JP5782503B2 - Novel organic electroluminescent compound and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compound and organic electroluminescent device using the same Download PDFInfo
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- JP5782503B2 JP5782503B2 JP2013507866A JP2013507866A JP5782503B2 JP 5782503 B2 JP5782503 B2 JP 5782503B2 JP 2013507866 A JP2013507866 A JP 2013507866A JP 2013507866 A JP2013507866 A JP 2013507866A JP 5782503 B2 JP5782503 B2 JP 5782503B2
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- JP
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- Prior art keywords
- alkyl
- aryl
- organic electroluminescent
- heteroaryl
- arylsilyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 239000010410 layer Substances 0.000 claims description 36
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000005104 aryl silyl group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 21
- -1 piperidino, morpholino, thiomorpholino Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 9
- 125000004450 alkenylene group Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 150000001602 bicycloalkyls Chemical group 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 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 2
- 238000000034 method Methods 0.000 description 2
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 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 1
- XHZUPQUVMGRPDC-UHFFFAOYSA-N 1,2,3,4-tetratert-butylperylene Chemical group C1=CC(C2=C(C(C(C)(C)C)=C(C=3C2=C2C=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)=C3C2=CC=CC3=C1 XHZUPQUVMGRPDC-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
- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-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
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 150000001204 N-oxides Chemical class 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
- 239000007983 Tris buffer Substances 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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol 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-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
- 229910052787 antimony Inorganic materials 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 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
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 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
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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Description
本発明は、新規の有機電界発光化合物（ｏｒｇａｎｉｃ ｅｌｅｃｔｒｏｌｕｍｉｎｅｓｃｅｎｔ ｃｏｍｐｏｕｎｄ）、並びにこれを使用する有機電界発光素子（ｏｒｇａｎｉｃ ｅｌｅｃｔｒｏｌｕｍｉｎｅｓｃｅｎｔ ｄｅｖｉｃｅ）に関し、より具体的には、青色電界発光材料として使用される新規有機電界発光化合物およびこれをドーパントとして使用する有機電界発光素子に関する。 The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same, and more specifically, a novel organic electroluminescent used as a blue electroluminescent material. The present invention relates to a compound and an organic electroluminescent device using the compound as a dopant.
ディスプレイ素子の中では、電界発光（ｅｌｅｃｔｒｏｌｕｍｉｎｅｓｃｅｎｔ；ＥＬ）素子は、それが自己発光型ディスプレイ素子として広い視野角、優れたコントラストおよび速い応答速度を提供するという点で有利である。１９８７年に、イーストマンコダック（Ｅａｓｔｍａｎ Ｋｏｄａｋ）は、電界発光層を形成するための物質として、低分子量芳香族ジアミンとアルミニウム錯体を使用する有機ＥＬ素子を初めて開発した［Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１，９１３，１９８７］。 Among display elements, an electroluminescent (EL) element is advantageous in that it provides a wide viewing angle, excellent contrast and fast response speed as a self-luminous display element. In 1987, Eastman Kodak first developed an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
有機ＥＬ素子においては、ルミネッセンス効率および駆動寿命をはじめとするその性能を決定する最も重要な要因は電界発光材料である。電界発光材料のいくつかの要件には、固体状態での高い電界発光量子収率、高い電子および正孔移動度、真空蒸着中の分解に対する耐性、均一な膜を形成する能力、並びに安定性が挙げられる。 In an organic EL element, the most important factor that determines its performance including luminescence efficiency and driving life is an electroluminescent material. Some requirements for electroluminescent materials include high electroluminescent quantum yield in the solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form a uniform film, and stability. Can be mentioned.
有機電界発光材料は大まかに、高分子材料と低分子材料とに分類されうる。低分子材料には、分子構造の観点から、金属錯体と、金属を含まない完全有機電界発光材料とが挙げられる。トリス（８−キノリノラト）アルミニウム錯体のようなキレート錯体、クマリン誘導体、テトラフェニルブタジエン誘導体、ビス（スチリルアリーレン）誘導体、およびオキサジアゾール誘導体などが挙げられる。これらの材料から、青色から赤色の可視領域の光の放射が得られうることが報告されており、そしてカラーディスプレイ素子が実現されるであろうことが期待されている。 Organic electroluminescent materials can be broadly classified into high molecular materials and low molecular materials. Low molecular materials include metal complexes and fully organic electroluminescent materials that do not contain metals from the viewpoint of molecular structure. Examples include chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bis (styrylarylene) derivatives, and oxadiazole derivatives. From these materials it has been reported that light emission in the visible range from blue to red can be obtained and it is expected that color display elements will be realized.
その一方で、従来の青色材料については、出光興産によるジフェニルビニル−ビフェニル（ＤＰＶＢｉ）（化合物ａ）の開発以来、多くの材料が開発されかつ商業化されてきた。出光興産からの青色材料系に加えて、コダックのジナフチルアントラセン（ＤＮＡ）（化合物ｂ）、テトラ（ｔ−ブチル）ペリレン（化合物ｃ）系などが知られている。しかし、これら材料に関して大規模な研究および開発が行われるべきである。 On the other hand, many conventional materials have been developed and commercialized since the development of diphenylvinyl-biphenyl (DPVBi) (compound a) by Idemitsu Kosan. In addition to the blue material system from Idemitsu Kosan, Kodak's dinaphthylanthracene (DNA) (compound b), tetra (t-butyl) perylene (compound c) system and the like are known. However, extensive research and development should be done on these materials.
今までで最も高い効率を有することが知られている出光興産のジスチリル（ｄｉｓｔｒｙｌ）化合物系は、６ ｌｍ／Ｗの電力効率、および３０，０００時間を超える有利な素子寿命を有する。しかし、それがフルカラーディスプレイに適用される場合には、駆動時間の経過による色純度の低下のせいで、その寿命は数千時間にすぎない。青色電界発光の場合には、電界発光波長が長波長側に少しだけシフトすると、それは発光効率の観点からは有利になる。しかし、青色の満足できない色純度のせいで、高品質のディスプレイにその材料を適用するのは容易ではない。さらに、色純度、効率および熱安定性の問題のせいで、そのような材料の研究および開発が急を要している。 Idemitsu Kosan's distyryl compound system, which is known to have the highest efficiency to date, has a power efficiency of 6 lm / W and an advantageous device lifetime of over 30,000 hours. However, when it is applied to a full color display, its lifetime is only a few thousand hours due to the decrease in color purity over time. In the case of blue electroluminescence, if the electroluminescence wavelength is slightly shifted to the longer wavelength side, it is advantageous from the viewpoint of luminous efficiency. However, due to the unsatisfactory color purity of blue, it is not easy to apply the material to high quality displays. In addition, the research and development of such materials is urgent because of the problems of color purity, efficiency and thermal stability.
上述のような従来技術の課題を解決するための集中的な取り組みによって、本発明者は優れた発光効率および著しく改良された寿命特性を有する有機電界発光素子を実現する新規有機電界発光化合物を発明した。本発明の目的は、上記課題を解決しつつ、従来のドーパント材料と比較してより良好な発光効率および素子寿命を提供する、適切な色座標を有する骨格を有する有機電界発光化合物、並びに当該有機電界発光化合物を使用する高効率かつ長寿命の有機電界発光素子を提供することである。 Through intensive efforts to solve the problems of the prior art as described above, the present inventors invented a novel organic electroluminescent compound that realizes an organic electroluminescent device having excellent luminous efficiency and remarkably improved lifetime characteristics. did. An object of the present invention is to solve the above-mentioned problems and provide an organic electroluminescent compound having a skeleton having an appropriate color coordinate, which provides better luminous efficiency and device lifetime as compared with conventional dopant materials, and the organic It is to provide a highly efficient and long-life organic electroluminescent device using an electroluminescent compound.
新規有機電界発光化合物、およびこれを使用する有機電界発光素子が提供される。この有機電界発光化合物は化学式１によって表される化合物である。青色の優れた発光効率および優れた寿命特性を有するので、本発明に従った有機電界発光化合物は、非常に優れた駆動寿命を有するＯＬＥＤ素子を製造するために使用されうる。 A novel organic electroluminescent compound and an organic electroluminescent device using the same are provided. This organic electroluminescent compound is a compound represented by Chemical Formula 1. The organic electroluminescent compound according to the present invention can be used to produce an OLED device having a very good driving life since it has excellent luminous efficiency and excellent lifetime characteristics of blue.
Ａｒ１〜Ａｒ４は独立して、（Ｃ６−Ｃ３０）アリール、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む（Ｃ２−Ｃ３０）ヘテロアリール、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、アダマンチル、（Ｃ７−Ｃ３０）ビシクロアルキル、または
Ｒ１〜Ｒ６およびＲ１１〜Ｒ１３は独立して、水素、（Ｃ１−Ｃ３０）アルキル、（Ｃ３−Ｃ３０）シクロアルキル、（Ｃ６−Ｃ３０）アリール、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ６−Ｃ６０）アリールオキシ、モノもしくはジ（Ｃ１−Ｃ３０）アルキルアミノ、モノもしくはジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキルアミノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、またはトリ（Ｃ６−Ｃ３０）アリールシリルを表し；
Ｒ２１〜Ｒ２３は独立して、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、モルホリノ、チオモルホリノ、ピペリジノ、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、アダマンチル、ハロゲン、シアノ、（Ｃ６−Ｃ３０）アリール、（Ｃ２−Ｃ３０）ヘテロアリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、もしくはトリ（Ｃ６−Ｃ３０）アリールシリルを表すか、またはＲ２２とＲ２３とは縮合環を有するかもしくは有しない（Ｃ３−Ｃ３０）アルケニレンもしくは（Ｃ３−Ｃ３０）アルキレンを介して連結されて縮合環を形成していてよく；並びに
Ｒ１〜Ｒ６のアルキル、シクロアルキル、アリール、ヘテロアリール、アルコキシ、アリールオキシ、アルキルアミノ、アリールアミノ、アリールアルキルアミノ、トリアルキルシリル、ジアルキルアリールシリルもしくはトリアリールシリル；Ａｒ１〜Ａｒ４のアリール、ヘテロアリール、ヘテロシクロアルキル、シクロアルキル、アダマンチルもしくはビシクロアルキル；Ａ１とＡ２またはＡｒ３とＡｒ４のそれぞれの連結によって形成される縮合環；並びに、Ｒ２１〜Ｒ２３のアルキル、ハロアルキル、アルコキシ、モルホリノ、チオモルホリノ、ピペリジノ、ヘテロシクロアルキル、シクロアルキル、アダマンチル、アリール、ヘテロアリール、トリアルキルシリル、ジアルキルアリールシリル、またはトリアリールシリルは、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ１−Ｃ３０）アルキルチオ、ピペリジノ、モルホリノ、チオモルホリノ、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、ニトロ、ヒドロキシル、（Ｃ６−Ｃ３０）アリール、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１以上の置換基によってさらに置換されていてよい。
Ar 1 to Ar 4 are independently selected from (C 2 -C 30) heteroaryl, N, O and S containing one or more heteroatoms selected from (C 6 -C 30) aryl, N, O and S 5- to 7-membered heterocycloalkyl containing one or more heteroatoms, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl, or
R 1 to R 6 and R 11 to R 13 are independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1 -C30) alkoxy, (C6-C60) aryloxy, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, tri Represents (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, or tri (C6-C30) arylsilyl;
R 21 to R 23 are independently one or more selected from (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, morpholino, thiomorpholino, piperidino, N, O and S 5-membered to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, halogen, cyano, (C6-C30) aryl, (C2-C30) heteroaryl, tri (C1-C30) Represents alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, or tri (C6-C30) arylsilyl, or R 22 and R 23 have or are not fused (C3- C30) linked via alkenylene or (C3-C30) alkylene to form a condensed ring ; And R alkyl of 1 to R 6, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkyl aryl silyl or triarylsilyl; Ar 1 to Ar 4 An aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl; a fused ring formed by the respective linkage of A 1 and A 2 or Ar 3 and Ar 4 ; and an alkyl of R 21 to R 23 , Haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl, or triary Rusilyl is one or more selected from (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomorpholino, N, O and S. 5- to 7-membered heterocycloalkyl, including (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30) aryl, (C6-C30) aryloxy, (C6-C30) ) Arylthio, (C2-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1- C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) It may be further substituted by one or more substituents selected from the group consisting of Rirushiriru.
本発明においては、「アルキル」、「アルコキシ」および「アルキル」部分を含む他の置換基には、線状もしくは分岐の種類のいずれも挙げられる。本発明においては、「アリール」は、１つの水素原子を除去することにより芳香族炭化水素から得られる有機基を意味し、４員〜７員、特に５員もしくは６員の単環もしくは縮合環を含むことができる。具体的な例としては、フェニル、ナフチル、ビフェニル、アントリル、インデニル、フルオレニル、フェナントリル、トリフェニレニル、ピレニル、ペリレニル、クリセニル、ナフタセニル、フルオランテニルなどが挙げられるが、これらに限定されない。本発明において、「ヘテロアリール」は、芳香環骨格原子（１つもしくは複数）としてＢ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、ＳｉおよびＳｅから選択される１〜４個のヘテロ原子を含み、他の残りの芳香環骨格原子が炭素であるアリール基を意味する。それは、５員もしくは６員の単環式ヘテロアリール、またはベンゼン環との縮合により生じる多環式ヘテロアリールであってよく、かつ部分的に飽和であってよい。 In the present invention, other substituents containing “alkyl”, “alkoxy” and “alkyl” moieties include both linear and branched types. In the present invention, “aryl” means an organic group obtained from an aromatic hydrocarbon by removing one hydrogen atom, and represents a 4-membered to 7-membered, particularly a 5-membered or 6-membered monocyclic or condensed ring. Can be included. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrycenyl, naphthacenyl, fluoranthenyl and the like. In the present invention, “heteroaryl” refers to 1 to 4 heteroatoms selected from B, N, O, S, P (═O), Si and Se as the aromatic ring skeleton atom (s). Means an aryl group in which the other remaining aromatic ring skeleton atom is carbon. It may be a 5 or 6 membered monocyclic heteroaryl, or a polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated.
ヘテロアリールには、その環の１以上のヘテロ原子が酸化されるかまたは四級化されて、例えば、Ｎ−オキシドまたは第四級塩を形成することができる２価のアリール基が挙げられる。具体的な例には、単環式ヘテロアリール、例えば、フリル、チエニル、ピロリル、イミダゾリル、ピラゾリル、チアゾリル、チアジアゾリル、イソチアゾリル、イソオキサゾリル、オキサゾリル、オキサジアゾリル、トリアジニル、テトラジニル、トリアゾリル、テトラゾリル、フラザニル、ピリジル、ピラジニル、ピリミジニル、ピリダジニルなど；多環式ヘテロアリール、例えば、ベンゾフリル、ベンゾチエニル、イソベンゾフリル、ベンゾイミダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾイソオキサゾリル、ベンゾオキサゾリル、イソインドリル、インドリル、インダゾリル、ベンゾチアジアゾリル、キノリル、イソキノリル、シンノリニル、キナゾリニル、キノリジニル、キノキサリニル、カルバゾリル、フェナントリジニル、ベンゾジオキソリルなど；並びに、そのＮ−オキシド（例えば、ピリジルＮ−オキシド、キノリルＮ−オキシドなど）、その第四級塩などが挙げられるが、これらに限定されない。 Heteroaryl includes a divalent aryl group in which one or more heteroatoms of the ring can be oxidized or quaternized to form, for example, an N-oxide or quaternary salt. Specific examples include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl , Pyrimidinyl, pyridazinyl, etc .; polycyclic heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzo Thiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolidinyl, quinoxalinyl, carbazolyl, phenane Lysinyl and benzodioxolyl; and its N- oxides (e.g., pyridyl N- oxide, quinolyl N- oxide, etc.), but such that the quaternary salts include, but are not limited to.
本発明においては、「（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、モノもしくはジ（Ｃ１−Ｃ３０）アルキルチオ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキルアミノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキルチオ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール」などのアルキル部分は１〜２０個の炭素原子、より具体的には１〜１０個の炭素原子を有することができる。「（Ｃ６−Ｃ３０）アリール、モノもしくはジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキルアミノ、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、トリ（Ｃ６−Ｃ３０）アリールシリル、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール」などのアリール部分は６〜２０個の炭素原子、より具体的には６〜１２個の炭素原子を有することができる。「（Ｃ３−Ｃ３０）ヘテロアリール」のヘテロアリールは、４〜２０個の炭素原子、より具体的には４〜１２個の炭素原子を有することができる。「（Ｃ３−Ｃ３０）シクロアルキル」のシクロアルキルは、３〜２０個の炭素原子、より具体的には３〜７個の炭素原子を有することができる。「（Ｃ３−Ｃ３０）アルキレンもしくはアルケニレン」のアルキレンもしくはアルケニレンは、３〜２０個の炭素原子、より具体的には３〜１０個の炭素原子を有することができる。 In the present invention, “(C1-C30) alkyl, (C1-C30) alkoxy, mono- or di (C1-C30) alkylthio, (C6-C30) aryl (C1-C30) alkylamino, tri (C1-C30)” Alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C1-C30) alkylthio, (C6-C30) aryl (C1-C30) alkyl, (C1-C30 Alkyl moieties such as “) alkyl (C 6 -C 30) aryl” can have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. “(C6-C30) aryl, mono- or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, di (C1-C30) alkyl (C6-C30) arylsilyl, tri ( C6-C30) arylsilyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl " The aryl moiety can have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The heteroaryl of “(C3-C30) heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The cycloalkyl of “(C 3 -C 30) cycloalkyl” can have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The alkylene or alkenylene of “(C3-C30) alkylene or alkenylene” can have 3 to 20 carbon atoms, more specifically 3 to 10 carbon atoms.
また、本発明に従う有機電界発光化合物には下記化学式２で表される化合物が挙げられる：
Ｒ５およびＲ６は独立して水素、（Ｃ６−Ｃ３０）アリールまたは（Ｃ２−Ｃ３０）ヘテロアリールを表し；
Ａｒ１〜Ａｒ４は独立して、（Ｃ６−Ｃ３０）アリール、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む（Ｃ２−Ｃ３０）ヘテロアリール、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のへテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、アダマンチル、（Ｃ７−Ｃ３０）ビシクロアルキル、または
Ｒ２１〜Ｒ２３は独立して（Ｃ１−Ｃ３０）アルキルもしくは（Ｃ６−Ｃ３０）アリールを表すか、またはＲ２２とＲ２３とは縮合環を有するかもしくは有しない（Ｃ３−Ｃ３０）アルケニレンもしくは（Ｃ３−Ｃ３０）アルキレンを介して連結されて縮合環を形成していてよく；並びに
Ｒ５およびＲ６のアリールもしくはヘテロアリール；Ａｒ１〜Ａｒ４のアリール、ヘテロアリール、ヘテロシクロアルキル、シクロアルキル、アダマンチルもしくはビシクロアルキル；Ａ１とＡ２またはＡｒ３とＡｒ４のそれぞれの連結によって形成される縮合環；並びに、Ｒ２１〜Ｒ２３のアルキルもしくはアリールは、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ１−Ｃ３０）アルキルチオ、ピペリジノ、モルホリノ、チオモルホリノ、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、ニトロ、ヒドロキシル、（Ｃ６−Ｃ３０）アリール、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１以上の置換基によってさらに置換されていてよい。
The organic electroluminescent compound according to the present invention includes a compound represented by the following chemical formula 2:
R 5 and R 6 independently represent hydrogen, (C6-C30) aryl or (C2-C30) heteroaryl;
Ar 1 to Ar 4 are independently selected from (C 2 -C 30) heteroaryl, N, O and S containing one or more heteroatoms selected from (C 6 -C 30) aryl, N, O and S 5- to 7-membered heterocycloalkyl containing one or more heteroatoms, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl, or
R 21 to R 23 independently represent (C 1 -C 30) alkyl or (C 6 -C 30) aryl, or R 22 and R 23 may or may not have a condensed ring (C 3 -C 30) alkenylene or ( C3-C30) is connected via a alkylene may form a condensed ring; and R 5 and R 6 aryl or heteroaryl; aryl Ar 1 to Ar 4, heteroaryl, heterocycloalkyl, cycloalkyl, Adamantyl or bicycloalkyl; a fused ring formed by the respective linkage of A 1 and A 2 or Ar 3 and Ar 4 ; and the alkyl or aryl of R 21 to R 23 is (C1-C30) alkyl, halo (C1 -C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkyl. 5- to 7-membered heterocycloalkyl containing one or more heteroatoms selected from thio, piperidino, morpholino, thiomorpholino, N, O and S, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxyl , (C6-C30) aryl, (C6-C30) aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl One or more selected from the group consisting of (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) arylsilyl It may be further substituted with a substituent.
また、Ａｒ１とＡｒ２、およびＡｒ３とＡｒ４がアルキレンもしくはアルケニレンを介して独立して連結される場合に形成される
から選択されるがこれらに限定されない。
Also formed when Ar 1 and Ar 2 and Ar 3 and Ar 4 are independently linked via alkylene or alkenylene.
However, it is not limited to these.
より具体的には、Ａｒ１〜Ａｒ４は独立して、下記構造：
本発明に従う有機電界発光化合物は以下の化合物として具体的に例示されうるが、本発明はこれらに限定されない：
本発明の有機電界発光化合物は以下のスキーム１に示されるように製造されうるが、これに限定されない：
第１の電極；第２の電極；並びに、前記第１の電極と第２の電極との間に設けられた１以上の有機層；を含む有機電界発光素子であって、前記有機層が化学式１の１種以上の有機電界発光化合物を含む有機電界発光素子が提供される。 A first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein the organic layer has a chemical formula An organic electroluminescent element comprising one or more organic electroluminescent compounds is provided.
有機電界発光素子においては、化学式１の１種以上の有機電界発光化合物が電界発光ドーパントとして使用される場合には、１種以上のホストを含む電解発光層を前記有機層が含む。本発明の有機電界発光素子において使用されるホストは特に限定されないが、以下の化学式３もしくは化学式４で表される化合物から選択されうる。化学式３もしくは化学式４のホスト化合物の具体的な構造は韓国特許出願第１０−２００８−００６０３９３号の＜１６２＞〜＜２１０＞に例示されているがこれらに限定されない。 In the organic electroluminescent device, when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent dopant, the organic layer includes an electroluminescent layer including one or more hosts. The host used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from compounds represented by the following chemical formula 3 or chemical formula 4. The specific structure of the host compound of Chemical Formula 3 or Chemical Formula 4 is exemplified in <162> to <210> of Korean Patent Application No. 10-2008-0060393, but is not limited thereto.
［化学式３］
（Ａｒ１１）ａ−Ｌ１−（Ａｒ１２）ｂ
［化学式４］
（Ａｒ１３）ｃ−Ｌ２−（Ａｒ１４）ｄ
式中、Ｌ１は（Ｃ６−Ｃ３０）アリーレンもしくは（Ｃ４−Ｃ３０）ヘテロアリーレンを表し；
Ｌ２はアントラセニレンを表し；
Ａｒ１１〜Ａｒ１４は独立して、水素、重水素、（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、ハロゲン、（Ｃ４−Ｃ３０）ヘテロアリール、（Ｃ５−Ｃ３０）シクロアルキルまたは（Ｃ６−Ｃ３０）アリールを表し；並びに
Ａｒ１１〜Ａｒ１４のシクロアルキル、アリールもしくはヘテロアリールは、（Ｃ６−Ｃ３０）アリールもしくは（Ｃ４−Ｃ３０）ヘテロアリール［（当該（Ｃ６−Ｃ３０）アリールもしくは（Ｃ４−Ｃ３０）ヘテロアリールは重水素、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリルおよびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１種以上の置換基を有するかもしくは有さない］、重水素、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１種以上の置換基でさらに置換されていてよく；並びに
ａ、ｂ、ｃおよびｄは独立して０〜４の整数を表す。
[Chemical formula 3]
(Ar 11 ) a -L 1- (Ar 12 ) b
[Chemical formula 4]
(Ar 13 ) c -L 2- (Ar 14 ) d
Wherein L 1 represents (C6-C30) arylene or (C4-C30) heteroarylene;
L 2 represents anthracenylene;
Ar 11 to Ar 14 are independently hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, (C4-C30) heteroaryl, (C5-C30) cycloalkyl or (C6- C30) represents aryl; and Ar 11 to Ar 14 cycloalkyl, aryl or heteroaryl is (C6-C30) aryl or (C4-C30) heteroaryl [(the (C6-C30) aryl or (C4-C30 ) Heteroaryl is deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyano, tri (C1-C30) alkylsilyl, Di (C1-C30) alkyl (C6-C30) arylsilyl and tri (C6-C30) with or without one or more substituents selected from the group consisting of arylsilyl], deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1- From C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyano, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) arylsilyl It may be further substituted with one or more substituents selected from the group consisting of; and a, b, c and d independently represent an integer of 0-4.
電界発光層は電界発光が起こる層を意味し、単一の層もしくは２以上の層が積層されている多層であってよい。本発明の構成に従ってホスト−ドーパントの混合物が使用される場合には、電界発光ホストによっては発光効率の著しい向上が確認されうる。ドーピング濃度は０．５〜１０重量％であり得る。既存の他のホスト材料と比較した場合、本発明の電界発光ホストは正孔および電子の優れた伝導性、並びに非常に優れた安定性、および著しく向上したルミネッセンス効率および駆動寿命をもたらす。よって、化学式３もしくは化学式４で表される化合物が電界発光ホストとして選択される場合には、それは本発明の化学式１で表される有機電界発光化合物の電気的不利益をかなり補うことができる。 The electroluminescent layer means a layer in which electroluminescence occurs, and may be a single layer or a multilayer in which two or more layers are laminated. When a host-dopant mixture is used according to the configuration of the present invention, a significant improvement in luminous efficiency can be observed depending on the electroluminescent host. The doping concentration can be from 0.5 to 10% by weight. When compared to other existing host materials, the electroluminescent host of the present invention provides excellent conductivity of holes and electrons, as well as very good stability, and significantly improved luminescence efficiency and drive life. Thus, when a compound represented by Formula 3 or 4 is selected as the electroluminescent host, it can significantly compensate for the electrical disadvantage of the organic electroluminescent compound represented by Formula 1 of the present invention.
有機電界発光素子は化学式１の有機電界発光化合物を含むことができ、かつアリールアミンまたはスチリルアミン化合物からなる群から選択される１種以上の化合物を含むことができる。アリールアミンまたはスチリルアミン化合物の具体的な例は、韓国特許出願第１０−２００８−００６０３９３号における＜２１２＞〜＜２２４＞に例示されているがこれに限定されない。 The organic electroluminescent device may include an organic electroluminescent compound of Formula 1, and may include one or more compounds selected from the group consisting of arylamine or styrylamine compounds. Specific examples of the arylamine or styrylamine compound are exemplified in <212> to <224> in Korean Patent Application No. 10-2008-0060393, but are not limited thereto.
また、本発明の有機電界発光素子においては、有機層は、化学式１で表される有機電界発光化合物に加えて、第１族、第２族、第４周期および第５周期遷移金属、ランタニド金属並びにｄ−遷移元素の有機金属からなる群から選択される１種以上の金属をさらに含むことができる。有機層は電界発光層および電荷発生層を含むことができる。 Moreover, in the organic electroluminescent element of the present invention, the organic layer includes, in addition to the organic electroluminescent compound represented by Chemical Formula 1, Group 1, Group 2, Group 4 and Period 5 transition metal, lanthanide metal And one or more metals selected from the group consisting of organic metals of d-transition elements. The organic layer can include an electroluminescent layer and a charge generation layer.
本発明の化学式１で表される有機電界発光化合物を含む有機電界発光素子をサブピクセルとして採用し、およびＩｒ、Ｐｔ、Ｐｄ、Ｒｈ、Ｒｅ、Ｏｓ、Ｔｌ、Ｐｂ、Ｂｉ、Ｉｎ、Ｓｎ、Ｓｂ、Ｔｅ、ＡｕおよびＡｇからなる群から選択される１種以上の金属化合物を含む１以上のサブピクセルが同時に並列にパターン形成されている、独立発光方式のピクセル構造を有する有機電界発光素子が具体化されることができる。 An organic electroluminescent device including the organic electroluminescent compound represented by Chemical Formula 1 of the present invention is employed as a subpixel, and Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb An organic electroluminescent device having a pixel structure of an independent light emitting system, in which one or more subpixels including one or more metal compounds selected from the group consisting of Te, Au, and Ag are simultaneously patterned in parallel Can be
さらに、白色発光有機電界発光素子を具体化するために、有機層は、当該有機電界発光化合物に加えて、青色、赤色もしくは緑色の光を放射する１以上の有機電界発光層を同時に含むことができる。青色、緑色もしくは赤色の光を放射する化合物は韓国特許出願第１０−２００８−０１２３２７６号、第１０−２００８−０１０７６０６号または第１０−２００８−０１１８４２８号に記載される化合物によって例示されうるが、これらに限定されない。 Furthermore, in order to embody a white light emitting organic electroluminescent device, the organic layer may include at least one organic electroluminescent layer that emits blue, red or green light in addition to the organic electroluminescent compound. it can. Compounds emitting blue, green or red light can be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, It is not limited to.
本発明の有機電界発光素子においては、電極の対のうちの一方または両方の電極の内側表面上に、カルコゲナイド（ｃｈａｌｃｏｇｅｎｉｄｅ）層、ハロゲン化金属層および金属酸化物層から選択される層（以下、「表面層」という）が配置されうる。より具体的には、電界発光媒体層のアノード表面上にケイ素またはアルミニウムのカルコゲナイド（酸化物など）層が配置されることができ、並びに電界発光媒体層のカソード表面上にハロゲン化金属層または金属酸化物層が配置されうる。それにより、駆動安定性が達成されうる。カルコゲナイドは、例えば、ＳｉＯｘ（１＝ｘ＝２）、ＡｌＯｘ（１＝ｘ＝１．５）、ＳｉＯＮ、ＳｉＡｌＯＮなどでありうる。ハロゲン化金属は、例えば、ＬｉＦ、ＭｇＦ２、ＣａＦ２、希土類金属フッ化物などでありうる。金属酸化物は、例えば、Ｃｓ２Ｏ、Ｌｉ２Ｏ、ＭｇＯ、ＳｒＯ、ＢａＯ、ＣａＯなどでありうる。 In the organic electroluminescent device of the present invention, a layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a metal oxide layer) is formed on the inner surface of one or both electrodes of the electrode pair. A “surface layer”). More specifically, a silicon or aluminum chalcogenide (such as oxide) layer can be disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal on the cathode surface of the electroluminescent medium layer. An oxide layer may be disposed. Thereby, driving stability can be achieved. The chalcogenide can be, for example, SiO x (1 = x = 2), AlO x (1 = x = 1.5), SiON, SiAlON, or the like. The metal halide can be, for example, LiF, MgF 2 , CaF 2 , rare earth metal fluoride, and the like. The metal oxide can be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.
本発明の有機電界発光素子においては、このように製造される電極の対の少なくとも一方の表面上に、電子輸送化合物と還元性ドーパントとの混合領域、または正孔輸送化合物と酸化性ドーパントとの混合領域を配置するのも好ましい。この場合には、電子輸送化合物がアニオンに還元されるので、この混合領域から電界発光媒体への電子の注入および輸送は容易になる。また、正孔輸送化合物は酸化されてカチオンになるので、この混合領域から電界発光媒体への正孔の注入および輸送は容易になる。好ましい酸化性ドーパントには様々なルイス酸およびアクセプター化合物が挙げられる。好ましい還元性ドーパントには、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、希土類金属およびこれらの混合物が挙げられる。さらに、還元性ドーパント層を電荷発生層として使用することにより、２以上の電界発光層を有する白色発光電界発光素子が製造されうる。 In the organic electroluminescence device of the present invention, a mixed region of an electron transport compound and a reducing dopant or a hole transport compound and an oxidizing dopant is formed on at least one surface of a pair of electrodes thus manufactured. It is also preferable to arrange the mixing zone. In this case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to the electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized into a cation, injection and transport of holes from the mixed region to the electroluminescent medium are facilitated. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. Furthermore, by using the reducing dopant layer as a charge generation layer, a white light emitting electroluminescent device having two or more electroluminescent layers can be manufactured.
本発明の有機電界発光化合物は青色の良好な青色発光効率および優れた寿命特性を示すので、これは非常に優れた駆動寿命を有するＯＬＥＤ素子を製造するために使用されうる。 Since the organic electroluminescent compound of the present invention exhibits good blue light emission efficiency and excellent lifetime characteristics of blue, it can be used to produce OLED devices with very good driving lifetime.
本発明の有機電界発光化合物、その製造方法、およびその化合物を使用する素子のルミネセンス特性に関して本発明がさらに説明される。しかし、以下の実施例は例示目的のためだけに提供されるのであり、以下の実施例は本発明の範囲を限定することを意図していない。 The present invention is further described with respect to the organic electroluminescent compounds of the present invention, the process for their production, and the luminescence properties of devices using the compounds. However, the following examples are provided for illustrative purposes only, and the following examples are not intended to limit the scope of the invention.
［製造例１］化合物６８の製造
化合物Ｂの製造
化合物Ａ（２０ｇ、９６．０５ｍｍｏｌ）、ベンゾイルペルオキシド（３．１ｇ、９．６０ｍｍｏｌ、７５％）、ニトロベンゼン（３００ｍＬ）およびＢｒ２（１０．８５ｍＬ、２１１．３ｍｍｏｌ）が室温で混合され、１２０℃に加熱され、３時間後に、この混合物は室温に冷却され、ＫＯＨ溶液で中和され、そして塩化メチレン（ＭＣ）で抽出された。減圧下で蒸留した後で、得られた固体を酢酸エチル（ＥＡ）で再結晶化させることにより、化合物Ｂ（２０ｇ、５６．９２％）が得られた。
Preparation of Compound B Compound A (20 g, 96.05 mmol), benzoyl peroxide (3.1 g, 9.60 mmol, 75%), nitrobenzene (300 mL) and Br 2 (10.85 mL, 211.3 mmol) were mixed at room temperature. , Heated to 120 ° C., and after 3 hours, the mixture was cooled to room temperature, neutralized with KOH solution, and extracted with methylene chloride (MC). After distillation under reduced pressure, the resulting solid was recrystallized with ethyl acetate (EA) to give Compound B (20 g, 56.92%).
化合物Ｃの製造
２−ブロモナフタレン（２５．４ｇ、１２２．９５ｍｍｏｌ）がＴＨＦ（１０００ｍＬ）中に溶解させられ、そしてｎ−ＢｕＬｉ（１１４．７ｍｍｏｌ、ヘキサン中２．５Ｍ）が−７８℃でゆっくりと添加された。３０分後に、この混合物は室温で攪拌された。３０分後に、化合物Ｂ（１４．１ｇ、４０ｍｍｏｌ）がこの混合物に添加された。この混合物は１２時間にわたって攪拌され、そして蒸留水およびＭＣで抽出された。有機相をＭｇＳＯ４で乾燥させ、そして減圧下で蒸留によって溶媒を除去した後で、カラム分離（ＭＣ：ヘキサン＝１：１）によって化合物Ｃが得られた。
Preparation of Compound C 2-Bromonaphthalene (25.4 g, 122.95 mmol) was dissolved in THF (1000 mL) and n-BuLi (114.7 mmol, 2.5 M in hexane) was slowly added at -78 ° C. Added. After 30 minutes, the mixture was stirred at room temperature. After 30 minutes, Compound B (14.1 g, 40 mmol) was added to the mixture. The mixture was stirred for 12 hours and extracted with distilled water and MC. After the organic phase was dried over MgSO 4 and the solvent was removed by distillation under reduced pressure, Compound C was obtained by column separation (MC: hexane = 1: 1).
化合物Ｄの製造
化合物Ｃ（１０ｇ、１６．０６ｍｍｏｌ）が酢酸（５００ｍＬ）に添加され、そしてこの混合物は１３０℃に加熱された。Ｚｎ（２０．２ｇ）がこの混合物にゆっくりと添加され、次いでこれにＨＣｌ（２０ｍＬ）がゆっくりと添加された。３０分後、Ｚｎ（１０ｇ）がこの混合物に添加され、次いでＨＣｌ（１０ｍＬ）がさらにこれに添加された。この混合物を還流下で１２時間にわたって攪拌した後で、この混合物は室温まで冷却された。蒸留水を添加することにより生じた固体が減圧下でろ過された。得られた固体はＮａＯＨ溶液で洗浄され、カラム分離によって精製されて、化合物Ｄ（６．５ｇ、１１．０４ｍｍｏｌ、６８．７４％）を得た。
Preparation of Compound D Compound C (10 g, 16.06 mmol) was added to acetic acid (500 mL) and the mixture was heated to 130 ° C. Zn (20.2 g) was slowly added to the mixture, and then HCl (20 mL) was slowly added thereto. After 30 minutes, Zn (10 g) was added to the mixture, and then HCl (10 mL) was further added thereto. After stirring the mixture at reflux for 12 hours, the mixture was cooled to room temperature. The solid produced by adding distilled water was filtered under reduced pressure. The resulting solid was washed with NaOH solution and purified by column separation to give compound D (6.5 g, 11.04 mmol, 68.74%).
化合物６８の製造
化合物Ｄ（５ｇ、８．４９ｍｍｏｌ）、ジフェニルアミン（３．７ｇ、２２．０９ｍｍｏｌ）、Ｐｄ（ＯＡｃ）２（０．０９ｇ、０．４２ｍｍｏｌ）、およびＮａＯｔ−ｂｕ（３．２６ｇ、３３．９９ｍｍｏｌ）が添加された。トルエン（２００ｍＬ）およびＰ（ｔ−ｂｕ）３（０．５０ｍＬ、１．０１９ｍｍｏｌ、５０％収率）が窒素雰囲気でこの混合物に添加された。この混合物は還流下で攪拌された。この混合物を１２時間にわたって攪拌した後で、この混合物は室温まで冷却され、そして蒸留水およびＭＣで抽出された。有機相をＭｇＳＯ４で乾燥させ、そして減圧下で蒸留によって溶媒を除去した後で、カラム分離によって化合物６８（２．９ｇ、７５．８％）が得られた。
Preparation of Compound 68 Compound D (5 g, 8.49 mmol), diphenylamine (3.7 g, 22.09 mmol), Pd (OAc) 2 (0.09 g, 0.42 mmol), and NaOt-bu (3.26 g, 33). .99 mmol) was added. Toluene (200 mL) and P (t-bu) 3 (0.50 mL, 1.019 mmol, 50% yield) were added to the mixture under a nitrogen atmosphere. This mixture was stirred under reflux. After stirring the mixture for 12 hours, the mixture was cooled to room temperature and extracted with distilled water and MC. After the organic phase was dried over MgSO 4 and the solvent was removed by distillation under reduced pressure, column separation gave compound 68 (2.9 g, 75.8%).
１Ｈ ＮＭＲ（ＣＤＣｌ３、２００ＭＨｚ）：ｄ＝６．６３（８Ｈ，ｍ）、６．８１（４Ｈ，ｍ）、７．０２（２Ｈ，ｍ）、７．２（８Ｈ，ｍ）、７．５８〜７．５９（６Ｈ，ｍ）、７．７３（２Ｈ，ｍ）、７．８７〜７．９２（４Ｈ，ｍ）、８（４Ｈ，ｍ）、８．１３（２Ｈ，ｍ）。ＭＳ／ＦＡＢ：７６４．９６（実測値）、７６４．３２（計算値）。 1 H NMR (CDCl 3 , 200 MHz): d = 6.63 (8H, m), 6.81 (4H, m), 7.02 (2H, m), 7.2 (8H, m), 7. 58-7.59 (6H, m), 7.73 (2H, m), 7.87-7.92 (4H, m), 8 (4H, m), 8.13 (2H, m). MS / FAB: 764.96 (actual value), 764.32 (calculated value).
製造例１の手順に従って有機電界発光化合物１〜６７が製造された。表１は製造された有機電界発光化合物の１Ｈ ＮＭＲおよびＭＳ／ＦＡＢを示す。 Organic electroluminescent compounds 1 to 67 were produced according to the procedure of Production Example 1. Table 1 shows the 1 H NMR and MS / FAB of the prepared organic electroluminescent compounds.
［実施例１〜３］
本発明の有機電界発光化合物を使用するＯＬＥＤ素子の製造
本発明の電界発光材料を使用してＯＬＥＤ素子が製造された。まず、ＯＬＥＤ用ガラス（サムスンコーニングにより製造）から得られた透明電極ＩＴＯ薄膜（１５Ω／□）を、トリクロロエチレン、アセトン、エタノールおよび蒸留水を順に使用した超音波洗浄にかけ、使用するまでイソプロパノール中に貯蔵した。次に、真空蒸着装置の基体ホルダにＩＴＯ基体を取り付け、この真空蒸着装置のセル内に４，４’，４”−トリス（Ｎ，Ｎ−（２−ナフチル）−フェニルアミノ）トリフェニルアミン（２−ＴＮＡＴＡ）を入れ、このセルはチャンバー内で１０−６ｔｏｒｒの真空まで通気された。次いで、このセルに電流を適用して、２−ＴＮＡＴＡを蒸発させて、それにより、ＩＴＯ基体上に６０ｎｍの厚みを有する正孔注入層を形成した。
[Examples 1 to 3]
Production of OLED Element Using Organic Electroluminescent Compound of the Invention An OLED element was produced using the electroluminescent material of the invention. First, transparent electrode ITO thin film (15Ω / □) obtained from glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water in order, and stored in isopropanol until used did. Next, an ITO substrate is attached to the substrate holder of the vacuum deposition apparatus, and 4,4 ′, 4 ″ -tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( The cell was vented to a vacuum of 10 −6 torr in the chamber, and an electric current was then applied to the cell to evaporate the 2-TNATA and thereby onto the ITO substrate A hole injection layer having a thickness of 60 nm was formed.
次いで、真空蒸着装置の他のセルにＮ，Ｎ’−ビス（α−ナフチル）−Ｎ，Ｎ’−ジフェニル−４，４’−ジアミン（ＮＰＢ）を入れ、このセルに電流を適用してＮＰＢを蒸発させて、それにより正孔注入層上に２０ｎｍの厚みを有する正孔輸送層を形成した。 Next, N, N′-bis (α-naphthyl) -N, N′-diphenyl-4,4′-diamine (NPB) is placed in another cell of the vacuum deposition apparatus, and an electric current is applied to this cell to apply NPB. Was evaporated, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
正孔注入層および正孔輸送層を形成した後で、この形成された層上に電界発光層が蒸着させられた。下記構造のＤＮＡ（実施例１〜３）が真空蒸着装置の１つのセルに入れられ、本発明の化合物が別のセルに入れられた。次いで、正孔輸送層上に、１００：３の堆積割合で、３０ｎｍの厚さを有する電界発光層を蒸着させた。 After forming the hole injection layer and the hole transport layer, an electroluminescent layer was deposited on the formed layer. DNA having the following structure (Examples 1 to 3) was placed in one cell of a vacuum deposition apparatus, and the compound of the present invention was placed in another cell. Next, an electroluminescent layer having a thickness of 30 nm was deposited on the hole transport layer at a deposition ratio of 100: 3.
次いで、電界発光層上に、電子輸送層としてトリス（８−ヒドロキシキノリン）−アルミニウム（ＩＩＩ）（Ａｌｑ）を２０ｎｍの厚さで蒸着させた。次いで、リチウムキノラート（Ｌｉｑ）を電子注入層として１〜２ｎｍの厚みで蒸着させた後で、別の真空蒸着装置を使用して、１５０ｎｍの厚みを有するＡｌカソードが形成されて、ＯＬＥＤを製造した。 Next, tris (8-hydroxyquinoline) -aluminum (III) (Alq) was deposited as an electron transport layer on the electroluminescent layer to a thickness of 20 nm. Next, after depositing lithium quinolate (Liq) as an electron injection layer to a thickness of 1-2 nm, an Al cathode having a thickness of 150 nm is formed using another vacuum deposition apparatus to produce an OLED. did.
ＯＬＥＤ素子において電界発光材料として使用された各化合物は１０−６ｔｏｒｒでの真空昇華によって精製された。 Each compound used as an electroluminescent material in the OLED device was purified by vacuum sublimation at 10 −6 torr.
実施例１〜３における本発明の有機電界発光化合物を含むＯＬＥＤの発光効率はそれぞれ１，０００ｃｄ／ｍ２で測定され、結果は表２に示される。 The luminous efficiencies of the OLEDs containing the organic electroluminescent compounds of the present invention in Examples 1 to 3 were each measured at 1,000 cd / m 2 and the results are shown in Table 2.
表２に認められるように、本発明の有機電界発光化合物は濃青色を生じさせる。すなわち、有機電界発光ディスプレイにおけるＮＴＳＣ標準に近い色を実現するのに青色が必要とされる場合に、本発明の有機電界発光化合物が有用であり得る。フェナンスレン誘導体が高いガラス転移温度を有するので、優れた熱安定性が必要とされる。上述のように、高い純度を有する青色発光材料として、本発明の有機電界発光化合物が使用される。 As can be seen in Table 2, the organic electroluminescent compounds of the present invention produce a deep blue color. That is, the organic electroluminescent compounds of the present invention can be useful when blue is required to achieve a color close to the NTSC standard in organic electroluminescent displays. Since phenanthrene derivatives have a high glass transition temperature, excellent thermal stability is required. As described above, the organic electroluminescent compound of the present invention is used as a blue light-emitting material having high purity.
本発明の有機電界発光化合物は青色での良好な発光効率および優れた寿命特性を示すので、それは非常に優れた駆動寿命を有するＯＬＥＤ素子を製造するために使用されうる。 Since the organic electroluminescent compound of the present invention exhibits good luminous efficiency in blue and excellent lifetime characteristics, it can be used to produce OLED devices with very good driving lifetime.
Claims (8)
Ａｒ１〜Ａｒ４は独立して、（Ｃ６−Ｃ３０）アリールを表し；
Ｒ１〜Ｒ ４ およびＲ１１〜Ｒ１３は独立して、水素、（Ｃ１−Ｃ３０）アルキル、（Ｃ３−Ｃ３０）シクロアルキル、（Ｃ６−Ｃ３０）アリール、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ６−Ｃ６０）アリールオキシ、モノもしくはジ（Ｃ１−Ｃ３０）アルキルアミノ、モノもしくはジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキルアミノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、またはトリ（Ｃ６−Ｃ３０）アリールシリルを表し；
Ｒ ５ 〜Ｒ ６ は独立して（Ｃ６−Ｃ３０）アリールまたは（Ｃ２−Ｃ３０）ヘテロアリールを表し；並びに
Ｒ１〜Ｒ６のアルキル、シクロアルキル、アリールもしくは、ヘテロアリール、アルコキシ、アリールオキシ、アルキルアミノ、アリールアミノ、アリールアルキルアミノ、トリアルキルシリル、ジアルキルアリールシリルもしくはトリアリールシリル；並びにＡｒ１〜Ａｒ４のアリールは、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ１−Ｃ３０）アルキルチオ、ピペリジノ、モルホリノ、チオモルホリノ、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、ニトロ、ヒドロキシル、（Ｃ６−Ｃ３０）アリール、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１以上の置換基によってさらに置換されていてよい。 Organic electroluminescent compound used as a blue electroluminescent material represented by Chemical Formula 1:
Ar 1 to Ar 4 is independently and display the (C6-C30) aryl;
R 1 to R 4 and R 11 to R 13 are independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1 -C30) alkoxy, (C6-C60) aryloxy, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, tri Represents (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, or tri (C6-C30) arylsilyl;
R 5 to R 6 independently represent (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; and R 1 to R 6 alkyl, cycloalkyl, aryl or heteroaryl, alkoxy, aryloxy, alkyl amino, arylamino, arylalkylamino, trialkylsilyl, dialkyl aryl silyl or triarylsilyl; aryl and Ar 1 to Ar 4 is, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30 ) Alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatoms selected from N, O and S, (C3-C30) cycloalkyl Halogen, cyano, nitro, hydro Sil, (C6-C30) aryl, (C6-C30) aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) One or more selected from the group consisting of alkyl (C6-C30) aryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) arylsilyl It may be further substituted with a substituent.
Ｒ５およびＲ６は独立して（Ｃ６−Ｃ３０）アリールまたは（Ｃ２−Ｃ３０）ヘテロアリールを表し；
Ａｒ１〜Ａｒ４は独立して、（Ｃ６−Ｃ３０）アリールを表し；並びに
Ｒ５およびＲ６のアリールもしくはヘテロアリール；並びにＡｒ１〜Ａｒ４のアリールは、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ１−Ｃ３０）アルキルチオ、ピペリジノ、モルホリノ、チオモルホリノ、Ｎ、ＯおよびＳから選択される１以上のヘテロ原子を含む５員〜７員のヘテロシクロアルキル、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、ニトロ、ヒドロキシル、（Ｃ６−Ｃ３０）アリール、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、（Ｃ２−Ｃ３０）ヘテロアリール、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１以上の置換基によってさらに置換されていてよい。 The organic electroluminescent compound according to claim 1, represented by Chemical Formula 2:
R 5 and R 6 independently represent ( C6-C30) aryl or (C2-C30) heteroaryl;
Ar 1 to Ar 4 is independently, (C6-C30) aryl was tables; <br/> to the parallel beauty R 5 and the aryl or heteroaryl of R 6; aryl and Ar 1 to Ar 4 is, (C1- 5 containing one or more heteroatoms selected from C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomorpholino, N, O and S Membered to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30) aryl, (C6-C30) aryloxy, (C6-C30) arylthio, (C2- C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C One or more substituents selected from the group consisting of -C30) aryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) arylsilyl May be further substituted by.
前記有機層が１種以上の有機電界発光化合物と、化学式３または化学式４：
（［化学式３］
（Ａｒ１１）ａ−Ｌ１−（Ａｒ１２）ｂ
［化学式４］
（Ａｒ１３）ｃ−Ｌ２−（Ａｒ１４）ｄ
式中、Ｌ１は（Ｃ６−Ｃ３０）アリーレンもしくは（Ｃ４−Ｃ３０）ヘテロアリーレンを表し；
Ｌ２はアントラセニレンを表し；
Ａｒ１１〜Ａｒ１４は独立して、水素、重水素、（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、ハロゲン、（Ｃ４−Ｃ３０）ヘテロアリール、（Ｃ５−Ｃ３０）シクロアルキルまたは（Ｃ６−Ｃ３０）アリールを表し；並びに
Ａｒ１１〜Ａｒ１４のシクロアルキル、アリールもしくはヘテロアリールは、（Ｃ６−Ｃ３０）アリールもしくは（Ｃ４−Ｃ３０）ヘテロアリール［（当該（Ｃ６−Ｃ３０）アリールもしくは（Ｃ４−Ｃ３０）ヘテロアリールは重水素、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリルおよびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１種以上の置換基を有するかもしくは有さない］、重水素、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ３−Ｃ３０）シクロアルキル、ハロゲン、シアノ、トリ（Ｃ１−Ｃ３０）アルキルシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、およびトリ（Ｃ６−Ｃ３０）アリールシリルからなる群から選択される１種以上の置換基でさらに置換されていてよく；並びに
ａ、ｂ、ｃおよびｄは独立して１〜４の整数を表す）
で表される１種以上のホスト化合物とを含む、
請求項４に記載の有機電界発光素子。 A first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode;
The organic layer comprises one or more organic electroluminescent compounds and Chemical Formula 3 or Chemical Formula 4:
([Chemical Formula 3]
(Ar 11 ) a -L 1- (Ar 12 ) b
[Chemical formula 4]
(Ar 13 ) c -L 2- (Ar 14 ) d
Wherein L 1 represents (C6-C30) arylene or (C4-C30) heteroarylene;
L 2 represents anthracenylene;
Ar 11 to Ar 14 are independently hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, (C4-C30) heteroaryl, (C5-C30) cycloalkyl or (C6- C30) represents aryl; and Ar 11 to Ar 14 cycloalkyl, aryl or heteroaryl is (C6-C30) aryl or (C4-C30) heteroaryl [(the (C6-C30) aryl or (C4-C30 ) Heteroaryl is deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyano, tri (C1-C30) alkylsilyl, Di (C1-C30) alkyl (C6-C30) arylsilyl and tri (C6-C30) with or without one or more substituents selected from the group consisting of arylsilyl], deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1- From C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyano, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, and tri (C6-C30) arylsilyl And may be further substituted with one or more substituents selected from the group consisting of; and a, b, c and d independently represent an integer of 1 to 4)
Including one or more host compounds represented by:
The organic electroluminescent element according to claim 4 .
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020100040610A KR20110121147A (en) | 2010-04-30 | 2010-04-30 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR10-2010-0040610 | 2010-04-30 | ||
| PCT/KR2011/002526 WO2011136484A1 (en) | 2010-04-30 | 2011-04-11 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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| JP2013530513A JP2013530513A (en) | 2013-07-25 |
| JP5782503B2 true JP5782503B2 (en) | 2015-09-24 |
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| JP (1) | JP5782503B2 (en) |
| KR (1) | KR20110121147A (en) |
| CN (1) | CN102958906B (en) |
| TW (1) | TW201213308A (en) |
| WO (1) | WO2011136484A1 (en) |
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| US9065060B2 (en) | 2011-01-17 | 2015-06-23 | Lg Chem, Ltd. | Compound and organic light-emitting device comprising same |
| KR101896063B1 (en) * | 2012-03-13 | 2018-09-07 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| US9666812B2 (en) * | 2012-04-13 | 2017-05-30 | Lg Chem, Ltd. | Nitrogen-containing heterocyclic compound and organic electronic device using same |
| DE102012011335A1 (en) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Connections for Organic Electronic Devices |
| EP2869356B1 (en) | 2012-06-28 | 2016-10-12 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescence element and material for organic electroluminescence element |
| KR102143742B1 (en) | 2012-09-04 | 2020-08-12 | 메르크 파텐트 게엠베하 | Connections for electronic devices |
| TWI482759B (en) | 2013-02-07 | 2015-05-01 | Lg Chemical Ltd | Heterocyclic compound and organic light emitting device using the same |
| US8927749B2 (en) | 2013-03-07 | 2015-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102105076B1 (en) * | 2013-06-04 | 2020-04-28 | 삼성디스플레이 주식회사 | Condensed cyclic compound and organic light-emitting diode comprising the same |
| US10158083B2 (en) | 2013-12-12 | 2018-12-18 | Merck Patent Gmbh | Materials for electronic devices |
| EP3114102B1 (en) * | 2014-03-07 | 2017-12-06 | Merck Patent GmbH | Materials for electronic devices |
| KR102291487B1 (en) * | 2014-12-10 | 2021-08-20 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| KR101837804B1 (en) * | 2015-02-16 | 2018-03-12 | 주식회사 엘지화학 | Double spiro structure compound and organic light emitting device comprising the same |
| KR101826427B1 (en) | 2015-06-05 | 2018-02-06 | 주식회사 엘지화학 | Organic compound having double spiro structure and organic electronic device comprising the same |
| TWI560171B (en) * | 2015-10-16 | 2016-12-01 | Tetrahedron Technology Corp | Organic electroluminescent devices and material thereof |
| KR20180037645A (en) * | 2016-10-04 | 2018-04-13 | 삼성디스플레이 주식회사 | Polycyclic compound and organic electroluminescence device including the same |
| KR102259334B1 (en) | 2016-11-23 | 2021-05-31 | 주식회사 엘지화학 | Electroactive compound |
| WO2020080849A1 (en) * | 2018-10-17 | 2020-04-23 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
| CN110105262A (en) * | 2019-04-29 | 2019-08-09 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence molecular material and its synthetic method, organic electroluminescence device |
| US11613530B2 (en) | 2019-04-29 | 2023-03-28 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Thermally activated delayed fluorescent molecular material, method for synthesizing the same, and organic electroluminescent device |
| CN114075112B (en) * | 2020-08-14 | 2023-12-01 | 广州华睿光电材料有限公司 | Fluorene compound and application thereof |
| CN112939788A (en) * | 2021-03-01 | 2021-06-11 | 浙江虹舞科技有限公司 | Amantadine compound, application thereof and organic electroluminescent device containing amantadine compound |
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| JPH07287408A (en) * | 1994-04-20 | 1995-10-31 | Minolta Co Ltd | Electrophotographic photoreceptor using novel diamino compound |
| JP3915256B2 (en) * | 1998-06-29 | 2007-05-16 | 東洋インキ製造株式会社 | Organic electroluminescent device material and organic electroluminescent device using the same |
| JP2005005226A (en) * | 2003-06-16 | 2005-01-06 | Sony Corp | Organic electroluminescent element |
| CN1934906A (en) * | 2004-03-19 | 2007-03-21 | 出光兴产株式会社 | organic electroluminescent element |
| JP4377783B2 (en) * | 2004-09-14 | 2009-12-02 | 三井化学株式会社 | Triarylamine compound and organic electroluminescent device containing the triarylamine compound |
| US20060088728A1 (en) * | 2004-10-22 | 2006-04-27 | Raymond Kwong | Arylcarbazoles as hosts in PHOLEDs |
| CN100514194C (en) * | 2005-01-18 | 2009-07-15 | 京瓷美达株式会社 | Single layer type electrophotographic photoconductor and image forming device |
| US7807275B2 (en) * | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
| JP4848152B2 (en) * | 2005-08-08 | 2011-12-28 | 出光興産株式会社 | Aromatic amine derivative and organic electroluminescence device using the same |
| WO2007063986A1 (en) * | 2005-12-02 | 2007-06-07 | Toyo Ink Manufacturing Co., Ltd. | Diaminoarylene compound having carbazolyl group and use thereof |
| CN101321728A (en) * | 2005-12-02 | 2008-12-10 | 东洋油墨制造株式会社 | Diaminoarylene compound having carbazolyl group and use thereof |
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| CN102958906A (en) | 2013-03-06 |
| KR20110121147A (en) | 2011-11-07 |
| JP2013530513A (en) | 2013-07-25 |
| CN102958906B (en) | 2015-11-25 |
| TW201213308A (en) | 2012-04-01 |
| WO2011136484A1 (en) | 2011-11-03 |
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