CN103641831A - 新的有机电致发光化合物和使用该化合物的有机电致发光设备 - Google Patents
新的有机电致发光化合物和使用该化合物的有机电致发光设备 Download PDFInfo
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- CN103641831A CN103641831A CN201310559971.5A CN201310559971A CN103641831A CN 103641831 A CN103641831 A CN 103641831A CN 201310559971 A CN201310559971 A CN 201310559971A CN 103641831 A CN103641831 A CN 103641831A
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- organic electroluminescent
- compound
- alkyl
- group
- aryl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 163
- 239000000126 substance Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 15
- -1 amine compounds Chemical class 0.000 claims description 12
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 11
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 7
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 6
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 3
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 3
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 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
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 35
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000012153 distilled water Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 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 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 238000001816 cooling Methods 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
- 230000005525 hole transport Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- JNGKNTZYAKKNLQ-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1h-triazine Chemical compound N=1N(Cl)NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JNGKNTZYAKKNLQ-UHFFFAOYSA-N 0.000 description 1
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 1
- FRNLBIWVMVNNAZ-UHFFFAOYSA-N 2-iodonaphthalene Chemical compound C1=CC=CC2=CC(I)=CC=C21 FRNLBIWVMVNNAZ-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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- CEXRFZIDTXBRQO-UHFFFAOYSA-N C(CC1=CC2)C=CC1=CC2N(C(C1CC=C23)=C2NC(CC2)=C3c3c2cccc3)c2c1c(cccc1)c1cc2 Chemical compound C(CC1=CC2)C=CC1=CC2N(C(C1CC=C23)=C2NC(CC2)=C3c3c2cccc3)c2c1c(cccc1)c1cc2 CEXRFZIDTXBRQO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- UUESRJFGZMCELZ-UHFFFAOYSA-K aluminum;2-methylquinoline-8-carboxylate;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21 UUESRJFGZMCELZ-UHFFFAOYSA-K 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
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003943 azolyl 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
- 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000707 boryl group Chemical group B* 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
- 230000008859 change Effects 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VNICRWVQYFRWDK-UHFFFAOYSA-N naphthalen-2-ylhydrazine Chemical compound C1=CC=CC2=CC(NN)=CC=C21 VNICRWVQYFRWDK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明公开了一种新颖的有机电致发光化合物和包括该化合物的有机电致发光设备。所述有机电致化合物当用作OLED设备的有机电致发光材料的基质材料时，与常规基质材料相比，显示高的发光效率和优异的寿命性能。因此，它可用于制造具有非常好的工作寿命的OLED。
Description
本发明专利申请是国际申请号为PCT/KR2010/001647，国际申请日为2010年3月17日，进入中国国家阶段的申请号为201080022499.6，名称为“新的有机电致发光化合物和使用该化合物的有机电致发光设备”的发明专利申请的分案申请。
技术领域
本发明涉及新颖的有机电致发光化合物以及包含该化合物的有机电致发光设备。更具体地说，本发明涉及用作电致发光材料的新颖的有机电致发光化合物，以及使用它们作为基质（host）的有机电致发光设备。
背景技术
决定OLED（有机电致发光二极管）的发光效率的最重要因素是电致发光材料的类型。尽管到目前为止荧光材料已经广泛用作电致发光材料，但是从电致发光机理来看，开发磷光材料是理论上将发光效率提高最高到4倍的最好方法之一。
到目前为止，铱（III）络合物是众所周知的一种磷光材料，包括（acac）Ir（btp）2、Ir（ppy）3和Firpic，分别作为红色、绿色和蓝色磷光材料。具体来说，许多磷光材料目前已经在日本、欧洲和美国进行研究。
作为磷光发光材料的基质材料，到目前为止最广为人知的是4,4'-N,N'-二咔唑-联苯（biphenyl）（CBP），且已知已应用空穴阻挡层（例如BCP和BAlq）的具有高效率的OLED。先锋公司（日本）已经报道使用二（2-甲基-8-喹啉酚根（quinolinato））（对苯基苯酚根（phenolato））铝（III）（BAlq）衍生物作为基质的高性能的OLED。
尽管现有技术中的材料从发光性质来看具有优势，但是它们具有低的玻璃化转变温度以及非常差的热稳定性，所以这些材料往往会在气相沉积工艺过程中在高温和真空下发生变化。在OLED中，定义功率效率＝(π/电压)×电流效率。因此，功率效率与电压成反比，且功率效率应该较高以得到较低的OLED功率消耗。在实际中，使用磷光电致发光材料的OLED显示其电流效率（cd/A）比使用荧光EL材料的OLED明显更高。但是，在使用常规材料例如BAlq和CBP作为磷光材料的基质材料的情况下，在功率效率（1m/w）方面没有明显的优势，这是因为相比使用荧光材料的OLED具有更高的工作电压。而且，该OLED不能得到满意的设备寿命。
因此，需要开发稳定性和性能进一步改进的基质材料。
发明内容
发明技术问题的描述
本发明的发明人努力克服了常规技术的问题，从而发明了新颖的电致发光化合物来实现具有优异发光效率和明显延长的设备寿命的有机电致发光设备。
因此，本发明的目的是克服上述问题并提供包括骨架的有机电致发光化合物，以相比常规基质材料得到更高的发光效率、提高的设备寿命和合适的色坐标。
本发明的另一个目的是提供具有高效率和长寿命的有机电致发光设备，它使用该有机电致发光化合物作为电致发光材料。
解决问题的方法
具体地说，本发明涉及用化学式（1）-（5）之一表示的有机电致发光化合物以及包括该化合物的有机电致发光设备。由于本发明的有机电致发光化合物相比常规基质材料提供更好的发光效率和优异的寿命性能，因此可得到具有优异工作寿命的OLED。
[化学式1]
[化学式2]
[化学式3]
[化学式4]
[化学式5]
其中，
X和Y独立地选自N(Ar1),O和S，其中Ar1可相互不同，且当有两个或多个Ar1基团时，Ar1可表示为Ar1或Ar2；
Z1到Z8独立地选自C(Ar3)和N，其中Ar3可相互不同，且相邻的Ar3基团可连接在一起形成环；
Ar1和Ar2独立地选自(C1-C60)烷基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基和(C3-C60)杂芳基；
Ar3独立地选自氢,(C1-C60)烷基,卤素,氰基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基,(C1-C60)烷氧基,(C6-C60)芳氧基,(C3-C60)杂芳基,(C6-C60)芳硫基,(C1-C60)烷硫基,单-或二(C1-C30)烷氨基,单-或二(C6-C30)芳氨基,三(C1-C30)烷基甲硅烷基,二(C1-C30)烷基(C6-C30)芳基甲硅烷基,三(C6-C30)芳基甲硅烷基,单-或二(C6-C30)芳基硼烷基,单-或二(C1-C60)烷基硼烷基,硝基和羟基；以及
Ar1到Ar3的烷基,环烷基,杂环烷基,二环烷基,金刚烷基,烯基,炔基,芳基,烷氧基,芳氧基,杂芳基,芳硫基,烷硫基,烷氨基,芳氨基,三烷基甲硅烷基,二烷基芳基甲硅烷基,三芳基甲硅烷基,芳基硼烷基或烷基硼烷基可进一步由选自下组的一个或多个取代基取代：(C1-C60)烷基,卤素,氰基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基,(C1-C60)烷氧基,(C6-C60)芳氧基,P(=O)RaRb[Ra和Rb独立地表示(C1-C60)烷基或(C6-C60)芳基]取代的(C6-C60)芳基,(C3-C60)杂芳基,(C6-C60)芳基取代的(C3-C60)杂芳基,(C1-C60)烷基取代的(C3-C60)杂芳基,(C6-C60)芳基(C1-C60)烷基,(C6-C60)芳硫基,(C1-C60)烷硫基,单-或二(C1-C30)烷氨基,单-或二(C6-C30)芳氨基,三(C1-C30)烷基甲硅烷基,二(C1-C30)烷基(C6-C30)芳基甲硅烷基,三(C6-C30)芳基甲硅烷基,单-或二(C6-C30)芳基硼烷基,单-或二(C1-C60)烷基硼烷基,硝基和羟基,不包括这样的情况：X和Y都是N(Ar1)且Z1到Z8都是C(Ar3)。
本文所述的包括"(C1-C60)烷基"部分的取代基可包含1-60个碳原子，1-20个碳原子或1-10个碳原子。包括"(C6-C60)芳基"部分的取代基可包含6-60个碳原子，6-20个碳原子或6-12个碳原子。包括"(C3-C60)杂芳基"部分的取代基可包含3-60个碳原子，4-20个碳原子或4-12个碳原子。包括"(C3-C60)环烷基"部分的取代基可包含3-60个碳原子，3-20个碳原子或3-7个碳原子。包括"(C2-C60)烯基或炔基"部分的取代基可包含2-60个碳原子，2-20个碳原子或2-10个碳原子。
本发明的术语“烷基”包括直链或支链饱和单价烃基或其组合，它们可仅由碳原子和氢原子组成。术语“烷氧基”表示-O-烷基，其中烷基如上定义。
本文所述术语"芳基"表示由芳香烃除去一个氢原子后得到的有机基。芳基包括单环或稠环系统，芳基的每个环适当包含4-7个、优选5-6个环原子。也可包括两个或多个芳基通过化学键结合的结构。具体例子包括苯基、萘基、联苯基（biphenyl）、蒽基、茚基、芴基、菲基（phenanthryl）、苯并[9,10]菲基（triphenylenyl）、芘基、苝基（perylenyl）、
基（chrysenyl）、并四苯基（naphthacenyl）、荧蒽基（fluoranthenyl）等，但不限于此。
本文所述的术语"杂芳基"表示芳香环骨架原子中包含1-4个选自N、O和S的杂原子且剩余的芳香环骨架原子为碳原子的芳基。所述杂芳基可以是5-或6-元单环杂芳基或与一个或多个苯环稠合的多环杂芳基，且可以是部分饱和的。也可包括具有一个或多个通过化学键连接的杂芳基的结构。所述杂芳基可包括二价芳基，其杂原子氧化或季铵化形成N-氧化物、季铵盐等。具体的例子包括单环杂芳基例如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异
唑基、唑基、二唑基、三嗪基、四嗪基、三唑基、四唑基、呋咱基（furazanyl）、吡啶基、吡嗪基、嘧啶基、哒嗪基；多环杂芳基例如苯并呋喃基、苯并噻吩基、异苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异
唑基、苯并
唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基（cinnolinyl）、喹唑啉基、喹嗪基（quinolizinyl）、喹喔啉基（quinoxalinyl）、咔唑基、菲啶基（phenanthridinyl）、苯并间二氧杂环戊烯基（benzodioxolyl）；及其相应的N-氧化物（例如吡啶基N-氧化物、喹啉基N-氧化物）；及其季铵盐，但并不限于此。
本发明的有机电致发光化合物的例子可以是下述化学式之一表示的化合物：
其中：Ar1和Ar2如化学式（1）－（5）中所定义。
另外，本发明的有机电致发光化合物的例子可以是下述化学式之一表示的化合物：
其中：Ar1和Ar2如化学式（1）－（5）中所定义。
本发明的有机电致发光化合物的具体例子可以是下述化学式之一表示的化合物：
其中：Ar1和Ar2如化学式（1）－（5）中所定义。
更具体地说，Ar1和Ar2独立地表示苯基、1-萘基或2-萘基或下述化学式之一表示的取代基，但是它们不限于此。
本发明也提供了一种有机电致发光设备，它由第一电极、第二电极和插入所述第一电极和第二电极之间的至少一层有机层；其中所述有机层包括一种或多种化学式（1）-（5）之一表示的有机电致发光化合物。
本发明的有机电致发光设备的特征是有机层包括电致发光层，该电致发光层包括一种或多种化学式（1）-（5）之一表示的化合物作为电致发光基质以及一种或多种磷光掺杂剂。所述掺杂剂并没有具体限制。
本发明的有机电致发光设备还可包括一种或多种选自芳胺化合物和苯乙烯基芳胺化合物的化合物，以及一种或多种化学式（1）-（5）之一表示的有机电致发光化合物。
在本发明的有机电致发光设备中，所述有机层还可包括一种或多种选自元素周期表第1族、第2族、第四周期和第五周期过渡金属、镧系金属和D-过渡元素的金属或其络合物，以及一种或多种化学式（1）-（5）之一表示的有机电致发光化合物。所述有机层可包括电致发光层和电荷产生层。
除了上述有机电致发光化合物之外，所述有机电致发光设备也可包括一层或多层发蓝光、绿光或红光的有机电致发光层，以形成发白光的有机电致发光设备。
发明的有利效果
本发明的有机电致发光化合物用作OLED的有机电致发光材料的基质材料时显示出该材料具有优良的发光效率和很好的寿命性能，所以由该化合物可制造具有非常好工作寿命的OLED。
本发明的实施方式
还通过参照制备例和实施例进一步描述本发明，以说明本发明的代表性的有机电致发光化合物、其制备方法以及电致发光设备的发光性能，但是提供这些实施例仅用于更好地理解本发明的实施方式，而不是用来以任何方式限制本发明的范围。
制备例
制备例1：制备化合物(A)
制备化合物(A-1)
溴-2-硝基苯(30g,148.5mmol)、1-萘硼酸（1-naphtaleneboronic acid）(30.6g,178.2mmol),Pd(PPh3)4(5.14g,4.45mmol),2M K2CO3水溶液(297.01mmol),甲苯(500mL)和乙醇(200mL)的混合物在回流条件搅拌4小时。将混合物冷却到室温后，向其中加入蒸馏水。所得混合物用乙酸乙酯萃取，萃取物用硫酸镁干燥，并减压蒸馏。通过柱纯化得到化合物(A-1)(31g,124.3mmol,84.03%)。
制备化合物(A-2)
化合物（A-1）(31g,124.3mmol)和亚磷酸三乙酯(300mL)的混合物回流搅拌10小时。将混合物冷却到室温后，减压蒸馏掉有机溶剂。向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(A-2)(18g,82.84mmol,66.81%)。
制备化合物(A-3)
化合物(A-2)(18g,82.84mmol),l,5-二苯基-3-氯吡啶(26.4g,99.41mmol),Pd(OAc)2(1.85g,8.28mmol),P(t-bu)3(8.17ml,16.5mmol,在二甲苯中50%),NaOt-bu(23.8g,248.5mmol)和甲苯(500mL)的混合物回流搅拌12小时。将所述混合物冷却到室温后，向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(A-3)(19g,42.54mmol,51.36%)。
制备化合物(A-4)
向化合物（A-3）(19g,42.54mmol)溶于DMF（200mL）的溶液中加入NBS(8.33g,46.80mmol)。在室温放置10小时后，减压蒸馏掉有机溶剂。向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(A-4)(20g,38.06mmol,89.47%)。
制备化合物(A-5)
于-78℃向溶于THF（200mL）的化合物（A-4）溶液中缓慢加入n-buLi(15.22mL,38.06mmol,在己烷中2.5M）。搅拌1小时后，向其中加入硼酸三甲酯。所述混合物缓慢升温到室温，并搅拌12小时。向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(A-5)(8g,16.31mmol,42.86%)。
制备化合物(A-6)
化合物(A-5)(8g,16.31mmol),溴-2-硝基苯(3.95g,19.57mmol),Pd(PPh3)4(0.56g,0.48mmol),2M K2CO3水溶液(16mL,32.62mmol),甲苯(70mL)和乙醇(20mL)的混合物回流搅拌。根据与合成化合物（A-1）相同的步骤得到化合物（A-6）(7g,12.33mmol,75.62%)。
制备化合物(A-7)
化合物(A-6)(7g,12.33mmol)与亚磷酸三乙酯（100mL）混合，且根据与合成化合物（A-2）相同的步骤得到化合物（A-7）(4g,7.46mmol,58.33%).
制备化合物(A)
化合物(A-7)(4g,7.46mmol),碘苯(1.25mL,11.20mmol),铜粉(0.71g,11.20mmol),K2CO3(3.09g),18-冠-6(0.15g,0.59mmol)和1,2-二氯苯(100mL)的混合物回流搅拌15小时。将反应混合物冷却到室温后，减压蒸馏掉有机溶剂。向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物通过柱纯化得到化合物(A)(3.6g,5.88mmol,78.88%)。
制备例2：制备化合物(B)
制备化合物(B-1)
l,4-二溴-2,3-二硝基苯(20g,61.36mmol),1-萘硼酸(26g,153.42mmol),Pd(PPh3)4(3.54g,3.06mmol),2M K2CO3水溶液(90mmol),甲苯(200mL)和乙醇(100mL)的混合物在回流条件搅拌10小时。将所述反应混合物冷却到室温后，向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(B-1)(22g,52.32mmol,85.28%)。
制备化合物(B-2)
化合物(B-1)(22g,52.32mmol)和亚磷酸三乙酯(200mL)混合，并在180℃搅拌。根据与合成化合物（A-2）相同的步骤得到化合物（B-2）(10g,28.05mmol,53.95%).
制备化合物(B-3)
化合物(B-2)(10g,28.05mmol),2-碘萘(7.1g，28.05mmol),铜粉(2.67g,42.08mmol),K2CO3(11.63g，84.17mmol),18-冠-6(0.59g,2.24mmol)和1,2-二氯苯(100mL)的混合物于190℃回流搅拌20小时。冷却到室温后，减压蒸馏掉有机溶剂。向其中加入蒸馏水，且所述混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(B-3)(4g,8.28mmol,29.60%)。
制备化合物(B)
向包含溶于DMF（20mL）的NaH(0.49g,12.43mmol,在矿物油中的60%分散液)溶液的反应容器中加入溶于DMF（20mL）的化合物（B-3）(4g,8.28mmol)的溶液。1小时后，将2-氯-4,6-二苯基三嗪(2.66g,9.94mmol)溶于DMF（20mL）的溶液加入其中。搅拌12小时后，加入蒸馏水，且制得的固体减压过滤。从乙酸乙酯和DMF重结晶得到化合物(B)(3.5g,4.90mmol,59.21%)。
制备例3：制备化合物(C)
制备化合物（C-1）
向1,2-环己基二酮(42.52g,379.26mmol)溶于乙醇（1000mL）的溶液中缓慢加入2-萘基肼(20g,126.42mmol)。向其中加入乙酸(0.28mL,5.05mmol)，且将混合物加热到40℃。2小时后，冷却所述混合物，并向其中加入蒸馏水。所制得的固体减压过滤得到化合物（C-1）(17g,67.37mmol,53.47%)。
制备化合物(C-2)
向化合物（C-1）(17g,67.37mmol)溶于乙酸(100mL)的溶液中加入三氟乙酸(10mL)。在室温搅拌2小时后，向其中加入蒸馏水。混合物用NaOH水溶液中和，并用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(C-2)(11g,46.75mmol,69.39%)。
制备化合物(C-3)
根据与合成化合物（B-3）相同的步骤，得到化合物（C-3）(10g,32.11mmol,68.69%)。
制备化合物(C-4)
根据与合成化合物（C-1）相同的步骤，得到化合物（C-4）(12g,29.88mmol,93.07%)。
制备化合物(C-5)
根据与合成化合物（C-2）相同的步骤，得到化合物（C-5）(6g,15.68mmol,52.50%)。
制备化合物(C)
根据与合成化合物（B）相同的步骤，得到化合物（C）(5g,8.14mmol,51.95%)。
制备例4：制备化合物(D)
制备化合物(D-2)
根据与合成实施例（A-1）相同的步骤，但使用化合物（D-1）得到化合物（D-2）(11g,38.02mmol,89.22%).
制备化合物(D-3)
根据与合成化合物（A-2）相同的步骤得到化合物（D-3）(8g,31.09mmol,81.78%)。
制备化合物(D)
根据与合成化合物（B）相同的步骤得到化合物（D）(6g,12.30mmol,38.70%)。
制备例5：制备化合物E和F
制备化合物(E-2)
根据与合成化合物（A-1）相同的步骤，但使用化合物（E-1）得到化合物（E-2）(15g,51.85mmol,86.51%)。
制备化合物(E-3)
根据与合成化合物（A-2）相同的步骤，得到化合物（E-3）(6g,23.31mmol,44.97%)。
制备化合物(E)
根据与合成化合物（B）相同的步骤，得到化合物（E）(5g,10.25mmol,43.99%)。
制备化合物(F-1）
根据与合成化合物（A-2）相同的步骤，得到化合物（F-1）(3g,11.65mmol,22.48%)。
制备化合物(F)
根据合成化合物（B）相同的步骤，得到化合物（F）(3g,6.15mmol,52.81%)。
制备例6：制备化合物(G)和（H）
制备化合物(G-1)
咔唑(20g,119.6mmol),碘苯(20mL，179.41mmol),铜(11.4g,179.41mmol),K2CO3(49g，358.8mmol),18-冠-6(2.5g,9.56mmol)和1,2-二氯苯(100mL)的混合物于190℃搅拌12小时。冷却到室温后，反应混合物减压蒸馏。向其中加入蒸馏水，且所得混合物用乙酸乙酯萃取。萃取物用硫酸镁干燥，且减压蒸馏。通过柱纯化得到化合物(G-1)(22g,90.42mmol，75.60%)。
制备化合物(G-2)
根据与合成化合物（A-4）相同的步骤，得到化合物（G-2）(25g,77.59mmol,85.81%)。
制备化合物(G-3)
根据与合成化合物（A-5）相同的步骤，得到化合物（G-3）(11g,38.31mmol,49.37%)。
制备化合物(G-4)
根据与合成化合物（A-1）相同的步骤，得到化合物（G-4）(12g,32.84mmol,85.72%)。
制备化合物(G-5)
根据与合成化合物（A-2）相同的步骤，进行反应4小时得到化合物（G-5）(6g,17.99mmol,54.80%)。
制备化合物(G)
根据与合成化合物（B）相同的步骤，得到化合物（G）(7g,12.39mmol,68.91%)。
制备化合物(H-1)
根据与合成化合物（A-2）相同的步骤，进行反应4小时得到化合物（H-1）(2g,5.99mmol,18.26%)。
制备化合物(H)
根据与合成化合物（B）相同的步骤，得到化合物（H）(1.7g,3.01mmol,50.26%)。
根据制备例（1）-（6）的步骤制备有机电致发光化合物(TA,TB和TC)。这些制得的有机电致发光化合物的取代基（Ar1和Ar2）以及这些化合物的1H NMR和MS/FAB数据列在下表1和2中。
表1
表2
[实施例1-10]使用本发明的有机电致发光化合物制造OLED
使用本发明的电致发光化合物制造OLED设备。
首先，将由玻璃制成的用于OLED的透明电极ITO薄膜(15Ω/□)（购自三星康宁公司）依次用三氯乙烯、丙酮、乙醇和蒸馏水进行超声波清洗，并在使用之前储存在异丙醇中。
然后，将ITO基片装在真空气相沉积设备的基片夹（folder）中，将由以下化学结构式表示的4,4',4"-三(N,N-(2-萘基)-苯基氨基)三苯胺(2-TNATA)置于真空气相沉积设备的小室(cell)中，然后排气至室内真空度最高达到10-6托。对小室施加电流，使2-TNATA蒸发，从而在ITO基片上气相沉积60纳米厚度的空穴注入层。
然后，在该真空气相沉积设备的另一个小室中加入N,N'-二(α-萘基)-N,N'-二苯基-4,4'-二胺(NPB)，对小室施加电流以蒸发NPB，从而在空穴注入层上气相沉积20纳米厚度的空穴输运层。
向气相沉积设备的一个小室中加入本发明的化合物（它已经在10-6托下经过真空升华纯化）（例如，化合物TA8-H4-H2），且将电致发光掺杂剂（例如，化合物（piq）2Ir（acac））加入另一个小室中。两种材料以不同的速率蒸发以4-10摩尔％的浓度进行掺杂，从而在空穴输运层上气相沉积30纳米厚度的电致发光层。
然后，将以下结构式表示的三(8-羟基喹啉)铝(III)(Alq)气相沉积为20纳米厚度的电子输运层，将8-羟基喹啉锂(lithium quinolate)(Liq)气相沉积为1-2纳米厚的电子注入层。然后，采用另一个真空气相沉积设备，气相沉积150纳米厚的Al阴极，制造OLED。
[实施例11-20]使用本发明的电致发光化合物制造OLED
根据与实施例1-10的OLED相同的步骤制造OLED，但使用本发明的化合物（例如化合物TA4-H4-H4）作为基质材料以及下述化学式表示的有机铱络合物(Ir(ppy)3)作为电致发光掺杂剂。
[比较例1和2]使用常规电致发光材料制造OLED
根据与本发明实施例1和11相同的步骤制造OLED，但是真空气相沉积设备的另一个小室中加入二（2-甲基8-喹啉酚根)(对苯基苯酚根)铝(III)(BAlq),而不是本发明的电致发光化合物，作为基质材料。
在1000cd/cm2测量实施例1-10和实施例11-20（它们包括本发明的有机电致发光化合物）以及比较例1和2（它们包括常规电致发光化合物）制造的OLED的工作电压和功率效率，结果列在表3和4中。
由表3和4可知，本发明开发的有机电致发光化合物在设备性能方面相比常规材料具有优异的性能。
表3
表4
由表3可知，与常规材料相比，本发明开发的化合物在发光性质方面显示优异的性能。与用常规材料制造的比较例1的设备相比，本发明制造的设备显示优异的电流性能，从而将工作电压降低1V或更多。与比较例1的设备相比，它们还显示电流效率性能至少为前者的1.4倍，这是因为发光性能得到明显提高。
由表4可知，当本发明开发的化合物用作绿色电致发光的基质时，与比较例2的设备相比，所述设备因为它们具有优异的发光性能而显示至少为前者的1.6倍的高得多的功率效率。与常规材料相比，优异的发光性能得到确认。特别是，与比较例1的设备相比，实施例14的设备可在降低2.7V的电压下工作，实施例17的设备显示工作电压为5.5V，在1000cd/m2的功率效率为15.9lm/。
因此，使用本发明电致发光化合物作为基质材料发出红光或绿光的设备显示优异发光性能，同时降低工作电压，这样导致特别是发绿光的设备的功率效率增加5.1-7.7lm/W，结果是改善功率消耗。
Claims (10)
1.一种由下述化学式1-5之一表示的有机电致发光化合物：
化学式2
其中：
X和Y独立地选自N(Ar1),O和S，其中Ar1可相互不同，且当有两个或多个Ar1基团时，Ar1可表示为Ar1或Ar2；
Z1到Z8独立地选自C(Ar3)和N，其中Ar3可相互不同，且相邻的Ar3基团可连接在一起形成环；
Ar1和Ar2独立地选自(C1-C60)烷基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基和(C3-C60)杂芳基；
Ar3独立地选自氢,(C1-C60)烷基,卤素,氰基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基,(C1-C60)烷氧基,(C6-C60)芳氧基,(C3-C60)杂芳基,(C6-C60)芳硫基,(C1-C60)烷硫基,单-或二(C1-C30)烷氨基,单-或二(C6-C30)芳氨基,三(C1-C30)烷基甲硅烷基,二(C1-C30)烷基(C6-C30)芳基甲硅烷基,三(C6-C30)芳基甲硅烷基,单-或二(C6-C30)芳基硼烷基,单-或二(C1-C60)烷基硼烷基,硝基和羟基；以及
Ar1到Ar3的烷基,环烷基,杂环烷基,二环烷基,金刚烷基,烯基,炔基,芳基,烷氧基,芳氧基,杂芳基,芳硫基,烷硫基,烷氨基,芳氨基,三烷基甲硅烷基,二烷基芳基甲硅烷基,三芳基甲硅烷基,芳基硼烷基或烷基硼烷基可进一步由选自下组的一个或多个取代基取代：(C1-C60)烷基,卤素,氰基,(C3-C60)环烷基,包含一个或多个选自N、O、S、Si和P的杂原子的5-或6-元杂环烷基,(C7-C60)二环烷基,金刚烷基,(C2-C60)烯基,(C2-C60)炔基,(C6-C60)芳基,(C1-C60)烷氧基,(C6-C60)芳氧基,P(=O)RaRb[Ra和Rb独立地表示(C1-C60)烷基或(C6-C60)芳基]取代的(C6-C60)芳基,(C3-C60)杂芳基,(C6-C60)芳基取代的(C3-C60)杂芳基,(C1-C60)烷基取代的(C3-C60)杂芳基,(C6-C60)芳基(C1-C60)烷基,(C6-C60)芳硫基,(C1-C60)烷硫基,单-或二(C1-C30)烷氨基,单-或二(C6-C30)芳氨基,三(C1-C30)烷基甲硅烷基,二(C1-C30)烷基(C6-C30)芳基甲硅烷基,三(C6-C30)芳基甲硅烷基,单-或二(C6-C30)芳基硼烷基,单-或二(C1-C60)烷基硼烷基,硝基和羟基,
不包括这样的情况：X和Y都是N(Ar1)且Z1到Z8都是C(Ar3)。
2.如权利要求1所述的有机电致发光化合物，其特征在于，所述化合物选自下述化合物：
其中：Ar1和Ar2如权利要求1所定义。
3.如权利要求1所述的有机电致发光化合物，其特征在于，所述化合物选自下述化合物：
其中：Ar1和Ar2如权利要求1所定义。
4.如权利要求1所述的有机电致发光化合物，其特征在于，所述化合物选自下述化合物：
其中：Ar1如权利要求1所定义。
5.一种有机电致发光设备，所述设备包括包括权利要求1-4中任一项所述的有机电致发光化合物。
6.如权利要求5所述的有机电致发光设备，其特征在于，所述设备包括第一电极；第二电极；以及插入所述第一电极和第二电极之间的一层或多层有机层，所述有机层包括一种或多种权利要求1-4中任一项所述的有机电致发光化合物以及一种或多种磷光掺杂剂。
7.如权利要求6所述的有机电致发光设备，其特征在于，所述有机层还包括一种或多种选自芳胺化合物和苯乙烯基芳胺化合物的胺化合物。
8.如权利要求6所述的有机电致发光设备，其特征在于，所述有机层还包括一种或多种选自元素周期表第1族、第2族、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的金属或者由它们形成的络合物。
9.如权利要求6所述的有机电致发光设备，其特征在于，所述有机层包括电致发光层和电荷产生层。
10.如权利要求6所述的有机电致发光设备，其特征在于，所述设备是发白光的有机电致设备，所述有机层同时包括一层或多层发蓝光、红光或绿光的有机电致发光层。
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| CN102482571A (zh) | 2012-05-30 |
| CN105001224A (zh) | 2015-10-28 |
| JP6153976B2 (ja) | 2017-06-28 |
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| JP6073933B2 (ja) | 2017-02-01 |
| CN103641832A (zh) | 2014-03-19 |
| CN105294712A (zh) | 2016-02-03 |
| CN103641830B (zh) | 2017-04-12 |
| JP2016001749A (ja) | 2016-01-07 |
| JP6114763B2 (ja) | 2017-04-12 |
| WO2010107244A2 (en) | 2010-09-23 |
| JP2015122508A (ja) | 2015-07-02 |
| JP2017008061A (ja) | 2017-01-12 |
| CN103641830A (zh) | 2014-03-19 |
| CN105176523A (zh) | 2015-12-23 |
| CN103555322A (zh) | 2014-02-05 |
| CN103524510A (zh) | 2014-01-22 |
| JP2012520872A (ja) | 2012-09-10 |
| JP2015120702A (ja) | 2015-07-02 |
| WO2010107244A3 (en) | 2010-12-09 |
| JP6356183B2 (ja) | 2018-07-11 |
| CN103524510B (zh) | 2016-02-10 |
| CN105176523B (zh) | 2017-10-10 |
| CN103555322B (zh) | 2016-08-17 |
| TW201105768A (en) | 2011-02-16 |
| TW201522570A (zh) | 2015-06-16 |
| KR101511072B1 (ko) | 2015-04-10 |
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