WO2010110554A2 - Organic electroluminescent device using organic electroluminescent compounds - Google Patents
Organic electroluminescent device using organic electroluminescent compounds Download PDFInfo
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- WO2010110554A2 WO2010110554A2 PCT/KR2010/001692 KR2010001692W WO2010110554A2 WO 2010110554 A2 WO2010110554 A2 WO 2010110554A2 KR 2010001692 W KR2010001692 W KR 2010001692W WO 2010110554 A2 WO2010110554 A2 WO 2010110554A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- compound
- mmol
- chemical formula
- heteroaryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 239000010410 layer Substances 0.000 claims abstract description 58
- 239000012044 organic layer Substances 0.000 claims abstract description 19
- 239000002019 doping agent Substances 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims description 39
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 19
- -1 stilbenylene Chemical group 0.000 claims description 19
- 125000006749 (C6-C60) aryl 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 6
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004653 anthracenylene group Chemical group 0.000 claims description 5
- 125000005584 chrysenylene group Chemical group 0.000 claims description 5
- 125000005548 pyrenylene group Chemical group 0.000 claims description 5
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 4
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000006759 (C2-C60) alkenylene group Chemical group 0.000 claims description 3
- 125000006760 (C2-C60) alkynylene group Chemical group 0.000 claims description 3
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 3
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 3
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 230000002829 reductive effect Effects 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000012153 distilled water Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000001816 cooling Methods 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000000605 extraction Methods 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000001771 vacuum deposition Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229940125851 compound 27 Drugs 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 3
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 3
- 0 Brc1ccc(CO*2)c2c1 Chemical compound Brc1ccc(CO*2)c2c1 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125833 compound 23 Drugs 0.000 description 3
- 229940125878 compound 36 Drugs 0.000 description 3
- 229940125844 compound 46 Drugs 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
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- CMIMBQIBIZZZHQ-UHFFFAOYSA-N 1-bromo-2-methylnaphthalene Chemical compound C1=CC=CC2=C(Br)C(C)=CC=C21 CMIMBQIBIZZZHQ-UHFFFAOYSA-N 0.000 description 2
- BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 239000011777 magnesium Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- GOFLEYUWXFJWHT-UHFFFAOYSA-N Bc1cccc2cc3ccccc3cc12 Chemical compound Bc1cccc2cc3ccccc3cc12 GOFLEYUWXFJWHT-UHFFFAOYSA-N 0.000 description 1
- DXELCDIBAJCKEI-UHFFFAOYSA-N Brc1cc2ccccc2c2c1CCC=C2 Chemical compound Brc1cc2ccccc2c2c1CCC=C2 DXELCDIBAJCKEI-UHFFFAOYSA-N 0.000 description 1
- YLUIFQLBXRJTTA-UHFFFAOYSA-N CC(C)(c1c-2cccc1)c(cc1)c-2c2c1c(C1=CCCC=C1)c(cccc1)c1c2-c1ccccc1 Chemical compound CC(C)(c1c-2cccc1)c(cc1)c-2c2c1c(C1=CCCC=C1)c(cccc1)c1c2-c1ccccc1 YLUIFQLBXRJTTA-UHFFFAOYSA-N 0.000 description 1
- XJTCZQUCLPNGJR-UHFFFAOYSA-N CC(C)(c1ccccc1-1)c2c-1c1cc(cccc3)c3cc1cc2 Chemical compound CC(C)(c1ccccc1-1)c2c-1c1cc(cccc3)c3cc1cc2 XJTCZQUCLPNGJR-UHFFFAOYSA-N 0.000 description 1
- KLWUOEYBHADGSK-UHFFFAOYSA-N CC(C)(c1ccccc1-c1c2)c1cc1c2c(-c2cc(cccc3)c3cc2)c(cccc2)c2c1-c1cc2ccccc2cc1 Chemical compound CC(C)(c1ccccc1-c1c2)c1cc1c2c(-c2cc(cccc3)c3cc2)c(cccc2)c2c1-c1cc2ccccc2cc1 KLWUOEYBHADGSK-UHFFFAOYSA-N 0.000 description 1
- DDNWNYGSERHMGA-UHFFFAOYSA-N CC(C)(c1ccccc11)C(C=CC2=C(C3(C)C4=CC=CC3)Br)=C1C2=C4Br Chemical compound CC(C)(c1ccccc11)C(C=CC2=C(C3(C)C4=CC=CC3)Br)=C1C2=C4Br DDNWNYGSERHMGA-UHFFFAOYSA-N 0.000 description 1
- PAXJATBLSSJGCP-UHFFFAOYSA-N CC(C)(c1ccccc1C1=CC=CC2(C)C1=Cc1ccccc1C2)O Chemical compound CC(C)(c1ccccc1C1=CC=CC2(C)C1=Cc1ccccc1C2)O PAXJATBLSSJGCP-UHFFFAOYSA-N 0.000 description 1
- FGKRHLLDNMHHSI-UHFFFAOYSA-N CC(C1)C(Br)=CC(C2c3cc4ccccc4cc3)=C1C(c1cc(cccc3)c3cc1)c1c2c2ccccc2c2ccccc12 Chemical compound CC(C1)C(Br)=CC(C2c3cc4ccccc4cc3)=C1C(c1cc(cccc3)c3cc1)c1c2c2ccccc2c2ccccc12 FGKRHLLDNMHHSI-UHFFFAOYSA-N 0.000 description 1
- GPAKVSWOKIQZTB-UHFFFAOYSA-N CC(C1)Cc2cc(cccc3)c3cc2C1Br Chemical compound CC(C1)Cc2cc(cccc3)c3cc2C1Br GPAKVSWOKIQZTB-UHFFFAOYSA-N 0.000 description 1
- ORNYWKQDBZWVFL-UHFFFAOYSA-N CC(CC(C(c1ccccc11)=O)=C2C1=O)C=C2Br Chemical compound CC(CC(C(c1ccccc11)=O)=C2C1=O)C=C2Br ORNYWKQDBZWVFL-UHFFFAOYSA-N 0.000 description 1
- RLBDRLHYLBNLSZ-UHFFFAOYSA-N CC1(C)c(cc(c(C(c2c3cccc2)=O)c2)C3=O)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(c(C(c2c3cccc2)=O)c2)C3=O)c2-c2c1cccc2 RLBDRLHYLBNLSZ-UHFFFAOYSA-N 0.000 description 1
- WOELIHBZXJUNGO-UHFFFAOYSA-N CC1(C)c2cc(C(c(cccc3)c3C(O)=O)=O)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(C(c(cccc3)c3C(O)=O)=O)ccc2-c2ccccc12 WOELIHBZXJUNGO-UHFFFAOYSA-N 0.000 description 1
- IABGHFBNLPQDOT-UHFFFAOYSA-N CC1(C)c2cc3c(-c(cc4c5c(cccc6)c6ccc55)ccc4[n]5-c4ccccc4)c(cccc4)c4c(-c(cc4)cc(c5c6ccc7c5cccc7)c4[n]6-c4ccccc4)c3cc2-c2ccccc12 Chemical compound CC1(C)c2cc3c(-c(cc4c5c(cccc6)c6ccc55)ccc4[n]5-c4ccccc4)c(cccc4)c4c(-c(cc4)cc(c5c6ccc7c5cccc7)c4[n]6-c4ccccc4)c3cc2-c2ccccc12 IABGHFBNLPQDOT-UHFFFAOYSA-N 0.000 description 1
- UJVQZZSMKJJHSZ-UHFFFAOYSA-N CC1C=Cc2ccc(C(c3ccccc3C(c3cc4ccccc4cc3)(c3c4)O)(c3cc3c4-c4ccccc4C3(C)C)O)cc2C1 Chemical compound CC1C=Cc2ccc(C(c3ccccc3C(c3cc4ccccc4cc3)(c3c4)O)(c3cc3c4-c4ccccc4C3(C)C)O)cc2C1 UJVQZZSMKJJHSZ-UHFFFAOYSA-N 0.000 description 1
- DAUCSGSCDZOKLE-UHFFFAOYSA-N COC(c(ccc1c2cccc1)c2Br)=O Chemical compound COC(c(ccc1c2cccc1)c2Br)=O DAUCSGSCDZOKLE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 229910003953 H3PO2 Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- QETCHUQABIWNKP-UHFFFAOYSA-N OC(c(cc(cc1)Br)c1C(c1c(cccc2)c2c(cccc2)c2c1)=O)=O Chemical compound OC(c(cc(cc1)Br)c1C(c1c(cccc2)c2c(cccc2)c2c1)=O)=O QETCHUQABIWNKP-UHFFFAOYSA-N 0.000 description 1
- VUVIRKAVBZITDO-UHFFFAOYSA-N OC(c(ccc1c2cccc1)c2Br)=O Chemical compound OC(c(ccc1c2cccc1)c2Br)=O VUVIRKAVBZITDO-UHFFFAOYSA-N 0.000 description 1
- PAOVZAAPVZTNKM-UHFFFAOYSA-N OC(c1ccc(cccc2)c2c1)(c1cc(Br)ccc1C1(C2=CC3C=CC=CC3C=C2)O)c2c1c1ccccc1c1ccccc21 Chemical compound OC(c1ccc(cccc2)c2c1)(c1cc(Br)ccc1C1(C2=CC3C=CC=CC3C=C2)O)c2c1c1ccccc1c1ccccc21 PAOVZAAPVZTNKM-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 125000004414 alkyl thio group Chemical group 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
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 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
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- UCEZVTFDWHRKPV-UHFFFAOYSA-N c(cc1)cc2c1cc(C1c3c(cccc4)c4c(cccc4)c4c3C(c3cc(cccc4)c4cc3)c3cc(-c4cc5ccccc5cc4)ccc13)cc2 Chemical compound c(cc1)cc2c1cc(C1c3c(cccc4)c4c(cccc4)c4c3C(c3cc(cccc4)c4cc3)c3cc(-c4cc5ccccc5cc4)ccc13)cc2 UCEZVTFDWHRKPV-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- 125000004306 triazinyl group Chemical group 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
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
Definitions
- the present invention relates to an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) represented by Chemical Formula 1 and one or more dopant compound(s) represented by Chemical Formula 2:
- ring A represents a fused aromatic ring formed as two or more rings are fused, excluding the case where the ring A is benzanthracene or tetracene; [6] [Chemical Formula 2]
- L represents anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, (C2-C60)alkenylene or (C2-C60)alkynylene.
- electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
- EL electroluminescent
- Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
- an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and emit light as the electron-hole pair is extinguished.
- the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since the organic EL device may exhibit green, blue and red colors, it is drawing a lot of attentions as a full-color display device of the next generation.
- electroluminescent material In an organic EL device, the most important factor that determines its performance including luminous efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
- the organic EL device commonly has a configuration of anode/
- HIL/HTL/EML/ETL/EIL/cathode Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the electroluminescent layer (EML).
- EML electroluminescent layer
- the inventors of the present invention have made efforts to solve the aforesaid problem. As a result, they have invented an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, the organic layer including an electroluminescent layer containing a combination of specific compounds, in order to provide an organic electroluminescent device exhibiting high color purity, high brightness and long operation life.
- an object of the present invention is to provide an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) and one or more dopant compound(s), the organic electroluminescent device having excellent luminous efficiency, superior color purity, low driving voltage and good operation life.
- the present invention provides an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) represented by Chemical Formula 1 and one or more dopant compound(s) represented by Chemical Formula 2:
- ring A represents a fused aromatic ring formed as two or more rings are fused, except for the case where the ring A is benzanthracene or tetracene;
- Ri through R 6 independently represent hydrogen, deuterium, (Cl-C60)alkyl,
- each of Ri through R 6 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring;
- the fused aromatic ring of the ring A, and the alkyl, alkoxy, aryl, heteroaryl, alkenyl or alkynyl of Ri through R 6 , or the fused ring formed as each of them is linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring may be further substituted by hydrogen, deuterium, (Cl-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, (C3-C60)alkenyl, (C3-C60)alkynyl or cyano, wherein the substituent further substituted at the ring A, Ri through R 6 or the fused ring formed as each of them is linked to an adjacent substituent via alkylene or alkenylene with or without a fused ring may be further substituted by one or more sub- stituent(s) selected from
- L represents anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, (C2-C60) alkenylene or (C2-C60)alkynylene; [28] the anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stil- benylene, alkenylene or alkynylene of L may be independently further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (Cl-C60)alkyl, (C6-C60)ar(Cl-C60)alkyl, halo(Cl-C60)alkyl, mono- or di(C6-C60)arylamino, mono- or di(Cl-C60)alkylarylamino, adamantyl, (C6-C60)aryl and (C3-C60)heteroaryl;
- Ar 1 and Ar 2 independently represent a chemical bond, phenylene, fluorenylene,
- R 41 through R 44 independently represent hydrogen, halogen, deuterium,
- the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl, heterocycloalkyl, adamantyl, cycloalkyl, alkenyl, alkynyl or fused ring of R 41 through R 44 may be further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (Cl-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C 1 -C60)alkylsilyl, di(C 1 -C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl
- the organic electroluminescent device according to the present invention shows an efficient host-dopant energy transfer mechanism, it may exhibit highly efficient electroluminescence performance through improved electron density distribution. Further, it may overcome the problems of existing materials, i.e. low initial efficiency, short operation life, etc., and provide high-performance electroluminescence property with high efficiency and long operation life for each color.
- the compound represented by Chemical Formula 1 that may be included in the organic electroluminescent device of the present invention as a host includes the compounds represented by Chemical Formulas 3 to 9:
- R 1 through R 6 are the same as defined in Chemical Formula 1;
- R 11 through R 35 independently represent hydrogen, deuterium, (Cl-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, cyano, (C3-C60)alkenyl or (C3-C60)alkynyl, or each of them may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring; and
- the alkyl, aryl, heteroaryl, alkenyl or alkynyl of R 11 through R 35 , or the alicyclic ring or the monocyclic or polycyclic aromatic ring that forms a fused ring with an adjacent substituent may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (Cl-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60
- alkyl includes a linear or branched saturated primary hydrocarbon radical consisting only of carbon and hydrogen atoms or a combination thereof
- alkyloxy and alkylthio respectively mean -O-alkyl and -S-alkyl, where the alkyl is the same as defined above.
- aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by chemical bond(s).
- Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
- the naphthyl includes 1 -naphthyl and 2-naphthyl
- the anthryl includes 1 -anthryl, 2-anthryl and 9-anthryl
- the fluorenyl includes 1 -fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- heteroaryl means an aryl group containing 1 to 4 heteroatom(s) selected from nitrogen (N), oxygen (O), sulfur (S), phosphorus (P) and silicon (Si) as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by chemical bond(s).
- the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
- Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as ben- zofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, ben- z
- the substituents including "(Cl-C60)alkyl” may have 1 to 60 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
- the substituents including "(C6-C60)aryl” may have 6 to 60 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
- the substituents including "(C3-C60)heteroaryl” may have 3 to 60 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
- the substituents including "(C3-C60)cycloalkyl” may have 3 to 60 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
- the substituents including "(C2-C60)alkenyl or alkynyl” may have 2 to 60 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
- the host compound represented by Chemical Formula 1 may be exemplified by the following compounds, but are not limited thereto:
- the dopant compound represented by Chemical Formula 2 may be exemplified by the following compounds, but are not limited thereto:
- the electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may comprise two or more layers. In case a combination of a dopant and a host is used in accordance with the present invention, remarkable improvement in luminous efficiency may be attained.
- the organic layer may further contain one or more metal(s) or complex(es) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d- transition elements.
- the organic layer may include an electroluminescent layer and a charge generating layer at the same time.
- the organic layer may include one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, in addition to the organic electroluminescent compounds represented by Chemical Formulas 1 and 2, to provide a white light-emitting organic electroluminescent device.
- the compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
- a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. A driving stability may be attained therefrom.
- the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
- the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes.
- transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion.
- transport of holes from the mixed region to the electroluminescent medium becomes easier, because the hole transport compound is oxidized to a cation.
- Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds.
- Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
- a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
- the organic electroluminescent device according to the present invention exhibits superior luminous efficiency, good color purity and superior operation life. Mode for the Invention
- Organic electroluminescent compounds Compounds 1 to 49, were prepared in the same manner as Preparation Examples 1 to 6. 1 H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
- Example 1 Manufacture of OLED device using the organic electroluminescent compound according to the present invention
- An OLED device was manufactured using the organic electroluminescent compound of the present invention.
- a transparent electrode ITO film (15 ⁇ /D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
- the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
- a vacuum deposition apparatus After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 1O 6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
- NPB ⁇ f, ⁇ bis( ⁇ -naphthyl)-N, ⁇ -diphenyl-4,4'-diamine
- An electroluminescent layer was formed on the hole transport layer as follows.
- Compound 27 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound F was added in another cell as a dopant.
- the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding dinaphthylanthracene (DNA) in another cell of the vacuum deposition apparatus as an electroluminescent host material and adding Compound F in another cell, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- DNA dinaphthylanthracene
- Compound F Compound F
- Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 5,000 cd/m 2 . The result is given in Table 2.
- the organic electroluminescent compounds according to the present invention exhibit lower driving voltage and improved luminous efficiency, as compared to Comparative Example 1, while maintaining comparable or better color purity.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1, and then an electroluminescent layer was formed thereon as follow.
- Compound 8 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound A was added in another cell as a dopant. The two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- an electron transport layer and an electron injection layer were formed in the same manner as Example 1, and an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
- Electroluminescent property of OLED device using existing electroluminescent material [197] A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in another cell of the vacuum deposition apparatus as an electroluminescent host material and adding Compound A, a blue light-emitting electroluminescent material, in another cell, the two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- Luminous efficiency of the OLED devices manufactured in Example 2 and Comparative Example 2 was measured at 1,000 cd/m 2 . The result is given in Table 3.
Abstract
Disclosed is a novel organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) and one or more dopant compound(s). The disclosed organic electroluminescent device exhibits superior luminous efficiency, good color purity and excellent operation life.
Description
The present invention relates to an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) represented by Chemical Formula 1 and one or more dopant compound(s) represented by Chemical Formula 2:
[Chemical Formula 1]
wherein
ring A represents a fused aromatic ring formed as two or more rings are fused, excluding the case where the ring A is benzanthracene or tetracene;
[Chemical Formula 2]
wherein
L represents anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, (C2-C60)alkenylene or (C2-C60)alkynylene.
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and emit light as the electron-hole pair is extinguished. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since the organic EL device may exhibit green, blue and red colors, it is drawing a lot of attentions as a full-color display device of the next generation.
In an organic EL device, the most important factor that determines its performance including luminous efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
In general, the organic EL device commonly has a configuration of anode/HIL/HTL/EML/ETL/EIL/cathode. Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the electroluminescent layer (EML).
Existing electroluminescent materials used to prepare green- or blue-emitting organic electroluminescent devices are problematic in terms of operation life and luminous efficiency.
The inventors of the present invention have made efforts to solve the aforesaid problem. As a result, they have invented an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, the organic layer including an electroluminescent layer containing a combination of specific compounds, in order to provide an organic electroluminescent device exhibiting high color purity, high brightness and long operation life.
Accordingly, an object of the present invention is to provide an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) and one or more dopant compound(s), the organic electroluminescent device having excellent luminous efficiency, superior color purity, low driving voltage and good operation life.
The present invention provides an organic electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more host compound(s) represented by Chemical Formula 1 and one or more dopant compound(s) represented by Chemical Formula 2:
[Chemical Formula 1]
wherein
ring A represents a fused aromatic ring formed as two or more rings are fused, except for the case where the ring A is benzanthracene or tetracene;
R1 through R6 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C1-C60)alkoxy, (C6-C60)aryl, (C3-C60)heteroaryl, halogen, cyano, (C2-C60)alkenyl or (C2-C60)alkynyl, or each of R1 through R6 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring;
the fused aromatic ring of the ring A, and the alkyl, alkoxy, aryl, heteroaryl, alkenyl or alkynyl of R1 through R6, or the fused ring formed as each of them is linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring may be further substituted by hydrogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, (C3-C60)alkenyl, (C3-C60)alkynyl or cyano, wherein the substituent further substituted at the ring A, R1 through R6 or the fused ring formed as each of them is linked to an adjacent substituent via alkylene or alkenylene with or without a fused ring may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl; and
[Chemical Formula 2]
wherein
L represents anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, (C2-C60)alkenylene or (C2-C60)alkynylene;
the anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, alkenylene or alkynylene of L may be independently further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)ar(C1-C60)alkyl, halo(C1-C60)alkyl, mono- or di(C6-C60)arylamino, mono- or di(C1-C60)alkylarylamino, adamantyl, (C6-C60)aryl and (C3-C60)heteroaryl;
Ar1 and Ar2 independently represent a chemical bond, phenylene, fluorenylene, 
or 
;
R41 through R44 independently represent hydrogen, halogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, mono- or di(C6-C60)arylamino, mono- or di(C1-C60)alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, adamantyl, (C3-C60)cycloalkyl, (C2-C60)alkenyl or (C2-C60)alkynyl, or each of R41 through R44 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring; and
the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl, heterocycloalkyl, adamantyl, cycloalkyl, alkenyl, alkynyl or fused ring of R41 through R44 may be further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C1-C60)alkoxy, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, carboxyl, nitro and hydroxyl.
Since the organic electroluminescent device according to the present invention shows an efficient host-dopant energy transfer mechanism, it may exhibit highly efficient electroluminescence performance through improved electron density distribution. Further, it may overcome the problems of existing materials, i.e. low initial efficiency, short operation life, etc., and provide high-performance electroluminescence property with high efficiency and long operation life for each color.
The compound represented by Chemical Formula 1 that may be included in the organic electroluminescent device of the present invention as a host includes the compounds represented by Chemical Formulas 3 to 9:
[Chemical Formula 3]
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
[Chemical Formula 7]
[Chemical Formula 8]
[Chemical Formula 9]
wherein
R1 through R6 are the same as defined in Chemical Formula 1;
R11 through R35 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, cyano, (C3-C60)alkenyl or (C3-C60)alkynyl, or each of them may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring; and
the alkyl, aryl, heteroaryl, alkenyl or alkynyl of R11 through R35, or the alicyclic ring or the monocyclic or polycyclic aromatic ring that forms a fused ring with an adjacent substituent may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl.
In the present invention, "alkyl" includes a linear or branched saturated primary hydrocarbon radical consisting only of carbon and hydrogen atoms or a combination thereof, and "alkyloxy" and "alkylthio" respectively mean -O-alkyl and -S-alkyl, where the alkyl is the same as defined above.
In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by chemical bond(s). Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
In the present invention, "heteroaryl" means an aryl group containing 1 to 4 heteroatom(s) selected from nitrogen (N), oxygen (O), sulfur (S), phosphorus (P) and silicon (Si) as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by chemical bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but are not limited thereto.
In the present invention, the substituents including "(C1-C60)alkyl" may have 1 to 60 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The substituents including "(C6-C60)aryl" may have 6 to 60 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The substituents including "(C3-C60)heteroaryl" may have 3 to 60 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The substituents including "(C3-C60)cycloalkyl" may have 3 to 60 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The substituents including "(C2-C60)alkenyl or alkynyl" may have 2 to 60 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
The host compound represented by Chemical Formula 1 may be exemplified by the following compounds, but are not limited thereto:
The dopant compound represented by Chemical Formula 2 may be exemplified by the following compounds, but are not limited thereto:
The electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may comprise two or more layers. In case a combination of a dopant and a host is used in accordance with the present invention, remarkable improvement in luminous efficiency may be attained.
In the organic electroluminescent device of the present invention, the organic layer may further contain one or more metal(s) or complex(es) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. The organic layer may include an electroluminescent layer and a charge generating layer at the same time.
Also, the organic layer may include one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, in addition to the organic electroluminescent compounds represented by Chemical Formulas 1 and 2, to provide a white light-emitting organic electroluminescent device. The compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. A driving stability may be attained therefrom.
The chalcogenide may be, for example, SiOx (1 = x = 2), AlOx (1 = x = 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Further, in the electroluminescent device according to the present invention, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. In that case, transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion. Further, transport of holes from the mixed region to the electroluminescent medium becomes easier, because the hole transport compound is oxidized to a cation. Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds. Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
Further, a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
The organic electroluminescent device according to the present invention exhibits superior luminous efficiency, good color purity and superior operation life.
Hereinafter, the organic electroluminescent compound, the preparation method thereof and the electroluminescent property of the device according to the present invention will be described for some compounds. However, the following embodiments are only exemplary and do not limit the scope of the present invention.
[Preparation Examples]
[Preparation Example 1] Preparation of Compound 46
Preparation of Compound
1-1
Dichloromethane (70 mL) and aluminum chloride (15.8 g, 118.8 mmol) were added to a round-bottom flask, and isobenzofuran-1,3-dione (8.0 g, 54.0 mmol) and 1,2,3,4-tetrahydronaphthalene (8.8 mL, 64.8 mol) dissolved in dichloromethane (800 mL) were slowly added thereto. After stirring at 25 ℃ for 24 hours, followed by addition of 35% hydrochloric acid (30 mL) and ice water (150 mL), the reaction mixture was further stirred for 20 minutes. Extraction of the reaction mixture with ethyl acetate (200 mL) followed by recrystallization and drying yielded Compound 1-1 (10.6 g, 37.8 mmol).
Preparation of Compound
1-2
Compound 1-1 (10.6 g, 37.8 mmol), aluminum chloride (50.4 g, 378.1 mmol) and sodium chloride (11.1 g, 189.0 mmol) were stirred at 130 ℃ for 4 hours under reflux. After cooling to 25 ℃, the reaction product was dissolved by adding tetrahydrofuran (60 mL), and the reaction was terminated by adding water (30 mL). Upon completion of the reaction, extraction with dichloromethane (100 mL) followed by drying under reduced pressure yielded Compound 1-2 (3 g, 11.4 mmol).
Preparation of Compound
1-3
2-Bromonaphthalene (8.5 g, 40.9 mmol) was dissolved in tetrahydrofuran (50 mL) and n-butyllithium (2.5 M solution in n-hexane, 4.3 mL, 45.7 mmol) was slowly added thereto at -72 ℃. After stirring for 2 hours, followed by addition of Compound 1-2 (3.0 g, 11.4 mmol), the mixture was stirred at room temperature for 24 hours. Upon termination the reaction by slowly adding distilled water (50 mL), extraction of the reaction mixture with tetrahydrofuran (250 mL) followed by drying under reduced pressure yielded Compound 1-3 (3.5 g, 6.8 mmol).
Preparation of Compound
46
Compound 1-3 (3.6 g, 6.8 mmol), potassium iodide (4.5 g, 27.1 mmol) and sodium hydrophosphinate (5.8 g, 54.6 mmol) were dissolved in a mixture solution of acetic acid (30 mL) and dichloromethane (10 mL) and stirred for 24 hours under reflux. After cooling to 25 ℃, water (20 mL) was slowly added to terminate the reaction. Extraction with dichloromethane (200 mL) followed by recrystallization and drying yielded Compound 46 (2.8 g, 5.8 mmol, overall yield = 11%).
[Preparation Example 2] Preparation of Compound 12
Preparation of Compound
2-1
9,9-Dimethylfluorene (20.0 g, 102.9 mmol) and AlCl3 (27.5 g, 205.9 mmol) were dissolved in dichloromethane (500 mL) and isobenzofuran-1,3-dione (22.9 g, 154.4 mmol) was added thereto. After stirring for 12 hours while heating at 40 ℃, distilled water was added to terminate the reaction. After addition of aqueous 1 M HCl solution, followed by extraction with MC and distillation under reduced pressure, column separation yielded Compound 2-1 (33.0 g, 96.4 mmol).
Preparation of Compound
2-2
Compound 2-1 (33.0 g, 96.4 mmol) was added to a mixture of sulfuric acid (100 mL) and acetic acid (100 mL) and stirred at 120 ℃. 10 hours later, cooling to room temperature followed by addition of distilled water yielded a solid. Filtration of thus produced solid under reduced pressure followed by recrystallization with methanol and ethyl acetate yielded Compound 2-2 (9.4 g, 29.0 mmol).
Preparation of Compound
2-3
2-Bromonaphthalene (15.0 g, 72.5 mmol) was dissolved in THF (100 mL) and n-BuLi (35 mL, 87.0 mmol, 2.5 M in hexane) was slowly added dropwise at -78 ℃. One hour later, after adding Compound 2-2 (9.4 g, 29.0 mmol), the mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, extraction with ethyl acetate followed by drying with magnesium sulfate and filtration under reduced pressure yielded Compound 2-3, which was used in the following process without purification.
Preparation of Compound
12
Unpurified Compound 2-3, KI (19.5 g, 117.6 mmol) and NaH2PO3·H2O (23.8 g, 174.0 mmol) were dissolved in acetic acid (100 mL) and stirred at 120 ℃ under reflux. 6 hours later, after cooling to room temperature, distilled water was added. The resulting solid was filtered under reduced pressure. Recrystallization of the solid with methanol, ethyl acetate and chloroform yielded Compound 12 (6.6 g, 12.1 mmol, 42 %).
[Preparation Example 3] Preparation of Compound 23
Preparation of Compound
3-1
9,9-Dimethylfluorene (20.0 g, 102.9 mmol) and AlCl3 (27.5 g, 205.9 mmol) were dissolved in dichloromethane (500 mL) and, after adding 5-bromoisobenzofuran-1,3-dione (35.0 g, 154.4 mmol), stirred while heating at 40 ℃. 12 hours later, after terminating the reaction by adding distilled water, aqueous 1 M HCl solution was added and extraction was carried out using MC. Distillation under reduced pressure followed by column separation yielded Compound 3-1 (40.6 g, 96.4 mmol).
Preparation of Compound
3-2
Compound 3-1 (40.6 g, 96.4 mmol) was added to a mixture of sulfuric acid (300 mL) and acetic acid (300 mL) and stirred at 120 ℃. 10 hours later, cooling to room temperature followed by addition of distilled water yielded a solid. Filtration of thus produced solid under reduced pressure followed by recrystallization with methanol and ethyl acetate yielded Compound 3-2 (11.6 g, 29.0 mmol).
Preparation of Compound
3-3
Compound 3-2 (11.6 g, 29.0 mmol), phenylboronic acid (4.6 g, 37.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 1.7 g, 1.6 mmol) were dissolved in a mixture of toluene (250 mL) and ethanol (80 m) and, after adding aqueous 2 M sodium carbonate solution (100 mL), stirred at 120 ℃ for 4 hours under reflux. Then, after cooling to 25 ℃, distilled water was added to terminate the reaction. Extraction with ethyl acetate followed by drying under reduced pressure and column chromatography yielded Compound 3-3 (10.6 g, 26.5 mmol).
Preparation of Compound
3-4
2-Bromonaphthalene (15.0 g, 72.5 mmol) was dissolved in THF (100 mL) and n-BuLi (35 mL, 87.0 mmol, 2.5 M in hexane) was slowly added dropwise thereto at -78 ℃. One hour later, Compound 3-3 (10.6 g, 26.5 mmol) was added and stirred at room temperature for 12 hours. Upon completion of the reaction, extraction with ethyl acetate followed by drying with magnesium sulfate and filtration under reduced pressure yielded Compound 3-4, which was used in the following process without purification.
Preparation of Compound
23
Unpurified Compound 3-4, KI (19.5 g, 117.6 mmol) and NaH2PO3·H2O (23.8 g, 174.0 mmol) were dissolved in acetic acid (100 mL) and stirred at 120 ℃ under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the resulting solid was filtered under reduced pressure. Column separation of the solid yielded Compound 23 (4.2 g, 6.1 mmol, 45 %).
[Preparation Example 4] Preparation of Compound 27
Preparation of Compound
4-1
2-Bromo-9,9-dimethylfluorene (20.0 g, 73.2 mmol) and AlCl3 (19.5 g, 146.4 mmol) were dissolved in dichloromethane (500 mL) and, after adding isobenzofuran-1,3-dione (22.9 g, 154.4 mmol), stirred while heating at 40 ℃. 12 hours later, the reaction was terminated by adding distilled water, and the product was extracted with MC after adding aqueous 1 M HCl solution. Distillation under reduced pressure followed by column separation yielded Compound 4-1 (30.0 g, 71.2 mmol).
Preparation of Compound
4-2
Compound 4-1 (30.0 g, 71.2 mmol) was added to a mixture of sulfuric acid (100 mL) and acetic acid (100 mL) and stirred at 120 ℃. 10 hours later, cooling to room temperature followed by addition of distilled water yielded a solid. Extraction of thus produced solid under reduced pressure followed by recrystallization with methanol and ethyl acetate yielded Compound 4-2 (4.0 g, 9.9 mmol).
Preparation of Compound
4-3
Compound 4-2 (4.0 g, 9.9 mmol), phenylboronic acid (2.6 g, 14.8 mmol) and 3 M K2CO3 (10 mL) were added to a mixture of toluene (70 mL) and ethanol (30 mL) and stirred under reflux. 12 hours later, after cooling to room temperature, distilled water was added and the product was extracted with dichloromethane. Drying with magnesium sulfate followed by filtration under reduced pressure and column separation yielded Compound 4-3 (3.5 g, 8.7 mmol).
Preparation of Compound
4-4
4-Bromobenzene (3.4 g, 21.8 mmol) was dissolved in THF (100 mL) and n-BuLi (10.4 mL, 26.1 mmol, 2.5 M in hexane) was slowly added dropwise thereto at -78 ℃. One hour later, after adding Compound 4-3 (3.5 g, 8.7 mmol), the mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, extraction with ethyl acetate followed by drying with magnesium sulfate and filtration under reduced pressure yielded Compound 4-4, which was used in the following process without purification.
Preparation of Compound
27
Unpurified compound 4-4, KI (28.9 g, 174.0 mmol) and NaH2PO3·H2O (30.2 g, 148.0 mmol) were dissolved in acetic acid (100 mL) and stirred at 120 ℃ under reflux. 6 hours later, after cooling to room temperature and adding distilled water, the resulting solid was filtered under reduced pressure. Recrystallization of the solid with methanol, ethyl acetate and chloroform yielded Compound 27 (3.5 g, 6.7 mmol, 66 %).
[Preparation Example 5] Preparation of Compound 28
Preparation of Compound
5-1
1-Bromo-2-methylnaphthalene (14.1 mL, 81.4 mmol) was mixed with pyridine (200 mL) and KMnO4 (31.1 g) and distilled water (25 mL) were added thereto simultaneously. While stirring under reflux, KMnO4 (10.0 g) and distilled water (30 mL) were added 4 times with 30 minute intervals. After adding distilled water (200 mL), the mixture was stirred for 12 hours under reflux. After hot filtration, the mixture was washed with boiling distilled water. The filtrate was concentrated by distillation under reduced pressure. After adding hydrochloric acid, the resulting solid was filtered under reduced pressure. Drying under reduced pressure yielded Compound 5-1 (8.3 g, 33.1 mmol).
Preparation of Compound
5-2
Compound 5-1 (8.3 g, 33.1 mmol) was dissolved in methanol (100 mL) and stirred after adding sulfuric acid (2 mL) thereto. 2 hours later, distilled water was added and the product was extracted with dichloromethane. Drying with magnesium sulfate followed by distillation under reduced pressure and column separation yielded Compound 5-2 (6.8 g, 25.7 mmol).
Preparation of Compound
5-3
1-Bromoanthracene-9,10-dione (20.0 g, 69.7 mmol) was dissolved in acetic acid (200 mL) and HI (109.8 mL, 819.7 mmol, 57%) and H3PO2 (67.9 mL, 655.7 mmol, 50%) were added thereto. The mixture was stirred for two days under reflux. After cooling to room temperature, distilled water was added and the resulting solid was filtered under reduced pressure. After washing with aqueous KOH solution, the solid was dissolved in chloroform and filtered with silica gel. Recrystallization with ethyl acetate and methanol yielded Compound 5-3 (14.0 g, 54.8 mmol).
Preparation of Compound
5-4
Compound 5-3 (14.0 g, 54.8 mmol) was dissolved in THF (500 mL) and n-BuLi (26 mL, 65.4 mmol, 2.5 M in hexane) was slowly added thereto at -78 ℃. One hour later, trimethyl borate (12.5 mL, 112.0 mmol) was added. After slowly heating to room temperature, the mixture was stirred at room temperature for 12 hours. After adding distilled water, the product was extracted with ethyl acetate. Drying with magnesium sulfate followed by filtration under reduced pressure, distillation under reduced pressure and column separation yielded Compound 5-4 (8.0 g, 36.0 mmol).
Preparation of Compound
5-5
Compound 5-2 (7.0 g, 26.4 mmol), Compound 5-4 (6.4 g, 29.0 mmol), Pd(PPh3)4 (1.2 g, 1.1 mmol) and Na2CO3 (8.3 g, 79.2 mmol) were added to a mixture of distilled water (40 mL), toluene (100 mL) and ethanol (50 mL) and stirred for 5 hours under reflux. After cooling to room temperature followed by addition of distilled water, the product was extracted with ethyl acetate. Drying with magnesium sulfate followed by distillation under reduced pressure and column separation yielded Compound 5-5 (8.2 g, 22.6 mmol).
Preparation of Compound
5-6
Compound 5-5 (8.0 g, 22.1 mmol) was dissolved in THF and methylmagnesium bromide (25.7 mL, 77.3 mmol, 3.0 M in diethyl ether) was added thereto. The mixture was stirred while heating at 60 ℃. 12 hours later, after cooling to room temperature, distilled water was added. Extraction with MC followed by drying with magnesium sulfate, distillation under reduced pressure and column separation yielded Compound 5-6 (7.0 g, 19.3 mmol).
Preparation of Compound
5-7
Compound 5-6 (7.0 g, 19.3 mmol) was added to acetic acid (100 mL) and H3PO4 (100 mL) was added thereto. After heating at 100 ℃ for 1 hour, the mixture was cooled to room temperature. After adding distilled water, aqueous NaOH solution was added to neutralize the mixture solution. Extraction with MC followed by column separation yielded Compound 5-7 (4.0 g, 11.6 mmol).
Preparation of Compound
5-8
Compound 5-7 (4.0 g, 11.6 mmol) was dissolved in dichloromethane (100 mL) and NBS (5.2 g, 29.0 mmol) was added thereto. The mixture was stirred at room temperature for 12 hours. After distillation under reduced pressure, the resulting solid was washed with methanol, distilled water and hexane. Compound 5-8 (5.5 g, 11.0 mmol) was obtained.
Preparation of Compound
28
Compound 5-8 (5.5 g, 11.0 mmol), phenylboronic acid (5.6 g, 32.9 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol) and K2CO3 (4.5 g, 32.9 mmol) were added to a mixture of distilled water (10 mL), toluene (50 mL) and ethanol (25 mL) and stirred for 5 hours under reflux. After cooling to room temperature, methanol was added. The resulting solid was filtered under reduced pressure and washed sequentially with distilled water, methanol and hexane. Recrystallization sequentially with EA, DMF/EA and THF/EA yielded Compound 28 (5.2 g, 8.7 mmol, 87%).
[Preparation Example 6] Preparation of Compound 36
Preparation of Compound
6-1
After adding magnesium (Mg) turning (1.7 g, 70.1 mmol) in a 100 mL round-bottom flask, a small quantity of I2 and tetrahydrofuran (10 mL) were added thereto. 9-Bromophenanthrene (11 g, 42.5 mmol) dissolved in tetrahydrofuran (10 mL) was slowly added to the flask at 0 ℃ and stirred at 25 ℃ for 30 minutes. Then, after adding 5-bromoisobenzofuran-1,3-dione (9.9 g, 43.4 mmol) and aluminum chloride (12.7 g, 95.6 mmol) thereto, the mixture was stirred for 24 hours. The reaction solution was slowly added to aqueous 1 N HCl solution (150 mL) and stirred for 30 minutes. Extraction with dichloromethane (200 mL) followed by drying under reduced pressure yielded Compound 6-1 (11.4 g, 28.2 mmol).
Preparation of Compound
6-2
Compound 6-2 (2.6 g, 6.8 mmol) was yielded in the same manner as Preparation Example 2, using Compound 6-1 (11.4 g, 28.2 mmol), aluminum chloride (37.9 g, 284.4 mmol) and sodium chloride (8.3 g, 142.2 mmol).
Preparation of Compound
6-3
2-Bromonaphthalene (5.1 g, 24.6 mmol) was dissolved in THF (100 mL) and n-butyllithium (2.5 M in n-Hexane, 2.5 mL, 27.3 mmol) was slowly added thereto at -78 ℃. One hour later, after adding Compound 6-2 (2.6 g, 6.8 mmol), the mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, extraction with ethyl acetate followed by drying with magnesium sulfate and filtration under reduced pressure yielded Compound 6-3, which was used in the following process without purification.
Preparation of Compound
6-4
Unpurified compound 6-3, KI (2.5g, 14.8 mmol) and NaH2PO3·H2O (3.1 g, 29.6 mmol) were dissolved in acetic acid (100 mL) and stirred at 120 ℃ under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the resulting solid was filtered under reduced pressure. Column separation of the solid yielded Compound 6-4 (1.95 g, 3.2 mmol).
Preparation of Compound
36
Compound 6-4 (1.95 g, 3.2 mmol), naphthaleneboronic acid (664.0 mg, 3.9 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(Ph3)4, 0.2 g, 1.7 mmol) and aqueous 2 M sodium carbonate solution (2.3 mL) were added to a mixture solution of toluene (30 mL) and ethanol (15 mL) and stirred for 5 hours under reflux. Upon completion of the reaction, after cooling to room temperature, methanol was added to produce a solid. Thus produced solid was filtered under reduced pressure and washed sequentially with distilled water, methanol and hexane. Recrystallization sequentially with EA, DMF/EA and THF/EA yielded Compound 36 (1.2 g, 2.2 mmol).
Organic electroluminescent compounds, Compounds 1 to 49, were prepared in the same manner as Preparation Examples 1 to 6. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
[Table 1]
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the organic electroluminescent compound of the present invention.
First, a transparent electrode ITO film (15 Ω/□) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
Then, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10-6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
Subsequently, after adding N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current to the cell to form a hole transport layer having a thickness of 20 nm on the hole injection layer.
An electroluminescent layer was formed on the hole transport layer as follows. Compound 27 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound F was added in another cell as a dopant. The two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Thereafter, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was deposited with a thickness of 20 nm on the electroluminescent layer as an electron transport layer, and lithium quinolate (Liq) was deposited with a thickness of 1 to 2 nm as an electron injection layer. Then, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Each OLED electroluminescent used in the OLED device had been purified by vacuum sublimation at 10-6 torr.
[Comparative Example 1] Electroluminescent property of OLED device using existing electroluminescent material
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding dinaphthylanthracene (DNA) in another cell of the vacuum deposition apparatus as an electroluminescent host material and adding Compound F in another cell, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, after forming an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 5,000 cd/m2. The result is given in Table 2.
[Table 2]
As seen from Table 2, when applied to a green light-emitting electroluminescent device, the organic electroluminescent compounds according to the present invention exhibit lower driving voltage and improved luminous efficiency, as compared to Comparative Example 1, while maintaining comparable or better color purity.
[Example 2] Preparation of OLED device using the organic electroluminescent compound according to the present invention
A hole injection layer and a hole transport layer were formed in the same manner as Example 1, and then an electroluminescent layer was formed thereon as follow. Compound 8 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound A was added in another cell as a dopant. The two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, an electron transport layer and an electron injection layer were formed in the same manner as Example 1, and an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
[Comparative Example 2] Electroluminescent property of OLED device using existing electroluminescent material
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in another cell of the vacuum deposition apparatus as an electroluminescent host material and adding Compound A, a blue light-emitting electroluminescent material, in another cell, the two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, after forming an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Luminous efficiency of the OLED devices manufactured in Example 2 and Comparative Example 2 was measured at 1,000 cd/m2. The result is given in Table 3.
[Table 3]
As seen from Table 3, when applied to a blue light-emitting electroluminescent device, the organic electroluminescent compounds according to the present invention exhibit comparable or better luminous efficiency as compared to Comparative Example 2.
Claims (5)
- An organic electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more host compound(s) represented by Chemical Formula 1 and one or more dopant compound(s) represented by Chemical Formula 2:[Chemical Formula 1]
whereinring A represents a fused aromatic ring formed as two or more rings are fused, except for the case where the ring A is benzanthracene or tetracene;R1 through R6 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C1-C60)alkoxy, (C6-C60)aryl, (C3-C60)heteroaryl, halogen, cyano, (C2-C60)alkenyl or (C2-C60)alkynyl, or each of R1 through R6 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring;the fused aromatic ring of the ring A, and the alkyl, alkoxy, aryl, heteroaryl, alkenyl or alkynyl of R1 through R6, or the fused ring formed as each of them is linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring may be further substituted by hydrogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, (C3-C60)alkenyl, (C3-C60)alkynyl or cyano, wherein the substituent further substituted at the ring A, R1 through R6 or the fused ring formed as each of them is linked to an adjacent substituent via alkylene or alkenylene with or without a fused ring may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl; and[Chemical Formula 2]
whereinL represents anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, (C2-C60)alkenylene or (C2-C60)alkynylene;the anthracenylene with or without substituent(s), pyrenylene, chrysenylene, stilbenylene, alkenylene or alkynylene of L may be independently further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)ar(C1-C60)alkyl, halo(C1-C60)alkyl, mono- or di(C6-C60)arylamino, mono- or di(C1-C60)alkylarylamino, adamantyl, (C6-C60)aryl and (C3-C60)heteroaryl;Ar1 and Ar2 independently represent a chemical bond, phenylene, fluorenylene,or
;
R41 through R44 independently represent hydrogen, halogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, mono- or di(C6-C60)arylamino, mono- or di(C1-C60)alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, adamantyl, (C3-C60)cycloalkyl, (C2-C60)alkenyl or (C2-C60)alkynyl, or each of R41 through R44 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring; andthe alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl, heterocycloalkyl, adamantyl, cycloalkyl, alkenyl, alkynyl or fused ring of R41 through R44 may be further substituted by one or more substituent(s) selected from hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C1-C60)alkoxy, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, carboxyl, nitro and hydroxyl. - The organic electroluminescent device according to claim 1, wherein the host compound represented by Chemical Formula 1 is a compound represented by one of Chemical Formulas 3 to 9:[Chemical Formula 3]
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
[Chemical Formula 7]
[Chemical Formula 8]
[Chemical Formula 9]
whereinR1 through R6 are the same as defined in claim 1;R11 through R35 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl, halogen, cyano, (C3-C60)alkenyl or (C3-C60)alkynyl, or each of them may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring; andthe alkyl, aryl, heteroaryl, alkenyl or alkynyl of R11 through R35, or the alicyclic ring or the monocyclic or polycyclic aromatic ring that forms a fused ring with an adjacent substituent may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, (C6-C60)aryloxycarbonyl, (C1-C60)alkoxycarbonyloxy, (C1-C60)alkylcarbonyloxy, (C6-C60)arylcarbonyloxy, (C6-C60)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl. - The organic electroluminescent device according to claim 1, wherein the organic layer further comprises one or more metal(s) or complex(es) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
- The organic electroluminescent device according to claim 1, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 1, which is a white light-emitting organic electroluminescent device wherein the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2009-0024445 | 2009-03-23 | ||
| KR1020090024445A KR101645949B1 (en) | 2009-03-23 | 2009-03-23 | Electroluminescent device using the electroluminescent compounds |
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| Publication Number | Publication Date |
|---|---|
| WO2010110554A2 true WO2010110554A2 (en) | 2010-09-30 |
| WO2010110554A3 WO2010110554A3 (en) | 2010-11-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2010/001692 WO2010110554A2 (en) | 2009-03-23 | 2010-03-18 | Organic electroluminescent device using organic electroluminescent compounds |
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| Country | Link |
|---|---|
| KR (1) | KR101645949B1 (en) |
| TW (1) | TW201105609A (en) |
| WO (1) | WO2010110554A2 (en) |
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| CN103187538A (en) * | 2011-12-30 | 2013-07-03 | 三星显示有限公司 | Organic light-emitting diode for green color, and flat display device including the same |
| KR101431645B1 (en) | 2012-06-26 | 2014-08-20 | 롬엔드하스전자재료코리아유한회사 | Light-Emitting Layer and Organic Electroluminescence Device comprising the same |
| KR101503796B1 (en) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same |
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| CN112279816A (en) * | 2019-07-22 | 2021-01-29 | 南京高光半导体材料有限公司 | Electron transport material and organic electroluminescent device using same |
| US11871661B2 (en) | 2015-12-17 | 2024-01-09 | Samsung Display Co., Ltd. | Organic light-emitting device |
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| CN112279816A (en) * | 2019-07-22 | 2021-01-29 | 南京高光半导体材料有限公司 | Electron transport material and organic electroluminescent device using same |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR101645949B1 (en) | 2016-08-05 |
| KR20100106026A (en) | 2010-10-01 |
| TW201105609A (en) | 2011-02-16 |
| WO2010110554A3 (en) | 2010-11-25 |
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