TW201307329A - 用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置 - Google Patents
用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置 Download PDFInfo
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- TW201307329A TW201307329A TW101119280A TW101119280A TW201307329A TW 201307329 A TW201307329 A TW 201307329A TW 101119280 A TW101119280 A TW 101119280A TW 101119280 A TW101119280 A TW 101119280A TW 201307329 A TW201307329 A TW 201307329A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- 239000012776 electronic material Substances 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 230000005684 electric field Effects 0.000 claims description 23
- -1 Cyano, carbazolyl Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052789 astatine Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001336 alkenes Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 description 35
- 239000010410 layer Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000003943 azolyl group Chemical group 0.000 description 3
- 238000004299 exfoliation Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 150000001786 chalcogen compounds Chemical class 0.000 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
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- 150000003624 transition metals Chemical class 0.000 description 2
- 125000001425 triazolyl group Chemical group 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
- 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
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000006017 1-propenyl group Chemical group 0.000 description 1
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- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 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
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- 235000019270 ammonium chloride Nutrition 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
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- 229910052746 lanthanum Inorganic materials 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical class [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 230000008719 thickening Effects 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
本發明係關於新穎化合物及含有該化合物之有機電場發光裝置。本發明之化合物可製造具有高發光效率與長操作壽命之有機電場發光裝置。
Description
本發明係關於用於有機電子材料之新穎化合物及使用該化合物之有機電場發光裝置。
電場發光(EL)裝置為自發光裝置,相較其他類型顯示裝置其具有優點在於提供較寬之視角、較高之對比度及具有較快之響應時間。伊斯門-柯達(Eastman Kodak)首先研發了一種有機EL裝置,其藉由使用小分子例如芳香族二胺及鋁之錯合物作為形成發光層之材料。[Appl.Phys.Lett.51,913,1987]
決定有機EL裝置的發光效率的最重要因素係發光材料。到目前為止,螢光材料被廣泛地使用作為發光材料。然而,鑑於電場發光機制,磷光材料理論上比螢光材料呈現高出四倍的發光效率。銥(III)化合物已被廣泛使用作為磷光材料,包含分別作為紅光材料、綠光材料及藍光材料之二(2-(2’-苯并噻吩基)-吡啶-N,C3’)銥(乙醯丙酮)[(acac)Ir(btp)2]、三(2-苯基吡啶)銥[Ir(ppy)3]及二(4,6-二氟苯基吡啶-N,C2’)吡啶甲基銥(Firpic)。特別地,最近日本、歐洲與美國致力於研發許多螢光材料。
目前4,4’-N,N’-二咔唑-聯苯(CBP)是最被廣泛應用作為主體材料之磷光物質。進一步的使用浴銅靈(bathocuproine(BCP))與鋁(III)二(2-甲基-8-喹啉)(4-苯基酚)(BAlq)作為具有高效率之有機EL裝置之電洞阻隔
層。以及Pioneer(日本)等已開發採用Balq衍生物作為主體材料之高性能有機EL裝置。
雖然這些磷光主體材料提供好的發光特性,但有下述缺點:
1.由於它的玻璃轉換溫度低與熱穩定性差,在真空高溫沉積過程中可能發生降解。
2.有機電場發光裝置的功率效率可由[(π/電壓)×電流效率]而得,且功率效率與電壓成反比,因此,功率效率應為高的以減少功率消耗。雖然包含磷光材料的有機EL裝置相較於包含螢光材料者提供較高的電流效率(cd/A),當使用傳統材料,例如BAlq與CBP作為磷光主體材料時,相較於使用螢光材料之有機EL裝置必須有明顯的高驅動電壓。因此就功率效率(流明/瓦(lm/W))而言沒有優點。
3.進一步地,有機電場發光裝置的操作壽命短且發光效率仍待改進。
國際專利公開WO 2006/049013號揭露具有縮合雙環基團為主鏈結構之用於有機電場發光材料的化合物。然而,其並未揭露具有含氮縮合雙環基團之苯并咔唑(benzocarbazole)化合物,該化合物於苯并咔唑的9-位經以芳族環稠合之雜環烷基或環烷基取代。
本發明之目的係提供用於有機電子材料之化合物,其
可賦予裝置高發光效率與長操作壽命,並擁有適當色座標;以及提供使用該化合物於有機電子材料之有機電場發光裝置,其擁有高效率與長操作壽命。
本發明者發現上述目的可由下述式1表示之化合物達成:
其中,L1與L2係各獨立表示單鍵、經取代或未經取代之3-至30員伸雜芳基、經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C6-C30)伸環烷基;X1係表示CH或N;Y1係表示-O-、-S-、-CR6R7-或-NR8-;R1至R5各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3-至30員的雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之5-至7員雜環烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、硝基或羥基;或R4和R5各獨立連結至一個或多個鄰近取代基以形成環中
之碳原子可經選自氮、氧與硫之至少一雜原子置換之單環或多環之(C5-C30)脂環族環或芳族環;R6至R8和R11至R17各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3-至30員雜芳基、經取代或未經取代之5-至7員雜環烷基、或經取代或未經取代之(C3-C30)環烷基;或R6至R8和R11至R17各獨立連結至一個或多個鄰近取代基以形成環中碳原子可經選自氮、氧與硫之至少一雜原子置換之單環或多環之(C5-C30)脂環族環或芳族環;a係表示整數1至6;當a係整數2或更多時,每個R1係相同或不同;b、c和e係獨立表示整數1至4;當b,c和e係整數2或更多時,每個R2、R3或R5係相同或不同;d係表示整數1至3;d係整數2或更多時,每個R4係相同或不同;以及該雜環烷基和該(伸)雜芳基含有選自B、N、O、S、P(=O)、Si及P之至少一個雜原子。
根據本發明之用於有機電子材料之化合物可製造具有高發光效率和長操作壽命之有機電場發光裝置。
本發明詳述如下。然而,以下描述意圖解釋本發明,不以任何方式限制本發明範圍。
本發明係有關一種用於有機電子材料之如上式1表示之化合物,以及含有該化合物之有機電場發光裝置。
本文中,「(C1-C30)(伸)烷基」係表示具有1至30個碳原子之直鏈或分支鏈(伸)烷基,其碳原子數較佳係1至20,更佳係1至10,並包含甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等;「(C2-C30)(伸)烯基」係表示具有2至30個碳原子之直鏈或分支鏈(伸)烯基,其碳原子數較佳係2至20,更佳係2至10,並包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;「(C2-C30)炔基」係表示具有2至30個碳原子之直鏈或分支鏈炔基,其碳原子數較佳係2至20,更佳係2至10,並包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等;「(C1-C30)烷氧基」係表示具有1至30個碳原子之直鏈或分支鏈烷氧基,其碳原子數較佳係1至20,更佳係1至10,並包含甲氧基、乙氧基、丙氧基、異丙氧基、1-乙基丙氧基等;「(C3-C30)環烷基」係表示具有3至30個碳原子之單環或多環烴,其碳原子數較佳係3至20,更佳係3至7,並包含環丙基、環丁基、環戊基、環己基等;「(C6-C30)伸環烷基」係由具有6至30,較佳係6至20,更佳係6至12個碳原子之環烷基移除氫者;「5-至7員雜環烷基」係表示具有選自B、N、O、S、P(=O)、Si和P之至少一個雜原子,較佳係N、O和S,和5至7個環主鏈原子的環烷基,係包含四氫呋喃、吡咯啶、硫雜環戊烷、四氫吡喃等;
「(C6-C30)(伸)芳基」係衍生自具有6至30個碳原子之芳族烴之單環或稠合環,其碳原子數較佳係6至20,更佳係6至12,並包含苯基、聯苯基、聯三苯基(terphenyl)、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基(triphenylenyl)、芘基、并四苯基、苝基、蒯基(chrysenyl)、稠四苯基、丙二烯合茀基(fluoranthenyl)等;「3-至30員(伸)雜芳基」係包含選自B、N、O、S、P(=O)、Si和P之至少1個,較佳係1至4個雜原子,和3至30個環主鏈原子的芳基;係與至少一個苯環縮合的單環或稠合環,較佳係5至21個,更佳係5至12個環主鏈原子;可部分飽和;可為以單鍵連結至少一個雜芳基或芳基至雜芳基所形成者;並包含單環型式雜芳基,包含呋喃基、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、吡啶基、吡基、嘧啶基、嗒基等;與稠合環型式雜芳基,包含苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、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、啡基、啡啶基、苯并二呃基(benzoctioxolyl)等。此外,「鹵素」包含F、Cl、Br和I。
L1、L2、R1至R5、R6至R8和R11至R17之經取代之(伸)烷基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)
環烷基、經取代之雜環烷基、經取代之芳烷基與經取代之伸烯基中之取代基各獨立地為選自下述所成組群之至少一者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基經取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、3員至7員雜環烷基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基。
在上述式1中,L1和L2係各獨立表示單鍵、3-至30員伸雜芳基、(C6-C30)伸芳基或(C6-C30)伸環烷基;X1係表示CH或N;Y1係表示-O-、-S-、-CR6R7-或-NR8-;R1至R5係各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3-至30員雜芳基、N-咔唑基、-NR11R12或-SiR13R14R15;或R4和R5係各獨立連結至一個或多個鄰近取代基以形成環之碳原子可被選自氮、氧和硫之至少一個雜原子置換之單環或多環之(C5-C30)脂環族環或芳族環;R6至R8係各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基或3-至30員雜芳基;R11至R15係各獨立表示(C1-C30)烷基、(C6-C30)芳基或3-至30員雜芳基;L1和L2的伸芳基、雜伸芳基和伸環烷基,與R1至R5和R11至R15的烷基、芳基和
雜芳基,各獨立經選自下列所成組群之至少一者經取代或為未經取代者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、經(C6-C30)芳基經取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基及(C6-C30)芳基(C1-C30)烷基。
L1和L2各獨立較佳係單鍵、經取代或未經取代之(C6-C15)伸芳基、經取代或未經取代之(C6-C12)伸環烷基,而該經取代之伸芳基的取代基較佳係為(C1-C6)烷基。L1和L2各獨立較佳係單鍵、伸苯基、伸萘基、伸聯苯基(biphenylene)、伸聯三苯基(terphenylene)、伸蒽基、伸茚基、伸茀基、伸菲基、伸聯伸三苯基(triphenylenylene)、伸芘基、伸芘基、伸蒯基、伸稠四苯基(naphthacenylene)、伸丙二烯合茀基、伸環丙基、伸環丁基、伸環戊基、伸環己基、伸環庚基、伸環辛基、伸呋喃基、伸噻吩基、伸吡咯基、伸咪唑基、伸吡唑基、伸噻唑基、伸噻二唑基(thiadiazolylene)、伸異噻唑基、伸唑基、伸異唑基、伸二唑基(oxadiazolylene)、伸三基、伸四基、伸三唑基、伸四唑基、伸呋呫基、伸吡啶基、伸吡基、伸嘧啶基、伸嗒基、伸苯并呋喃基、伸苯并噻吩基、伸異苯并呋喃基、伸苯并咪唑基、伸苯并噻唑基、伸苯并異噻唑基、伸苯并異唑基、伸苯并唑基、伸異吲哚基、伸吲哚基、伸吲唑基、伸苯并噻二唑基(benzothiadiazolylene)、伸喹啉基、伸異喹啉基、伸噌啉基(cinnolinylene)、伸喹唑啉基、伸喹啉基、伸咔唑基、伸啡啶基、伸苯并二
呃基(benzodioxolylene)、伸二苯并呋喃基或伸二苯并噻吩基。
在上述式1中,X1係表示CH或N;Y1係表示-O-、-S-、-CR6R7-或-NR8-。當Y1係-CR6R7-時,R6和R7各獨立較佳係經取代或未經取代(C1-C6)烷基。當Y1係-NR8-時,R8較佳係經取代或未經取代(C6-C20)芳基、或經取代或未經取代之5員至15員雜芳基。經取代之芳基的取代基較佳係選自下列所成組群:氘、鹵素、(C1-C6)烷基和(C6-C12)芳基,而經取代之雜芳基的取代基較佳係(C6-C12)芳基。
在上述式1中,R1至R5較佳各獨立係氫、氘、鹵素、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之5員至15員雜芳基、-NR11R12或-SiR13R14R15;或R4或R5可連結至一個或多個鄰近取代基以形成單環或多環之(C5-C30)脂環族環或芳族環。在R1至R5中,經取代之芳基的取代基較佳係(C1-C6)烷基。R11和R12較佳各獨立係經取代或未經取代之(C6-C12)芳基,R13至R15較佳各獨立係經取代或未經取代之(C1-C6)烷基或經取代或未經取代之(C6-C12)芳基。R4或R5較佳係連結至一個或多個鄰近取代基以形成(C6-C12)芳族環。
在上述式1中,係選自以下結構,但不限
於以下結構:
本發明之代表性化合物包含下述化合物:
關於本發明之用於有機電子材料之化合物可根據以下反應式1製備:
其中R1至R5、Y1、X1、L1、L2、a、b、c、d和e如上述式1般定義,X代表鹵素。
此外,本發明提供包括式1化合物之有機電場發光裝置。該有機電場發光裝置包括第一電極、第二電極以及界於該第一電極與該第二電極之間之至少一層有機層。該有機層包括至少一種本發明之式1化合物。再者,該有機層包括發光層,發光層中包含式1化合物作為主體材料。
此外,與根據本發明之主體材料一起用於有機電場發光裝置的磷光摻雜劑,係可選自下述式2表示之化合物:M 1 L 101 L 102 L 103 ---(2)
其中M1係選自下列所成組群:Ir、Pt、Pd和Os;L101、L102和L103係各獨立選自以下結構:
R201至R203各獨立表示氫、氘、經鹵素取代或未經取代之(C1-C30)烷基、經(C1-C30)烷基經取代或未經取代之(C6-C30)芳基或鹵素;R204至R219各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基、SF5、經取代或未經取代之三(C1-C30)烷基矽基、經取代或未經取代之二-
(C1-C30)烷基(C6-C30)芳基矽基、經取代或未經取代三(C6-C30)芳基矽基、氰基或鹵素;R220至R223各獨立表示氫、氘、經鹵素取代或未經取代之(C1-C30)烷基、或經(C1-30)烷基經取代或未經取代之(C6-C30)芳基;R224和R225係獨立表示氫、氘、經取代或未經取代(C1-C30)烷基、經取代或未經取代(C6-C30)芳基或鹵素;或R224和R225可連結至一個或多個鄰近取代基以形成單環或多環之(C5-C30)脂環族環或芳族環;R226係表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之5-至30員雜芳基或鹵素;R227至R229各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基或鹵素;
Q係表示;
R231至R242各獨立表示氫、氘、經鹵素取代或未經取代之(C1-C30)烷基、(C1-C30)烷氧基、鹵素、經取代或未經取代之(C6-C30)芳基、氰基、經取代或未經取代之(C5-C30)環烷基;或R231至R242各可透過伸烷基或伸烯基連結至鄰近取代基以形成螺環或稠環,或各可透過伸烷基或伸烯基連結至R207或R208而形成飽和或不飽和稠環。
詳細而言,下述式之化合物較佳係使用來作為式2之摻雜化合物:
本發明之有機電場發光裝置,除了包括式1表示之化合物,可進一步包括選自芳香基胺系化合物或苯乙烯基芳香基胺系化合物所成群組之至少一種化合物。
於本發明之有機電場發光裝置中,該有機層可進一步
包括選自下列所成組群之至少一種金屬:週期表之第1族金屬、第2族金屬、第4週期過渡金屬、第5週期過渡金屬、鑭系金屬及d-過渡元素金屬;或至少一種含有該金屬之錯合物。該有機層可包括發光層及電荷產生層。
此外,除了本發明之化合物,該有機電場發光裝置可藉由進一步包括至少一層下述發光層而發射白光,該發光層包括藍色電場發光化合物、紅色電場發光化合物或綠色電場發光化合物。
較佳地,於本發明之有機電場發光裝置中,可將選自硫屬化合物(chalcogenide)層、金屬鹵化物層及金屬氧化物層之至少一層(後文中稱為「表面層」)設置於該一個或兩個電極的一個或多個內表面。更具體而言,較佳係將矽或鋁之硫屬化合物(包括氧化物)層設置於電場發光介質層之陽極表面,並將金屬鹵化物層或金屬氧化物層設置於電場發光介質層之陰極表面。這種表面層可提供有機電場發光裝置之操作安定性。較佳地,該硫屬化合物包含SiOx(1X2)、AlOx(1X1.5)、SiON、SiAlON等;該金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等;及該金屬氧化物包含Cs2O、Li2O、MgO、SrO、BaO、CaO等。
較佳地,根據本發明之有機電場發光裝置中,可將電子傳輸化合物與還原性摻雜劑之混合區域或電洞傳輸化合物與氧化性摻雜劑之混合區域設置於電極對的至少一個表面。於該情況中,電子傳輸化合物被還原成陰離子,且因此自混合區域注入與傳輸電子至電場發光介質變成更容
易。再者,電洞傳輸化合物被氧化成陽離子,且因此自混合區域注入與傳輸電洞至電場發光介質變成更容易。較佳地,氧化性摻雜劑係包括各種路易士酸及接受者(acceptor)化合物;以及還原性摻雜劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。可使用還原性摻雜劑層作為電荷產生層來製備具有兩層或多層電場發光層且發射白光之電場發光裝置。
下文中,本發明之化合物、該化合物之製備方法以及包括該化合物之裝置的發光性質將藉由參考下述實施例詳細地闡述:
將2,4-二氯喹唑啉(30g,151mmol)、9-苯基-9H-咔唑-3-基硼酸(15.6g,75.3mmol)、Pd(PPh3)4(2.6g,2.3mmol)和Na2CO3(16g,150mmol)溶解於甲苯(300mL)與蒸餾水(75mL)之混合物中後,將該反應混合物於90℃攪拌2小時。反應中止後,該反應混合物冷卻至室溫,減壓蒸餾所得有機層後,以MeOH研製。所得固體以二氯甲烷(MC)溶解,再經氧化矽過濾,並以MC和正己烷研製獲得化合物1-1(9.3g,51.4%)。
將7H-苯并[c]咔唑(3.2g,14.7mmol)與化合物1-1(5g,15.8mmol)懸浮至二甲基甲醯胺(DMF)(80mL)後,於室溫將60% NaH(948mg,22mmol)加入至該混合物,並攪拌12小時。加入純水(1 L)後,減壓過濾該混合物。所得固體以MeOH/乙酸乙酯(EA)研製、以MC溶解,經氧化矽過濾後,再以MC和正己烷研製獲得化合物C-2(5g,51.5%)。
MS/FAB實測值589;計算值586.68
將2,4-二氯喹唑啉(50g,251mmol)和二苯并[b,d]呋喃-4-基硼酸(53.2g,251mmol)溶解於甲苯(1L)與水(200mL)之混合液物後,加入Pd(PPh3)4(14.5g,12.5mmol)和Na2CO3(80g,755mmol)至該反應混合物,且於80℃攪拌20小時。將該反應混合物冷卻至室溫。以氯化銨水溶液200mL中止反應後,以乙酸乙酯(1L)萃取該反應混合物,再將以二氯甲烷(1L)萃取水層。所得有機層以無水硫酸鎂去除殘餘濕度並減壓去除有機溶劑。所得固體以矽膠過濾並減壓去除溶劑。所得固體以乙酸乙酯(100mL)清洗獲得化合物2-1(50g,74%)。
將H-苯并[c]咔唑(26g,122mmol)溶解於DMF後,將60% NaH(5.9g,148mmol)緩慢加入至該反應混合物,並於室溫攪拌1小時。將化合物2-1(51g,147mmol)加至該反應混合物,並於室溫攪拌20小時。將冰水緩慢滴入該反應混合物以中止反應,並過濾以獲得所產生的固體。所得固體以水(1L)、且接著以MeOH(1L)清洗。將所得固體乾燥並溶於CHCl3(4L),以矽膠過濾去除無機物。去除所得溶液中之溶劑以獲得固體。將所得固體以DMF再結晶以獲得化合物C-57(50g,58%)。
MS/FAB實測值512;計算值511.57
將2,4-二氯喹唑啉(50g,251mmol)和二苯并[b,d]呋喃-4-基硼酸(57.3g,251mmol)溶解於甲苯(1L)與水(200mL)之混合物中後,加入Pd(PPh3)4(14.5g,12.5mmol)和Na2CO3(80g,755mmol)至該反應混合物,且於80℃攪拌20小時。將該混合物冷卻至室溫。以氯化銨水溶液(200mL)中反應後,以乙酸乙酯(1L)萃取該反應混合物,再將以二氯甲烷(1L)萃取水層。所得有機層以無水硫酸鎂去除殘餘濕度並減壓去除有機溶劑。所得固體以矽膠過濾並減壓去
除溶劑。所得固體以乙酸乙酯(100mL)清洗獲得化合物3-1(50g,60%)。
將7H-苯并[c]咔唑(26g,122mmol)溶解於DMF後,將60% NaH(5.9g,148mmol)緩慢加入至該反應混合物,並於室溫攪拌1小時。將化合物3-1(51g,147mmol)加至該反應混合物,並於室溫攪拌20小時。將冰水緩慢滴入該反應混合物以中止反應,並過濾獲得所產生固體。所得固體以水(1L)、接著以MeOH(1L)清洗。將所得固體乾燥並溶於CHCl3(4L),以矽膠過濾去除無機物。去除所得溶液中之溶劑以獲得固體。所得固體以DMF再結晶可獲得化合物C-58(50g,57%)。
MS/FAB實測值528;計算值527.64
將7H-苯并[c]咔唑(7.3g,34.3mmol)、1-溴-4-碘苯(48.5g,171.4mmol)、CuI(3.3g,17.1mmol)、K3PO4(21.8g,102.9mmol)和乙二胺(EDA,2.3mL,34.3mmol)置入甲苯(500mL)後,迴流攪拌該反應混合物24小時。該反應混合物以乙酸乙酯萃取並減壓蒸餾後,以MC和己烷流通管柱過
濾可獲得化合物4-1(15.5g,80.1%)。
將化合物4-1(10.2g,27.5mmol)以四氫呋喃(THF)(250mL)溶解後,於-78℃加入2.5M n-BuLi之己烷溶液(17.6mL,44mmol)至該反應混合物,且攪拌該反應混合物1小時。該反應混合物攪拌2小時同時緩慢加入B(Oi-Pr)3(12.6mL,55mmol)至該反應混合物。於加入2M HCl淬滅該反應混合物後,以蒸餾水和乙酸乙酯萃取該反應混合物。減壓蒸餾所得有機層後,以MC和己烷再結晶獲得化合物4-2(8.7g,60%)。
將化合物2-1(3.2g,9.2mmol)、化合物4-2(3.1g,9.2mmol)、Pd(PPh3)4(532mg,0.46mmol)和Na2CO3(2.9g,27.6mmol)溶解於甲苯(55mL)、EtOH(14mL)和蒸餾水(14mL)之混合物中後,該反應混合物於90℃攪拌2小時。以水和EA萃取該反應混合物後,以MC和己烷流通管柱過濾可獲得化合物C-75(5.5g,75%)。
MS/FAB實測值588;計算值587.67
使用根據本發明之化合物製造OLED裝置。使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水清洗用於有機發光二極體(OLED)裝置(Samsung Corning,Republic of Korea)之玻璃基板上的透明電極銦錫氧化物(ITO)薄膜(15Ω/sq),並儲存於異丙醇中。然後,將ITO基板裝配於
真空氣相沉積裝置之基板夾持器上。將N1,N1’-([1,1’-聯苯]-4,4’-二基)雙(N1-(萘-1-基)-N4,N4-二苯基苯-1,4,-二胺)導入至該真空氣相沉積裝置之小室中,隨後該裝置的腔室壓力調控至10-6托(torr)。隨後對該小室施加電流來蒸發上述導入的材料,從而於ITO基板上形成厚度為60nm之電洞注入層。然後,將N,N’-二(4-聯苯)-N,N’-二(4-聯苯)-4,4’-二胺基聯苯導入至該真空氣相沉積裝置之另一小室中,且對該小室施加電流進行蒸發,從而於電洞注入層上形成厚度為20nm之電洞傳輸層。接著,將化合物C-2導入至該真空氣相沉積裝置之一小室中作為主體材料,並將化合物D-7導入至另一小室中作為摻雜劑。以不同速率蒸發該兩種材料,從而以摻雜量4wt%於該電洞傳輸層上沉積厚度為30nm之發光層。然後,將2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑導入至一小室中,並將8-羥基喹啉鋰(lithium quinolate)導入至另一小室中。以相同速率蒸發該兩種材料,從而以摻雜量50wt%於該發光層上沉積厚度為30nm之電子傳輸層。然後,將8-羥基喹啉鋰沉積於電子傳輸層上做為2nm之電子注入層後,用另一真空氣相沉積裝置在電子注入層上沈積厚度為150nm之鋁(Al)陰極。藉此而製造OLED。用於製造該OLED裝置之所有材料已各別於10-6 torr真空昇華予以純化。
所製造的OLED裝置顯示亮度1,030cd/cm2之紅光發射,以及於3.9V之驅動電壓有7.8mA/cm2之電流密度。更進一步地,亮度5,000尼特(nit)減少至90%之亮度最小時間為
80小時。
除了將化合物C-21作為主體材料並使用化合物D-11作為摻雜劑之外,如實施例1相同方式製造OLED。
所製造的OLED裝置顯示亮度1,020cd/cm2之紅光發射,以及於4.2V之驅動電壓有13.2mA/cm2之電流密度。更進一步地,亮度5,000尼特減少至90%之亮度最小時間為50小時。
除了將化合物C-57作為主體材料並使用化合物D-7作為摻雜劑之外,如實施例1相同方式製造OLED。
所製造的OLED裝置顯示亮度1,060cd/cm2之紅光發射,以及於3.9V之驅動電壓有7.8mA/cm2之電流密度。更進一步地,亮度5,000尼特減少至90%之亮度最小時間為100小時。
除了將化合物C-75作為主體材料並使用化合物D-11作為摻雜劑之外,如實施例1相同方式製造OLED。
所製造的OLED裝置顯示亮度1,050cd/cm2之紅光發射,以及於4.2V之驅動電壓有13.1mA/cm2之電流密度。更進一步地,亮度5,000尼特減少至90%之亮度最小時間為40小時。
除了將厚度30nm之發光層致以4,4’-N,N’-二咔唑基-
聯苯作為主體材料並以化合物D-11作為摻雜劑而沉積於電洞傳輸層上,且以雙(2-甲基-8-喹啉)-4-苯基酚鋁(III)沉積成厚度10nm之電洞阻擋層之外,如實施例1相同方式製造OLED。
所製造的OLED裝置顯示亮度1,000cd/cm2之紅光發射,以及於8.2V之驅動電壓有20mA/cm2之電流密度。更進一步地,亮度5,000尼特減少至90%之亮度最小時間為10小時。
與傳統材料相比,本發明之化合物具有較優的發光效率與較長壽命。含有本發明之化合物作為主體材料之裝置,藉由減少驅動電壓誘發功率效率增加,因此可改良耗電量與擁有較長的操作壽命。
Claims (6)
- 一種下式1表示之化合物,
- 如申請專利範圍第1項所述之化合物,其中在基團L1、L2、R1至R5、R6至R8和R11至R17中之該經取代之(伸)烷基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)環烷基、經取代之雜環烷基、經取代之芳烷基和經取代之伸烯基之取代基,各獨立為選自下列所成組群之至少一者:氘、鹵素、經鹵素取代或未經取代之 (C1-C30)烷基、(C6-C30)芳基、3-至30員雜芳基、(C3-C30)環烷基、3-至7員雜環烷基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基。
- 如申請專利範圍第1項所述之化合物,其中L1和L2係各獨立表示單鍵、3員至30員伸雜芳基、(C6-C30)伸芳基、或(C6-C30)伸環烷基;X1係表示CH或N;Y1係表示-O-、-S-、-CR6R7-或-NR8-;R1至R5係各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3員至30員雜芳基、N-咔唑基、NR11R12或-SiR13R14R15;或R4和R5各獨立連結至一個或多個鄰近取代基以形成環中之碳原子可被選自氮、氧和硫之至少一雜原子置換之單環或多環之(C5-C30)脂環族環或芳香族環;R6至R8係各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、或3員至30員雜芳基;R11至R15係各獨立表示(C1-C30)烷基、(C6-C30)芳 基、或3員至30員雜芳基;和L1和L2之該伸芳基、伸雜芳基和伸環烷基,和R1至R5和R11至R15之該烷基、芳基和雜芳基,各獨立可經選自下列所成組群之至少一者取代:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、(C1-C30)烷基(C6-C30)芳基、經(C6-C30)芳基經取代或未經取代之3員至30員雜芳基、(C3-C30)環烷基、和(C6-C30)芳基(C1-C30)烷基。
- 如申請專利範圍第1項所述之化合物,其中 該部分:係選自以下結構:
- 如申請專利範圍第1項所述之化合物,其中該式1表示之化合物係選自下列所成組群:
- 一種有機電場發光裝置,其包括申請專利範圍第1項所述之化合物。
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KR20110093055A (ko) * | 2010-02-11 | 2011-08-18 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR101477614B1 (ko) * | 2010-09-17 | 2014-12-31 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR20120038060A (ko) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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- 2012-05-30 US US14/123,338 patent/US20140100367A1/en not_active Abandoned
- 2012-05-30 CN CN201280037263.9A patent/CN103732590A/zh active Pending
- 2012-05-30 TW TW101119280A patent/TW201307329A/zh unknown
- 2012-05-30 JP JP2014513434A patent/JP2014522401A/ja active Pending
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TWI720829B (zh) * | 2019-02-28 | 2021-03-01 | 南韓商Lg化學股份有限公司 | 化合物以及包括其之有機發光裝置 |
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CN103732590A (zh) | 2014-04-16 |
WO2012165844A1 (en) | 2012-12-06 |
JP2014522401A (ja) | 2014-09-04 |
US20140100367A1 (en) | 2014-04-10 |
KR102008134B1 (ko) | 2019-08-09 |
KR20120132815A (ko) | 2012-12-10 |
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