TWI385236B - 新穎有機電致發光化合物及使用該化合物之有機電致發光裝置 - Google Patents
新穎有機電致發光化合物及使用該化合物之有機電致發光裝置 Download PDFInfo
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- TWI385236B TWI385236B TW097151335A TW97151335A TWI385236B TW I385236 B TWI385236 B TW I385236B TW 097151335 A TW097151335 A TW 097151335A TW 97151335 A TW97151335 A TW 97151335A TW I385236 B TWI385236 B TW I385236B
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- Prior art keywords
- group
- alkyl
- aryl
- heteroaryl
- morpholinyl
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- 150000001875 compounds Chemical class 0.000 title claims description 129
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 134
- -1 N-morpholinyl group Chemical group 0.000 claims description 131
- 125000005842 heteroatom Chemical group 0.000 claims description 107
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 102
- 125000001072 heteroaryl group Chemical group 0.000 claims description 101
- 229910052760 oxygen Inorganic materials 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 229910052717 sulfur Inorganic materials 0.000 claims description 99
- 239000010410 layer Substances 0.000 claims description 73
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 62
- 150000002367 halogens Chemical class 0.000 claims description 55
- 125000003282 alkyl amino group Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 41
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 40
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
- 125000001769 aryl amino group Chemical group 0.000 claims description 39
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 37
- 239000007983 Tris buffer Substances 0.000 claims description 37
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 36
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 32
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 32
- 125000002950 monocyclic group Chemical group 0.000 claims description 31
- 125000002723 alicyclic group Chemical group 0.000 claims description 30
- 125000003367 polycyclic group Chemical group 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 15
- 238000005401 electroluminescence Methods 0.000 claims description 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 13
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 12
- VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000005110 aryl thio 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
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004568 thiomorpholinyl 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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000000732 arylene group Chemical group 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
- 239000010931 gold Substances 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000005416 organic matter Substances 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 21
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000007740 vapor deposition Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003943 azolyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 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
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SQTPFYJEKHTINP-UHFFFAOYSA-N 2-bromophenanthrene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3C=CC2=C1 SQTPFYJEKHTINP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001786 chalcogen compounds Chemical class 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003446 ligand Substances 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
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- 239000011701 zinc Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
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- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-UHFFFAOYSA-N 0.000 description 1
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-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
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 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
- 125000003277 amino group Chemical group 0.000 description 1
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 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
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- QDOAVFZGLCBVQL-UHFFFAOYSA-N bismuth Chemical compound [Bi].[Bi].[Bi] QDOAVFZGLCBVQL-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 150000004697 chelate complex Chemical class 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
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling 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
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- VNHHZBXVGVODOD-UHFFFAOYSA-N tert-butylhydrazine hydrazine Chemical compound C(C)(C)(C)NN.NN VNHHZBXVGVODOD-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
本發明係關於新穎有機電致發光化合物及包括該化合物之有機電致發光裝置。
顯示裝置當中，相較於LCD裝置，電致發光裝置(EL裝置(electroluminescence device)為具有廣角視野、優異對比及快速反應速率之優點的自發光(self-luminescent)顯示裝置。Eastman Kodak於1987年首先發展出利用低分子量芳香族二胺及鋁錯合物作為材料以形成EL層之有機EL裝置[Appl. Phys. Lett. 51,913,1987]。
有機EL裝置為其中當施加電荷到形成於電子注入電極(陰極)及電洞注入電極(陽極)間的有機膜時，電子與電洞配對然後遞減而發光之裝置。可在透明可撓性基板(例如塑膠)上形成有機EL裝置。相較於電漿顯示器面板或無機EL顯示器，有機EL裝置可在相對較低功率消耗之較低電壓(不超過10伏特(V))下操作但仍具優異的色純度。
決定有機EL裝置之發光效率、壽命等之最重要因素為電致發光材料。該電致發光材料需要的數種性質包含：該材料需具有在固態中高螢光量子產率及電子和電洞之高遷移率、該材料在真空氣相沉積期間不易分解、以及該材料係形成均勻及安定的薄膜。
有機電致發光材料一般可分類成高分子材料及低分子材料。從分子結構而言，低分子材料包含金屬錯合物及不含金屬之純有機電致發光材料。此種電致發光材料包含螯合錯合物，例如參(8-羥基喹啉)鋁錯合物(tris(8-quinolinolato)aluminum complex)、香豆素(coumarin)衍生物、四苯基丁二烯衍生物、雙(苯乙烯基伸芳基)衍生物、二唑衍生物。由彼等材料可獲得從藍色到紅色可見光區的光發射已被報導過。
為了實現全彩OLED顯示器，係利用三種EL材料(紅色、綠色及藍色)，且發展出具有高效率和長壽命之EL材料係主要的目的，以增強整體有機電致發光的特徵。EL材料可依功能區分成主體(host)材料及摻雜劑材料。一般咸知具有最優異EL性能之裝置結構可製造成具有藉由摻雜摻雜劑到主體材料而製得的EL層。目前，發展具有高效率及長壽命之有機EL裝置已為當務之急，特別是考慮到從中型到大型尺寸的OLED面板時，亟需發展出相較於傳統EL材料具有更好的EL性質之材料。
從此觀點，主體材料之發展為應該被提出之重要因素之一。該主體材料(作為固態溶劑及能量傳遞者(deliverer))之所欲性質為能夠在真空中氣相沉積之高純度及適當分子量。此外，應具高玻璃轉移溫度及熱分解溫度以確保熱安定性。再者，主體材料應具有高電化學安定性以提供長壽命。其應易形成非晶質薄膜，對其他相鄰材料具高黏著性而不會發生層間遷移。
同時，關於傳統藍色材料。自Idemitsu-Kosan發展雙-二苯基乙烯基-聯苯(diphenylvinyl-biphenyl,DPVBi)(化學式a)以來，許多材料已被開發及商品化。除Idemitsu-Kosan之藍色材料系統外，亦已知二萘基蒽(DNA，化學式b)、肆(第三丁基)苝(化學式c)系統等。然而，關於這些材料應要進行廣泛研究及發展。
Idemitsu-Kosan之桂醯基(distryl)化合物系統(已知係目前為止具有最高效率者)具有6流明/瓦(1m/W)之功率效率及超過30,000小時之有用裝置壽命。然而，當將該系統應用到全彩顯示器時，由於在操作時間期間之色純度的下降，壽命僅為幾千小時。從發光效率之觀點觀察，在藍色電致發光之例中，若電致發光波長往較長波長些許移動會變得有利。然而，因為藍色色純度不足，故不易將該材料施用於高品質之顯示器。此外，由於色純度、效率及熱安定性之問題，因此亟需研究及開發該等材料。
對具有高效率及長壽命之主體材料而言，已發展含有不同骨架(backbone)之不同物質，例如雙(螺二茀)-蔥(dispiro-fluorene-anthracene,TBSA)、參-螺二茀(ter-spirofluorene,TSF)及雙-聯伸三苯(bitriphenylene,BTP)，但是它們在色純度及發光效率之條件係為不足。
慶尚國立大學(Gyeongsang National University)及三星電管(Samsung SDI)(Kwon,S. K. et al., Advanced Materials,2001,13,1690；日本專利公開案第JP 2002121547號)所報導之化合物TBSA顯示在7.7伏特(V)具3燭光/安培(cd/A)之發光效率，及(0.15，0.11)之相對佳的色度座標，但該化合物係用作為單層之材料之實例，不適合實際使用。
國立台灣大學(Wu,C. C. et al.,Advanced Materials,2004,16,61；美國專利公開號第US 2005040392號)所報導之化合物TSF顯示5.3%之相對佳的外部量子效率，但實際使用仍為不足。
台灣國立清華大學(Cheng,C. H. et al.,Advanced Materials,2002,14,1409；美國專利公開號第US 2004076852號)所報導之化合物BTP顯示2.76cd/A之發光效率，及(0.16，0.14)之相對佳的色度座標，但實際使用仍為不足。
如上述，傳統材料係藉由單層而組成，非形成主體-摻雜劑薄層，且從色純度及效率方面而言係難以被實際使用。傳統材料係缺乏與其長壽命有關的可靠數據。
同時，根據三井化學(Mitsui Chemicals)(日本)之專利申請案(美國專利公告號第US 7,166,240號)，下示之化合物在390至430nm具有吸收光譜，具有4.6cd/A之發光效率。然而，基於這些數據，具有上述吸收波長範圍之化合物，預期為帶綠的藍色之電致發光性，且該專利公告案指出該顏色為帶藍的綠色。
具體而言，該專利公告案之對稱結構不可能為純藍色的具體實例，且此無法提供純藍光之材料無法實際應用到全彩顯示器。
因此，本發明之第一目的係克服上述問題，並提供一種有機電致發光化合物，相較於傳統主體材料，該化合物包括優異的骨架以獲得較佳發光效率、裝置壽命及適當色座標。
本發明之第二目的係藉由使用該有機電致發光化合物作為EL材料而提供一種高效率及長壽命之有機電致發光裝置。
第三目的係提供一種在電致發光層中使用該有機EL化合物之有機EL裝置。
第四目的係提供一種包括該有機電致發光化合物之太陽能電池。
因此，本發明係有關於化學式(1)表示之有機電致發光化合物，及包括該化合物之有機電致發光裝置。本發明之有機電致發光化合物呈現高發光效率及材料之優異色純度及壽命性質，因此可從此化合物製造具有極優異操作壽命之OLED。
其中，L1
表示(C6-C60)伸芳基或含有一個或多個選自N、O及S之雜原子之(C3-C60)雜伸芳基，或選自下列結構之二價基團：
L2
及L3
獨立地表示化學鍵、或(C1-C60)伸烷基氧基、(C1-C60)伸烷基硫基、(C6-C60)伸芳基氧基、(C6-C60)伸芳基硫基、(C6-C60)伸芳基或含有一個或多個選自N、O及S之雜原子之(C3-C60)雜伸芳基；
Ar1
表示NR41
R42
、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、金剛烷基、(C7-C60)雙環烷基、或選自下列結構之取代基：
R1
至R11
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R1
至R11
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環；
R21
至R31
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R21
至R31
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環；
R41
及R42
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R41
及R42
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基相鍵聯，以形成脂環、或單環或多環之芳香環；
R51
至R62
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R51
至R62
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環；
X及Y獨立地表示化學鍵、或-(CR71
R72
)m-、-N(R73
)-、-S-、-O-、-Si(R74
)(R75
)-、-P(R76
)-、-C(=O)-、-B(R77
)-、-In(R78
)-、-Se-、-Ge(R79
)(R80
)、-Sn(R81
)(R82
)-、-Ga(R83
)-或-(R84
)C=C(R85
)-；
R71
至R85
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R71
及R72
、R74
及R75
、R79
及R80
、R81
及R82
、或R84
及R85
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基相鍵聯，以形成脂環、或單環或多環之芳香環；
L1
至L3
之伸芳基或雜伸芳基、Ar1
之芳基或雜芳基、或R1
至R11
、R21
至R31
、R41
、R42
、R51
至R62
、及R71
至R85
之烷基、芳基、雜芳基、雜環烷基、環烷基、三烷基矽烷基、二烷基芳基矽烷基、三芳基矽烷基、烯基、炔基、烷基胺基或芳基胺基可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、鹵(C1-C60)烷基、(C6-C60)芳基、含有或不含有(C6-C60)芳基取代基之含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基、羥基、、
m為1至4之整數；及
x為1至4之整數。
參閱圖式，第1圖為本發明之OLED之剖面圖，OLED包括玻璃1、透明電極2、電洞注入層3、電洞傳輸層4、電致發光層5、電子傳輸層6、電子注入層7及鋁(Al)陰極8。
此處所述術語“烷基”及任何包含“烷基”部分之取代基係包含直鏈及分枝鏈烷基兩者。
此處所述術語“芳基”意指經由自芳香烴去除一個氫原子後所得之有機基團。各環包括含有4至7個環原子(較佳為含有5至6個環原子)之單環或稠合環系。具體實施例包含，但不限於苯基、萘基、聯苯基、蒽基、四氫萘基、茚基、薄基、菲基、聯伸三苯基(triphenylenyl)、芘基(pyrenyl)、苝基(perylenyl)、蒯基(chrysenyl)、稠四苯基(naphthacenyl)及丙二烯合茀基(fluoranthenyl)。
此處所述術語“雜芳基”意指具有作為芳香環骨架原子之1至4個雜原子以及作為維持芳香環骨架原子用之碳原子的芳基，其中該雜原子係選自N、O及S。雜芳基可為5員或6員單環雜芳基或與一個或多個苯環稠合之多環雜芳基，且該雜芳基可為部分飽和。雜芳基可包括二價芳基，該二價芳基雜原子可被氧化或四級化(quaternized)以形成N-氧化物(N-oxide)及四級鹽。具體實施例包括，但不限於單環雜芳基例如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基、唑基、二唑基、三基、四基、三唑基、四唑基、呋呫基(furazanyl)、吡啶基、吡基、嘧啶基、嗒基；多環雜芳基例如苯并呋喃基、苯并噻吩基、異苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異唑基、苯并唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹啉基、咔唑基、啡啶基及苯并二呃基(benzodioxolyl)；及對應的N-氧化物(例如吡啶基N-氧化物、喹啉基N-氧化物)及其四級鹽類。
化學式(1)之萘基可為1-萘基或2-萘基；蒽基可為1-蒽基、2-蒽基或9-蒽基；及茀基可為1-薄基、2-茀基、3-茀基、4-茀基或9-薄基。
此處所述包括“(C1-C60)烷基”部分之取代基可包含1至60個碳原子、1至20個碳原子、或1至10個碳原子。包括“(C6-C60)芳基”部分之取代基可包含6至60個碳原子、6至20個碳原子、或6至12個碳原子。包括“(C3-C60)雜芳基”部分之取代基可包含3至60個碳原子、4至20個碳原子、或4至12個碳原子。包括“(C3-C60)環烷基”部分之取代基可包含3至60個碳原子、3至20個碳原子、或3至7個碳原子。包括“(C2-C60)烯基或炔基”部分之取代基可包含2至60個碳原子、2至20個碳原子、或2至10個碳原子。
L1
可選自，但不限於下列結構。
其中，X及Y獨立地表示-(CR71
R72
)m
-、-N(R73
)-、-S-、-O-、-Si(R74
)(R75
)-、-P(R76
)-、或-(R84
)C=C(R85
)-；
R71
至R76
、R84
、R85
及m係如化學式(1)中所定義；
R91
至R120
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R91
至R120
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環。
更具體言之，L1
係選自，但不限於下列結構。
其中，R121
至R134
獨立地表示氫、氘、(C1-C60)烷基或(C6-C60)芳基；
R121
至R134
之烷基或芳基可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、鹵(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基及羥基。
基團可選自，但不限於下列結構。
其中，X及Y獨立地表示-(CR71
R72
)m
-、-N(R73
)-、-S-、-O-、-Si(R74
)(R75
)-、-P(R76
)-、或-(R84
)C=C(R85
)-；R71
至R76
、R84
、R85
及m係如化學式(1)中所定義；R201
及R202
獨立地表示氫、氘、(C1-C60)烷基、(C3-C60)環烷基、(C6-C60)芳基或含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基；R203
至R228
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基；R201
、R202
及R203
至R228
之烷基、芳基、雜芳基、雜環烷基、環烷基、三烷基矽烷基、二烷基芳基矽烷基、三芳基矽烷基、烯基、炔基、烷基胺基或芳基胺基可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、鹵(C1-C60)烷基、(C6-C60)芳基、含有或不含有(C6-C60)芳基取代基之含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基；
R201
、R202
及R203
至R228
之烷基、芳基、雜芳基、雜環烷基、環烷基、三烷基矽烷基、二烷基芳基矽烷基、三芳基矽烷基、烯基、炔基、烷基胺基或芳基胺基可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、鹵(C1-C60)烷基、(C6-C60)芳基、含有或不含有(C6-C60)芳基取代基之含有一個或多個選自N、O及S之雜原子之(C3-C60)雜芳基、N-嗎啉基、硫代N-嗎啉基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基氧基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基及羥基。
具體言之，基團係獨立地選自，但不限於下列結構。
R1
至R11
獨立地表示氫、氘、氟、氯、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、苯甲基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第三丁氧基、正戊氧基、異戊氧基、正己氧基、正庚氧基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、N-嗎啉基、硫代N-嗎啉基、嗎啉基、硫代嗎啉基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、二甲基苯基矽烷基、三苯基矽烷基、雙環[2.2.1]庚基、雙環[2.2.2]辛基、雙環[5.2.0]壬基、雙環[4.2.2]癸基4-戊基雙環[2.2.2]辛基、乙烯基、苯基乙烯基、乙炔基、苯基乙炔基、氰基、甲基硫基、苯基氧基、苯基硫基、甲氧基羰基、乙氧基羰基、第三丁氧基羰基、甲基羰基、乙基羰基、苯甲基羰基、苯基羰基、羧基、硝基或羥基。
本發明之有機電致發光化合物可由下列化合物具體例示，但不限於此。
本發明之有機電致發光化合物可依據反應流程圖(1)或(2)而製備，但不限於此。
反應流程圖(1)
反應流程圖(2)
其中，R1
至R11
、L1
、L2
、L3
、Ar1
及x係如化學式(1)中所定義。
本發明亦提供一種有機太陽能電池，其包括一種或多種化學式(1)表示之有機電致發光化合物。
本發明提供一種有機電致發光裝置，其包括第一電極；第二電極；及介於該第一電極與第二電極間之至少一層有機層；其中，該有機層包括一種或多種化學式(1)表示之有機電致發光化合物。該有機電致發光化合物係用作為電致發光層之主體材料。
再者，該有機層包括電致發光層，其除了包括一種或多種化學式(1)表示之有機電致發光化合物外，復包括一種或多種摻雜劑。應用於本發明之有機電致發光裝置之摻雜劑並未特別限制。
應用於本發明之有機電致發光裝置之摻雜劑較佳係選自化學式(2)至(4)之一者表示之化合物。
其中，R301
至R304
獨立地表示氫、氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C4-C60)雜芳基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C6-C60)芳基氧基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基或羥基，或R301
至R304
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環；
R301
至R304
之烷基、烯基、炔基、環烷基、雜環烷基、芳基、雜芳基、芳基矽烷基、烷基矽烷基、烷基氧基、芳基氧基、芳基硫基、烷基胺基、芳基胺基，或R301
至R304
藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基而與相鄰取代基相鍵聯所形成之脂環、或單環或多環之芳香環可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C4-C60)雜芳基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C6-C60)芳基氧基、(C1-C60)烷基氧基、(C1-C60)烷基硫基、(C6-C60)芳基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基及羥基；
其中，Ar11
及Ar12
獨立地表示(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、O及S之雜原子之(C4-C60)雜芳基、(C6-C60)芳基胺基、(C1-C60)烷基胺基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、或(C3-C60)環烷基，或Ar11
及Ar12
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基相鍵聯，以形成脂環、或單環或多環之芳香環；
當a為1，Ar13
表示(C6-C60)芳基、(C4-C60)雜芳基、或選自下列結構之取代基：
當a為2，Ar13表示(C6-C60)伸芳基、含有一個或多個選自N、O及S之雜原子之(C4-C60)雜伸芳基、或選自下列結構之取代基：
其中，Ar21
及Ar22
獨立地表示(C6-C60)伸芳基或含有一個或多個選自N、O及S之雜原子之(C4-C60)雜伸芳基；
R311
至R315
獨立地表示氫、氘、(C1-C60)烷基或(C6-C60)芳基；
b為1至4之整數；c為整數0或1；d為整數0或1；及
Ar11
及Ar12
之烷基、芳基、雜芳基、芳基胺基、烷基胺基、環烷基或雜環烷基；Ar13
之芳基、雜芳基、伸芳基或雜伸芳基；Ar21
及Ar22
之伸芳基或雜伸芳基；或R311
至R315
之烷基或芳基可進一步經一個或多個選自下列之取代基所取代：氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、含有一個或多個選自N、0及S之雜原子之(C4-C60)雜芳基、含有一個或多個選自N、0及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C6-C60)芳基氧基、(C1-C60)烷基氧基、(C1-C60)芳基硫基、(C6-C60)烷基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基及羥基。
化學式(2)至(4)之一者表示之摻雜劑化合物可由含有下列結構之一之化合物具體例示，但不限於此。
電致發光層意指在該層發生電致發光作用，且其可為單層或多層，該多層係由兩層或更多層積疊(laminate)而成。當依本發明之組成使用主體-摻雜劑之混合物時，因所發明之電致發光主體，可證實顯著改善的發光效率。此可藉由0.5至10重量%之摻雜濃度而達成。與其他傳統主體材料相比，本發明之主體呈現較高的電洞及電子傳導率，及優異的材料安定性，並提供改善的裝置壽命以及發光效率。
本發明之有機電致發光裝置可復包括一種或多種選自芳基胺化合物及苯乙烯基芳基胺化合物之化合物，以及化學式(1)表示之有機電致發光化合物。芳基胺或苯乙烯基芳基胺化合物之實例包含，但不限於化學式(5)表示之化合物：
其中，Ar31
及Ar32
獨立地表示(C1-C60)烷基、(C6-C60)芳基、(C4-C60)雜芳基、(C6-C60)芳基胺基、(C1-C60)烷基胺基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、或(C3-C60)環烷基，或Ar31
及Ar32
可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基相鍵聯，以形成脂環、或單環或多環之芳香環；
當e為1，Ar33
表示(C6-C60)芳基、(C4-C60)雜芳基、或選自下列結構之取代基：
當e為2，Ar33
表示(C6-C60)伸芳基、(C4-C60)雜伸芳基、或選自下列結構之取代基：
其中，Ar34
及Ar35
獨立地表示(C6-C60)伸芳基或(C4-C60)雜伸芳基；
R321
、R322
及R323
獨立地表示氫、(C1-C60)烷基或(C6-C60)芳基；
f為1至4之整數；g為整數0或1；及
Ar31
及Ar32
之烷基、芳基、雜芳基、芳基胺基、烷基胺基、環烷基或雜環烷基；或Ar33
之芳基、雜芳基、伸芳基或雜伸芳基；或Ar34
及Ar35
之伸芳基或雜伸芳基；或R321
至R323
之烷基或芳基可進一步經一個或多個選自下列所組成群組之取代基取代：氘、鹵素、(C1-C60)烷基、(C6-C60)芳基、(C4-C60)雜芳基、含有一個或多個選自N、O及S之雜原子之5員或6員雜環烷基、(C3-C60)環烷基、三(C1-C60)烷基矽烷基、二(C1-C60)烷基(C6-C60)芳基矽烷基、三(C6-C60)芳基矽烷基、金剛烷基、(C7-C60)雙環烷基、(C2-C60)烯基、(C2-C60)炔基、氰基、(C1-C60)烷基胺基、(C6-C60)芳基胺基、(C6-C60)芳基(C1-C60)烷基、(C6-C60)芳基氧基、(C1-C60)烷基氧基、(C6-C60)芳基硫基、(C1-C60)烷基硫基、(C1-C60)烷氧基羰基、(C1-C60)烷基羰基、(C6-C60)芳基羰基、羧基、硝基及羥基。
芳基胺化合物及苯乙烯基芳基胺化合物可由下列化合物具體例示，但不限於此。
本發明之有機電致發光裝置中，該有機層除了包括化學式(1)表示之有機電致發光化合物之外，可復包括一種或多種選自下列所組成之群組之金屬：第1族之有機金屬、第2族之有機金屬、第4週期及第5週期之過渡金屬、鑭系金屬及d-過渡元素。除電致發光層外，該有機層可復包括電荷生成層。
本發明可實現具有獨立發光模式之像素結構的電致發光裝置，係同時經平行圖案化，該電致發光裝置包括含有化學式(1)之化合物作為次像素、及包括一種或多種選自芳基胺化合物及苯乙烯基芳基胺化合物所組成群組之化合物之一種或多種次像素之電致發光裝置。
再者，本發明之有機電致發光裝置係有機顯示器，復包括在有機層中具有電致發光峰(electroluminescent peak)波長不少於560nm之化合物。具有EL峰波長不少於560hm之化合物可由化學式(6)至(10)之一者表示之化合物例示之，但不限於此。
化學式(6)
M1
L101
L102
L103
化學式(6)中，M1
係選自元素周期表第7族、第8族、第9族、第10族、第11族、第13族、第14族、第15族及第16族之金屬，而配位子(ligand)L101
、L102
及L103
係獨立地選自下列結構：
其中，R401
至R403
獨立地表示氫、氘、含有或不含有鹵素取代基之(C1-C60)烷基、含有或不含有(C1-C60)烷基取代基之(C6-C60)芳基、或鹵素；
R404
至R419
獨立地表示氫、氘、(C1-C60)烷基、(C1-C30)烷氧基、(C3-C60)環烷基、(C2-C30)烯基、(C6-C60)芳基、單或二(C1-C30)烷基胺基、單或二(C6-C30)芳基胺基、SF5
、三(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、三(C6-C30)芳基矽烷基、氰基或鹵素，且該R404
至R419
之烷基、環烷基、烯基或芳基可進一步經選自氘、(C1-C60)烷基、(C6-C60)芳基及鹵素之一個或多個取代基取代；
R420
至R423
獨立地表示氫、氘、含有或不含有鹵素取代基之(C1-C60)烷基、含有或不含有(C1-C60)烷基取代基之(C6-C60)芳基；
R424
及R425
獨立地表示氫、氘、(C1-C60)烷基、(C6-C60)芳基或鹵素，或R424
及R425
可藉由含有或不含有稠合環之(C3-C12)伸烷基或(C3-C12)伸烯基相鍵聯，以形成脂環、或單環或多環之芳香環；R424
及R425
之烷基或芳基，或R424
及R425
藉由含有或不含有稠合環之(C3-C12)伸烷基或(C3-C12)伸烯基相鍵聯所形成之脂環、或單環或多環之芳香環可進一步經選自下列之一個或多個取代基取代：氘、含有或不含有鹵素取代基之(C1-C60)烷基、(C1-C30)烷氧基、鹵素、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基及(C6-C60)芳基；
R426
表示(C1-C60)烷基、(C6-C60)芳基、或(C5-C60)雜芳基或鹵素；
R427
至R429
獨立地表示氫、氘、(C1-C60)烷基、(C6-C60)芳基或鹵素，且R426
至R429
之烷基或芳基可進一步經鹵素或(C1-C60)烷基取代；Q表示或，及R431
至R442
獨立地表示氫、氘、含有或不含有鹵素取代基之(C1-C60)烷基、(C1-C30)烷氧基、鹵素、(C6-C60)芳基、氰基或(C5-C60)環烷基，或各R431
至R442
可藉由伸烷基或伸烯基與相鄰取代基鍵聯，以形成(C5-C7)螺環或(C5-C9)稠合環，或其個別可藉由伸烷基或伸烯基與R407
或R408
相鍵聯以形成(C5-C7)稠合環。
化學式(7)中，R501
至R504
獨立地表示(C1-C60)烷基或(C6-C60)芳基，或其個別可藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯，以形成脂環、或單環或多環之芳香環；且R501
至R504
之烷基或芳基，或R501
至R504
藉由含有或不含有稠合環之(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯所形成之脂環、或單環或多環之芳香環可進一步經選自下列之一個或多個取代基所取代：氘、含有或不含有鹵素取代基之(C1-C60)烷基、(C1-C60)烷氧基、鹵素、三(C1-C60)烷基矽烷基、三(C6-C60)芳基矽烷基及(C6-C60)芳基。
化學式(10)
L201
L202
M2
(T)h
化學式(10)中，配位子L201
及L202
獨立地選自下列結構：
M2
為二價或三價金屬；
當M2
為二價金屬時，h為0，當M2
為三價金屬時，h為1；
T表示(C6-C60)芳基氧基或三(C6-C60)芳基矽烷基，且該T之芳基氧基或三芳基矽烷基可進一步經(C1-C60)烷基或(C6-C60)芳基取代；
K表示O、S或Se；
環I表示唑、噻唑、咪唑、二唑、噻二唑、苯并唑、苯并噻唑、苯并咪唑、吡啶或喹啉；
環J表示吡啶或喹啉，且環J可進一步經(C1-C60)烷基、或含有或不含有(C1-C60)烷基取代基之苯基或含有或不含有(C1-C60)烷基取代基萘基取代；
R501
至R504
獨立地表示氫、氘、(C1-C60)烷基、鹵素、三(C1-C60)烷基矽烷基、三(C6-C60)芳基矽烷基或(C6-C60)芳基，或R501
至R504
可個別藉由(C3-C60)伸烷基或(C3-C60)伸烯基與相鄰取代基鍵聯以形成稠合環，且吡啶或喹啉可與R501
形成化學鍵以形成稠合環；
環I或R501
至R504
之芳基可進一步經氘、(C1-C60)烷基、鹵素、含有鹵素取代基之(C1-C60)烷基、苯基、萘基、三(C1-C60)烷基矽烷基、三(C6-C60)芳基矽烷基或胺基取代。
電致發光峰波長不少於560nm之化合物可經由下列化合物例示，但不限於此。
於本發明之有機電致發光裝置中，較佳係將一層或多層(後文中稱為“表面層”)選自硫屬元素化合物層(chalcogenide layer)、金屬鹵化物層與金屬氧化物層之層體設置於該電極對之至少一側的內表面上。具體而言，較佳係將矽及鋁金屬(包含氧化物)之硫屬元素化合物層設置於EL介質層(medium layer)之陽極表面上，及將鹵化金屬層或金屬氧化物層設置於EL介質層之陰極表面上。藉此，可獲得操作安定性。
硫屬元素化合物之實例較佳包含SiOx
(1≦X≦2)、AlOx
(1≦X≦1.5)、SiON、SiAlON等。金屬鹵化物之實例較佳包含LiF、MgF2
、CaF2
、鑭系金屬之氟化物等。金屬氧化物之實例較佳包含CS2
O、Li2
O、MgO、SrO、BaO、CaO等。
於本發明之有機電致發光裝置中，亦較佳者為將電子傳輸化合物及還原性摻雜劑之混合區域、或電洞傳輸化合物及氧化性摻雜劑之混合區域設置於前述所製造之電極對之至少一個表面上。藉此，電子傳輸化合物被還原成陰離子，因而促使電子從混合區域注入及傳輸至EL介質。此外，由於電洞傳輸化合物被氧化而形成陽離子，因此促使電洞從混合區域注入及傳導至EL介質。較佳的氧化性摻雜劑包含各種路易士酸(Lewis acid)及接受者化合物(acceptor compound)。較佳的還原性摻雜劑包含鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。
本發明之有機電致發光化合物作為材料呈現高發光效率及優異色純度和壽命性質，因此可自其製得具有極佳操作壽命之OLED。
參照本發明之代表化合物，進一步說明本發明之化合物，製造該化合物之方法，及自其所製造之裝置的電致發光性質，該代表化合物僅提供為例示說明用，並非意欲以任何形式限制本發明之範圍。
製備化合物(A)
在氮氣氛圍下，於四氫呋喃(THF)(670毫升(mL))中加入2-溴苯甲醛(25.0公克(g)，140毫莫耳(mmol))、苯乙炔(17.8毫升，162毫莫耳)、二氯雙(三苯基膦)鈀(II)[PdCl2
(PPh3
)2
](2.8克，4毫莫耳)及碘化亞銅[CuI](1.3克，7毫莫耳)及三乙胺(38毫升，270毫莫耳)，且混合物在80℃回流攪拌3小時。反應混合物以蒸餾水及乙酸乙酯洗滌，及藉由管柱層析純化，獲得化合物(A)(16.0克，78毫莫耳)。
製備化合物(B)
在氮氣氛圍下，將苯乙炔(32.3毫升，294毫莫耳)、NBS(N-溴琥珀醯亞胺)(58克，323毫莫耳)及硝酸銀[AgNO3
](5.0克，30毫莫耳)加入丙酮中，將混合物在0℃攪拌。當反應完成時，加入正己烷，及過濾混合物。所得之固體以正己烷洗滌四次，獲得化合物(B)(16.0克，93毫莫耳)。
製備化合物(C)
將化合物(A)(16.0克，78毫莫耳)、三氟甲磺酸銅(II)[Cu(OSO2
CF3
)2
](1.6克，化合物A的1/10)及1,2-二氯乙烷(160毫升)填裝到燒瓶內，及將該混合物維持在氮氣氛圍下。維持氮氣氛圍同時將化合物(B)(16.0克，93毫莫耳)、二氟乙酸(5毫升)及1,2-二氯乙烷(160毫升)加到另一燒瓶內。合併兩燒瓶之內容物，且將所得混合物在100℃回流攪拌30分鐘。所得化合物以蒸餾水洗滌，且經管柱層析純化，獲得化合物(C)(7.3克，26毫莫耳)。
製備化合物(D)
將化合物(C)(7.3克，26毫莫耳)溶解於THF(130毫升)中，並加入正丁基鋰(13.5毫升，33.8毫莫耳，2.5M溶於己烷中)，且混合物在-78℃攪拌1小時。1小時後，加入2-異丙氧基-4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷(7.9毫升)(39毫莫耳)，且所得混合物在室溫攪拌12小時。當反應完成時，反應混合物以蒸餾水及乙酸乙酯洗滌。經管柱層析純化以得化合物(D)(4.8克，14毫莫耳)。
製備化合物(E)
將菲(10克，0.056毫莫耳)、溴(7.4毫升，0.15莫耳)及CCl4
(280毫升)填裝到反應瓶內，並將混合物在100℃或更高之溫度下回流攪拌4小時。當反應完成時，加入硫代硫酸鈉(Na2
S2
O3
)水溶液，且將所得混合物攪拌1小時。混合物以乙酸乙酯萃取，且萃取物以蒸餾水洗滌3次。所得有機層使用旋轉蒸發器蒸發，及經管柱層析純化，獲得化合物(E)(9克，48%)。
製備化合物(F)
反應瓶中，將化合物(E)(8.3克，0.025莫耳)及2-萘硼酸(6.4克，0.037莫耳)及肆(三苯基膦)鈀(0)(Pd[P(C6
H5
)3
]4
)(0.9克，0.001莫耳)保持在氮氣氛圍下。然後，加入2M之Na2
CO3
溶液(50毫升)、甲苯(130毫升)及乙醇(65毫升)，且混合物在80℃回流攪拌12小時。當反應完成時，反應混合物以乙酸乙酯萃取，且萃取物以蒸餾水洗滌3次。所得有機層使用旋轉蒸發器蒸發，及經管柱層析純化，獲得化合物(F)(8克，83.5%)。
製備化合物(G)
在氮氣氛圍下，將2-溴菲(6.3克，0.021莫耳)加入溴(1.6毫升，0.31莫耳)及CCl4
(103毫升)中，且混合物在100℃或更高之溫度回流攪拌4小時。當反應完成時，加入硫代硫酸鈉(Na2
S2
O3
)水溶液，及攪拌混合物1小時。所得混合物以乙酸乙酯萃取，且萃取物以蒸餾水洗滌3次。所得有機層使用旋轉蒸發器蒸發，及經管柱層析純化，獲得化合物(G)(5克，62%)。
製備化合物(2)
將化合物(G)(4.6克，12毫莫耳)、化合物(D)(4.8克，14毫莫耳)、2M碳酸鉀溶液(18毫升)及肆(三苯基膦)鈀[Pd(PPh3
)4
](0.7克，0.6毫莫耳)加入甲苯(100毫升)中。加入Aliquat 336(0.1毫升)，且混合物在80℃回流攪拌12小時。所得化合物以蒸餾水及乙酸乙酯洗滌，及藉由管柱層析純化，獲得標的化合物(化合物2)(3.2克，5.5毫莫耳)。
[製備例2]製備化合物(360)
製備化合物(H)
在0℃將三氟甲磺酸(29.5毫升，0.33莫耳)緩慢加入9,10-菲醌(7克，0.0336莫耳)。維持溫度為0℃，緩慢加入NBS(13.2克，0.0742莫耳)。然後將反應混合物回溫至環境溫度，並攪拌6小時。接著將混合物緩慢地注入冰水中，及在減壓下過濾。以水及甲醇洗滌而獲得化合物(H)(10克，81%)。
製備化合物(I)
將2-溴菲(16.9克，0.0819莫耳)溶解於THF中，並使溶液冷卻至-78℃。於該溶液中，緩慢加入n-BuLi(溶於己烷中，2.5M)(28毫升)。30分鐘後，將混合物回溫至環境溫度，並再攪拌30分鐘。立即加入化合物(H)(10克，0.0273莫耳)，且混合物在環境溫度攪拌12小時。以乙酸乙酯/蒸餾水萃取後，萃取物以硫酸鎂(MgSO4
)乾燥及在減壓下過濾。經管柱層析純化以得化合物(I)(8克，47%)之固體。
製備化合物(1)
將化合物(I)(8克，0.0129莫耳)及乙酸(100毫升)在回流下加熱。緩慢加入鋅(12.3克，0.194莫耳)及HCl(35%，50毫升)。30分鐘後，再加入相同量之Zn及HCl。在回流下加熱12小時後，過濾生成之固體，及加入Na2
CO3
(水溶液)以中和。經管柱層析純化以得化合物(J)(5克，65.8%)之固體。
製備化合物(K)
將化合物(J)(5克，8.5毫莫耳)、1-萘硼酸(1.5克，8.7毫莫耳)、PdCl2
(PPh3
)2
(0.3克，0.427毫莫耳)、2M之K2
CO3
溶液(12.5毫升)、甲苯(40毫升)及乙醇(20毫升)在80℃回流下加熱3小時。當反應完成時，反應混合物以乙酸乙酯/蒸餾水萃取，並經吸收管柱純化，獲得化合物(K)(3克，55.5%)之固體。
製備化合物(360)
將化合物(K)(3克，4.72毫莫耳)、化合物(D)(2.3克，9.27毫莫耳)、Pd(PPh3
)4
(0.5克，0.43毫莫耳)、2M之K2
CO3
(水溶液10毫升)、Aliquat 336(0.05毫升)、甲苯(30毫升)及乙醇(15毫升)在90℃回流下加熱6小時。當反應完成時，反應混合物以乙酸乙酯/蒸餾水萃取，且將萃取物經吸收管柱純化，獲得標的化合物(化合物360)(1.8克，50.2%)之固體。
[製備例3]製備化合物(794)
在氮氣下，將9，10-二溴蒽(4.6克，12毫莫耳)、化合物(D)(4.8克，14毫莫耳)、2M碳酸鉀溶液(18毫升)及肆(三苯基膦)鈀[Pd(PPh3
)4
](0.7克，0.6毫莫耳)加入甲苯(100毫升)中，並加入Aliquat 336(0.1毫升)。所得混合物在80℃回流攪拌12小時。所得化合物以蒸餾水及乙酸乙酯洗滌，及經管柱層析純化，獲得化合物(794)(3.2克，5.5毫莫耳)。
根據製備例1至3相同程序，製備有機電致發光化合物(化合物1至939)，其之1
H NMR與MS/FAB數據列於表1。
[實施例1]製造OLED(1)
使用本發明之有機電致發光化合物製造OLED裝置。
首先，使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水清洗由OLED用之玻璃(Samsung Corning製造)(1)所製得的透明電極(2)ITO薄膜(15Ω/□)，且儲存在異丙酮中備用。
接著，將ITO基板裝配於真空氣相沉積裝置之基板夾中，並將4,4’,4”-參(N,N-(2-萘基)-苯基胺基)三苯胺(2-TNATA)置於該真空氣相沉積裝置之小室(cell)中，然後在腔室中通氣以達10-6
托(torr)真空。對該小室施加電流以揮發2-TNATA，從而在ITO基板上氣相沈積厚度為60奈米(nm)的電洞注入層(3)。
然後，將N,N’一雙(α-萘基)-N,N’-二苯基-4,4’-二胺(NPB)充填至該真空氣相沉積裝置之另一小室中，對該小室施加電流以揮發NPB，從而在該電洞注入層上氣相沉積厚度為20奈米的電洞傳輸層(4)。
在形成電洞注入層及電洞傳輸層後，如下述氣相沉積電致發光層於其上。
將本發明之化合物(例如化合物2)作為電致發光材料充填至真空氣相沉積裝置之一小室中，及將DSA-Ph(其結構如下所示)充填至另一小室中。同時加熱該兩小室，從而以DSA-Ph為2至5重量%之氣相沉積速率，於該電洞傳輸層上氣相沉積厚度為30奈米之電致發光層(5)。
然後氣相沉積參(8-羥基喹啉)鋁(III)(Alq)以形成厚度為20奈米之電子傳輸層(6)。之後，氣相沉積8-羥基喹啉鋰(lithium quinolate)(Liq)以形成厚度為1至2奈米之電子注入層(7)。使用另一真空氣相沉積裝置，在其上氣相沉積厚度為150奈米之鋁(Al)陰極(8)而製造OLED。
在用作OLED之電致發光材料前，各材料係經10-6
托真空昇華以純化。
[實施例2]使用本發明之化合物製造OLED
使用與實施例1相同程序形成電洞注入層及電洞傳輸層後，將本發明之化合物(例如化合物705)充填至上述真空氣相沉積裝置之一小室中，同時將化合物(E)(其結構如下所示)充填至另一小室中。在不同速率下揮發兩種材料而完成摻雜(以主體材料為基準計，摻雜濃度為2至5重量%)，從而在電洞傳輸層上氣相沉積厚度為30奈米之電致發光層。
接著，以實施例1相同程序來氣相沉積電子傳輸層(6)及電子注入層(7)，再使用另一真空氣相沉積裝置來氣相沉積厚度為150奈米之鋁(Al)陰極(8)以製造OLED。
[實施例3]使用本發明之化合物製造OLED
使用與實施例1相同程序形成電洞注入層及電洞傳輸層後，將本發明之化合物(例如化合物218)充填至上述真空氣相沉積裝置之一小室中，同時將化合物(A)(其結構如下所示)充填至另一小室中。在不同速率下揮發兩種材料而完成摻雜(以主體材料為基準計，摻雜濃度為2至5重量%)，從而在電洞傳輸層上氣相沉積厚度為30奈米之電致發光層。
然後，以實施例1相同程序來氣相沉積電子傳輸層(6)及電子注入層(7)，再使用另一真空氣相沉積裝置來氣相沉積厚度為150奈米之鋁(Al)陰極(8)以製造OLEDo
[比較例1]使用傳統電致發光材料製造OLED
使用與實施例1相同程序形成電洞注入層(3)及電洞傳輸層(4)後，將二萘基蒽(DNA)充填至上述真空氣相沉積裝置之一小室中作為電致發光材料，及將DSA-Ph充填至另一小室中，如實施例1。然後以100：3之氣相沉積速率，於電洞傳輸層上氣相沉積厚度為30奈米之電致發光層(5)。
然後，以實施例1相同程序來氣相沉積電子傳輸層(6)及電子注入層(7)，再使用另一真空氣相沉積裝置來氣相沉積厚度為150奈米之鋁(Al)陰極(8)以製造OLED。
[比較例2]使用傳統電致發光材料製造OLED
使用與實施例2相同程序形成電洞注入層及電洞傳輸層後，將Alq充填至上述真空氣相沉積裝置之一小室中作為電致發光主體材料，同時將香豆素545T(C545T)充填至另一小室中。在不同速率下揮發兩種材料以完成摻雜，從而在電洞傳輸層上氣相沉積厚度為30奈米之電致發光層。以Alq為基準計，摻雜濃度較佳為1至3重量%。
然後，以實施例1相同程序來氣相沉積電子傳輸層及電子注入層，再使用另一真空氣相沉積裝置來氣相沉積厚度為150奈米之鋁(Al)陰極以製造OLED。
在5,000燭光/平方米(cd/m2
)下測量從包括本發明之有機電致發光化合物之實施例1至3所製得之OLED的發光效率，以及從包括傳統電致發光化合物之比較例1及2所製得之OLED的發光效率，結果示於表2。
從表2可知，與比較例1所用之DNA之傳統EL材料相較，當本發明之電致發光材料(經相同類型之DSA-Ph摻雜)應用在藍光電致發光裝置時，色純度明顯增加，同時維持至少相當的發光效率。
與傳統化合物Alq：C545T(比較例2)相較，當本發明之電致發光材料(經化合物(E)或化合物(A)以3.0%之摻雜濃度摻雜)應用在綠光電致發光裝置時，發光效率明顯改善，同時維持至少相當的色純度。
如上述，本發明之有機電致發光化合物可用作高效率之藍光或綠光電致發光材料，且施用本發明之主體材料之電致發光裝置，因而在色純度方面呈現顯著的改善。色純度及發光效率皆改善的結果，證實本發明之材料之優異的特徵。
1．．．玻璃
2．．．透明電極
3．．．電洞注入層
4．．．電洞傳輸層
5．．．電致發光層
6．．．電子傳輸層
7．．．電子注入層
8．．．鋁(Al)陰極
第1圖係為OLED之剖面圖。
1．．．玻璃
2．．．透明電極
3．．．電洞注入層
4．．．電洞傳輸層
5．．．電致發光層
6．．．電子傳輸層
7．．．電子注入層
8．．．鋁陰極
Claims (13)
- 一種以化學式(1)表示之有機電致發光化合物：
- 如申請專利範圍第1項之有機電致發光化合物，其中，L1 係選自下列結構：
- 如申請專利範圍第2項之有機電致發光化合物，其中，L1 係選自下列結構：
- 如申請專利範圍第1項之有機電致發光化合物，其中，-L2 -L3 -Ar1 係選自下列結構：
- 如申請專利範圍第1項之有機電致發光化合物，其中，-L2 -L3 -Ar1 係選自下列結構：
- 如申請專利範圍第1項之有機電致發光化合物，其中，R1 至R11 獨立地表示氫、氘、氟、氯、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、苯甲基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第三丁氧基、正戊氧基、異戊氧基、正己氧基、正庚氧基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、N-嗎啉基、硫代N-嗎啉基、嗎啉基、硫代嗎啉基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、二甲基苯基矽烷基、三苯基矽烷基、雙環[2.2.1]庚基、雙環[2.2.2]辛基、雙環[5.2.0]壬基、雙環[4.2.2]癸基4-戊基雙環[2.2.2]辛基、乙烯基、苯基乙烯基、乙炔基、苯基乙炔基、氰基、甲基硫基、苯基氧基、苯基硫基、甲氧基羰基、乙氧基羰基、第三丁氧基羰基、甲基羰基、乙基羰基、苯甲基羰基、苯基羰基、羧基、硝基或羥基。
- 一種有機發光二極體，包括以化學式(1)表示之有機電致發光化合物：化學式(1)
- 如申請專利範圍第7項之有機發光二極體，其中，該有 機層包括一種或多種選自芳基胺化合物及苯乙烯基芳基胺化合物所組成之群組之化合物。
- 如申請專利範圍第7項之有機發光二極體，其中，該有機層包括一種或多種選自第1族有機金屬、第2族有機金屬、第4週期及第5週期過渡金屬、鑭系金屬及d-過渡元素所組成之群組之金屬。
- 如申請專利範圍第7項之有機發光二極體，其係有機顯示器，同時包括該有機電致發光化合物及電致發光峰波長不少於560 nm之化合物。
- 如申請專利範圍第7項之有機發光二極體，其中，該有機層包括電致發光層及電荷生成層兩者。
- 如申請專利範圍第7項之有機發光二極體，其中，於該電極對之一個或兩個電極之內表面上係設置還原性摻雜劑及有機物質之混合區域、或氧化性摻雜劑及有機物質之混合區域。
- 一種有機太陽能電池，包括以化學式(1)表示之有機電致發光化合物：
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- 2008-10-29 KR KR1020080106223A patent/KR100901887B1/ko not_active Expired - Fee Related
- 2008-12-30 EP EP08173052A patent/EP2100941A3/en not_active Withdrawn
- 2008-12-30 TW TW097151335A patent/TWI385236B/zh not_active IP Right Cessation
- 2008-12-31 US US12/317,986 patent/US20090230852A1/en not_active Abandoned
- 2008-12-31 CN CN200810107500A patent/CN101531565A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101531565A (zh) | 2009-09-16 |
| JP5645365B2 (ja) | 2014-12-24 |
| US20090230852A1 (en) | 2009-09-17 |
| EP2100941A3 (en) | 2010-10-06 |
| KR100901887B1 (ko) | 2009-06-09 |
| TW200938610A (en) | 2009-09-16 |
| JP2009283899A (ja) | 2009-12-03 |
| EP2100941A2 (en) | 2009-09-16 |
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