WO2010114264A2 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- WO2010114264A2 WO2010114264A2 PCT/KR2010/001897 KR2010001897W WO2010114264A2 WO 2010114264 A2 WO2010114264 A2 WO 2010114264A2 KR 2010001897 W KR2010001897 W KR 2010001897W WO 2010114264 A2 WO2010114264 A2 WO 2010114264A2
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- WIPO (PCT)
- Prior art keywords
- substituent
- alkyl
- ring
- aryl
- fused
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 91
- 125000001424 substituent group Chemical group 0.000 claims description 244
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 55
- 239000010410 layer Substances 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000005104 aryl silyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000002950 monocyclic group Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 20
- -1 cyano, carbazolyl Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 16
- 125000003367 polycyclic group Chemical group 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 11
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000003003 spiro 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
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000004020 luminiscence type Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 description 35
- 0 **1c2c(*)c(*)c(*)c(O)c2C2=CC=*C12 Chemical compound **1c2c(*)c(*)c(*)c(O)c2C2=CC=*C12 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000001771 vacuum deposition Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 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
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-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
- 125000000217 alkyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- WWKCGWQJBPFVIG-UHFFFAOYSA-N [O-][N+](c(cccc1)c1-c1cccc2ccccc12)=O Chemical compound [O-][N+](c(cccc1)c1-c1cccc2ccccc12)=O WWKCGWQJBPFVIG-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
- UGFOTZLGPPWNPY-UHFFFAOYSA-N c(cc12)ccc1[nH]c1c2c2ccccc2cc1 Chemical compound c(cc12)ccc1[nH]c1c2c2ccccc2cc1 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- NPLZZSLZTJVZSX-UHFFFAOYSA-L iron(2+);oxalate;dihydrate Chemical compound O.O.[Fe+2].[O-]C(=O)C([O-])=O NPLZZSLZTJVZSX-UHFFFAOYSA-L 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
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 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
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 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
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 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
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-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
- 229910017107 AlOx Inorganic materials 0.000 description 1
- BNZFISIGAJQDOG-UHFFFAOYSA-N Bc1c(cccc2)c2ccc1 Chemical compound Bc1c(cccc2)c2ccc1 BNZFISIGAJQDOG-UHFFFAOYSA-N 0.000 description 1
- LORYLCXFQLBJDH-UHFFFAOYSA-N CC(C1)C=Cc2c1[n](C/N=C(/c1ccccc1)\N=C(\c1ccccc1)/N)c1c2c2ccccc2cc1 Chemical compound CC(C1)C=Cc2c1[n](C/N=C(/c1ccccc1)\N=C(\c1ccccc1)/N)c1c2c2ccccc2cc1 LORYLCXFQLBJDH-UHFFFAOYSA-N 0.000 description 1
- FZDKSHKDQVFUFW-UHFFFAOYSA-N CC[NH+](c1ccccc1Br)[O-] Chemical compound CC[NH+](c1ccccc1Br)[O-] FZDKSHKDQVFUFW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UXECWEJZIMYUJB-UHFFFAOYSA-N ClC1N=C(c2ccccc2)N=C(c2ccccc2)N1 Chemical compound ClC1N=C(c2ccccc2)N=C(c2ccccc2)N1 UXECWEJZIMYUJB-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N Clc1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound Clc1nc(-c2ccccc2)nc(-c2ccccc2)n1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
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- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 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
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ODFBAZOKDBBJEO-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c2c1c(cccc1)c1c(-c1nc(cccc3)c3cc1)c2 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c2c1c(cccc1)c1c(-c1nc(cccc3)c3cc1)c2 ODFBAZOKDBBJEO-UHFFFAOYSA-N 0.000 description 1
- FSZKHDRRSQALJD-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n](c2ccccc22)c3c2c2ccccc2cc3)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-[n](c2ccccc22)c3c2c2ccccc2cc3)nc(-c2ccccc2)n1 FSZKHDRRSQALJD-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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005137 deposition process 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
- 239000012776 electronic material Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 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
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 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
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 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
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 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
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 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
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
Definitions
- the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same.
- the organic electroluminescent compounds according to the present invention are represented by Chemical Formula 1 :
- ring A and ring B independently represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings.
- electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
- 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 to form an exciton. As the exciton is deactivated, light is emitted by phosphorescence or fluorescence.
- An organic EL device emits polarized light with high luminance of about 100-10,000 cd/m 2 at a voltage of about 10 V. It can emit light in the spectrum from blue to red by simply selecting different fluorescent materials.
- 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.
- electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence 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.
- Organic electroluminescent materials may be roughly classified into high- molecular- weight materials and low-molecular- weight materials.
- the low- molecular- weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure.
- Chelate complexes such as tris( 8 -quinolato) aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from blue to red light in the visible region can be obtained using these materials.
- the electroluminescent materials may be divided into host materials and dopant materials.
- an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
- development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
- development of materials which are much superior to existing electroluminescent materials is urgently needed.
- host material is very important. Some requirements of the host material that acts as solid solvent and energy transferor include high purity and adequate molecular weight allowing vacuum deposition. Further, high glass transition temperature and pyrolysis temperature are required for good thermal stability and high electrochemical stability is required for long operation life. In addition, formation of an amorphous thin film should be easy and adhesivity with adjacent layers should be good, but with no interlay er migration.
- CBP 4,4'-N,N'-dicarbazolebiphenyl
- BAIq 4,4'-N,N'-dicarbazolebiphenyl
- an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates.
- Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound as an electroluminescent material.
- the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. Since the organic electroluminescent compound according to the present invention has superior luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very superior operation life.
- ring A and ring B independently represent a monocyclic or poly cyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings; and
- the hydrogen atom of the ring A or the ring B may be further substituted by deuterium.
- alkyl include both linear and branched species.
- 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 single 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.
- 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, isoben- zofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, ben- zoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quino
- the alkyl moiety of " (C 1 -C30)alkyl, tri(C 1 -C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (Cl-C30)alkyloxy, (C 1 -C30)alkylthio, (C 1 -C30)alkyloxycarbonyl, (C 1 -C30)alkylcarbonyl, (Cl-C30)alkyloxycarbonyloxy or (Cl-C30)alkylcarbonyloxy" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
- the aryl alkyl moiety of "(C6-C30)aryl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy" may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
- the "(C3-C30)heteroaryl” may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
- the "(C3-C30)cycloalkyl” may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
- the "(C2-C30)alkenyl or alkynyl” may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
- the phrase "with or without substituent(s)” means that the substituents of R 1 through R 3 and R 11 through R 18 may be independently substituted with one or more substituent(s) selected from a group consisting of deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)aryl
- the organic electroluminescent compound according to the present invention which is represented by Chemical Formula 1, includes the organic electroluminescent compounds represented by Chemical Formulas 2 to 6:
- B 1 through B 6 independently represent CR 3 or N;
- each R 3 may be linked via
- the organic electroluminescent compound according to the present invention may be selected from the following compounds, but is not limited thereto: [47]
- R 1 is the same as defined in Chemical Formula 1; [61] R 41 through R 44 are the same as defined in Chemical Formulas 2 to 6; and [62] R 45 through R 66 independently represent hydrogen, deuterium, halogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without sub- stituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered hete- rocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without sub- stituent(s),(
- organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
- organic electroluminescent compound according to the present invention may be prepared by Schemes 1 to 3:
- the present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode.
- the organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
- the organic layer may include an electroluminescent layer which further includes one or more dopant(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
- the dopant used in the organic electronic device of the present invention is not particularly limited.
- the dopant used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formula 7:
- M 1 is selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals;
- the ligands L 101 , L 102 and L 103 are independently selected from the following structures:
- R2 0 1 through R2 0 3 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s), or halogen;
- R 204 through R 219 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (Cl-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(Cl-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF 5 , tri(Cl-C30)alkylsilyl with or without substituent(s), di(Cl-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
- R 220 through R 223 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), or (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s;
- R 224 and R 225 independently represent hydrogen, (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s), or halogen, or R 224 and R 225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or poly cyclic aromatic ring;
- R 226 represents (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;
- R 227 through R 229 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
- R 231 through R 242 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (Cl-C30)alkoxy, halogen, (C6-C30)aryl with or without sub- stituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring or linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- the dopant compound represented by Chemical Formula 7 may be exemplified by the following compounds, but is not limited thereto:
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, 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.
- the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, 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.
- injection and transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion.
- injection and 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.
- reductive dopant examples 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 compound according to the present invention exhibits good luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very good operation life.
- 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,./V-bis( ⁇ -naphthyl)-/V,./V '- diphenyl-4,4'-diamine
- An electroluminescent layer was formed on the hole transport layer as follows. Compound 13 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and (piq) 2 Ir(acac) 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 4 to 10 wt% based on (piq) 2 Ir(acac).
- Each electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10 6 torr.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding CBP as an electroluminescent host material in another cell of the vacuum deposition apparatus, and adding (piq) 2 Ir(acac) 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 4 to 10 wt% based on (piq)2 Ir(acac).
- BAIq was deposited with a thickness of 5 nm on the electroluminescent layer as a hole blocking layer, and AIq was deposited with a thickness of 20 nm as an electron transport layer. Then, after depositing Liq with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
- the organic electroluminescent compounds according to the present invention exhibit superior electroluminescence properties as compared to the existing material. Further, the devices wherein the organic electroluminescent compounds according to the present invention are used as host material exhibit decreased driving voltage and power efficiency increased by 1.7-3.2 ImAV. Therefore, power consumption can be reduced.
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Abstract
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. Since the organic electroluminescent compounds according to the present invention exhibit high luminescence efficiency and excellent color purity and life property, they may be used to manufacture OLEDs with very good operation life.
Description
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same. Specifically, the organic electroluminescent compounds according to the present invention are represented by Chemical Formula 1:
[Chemical Formula 1]
wherein ring A and ring B independently represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings.
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 to form an exciton. As the exciton is deactivated, light is emitted by phosphorescence or fluorescence. An organic EL device emits polarized light with high luminance of about 100-10,000 cd/m2 at a voltage of about 10 V. It can emit light in the spectrum from blue to red by simply selecting different fluorescent materials. 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.
In an organic EL device, the most important factor that determines its performance including luminescence 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.
Organic electroluminescent materials may be roughly classified into high-molecular-weight materials and low-molecular-weight materials. The low-molecular-weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure. Chelate complexes such as tris(8-quinolato)aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from blue to red light in the visible region can be obtained using these materials.
In order to realize a full-color OLED display, three electroluminescent materials of red, green and blue (RGB) are employed. Thus, development of RGB electroluminescent materials having high efficiency and long operation life is important in enhancing the properties of an organic EL device. In functional aspect, the electroluminescent materials may be divided into host materials and dopant materials. In general, an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task. Especially, considering the level of EL performance required for medium-to-large sized OLED panels, development of materials which are much superior to existing electroluminescent materials is urgently needed. In this regard, development of host material is very important. Some requirements of the host material that acts as solid solvent and energy transferor include high purity and adequate molecular weight allowing vacuum deposition. Further, high glass transition temperature and pyrolysis temperature are required for good thermal stability and high electrochemical stability is required for long operation life. In addition, formation of an amorphous thin film should be easy and adhesivity with adjacent layers should be good, but with no interlayer migration.
When manufacturing an organic EL device using a doping technique, there is a problem in that efficiency of energy transfer from a host molecule to a dopant in the excited state is not 100% and that, not only the dopant, the host material also emits light. Especially, in case of a red-emitting EL device, the host material emits light at a more visible wavelength region than the dopant, which degrades color purity of the emitted light. In addition, for practical application, lifetime and consistency of electroluminescence need to be improved.
Up to the present, 4,4'-N,N'-dicarbazolebiphenyl (CBP) is the best known host material of a phosphorescent light-emitting material, and OLEDs with high efficiency including a hole blocking layer of BCP or BAlq are known. Also, high-performance OLEDs using BAlq derivatives as the host have been developed by Pioneer (Japan) or the like.
Although these materials are advantageous in view of light-emitting properties, their properties may be modified during high-temperature deposition process in vacuum because of low glass transition temperature and very poor thermal stability. The power efficiency of an OLED is determined by "power efficiency = (π / voltage) × current efficiency". That is, the power efficiency is inversely proportional to the voltage, and the power efficiency should be improved to reduce power consumption of the OLED. In practice, an OLED employing a phosphorescent electroluminescent material exhibits fairly higher current efficiency (cd/A) than one employing a fluorescent electroluminescent material. However, use of BAlq or CBP as host of the phosphorescent electroluminescent material does not provide significant advantage over an OLED employing a fluorescent material in terms of power efficiency (lm/w), because of higher driving voltage. Furthermore, the result is not satisfactory in view of operation life of the OLED device. Accordingly, development of a host material capable of providing better stability and performance is still required.
Accordingly, an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates. Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound as an electroluminescent material.
The present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. Since the organic electroluminescent compound according to the present invention has superior luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very superior operation life.
[Chemical Formula 1]
wherein
ring A and ring B independently represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings; and
R1 though R3 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18[wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring; and
the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P,
the hydrogen atom of the ring A or the ring B may be further substituted by deuterium.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species.
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 single 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 B, N, O, S, P(=O), Si and P 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 single 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 alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C1-C30)alkyloxycarbonyl, (C1-C30)alkylcarbonyl, (C1-C30)alkyloxycarbonyloxy or (C1-C30)alkylcarbonyloxy" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl alkyl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy" may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The "(C3-C30)heteroaryl" may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The "(C3-C30)cycloalkyl" may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The "(C2-C30)alkenyl or alkynyl" may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
And, in the present invention, the phrase "with or without substituent(s)" means that the substituents of R1 through R3 and R11 through R18 may be independently substituted with one or more substituent(s) selected from a group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring.
The organic electroluminescent compound according to the present invention, which is represented by Chemical Formula 1, includes the organic electroluminescent compounds represented by Chemical Formulas 2 to 6:
[Chemical Formula 2]
[Chemical Formula 3]
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
wherein
ring B and R1 and R3 are the same as defined in Chemical Formula 1;
R41 through R44 independently represent independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28[wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
represents 
, 
, 
or 
;
B1 through B6 independently represent CR3 or N; and
if two adjacent entries of B1 through B6 represent CR3, each R3 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.
The organic electroluminescent compound according to the present invention may be selected from the following compounds, but is not limited thereto:
wherein
R1 is the same as defined in Chemical Formula 1;
R41 through R44 are the same as defined in Chemical Formulas 2 to 6; and
R45 through R66 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28[wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring.
More specifically, the organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
The organic electroluminescent compound according to the present invention may be prepared by Schemes 1 to 3:
[Scheme 1]
[Scheme 2]
[Scheme 3]
wherein
ring A, ring B and R1 through R3 are the same as defined in Chemical Formula 1.
The present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode. The organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
Further, the organic layer may include an electroluminescent layer which further includes one or more dopant(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1. The dopant used in the organic electronic device of the present invention is not particularly limited.
Preferably, the dopant used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formula 7:
[Chemical Formula 7]
M1L101L102L103
wherein
M1 is selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals; and
the ligands L101, L102 and L103
are independently selected from the following structures:
wherein
R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s), or halogen;
R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(C1-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s;
R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen, or R224 and R225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;
R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
Q represents 
, 
or 
; and
R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring or linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
The dopant compound represented by Chemical Formula 7 may be exemplified by the following compounds, but is not limited thereto:
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, 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.
Further, the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, 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, injection and transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion. Further, injection and 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.
Since the organic electroluminescent compound according to the present invention exhibits good luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very good operation life.
Hereinafter, the compound for organic electronic material, 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 Example 1] Preparation of Compound 1
Preparation of Compound
1-1
1-Naphthaleneboronic acid (10.2 g, 59.4 mmol), 1-bromo-2-nitrobenzene (10.0 g, 49.5 mmol), Pd(PPh3)4 (1.7 g, 1.4 mmol), 2 M K2CO3 aqueous solution (70 mL), toluene (200 mL) and ethanol (100 mL) were stirred for 12 hours under reflux. After washing with distilled water followed by extraction with EA, drying with anhydrous MgSO4 and distillation under reduced pressure, column separation of the resultant residue yielded Compound 1-1 (9.0 g, 36.1 mmol, 73.7%).
Preparation of Compound
1-2
Compound 1-1 (9.0 g, 36.1 mmol) and N-bromosuccinimide (7.6 g, 43.3 mmol) were dissolved in dichloromethane (300 mL) and stirred for 12 hours at room temperature. After distillation under reduced pressure, washing of thus produced solid sequentially with distilled water, methanol and hexane yielded Compound 1-2 (9.6 g, 29.3 mmol, 81.3%).
Preparation of Compound
1-3
Compound 1-2 (9.6 g, 29.3 mmol) and iron oxalate dihydrate (72.2 g, 175.5 mmol) were mixed and heated at 205 ℃ for 30 minutes. After cooling to room temperature, the product was extracted with EA and washed with distilled water. Recrystallization with toluene yielded Compound 1-3 (5.2 g, 17.6 mmol, 60.5%).
Preparation of Compound
1-4
Compound 1-3 (5.2 g, 17.6 mmol), copper (0.6 g, 8.8 mmol), 18-crown-6 (0.2 g, 0.9 mmol), K2CO3 (4.8 g, 35.1 mmol) and 1,2-dichlorobenzene (100 mL) were mixed and stirred at 180 ℃ for 12 hours under reflux. After cooling to room temperature, the product was distilled under reduced pressure, extracted with MC and washed with distilled water. After drying with anhydrous MgSO4, distillation of the resulting residue under reduced pressure followed by column separation yielded Compound 1-4 (5.0 g, 13.4 mmol, 76.5%).
Preparation of Compound
1
Compound 1-4 (5.0 g, 13.4 mmol), 9-phenyl-anthracene-10-boronic acid (4.8 g, 16.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), 2 M K2CO3 aqueous solution (20 mL), toluene (100 mL) and ethanol (50 mL) were stirred for 12 hours under reflux. After washing with distilled water, extracting with EA and drying with anhydrous MgSO4, distillation of the resultant residue under reduced pressure followed by column separation yielded Compound 1 (4.3 g, 7.9 mmol, 58.8%).
[Preparation Example 2] Preparation of Compound 13
Preparation of Compound
2-1
Cyanuric chloride (10.0 g, 54.22 mmol) was dissolved in THF (35 mL) and cooled to 0 ℃. After slowly adding phenylmagnesium bromide (3.0 M in diethyl ether, 45.1 mL, 135.56 mmol), the mixture was stirred at room temperature for 3 hours. Filtration of thus produced solid under reduced pressure followed by washing with methanol and hexane yielded Compound 2-1 (9 g, 62%).
Preparation of Compound
2-2
1-Naphthaleneboronic acid (10.2 g, 59.4 mmol), 1-bromo-2-nitrobenzene (10.0 g, 49.5 mmol), Pd(PPh3)4 (1.7 g, 1.4 mmol), 2 M K2CO3 aqueous solution (70 mL), toluene (200 mL) and ethanol (100 mL) were stirred for 12 hours under reflux. After washing with distilled water, extracting with EA and drying with anhydrous MgSO4, distillation of the resultant residue under reduced pressure followed by column separation yielded Compound 2-2 (9.0 g, 36.1 mmol, 73.7%).
Preparation of Compound
2-3
Compound 2-2 (9.6 g, 29.3 mmol) and iron oxalate dihydrate (72.2 g, 175.5 mmol) were mixed and heated at 205 ℃ for 30 minutes. After cooling to room temperature, the product was extracted with EA and washed with distilled water. Recrystallization with toluene yielded Compound 2-3 (5.2 g, 17.6 mmol, 60.5%).
Preparation of Compound
13
NaH (60% in mineral oil, 575 mg, 14.38 mmol) was diluted in DMF (30 mL). Then, Compound 2-3 (2.5 g, 11.50 mmol) dissolved in DMF (20 mL) was added. After stirring for an hour at room temperature, Compound 2-1 (3.0 g, 11.50 mmol) dissolved in DMF (20 mL) was added. After stirring at room temperature for 3 hours followed by addition of water (50 mL), thus produced solid was filtered under reduced pressure. Recrystallization of the solid with DMF and EA yielded Compound 13 (2.8 g, 54%).
[Preparation Example 3] Preparation of Compound 33
Preparation of Compound
3-1
4-Fluorophenylhydrazine hydrochloride (10.0 g, 61.5 mmol) was dissolved in a mixture of methanol (143 mL) and water (47 mL) and was stirred for 5 minutes. After adding β-tetralone (8.7 mL, 65.8 mmol), the mixture was stirred vigorously at room temperature for an hour. After extraction of the organic layer with MC, followed by drying with anhydrous MgSO4 and distillation under reduced pressure, column separation yielded Compound 3-1 (9.7 g, 66%).
Preparation of Compound
3-2
Compound 3-1 (9.7 g, 40.53mmol), Pd/C (10%, 11.6 g) and xylene (135 mL) were stirred at 150 ℃ for 12 hours under reflux. After cooling to room temperature, the organic layer was extracted with MC. Drying with anhydrous MgSO4 followed by distillation under reduced pressure and column separation yielded Compound 3-2 (8.3 g, 87%).
Preparation of Compound
33
NaH (60% in mineral oil, 531 mg, 13.28 mmol) was diluted in DMF (20 mL). Then, Compound 3-2 (2.5 g, 10.6 mmol) dissolved in DMF (20 mL) was added. After stirring for an hour at room temperature, Compound 2-1 (2.8 g, 10.6 mmol) dissolved in DMF (30 mL) was added. After stirring at room temperature for 3 hours followed by addition of water (50 mL), thus produced solid was filtered under reduced pressure. Recrystallization of the solid with DMF and EA yielded Compound 33 (2.8 g, 56%).
[Preparation Example 4] Preparation of Compound 124
Preparation of Compound
4-1
2-Chloro-3-nitropyridine (25 g, 157.6 mmol), phenylboronic acid (24.9 g, 204.9 mmol), Pd(PPh3)4 (5.4 g, 4.73 mmol), K2CO3 (54.48 g, 394.2 mmol), distilled water (150 mL), toluene (300 mL) and ethanol (100 mL) were stirred under reflux. 12 hours later, after cooling to room temperature, distilled water was added. After extraction with MC, the product was dried with anhydrous MgSO4. Distillation under reduced pressure followed by column separation yielded Compound 4-1 (30 g, 149.85 mmol, 95.45%).
Preparation of Compound
4-2
Compound 4-1 (30 g, 149.85 mmol) was mixed with triethyl phosphite (150 mL) and stirred at 180 ℃ for 4 hours. After cooling to room temperature, distillation under reduced pressure followed by column separation yielded Compound 4-2 (2.1 g, 12.48 mmol, 8.37%).
Preparation of Compound
124
NaH (0.45 g, 18.72 mmol, 60% in mineral oil) was mixed with DMF (12 mL) and Compound 4-2 (2.1 g, 12.48 mmol) dissolved in DMF (20 mL) was added thereto. After stirring for 30 minutes, Compound 2-1 (3.6 g, 13.73 mmol) dissolved in DMF (25 mL) was added. After stirring for 12 hours, distilled water was added and thus produced solid was filtered under reduced pressure. Recrystallization with EA yielded Compound 124 (2.6 g, 6.50 mmol, 54.24%).
[Preparation Example 5] Preparation of Compound 125
Preparation of Compound
5-1
2-Chloropyridine (10 g, 74.87 mmol), 2-chloroaniline (11.4 g, 89.85 mmol), Pd2(dba)3 (4.0 g, 4.40 mmol), tri-tert-butylphosphine (P(t-Bu)3, 50% in xylene, 11.7 mL, 17.61 mmol), KOt-Bu (69 g, 616.46 mmol) and 1.4-dioxane (50 mL) were heated at 120 ℃ for 20 hours. After extracting the organic layer with MC, drying with anhydrous MgSO4 followed by distillation under reduced pressure and column separation yielded Compound 5-1 (1.3 g, 10%).
Preparation of Compound
125
NaH (60% in mineral oil, 594 mg, 14.86 mmol) was diluted in DMF (20 mL). Then, Compound 5-1 (2.0 g, 11.89 mmol) dissolved in DMF (20 mL) was added. After stirring for an hour at room temperature, Compound 2-1 (3.1 g, 11.89 mmol) dissolved in DMF (30 mL) was added. After stirring at room temperature for 3 hours followed by addition of water (50 mL), thus produced solid was filtered under reduced pressure. Recrystallization of the solid with DMF and EA yielded Compound 125 (3.7 g, 77%).
Organic electroluminescent compounds, Compounds 1 to 128, were prepared in the same manner as Preparation Example 1. 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 13 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and (piq)2Ir(acac) 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 4 to 10 wt% based on (piq)2Ir(acac).
Thereafter, bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III) (BAlq) was deposited with a thickness of 5 nm on the electroluminescent layer as a hole blocking layer, and tris(8-hydroxyquinoline)-aluminum(III) (Alq) was deposited with a thickness of 20 nm as an electron transport layer. Then, after depositing lithium quinolate (Liq) with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Each electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10-6 torr.
[Example 2] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED was manufactured in the same manner as Example 1 except for the hole blocking layer.
[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 CBP as an electroluminescent host material in another cell of the vacuum deposition apparatus, and adding (piq)2Ir(acac) 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 4 to 10 wt% based on (piq)2Ir(acac).
Thereafter, BAlq was deposited with a thickness of 5 nm on the electroluminescent layer as a hole blocking layer, and Alq was deposited with a thickness of 20 nm as an electron transport layer. Then, after depositing Liq with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Luminescence efficiency of the OLED devices manufactured in Examples 1 and 2 and Comparative Example 1 was measured at 1,000 cd/m2. The result is given in Table 2.
[Table 2]
As seen from Table 2, the organic electroluminescent compounds according to the present invention exhibit superior electroluminescence properties as compared to the existing material. Further, the devices wherein the organic electroluminescent compounds according to the present invention are used as host material exhibit decreased driving voltage and power efficiency increased by 1.7-3.2 lm/W. Therefore, power consumption can be reduced.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1:[Chemical Formula 1]
whereinring A and ring B independently represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- or 6-membered heteroaromatic ring fused with an aromatic ring, a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring; excluding the case that both the ring A and the ring B are monocyclic aromatic rings; andR1 though R3 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18[wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring; andthe heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P,the hydrogen atom of the ring A or the ring B may be further substituted by deuterium. - The organic electroluminescent compound according to claim 1, wherein the substituent of R1 through R3 and R11 through R18 is further substituted by one or more substituent(s) selected from a group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring.
- The organic electroluminescent compound according to claim 1, which is represented by one of Chemical Formulas 2 to 6:[Chemical Formula 2]
[Chemical Formula 3]
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
whereinR1 and R3 are defined as in Chemical Formula 1 of claim 1;represents
,
,
or
;
B1 through B6 independently represent CR3 or N;if two adjacent entries of B1 through B6 represent CR3, each R3 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; andR41 through R44 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28[wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring. - The organic electroluminescent compound according to claim 3, which is selected from the following compounds:
whereinR1 is defined as in claim 1; R41 through R44 are defined as in claim 3; andR45 through R66 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28[wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or (C3-C30)heteroaryl with or without substituent(s).], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring. - An organic electroluminescent device comprising an organic electroluminescent compound according to any one of claims 1 to 4.
- The organic electroluminescent device according to claim 5, which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more electroluminescent compound(s) according to any one of claims 1 to 4, and one or more dopant(s) represented by Chemical Formula 7:[Chemical Formula 7]M1L101L102L103whereinM1 is selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals; andthe ligands L101, L102 and L103 are independently selected from the following structures:
whereinR201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s), or halogen;R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(C1-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s;R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen, or R224 and R225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;Q represents,
or
; and
R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring or linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring. - The electroluminescent device according to claim 6, wherein the organic layer comprises one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds.
- The electroluminescent device according to claim 6, wherein the organic layer further comprises one or more metal(s) 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 electroluminescent device according to claim 6, which is a white light-emitting organic electroluminescent device wherein the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time.
- The electroluminescent device according to claim 6, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
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| EP2308843A1 (en) * | 2009-10-09 | 2011-04-13 | Samsung Mobile Display Co., Ltd. | Condensed-cyclic compound and organic light emitting diode including organic layer containing the condensed-cyclic compound |
| WO2011068204A1 (en) * | 2009-12-03 | 2011-06-09 | Jnc株式会社 | Benzo[c]carbazole compound that has substituent bearing pyridine ring, and organic electroluminescent element |
| US20120012826A1 (en) * | 2010-07-13 | 2012-01-19 | Samsung Mobile Display Co., Ltd. | Organic light-emitting device |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20100108924A (en) | 2010-10-08 |
| WO2010114264A3 (en) | 2010-11-25 |
| TW201105774A (en) | 2011-02-16 |
| KR101603070B1 (en) | 2016-03-14 |
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