TWI488848B - Aromatic amine derivatives and organic electroluminescent elements using the same - Google Patents
Aromatic amine derivatives and organic electroluminescent elements using the same Download PDFInfo
- Publication number
- TWI488848B TWI488848B TW096131244A TW96131244A TWI488848B TW I488848 B TWI488848 B TW I488848B TW 096131244 A TW096131244 A TW 096131244A TW 96131244 A TW96131244 A TW 96131244A TW I488848 B TWI488848 B TW I488848B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- general formula
- aromatic amine
- terphenyl
- amine derivative
- Prior art date
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- 150000004982 aromatic amines Chemical class 0.000 title claims description 95
- -1 1-indenyl Chemical group 0.000 claims description 234
- 125000003118 aryl group Chemical group 0.000 claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- 239000000463 material Substances 0.000 claims description 59
- 238000002347 injection Methods 0.000 claims description 56
- 239000007924 injection Substances 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 239000010408 film Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000004429 atom Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 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 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 238000007740 vapor deposition Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 18
- 239000010409 thin film Substances 0.000 claims description 18
- 125000006267 biphenyl group Chemical group 0.000 claims description 15
- 238000005401 electroluminescence Methods 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 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 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- LHEOFIBQZSRTNC-UHFFFAOYSA-N phenanthrene-3-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3C=CC2=C1 LHEOFIBQZSRTNC-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 178
- 150000001875 compounds Chemical class 0.000 description 111
- 230000015572 biosynthetic process Effects 0.000 description 99
- 239000000543 intermediate Substances 0.000 description 95
- 238000003786 synthesis reaction Methods 0.000 description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 53
- 238000000034 method Methods 0.000 description 37
- 239000000843 powder Substances 0.000 description 37
- 238000000434 field desorption mass spectrometry Methods 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 33
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- 239000000126 substance Substances 0.000 description 32
- 239000013078 crystal Substances 0.000 description 31
- 229910052799 carbon Inorganic materials 0.000 description 28
- 238000001914 filtration Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 26
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 239000011734 sodium Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 12
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 229930192474 thiophene Natural products 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- 150000001454 anthracenes Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 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 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000005684 electric field Effects 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001771 vacuum deposition Methods 0.000 description 7
- 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 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 229960003540 oxyquinoline Drugs 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 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 6
- 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 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001721 carbon Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- 150000003613 toluenes Chemical class 0.000 description 5
- KCHQXPGUJBVNTN-UHFFFAOYSA-N 4,4-diphenylbut-3-en-2-one Chemical compound C=1C=CC=CC=1C(=CC(=O)C)C1=CC=CC=C1 KCHQXPGUJBVNTN-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 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 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000008425 anthrones Chemical class 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
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- OAYONPVQZPIHBU-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=CC2=CC3=CC=CC=C3C=C21 OAYONPVQZPIHBU-UHFFFAOYSA-N 0.000 description 1
- ANVUHDFHRCDPKV-UHFFFAOYSA-N anthracene fluoranthene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 ANVUHDFHRCDPKV-UHFFFAOYSA-N 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 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
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 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
- 230000004888 barrier function Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 239000011230 binding agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000000460 chlorine 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
- 238000004140 cleaning Methods 0.000 description 1
- 239000004020 conductor Substances 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
- 239000013058 crude material Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 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
- 125000006612 decyloxy group Chemical group 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- JJVJPJWQXDQCEI-UHFFFAOYSA-N ethenylhydrazine Chemical compound NNC=C JJVJPJWQXDQCEI-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 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
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 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
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 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
- 125000002883 imidazolyl group Chemical group 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
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000010977 jade Substances 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
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- 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
- 238000005259 measurement Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 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
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 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
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 239000002773 nucleotide Substances 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
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002923 oximes 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
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen 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
- 229960005489 paracetamol Drugs 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 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
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004060 quinone imines Chemical group 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 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
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Inorganic materials [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 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
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 238000012546 transfer Methods 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
- 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
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- 150000003679 valine derivatives Chemical class 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 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
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- 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
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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Description
本發明係有關芳香族胺衍生物及使用其之有機電激發光(EL)元件，特別是關於將具有特定取代基的芳香族胺衍生物用於電洞輸送材料，使驅動電壓降低，同時抑制分子之結晶化，提高製造有機EL元件時之良率，改善有機EL元件的壽命的芳香族胺衍生物。
有機EL元件係利用藉由外加電場，以由陽極注入之電洞與由陰極注入電子之再結合能量，使螢光性物質產生發光之原理的自行發光元件。自伊斯曼柯達公司之C.W.Tang等發表藉由層合型元件之低電壓驅動有機EL元件之報告(C.W.Tang，S.A.Vanslyke，應用物理論壇(Applied Physics Letters)，51卷，913頁，1987年等)以來，有關以有機材料為構成材料之有機EL元件之研究正盛行。Tang等人將三(8－喹啉酚)鋁用於發光層，將三苯基二胺衍生物用於電洞輸送層。層合結構之優點，例如有提高電洞注入發光層之注入效率；提高捕捉由陰極注入的電子，以再結合產生之激發子的生成效率；封閉在發光層內生成的激發子等。如上述例中，有機EL元件之元件構造例如有以電洞輸送(注入)層、電子輸送發光層之二層型，或電洞輸送(注入)層、發光層、電子輸送(注入)層之三層型等為人所熟知。這種層合型構造元件為了提高被注入之電洞與電子之再結合效率，因此在元件構造或形成方法方面下工夫。
通常，在高溫環境下驅動或保管有機EL元件時，會產生發光色變化、發光效率降低、驅動電壓上升、發光壽命縮短等不良影響。為了防止這些問題，必須提高電洞輸送材料之玻璃轉化溫度(Tg)。因此，電洞輸送材料之分子內必須具有大量之芳香族基(例如專利文獻1之芳香族二胺衍生物、專利文獻2之芳香族縮合環二胺衍生物)，通常可使用具有8~12個苯環的結構。
但是分子內具有大量芳香族基時，使用這些電洞輸送材料形成薄膜，製作有機EL元件時，容易產生結晶化，堵塞蒸鍍用之乾堝的出口，或因結晶化造成薄膜缺陷，導致有機EL元件之良率降低等的問題。又，分子內具有許多芳香族基之化合物，一般玻璃轉化溫度(Tg)較高，但是昇華溫度高，產生蒸鍍時之分解或蒸鍍不均勻等現象，因此有壽命較短的問題。
另外，有揭示非對稱之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的芳香族胺衍生物，但是無具體的實施例，也完全未記載非對稱化合物的特徴。又，專利文獻4中雖記載具有菲之非對稱之芳香族胺衍生物的實施例，但是與對稱化合物同樣處理，且完全未記載非對稱化合物的特徴。又，縱使非對稱化合物需要特殊的合成法，但是此等專利中並未明確記載非對稱化合物的製造方法。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方法，但是未記載非對稱化合物的特徴。專利文獻6中雖記載玻璃轉化溫度較高之熱安定的非對稱化合物，但僅列舉具有咔唑的化合物。
又，具有噻吩之化合物的報告，例如有專利文獻7~8，但是這些為於二胺化合物之中心骨架中具有噻吩的化合物。專利文獻7係噻吩直接與胺鍵結。二胺化合物之末端具有噻吩之化合物的報告有專利文獻9~10，但這些為噻吩直接與胺鍵結。噻吩直接與胺鍵結時，胺之電子狀態大幅變動，因此無法展現充分的性能。專利文獻11雖記載噻吩介於芳基，與胺鍵結的化合物。但是這些之化合物係2位或5位含有無取代之噻吩的結構。噻吩之2位或5位係因反應性高，電性不安定，因此分子內含有這些時，元件評價上，電壓上升，故不佳。多聚物胺例如有專利文獻12，但是僅有具體例，完全未記載噻吩介於芳基，與氮鍵結之胺化合物的特徵。高分子例如有專利文獻13~22，但是無法蒸鍍。聚合所需之極性基會降低壽命等之元件的性能，故不理想。
如上述，具有噻吩結構之化合物，其移動度較高為一般所知，但是僅與胺結構組合，仍無法展現充分的性能。因此，強烈期望開發具有更優異性能的有機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]WO2004－058740[專利文獻8]特開平4－304466號公報[專利文獻9]WO2001－053286[專利文獻10]特開平7－287408號公報[專利文獻11]特開2003－267972號公報[專利文獻12]特開2004－155705號公報[專利文獻13]特開2005－042004號公報[專利文獻14]特開2005－259441號公報[專利文獻15]特開2005－259442號公報[專利文獻16]特開2005－235645號公報[專利文獻17]特開2005－235646號公報[專利文獻18]特開2005－082655號公報[專利文獻19]特開2004－288531號公報[專利文獻20]特開2004－199935號公報[專利文獻21]特開2004－111134號公報[專利文獻22]特開2002－313574號公報
本發明係為了解決上述課題而完成者，本發明之目的係使驅動電壓降低，同時分子不易結晶化，提高製造有機EL元件時之良率，提供壽命長的有機EL元件及實現此目的之芳香族胺衍生物。
本發明人等為達成前述目的，精心研究結果，發現將下述一般式(1)所示具有特定取代基的新穎芳香族胺衍生物作為有機EL元件用材料使用，特別是作為電洞輸送材料使用時，可解決上述課題，而完成本發明。
又，發現一般式(2)所示之具有噻吩結構之芳基所取代的胺基適合作為具有特定取代基的胺單位。此胺單位因具有極性基，因此可與電極相互作用，電荷注入變得容易，及具有噻吩結構，移動度高，具有驅動電壓降低的效果，同時具有立體障礙性，因此分子間的相互作用較小，可抑制結晶化，具有提高製造有機EL元件之良率，延長製得之有機EL元件的壽命的效果，特別是與藍色發光元件組合，可得到顯著低電壓及長壽命的效果。在大分子量之化合物中，具有非對稱結構之化合物可降低蒸鍍溫度，因此抑制蒸鍍時之分解，可延長壽命。
換言之，本發明係提供下述一般式(1)表示之芳香族胺胺衍生物。
本發明係提供以下述一般式(4)~(6)中任一表示之芳香族胺衍生物。
a係1~3的整數。
L2
係取代或無取代之核原子數6~50之伸芳基。但是無a=2，且2個R1
形成環，成為苯並噻吩基的情形]。
一般式(4)~(6)中，Ar5
~Ar21
之中，非一般式(7)者係分別獨立為取代或無取代之核原子數6~50之芳基。但是Ar5
~Ar21
之取代基係核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子或氰基。
但是一般式(5)中，Ar11
與Ar14
無同時為噻吩基芳基的情形]。
本發明係提供一種有機EL元件，其係於陰極與陽極間挾持至少含有發光層之一層或多層所構成之有機薄膜層的有機EL元件，其特徵係該有機薄膜層之至少一層為含有該芳香族胺衍生物作為單獨或混合物的成分。
本發明之芳香族胺衍生物及使用其之有機EL元件係使驅動電壓降低，同時分子不易結晶化，提高製造有機EL元件時之良率，壽命長。
本發明之芳香族胺衍生物係下述一般式(1)表示者。
式中，L1
係取代或無取代之核原子數6~50之伸芳基。Ar1
~Ar4
之中至少1個係以下述一般式(2)表示。
一般式(2)中，R1
係取代或無取代之核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子或氰基。a係1~3的整數。L2
係取代或無取代之核原子數6~50之伸芳基。
一般式(1)中，Ar1
~Ar4
之中非一般式(2)者係分別獨立為取代或無取代之核原子數6~50之芳基。但是Ar1
~Ar4
之取代基係核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子或氰基。但是無a＝2，且2個R1
形成環，成為苯並噻吩基的情形。
一般式(1)表示之本發明之芳香族胺衍生物係該一般式(2)為下述一般式(3)表示者較佳。
一般式(3)中，R1
係取代或無取代之核原子數6~50之芳基或碳數1~50之支鏈或直鏈之烷基。L2
係取代或無取代之核原子數6~50之伸芳基。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
為該一般式(2)表示者較佳。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
與Ar2
為該一般式(2)表示者較佳。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
與Ar3
為該一般式(2)表示者較佳。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
~Ar4
之中3個以上係互相不同，且非對稱者較佳。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
~Ar4
之中3個相同，且非對稱者較佳。
本發明之芳香族胺衍生物係該一般式(1)中，Ar1
~Ar4
之中非一般式(2)表示者分別獨立為苯基、聯苯基、三聯苯基或芴基較佳。
本發明之芳香族胺衍生物係該一般式(1)中，L1
為伸聯苯基、伸三聯苯基或伸芴基較佳。
本發明之芳香族胺衍生物係該一般式(2)中，L2
為伸苯基、伸聯苯基或伸芴基較佳。
本發明之芳香族胺衍生物係該一般式(2)中，R1
為苯基、萘基或菲基較佳。
本發明之芳香族胺衍生物係該一般式(1)中,Ar1
~Ar4
之中非一般式(2)表示者分別獨立為苯基、聯苯基、三聯苯基或芴基，L1
為伸聯苯基、伸三聯苯基或伸芴基，該一般式(2)中，L2
為伸苯基、伸聯苯基或伸芴基較佳。
本發明之芳香族胺衍生物係以下述一般式(4)~(6)中任一表示。
一般式(4)~(6)中，L5
~L12
係取代或無取代之核原子數6~50之伸芳基。Ar5
~Ar9
之中至少1個為下述一般式(7)表示。Ar10
~Ar15
之中至少1個為下述一般式(7)表示。Ar16
~Ar21
之中至少1個為下述一般式(7)表示。
一般式(7)中，R1
係取代或無取代之核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子或氰基。a係1~3的整數。L2
係取代或無取代之核原子數6~50之伸芳基。但是無a=2，且2個R1
形成環，成為苯並噻吩基的情形。
一般式(4)~(6)中，Ar5
~Ar21
之中，非一般式(7)表示者係分別獨立為取代或無取代之核原子數6~50之芳基。但是Ar5
~Ar21
之取代基係核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子或氰基。
但是一般式(5)中，Ar11
與Ar14
無同時為噻吩基芳基的情形。
一般式(4)~(6)表示之本發明之芳香族胺衍生物係該一般式(7)為下述一般式(8)表示者較佳。
一般式(8)中，R1
係取代或無取代之核原子數6~50之芳基或碳數1~50之支鏈或直鏈之烷基。L2
係取代或無取代之核原子數6~50之伸芳基。
本發明之芳香族胺衍生物，其中該一般式(4)中，Ar5
~Ar9
之中至少1個係以一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(4)中，Ar5
為該一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(4)中，Ar6
與Ar8
為該一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(5)中，Ar10
~Ar15
之中至少1個係以一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(5)中，Ar10
與Ar15
為該一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(5)中，Ar11
與Ar13
為該一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(6)中，Ar16
~Ar21
之中至少1個係以一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(6)中，Ar16
與Ar18
與Ar20
為該一般式(7)表示者較佳。
本發明之芳香族胺衍生物，其中該一般式(4)~(6)中，Ar5
~Ar21
之中，非一般式(7)表示者為苯基、聯苯基、三聯苯基或芴基較佳。
本發明之芳香族胺衍生物，其中該一般式(4)~(6)中，L5
~L12
係分別獨立為伸苯基、伸聯苯基、伸三聯苯基或伸芴基較佳。
本發明之芳香族胺衍生物，其中該一般式(7)中，L2
為伸苯基、伸聯苯基或伸芴基較佳。
本發明之芳香族胺衍生物，其中該一般式(7)中，R1
為苯基、萘基或菲基較佳。
本發明之芳香族胺衍生物，其中該一般式(4)~(6)中，Ar5
~Ar21
之中，非一般式(7)表示者為苯基、聯苯基、三聯苯基或芴基，L5
~L12
為伸苯基、伸聯苯基、伸三聯苯基或伸芴基，一般式(7)中，L2
為伸苯基、伸聯苯基或伸芴基較佳。
一般式(1)及(4)~(6)之Ar1
~Ar21
及一般式(2)、(3)、(7)及(8)之R1
之取代或無取代之核原子數6~50之芳基，例如有苯基、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－丁省基、2－丁省基、9－丁省基、1－芘基、2－芘基、4－芘基、2－聯苯基、3－聯苯基、4－聯苯基、對三聯苯－4－基、對三聯苯－3－基、對三聯苯－2－基、間三聯苯－4－基、間三聯苯－3－基、間三聯苯－2－基、鄰甲苯基、間甲苯基、對甲苯基、對第三丁基苯基、對－(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”－第三丁基對三聯苯－4－基、熒蒽基、芴基等。
其中較佳為苯基、萘基、聯苯基、三聯苯基、芴基。
噻吩化合物係2位與5位之反應性高，因此保護此取代位置較佳。公知文獻有Macromol.Rapid Commun.,2001,22,266－270，電性不安定下進行聚合。取代基較佳為烷基或芳基，但是從化合物之安定性的觀點，較佳為芳基，更佳為無取代之芳基。
一般式(1)及(4)~(6)之L1
及L5
~L12
、一般式(2)、(3)、(7)及(8)之L2
之取代或無取代之核原子數6~50之伸芳基，例如有使前述芳基之例成為2價基者。
一般式(2)、(3)、(7)及(8)之R1
之取代或無取代之碳數1~50之烷基，例如有甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基、正庚基、正辛基、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、2,3－二氯第三丁基、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、2,3－二溴基第三丁基、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、2,3－二碘第三丁基、1,2,3－三碘丙基、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、2,3－二氰基第三丁基、1,2,3－三氰丙基、三氟甲基、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－降冰片基、2－降冰片基等。較佳為烴所構成之飽和之鏈狀、支鏈狀或環狀之烷基，具體而言例如有甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基、正庚基、正辛基、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－降冰片基、2－降冰片基等。
一般式(2)、(3)、(7)及(8)之R1
之鹵原子，例如有氟原子、氯原子、溴原子、碘原子等。
Ar1
~Ar21
之取代基之核原子數6~50之芳基、碳數1~50之支鏈或直鏈之烷基、鹵原子及氰基之例係與前述相同。
一般式(2)及(7)中，a係1~3的整數。a為2以上時，多個R1
互相結合可形成飽和或不飽和之可被取代之5員環或6員環的環状構造。但是不包括芳香族環。
此可形成之5員環或6員環之環狀結構，例如有環戊烷、環己烷、金剛烷、降冰片烷等之碳數4~12之環鏈烷、環戊烯、環己烯等之碳數4~12之環鏈烯、環戊二烯、環己二烯等之碳數6~12之環烷二烯等。
本發明之一般式(1)及(4)~(6)表示之芳香族胺衍生物之具體例如下述，但是不受此例示化合物所限定。
本發明之芳香族胺衍生物係有機電致發光元件用材料為佳。
本發明之芳香族胺衍生物係蒸鍍用有機電致發光元件用材料為佳。
本發明之芳香族胺衍生物係有機電致發光元件用電洞輸送材料為佳。
本發明係提供一種有機EL元件，其係於陰極與陽極間挾持至少含有發光層之一層或多層所構成之有機薄膜層的有機EL元件，其中該有機薄膜層之至少一層為含有前述芳香族胺衍生物作為單獨或混合物的成分。
本發明之有機EL元件較佳為該有機薄膜層具有電洞輸送層，該電洞輸送層中含有該芳香族胺衍生物。
本發明之有機EL元件較佳為該有機薄膜層具有多層之電洞輸送層，未直接與發光層接觸之層中含有該芳香族胺衍生物。
本發明之有機EL元件較佳為該有機薄膜層具有電洞注入層，該電洞注入層中含有該芳香族胺衍生物。前述電洞注入層中含有該芳香族胺衍生物作為主成分較佳。
螢光性摻雜劑係配合要求之發光色可選自例如胺系化合物、芳香族化合物、三(8－喹啉酚)鋁錯合物等之螯合錯合物、香豆素衍生物、四苯基丁二烯衍生物、雙苯乙烯基伸芳基衍生物、噁二唑衍生物等的化合物，特別理想為芳基胺化合物、芳基二胺化合物，其中更佳為苯乙烯胺化合物、苯乙烯二胺化合物、芳香族胺化合物、芳香族二胺化合物。縮合多環芳香族化合物(不含胺化合物)更佳。這些螢光性摻雜劑可單獨或組合多種以上使用。
這種苯乙烯胺化合物及苯乙烯二胺化合物較佳為下述一般式(A)表示者。
其中，碳數6~20之芳香族烴基，例如有苯基、萘基、蒽基、菲基、三聯苯基等。
芳香族胺化合物及芳香族二胺化合物較佳為下述一般式(B)表示者。
核碳數5~40之芳基，例如有苯基、萘基、蒽基、菲基、芘基、暈苯基、聯苯基、三聯苯基、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、二苯乙烯基、苝基、基、苉基、三苯基、玉紅省基、苯並蒽基、苯基蒽基、雙蒽基或下述一般式(C)、(D)表示之芳基等，其中較佳為萘基、蒽基、基、芘基或下述一般式(D)表示之芳基。
前述芳基所取代之較佳之取代基，例如有碳數1~6之烷基(乙基、甲基、異丙基、正丙基、第二丁基、第三丁基、戊基、己基、環戊基、環己基等)、碳數1~6之烷氧基(乙氧基、甲氧基、異丙氧基、正丙氧基、第二丁氧基、第三丁氧基、戊氧基、己氧基、環戊氧基、環己氧基等)、核原子數5~40之芳基、核碳數5~40芳基所取代之胺基、具有核碳數5~40之芳基之酯基、具有碳數1~6之烷基之酯基、氰基、硝基、鹵原子等。
縮合多環芳香族化合物(不含胺化合物)，較佳為例如有萘、蒽、菲、芘、暈苯、聯苯、三聯苯、吡咯、呋喃、噻吩、苯並噻吩、噁二唑、吲哚、咔唑、吡啶、苯並喹啉、熒蒽、苯並熒蒽、苊並熒蒽、二苯乙烯、苝、、苉、三苯、玉紅省、苯並蒽等之縮合多環芳香族化合物及其衍生物。
本發明之有機EL元件係構成前述電洞注入層及/或電洞輸送層之各層中，與陽極接觸的層為含有受體材料的層較佳。
受體係易還原性之有機化合物。
化合物之還原容易度可以還原電位測定。本發明係飽和甘汞(SCE)電極作為參考電極之還原電位中，－0.8V以上較佳，特佳為具有比四氰基對醌二甲烷(TCNQ)之還原電位(約0V)更高之值的化合物。
易還原性之有機化合物較佳為具有電子吸引性之取代基的有機化合物。具體而言例如有醌型衍生物、吡嗪衍生物、芳基硼烷衍生物、亞胺衍生物等。醌型衍生物包括對醌二甲烷衍生物、二氧化噻喃衍生物、二氧化噻呫噸酮衍生物及喹啉衍生物等。
本發明之芳香族胺衍生物，特別理想為用於藍色系發光之有機EL元件。
以下說明本發明之有機EL元件的元件構成。
(1)有機EL元件之構成本發明之有機EL元件之代表性的元件構成，例如(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/含受體之層/電洞注入層/電洞輸送層/發光層/電子輸送層/電子注入層/陰極(10)陽極/絕緣層/發光層/絕緣層/陰極(11)陽極/無機半導體層/絕緣層/發光層/絕緣層/陰極(12)陽極/有機半導體層/絕緣層/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/絕緣層/陰極(14)陽極/絕緣層/電洞注入層/電洞輸送層/發光層/電子注入層/陰極等的構造。
其中通常使用(8)之構成較佳，但不受此限定。
本發明之芳香族胺衍生物可用於有機EL元件之任一有機薄膜層，可用於發光帶域或電洞輸送帶域中，藉由用於電洞輸送帶域，特別是用於電洞注入層，分子不易結晶化，可提高製造有機EL元件時的良率。
有機薄膜層含有本發明之芳香族胺衍生物的量，較佳為30~100莫耳%。
(2)透光性基板本發明之有機EL元件係製作於透光性之基板上。此透光性基板係支撐有機EL元件的基板，較佳為400~700nm之可見光範圍之光穿透率為50%以上，且平滑之基板。
具體而言，例如有玻璃板、聚合物板等。玻璃板特別是鈉鈣玻璃、含鋇．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。另外，聚合物板例如有聚碳酸酯、丙烯酸、聚對苯二甲酸乙二酯、聚硫醚樹脂、聚等。
(3)陽極本發明之有機EL元件之陽極係具有將電洞注入電洞輸送層或發光層的功能者，具有4.5eV以上之功函數者效果較佳。本發明用之陽極材料之具體例為氧化銦錫合金(ITO)、氧化銦鋅合金(IZO)、氧化錫(NESA)、金、銀、鉑、銅等。
這些電極物質可以蒸鍍法或濺鍍法等形成薄膜來製作陽極。
如上述由陽極取出發光層之發光時，陽極對於發光之透過率為大於10%較佳。又，陽極之薄片電阻為數百Ω/□以下較佳。陽極之膜厚係因材料而異，但是通常為10nm~1μm，較佳為10~200nm的範圍。
(4)發光層有機EL元件之發光層兼具下述(1)~(3)的功能。
(1)注入功能；外加電場時，可由陽極或電洞注入層注入電洞，且可由陰極或電子注入層注入電子的功能。
(2)輸送功能；以電場的力量移動注入之電荷(電子與電洞)的功能。
(3)發光功能；提供電子與電洞之再結合的場所，以此提供發光的功能。
但是電洞注入之容易度與電子注入之容易度可不相同，以電洞與電子之移動度表示之輸送能可具有大小，但是移動其中一方的電荷較佳。
形成此發光層的方法，可使用例如蒸鍍法、旋轉塗佈法、LB(Langmuir Brozet)法等公知方法。發光層特別是以分子堆積膜為佳。此處所謂分子堆積膜係指由氣相狀態之材料化合物所沈澱形成的薄膜或由溶液狀態或液相狀態之材料化合物固化所形成的膜，通常此分子堆積膜係與LB法所形成之薄膜(分子累積膜)可藉由凝集構造、高次構造之不同，或因該構造所產生之功能性不同來區別。
又，如日本特開昭57－51781號所揭示，將樹脂等之粘結劑與材料化合物溶解於溶劑中形成溶液後，使用旋轉塗佈法等將此溶液製成薄膜，也可形成發光層。
本發明之化合物用於發光層時，在不影響本發明之目的之範圍內，視需要在發光層內可含有本發明之芳香族胺衍生物所構成之發光材料以外之其他公知的發光材料，而且可將含有其他公知的發光材料的發光層層合於含有本發明之芳香族胺衍生物所構成之發光材料的發光層上。
與本發明之化合物組合使用之發光材料，主要是有機化合物，可使用的摻雜劑材料，例如有蒽、萘、菲、芘、丁省、暈苯、、熒光素、苝、酞苝、萘苝、苝酮、酞苝酮、萘苝酮、二苯基丁二烯、四苯基丁二烯、香豆素、噁二唑、醛連氮、雙苯并噁唑啉、聯苯乙烯、吡嗪、環戊二烯、喹啉金屬錯合物、胺基喹啉金屬錯合物、苯并喹啉金屬錯合物、亞胺、二苯基乙烯、乙烯蒽、二胺基咔唑、吡喃、噻喃、聚次甲基、部花青、咪唑螯合化羥基喹啉化合物、喹吖啶酮、紅螢烯及螢光色素等，但不限於此。
可與本發明之化合物組合使用的主(host)材料，較佳為下述(i)~(xi)表示之化合物。
下述一般式(i)表示之非對稱蒽。
下述一般式(ii)所示之非對稱單蒽衍生物。
下述一般式(iii)所示之非對稱芘衍生物。
一般式(iv)所示之非對稱蒽衍生物。
下述一般式(v)所示之蒽衍生物。
下述一般式(vi)所示之蒽衍生物。
下述一般式(vii)所示之螺芴衍生物。
下述一般式(viii)所示之含縮合環化合物。
下述一般式(ix)所示之芴化合物。
下述一般式(x)所示具有蒽中心骨架之化合物。
具有前述一般式(x)中，A1
與A2
不同之基之下述一般式(xi)表示之結構的化合物。
以上之主材料中，較佳為蒽衍生物，更佳為單蒽衍生物，特佳為非對稱蒽衍生物。
適合於含咔唑環之化合物所構成之磷光發光的主體(host)材料係由其激態狀態向磷光發光性化合物產生能量移動的結果，具有可使磷光發光性化合物發光之功能的化合物。主體化合物只要是可將激發子能量移動至磷光發光性化合物的化合物時，則無特別限制，可依據目適當選擇。除咔唑環外，也可具有任意的雜環等。
這種主體化合物之具體例有咔唑衍生物、三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳烷衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳胺衍生物、胺基取代苯基乙烯酮衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、矽胺烷衍生物、芳香族第三胺化合物、苯乙烯基胺化合物、芳香族亞甲基系化合物、卟啉系化合物、蒽醌並二甲烷衍生物、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、亞芴基甲烷衍生物、二苯乙烯基吡嗪衍生物、萘苝等雜環四羧酸酸酐；酞菁衍生物、8－喹啉酚衍生物之金屬錯合物或金屬酞菁、以苯並噁唑或苯並噻唑為配位基之金屬錯合物所代表之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、聚噻吩等之導電性高分子寡聚物、聚噻吩衍生物、聚伸苯基衍生物、聚伸苯基乙烯衍生物、聚芴衍生物等高分子化合物等。主體化合物可單獨使用或併用2種以上。
具體例有如下述的化合物。
磷光發光性之摻雜劑係可由三重態激發子發光的化合物。只要可由三重態激發子發光時，並無特別限定，但是以含有選自Ir、Ru、Pd、Pt、Os及Re所成群之至少一種金屬的金屬錯合物較佳，卟啉金屬錯合物或鄰位金屬化金屬錯合物為佳。卟啉金屬錯合物較佳為卟啉鉑錯合物。磷光發光性化合物可單獨或併用2種以上。
形成鄰位金屬化金屬錯合物之配位基有許多種類，較佳之配位基例如有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。這些衍生物必要時可具有取代基。特別是導入氟化物、三氟甲基者適合作為藍色系摻雜劑。可具有作為補助配位基之乙醯基丙酮合基、苦味酸等上述配位基以外的配位基。
磷光發光性之摻雜劑在發光層中之含量並無特別限制，可依目的適當選擇，例如0.1~70質量%，較佳為1~30質量%。磷光發光性化合物之含量若未達0.1質量%時，發光微弱無法充分發揮其之含有效果，若超過70質量%時，所謂的濃度消光的現象顯著，元件性能降低。
發光層在必要時可含有電洞輸送材、電子輸送、聚合物黏合劑。
發光層之膜厚較佳為5~50nm，更佳為7~50nm，最佳為10~50nm。若未達5nm時難以形成發光層，有時色度調整可能困難，若超過50nm時，驅動電壓可能上昇。
(5)電洞注入．輸送層(電洞輸送帶域)電洞注入．輸送層係幫助電洞注入發光層，輸送至發光區域的層，電洞移動度大，電離勢低通常為5.6eV以下。這種電洞注入．輸送層係以更低電場強度，將電洞輸送至發光層的材料為佳，電洞之移動度，例如外加104
~106
V/cm的電場時，至少10－4
cm2
/V．秒為佳。
本發明之芳香族胺衍生物用於電洞輸送帶域時，本發明之芳香族胺衍生物可單獨形成電洞注入、輸送層，也可與其他材料混合使用。
與本發明之芳香族胺衍生物混合形成電洞注入．輸送層的材料只要是具有前述較佳特性者即無特別限制，可選擇使用過去慣用於光傳導材料中作為電洞之電荷輸送材料者、或使用於有機EL元件之電洞注入．輸送層之公知者中任意者。本發明中，具有電洞輸送能，可用於電洞輸送帶域的材料稱為電洞輸送材料。
具體例有三唑衍生物(參照美國專利3,112,197號說明書等)、噁二唑衍生物(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、日本特開昭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)、吡唑啉衍生物及吡唑啉酮衍生物(參照美國專利第3,180,729號說明書、同第4,278,746號說明書、日本特開昭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)、苯二胺衍生物(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、日本特開昭54－119925號公報等)、芳胺衍生物(參照美國專利第3,567,450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、日本特開昭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)、胺基取代苯基乙烯酮衍生物(參照美國專利第3,526,501號說明書等)、噁唑衍生物(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(參照日本特開昭56－46234號公報等)、芴酮衍生物(參照日本特開昭54－110837號公報等)、腙衍生物(參照美國專利第3,717,462號說明書、日本特開昭54－59143號公報、同55－52063號公報、同55－52064號公報、同55－46760號公報、同57－11350號公報、同57－148749號公報、日本特開平2－311591號公報等)、二苯乙烯衍生物(參照日本特開昭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)、矽胺烷衍生物(美國專利第4,950,950號說明書)、聚矽烷系(日本特開平2－204996號公報)、苯胺系共聚物(日本特開平2－282263號公報)等。
電洞注入．輸送層之材料可使用上述者，但是較佳為使用卟啉化合物(日本特開昭63－2956965號公報等所揭示者)、芳香族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、日本特開昭53－27033號公報、同54－58445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)，特別使用芳香族三級胺化合物為佳。
又，美國專利第5,061,569號所記載之分子內具有2個縮合芳香族環，例如4,4’－雙(N－(1－萘基)－N－苯基胺基)聯苯基(以下簡稱為NPD)、日本特開平4－308688號公報所記載之三苯基胺單位連接成3個星芒型之4,4’,4”－三(N－(3－甲基苯基)－N－苯基胺基)三苯胺(以下簡稱為MTDATA)等。
其他也可使用專利3571977號所揭示之下述式)表示之含氮雜環衍生物等。
式中，R121
~R126
係分別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中任一。但是R121
~R126
可相同或不同。R121
與R122
、R123
與R124
、R125
與R126
、R121
與R126
、R122
與R123
、R124
與R125
可形成縮合環。
也可使用美國公開2004/0113547所記載之下述式化合物。
如這些材料所代表，受體性材料也可作為電洞注入材料使用。這些具體例如上述。
除了以發光層之材料表示之前述芳香族二亞甲基系化合物外，p型Si、p型SiC等之無機化合物也可作為電洞注入．輸送層的材料使用。
電洞注入．輸送層係將本發明之芳香族胺衍生物使用例如真空蒸鍍法、旋轉塗佈法、鑄模法LB法等公知方法進行薄膜化來形成。電洞注入．輸送層之膜厚並無特別限定，一般為5nm~5μm。此電洞注入．輸送層在電洞輸送帶域中含有本發明之芳香族胺衍生物時，可以上述材料之一種或二種以上所成一層構成，也可為將與前述電洞注入．輸送層不同之化合物所成之電洞注入．輸送層予以層合者。
又，也可設置作為幫助電洞注入發光層之層的有機半導體層，以具有10－10
S/cm以上之導電率者較佳。這種有機半導體層之材料可使用含噻吩寡聚物或日本特開平8－193191號公報所揭示之含芳胺寡聚物等之導電性寡聚物、含芳胺樹枝狀聚合物等之導電性樹枝狀聚合物等。
(6)電子注入．輸送層其次電子注入層．輸送層係幫助電子注入發光層，輸送至發光區域的層，電子移動度大，附著改善層係在此電子注入層中，特別是由與陰極之附著良好的材料所形成的層。
有機EL元件係因發光的光藉由電極(此時為陰極)反射，因此與直接由陽極所取出之發光與經由電極反射取出之發光會產生干涉。欲有效利用此干涉效果，電子輸送層可選擇數nm~數μm之膜厚，特別是膜厚較厚時，欲避免電壓上昇，在外加104
~106
V/cm之電場時，電子移動度至少10－5
cm2
/Vs以上為佳。
電子注入層所用之材料，較佳為8－羥基喹啉或其衍生物之金屬錯合物或噁二唑衍生物。上述8－羥基喹啉或其衍生物之金屬錯合物之具體例，含有羥基喹啉(oxine)(一般為8－喹啉酚或8－羥基喹啉)之螯合物之金屬螯合物氧化物類化合物，例如三(8－喹啉酚)鋁可作為電子注入材料使用。
噁二唑衍生物例如有以下之一般式所示之電子傳達化合物。
芳基例如有苯基、聯苯基、蒽基、苝基、芘基。伸芳基例如有伸苯基、伸萘基、伸聯苯基、伸蒽基、伸苝基、伸芘基等。取代基例如有碳數1~10之烷基、碳數1~10之烷氧基或氰基等。此電子傳達化合物係薄膜形成性者為佳。
上述電子傳達性化合物之具體例有下述者。
電子注入層及電子輸送層所用之材料，可使用下述一般式(A)~(F)所示者。
HAr－L－Ar1
－Ar2
(C)(式中，HAr係可具有取代基之碳數3~40之含氮雜環，L係單鍵、可具有取代基之碳數6~60之伸芳基、可具有取代基之碳數3~60之雜伸芳基或可具有取代基之伸芴基，Ar1
係可具有取代基之碳數6~60之2價芳香族烴基，Ar2
表示可具有取代基之碳數6~60之芳基或可具有取代基之碳數3~60之雜芳基)所示之含氮雜環衍生物。
此金屬錯合物為n型半導體之性質強，電子注入能力大。因錯合物形成時之生成能較低，因此與形成之金屬錯合物之金屬與配位基之結合性變得強固，發光材料之螢光量子效率也變大。
形成一般式(G)之配位基之環A1
及A2
之取代基之具體例有氯、溴、碘、氟之鹵原子、甲基、乙基、丙基、丁基、第二丁基、第三丁基、戊基、己基、庚基、辛基、硬脂醯基、三氯甲基等之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－硝基苯基等之取代或無取代之芳基、甲氧基、正丁氧基、第三丁氧基、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)己氧基等之取代或無取代之烷氧基、苯氧基、對硝基苯氧基、對第三丁基苯氧基、3－氟苯氧基、五氟苯基、3－三氟甲基苯氧基等之取代或無取代之芳氧基、甲基硫基、乙基硫基、第三丁基硫基、己基硫基、辛基硫基、三氟甲基硫基等之取代或無取代之烷基硫基、苯基硫基、對硝基苯基硫基、對第三丁基苯基硫基、3－氟苯基硫基、五氟苯基硫基、3－三氟甲基苯基硫基等之取代或無取代之芳硫基、氰基、硝基、胺基、甲基胺基、二乙基胺基、乙基胺基、二乙基胺基、二丙基胺基、二丁基胺基、二苯基胺基等之單或二取代胺基、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)胺基等之醯基胺基、羥基、矽烷氧基、醯基、甲基胺甲醯基、二甲基胺甲醯基、乙基胺甲醯基、二乙基胺甲醯基、丙基胺甲醯基、丁基胺甲醯基、苯基胺甲醯基等之胺甲醯基、羧酸基、磺酸基、醯亞胺基、環戊烷基、環己基等之環烷基、苯基、萘基、聯苯基、蒽基、菲基、芴基、芘基等之芳基、吡啶基、吡嗪基、嘧啶基、噠嗪基、三嗪基、吲哚基、喹啉基、吖啶基、吡咯基、二噁烷基、哌啶基、嗎啉二基、哌嗪基、咔唑基、呋喃基、噻吩基、噁唑基、噁二唑基、苯並噁唑基、噻唑基、噻二唑基、苯並噻唑基、三唑基、咪唑基、苯並咪唑基、呋喃基等之雜環基等。又，以上之取代基彼此鍵結可形成6員芳基環或雜環。
本發明有機EL元件之較佳形態例如有輸送電子之區域或陰極與有機層之界面區域含有還原性摻雜劑的元件。還原性摻雜劑係定義為可還原電子輸送性化合物的物質。因此只要具有一定還原性者，皆可使用，例如較佳為使用至少一種選自鹼金屬、鹼土金屬、稀土金屬、鹼金屬之氧化物、鹼金屬之鹵化物、鹼土金屬之氧化物、鹼土金屬之鹵化物、稀土金屬之氧化物或稀土金屬之鹵化物、鹼金屬之有機錯合物、鹼土金屬之有機錯合物、稀土金屬之有機錯合物所成群之物質。
又，更具体而言，較佳之還原性摻雜劑例如有至少一種選自Li(功函數：2.9eV)、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，或至少一種選自Ca(功函數：2.9eV)、Sr(功函數：2.0~2.5eV)及Ba(功函數：2.52eV)所成群之一種鹼土金屬。特佳為功函數為2.9eV以下者。其中更佳之還原性摻雜劑為至少一種選自K、Rb及Cs所成群之鹼金屬，更佳為Rb或Cs，最佳為Cs。該等鹼金屬特別是還原能力高，藉由添加少量至電子注入域可提高有機EL元件中發光亮度及延長壽命。又，功函數為2.9eV以下之還原性摻雜劑，較佳為組合這些2種以上之鹼金屬，特別理想為含有Cs之組合，例如Cs與Na、Cs與K、Cs與Rb或Cs與Na與K之組合。藉由含有Cs之組合，可有效發揮還原能力，藉由添加於電子注入域，可提高有機EL元件之發光亮度或達到長壽命化。
本發明係在陰極與有機層之間可再設置以絕緣體或半導體所構成之電子注入層。此時，有效防止漏電流，可提高電子注入性。這種絕緣體可使用例如至少一種選自鹼金屬硫屬化合、鹼土金屬硫屬化合物、鹼金屬之鹵化物及鹼土金屬之鹵化物所成群之金屬化合物為佳。電子注入層為這些鹼金屬硫屬化合物等構成時，可更提高電子注入性，因此較佳。具体而言，較佳之鹼金屬硫屬化合物，例如有Li2
O、K2
O、Na2
S、Na2
Se及Na2
O，較佳之鹼土金屬硫屬化合物例如有CaO、BaO、SrO、BeO、BaS及CaSe。又，較佳之鹼金屬之鹵化物例如有LiF、NaF、KF、LiCl、KCl及NaCl等。又，較佳之鹼土金屬之鹵化物例如有CaF2
、BaF2
、SrF2
，MgF2
及BeF2
之氟化物或氟化物以外之鹵化物。
構成電子輸送層之半導體例如有含有Ba、Ca、Sr、Yb、Al、Ga、In、Li、Na、Cd、Mg、Si、Ta、Sb及Zn中至少一種元素的氧化物、氮化物或氧化氮化物等之單獨一種或二種以上之組合。又，較佳為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。電子輸送層為該等絕緣性薄膜所構成時，可形成更均質的薄膜，因此可減少暗點等像素缺陷。此外，這種無機化合物例如有上述鹼金屬硫屬化合物、鹼土金屬硫屬化合物、鹼金屬之鹵化物及鹼土金屬之鹵化物等。
(7)陰極陰極係將電子注入電子注入．輸送層或發光層中，可使用功函數較小(4eV以下)之金屬、合金、電傳導性化合物及該等混合物作為電極物質者。作為如此電極物質之具體例有鈉、鈉．鉀合金、鎂、鋰、鎂．銀合金、鋁/氧化鋁、鋁．鋰合金、銦、稀土金屬等。
此陰極可藉由蒸鍍或濺鍍等之方法將該等電極物質形成薄膜來製作。
其中，將來自發光層之發光由陰極取出時，陰極對發光的透過率大於10%較佳。
又，陰極之薄片電阻較佳為數百Ω/□以下，膜厚一般為10nm~1μm，較佳為50~200nm。
(8)絕緣層有機EL元件係將電場施加於超薄膜上，因此容易產生因漏電流或短路造成之像素缺陷。為了防止此缺陷，在一對電極間插入絕緣性之薄膜層為佳。
絕緣層所用之材料例如有氧化鋁、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、氧化釩等，也可使用這些之混合物或層合物。
(9)有機EL元件之製造方法以上例舉之材料及形成方法形成陽極、發光層，必要時形成電洞注入．輸送層及電子注入．輸送層，再形成陰極，可製作有機EL元件。也可由陰極至陽極，或與前述相反順序製作有機EL元件。
以下係敘述在透光性基板上依陽極/電洞注入層/發光層/電子注入層/陰極之順序設置之構成的有機EL元件之製作例。
首先，以蒸鍍或濺鍍等之方法於適當的透光性基板上形成由陽極材料所構成之薄膜1μm以下，較佳為10~200nm之膜厚製作陽極。接著，在此陽極上設置電洞注入層。電洞注入層之形成如前述，可使用真空蒸鍍法、旋轉塗佈法、鑄模法、LB法等方法，可容易得到均質的膜，且不易產生針孔等的觀點，以真空蒸鍍法形成較佳。以真空蒸鍍法形成電洞注入層時，其蒸鍍條件係因使用之化合物(電洞注入層之材料)、目的之電洞注入層之結晶結構或再結合結構等而異，但一般在蒸鍍源溫度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~5μm之範圍作適宜選擇為佳。
其次，於電洞注入層上設置發光層之發光層之形成也可使用所要的有機發光材料，藉由真空蒸鍍法、濺鍍、旋轉塗佈法、鑄模法等之方法，使有機發光材料形成薄膜化來形成，但從易於獲得均質膜，且不易產生針孔等的觀點，使用真空蒸鍍法來形成較佳。藉由真空蒸鍍法形成發光層時，其蒸鍍條件係依使用之化合物而異，但一般可選自與電洞注入層相同之條件。
接著，於此發光層上設置電子注入層。與電洞注入層、發光層同樣地，為了得到均質膜，因此以真空蒸鍍法來形成較佳。蒸鍍條件可選自與電洞注入層、發光層同樣的條件範圍。
本發明之芳香族胺衍生物係因存在於發光帶域或電洞輸送帶域其中一層而異，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，可藉由由與其他材料混合而含於其中。
最後層合陰極可得到有機EL元件。
陰極係由金屬所構成，故可使用蒸鍍法、濺鍍。但欲保護在製膜時損傷基底之有機物層時，以真空蒸鍍法為佳。
該有機EL元件之製作係於一次抽真空下，由陽極至陰極進行一貫製作為佳。
本發明之有機EL元件之各層之形成方法並無特別特定。可使用習知之真空蒸鍍法、旋轉塗佈法等之形成方法。本發明之有機EL元件所用之含有前述一般式(1)所示之化合物的有機薄膜層可藉由真空蒸鍍法、分子線蒸鍍法(MBE法)或溶解於溶劑之溶液的浸漬法、旋轉塗佈法、鑄膜法、棒塗佈法、輥塗佈法等之塗佈法等公知方法來形成。
本發明之有機EL元件的各有機層之膜厚並無特別限定，但一般膜厚過薄時容易產生針孔等之缺陷，相反地，過厚時因需要較高之外加電壓，因此效率變差，一般以數nm~1μm之範圍為佳。
對有機EL元件施加直流電壓時，陽極為＋，陰極為－之極性，外加5~40V之電壓時，可觀測到發光。又，以相反極性即使施加電壓時，電流也不會流通，完全不會發光。施加交流電壓時，僅在陽極為＋，陰極為－之極性時可觀測到均勻的發光。施加之交流的波形可為任意波形。
以下，依據合成例及實施例更詳細說明本發明。
合成例1~21製造之中間體1~21的結構式如下述。
氫氣流下，將4－溴聯苯47g、碘23g、過碘酸2水合物9.4g、水42mL、乙酸360mL、硫酸11mL投入1000mL的三口燒瓶中，65℃下攪拌30分鐘後，以90℃反應6小時。將反應物注入冰水中，進行過濾。以水洗淨後，再以甲醇洗淨得到67g的白色粉末。藉由FD－MS(場解析－質譜)分析得到對C12
H15
BrI＝359,m/z＝358與360的主波峰，因此鑑定為中間體1。
氬氣流下，將對三聯苯10g、碘12g、過碘酸2水合物4.9g、水20mL、乙酸170mL、硫酸22mL投入300mL的三口燒瓶中，65℃下攪拌30分鐘後，90℃下反應6小時。將反應物注入冰水中，然後過濾。以水洗淨後，以甲醇洗淨得到18g的白色粉末。藉由FD－MS之分析得到對C18
H12
I2
＝482，m/z＝482的主波峰，因此鑑定為中間體2。
氬氣流下，將苯基硼酸750g、2－溴噻吩1000g、四(三苯基膦)鈀(Pd(PPh3
)4
)142g、2M之碳酸鈉(Na2
CO3
)溶液9L、二甲氧基乙烷15L投入50L之反應容器內，然後以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。再於減壓下濃縮得到之粗生成物以柱(clumn)純化，得到786g之白色粉末。
氬氣流下，將上述製得之化合物786g與N,N－二甲基甲醯胺(DMF)8L投入20L之反應容器內後，慢慢添加N－溴琥珀醯亞胺(NBS)960g，然後室溫反應12小時。以己烷/水進行萃取，以無水硫酸鈉乾燥。再於減壓下濃縮得到之粗生成物以柱(clumn)純化，得到703g之白色粉末。藉由FD－MS之分析鑑定為中間體3。
氬氣流下，將中間體(3)703g、脫水四氫呋喃(THF)7L添加於20L之反應容器內，冷卻至－30℃。添加正丁基鋰(n－BuLi,1.6M己烷溶液)2.3L，反應1小時。冷卻至－70℃後，添加硼酸三異丙酯(東京化成公司製)1658g。慢慢昇溫，在室溫下攪拌1小時。添加10%鹽酸1.7L進行攪拌。使用乙酸乙酯與水萃取，有機層用水洗淨。以無水硫酸鈉乾燥，餾去溶劑。以己烷洗淨得到359g之白色粉末。
氬氣流下，將上述所得之5－苯基－2－噻吩硼酸506g、4－碘溴苯600g、四(三苯基膦)鈀(Pd(PPh3
)4
)41g、2M之碳酸鈉(Na2
CO3
)溶液2.6L、二甲氧基乙烷10L投入20L之反應容器內，然後以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。再於減壓下濃縮得到之粗生成物以柱純化，得到277g之白色粉末。藉由FD－MS之分析鑑定為中間體4。
除了使用中間體1取代中間體4之合成之4－碘溴苯外，同樣進行反應，得到342g之白色粉末。藉由FD－MS之分析鑑定為中間體5。
除了使用5－甲基－2－噻吩硼酸取代中間體4之合成之5－苯基－2－噻吩硼酸外，同樣進行反應，得到203g之白色粉末。藉由FD－MS之分析鑑定為中間體6。
氬氣流下，投入苯胺5.5g、中間體(4)15.7g、第三丁氧基鈉(廣島和光公司製)6.8g、三(二苯亞甲基丙酮)二鈀(0)(Aldrich公司製)0.46g及脫水甲苯300mL，在80℃下反應8小時。
冷卻後，添加水500mL，將混合物以矽藻鹽過濾，以甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮所得之粗生成物以管柱純化，使用甲苯再結晶，經濾過取得後，乾燥得到10.8g之淡黃色粉末。藉由FD－MS之分析鑑定為中間體8。
除了使用中間體6取代中間體8之合成之中間體4外，同樣進行反應，得到7.3g之白色粉末。藉由FD－MS之分析鑑定為中間體9。
氬氣流下，投入乙醯胺185g(東京化成公司製)、中間體(4)315g、碳酸鉀544g(和光純藥公司製)、銅粉12.5g(和光純藥公司製)及十氫化萘2L，以190℃反應4日。反應後冷卻，添加甲苯2L，濾取不溶份。將濾取物溶解於氯仿4.5L中，除去不溶份後，以活性碳處理濃縮。此濃縮物中添加丙酮3L，濾取析出晶175g。
將此析出晶懸浮於乙二醇5L(和光純藥公司製)、水50mL中，添加85%氫氧化鉀水溶液210g後，在120℃下反應8小時。反應後，將反應液注入水10L中，濾取析出之結晶，以水、甲醇洗淨。將得到的結晶加熱溶解於四氫呋喃3L中，以活性碳處理後濃縮，添加丙酮使結晶析出。濾取析出之結晶，得到145g的白色粉末。藉由FD－MS分析鑑定為中間體11。
氬氣流下，投入乙醯胺185g(東京化成公司製)、4－溴聯苯253g(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)及十氫化萘2L，以190℃反應4日。反應後冷卻，添加甲苯2L，濾取不溶份。將濾取物溶解於氯仿4.5L中，除去不溶份後，以活性碳處理濃縮。其中添加丙酮3L，濾取析出結晶205g。
上述結晶中添加中間體(4)177g、碳酸鈉380g(和光純藥公司製)、銅粉8.8g(和光純藥公司製)及十氫化萘2L，以190℃反應4日。反應後冷卻，添加甲苯1.4L，濾取不溶份。將濾取物溶解於氯仿3L中，除去不溶份後，以活性碳處理濃縮。此濃縮物中添加丙酮3L，濾取析出之結晶224g。將此析出晶懸浮於乙二醇3.5L(和光純藥公司製)、水35mL中，添加85%氫氧化鉀水溶液147g後，在120℃下反應8小時。反應後，將反應液注入水10L中，濾取析出之結晶，以水、甲醇洗淨。將得到的結晶加熱溶解於四氫呋喃3L中，以活性碳處理後濃縮，添加丙酮使結晶析出。濾取析出之結晶，得到141g的白色粉末。藉由FD－MS分析鑑定為中間體12。
除了在中間體11之合成時，中間體4由315g改為630g外，同樣進行反應，得到240g的白色粉末。藉由FD－MS分析鑑定為中間體13。
除了使用中間體6取代中間體13之合成之中間體4外，同樣進行反應，得到140g之白色粉末。藉由FD－MS之分析鑑定為中間體14。
除了使用中間體11取代中間體8之合成時之苯胺，使用1－複萘取代中間體4外，同樣進行反應，得到12g的白色粉末。藉由FD－MS分析鑑定為中間體16。
氬氣流下，投入乙醯胺185g(東京化成公司製)、中間體(4)315g、碳酸鉀544g(和光純藥公司製)、銅粉12.5g(和光純藥公司製)及十氫化萘2L，以190℃反應4日。反應後冷卻，添加甲苯2L，濾取不溶份。將濾取物溶解於氯仿4.5L中，除去不溶份後，以活性碳處理濃縮。此濃縮物中添加丙酮3L，濾取析出結晶175g。
上述結晶中添加4,4，
－二碘聯苯120g(和光純藥公司製)、碳酸鉀163g(和光純藥公司製)、銅粉3.8g(和光純藥公司製)及十氫化萘600mL，以190℃反應4日。
反應後冷卻，添加甲苯600mL，濾取不溶份。將濾取物溶解於氯仿1.4L中，除去不溶份後，以活性碳處理濃縮。此濃縮物中添加丙酮1L，濾取析出之結晶382g。
將此析出晶懸浮於乙二醇1.5L(和光純藥公司製)、水15mL中，添加85%氫氧化鉀水溶液44g後，在120℃下反應8小時。反應後，將反應液注入水10L中，濾取析出之結晶，以水、甲醇洗淨。將得到的結晶加熱溶解於四氫呋喃1L中，以活性碳處理後濃縮，添加丙酮使結晶析出。濾取析出之結晶，得到130g的白色粉末。藉由FD－MS分析鑑定為中間體17。
氬氣流下，投入1－乙醯胺萘547g(東京化成公司製)、4,4’－二碘聯苯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)及十氫化萘2L，以190℃反應4日。
反應後冷卻，添加甲苯2L，濾取不溶份。將濾取物溶解於氯仿4.5L中，除去不溶份後，以活性碳處理濃縮。其中添加丙酮3L，濾取析出結晶382g。將此析出晶懸浮於乙二醇5L(和光純藥公司製)、水50mL中，添加85%氫氧化鉀水溶液145g後，在120℃下反應8小時。反應後，將反應液注入水10L中，濾取析出之結晶，以水、甲醇洗淨。將得到的結晶加熱溶解於四氫呋喃3L中，以活性碳處理後濃縮，添加丙酮使結晶析出。濾取析出之結晶，得到264g的白色粉末。藉由FD－MS分析鑑定為中間體18。
氬氣流下，投入二苯胺5.1g、中間體(1)10.8g、第三丁氧基鈉3g(廣島和光公司製)、雙(三苯基膦)氯化鈀(II)0.5g(東京化成公司製)及二甲苯500mL，以130℃下反應24小時。
冷卻後，添加水1000mL，將混合物以矽藻鹽過濾，使用甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮，所得之粗生成物以管柱純化，使用甲苯再結晶，經過濾取得後，乾燥得到3.4g之淡黃色粉末。藉由FD－MS之分析鑑定為中間體19。
除了使用4－碘溴苯取代合成例19之中間體1外，同樣進行反應，得到2.8g之白色粉末。藉由FD－MS之分析鑑定為中間體20。
200mL之三口燒瓶中加入4－溴聯苯20.0g(東京化成公司品)、第三丁氧基鈉8.64g(和光純藥公司製)、乙酸鈀84mg(和光純藥公司製)。放入攪拌子，於燒瓶之兩側設置橡膠套(rubber cap)，中央口設置迴流用蛇管，其上設置三向旋塞(cock)與封入氬氣之氣球，使用真空幫浦將體系內以氣球內之氬氣3次取代。
其次，以注射器通過橡膠隔壁(septum)添加脫水甲苯120mL(廣島和光公司製)、苄胺4.08mL(東京化成公司製)、三第三丁基膦338μL(aldrich公司製，2.22mol/L甲苯溶液)，室溫下攪拌5分鐘。將燒瓶設置於油浴上，溶液邊攪拌下緩慢升溫至120℃。7小時後，將燒瓶自油浴移開，結束反應，在氬氣氛下放置12小時。將反應溶液移至分液漏斗中，添加之二氯甲烷600mL，使沈澱物溶解，以飽和食鹽水120mL洗淨後，將有機層以無水碳酸鉀乾燥。過濾碳酸鉀，餾去所得之有機層的溶劑，所得之殘渣中添加甲苯400mL、乙醇80mL，附上乾燥管並加熱至80℃，使殘渣完全溶解後放置12小時，慢速冷卻至室溫使其再結晶。過濾所析出之結晶，以60℃真空乾燥得到N,N－二－(4－聯苯基)－苄胺13.5g。300ml之一口燒瓶中添加1.35g之N,N－二－(4－聯苯基)－苄胺、鈀－活性碳135mg(廣島和光公司製，鈀含量10重量%)，再添加氯仿100mL、乙醇20mL進行溶解。其次，將攪拌子放入燒瓶中，將安裝填充氫氣2L之氣球的三方向旋塞裝置於燒瓶上，使用真空幫浦將燒瓶體系內以氫氣10次取代。減少的氫氣再重新填充，使氫氣之容積再度成為2L後，室溫下將溶液劇烈攪拌。攪拌30小時後，添加二氯甲烷100mL，將觸媒過濾。接著將所得之溶液移至分液漏斗，以碳酸氫鈉飽和水溶液50mL洗淨後，分離有機層後，以無水碳酸鉀乾燥。過濾後餾去溶劑，所得之殘渣中添加甲苯50mL再進行再結晶。過濾析出之結晶，於50℃下進行真空乾燥後得到0.99g之二－4－聯苯胺。
氬氣流下，投入二－4－聯苯胺10g、4,4’－二溴聯苯9.7g(東京化成公司製)、第三丁氧基鈉3g(廣島和光公司製)、雙(三苯基膦)氯化鈀(II)0.5g(東京化成公司製)及二甲苯500mL，以130℃下反應24小時。冷卻後，添加水1000mL，將混合物以矽藻鹽過濾，使用甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮，所得之粗生成物以管柱純化，使用甲苯再結晶，經過濾取得後，乾燥得到9.1g之下述4’－溴－N,N－二聯苯基－4－胺基－1,1’－聯苯(中間體21)。
合成實施例1~20製造之本發明之芳香族胺衍生物的化合物H1~H20之結構式如下述。
氬氣流下，投入N,N’－二苯基聯苯胺3.4g、中間體(4)6.6g、第三丁氧基鈉2.6g(廣島和光公司製)、三(二苯亞甲基丙酮)二鈀(0)(Aldrich公司製)92mg、三第三丁基膦42mg及脫水甲苯100mL，在80℃下反應8小時。
冷卻後，添加水500mL，將混合物以矽藻鹽過濾，以甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮，所得之粗生成物以管柱純化，使用甲苯再結晶，經濾過取得後，乾燥得到4.0g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H1。
氬氣流下，投入4,4’－二碘聯苯4.1g、中間體(12)8.4g、第三丁氧基鈉2.6g(廣島和光公司製)、三(二苯亞甲基丙酮)二鈀(0)(Aldrich公司製)92mg、三第三丁基膦42mg及脫水甲苯100mL，在80℃下反應8小時。
冷卻後，添加水500mL，將混合物以矽藻鹽過濾，以甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮，所得之粗生成物以管柱純化，使用甲苯再結晶，經濾過取得後，乾燥得到4.8g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H2。
除了使用中間體(18)4.4g取代合成實施例1之N,N’－二苯基聯苯胺外，進行同樣反應得到5.1g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H3。
除了使用中間體(5)8.1g取代合成實施例1之中間體4外，進行同樣反應得到5.3g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H4。
氬氣流下，投入中間體(12)8.1g、中間體(21)11.0g、第三丁氧基鈉2.6g(廣島和光公司製)、三(二苯亞甲基丙酮)二鈀(0)(Aldrich公司製)92mg、三第三丁基膦42mg及脫水甲苯100mL，在80℃下反應8小時。
冷卻後，添加水500mL，將混合物以矽藻鹽過濾，以甲苯萃取濾液，以無水硫酸鎂乾燥。再於減壓下濃縮，所得之粗生成物以管柱純化，使用甲苯再結晶，經濾過取得後，乾燥得到13.1g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H5。
除了使用中間體(8)6.5g取代合成實施例5之中間體12外，進行同樣反應得到7.9g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H6。
除了使用中間體(16)7.5g取代合成實施例5之中間體12外，進行同樣反應得到7.9g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H7。
除了使用中間體(13)9.7g取代合成實施例5之中間體12外，進行同樣反應得到10.2g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H8。
除了使用中間體(13)9.7g取代合成實施例2之中間體12外，進行同樣反應得到4.3g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H9。
除了使用中間體(9)7.2g取代合成實施例2之中間體12外，進行同樣反應得到3.6g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H10。
除了使用中間體(14)7.2g取代合成實施例2之中間體12外，進行同樣反應得到5.3g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H12。
除了中間體(2)4.8g取代合成實施例2之4,4’－二碘聯苯，使用中間體(8)6.5g取代中間體12外，進行同樣反應得到3.9g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H14。
除了使用1,4－二碘苯3.3g取代合成實施例2之4,4’－二碘聯苯，使用中間體(8)6.5g取代中間體12外，進行同樣反應得到3.3g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H15。
除了使用中間體(11)2.5g取代合成實施例1之N,N’－二苯基聯苯胺，使用中間體(19)8.0g取代中間體4外，進行同樣反應得到2.1g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H16。
除了使用中間體(17)6.5g取代合成實施例1之N,N’－二苯基聯苯胺，使用中間體(19)8.0g取代中間體4外，進行同樣反應得到7.1g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H17。
除了使用中間體(17)6.5g取代合成實施例1之N,N’－二苯基聯苯胺，使用中間體(20)8.0g取代中間體4外，進行同樣反應得到5.9g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H18。
除了使用2,7－二溴－9,9－二甲基芴3.5g取代合成實施例2之4,4’－二碘聯苯，使用中間體(8)6.5g取代中間體12外，進行同樣反應得到3.7g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H19。
除了使用三(4－溴苯基)胺4.8g取代合成實施例2之4,4’－二碘聯苯，使用中間體(8)9.7g取代中間體12外，進行同樣反應得到4.8g之淡黃色粉末。藉由FD－MS(場解析－質譜)之分析鑑定為化合物H20。
將25mm×75mm×1.1mm厚之附有ITO透明電極之玻璃基板(Geomatic公司製)在異丙基醇中進行超音波洗淨5分鐘後，進行UV臭氧洗淨30分鐘。
將洗淨後之附透明電極線之玻璃基板安裝於真空蒸鍍裝置之基板保持架，首先在形成透明電極線之側的面上形成膜厚60nm之上述化合物H1覆蓋前述透明電極。此H1膜具有電洞注入層的功能。此H1膜上形成膜厚20nm之下述化合物層TBDB。此膜具有電洞輸送層的功能。再蒸鍍膜厚40nm之下述化合物EM1形成膜。同時以EM1與D1之重量比成為40：2的狀態蒸鍍具有下述苯乙烯基之胺化合物D1作為發光分子。此膜係具有發光層的功能。
此膜上形成膜厚10nm之下述Alq膜。此膜具有電子注入層的功能。然後，將還原性摻雜劑之Li(Li源：SAYESGETTER公司製)與Alq進行二元蒸鍍，形成作為電子注入層(陰極)之Alq：Li膜(膜厚10nm)。此Alq：Li膜上蒸鍍金屬Al，形成金屬陰極，製作有機EL元件。
對於製得之有機EL元件測定發光效率，觀察發光色。發光效率係使用Minolta製CS1000測定亮度，計算10mA/cm2
之發光效率。再於初期亮度5000cd/m2
、室溫、DC定電流驅動下測定發光減半壽命，結果如表1所示。
除了使用表1記載之化合物取代實施例1中作為電洞輸送材料的化合物H1外，其他同樣製造有機EL元件。
對於製得之有機EL元件測定其發光效率，觀察發光色，再於初期亮度5000cd/m2
、室溫、DC定電流驅動下測定發光減半壽命，結果如表1所示。
除了使用比較化合物1~比較化合物7取代實施例1中，作為電洞輸送材料之化合物H1外，其餘同樣製造有機EL元件。
對於製得之有機EL元件測定其發光效率，並觀察其發光色。測定初期亮度5000cd/m2
，室溫，DC定電流驅動之發光減半壽命之結果如表1所示。
除了使用下述芳基胺化合物D2取代實施例1中，具有苯乙烯基之胺化合物D1外，其他同樣製造有機EL元件。Me表示甲基。
對於製得之有機EL元件測定其發光效率，並觀察其發光色，測定初期亮度5000cd/m2
、室溫、DC定電流驅動之發光減半壽命之結果如表1所示。
除了使用比較化合物1取代實施例13中，作為電洞輸送材料之化合物H1外，其餘同樣製造有機EL元件。
對於製得之有機EL元件測定其發光效率，並觀察其發光色，測定初期亮度5000cd/m2
、室溫、DC定電流驅動之發光減半壽命之結果如表1所示。
除了實施例1中，陽極與上述化合物H1之間形成10nm之下述受體化合物膜，將上述化合物H1之膜厚改為50nm外，同樣製造有機EL元件。
對於製得之有機EL元件測定其發光效率，並觀察其發光色，測定初期亮度5000cd/m2
、室溫、DC定電流驅動之發光減半壽命之結果如表1所示。
除了使用比較化合物1取代實施例14中，作為電洞輸送材料之化合物H1外，其餘同樣製造有機EL元件。對於製得之有機EL元件測定其發光效率，並觀察其發光色，測定初期亮度5000cd/m2
、室溫、DC定電流驅動之發光減半壽命之結果如表1所示。
關於H1與H12及比較化合物4分別確認以壽命測定後200小時之電壓上升(△V＝(200小時後之電壓)－(初期電壓))時，H1為0.2V，H12為0.4V，比較化合物5為0.7V。越是電性不安定之化合物，則電壓上升越高。
如上述詳細說明，本發明之芳香族胺胺衍生物係使驅動電壓降低，同時分子不易結晶化，有機薄膜層中含有此芳香族胺衍生物時，可提高製造有機EL元件時之良率，得到長壽命之有機EL元件。
Claims (38)
- 一種芳香族胺衍生物，其係以下述一般式(1)表示，
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(2)為下述一般式(3)表示，
- 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 為該一般式(2)表示。
- 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Ar2 為該一般式(2)表示。
- 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(2)表示。
- 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 ~Ar4 之中3個以上係互不相同，且非對稱。
- 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 ~Ar4 之中3個相同，且非對稱。
- 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 ~Ar4 之中，非一般式(2)者係分別獨立為苯基、聯苯基、三聯苯基或芴基。
- 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，L1 為伸聯苯基、伸三聯苯基或伸芴基。
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(2)中，L2 為伸苯基、伸聯苯基或伸芴基。
- 如申請專利範圍第1項之芳香族胺衍生物，其中該一般式(2)中，R1 為苯基、萘基或菲基。
- 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 ~Ar4 之中，非一般式(2)者係分別獨立為苯基、聯苯基、三聯苯基或芴基，L1 為伸聯苯基、伸三聯苯基或伸芴基，該一般式(2)中，L2 為伸苯基、伸聯苯基或伸芴基。
- 一種芳香族胺衍生物，其係以下述一般式(4)~(6)中任一表示，
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(7)為下述一般式(8)表示，
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)中，Ar5 ~Ar9 之中至少1個係以一般式 (7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)中，Ar5 為該一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)中，Ar6 與Ar8 為該一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(5)中，Ar10 ~Ar15 之中，至少1個係以一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(5)中，Ar10 與Ar15 為該一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(5)中，Ar11 與Ar13 為該一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(6)中，Ar16 ~Ar21 之中，至少1個係以一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(6)中，Ar16 與Ar18 與Ar20 為該一般式(7)表示。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)~(6)中，Ar5 ~Ar21 之中，非一般式(7)者係分別獨立為苯基、聯苯基、三聯苯基或芴基。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)~(6)中，L5 ~L12 係分別獨立為伸苯基、伸聯苯基、伸三聯苯基或伸芴基。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(7)中，L2 為伸苯基、伸聯苯基或伸芴基。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(7)中，R1 為苯基、萘基或菲基。
- 如申請專利範圍第13項之芳香族胺衍生物，其中該一般式(4)~(6)中，Ar5 ~Ar21 之中，非一般式(7)者係分別獨立為苯基、聯苯基、三聯苯基或芴基，L5 ~L12 為伸苯基、伸聯苯基、伸三聯苯基或伸芴基，一般式(7)中，L2 為伸苯基、伸聯苯基或伸芴基。
- 如申請專利範圍第1~27項中任一項之芳香族胺衍生物，其係有機電致發光元件用材料。
- 如申請專利範圍第1~27項中任一項之芳香族胺衍生物，其係蒸鍍用有機電致發光元件用材料。
- 如申請專利範圍第1~27項中任一項之芳香族胺衍生物，其係有機電致發光元件用電洞輸送材料。
- 一種有機電致發光元件，其係於陰極與陽極間挾持至少含有發光層之一層或多層所構成之有機薄膜層的有機電致發光元件，其特徵係該有機薄膜層之至少一層為含有申請專利範圍第1~27項中任一項之芳香族胺衍生物作為單獨或混合物的成分。
- 如申請專利範圍第31項之有機電致發光元件，其中該有機薄膜層具有電洞輸送層，該電洞輸送層中含有該芳香族胺衍生物。
- 如申請專利範圍第31項之有機電致發光元件， 其中該有機薄膜層具有多層電洞輸送層，未直接接觸發光層的層中含有該芳香族胺衍生物。
- 如申請專利範圍第31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，該電洞注入層中含有該芳香族胺衍生物。
- 如申請專利範圍第31項之有機電致發光元件，其中電洞輸送層中含有該芳香族胺衍生物作為主成分。
- 如申請專利範圍第31項之有機電致發光元件，其中發光層中含有苯乙烯基胺化合物及/或芳基胺化合物。
- 如申請專利範圍第31項之有機電致發光元件，其中構成該電洞注入層及電洞輸送層之各層之中，與陽極接觸的層含有受體材料。
- 如申請專利範圍第31項之有機電致發光元件，其係發藍色系光。
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- 2007-08-01 WO PCT/JP2007/065061 patent/WO2008023549A1/ja active Application Filing
- 2007-08-01 JP JP2008530843A patent/JP5203207B2/ja not_active Expired - Fee Related
- 2007-08-01 JP JP2008530844A patent/JP5139297B2/ja not_active Expired - Fee Related
- 2007-08-01 KR KR1020097003487A patent/KR20090040896A/ko not_active Application Discontinuation
- 2007-08-01 KR KR1020097003486A patent/KR20090040895A/ko not_active Application Discontinuation
- 2007-08-01 CN CNA2007800306655A patent/CN101506192A/zh active Pending
- 2007-08-01 EP EP07805888A patent/EP2055701A1/en not_active Withdrawn
- 2007-08-01 WO PCT/JP2007/065062 patent/WO2008023550A1/ja active Application Filing
- 2007-08-06 US US11/834,203 patent/US20080106190A1/en not_active Abandoned
- 2007-08-06 US US11/834,157 patent/US8044222B2/en active Active
- 2007-08-09 TW TW096129437A patent/TW200827342A/zh unknown
- 2007-08-09 TW TW096129436A patent/TW200833673A/zh unknown
- 2007-08-23 TW TW096131244A patent/TWI488848B/zh active
- 2007-08-23 US US11/844,050 patent/US20080108832A1/en not_active Abandoned
- 2007-08-23 CN CN200780031236.XA patent/CN101506191B/zh active Active
- 2007-08-23 WO PCT/JP2007/066356 patent/WO2008023759A1/ja active Application Filing
- 2007-08-23 JP JP2008530950A patent/JP4403201B2/ja active Active
- 2007-08-23 EP EP07792934.7A patent/EP2055700B1/en active Active
- 2007-08-23 KR KR1020097003499A patent/KR101152999B1/ko active IP Right Grant
-
2013
- 2013-11-26 US US14/091,044 patent/US9112167B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20090040895A (ko) | 2009-04-27 |
| KR20090040896A (ko) | 2009-04-27 |
| KR101152999B1 (ko) | 2012-06-04 |
| US8044222B2 (en) | 2011-10-25 |
| US20080108839A1 (en) | 2008-05-08 |
| KR20090036139A (ko) | 2009-04-13 |
| EP2055700B1 (en) | 2015-09-30 |
| TW200827342A (en) | 2008-07-01 |
| EP2055700A1 (en) | 2009-05-06 |
| JPWO2008023550A1 (ja) | 2010-01-07 |
| WO2008023549A1 (fr) | 2008-02-28 |
| US20080108832A1 (en) | 2008-05-08 |
| US20140077200A1 (en) | 2014-03-20 |
| WO2008023759A1 (fr) | 2008-02-28 |
| CN101506191B (zh) | 2014-06-25 |
| JPWO2008023759A1 (ja) | 2010-01-14 |
| JP5203207B2 (ja) | 2013-06-05 |
| US9112167B2 (en) | 2015-08-18 |
| JPWO2008023549A1 (ja) | 2010-01-07 |
| CN101506192A (zh) | 2009-08-12 |
| TW200838858A (en) | 2008-10-01 |
| JP4403201B2 (ja) | 2010-01-27 |
| JP5139297B2 (ja) | 2013-02-06 |
| US20080106190A1 (en) | 2008-05-08 |
| TW200833673A (en) | 2008-08-16 |
| CN101506191A (zh) | 2009-08-12 |
| EP2055700A4 (en) | 2010-10-06 |
| EP2055701A1 (en) | 2009-05-06 |
| WO2008023550A1 (fr) | 2008-02-28 |
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