール、置換もしくは非置換(5〜30員)ヘテロアリール、置換もしくは非置換(C3−C30)シクロアルキル、置換もしくは非置換モノもしくはジ(C1−C30)アルキルアミノ、置換もしくは非置換モノもしくはジ(C6−C30)アリールアミノ、または置換もしくは非置換(C1−C30)アルキル(C6−C30)アリールアミノを表し、
R11〜R14は、それぞれ独立して、置換もしくは非置換(C1−C30)アルキル、置換もしくは非置換(C6−C30)アリール、または置換もしくは非置換(5〜30員)ヘテロアリールを表すか、あるいは隣接する置換基(複数可)に連結して置換もしくは非置換(C3−C30)の単環式もしくは多環式の脂環式もしくは芳香族環を形成し、その炭素原子(複数可)は窒素、酸素、及び硫黄から選択される少なくとも1個のヘテロ原子で置き換えられてもよく、
a、c、d、e、及びfは、それぞれ独立して、0〜4の整数を表し、a、c、d、e、またはfが2以上の整数である場合、R2、R4、R5、R7、またはR10の各々は、同じかまたは異なってもよく、
bは、0〜3の整数を表し、bが2以上の整数である場合、R3の各々は、同じかまたは異なってもよく、
nは、0または1の整数を表し、mは、1または2の整数を表し、
*は、前記カルバゾール骨格に対する結合部位を表し、
前記ヘテロアリール(エン)は、B、N、O、S、P(=O)、Si、及びPから選択される1個以上のヘテロ原子を含有する、前記電子バッファリング材料。 - Aは、置換もしくは非置換の窒素含有(5〜30員)ヘテロアリールを表し、Lは、単結合または置換もしくは非置換(C6−C20)アリーレンを表し、R1は、式2aまたは2bを表し、R2は、水素、重水素、置換もしくは非置換(C6−C20)アリール、置換もしくは非置換(5〜20員)ヘテロアリール、置換もしくは非置換モノもしくはジ(C6−C20)アリールアミノ、または式3を表すか、あるいは前記カルバゾール骨格と縮合して置換もしくは非置換ベンゾカルバゾールを形成し得、Xは、O、S、CR11R12、またはNR13を表し、R10は、水素または(C1−C20)アルキルを表し、R3、R4、R5、及びR7は、それぞれ独立して、水素または置換もしくは非置換(C1−C20)アルキルを表し、R6、R8及びR9は、それぞれ独立して、置換もしくは非置換(C1−C20)アルキル、置換もしくは非置換(C6−C20)アリール、または置換もしくは非置換(6〜20員)ヘテロアリールを表し、R11〜R14は、それぞれ独立して、水素、置換もしくは非置換(C1−C10)アルキル、置換もしくは非置換(C6−C20)アリール、または置換もしくは非置換(5〜20員)ヘテロアリールを表し、前記ヘテロアリールは、N、O、及びSから選択される1個以上のヘテロ原子を含有する、請求項1に記載の前記電子バッファリング材料。
- 以下の式11によって表される化合物が更に含まれ、
Ar5及びAr6は、それぞれ独立して、置換もしくは非置換(5〜30員)ヘテロアリール、または置換もしくは非置換(C6−C30)アリールを表し、
L’は、単結合、置換もしくは非置換(C6−C30)アリーレン、または置換もしくは非置換(3〜30員)ヘテロアリーレンを表し、
X1〜X3は、それぞれ独立して、NまたはCを表すが、但し、X1〜X3のうちの少なくとも1つがNを表すことを条件とし、
R15及びR16は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、カルボキシ、ニトロ、ヒドロキシ、置換もしくは非置換(C1−C30)アルキル、置換もしくは非置換(C6−C30)アリール、置換もしくは非置換(5〜30員)ヘテロアリール、置換もしくは非置換(C3−C30)シクロアルキル、置換もしくは非置換(C3−C30)シクロアルケニル、置換もしくは非置換(3〜7員)ヘテロシクロアルキル、置換もしくは非置換(C1−C30)アルコキシ、置換もしくは非置換トリ(C1−C30)アルキルシリル、置換もしくは非置換トリ(C6−C30)アリールシリル、置換もしくは非置換ジ(C1−C30)アルキル(C6−C30)アリールシリル、置換もしくは非置換(C1−C30)アルキルジ(C6−C30)アリールシリル、置換もしくは非置換モノもしくはジ(C1−C30)アルキルアミノ、置換もしくは非置換モノもしくはジ(C6−C30)アリールアミノ、または置換もしくは非置換(C1−C30)アルキル(C6−C30)アリールアミノを表すか、あるいは隣接する置換基(複数可)に連結して置換もしくは非置換(C3−C30)の単環式もしくは多環式の脂環式もしくは芳香族環を形成し、その炭素原子(複数可)は窒素、酸素、及び硫黄から選択される少なくとも1個のヘテロ原子で置き換えられてもよく、
前記ヘテロアリール(エン)及びヘテロシクロアルキルは、それぞれ独立して、B、N、O、S、P(=O)、Si、及びPから選択される1個以上のヘテロ原子を含有し、
s及びtは、それぞれ独立して、1〜4の整数を表し、sまたはtが2以上の整数である場合、R15またはR16の各々は、同じかまたは異なってもよい、請求項1に記載の前記電子バッファリング材料。 - Ar5及びAr6は、それぞれ独立して、置換もしくは非置換(6〜20員)ヘテロアリール、または置換もしくは非置換(C6−C20)アリールを表し、L’は、単結合、または置換もしくは非置換(C6−C20)アリーレンを表し、R15及びR16は、それぞれ独立して、水素、置換もしくは非置換(C6−C20)アリール、または置換もしくは非置換(5〜20員)ヘテロアリールを表すか、あるいは隣接する置換基(複数可)に連結して置換もしくは非置換(C5−C20)の単環式もしくは多環式の芳香族環を形成し、その炭素原子(複数可)は窒素、酸素、及び硫黄から選択される少なくとも1個のヘテロ原子と置き換えられてもよく、s及びtは、1を表す、請求項4に記載の前記電子バッファリング材料。
- 第1の電極、前記第1の電極に対向する第2の電極、前記第1の電極と前記第2の電極との間の発光層、ならびに前記発光層と前記第2の電極との間の電子輸送ゾーン及び電子バッファリング層を備え、前記電子バッファリング層は、請求項1に記載の式1によって表される前記化合物を含む、有機電界発光デバイス。
- 前記電子バッファリング層は、請求項4に記載の式11によって表される前記化合物を更に含む、請求項7に記載の前記有機電界発光デバイス。
- 前記電子バッファリング層の式1によって表される前記化合物及び式11によって表される前記化合物は、同時蒸着または混合蒸着される、請求項8に記載の前記有機電界発光デバイス。
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017513242A (ja) * | 2014-04-04 | 2017-05-25 | エルジー・ケム・リミテッド | 有機発光素子 |
JP2017529689A (ja) * | 2014-07-29 | 2017-10-05 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 電子緩衝材及び有機エレクトロルミネセントデバイス |
JP2018181460A (ja) * | 2017-04-05 | 2018-11-15 | 株式会社Joled | 有機el表示パネル及び有機el表示パネルの製造方法 |
JP2021052209A (ja) * | 2014-05-23 | 2021-04-01 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、及び照明装置 |
WO2022209812A1 (ja) * | 2021-03-31 | 2022-10-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、電子機器、及び組成物 |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150108330A (ko) * | 2014-03-17 | 2015-09-25 | 롬엔드하스전자재료코리아유한회사 | 전자 버퍼 재료 및 이를 포함하는 유기 전계 발광 소자 |
KR102427918B1 (ko) * | 2014-04-29 | 2022-08-03 | 롬엔드하스전자재료코리아유한회사 | 전자전달재료 및 이를 포함하는 유기 전계 발광 소자 |
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US10496720B2 (en) * | 2016-08-04 | 2019-12-03 | Facebook, Inc. | Systems and methods for providing feed preference surveys in a social networking system |
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KR102508374B1 (ko) * | 2018-04-17 | 2023-03-10 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR102312487B1 (ko) * | 2018-09-04 | 2021-10-14 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기발광소자 |
US11485706B2 (en) | 2018-09-11 | 2022-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2020063592A1 (zh) * | 2018-09-29 | 2020-04-02 | Tcl集团股份有限公司 | 一种量子点发光二极管 |
KR102213664B1 (ko) | 2018-11-28 | 2021-02-05 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
KR102080737B1 (ko) * | 2019-05-29 | 2020-02-24 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
CN113661584B (zh) * | 2019-06-19 | 2024-04-26 | 株式会社Lg化学 | 有机发光器件 |
CN113540369A (zh) | 2020-04-13 | 2021-10-22 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光装置 |
KR20220059767A (ko) * | 2020-11-03 | 2022-05-10 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
CN115181095B (zh) * | 2022-07-06 | 2024-03-22 | 天津大学 | 具有荧光-延迟荧光-室温磷光三重发射特性的嘧啶基发光体及其制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012014500A1 (ja) * | 2010-07-30 | 2012-02-02 | 保土谷化学工業株式会社 | インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
JP2012528088A (ja) * | 2009-05-29 | 2012-11-12 | 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センス素子のための材料 |
JP2012531737A (ja) * | 2009-06-25 | 2012-12-10 | チェイル インダストリーズ インコーポレイテッド | 有機光電子素子用化合物、それを含む有機発光ダイオード、および前記有機発光ダイオードを含む表示装置 |
WO2013041176A1 (de) * | 2011-09-21 | 2013-03-28 | Merck Patent Gmbh | Carbazolderivate für organische elektrolumineszenzvorrichtungen |
WO2014038867A1 (en) * | 2012-09-07 | 2014-03-13 | Rohm And Haas Electronic Materials Korea Ltd. | A novel combination of a host compound and a dopant compound and an organic electroluminescence device comprising the same |
US20150053939A1 (en) * | 2013-08-20 | 2015-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2016111346A (ja) * | 2014-12-09 | 2016-06-20 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 有機光電子素子および表示装置 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101002733B1 (ko) * | 2007-09-14 | 2010-12-21 | 제일모직주식회사 | 유기 화합물, 및 이를 포함하는 유기광전소자 |
WO2010131930A2 (ko) * | 2009-05-15 | 2010-11-18 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
DE102009031021A1 (de) * | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
TW201301598A (zh) | 2010-11-22 | 2013-01-01 | Idemitsu Kosan Co | 有機電激發光元件 |
KR101375357B1 (ko) * | 2011-01-07 | 2014-03-26 | (주)씨에스엘쏠라 | 유기 광화합물 및 이를 구비한 유기 광소자 |
US9530969B2 (en) * | 2011-12-05 | 2016-12-27 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device |
WO2013183851A1 (ko) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
KR20130136359A (ko) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
CN102977006A (zh) * | 2012-12-21 | 2013-03-20 | 南京邮电大学 | 吡啶芴类有机电致磷光主体发光材料及其制备方法 |
KR102184893B1 (ko) * | 2013-12-04 | 2020-12-01 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
-
2015
- 2015-03-16 KR KR1020150036207A patent/KR102411748B1/ko active IP Right Grant
- 2015-03-17 EP EP18180522.7A patent/EP3415508B1/en active Active
- 2015-03-17 EP EP15764804.9A patent/EP3119751B1/en active Active
- 2015-03-17 CN CN201580012893.4A patent/CN106068261B/zh active Active
- 2015-03-17 US US15/125,611 patent/US20170005276A1/en not_active Abandoned
- 2015-03-17 JP JP2016556986A patent/JP6741584B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012528088A (ja) * | 2009-05-29 | 2012-11-12 | 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センス素子のための材料 |
JP2012531737A (ja) * | 2009-06-25 | 2012-12-10 | チェイル インダストリーズ インコーポレイテッド | 有機光電子素子用化合物、それを含む有機発光ダイオード、および前記有機発光ダイオードを含む表示装置 |
WO2012014500A1 (ja) * | 2010-07-30 | 2012-02-02 | 保土谷化学工業株式会社 | インデノカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
WO2013041176A1 (de) * | 2011-09-21 | 2013-03-28 | Merck Patent Gmbh | Carbazolderivate für organische elektrolumineszenzvorrichtungen |
WO2014038867A1 (en) * | 2012-09-07 | 2014-03-13 | Rohm And Haas Electronic Materials Korea Ltd. | A novel combination of a host compound and a dopant compound and an organic electroluminescence device comprising the same |
US20150053939A1 (en) * | 2013-08-20 | 2015-02-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2016111346A (ja) * | 2014-12-09 | 2016-06-20 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 有機光電子素子および表示装置 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017513242A (ja) * | 2014-04-04 | 2017-05-25 | エルジー・ケム・リミテッド | 有機発光素子 |
JP2021052209A (ja) * | 2014-05-23 | 2021-04-01 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、及び照明装置 |
JP7035158B2 (ja) | 2014-05-23 | 2022-03-14 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、及び照明装置 |
JP2017529689A (ja) * | 2014-07-29 | 2017-10-05 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 電子緩衝材及び有機エレクトロルミネセントデバイス |
JP2018181460A (ja) * | 2017-04-05 | 2018-11-15 | 株式会社Joled | 有機el表示パネル及び有機el表示パネルの製造方法 |
WO2022209812A1 (ja) * | 2021-03-31 | 2022-10-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、電子機器、及び組成物 |
Also Published As
Publication number | Publication date |
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CN106068261A (zh) | 2016-11-02 |
KR102411748B1 (ko) | 2022-06-23 |
CN106068261B (zh) | 2019-08-23 |
US20170005276A1 (en) | 2017-01-05 |
EP3415508B1 (en) | 2021-04-21 |
EP3415508A1 (en) | 2018-12-19 |
EP3119751A1 (en) | 2017-01-25 |
KR20150108332A (ko) | 2015-09-25 |
EP3119751A4 (en) | 2017-12-27 |
EP3119751B1 (en) | 2020-06-17 |
JP6741584B2 (ja) | 2020-08-19 |
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