TWI418547B - Aromatic amine derivatives and organic electroluminescent elements using the same - Google Patents
Aromatic amine derivatives and organic electroluminescent elements using the same Download PDFInfo
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- TWI418547B TWI418547B TW096112931A TW96112931A TWI418547B TW I418547 B TWI418547 B TW I418547B TW 096112931 A TW096112931 A TW 096112931A TW 96112931 A TW96112931 A TW 96112931A TW I418547 B TWI418547 B TW I418547B
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- Taiwan
- Prior art keywords
- group
- general formula
- substituted
- aromatic amine
- unsubstituted
- Prior art date
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- 150000004982 aromatic amines Chemical class 0.000 title claims description 71
- 238000005401 electroluminescence Methods 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 62
- 238000002347 injection Methods 0.000 claims description 51
- 239000007924 injection Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000010409 thin film Substances 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 150000001721 carbon Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 238000004020 luminiscence type Methods 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 claims description 2
- -1 (8-quinolinol) aluminum Chemical compound 0.000 description 266
- 239000010410 layer Substances 0.000 description 174
- 150000001875 compounds Chemical class 0.000 description 90
- 230000015572 biosynthetic process Effects 0.000 description 85
- 238000003786 synthesis reaction Methods 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 61
- 239000000543 intermediate Substances 0.000 description 59
- 239000010408 film Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 42
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 230000032258 transport Effects 0.000 description 25
- 229910052786 argon Inorganic materials 0.000 description 24
- 238000007740 vapor deposition Methods 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 19
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000004104 aryloxy group Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000007789 gas Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 238000009413 insulation Methods 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 125000005110 aryl thio group Chemical group 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 238000001771 vacuum deposition Methods 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 230000005684 electric field Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001454 anthracenes Chemical class 0.000 description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 150000003613 toluenes Chemical class 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 4
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 229910000420 cerium oxide Inorganic materials 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000008434 ginseng Nutrition 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 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 3
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000008425 anthrones Chemical class 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Chemical group 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical class OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 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
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
- BCZWPKDRLPGFFZ-UHFFFAOYSA-N azanylidynecerium Chemical compound [Ce]#N BCZWPKDRLPGFFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229950003621 butoxylate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical class C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- HHACNQLZWJFHIC-UHFFFAOYSA-N isocyano cyanate Chemical compound [C-]#[N+]OC#N HHACNQLZWJFHIC-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- MGFHWSFWSAJFQO-UHFFFAOYSA-N n-benzyl-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(=CC=1)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 MGFHWSFWSAJFQO-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
- 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 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OKQIEBVRUGLWOR-UHFFFAOYSA-N n-naphthalen-1-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1 OKQIEBVRUGLWOR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 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
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920002414 procyanidin Polymers 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000001275 scanning Auger electron spectroscopy Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-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
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Description
本發明係關於芳香族胺衍生物及使用其之有機電致發光(EL)元件，特別為使用具有特定取代基之芳香族胺衍生物於電洞輸送材料時，可抑制分子的結晶化，製造有機EL元件時可提高產率，有機EL元件壽命得到改善及實現此之芳香族胺衍生物者。
有機EL元件為藉由外加電場，利用藉著由陽極被注入之電洞、與由陰極被注入之電子的再結合能量使螢光性物質發光的原理之自發光元件。由耶司特門．可達克公司之C.W.Tang氏們所發表的藉由層合型元件之低電壓驅動有機EL元件的報告(C.W.Tang,S.A.Vanslyke,Applied Physics Letters,51卷、913頁、1987年等)以來，有關以有機材料作為構成材料之有機EL元件之研究正熱烈地被進行。Tang氏們使用參(8－喹啉酚)鋁於發光層，使用三苯基二胺衍生物於電洞輸送層。作為層合結構之優點，可舉出提高對發光層之電洞注入效率、提高經陰極被注入之電子經封止後再結合所生成之激發子的生成效率、封閉發光層內所生成之激發子等。如該例子，作為有機EL元件之元件結構已知有電洞輸送(注入)層、電子輸送發光層之2層型、或電洞輸送(注入)層、發光層、電子輸送(注入)層的3層型等。如此層合型結構元件中欲提高經注入之電洞與電子的再結合效率，對元件結構或形成方法上下工夫。
一般於高溫環境下使有機EL元件驅動而保管時，會產生發光色的變化、發光效率之降低、驅動電壓的上昇、發光壽命之短時間化等壞影響。欲預防此必須提高電洞輸送材料之玻璃轉移溫度(Tg)。因此，電洞輸送材料的分子內必須具有多數芳香族基(例如，專利文獻1的芳香族二胺衍生物、專利文獻2的芳香族縮合環二胺衍生物)，一般以具有8~12個苯環之結構為佳。
然而，分子內具有多數芳香族基時，使用此等之電洞輸送材料形成薄膜而製造有機EL元件時，容易引起結晶化，使用於蒸鍍之容器出口會被阻塞，產生因結晶化所引起的薄膜缺陷，導致有機EL元件的產率降低等問題。又，分子內具有多數芳香族基之化合物，一般為玻璃轉移溫度(Tg)較高者，有著昇華溫度高，引起蒸鍍時之分解或蒸鍍不均一等現象產生而使壽命減短之問題。
另一方面，已有揭示非對稱芳香族胺衍生物之公知文獻。例如，專利文獻3中記載具有非對稱結構之芳香族胺衍生物，但未有具體實施例，對於非對稱化合物之特徴亦完全無記載。又，專利文獻4中雖記載具有菲基之非對稱芳香族胺衍生物之實施例，與對稱化合物進行相同處理，且對於非對稱化合物之特徴完全無記載。又，即使非對稱化合物必須特殊合成法，此等專利中並未明確記載非對稱化合物之製造方法的相關內容。且，專利文獻5中雖記載具有非對稱結構之芳香族胺衍生物的製造法，但對於非對稱化合物之特徴則未記載。專利文獻6中雖記載玻璃轉移溫度高之熱安定的非對稱化合物，但僅例舉出具有咔唑之化合物。
又，作為具有二苯並呋喃之化合物的報告，可舉出專利文獻7~13，這些為於二胺化合物之中心骨架具有二苯並呋喃之結構。作為於末端上具有二苯並呋喃之化合物的報告，雖有專利14~15，但這些為單胺化合物。專利文獻8~12僅將此作為具體例而例舉出，專利文獻7與14中僅作為實際實施之感光體使用。作為有機EL元件雖於專利文獻13有記載但其性能並未充分。
如上述，雖有長壽命有機EL元件之報告，但未令人滿意。因此，強烈可望開發出具有更優良性能之有機EL元件。
[專利文獻1]美國專利第4,720,432號說明書[專利文獻2]美國專利第5,061,569號說明書[專利文獻3]特開平8－48656號公報[專利文獻4]特開平11－135261號公報[專利文獻5]特開2003－171366號公報[專利文獻6]美國專利第6,242,115號說明書[專利文獻7]專利第2501198號[專利文獻8]專利第2879370號[專利文獻9]專利第3508984號[專利文獻10]特開平5－34957號公報[專利文獻11]特開平7－287408號公報[專利文獻12]專利第3114445號[專利文獻13]特開2005－112765號公報[專利文獻14]專利第3248627號[專利文獻15]特開2001－288462號公報
本發明為解決上述課題所得者，故以製造出分子難以結晶化之有機EL元件時的產率提高，壽命較長之有機EL元件及實現此之芳香族胺衍生物為目的。
本發明者欲達成前述目的而詳細重複研究結果，將具有下述一般式(1)所示特定取代基之新穎芳香族胺衍生物作為有機EL元件用材料使用，特別作為電洞輸送材料使用時，發現可解決前述課題，而完成本發明。
又，發現作為具有特定取代基之胺單位，以具有一般式(2)或一般式(3)所示呋喃結構之芳基所取代之胺基為佳適。該胺單位因具有立體障害性故分子間的相互作用較小，故可抑制結晶化，製造有機EL元件時可提高產率，得到所得之有機EL元件的壽命延長效果，特別與藍色發光元件組合時，可得到顯著長壽命效果。
即，本發明為提供下述一般式(1)所示芳香族胺衍生物者。
本發明為提供下述一般式(5)所示芳香族胺衍生物者。
一般式(5)中，Ar7
~Ar9
中非一般式(3)者各獨立表示氫原子、取代或無取代之核原子數5~50的芳基、取代或無取代之碳數1~50的烷基、取代或無取代之碳數1~50的烷氧基、取代或無取代之碳數6~50的芳烷基、取代或無取代之核原子數5~50的芳氧基、取代或無取代之核原子數5~50的芳硫基、取代或無取代之碳數2~50的烷氧基羰基、取代或無取代之核原子數5~50的芳基所取代之胺基、鹵素原子、氰基、硝基、羥基、或羧基。〕
又，本發明為提供一種陰極與陽極間挾持至少含有發光層之一層或複數層所成的有機薄膜層之有機EL元件中，該有機薄膜層之至少1層含有前述芳香族胺衍生物作為單獨或混合物之成分的有機EL元件。
本發明的芳香族胺衍生物及使用其有機EL元件為分子難以結晶化，製造有機EL元件時可提高產率，且壽命長者。
本發明的芳香族胺衍生物為下述一般式(1)所示者。
一般式(1)中，R1
為氫原子、取代或無取代之核原子數5~50的芳基、取代或無取代之碳數1~50的烷基、取代或無取代之碳數1~50的烷氧基、取代或無取代之碳數6~50的芳烷基、取代或無取代之核原子數5~50的芳氧基、取代或無取代之核原子數5~50的芳硫基、取代或無取代之碳數2~50的烷氧基羰基、取代或無取代之核原子數5~50的芳基所取代之胺基、鹵素原子、氰基、硝基、羥基、或羧基。
一般式(1)中Ar1
~Ar4
中至少1個為下述一般式(2)或(3)所示。
一般式(2)中，R2
及R3
各獨立表示選自與前述一般式(1)之R1
的相同基。X為氧、硫、硒或碲，較佳為氧或硫原子，更佳為氧原子。
一般式(3)中，R4
~R6
各獨立表示選自與前述一般式(1)之R1
的相同基。X為氧或硫原子，較佳為氧原子。
作為一般式(1)~(3)之R1
~R6
的芳基例如可舉出苯基、1－萘基、2－萘基、1－蒽基、2－蒽基、9－蒽基、1－菲基、2－菲基、3－菲基、4－菲基、9－菲基、1－萘並萘基、2－萘並萘基、9－萘並萘基、1－芘基、2－芘基、4－芘基、2－聯苯基、3－聯苯基、4－聯苯基、p－聯三苯基4－基、p－聯三苯基3－基、p－聯三苯基2－基、m－聯三苯基4－基、m－聯三苯基3基、m－聯三苯基2－基、o－甲苯基、m－甲苯基、p－甲苯基、p－t－丁基苯基、p－(2－苯基丙基)苯基、3－甲基－2－萘基、4－甲基－1－萘基、4－甲基－1－蒽基、4’－甲基聯苯基、4”－t－丁基－p－聯三苯基4－基、熒蒽基、芴基、1－吡咯基、2－吡咯基、3－吡咯基、吡嗪基、2－吡啶基、3－吡啶基、4－吡啶基、1－吲哚基、2－吲哚基、3－吲哚基、4－吲哚基、5－吲哚基、6－吲哚基、7－吲哚基、1－異吲哚基、2－異吲哚基、3－異吲哚基、4－異吲哚基、5－異吲哚基、6－異吲哚基、7－異吲哚基、2－呋喃基、3－呋喃基、2－苯並呋喃、3－苯並呋喃、4－苯並呋喃、5－苯並呋喃、6－苯並呋喃、7－苯並呋喃、1－異苯並呋喃、3－異苯並呋喃、4－異苯並呋喃、5－異苯並呋喃、6－異苯並呋喃、7－異苯並呋喃、喹啉基、3－喹啉基、4－喹啉基、5－喹啉基、6－喹啉基、7－喹啉基、8－喹啉基、1－異喹啉基、3－異喹啉基、4－異喹啉基、5－異喹啉基、6－異喹啉基、7－異喹啉基、8－異喹啉基、2－喹喔啉基、5－喹喔啉基、6－喹喔啉基、1－咔唑基、2－咔唑基、3－咔唑基、4－咔唑基、9－咔唑基、1－菲啶基、2－菲啶基、3－菲啶基、4－菲啶基、6－菲啶基、7－菲啶基、8－菲啶基、9－菲啶基、10－菲啶基、1－吖啶基、2－吖啶基、3－吖啶基、4－吖啶基、9－吖啶基、1,7－菲繞啉－2－基、1,7－菲繞啉－3－基、1,7－菲繞啉－4－基、1,7－菲繞啉－5－基、1,7－菲繞啉－6－基、1,7－菲繞啉－8－基、1,7－菲繞啉－9－基、1,7－菲繞啉－10－基、1,8－菲繞啉－2－基、1,8－菲繞啉－3－基、1,8－菲繞啉－4－基、1,8－菲繞啉－5－基、1,8－菲繞啉－6－基、1,8－菲繞啉－7－基、1,8－菲繞啉－9基、1,8－菲繞啉－10－基、1,9－菲繞啉－2基、1,9－菲繞啉－3－基、1,9－菲繞啉－4－基、1,9－菲繞啉－5－基、1,9－菲繞啉－6－基、1,9－菲繞啉－7－基、1,9－菲繞啉－8－基、1,9－菲繞啉－10－基、1,10－菲繞啉－2－基、1,10－菲繞啉－3－基、1,10－菲繞啉－4－基、1,10－菲繞啉－5－基、2,9－菲繞啉－1－基、2,9－菲繞啉－3－基、2,9－菲繞啉－4－基、2,9－菲繞啉－5－基、2,9－菲繞啉－6－基、2,9－菲繞啉－7－基、2,9－菲繞啉－8－基、2,9－菲繞啉－10－基、2,8－菲繞啉－1－基、2,8－菲繞啉－3－基、2,8－菲繞啉－4－基、2,8－菲繞啉－5－基、2,8－菲繞啉－6－基、2,8－菲繞啉－7－基、2,8－菲繞啉－9－基、2,8－菲繞啉－10－基、2,7－菲繞啉－1－基、2,7－菲繞啉－3－基、2,7－菲繞啉－4－基、2,7－菲繞啉－5－基、2,7－菲繞啉－6－基、2,7－菲繞啉－8－基、2,7－菲繞啉－9－基、2,7－菲繞啉－10－基、1－吩嗪基、2－吩嗪基、1－吩噻嗪基、2－吩噻嗪基、3－吩噻嗪基、4－吩噻嗪基、10－吩噻嗪基、1－吩噁嗪基、2－吩噁嗪基、3－吩噁嗪基、4－吩噁嗪基、10－吩噁嗪基、2－噁唑基、4－噁唑基、5－噁唑基、2－噁二唑基、5－噁二唑基、3－呋咱基、2－噻吩基、3－噻吩基、2－甲基吡咯－1－基、2－甲基吡咯－3－基、2－甲基吡咯－4－基、2－甲基吡咯－5－基、3－甲基吡咯－1－基、3－甲基吡咯－2－基、3－甲基吡咯－4－基、3－甲基吡咯－5－基、2－t－丁基吡咯－4－基、3－(2－苯基丙基)吡咯－1－基、2－甲基－1－吲哚基、4－甲基－1－吲哚基、2－甲基－3－吲哚基、4－甲基－3－吲哚基、2－t－丁基1－吲哚基、4－t－丁基1－吲哚基、2－t－丁基3－吲哚基、4－t－丁基3－吲哚基等。
此等中，較佳為苯基、萘基、聯苯基、蒽基、菲基、芘基、1，2－苯並菲基、熒蒽基、芴基。
作為一般式(1)~(3)之R1
~R6
的烷基例如可舉出甲基、乙基、丙基、異丙基、n－丁基、s－丁基、異丁基、t－丁基、n－戊基、n－己基、n－庚基、n－辛基、羥基甲基、1－羥基乙基、2－羥基乙基、2－羥基異丁基、1,2－二羥基乙基、1,3－二羥基異丙基、2,3－二羥基－t－丁基、1,2,3－三羥基丙基、氯甲基、1－氯乙基、2－氯乙基、2－氯異丁基、1,2－二氯乙基、1,3－二氯異丙基、2,3－二氯－t－丁基、1,2,3－三氯丙基、溴甲基、1－溴乙基、2－溴乙基、2－溴異丁基、1,2－二溴乙基、1,3－二溴異丙基、2,3－二溴－t－丁基、1,2,3－三溴丙基、碘甲基、1－碘乙基、2－碘乙基、2－碘異丁基、1,2－二碘乙基、1,3－二碘異丙基、2,3－二碘－t－丁基、1,2,3－三碘丙基、胺甲基、1－胺乙基、2－胺乙基、2－胺異丁基、1,2－二胺乙基、1,3－二胺異丙基、2,3－二胺－t－丁基、1,2,3－三胺丙基、氰甲基、1－氰乙基、2－氰乙基、2－氰異丁基、1,2－二氰乙基、1,3－二氰異丙基、2,3－二氰－t－丁基、1,2,3－三氰丙基、硝甲基、1－硝乙基、2－硝乙基、2－硝異丁基、1,2－二硝乙基、1,3－二硝異丙基、2,3－二硝－t－丁基、1,2,3－三硝丙基、環丙基、環丁基、環戊基、環己基、4－甲基環己基、1－金剛烷基、2－金剛烷基、1－原菠烷基、2－原菠烷基等。
一般式(1)~(3)之R1
~R6
的烷氧基為－OY所示基，作為Y之例子可舉出與前述烷基所説明之同様例子。
作為一般式(1)~(3)之R1
~R6
的芳烷基，例如可舉出苯甲基、1－苯基乙基、2－苯基乙基、1－苯基異丙基、2－苯基異丙基、苯基－t－丁基、α－萘基甲基、1－α－萘基乙基、2－α－萘基乙基、1－α－萘基異丙基、2－α－萘基異丙基、β－萘基甲基、1－β－萘基乙基、2－β－萘基乙基、1－β－萘基異丙基、2－β－萘基異丙基、1－吡咯基甲基、2－(1－吡咯基)乙基、p－甲基苯甲基、m－甲基苯甲基、o－甲基苯甲基、p－氯苯甲基、m－氯苯甲基、o－氯苯甲基、p－溴苯甲基、m－溴苯甲基、o－溴苯甲基、p－碘苯甲基、m－碘苯甲基、o－碘苯甲基、p－羥基苯甲基、m－羥基苯甲基、o－羥基苯甲基、p－胺苯甲基、m－胺苯甲基、o－胺苯甲基、p－硝苯甲基、m硝苯甲基、o－硝苯甲基、p－氰苯甲基、m－氰苯甲基、o－氰苯甲基、1－羥基－2－苯基異丙基、1－氯－2－苯基異丙基等。
一般式(1)~(3)之R1
~R6
的芳氧基為－OY’所示，作為Y’之例子可舉出與前述芳基所説明之相同例子。
一般式(1)~(3)之R1
~R6
的芳硫基為－SY’所示，作為Y’的例可舉出與前述芳基所説明之相同例子。
一般式(1)~(3)之R1
~R6
的烷氧基羰基為－COOY所示基，作為Y的例子，可舉出與前述烷基所説明之同様例子。
作為一般式(1)~(3)之R1
~R6
的芳基所取代之胺基的芳基例，可舉出與前述芳基所説明之相同例子。
作為一般式(1)~(3)之R1
~R6
的鹵素原子，可舉出氟原子、氯原子、溴原子、碘原子等。
一般式(1)中，a為0~4之整數，b為1~3之整數，較佳為2。複數的R1
彼此可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。
一般式(2)中，c為0~6之整數，d為0~3之整數，e為1~3之整數，較佳為1。複數的R2
或R3
彼此可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。e為2以上而d非0時的複數之R3
可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。
一般式(3)中，f及h各為0~4之整數，g為0~3之整數，i為1~3的整數，較佳為1。複數的R4
或R5
或R6
彼此可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。i為2以上而h非0時之複數的R6
可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。
作為該可形成之5員環或6員環的環狀結構，例如可舉出環戊烷、環己烷、金剛烷、原菠烷等碳數4~12之環鏈烷、環戊烯、環己烯等碳數4~12之環鏈烯、環戊二烯、環己二烯等碳數6~12之環烷二烯、苯、萘、菲、蒽、芘、(Chrysene)、苊等碳數6~50的芳香族環等。
本發明之一般式(1)的芳香族胺衍生物為除取代基之碳數合計為42以上，54以上時為佳，60~80時為更佳。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中Ar1
與Ar2
為前述一般式(2)或前述一般式(3)所示。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中Ar1
與Ar3
為前述一般式(2)或前述一般式(3)所示。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中僅Ar1
為前述一般式(2)或前述一般式(3)所示。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中b為2。
本發明的芳香族胺衍生物，較佳為前述一般式(2)中f為1。
本發明的芳香族胺衍生物，較佳為前述一般式(3)中i為1。
本發明的芳香族胺衍生物，較佳為前述一般式(2)中X為氧原子。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中Ar2
為下述一般式(4)所示。
一般式(4)中，R7
為選自與前述一般式(1)之R1
相同基，具體例亦可舉出與一般式(1)~(3)之R1
~R6
的相同例子。
j為0~4之整數，k為1~3之整數。複數的R7
彼此可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。k為2以上而j非0時複數的R7
可互相結合形成飽和或不飽和的可經取代之5員環或6員環之環狀結構。此時的5員環或6員環之環狀結構的具體例亦可舉出與R1
~R6
之相同例子。
Ar5
及Ar6
各獨立表示一般式(3)、取代或無取代之核碳數6~50的芳基或取代或無取代之核碳數5~50的芳香族雜環基。該芳基或芳香族雜環基之具體例可舉出與R1
~R6
的芳基之相同例子。
本發明的芳香族胺衍生物，較佳為前述一般式(1)中Ar2
及Ar4
各獨立為前述一般式(4)所示。
本發明的芳香族胺衍生物如下述一般式(5)所示。
一般式(5)中，Ar7
~Ar9
中至少1個為前述一般式(3)所示，Ar1
~Ar3
中非一般式(3)者各獨立表示氫原子、取代或無取代之核原子數5~50的芳基、取代或無取代之碳數1~50的烷基、取代或無取代之碳數1~50的烷氧基、取代或無取代之碳數6~50的芳烷基、取代或無取代之核原子數5~50的芳氧基、取代或無取代之核原子數5~50的芳硫基、取代或無取代之碳數2~50的烷氧基羰基、取代或無取代之核原子數5~50的芳基所取代之胺基、鹵素原子、氰基、硝基、羥基、或羧基。此等之具體例亦可舉出與R1
~R6
之相同例子。
本發明的芳香族胺衍生物以有機電致發光元件用材料為佳。
本發明的芳香族胺衍生物以有機電致發光元件用電洞輸送材料為佳。
本發明的芳香族胺衍生物以有機電致發光元件用電洞注入材料為佳。
本發明的芳香族胺衍生物以同時具有有機電致發光元件用之電洞注入材料與電洞輸送材料的功能之材料為佳。
本發明的有機電致發光元件為，陰極與陽極間挾持至少含有發光層之一層或複數層所成的有機薄膜層之有機電致發光元件中，該有機薄膜層的至少1層為含有本發明的前述芳香族胺衍生物作為單獨或混合物成分為佳。
本發明的有機電致發光元件為，本發明的前述芳香族胺含於電洞輸送層時為佳。
本發明的有機電致發光元件為，本發明的前述芳香族胺含於電洞注入層時為佳。
本發明的有機電致發光元件為，於發光層含有苯乙烯基胺及/或芳基胺時為佳。
本發明的有機電致發光元件以藍色系發光為佳。
本發明的一般式(1)所示芳香族胺衍生物之具體例如下所示，但未限定於這些例示之化合物。
其次，對於本發明之有機EL元件做説明。
本發明的有機EL元件為，陰極與陽極間挾持至少含有發光層之一層或複數層所成的有機薄膜層之有機EL元件中，該有機薄膜層的至少1層含有前述芳香族胺衍生物作為單獨或混合物成分。
本發明的有機EL元件為，前述有機薄膜層具有電洞輸送層，該電洞輸送層含有本發明的芳香族胺衍生物作為單獨或混合物之成分為佳。且，前述電洞輸送層含有作為主成分之本發明的芳香族胺衍生物為佳。
本發明的芳香族胺衍生物，特別以使用於藍色系發光之有機EL元件為佳。
又，本發明之有機EL元件為，發光層含有芳基胺化合物及/或苯乙烯基胺化合物為佳。
作為芳基胺化合物可舉出下述一般式(1)所示化合物等，作為苯乙烯基胺化合物可舉出下述一般式(II)所示化合物等。
其中，作為碳數為6~20的芳香族基，以苯基、萘基、蒽基、菲基、聯三苯基等為佳。
其中，作為核原子數為5~40的芳基以苯基、萘基、蒽基、菲基、芘基、coronyl、聯苯基、聯三苯基、吡咯基、呋喃基、噻吩基、苯並噻吩基、噁二唑基、二苯基蒽基、吲哚基、咔唑基、吡啶基、苯並喹啉基、熒蒽基、苊並熒蒽基、二苯代乙烯等為佳。且，核原子數為5~40的芳基為，可進一步由取代基取代，作為較佳的取代基可舉出碳數1~6的烷基(乙基、甲基、i－丙基、n－丙基、s－丁基、t－丁基、戊基、己基、環戊基、環己基等)、碳數1~6的烷氧基(乙氧基、甲氧基、i－丙氧基、n－丙氧基、s－丁氧基、t－丁氧基、戊氧基、己氧基、環戊氧基、環己氧基等)、核原子數5~40的芳基、核原子數5~40的芳基所取代之胺基、具有核原子數5~40的芳基之酯基、具有碳數1~6的烷基之酯基、氰基、硝基、鹵素原子(氯、溴、碘等)。
以下，對於本發明之有機EL元件的元件構成做説明。
作為本發明的有機EL元件之代表元件構成，可舉出(1)陽極/發光層/陰極(2)陽極/電洞注入層/發光層/陰極(3)陽極/發光層/電子注入層/陰極(4)陽極/電洞注入層/發光層/電子注入層/陰極(5)陽極/有機半導體層/發光層/陰極(6)陽極/有機半導體層/電子障壁層/發光層/陰極(7)陽極/有機半導體層/發光層/附著改善層/陰極(8)陽極/電洞注入層/電洞輸送層/發光層/電子注入層/陰極(9)陽極/絕緣層/發光層/絕緣層/陰極(10)陽極/無機半導體層/絕緣層/發光層/絕緣層/陰極(11)陽極/有機半導體層/絕緣層/發光層/絕緣層/陰極(12)陽極/絕緣層/電洞注入層/電洞輸送層/發光層/絕緣層/陰極(13)陽極/絕緣層/電洞注入層/電洞輸送層/發光層/電子注入層/陰極等結構。
此等中一般使用(8)之構成為佳，但未限定於此。
本發明的芳香族胺衍生物，可使用於有機EL元件等之有機薄膜層，又可使用於發光區域或電洞輸送區域，較佳為使用於電洞輸送區域，特佳為使用於電洞輸送層而可使分子難以結晶化，且提高製造有機EL元件時的產率。
作為本發明的芳香族胺衍生物含於有機薄膜層之量，以30~100莫耳%為佳。
本發明的有機EL元件可於透光性之基板上製作。此所謂的透光性基板為支持有機EL元件之基板，400~700nm之可見光區域的光透過率為50%以上且平滑之基板為佳。
具體可舉出玻璃板、聚合物板等。作為玻璃板，特別可舉出鹼石灰玻璃、含有鋇.鍶之玻璃、鉛玻璃、鋁矽酸玻璃、硼矽酸玻璃、鋇硼矽酸玻璃、石英等。作為聚合物板可舉出聚碳酸酯、丙烯酸酯、聚對酞酸乙二酯、聚醚硫化物、聚碸等板。
本發明的有機EL元件之陽極為，具有將電洞注入於電洞輸送層或發光層之功能者，具有4.5eV以上之功函數時有效果。作為使用於本發明之陽極材料的具體例，可舉出氧化銦錫合金(ITO)、氧化錫(NESA)、銦－鋅氧化物(IZO)、金、銀、鉑、銅等。
陽極為可藉由此等電極物質以蒸鍍法或濺鍍法等方法形成薄膜後而製作。
如此自發光層之發光由陽極取出時，對於陽極發光的透過率比10%大時為佳。又，陽極的薄片電阻以數百Ω/□以下為佳。陽極的膜厚雖依據材料而不同，一般為選自10nm~1 μm，較佳為選自10~200nm之範圍。
有機EL元件之發光層為同時具有以下(1)~(3)之功能者。
(1)注入功能；電場外加時可由陽極或電洞注入層注入電洞，由陰極或電子注入層可注入電子之功能(2)輸送功能；將經注入之電荷(電子與電洞)以電場力移動之功能(3)發光功能；提供電子與電洞之再結合的場地，將此與發光連接的功能
但，電洞注入容易度與電子注入容易度即使相異亦可，又，電洞與電子移動度所示輸送能可相異，但移動任一方之電荷為佳。
作為形成該發光層之方法，例如可使用蒸鍍法、旋轉塗佈法、LB法等公知方法。發光層特別以分子堆積膜為佳。其中所謂分子堆積膜為，自氣相狀態之材料化合物沈澱後所形成之薄膜、或自溶液狀態或液相狀態之材料化合物經固化所形成之膜，通常該分子堆積膜為，與由LB法所形成之薄膜(分子累積膜)於凝集結構、高次結構之相異下、或其所引起的功能性相異而可區分。
又，又如特開昭57－51781號公報所揭示，樹脂等結著劑與材料化合物溶解於劑做成溶液後，即使將此藉由旋轉塗佈法等進行薄膜化，亦可形成發光層。
本發明中以不損害本發明的目的之範圍下，可依據所需於發光層中含有本發明的芳香族胺衍生物所成的發光材料以外之其他公知發光材料，又含有本發明的芳香族胺衍生物所成的發光材料之發光層中亦可層合含有其他公知發光材料之發光層。
與本發明的芳香族胺衍生物同時作為可使用於發光層之發光材料或摻合材料，例如可舉出蒽、萘、菲、芘、並四苯(tetracene)、六苯並苯(Coronene)、(Chrysene)、螢光素(Fluorescein)、苝、酞苝、萘酞苝、苝酮、酞苝酮、萘酞苝酮、二苯基丁二烯、四苯基丁二烯、香豆素、氧雜二唑基、醛連氮、雙苯並噁唑、雙苯乙烯基、吡嗪、環戊二烯、喹啉金屬錯合物、胺喹啉金屬錯合物、苯並喹啉金屬錯合物、亞胺、二苯基伸乙基、乙烯基蒽、二胺咔唑、吡喃、噻喃、聚甲川、部花青素、咪唑螯合化oxynoid化合物、喹吖啶酮、紅熒烯及螢光色素等，但未限定於此。
作為可與本發明的芳香族胺衍生物同時使用於發光層之主材料，以下述(i)~(ix)所示化合物為佳。
下述一般式(i)所示非對稱蒽。
下述一般式(ii)所示非對稱單蒽衍生物。
下述一般式(iii)所示非對稱芘衍生物。
下述一般式(iv)所示非對稱蒽衍生物。
下述一般式(v)所示蒽衍生物。
下述一般式(vi)所示蒽衍生物。
下述一般式(vii)所示螺芴衍生物。
下述一般式(viii)所示含有縮合環之化合物。
下述一般式(ix)所示芴化合物。
以上主材料中，較佳為蒽衍生物，更佳為單蒽衍生物，特佳為非對稱蒽。
又，作為摻雜之發光材料可使用磷光發光性之化合物。作為磷光發光性之化合物，主材料中含有咔唑環之化合物為佳。作為摻雜物可為自三重態激發子發光之化合物，但不限定於自三重態激發子發光者，以含有至少一種選自Ir、Ru、Pd、Pt、Os及Re所成群之金屬的金屬錯合物為佳，含有卟啉金屬錯合物或ortho－metallized金屬錯合物為佳。
含有咔唑環之化合物所成的磷光發光之較佳主材料為，由該激起狀態引起磷光發光性化合物之能量移動的結果，具有使磷光發光性化合物發光之功能的化合物。作為主化合物僅將激發子能量對磷光發光性化合物進行能量移動之化合物即可，並無特別限定，配合目的可適當地選擇。咔唑環以外可具有任意雜環等。
作為如此主化合物之具體例可舉出咔唑衍生物、三唑衍生物、噁唑衍生物、氧雜二唑基衍生物、咪唑衍生物、聚芳基鏈烷衍生物、吡唑衍生物、吡唑啉－5－酮衍生物、伸苯基二胺衍生物、芳基胺衍生物、胺取代芳基丙烯醯芳烴衍生物、苯乙烯基蒽衍生物、芴酮衍生物、水合肼衍生物、二苯代乙烯衍生物、矽氮烷衍生物、芳香族第三胺化合物、苯乙烯基胺化合物、芳香族二亞甲基系化合物、卟啉系化合物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯基醌衍生物、噻喃二氧化物衍生物、碳化二亞胺衍生物、亞芴甲烷衍生物、二苯乙烯基吡嗪衍生物、萘苝等雜環四羧酸酐、酞菁衍生物、8－羥基喹啉衍生物之金屬錯合物化金屬酞菁、苯並噁唑或苯並噻唑作為配位子的金屬錯合物作為代表的各種金屬錯合物聚矽烷系化合物、聚(N－乙烯基咔唑)衍生物、苯胺系共聚物、噻吩寡聚物、聚噻吩等導電性高分子寡聚物、聚噻吩衍生物、聚伸苯基衍生物、聚伸苯基伸乙烯衍生物、聚芴衍生物等高分子化合物等。主化合物可單獨使用或合併2種以上使用。
作為具體例可舉出如以下之化合物。
磷光發光性之摻雜物為可自三重態激發子進行發光之化合物。但不限定於自三重態激發子發光者，以含有至少一種選自Ir、Ru、Pd、Pt、Os及Re所成群之金屬的金屬錯合物為佳，卟啉金屬錯合物或ortho－metallized金屬錯合物為更佳。作為卟啉金屬錯合物以卟啉鉑錯合物為佳。磷光發光性化合物可單獨使用或合併2種以上使用。
作為形成ortho－metallized金屬錯合物之配位子，可為種種類型，作為較佳配位子可舉出2－苯基吡啶衍生物、7,8－苯並喹啉衍生物、2－(2－噻吩基)吡啶衍生物、2－(1－萘基)吡啶衍生物、2－苯基喹啉衍生物等。這些衍生物可依所需具有取代基。特別以導入氟化物、三氟甲基者中作為藍色系摻雜物為佳。且作為補助配位子，可具有乙醯丙酮、苦味酸等上述配位子以外的配位子為佳。
作為磷光發光性之摻雜物於發光層之含有量，並無特別限定，可配合目的做適當選擇，例如0.1~70質量%，以1~30質量%為佳。磷光發光性化合物的含有量若未達0.1質量%時發光微弱使其含有效果未能充分發揮，若超過70質量%時，所謂濃度消光之現象會顯著使元件性能降低。
又，發光層若必要可含有電洞輸送材、電子輸送材、聚合物黏著劑。
且，發光層的膜厚，較佳為5~50nm，更佳為7~50nm，最佳為10~50nm。未達5nm時難形成發光層，色度的調整恐怕難以達成，若超過50nm時，驅動電壓恐怕會上升。
電洞注入．輸送層可幫助對發光層的電洞注入，其輸送至發光區域之層，電洞移動度較大，離子化能量一般為較小之5.5eV以下。作為如此電洞注入．輸送層，於較低電場強度下可將電洞運送至發光層之材料為佳，且電洞之移動度，例如104
~106
V/cm之電場外加時，僅至少為10－4
cm2
/V．秒即可。
將本發明的芳香族胺衍生物使用於電洞輸送區域時，本發明的芳香族胺衍生物可單獨下形成電洞注入、輸送層，可與其他材料混合後使用。
作為與本發明的芳香族胺衍生物混合後形成電洞注入．輸送層之材料，僅具有前述較佳性質者即可，並無特別限定，可任意選自過去於光傳導材料中，作為電洞之電荷輸送材料所慣用者、或使用於有機EL元件之電洞注入．輸送層之公知者後使用。
作為具體例，可舉出三唑衍生物(參照美國專利3,112,197號說明書等)、氧雜二唑基衍生物(參照美國專利3,189,447號說明書等)、咪唑衍生物(參照特公昭37－16096號公報等)、聚芳基鏈烷衍生物(參照美國專利3,615,402號說明書、同第3,820,989號說明書、同第3,542,544號說明書、特公昭45－555號公報、同51－10983號公報、特開昭51－93224號公報、同55－17105號公報、同56－4148號公報、同55－108667號公報、同55－156953號公報、同56－36656號公報等)、吡唑衍生物及吡唑啉－5－酮衍生物(參照美國專利第3,180,729號說明書、同第4,278,746號說明書、特開昭55－88064號公報、同55－88065號公報、同49－105537號公報、同55－51086號公報、同56－80051號公報、同56－88141號公報、同57－45545號公報、同54－112637號公報、同55－74546號公報等)、伸苯基二胺衍生物(參照美國專利第3,615,404號說明書、特公昭51－10105號公報、同46－3712號公報、同47－25336號公報、特開昭54－53435號公報、同54－110536號公報、同54－119925號公報等)、芳基胺衍生物(參照美國專利第3,567,450號說明書、同第3,180,703號說明書、同第3,240,597號說明書、同第3,658,520號說明書、同第4,232,103號說明書、同第4,175,961號說明書、同第4,012,376號說明書、特公昭49－35702號公報、同39－27577號公報、特開昭55－144250號公報、同56－119132號公報、同56－22437號公報、西德專利第1,110,518號說明書等)、胺取代芳基丙烯醯芳烴衍生物(參照美國專利第3,526,501號說明書等)、噁唑衍生物(參照美國專利第3,257,203號說明書等所揭示者)、苯乙烯基蒽衍生物(參照特開昭56－46234號公報等)、芴酮衍生物(參照特開昭54－110837號公報等)、水合肼衍生物(參照美國專利第3,717,462號說明書、特開昭54－59143號公報、同55－52063號公報、同55－52064號公報、同55－46760號公報、同55－85495號公報、同57－11350號公報、同57－148749號公報、特開平2－311591號公報等)、二苯代乙烯衍生物(參照特開昭61－210363號公報、同第61－228451號公報、同61－14642號公報、同61－72255號公報、同62－47646號公報、同62－36674號公報、同62－10652號公報、同62－30255號公報、同60－93455號公報、同60－94462號公報、同60－174749號公報、同60－175052號公報等)、矽氮烷衍生物(參照美國專利第4,950,950號說明書)、聚矽烷系(參照特開平2－204996號公報)、苯胺系共聚物(參照特開平2－282263號公報)、特開平1－211399號公報所揭示之導電性高分子寡聚物(特別為噻吩寡聚物)等。
作為電洞注入．輸送層之材料可使用上述者，使用卟啉化合物(參照特開昭63－2956965號公報等所揭示者)、芳香族第三級胺化合物及苯乙烯基胺化合物(參照美國專利第4,127,412號說明書、特開昭53－27033號公報、同54－58445號公報、同54－149634號公報、同54－64299號公報、同55－79450號公報、同55－144250號公報、同56－119132號公報、同61－295558號公報、同61－98353號公報、同63－295695號公報等)，特別以使用芳香族第三級胺化合物為佳。
又，美國專利第5,061,569號所記載的分子內具有2個縮合芳香族環者，例如可舉出4，4’－雙(N－(1－萘基)－N－苯基胺)聯苯基(以下簡稱為NPD)，又特開平4－308688號公報所記載的三苯基胺單位連結成3個星暴增型之4,4’,4”－參(N－(3－甲基苯基)－N－苯基胺)三苯基胺(以下簡稱為MTDATA)等。
且，作為發光層之材料所示的前述芳香族二次甲基系化合物以外，亦可將其他p型Si、p型SiC等無機化合物作為電洞注入．輸送層之材料使用。
其他亦可使用專利3571977號所揭示的下述式所示含氮雜環衍生物。
式中，R121
~R126
各表示取代或無取代之烷基、取代或無取代之芳基、取代或無取代之芳烷基、取代或無取代之雜環基。但，R121
~R126
可為相同或相異。又，R121
與R122
、R122
與R123
、R123
與R124
、R124
與R125
、R125
與R126
、及R126
與R121
可形成縮合環。
且，亦可使用美國公開2004/0113547所記載的下述式化合物。
式中，R131~R136為取代基，較佳為氰基、硝基、磺醯基、羰基、三氟甲基、鹵素原子等電子吸引基。
如代表如此材料，受體性材料亦可作為電洞注入材料使用。此等具體例如上述。
又，作為發光層之材料所示的前述芳香族二次甲基系化合物以外，亦可使用p型Si、p型SiC等無機化合物作為電洞注入層之材料。
電洞注入．輸送層為，本發明的芳香族胺衍生物藉由例如真空蒸鍍法、旋轉塗佈法、鑄模法、LB法等公知方法進行薄膜化而形成。作為電洞注入．輸送層之膜厚雖無特別限定，一般為5nm~5 μm。該電洞注入．輸送層為，僅於電洞輸送區域含有本發明的芳香族胺衍生物，可由一種或二種以上之上述材料所成之一層所構成，前述電洞注入．輸送層可為層合別種化合物所成之電洞注入．輸送層者。
又，作為幫助於發光層之電洞注入或電子注入的層，可設置有機半導體層，具有10－10
S/cm以上之導電率者為佳。作為如此有機半導體層之材料，可使用含噻吩寡聚物或特開平8－193191號公報所揭示的含芳基胺寡聚物等導電性寡聚物、含芳基胺樹狀聚合物等導電性樹狀聚合物等。
其次，電子注入層．輸送層為，可幫助於發光層之電子注入，其為輸送至發光區域之層，電子移動度較大，又附著改善層為，該電子注入層中特別與陰極之附著優良之材料所成的層。
又，已知有機EL元件為發光之光因藉由電極(此時為陰極)而反射，直接由陽極所取出之發光、與經由藉電極之反射所取出之發光會產生干涉現象。欲有效地利用該干渉效果，電子輸送層可適宜地選自數nm~數μm之膜厚，特別為膜厚較厚時，欲避免電壓上昇，104
~106
V/cm之電場外加時電子移動度至少為10－5
cm2
/Vs以上者為佳。
作為使用於電子注入層之材料，可使用8－羥基喹啉或其衍生物之金屬錯合物或氧雜二唑基衍生物為佳。作為上述8－羥基喹啉或其衍生物之金屬錯合物之具體例，可使用含有Oxine(一般為8－ Quinolinol或8－羥基喹啉)之螯合的金屬螯合oxynoid化合物，例如可使用參(8－羥基喹啉)鋁作為電子注入材料。
另一方面，作為雜二唑基衍生物可舉出以下一般式所示電子傳達化合物。
其中作為芳基可舉出苯基、聯苯基、蒽基、苝基、芘基。又，作為伸芳基可舉出伸苯基、伸萘基、聯伸苯基、伸蒽基、伸苝基、伸芘基等。又，作為取代基可舉出碳數1~10的烷基、碳數1~10的烷氧基或氰基等。該電子傳達化合物以薄膜形成性者為佳。
作為上述電子傳達性化合物之具體例可舉出下述者。
且，作為使用於電子注入層及電子輸送層之材料，可使用下述一般式(A)~(F)所示者。
Ar1
為取代或無取代之核碳數6~60的芳基、或取代或無取代之核碳數3~60的雜芳基，Ar2
為氫原子、取代或無取代之核碳數6~60的芳基、取代或無取代之核碳數3~60的雜芳基、取代或無取代之碳數1~20的烷基、或取代或無取代之碳數1~20的烷氧基、或此等之2價基。但，Ar1
及Ar2
之任一方為取代或無取代之核碳數10~60之縮合環基、或取代或無取代之核碳數3~60之單雜縮合環基。
L1
、L2
及L各獨立表示單鍵、取代或無取代之核碳數6~60的伸芳基、取代或無取代之核碳數3~60的雜伸芳基、或取代或無取代之伸芴基。
R為氫原子、取代或無取代之核碳數6~60的芳基、取代或無取代之核碳數3~60的雜芳基、取代或無取代之碳數1~20的烷基、或取代或無取代之碳數1~20的烷氧基，n為0~5之整數，n為2以上時，複數的R可為相同或相異，又，鄰接之複數R基彼此可結合形成碳環式脂肪族環或碳環式芳香族環。)所示含氮雜環衍生物。
H Ar－L－Ar1
－Ar2
(C)(式中，H Ar為可具有取代基的碳數3~40的含氮雜環，L為單鍵、可具有取代基的碳數6~60的伸芳基、可具有取代基的碳數3~60的雜伸芳基或可具有取代基的伸芴基，Ar1
為可具有取代基的碳數6~60之2價芳香族烴基，Ar2
為可具有取代基的碳數6~60的芳基或可具有取代基的碳數3~60的雜芳基。)所示含氮雜環衍生物。
該金屬錯合物作為n型半導體之性質為強，電子注入能力較大。且因錯合物形成時的生成能量亦較低，形成之金屬錯合物的金屬與配位子之結合性亦變強固，作為發光材料之螢光量子效率亦變大。
作為形成一般式(G)之配位子的環A1
及A2
的取代基之具體例，可舉出氯、溴、碘、氟之鹵素原子、甲基、乙基、丙基、丁基、s－丁基、t－丁基、戊基、己基、庚基、辛基、硬脂基、三氯甲基等取代或無取代之烷基、苯基、萘基、3－甲基苯基、3－甲氧基苯基、3－氟苯基、3－三氯甲基苯基、3－三氟甲基苯基、3－硝苯基等取代或無取代之芳基、甲氧基、n－丁氧基、t－丁氧基、三氯甲氧基、三氟乙氧基、五氟丙氧基、2,2,3,3－四氟丙氧基、1,1,1,3,3,3－六氟－2－丙氧基、6－(全氟乙基)己氧基等取代或無取代之烷氧基、苯氧基、p－硝苯氧基、p－t－丁基苯氧基、3－氟苯氧基、五氟苯基、3－三氟甲基苯氧基等取代或無取代之芳氧基、甲硫基、乙硫基、t－丁硫基、己硫基、辛硫基、三氟甲硫基等取代或無取代之烷硫基、苯硫基、p－硝苯硫基、p－t－丁基苯硫基、3－氟苯硫基、五氟苯硫基、3－三氟甲基苯硫基等取代或無取代之芳硫基、氰基、硝基、胺基、甲基胺基、二乙胺基、乙基胺基、二乙胺基、二丙基胺基、二丁基胺基、二苯基胺基等單或二取代胺基、雙(乙醯氧基甲基)胺基、雙(乙醯氧基乙基)胺基、雙乙醯氧基丙基)胺基、雙(乙醯氧基丁基)胺基等醯基胺基、羥基、矽氧烷基、醯基、甲基胺基甲醯基、二甲基胺基甲醯基、乙基胺基甲醯基、二乙基胺基甲醯基、丙基胺基甲醯基、丁基胺基甲醯基、苯基胺基甲醯基等胺基甲醯基、羧酸基、磺酸基、亞胺基、環戊基、環己基等環烷基、苯基、萘基、聯苯基、蒽基、菲基、芴基、芘基等芳基、吡啶基、吡嗪基、嘧啶基、噠嗪基、三嗪基、吲哚滿基、喹啉基、吖啶基、吡咯烷基、二噁烷基、哌啶基、嗎啉啶基、哌嗪基、tria tinyl、咔唑基、呋喃基、噻吩基、噁唑基、噁二唑基、苯並噁唑基、噻唑基、噻二唑、苯並噻唑基、三唑基、咪唑基、苯並咪唑基、吡喃基等雜環基等。又，以上的取代基彼此結合可進一步形成6員芳基環或雜環。
本發明有機EL元件之較佳形態中有含有還原性摻雜物的元件，輸送電子之區域或陰極與有機層的界面區域中有含有還原性摻雜物的元件。其中所謂還原性摻雜物定義為可還原電子輸送性化合物之物質。因此，僅具有一定還原性者即可，可使用種種物質，例如可舉出至少1種選自鹼金屬、鹼土類金屬、稀土類金屬、鹼金屬的氧化物、鹼金屬的鹵化物、鹼土類金屬的氧化物、鹼土類金屬的鹵化物、稀土類金屬的氧化物或稀土類金屬的鹵化物、鹼金屬之有機錯合物、鹼土類金屬之有機錯合物、稀土類金屬之有機錯合物所成群之物質。
又，更具體之作為較佳還原性摻雜物為至少1種選自Na(功函數：2.36eV)、K(功函數：2.28eV)、Rb(功函數：2.16eV)及Cs(功函數：1.95eV)所成群之鹼金屬、或至少1種選自Ca(功函數：2.9eV)、Sr(功函數：2.0~2.5eV)、及Ba(功函數：2.52eV)所成群之鹼土類金屬，功函數為2.9eV以下者為特佳。其中較佳的還原性摻雜物為至少1種選自K、Rb及Cs所成群之鹼金屬，更佳為Rb或Cs，最佳為Cs。此等之鹼金屬特別具有較高還原能力，藉由對於電子注入區域之較少量的，可達到有機EL元件之發光亮度的提高或長壽命化。又，作為功函數為2.9eV以下之還原性摻雜物，以這些2種以上之鹼金屬組合為佳，特別為含有Cs之組合，例如以Cs與Na、Cs與K、Cs與Rb或Cs與Na與K之組合為佳。藉由含有組合Cs可有效率地發揮還原能力，藉由對電子注入區域之添加，可達到有機EL元件之發光亮度的提高或長壽命化。
本發明中，陰極與有機層之間可進一步設置絕緣體或半導體所構成之電子注入層。此時可有效防止漏電，可提高電子注入性。作為如此絕緣體，使用至少1種選自鹼金屬硫屬化物、鹼土類金屬硫屬化物、鹼金屬的鹵化物及鹼土類金屬的鹵化物所成群之金屬化合物為佳。電子注入層僅由這些鹼金屬硫屬化物等所構成即可，電子注入性可進一步提高而較佳。作為具體較佳鹼金屬硫屬化物，例如可舉出Li2
O、K2
O、Na2
S、Na2
Se及Na2
O，作為較佳鹼土類金屬硫屬化物，例如可舉出CaO、BaO、SrO、BeO、BaS、及CaSe。又，作為較佳鹼金屬的鹵化物，例如可舉出LiF、NaF、KF、LiCl、KCl及NaCl等。又，作為較佳鹼土類金屬的鹵化物，例如可舉出CaF2
、BaF2
、SrF2
、MgF2
及BeF2
之氟化物、或氟化物以外的鹵化物。
又，作為構成電子輸送層之半導體，可舉出含有至少1個選自Ba、Ca、Sr、Yb、Al、Ga、In、Li、Na、Cd、Mg、Si、Ta、Sb及Zn之元素的氧化物、氮化物或氧化氮化物等一種單獨或二種以上的組合。又，構成電子輸送層之無機化合物為微結晶或非晶質之絕緣性薄膜為佳。電子輸送層僅由這些絕緣性薄膜所構成即可，欲形成更均質之薄膜，可減少黑點等畫素缺陷。且，作為如此無機化合物可舉出如上述的鹼金屬硫屬化物、鹼土類金屬硫屬化物、鹼金屬的鹵化物及鹼土類金屬的鹵化物等。
作為陰極，可使用欲將電子注入於電子注入．輸送層或發光層時，功函數較小的(4eV以下)金屬、合金、電傳導性化合物及這些混合物作為電極物質者。作為如此電極物質之具體例可舉出鈉、鈉．鉀合金、鎂、鋰、鎂．銀合金、鋁/氧化鋁、鋁．鋰合金、銦、稀土類金屬等。
該陰極可藉由將這些電極物質經蒸鍍或濺鍍等方法形成薄膜而製作。
其中由發光層之發光自陰極取出時，對於陰極之發光之透過率比10%大時為佳。
又，作為陰極之薄片電阻以數百Ω/□以下者為佳，膜厚一般為10nm~1 μm，較佳為50~200nm。
有機EL元件於超薄膜上外加電場，故容易產生因漏電或短路所引起的畫素缺陷。為防止此，一對電極間插入絕緣性薄膜層為佳。
作為絕緣層所使用的材料，例如可舉出氧化鋁、氟化鋰、氧化鋰、氟化銫、氧化銫、氧化鎂、氟化鎂、氧化鈣、氟化鈣、氮化鋁、氧化鈦、氧化矽、氧化鍺、氮化矽、氮化硼、氧化鉬、氧化釕、氧化鈀等，亦可使用這些混合物或層合物。
藉由以上例示之材料及形成方法，形成陽極、發光層、若必要形成電洞注入．輸送層、及若必要形成電子注入．輸送層，且藉由形成陰極可製造出有機EL元件。又，可自陰極至陽極，以前述相反的順序製造出有機EL元件。
以下記載以透光性基板上陽極/電洞注入層/發光層/電子注入層/陰極的順序所設置構成的有機EL元件之製作例子。
首先於適當透光性基板上將陽極材料所成的薄膜以蒸鍍或濺鍍等方法形成如1 μm以下，較佳為10~200nm範圍之膜厚而製作出陽極。其次於該陽極上設置電洞注入層。電洞注入層之形成如前述可由真空蒸鍍法、旋轉塗佈法、鑄模法、LB法等方法進行，但由可容易得到均質膜，且針孔難產生等點來看，藉由真空蒸鍍法形成為佳。藉由真空蒸鍍法形成電洞注入層時，該蒸鍍條件依據所使用之化合物(電洞注入層之材料)、作為目的之電洞注入層的結晶結構或再結合結構等而不同，但一般可適宜地選自蒸鍍源溫度50~450℃、真空度10－7
~10－3
Torr、蒸鍍速度0.01~50nm/秒、基板溫度－50~300℃、膜厚5nm~5 μm之範圍為佳。
其次，電洞注入層上設置發光層之發光層的形成，亦可使用所望的有機發光材料藉由真空蒸鍍法、濺鍍、旋轉塗佈法、鑄模法等方法使有機發光材料薄膜化後可形成，但由可容易得到均質膜，且針孔難產生等點來看，藉由真空蒸鍍法形成為佳。藉由真空蒸鍍法形成發光層時，該蒸鍍條件依據所使用的化合物而相異，可選自與一般電洞注入層相同條件範圍中者。
其次，該發光層上設置電子注入層。與電洞注入層、發光層同様地，由可得到均質膜之點來看以真空蒸鍍法形成為佳。蒸鍍條件可由與電洞注入層、發光層同様條件範圍中選擇。
本發明的芳香族胺衍生物雖依含於發光區域或電洞輸送區域之任一層而不同，但使用真空蒸鍍法時可與其他材料進行共蒸鍍。又，使用旋轉塗佈法時，可經與其他材料混合而含有。
最後層合陰極而得到有機EL元件。
陰極係由金屬所構成，可使用蒸鍍法、濺鍍。然而欲保護底材之有機物層於製膜時的損傷以使用真空蒸鍍法為佳。
該有機EL元件之製作為一次真空下一貫地由陽極製作至陰極為佳。
本發明的有機EL元件之各層的形成方法並無特別限定。可使用過去公知之真空蒸鍍法、旋轉塗佈法等之形成方法。本發明有機EL元件所使用的含有前述一般式(1)所示之化合物的有機薄膜層可由真空蒸鍍法、分子線蒸鍍法(MBE法)或溶解於溶劑之溶液浸漬法、旋轉塗佈法、澆注法、棒塗佈法、滾筒塗佈法等塗佈法等公知方法形成。
本發明的有機EL元件之各有機層的膜厚並無特別限定，一般若膜厚過薄時容易產生針孔等缺陷，相反地若過厚則必須較高外加電壓而使效率變差，一般為數nm至1 μm之範圍為佳。
且於有機EL元件外加直流電壓時，使陽極為＋，陰極為－之極性，外加5~40V的電壓時可以觀測到發光。又，即使以相反極性外加電壓亦無法使電流流動，且完全無法發光。且外加交流電壓時，僅陽極為＋、陰極為－之極性時，可觀測到均一發光。外加之交流波形可為任意形式。
以下本發明依據合成例及實施例作更詳細説明。合成例1~14中所合成的中間體1~14的結構如下述。
氬氣流下，1000mL的三口燒瓶中放入4－溴聯苯基47g、碘23g、過碘酸2水合物9.4g、水42mL、乙酸360mL、硫酸11mL，於65℃下攪拌30分鐘後，90℃下進行6小時反應。將反應物注入冰水中並過濾。以水洗淨，並以甲醇洗淨後得到67g之白色粉末。藉由FD－MS分析，鑑定為對於C12
H15
BrI＝359之m/z＝358與360的主吸收峰，故鑑定為中間體1。
氬氣流下，300mL的三口燒瓶中加入p－聯三苯基10g、碘12g、過碘酸2水合物4.9g、水20mL、乙酸170mL、硫酸22mL，並於65℃下攪拌30分鐘後，於90℃下進行6小時反應。將反應物注入冰水中並過濾。以水洗淨，並以甲醇洗淨後得到18g之白色粉末。藉由FD－MS分析，鑑定為對於C18
H12
I2
＝482之m/z＝482的主吸收峰，故鑑定為中間體2。
氬氣流下，1000mL的三口燒瓶中放入4－二苯並呋喃硼酸42.4g、4－碘溴苯56.0g、肆(三苯基膦)鈀(Pd(PPh3
)4
)6.9g、2M之碳酸鈉(Na2
CO3
)溶液320mL、甲苯320mL後，80℃下進行8小時反應。反應液以甲苯/水萃取，以無水硫酸鈉乾燥。將此於減壓下濃縮所得之粗生成物以管柱純化而得到28.5g之白色粉末。藉由FD－MS分析，鑑定為中間體3。
合成例3中取代4－碘溴苯而使用71g的中間體1以外，進行相同反應後得到42.4g之白色粉末。藉由FD－MS分析，鑑定為中間體3。
氬氣流下，500mL的三口燒瓶中加入文獻記載(J.Org.Chem；62；5；1997；1348－1355)之合成法所得的2－溴二苯並呋喃24.9g、脫水醚80mL及脫水甲苯80mL。－30℃下投入n－丁基鋰/己烷溶液120mmol，0℃下進行1h反應。冷卻至－70℃，投入70mL之硼酸三異丙基(B(OiPr)3
)，慢慢昇溫至室溫並攪拌1h。加入10%鹽酸80mL者以乙酸乙酯/水進行萃取後，以無水硫酸鈉乾燥。濃縮溶液並以己烷洗淨而得到硼酸化物10.4g。
合成例3中取代4－二苯並呋喃硼酸使用上述所得之2－二苯並呋喃硼酸42.4g以外，進行同様反應後得到24.6g之白色粉末。藉由FD－MS分析，鑑定為中間體5。
氬氣流下，放入苯胺5.5g、中間體316.2g、t－丁氧基鈉6.8g(廣和光公司製)、參(二亞芐基丙酮)二鈀(0)0.46g(Aldrich製)及脫水甲苯300mL，80℃下進行8小時反應。
冷卻後加入水500mL，混合物經矽藻石過濾，濾液以甲苯萃取，以無水硫酸鎂進行乾燥。將此於減壓下進行濃縮，將所得之粗生成物以管柱純化，再以甲苯進行再結晶，將此過濾並乾燥後，得到10.1g之淡黃色粉末。藉由FD－MS分析，鑑定為中間體6。
氬氣流下，放入中間體6 10g、1－溴－4－碘苯8.8g(Aldrich製)、t－丁氧基鈉3g(廣和光公司製)、雙(三苯基膦)氯化鈀(II)0.5g(東京化成公司製)及二甲苯500mL，於130℃下進行24小時反應。
冷卻後加入水1000mL，將混合物以矽藻石過濾，將濾液以甲苯萃取，再以無水硫酸鎂乾燥。將此於減壓下濃縮，所得之粗生成物以管柱純化，再以甲苯進行再結晶，將此過濾並乾燥後，得到3.2g之淡黃色粉末。藉由FD－MS分析，鑑定為中間體7。
合成例3中，取代4－碘溴苯使用4－溴苯胺71g以外，進行同様反應後得到26.4g之白色粉末。藉由FD－MS分析，鑑定為中間體8。
合成例7中，取代中間體3使用二苯基胺5.2g，取代1－溴－4－碘苯使用11.0g的中間體1以外，進行同様反應後得到2.6g之白色粉末。藉由FD－MS分析，鑑定為中間體9。
合成例6中取代苯胺使用13.0g的中間體8，取代中間體4使用4－溴聯苯基11.6g以外，進行同様反應下得到13.1g之白色粉末。藉由FD－MS分析，鑑定為中間體10。
氬氣流下，注入1－乙醯胺基萘547g(東京化成公司製)、4,4’－二碘聯苯基400g(和光純藥公司製)、碳酸鉀544g(和光純藥公司製)、銅粉12.5g(和光純藥公司製)及萘烷2LM，190℃下進行4天反應。
反應後冷卻後添加甲苯2L，過濾不溶部分。濾取物溶解於氯仿4.5L，除去不溶部分後，以活性碳處理並濃縮。於此加入丙酮3L，過濾析出晶382g。
將此懸浮於乙二醇5L(和光純藥公司製)、水50mL，添加85%水氧化鉀水溶液145g後，120℃下進行2小時反應。
反應後，於水10L中注入反應液，過濾析出晶後以水、甲醇洗淨。所得之結晶於四氫呋喃3L中進行加熱溶解，以活性碳處理後濃縮，加入丙酮後析出結晶。將此經過濾後得到264g之白色粉末。藉由FD－MS分析，鑑定為中間體11。
200mL的三口燒瓶中加入4－溴聯苯基20.0g(東京化成社品)、t－丁氧基鈉8.64g(和光純藥公司製)、乙酸鈀84mg(和光純藥公司製)。再放入攪拌子，於燒瓶兩側設置橡膠蓋，於中央口設置迴流用水管，其上設置三通活栓與封入氬氣之氣球，系統內使用真空幫浦進行氣球的氬氣取代3次。
其次，將脫水甲苯120mL(廣和光公司製)、苯甲基胺4.08mL(東京化成公司製)、參－t－丁基膦338 μ L(Aldrich製、2.22mol/L甲苯溶液)藉由注射器通過橡膠隔板加入，室溫下攪拌5分鐘。其次，燒瓶設置於油浴中，一邊攪拌溶液一邊徐徐昇溫至120℃。7小時後，由油浴中取出燒瓶並使反應終止，氬氣環境下，放置12小時。將反應溶液移至分液漏斗，加入二氯甲烷600mL溶解沈澱物，以飽和食鹽水120mL洗淨後，有機層以無水碳酸鉀乾燥。餾去過濾除去碳酸鉀所得之有機層的溶劑，所得之殘渣中加入甲苯400mL、乙醇80mL，附上乾燥管並加熱80℃，完全溶解殘渣。其後，放置12小時，藉由冷卻至室溫而使其再結晶化。過濾析出之結晶，藉由60℃下真空乾燥而得到13.5g之N,N－二－(4－聯苯基)－苯甲基胺。於300mL之一口燒瓶中放入1.35g之N,N－二－(4－聯苯基)－苯甲基胺、鈀－活性碳135mg(廣和光公司製、鈀含有量10重量%)，氯仿100mL、乙醇20mL並溶解。其次，燒瓶中放入攪拌子後，將設有填充氫氣2L之氣球的三通活栓設置於燒瓶上，使用真空幫浦使燒瓶系統內的氫氣進行10次取代。減少的氫氣再重新填充，使氫氣容積再回至2L後，室溫下激烈攪拌溶液。30小時攪拌後，加入二氯甲烷100mL，過濾觸媒。其次，將所得之溶液移至分液漏斗中，以碳酸氫鈉飽和水溶液50mL洗淨後，分離出有機層，以無水碳酸鉀乾燥。濾過後，餾去溶劑，所得之殘渣中加入甲苯50mL後進行再結晶化。過濾析出之結晶，藉由50℃下進行真空乾燥得到0.99g之二－4－聯苯基胺。
氬氣流下，放入二－4－聯苯基胺10g、4,4’－二溴聯苯9.7g(東京化成公司製)、t－丁氧基鈉3g(廣和光公司製)、雙(三苯基膦)氯化鈀(II)0.5g(東京化成公司製)及二甲苯500mL，130℃下進行24小時反應。冷卻後加入水1000mL，混合物以矽藻石過濾，將濾液以甲苯萃取，再以無水硫酸鎂進行乾燥。將此減壓下濃縮，所得之粗生成物以管柱純化，以甲苯進行再結晶，將此過濾並乾燥後，得到9.1g之下述4’－溴－N,N－二聯苯基－4－胺－1,1’－聯苯基(中間體12)。
合成例10中，取代4－溴聯苯基使用1－溴萘8.0g以外，進行同様反應得到9.6g之白色粉末。藉由FD－MS分析，鑑定為中間體13。
合成例10中取代4－溴聯苯基使用16.1g之中間體3以外，進行同様反應後得到10.5g之白色粉末。藉由FD－MS分析，鑑定為中間體14。
下述合成實施例1~15中所合成的本發明芳香族胺衍生物之化合物H1~15、及比較例1所使用的比較化合物1的結構如下述。
氬氣流下，放入N,N’－二苯基聯苯胺3.4g、6.8g之中間體3、t－丁氧基鈉2.6g(廣和光公司製)、參(二亞芐基丙酮)二鈀(0)92mg(Aldrich製)、三－t－丁基膦42mg及脫水甲苯100mL，於80℃下進行8小時反應。
冷卻後加入水500mL，混合物以矽藻石過濾，將濾液以甲苯萃取，再以無水硫酸鎂進行乾燥。將此減壓下濃縮，所得之粗生成物以管柱純化，以甲苯進行再結晶，將此過濾並乾燥後，得到4.1g之淡黃色粉末。藉由FD－MS(The field－desorption mass spectra)之分析，鑑定為化合物H1。
氬氣流下，放入4,4’－二碘聯苯基4.1g、7.0g之中間體8、t－丁氧基鈉2.6g(廣和光公司製)、參(二亞芐基丙酮)二鈀(0)92mg(Aldrich製)、三－t－丁基膦42mg及脫水甲苯100mL，於80℃下進行8小時反應。
冷卻後加入水500mL，混合物以矽藻石過濾，將濾液以甲苯萃取，再以無水硫酸鎂進行乾燥。將此減壓下濃縮，所得之粗生成物以管柱純化，以甲苯進行再結晶，將此過濾並乾燥後，得到4.9g之淡黃色粉末。藉由FD－MS(The field－desorption mass spectra)之分析，鑑定為化合物H2。
合成實施例1中，取代N,N’－二苯基聯苯胺使用4.4g之中間體11以外，進行同様反應後得到5.2g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H3。
合成實施例1中取代中間體3使用8.4g之中間體4以外，進行同様反應後得到4.6g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H4。
合成實施例1中，取代中間體3使用6.8g之中間體5以外，進行同様反應後得到3.9g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H5。
氬氣流下，放入中間體10 8.2g、中間體12 11.0g、t－丁氧基鈉2.6g(廣和光公司製)、參(二亞芐基丙酮)二鈀(0)92mg(Aldrich製)、三－t－丁基膦42mg及脫水甲苯100mL，於80℃下進行8小時反應。
冷卻後加入水500mL，混合物以矽藻石過濾，將濾液以甲苯萃取，再以無水硫酸鎂進行乾燥。將此減壓下濃縮，所得之粗生成物以管柱純化，以甲苯進行再結晶，將此過濾並乾燥後，得到13.1g之淡黃色粉末。藉由FD－MS(The field－desorption mass spectra)之分析，鑑定為化合物H6。
合成實施例6中，取代中間體10使用6.5g之中間體6以外，進行同様反應後得到8.2g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H7。
合成實施例6中取代中間體10使用7.7g之中間體13以外，進行同様反應後得到10.2g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H8。
合成實施例6中取代中間體10使用10.3g之中間體14以外，進行同様反應後得到15.1g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H9。
合成實施例2中取代4,4’－二碘聯苯基使用二溴聯三苯基4.8g、取代中間體10使用7.0g之中間體6以外，進行同様反應後得到4.8g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H10。
合成實施例2中，取代4,4’－二碘聯苯基使用1,4－二碘苯3.3g以外，進行同様反應後得到4.1g之淡黃色粉末。藉由FD－MS之分析鑑定為化合物H11。
合成實施例1中取代N,N’－二苯基聯苯胺使用2.6g的中間體10，取代中間體3使用8.4g之中間體9以外，進行同様反應後得到5.9g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H12。
合成實施例1中，取代中間體3使用10.3g之中間體7以外，進行同様反應後得到6.5g之淡黃色粉末。藉由FD－MS分析，鑑定為化合物H13。
氬氣流下，300mL的三口燒瓶中放入4－二苯並呋喃硼酸6.3g、4,4’,4”－三溴三苯基胺4.8g、肆(三苯基膦)鈀(Pd(PPh3
)4
)104mg、2M之碳酸鈉(Na2
CO3
)溶液48mL、甲苯48mL後，於80℃反應8小時。反應液以甲苯/水進行萃取，以無水硫酸鈉乾燥。將此減壓下濃縮，所得之粗生成物藉由管柱純化得到3.9g之白黃色粉末。藉由FD－MS分析，鑑定為化合物H14。
合成實施例10中，取代4－二苯並呋喃硼酸使用4－二苯並噻吩硼酸6.8g、取代4,4’,4”一三溴三苯基胺使用N,N’－二苯基聯苯胺5.1g以外，進行同様反應後得到7.2g之淡黃色粉未。藉由FD－MS分析，鑑定為化合物H15。
25mm×75mm×1.1mm厚之附有ITO透明電極之玻璃基板(Geomatics公司製)於異丙基醇中進行超音波洗淨5分鐘後，進行30分鐘的UV臭氧洗淨。
將洗淨後附有透明電極線之玻璃基板裝於真空蒸鍍裝置之基板支架，首先形成透明電極線之側面上如覆蓋前述透明電極般，形成膜厚60nm之下述化合物H232。該H232膜作為電洞注入層使用。該H232膜上成膜作為電洞輸送材料之膜厚20nm的上述化合物H1層。該膜作為電洞輸送層而發揮其功能。且蒸鍍成膜為膜厚40nm之下述化合物EM1。同時作為發光分子，將具有下述苯乙烯基之胺化合物D1，蒸鍍成EM1與D1之重量比為40：2。該膜作為發光層使用。
該膜上形成膜厚10nm之下述Alq膜。將此作為電子注入層使用。此後，還原性摻雜物之Li(Li源：SAES GETTER公司製)與Alq進行二元蒸鍍，作為電子注入層(陰極)形成Alq：Li膜(膜厚10nm)。該Alq：Li膜上形成蒸鍍金屬Al之金屬陰極而形成有機EL元件。
又，對於所得之有機EL元件，測定發光效率，觀察發光色。發光效率為使用Minolta製CS1000測定其亮度，算出10mA/cm2
之發光效率。且，測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期之結果如表1所示。
實施例1中，作為電洞輸送材料取代化合物H1使用表1所記載的化合物以外，同様地製作出有機EL元件。
對於所得之有機EL元件，測定發光效率，觀察發光色，且，測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期之結果如表1所示。
實施例1中，作為電洞輸送材料取代化合物H1使用比較化合物1(比較例1)以外，同様地製作有機EL元件。比較化合物1於蒸鍍時結晶化，無法作成完整元件。
又，對於所得之有機EL元件，測定發光效率，觀察發光色，且，測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期之結果如表1所示。
實施例1中，取代具有苯乙烯基之胺化合物D1使用下述芳基胺化合物D2以外，同様地製作有機EL元件。Me為甲基。
對於所得之有機EL元件，測定發光效率時得到4.9cd/A，發光色為藍色。且測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期時為430小時。
實施例10中，作為電洞輸送材料取代化合物H1使用上述比較化合物1以外，同樣地製作有機EL元件。
對於所得之有機EL元件，測定發光效率時得到4.9cd/A，發光色為藍色。且測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期時為260小時。
實施例1中，取代H 232使用H1，取代H1使用比較化合物1以外，同様地製作有機EL元件。
對於所得之有機EL元件，測定發光效率時得到5.1cd/A，發光色為藍色。且測定初期亮度5000cd/m2
、室溫、DC定電流驅動下的發光半衰期時為360小時。
如上述詳細說明，本發明的芳香族胺衍生物為分子難以結晶化，將此含於有機薄膜層時，可提高製造有機EL元件時的產率，實現壽命較長的有機EL元件。
Claims (16)
- 一種如下述一般式(1)所示之芳香族胺衍生物，
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(1)中，Ar1 與Ar2 為該一般式(3)所示。
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(1)中，Ar1 與Ar3 為該一般式(3)所示。
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(1)中，僅Ar1 為該一般式(3)所示。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其中該一般式(1)中b為2。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其中該一般式(3)中i為1。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其中該一般式(3)中X為氧原子。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其中該一般式(1)中Ar2 為下述一般式(4)所示；
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其中該一般式(1)中Ar2 及Ar4 各獨立為該一般式(4)所示。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其為有機電致發光元件用材料。
- 如申請專利範圍第1項至第4項中任一項之芳香族胺衍生物，其為有機電致發光元件用電洞注入材料或電洞輸送材料。
- 一種如下述一般式(5)所示之芳香族胺衍生物，
- 一種有機電致發光元件，其為陰極與陽極間挾持 至少含有發光層的一層或複數層所成之有機薄膜層的有機電致發光元件，其特徵為該有機薄膜層的至少1層為含有如申請專利範圍第1項至第9項及第12項中任一項之芳香族胺衍生物作為單獨或混合物的成分者。
- 如申請專利範圍第13項之有機電致發光元件，其中該有機薄膜層具有電洞注入層或電洞輸送層，且如申請專利範圍第1項至第9項及第12項中任一項之芳香族胺含於該電洞注入層或電洞輸送層中。
- 如申請專利範圍第13項之有機電致發光元件，其中該發光層中含有苯乙烯胺及/或芳胺。
- 如申請專利範圍第13項至第15項中任一項之有機電致發光元件，其特徵，其為藍色系發光。
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- 2007-03-28 KR KR1020087025937A patent/KR101453109B1/ko active IP Right Grant
- 2007-03-28 EP EP13171994.0A patent/EP2639231B1/en active Active
- 2007-03-28 EP EP07740034.9A patent/EP2011790B1/en active Active
- 2007-03-28 KR KR1020147018087A patent/KR101551591B1/ko active IP Right Grant
- 2007-03-28 CN CN200780014872.1A patent/CN101432272B/zh active Active
- 2007-03-28 JP JP2008513112A patent/JP5186365B2/ja active Active
- 2007-04-04 US US11/696,514 patent/US8129038B2/en active Active
- 2007-04-12 TW TW096112931A patent/TWI418547B/zh active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2011790A1 (en) | 2009-01-07 |
| CN101432272B (zh) | 2013-02-27 |
| EP2011790B1 (en) | 2016-06-29 |
| WO2007125714A1 (ja) | 2007-11-08 |
| KR20140091074A (ko) | 2014-07-18 |
| JP5186365B2 (ja) | 2013-04-17 |
| US20070278938A1 (en) | 2007-12-06 |
| JPWO2007125714A1 (ja) | 2009-09-10 |
| KR101453109B1 (ko) | 2014-10-27 |
| KR101551591B1 (ko) | 2015-09-08 |
| TW200812994A (en) | 2008-03-16 |
| EP2639231B1 (en) | 2019-02-06 |
| EP2011790A4 (en) | 2010-08-25 |
| US8129038B2 (en) | 2012-03-06 |
| CN101432272A (zh) | 2009-05-13 |
| EP2639231A1 (en) | 2013-09-18 |
| KR20080112325A (ko) | 2008-12-24 |
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