TW201434818A - 熒蔥化合物及包含其之有機電子裝置 - Google Patents
熒蔥化合物及包含其之有機電子裝置 Download PDFInfo
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- TW201434818A TW201434818A TW102142400A TW102142400A TW201434818A TW 201434818 A TW201434818 A TW 201434818A TW 102142400 A TW102142400 A TW 102142400A TW 102142400 A TW102142400 A TW 102142400A TW 201434818 A TW201434818 A TW 201434818A
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- -1 Fluoranthene compound Chemical class 0.000 title claims abstract description 48
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 239000000126 substance Substances 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims description 79
- 239000011368 organic material Substances 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 43
- 239000007924 injection Substances 0.000 claims description 43
- 241000234282 Allium Species 0.000 claims description 30
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 230000005525 hole transport Effects 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004437 phosphorous atom Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 2
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 2
- BGXMTJUKHLHKPN-UHFFFAOYSA-N C1=CC=CC=2C1=C1NC3=CC=CC=C3C1=CC2.C2=CC=CC=1C2=C2NC3=CC=CC=C3C2=CC1 Chemical group C1=CC=CC=2C1=C1NC3=CC=CC=C3C1=CC2.C2=CC=CC=1C2=C2NC3=CC=CC=C3C2=CC1 BGXMTJUKHLHKPN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001638 boron Chemical class 0.000 claims 1
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- 238000001802 infusion Methods 0.000 claims 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical class P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000037452 priming Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 26
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 12
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- 238000000151 deposition Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
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- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 4
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- LFQRKUIOSYPVFY-UHFFFAOYSA-L dipotassium diacetate Chemical compound [K+].[K+].CC([O-])=O.CC([O-])=O LFQRKUIOSYPVFY-UHFFFAOYSA-L 0.000 description 1
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- YTPGCOSTHSDLPN-UHFFFAOYSA-N ethene naphthalene-1,4-dione Chemical compound C=C.C1(C=CC(C2=CC=CC=C12)=O)=O YTPGCOSTHSDLPN-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
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- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical class [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
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- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- ALAGDBVXZZADSN-UHFFFAOYSA-N pentazine Chemical group C1=NN=NN=N1 ALAGDBVXZZADSN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical group N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- HFRYYTUQIYTHCH-UHFFFAOYSA-N tetrasodium butan-1-olate Chemical compound [O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Na+].[Na+].[Na+].[Na+] HFRYYTUQIYTHCH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical class [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- H—ELECTRICITY
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
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- 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
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Abstract
本發明係有關於一種新穎熒蔥化合物,該化合物能夠大幅地改善有機電子裝置的壽命、效率、電性及化學穩定性,以及熱穩定性。此外,本發明還提供一種有機電子裝置,其有機化合物層中包含有該化合物。
Description
本發明是有關於一種熒蔥化合物以及一種包含該化合物的有機電子裝置。
本申請案主張韓國專利申請案No.10-2012-0132190的優先權及其利益,該申請案於2012年11月21日向韓國智慧財產局提出申請,該案所揭示之全部內容併入本發明中以資參考。
一種有機電子裝置係指一種裝置需要在一電極與一有機材料之間,利用電洞及/或電子產生電荷交換。根據運作的原則,有機電子裝置主要可以被分類成兩大類。第一大類係一種電子裝置,它利用由外部來源帶入裝置的光子,使有機材料層中產生激發子(excitons),該些激發子被分成電子與電洞,藉由該電子與該電洞被傳輸到不同電極,使得該電子裝置,能夠作為一電流源(或電壓源)。第二大類係一種電子裝置,該電子裝置是藉由注入電子與電洞來運作;在該電子裝置中,一有機材料半導體跟一電極形成一界面,藉由對二個或多個電極施加電壓或電流,使電洞及/或電子被注入到該有機材料半導體中。
該有機電子裝置的例子,包括:有機發光裝置(organic light emitting device)、有機太陽能電池(organic solar cell)、有機導光體(organic photo conductor,OPC)、有機電晶體(organic transistor)等,驅動該些裝置都需要電洞注入(或傳輸)材料、電子注入(或傳輸)材料或發光材料。後面,我們會詳細描述一種有機發光裝置,不過,該些有機電子裝置都是在相似的原理下,使用一電洞注入(或傳輸)材料、一電子注入(或傳輸)材料或一發光材料。
一般而言,一有機發光現象,係屬於利用一有機材料將電能轉換成光能的現象。利用有機發光現象的有機發光裝置,基本上包含一陽極、一陰極,以及介於其間的一有機材料層的結構。通常,該有機材料層是由不同材料所形成的多層結構,用來改善有機發光裝置的效率與穩定性,例如可為電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層等等。在該有機發光裝置的結構中,當在該兩電極間施加電壓時,從陽極來的電洞與從陰極來的電子會流進有機材料層。當該些被注入的電子與電洞結合時,就會產生激發子,然後,在激發子回到基態的時候,就會發出光。這樣的有機發光裝置已知具有下列特性:自發光、高亮度、高效率、低驅動電壓、廣視角、高對比、以及反應速率快。
在一種有機發光裝置中,用來當作有機材料層的材料可分成發光材料與電荷傳輸材料,將該電荷傳輸材料依據功能來分,例如:電洞注入材料、電洞傳輸材料、
電子傳輸材料、電子注入材料等等。此外,將該發光材料依據發光的顏色來分,例如:藍色、綠色與紅色發光材料,以及可以得到更好的自然色的黃色與橘色的發光材料。此時,當只有一種材料用來當作發光材料時,會發生許多問題,例如:因為分子間的交互作用,使得最大的發光波長偏移到長波長;色彩的純度降低;或由於發光的消光效應(diminution effect),使得該裝置的效率降低。因此,一種以主發光體/摻雜物為基底(host/dopant-base)的材料被用來當作發光材料,以增加色彩的純度及透過能量轉換增加發光效率。
為了讓有機發光裝置能夠顯示出上述的優良特性,用來形成有機材料層的材料,例如:電洞注入材料、電洞傳輸材料、發光材料、電子傳輸材料、電子注入材料等等,需要先被穩定且有效率的材料所支撐,然而,這種用來當作有機發光裝置中有機材料層之穩定且有效率的支撐材料,到目前為止,它的開發仍然有所不足,因此,需要持續開發新材料,而且這些開發出來的材料也可以應用到上述的其他有機電子裝置。
先前技術的文件,韓國專利申請案早期公開號No.2007-001220。
綜上所述,本發明的目標在提供一種熒蔥化合物的衍生物以及提供一種包含該熒蔥化合物的衍生物的有機電子裝置,該衍生物具有的化學結構,可依據取代基而
扮演有機電子裝置所需的各種角色。
本發明提供一種熒蔥化合物,如以下化學式1所示:[化學式1]
在化學式1中,R1至R3基團以-(L)p-(Y)q表示;p為0至10之一整數;q為1至10之一整數;o為1至5之一整數;r為0至6之一整數;L為經取代或未經取代之亞芳基(arylene group)、經取代或未經取代之伸烯基(alkenylene group)、經取代或未經取代之茀烯基(fluoreylene group)或經取代或未經取代包含氧(O)、氮(N)、硫(S)或磷(P)雜原子之雜亞芳基(heteroarylene
group);Y係氫、氘、鹵基、腈基(nitrile group)、硝基(nitro group)、氫氧基、經取代或未經取代之烷基(alkyl group)、經取代或未經取代之環烷基(cycloalkyl group)、經取代或未經取代之烷氧基(alkoxy group)、經取代或未經取代之膦氧化物基(phosphine oxide group)、經取代或未經取代之芳氧基(aryloxy group)、經取代或未經取代之烷硫氧基(alkylthioxy group)、經取代或未經取代之芳硫氧基(arylthioxy group)、經取代或未經取代之烷磺氧基(alkylsulfoxy group)、經取代或未經取代之芳磺氧基(arylsulfoxy group)、經取代或未經取代之烯基(alkenyl group)、經取代或未經取代之矽烷基(silyl group)、經取代或未經取代之硼基(boron group)、經取代或未經取代之胺基(amine group)、經取代或未經取代之烷胺基(alkylamine group)、經取代或未經取代之芳烷胺基(aralkylamine group)、經取代或未經取代之芳胺基(arylamine group)、經取代或未經取代之雜芳胺基(heteroarylamine group)、經取代或未經取代之芳香基(aryl group)、經取代或未經取代之茀基(fluorenyl group)、經取代或未經取代之咔唑基(carbazole group)、或經取代或未經取代之包含一個以上氮(N)、氧(O)、硫(S)與磷(P)原子雜環基(heteroring group);當p2或q2時,複數個L或Y係彼此相同或不同;R1與R3可以彼此鍵結以形成一個脂肪族環(aliphatic ring)、或一個芳香族環(aromatic ring)、或脂肪族雜環(aliphatic heteroring)、或芳香族雜環(aromatic heteroring),
或形成一螺旋鍵結(spiro bond);當o2時,複數個R4係彼此相同或不同;R4係一芳香基(aryl group),其中該取代基係選自由:經取代或未經取代之雜環基,其包含含一個以上O、S及P原子之五員環或六員環,經取代或未經取代之單環或多環的雜環基,其包含含有一個或多個N原子之六員環,經取代或未經取代之苯並咔唑基(benzocarbazole group)及一個經取代或未經取代之膦氧化物基所組成的群組;一經取代或未經取代之膦氧化物基;一經取代或未經取代之雜環基,其包含含有一個以上O、S及P原子之五員環或六員環;一經取代或未經取代之單環或多環的苯並咔唑基或一經取代或未經取代之單環或多環的雜環基,其包含含有一個以上N之六員環,或複數個R4中的相鄰基團可形成脂肪族環、芳香族環、脂肪族雜環、芳香族雜環或形成一螺旋鍵結,當r2,複數個R5係彼此相同或不同;R5為氫、氘、鹵基、腈基、硝基、氫氧基、經取代或未經取代之烷基、經取代或未經取代之環烷基;經取代或未經取代之烷氧基;經取代或未經取代之膦氧化物基;經取代或未經取代之芳氧基;經取代或未經取代之烷硫氧基;經取代或未經取代之芳硫氧基;經取代或未經取代之烷磺氧基;經取代或未經取代之芳磺氧基;經取代或未經取代之烯基;經取代或未經取代之矽烷基;經取代或未經取代之硼基;是經取代或未經取代之胺基;經取代或未經取代之烷胺基;經取代或未經取代之芳烷胺基;經取代或未經
取代之芳胺基;經取代或未經取代之雜芳胺基;經取代或未經取代之芳香基;經取代或未經取代之茀基;經取代或未經取代之咔唑基;或經取代或未經取代之包含一個以上N、O、S與P原子之雜環基,或複數個R5中相鄰取代基彼此鍵結形成脂肪族環、芳香族環、脂肪族雜環、芳香族雜環,或形成一螺旋鍵結。
此外,本發明提供一有機電子裝置,包含:一第一電極、一第二電極、及一層以上之有機材料層,其係位於第一電極與第二電極之間,其中,該一層以上之有機材料層包含化學式1之該熒蔥化合物。
依本發明所述,一種熒蔥衍生物可以用來當作有機電子裝置(包括有機發光裝置)之有機材料層,而且該包含利用該熒蔥衍生物的有機發光裝置之有機電子裝置,可提升效能、降低驅動電壓及/或改善壽命特性。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧發光層
4‧‧‧陰極
5‧‧‧電洞注入層
6‧‧‧電洞傳輸層
7‧‧‧電子傳輸層
圖1係一實施例之具有基板(1)、陽極(2)、發光層(3)、及陰極(4)之有機電子裝置示意圖。
圖2係一實施例之具有基板(1)、陽極(2)、電洞注入層(5)、電洞傳輸層(6)、發光層(3)、電子傳輸層(7)及陰極(4)之有機電子裝置示意圖。
本發明提供一種熒蔥化合物,係以化學式1表示。
此外,本發明中以化學式1表示之該化合物,可以下列化學式2表示:[化學式2]在化學式2中,
o、r與R3至R5的定義與在化學式1中的定義相同,每一n與m係0至5之一整數,當n2時,複數個R6係彼此相同或不同,當m2時,複數個R7係彼此相同或不同,R6與R7係彼此相同或不同,且各自獨立為氫;氘;鹵素;腈基;硝基;氫氧基;經取代或未經取代之烷基;一個經取代或未經取代之環烷基;經取代或未經取代之烷氧基;經取代或未經取代之膦氧化物基;經取代或未經取代之芳氧基;經取代或未經取代之烷硫氧基;經取代或未經取代之芳硫氧基;經取代或未經取代之烷磺氧基;經取代或未經取代之芳磺氧基;經取代或未經取代之烯基;經取代或未經取代之矽烷基;經取代或未經取代之硼基;是經取代或未經取代之胺基;經取代或未經取代之烷胺基;經
取代或未經取代之芳烷胺基;經取代或未經取代之芳胺基;經取代或未經取代之雜芳胺基;經取代或未經取代之芳香基;經取代或未經取代之茀基;經取代或未經取代之咔唑基或包含一個以上N、O、S與P原子之經取代或未經取代之雜環基,或者相鄰取代基彼此鍵結形成脂肪族環、芳香族環、脂肪族雜環、芳香雜環族,或者形成一螺旋鍵結。
取代基實例如下所述,但不限於此。
此外,本發明中所指「經取代或未經取代」之意思,係指用一個以上的取代基來取代,其中,該取代基係選自由氘、鹵素、烷基、烯基、烷氧基、環烷基、矽烷基、芳基烯基(arylalkenyl group)、芳香基、芳氧基、烷硫氧基、烷磺氧基、芳磺氧基、硼基、烷胺基、芳烷胺基、芳胺基、雜芳基、咔唑基、茀基、腈基、硝基、氫氧基、氰基(cyano)及包含一個以上氮(N)、氧(O)、硫(S)及磷(P)原子之雜環基,或者沒有取代基所組成的群組。
在本發明中,一種烷基係直鏈狀或支鏈狀,而且雖然沒有特別加以限制,但是碳數在1至50較佳,其特定實例,包括甲基、乙基、丙基、異丙基、丁基、叔丁基、戊基、己基、庚基等等,但不在此限。
在本發明中,烯基係直鏈狀或支鏈狀,而且雖然沒有特別加以限制,但是碳數在2至50較佳,其較佳特定實例,包括經一芳香基(例如:芪基(stylbenyl group)或苯乙烯基(styrenyl group))取代之烯基,但不限於此。
在本發明中,該烷氧基係直鏈狀或支鏈狀,而
且雖然沒有特別加以限制,但是碳數在1至50較佳。
在該化合物中,包含在化合物中的烷基、烯基與烷氧基的長度並不影響該化合物的共軛長度(conjugation length),而且只會在該化合物應用到有機電子裝置時,才伴隨地對該化合物的應用方法有影響,例如:應用在真空沉積(vacuum depostiion)法或溶液塗佈法,因此,碳原子的數目並不特別加以限制。
在本發明中,該環烷基沒有特別限制,不過,碳數在3至60較佳,其中,環戊基(cyclopentyl group)或環己基(cyclohexyl group)較佳。
在本發明中,該芳香基係單環或多環,而且雖然沒有特別加以限制,但是碳數在6至60較佳,其特定實例包括單環之芳香族基,例如:苯基(phenyl group)、聯苯基(biphenyl group)、聯三苯基(triphenyl group)、三苯基(terphenyl group);或均二苯乙烯基(stilbenyl group)及多環芳香族基,例如:萘基(naphthyl group)、聯萘基(binaphthyl group)、蒽基(anthracenyl group)、菲基(phenanthrenyl group)、芘基(pyrenyl group)、苝基(perylenyl group)、四苯基(tetracenyl group)、克萊辛基(crycenyl group)、茀基(fluorenyl group)、乙醯稠四苯基(acenaphthacenyl group)、聯三伸苯基(triphenylene group),或熒蒽基(fluoranthene group),但是不僅限於這些例子。
在本發明中,該雜環基係一包含氮(N)、氧(O)、硫(S)及磷(P)雜原子之雜環基,而且雖然沒有特別加以限制,
但是碳數在2至60較佳,其實例包括:塞吩基(thiophene group)、呋喃基(furan group)、吡咯基(pyrrole group)、咪唑基(imidazole group)、噻唑基(thiazole group)、噁唑基(oxazole group)、噁二唑基(oxadiazole group)、三唑基(triazole group)、吡啶基(pyridyl group)、雙吡啶基(bipyridyl group)、三氮雜苯基(triazine group)、吖啶基(acridyl group)、噠嗪基(pyridazine group)、喹諾酮基(qinolinyl group)、異喹啉基(isoquinoline group)、吲哚基(indole group)、咔唑基(carbazole group)、苯並噁唑基(benzoxazole group)、苯並咪唑基(benzimidazole group)、苯並噻唑基(benzothiazole group)、苯並咔唑基(benzocarbazole group)、苯並呋喃基(benzofuranyl group)、二苯並呋喃基(dibenzofuranyl group)等,但不限於此。
在本發明中,該包含一六員環(包含有一個以上N)之單環或多環之雜環基,其實例包括:吡啶基(pyridine group)、嘧啶基(pyrimidine group)、噠嗪基(pyridazine group)、吡嗪基(pyrazine group)、三氮雜苯基、四嗪基(tetrazine group)、異丙嗪基(pentazine group)、喹啉基(quinoline group)、賽諾啉基(cynoline group)、喹唑啉基(quinazoline group)、喹喔啉基(quinoxaline group)、吡啶並吡嗪基(pyridopyrazine group)、吡嗪並吡嗪基(pyrazinopyrazine group)、吡嗪並喹喔啉基(pyrazinoquinoxaline group)、吖啶基(acridine group)、啡啉基(phenanthroline group)等,但不限於此。
在本發明中,該包含一六員環(含有一個以上
N)之單環或多環雜環基係一包含至少一個或以上之六員環(包含有一個以上N)之雜環基,且也包含一含有一五員環與一六員環(包含一個以上之N)稠合之雜環基。換句話說,不同於前面描述之特定實例之其他五員環或六員環,可額外地被稠合,且該稠合之五員環或六員環可能是芳香族環、脂肪族環、脂肪族雜環及/或芳香族雜環。
在本發明中,該鹵基之實例,包括:氟、氯、溴或碘。
在本發明中,在該茀基(fluorenyl group)之結構中有兩個環狀有機化合物是透過一個原子來連接的,
例如:等。
在本發明中,該茀基包含一個開環的茀基結構,而且在該開環的茀基結構中,透過一個原子來連接兩個環狀化合物的結構中的一個環化合物的環是斷開的,
例如:等。
在本發明中,胺基的碳原子數目沒有特別限制,但是,碳數在1至50較佳。其特定實例包括:甲胺基(methylamine group)、二甲胺基(dimethylamine group)、乙胺基(ethylamine group)、二乙胺基(diethylamine group)、苯胺基(phenylamine group)、萘胺基(naphthylamine group)、聯苯
胺基(biphenylamine group)、蒽胺基(anthracenylamine group)、9-甲基蒽胺基9-methyl-anthracenylamine group)、二苯胺基(diphenylamine group)、苯基萘胺基(phenylnaphthylamine group)、二甲苯胺基(ditolylamine group)、苯基甲苯胺基(phenyltolylamine group)、三苯胺基(triphenylamine group)等,但不僅限於此。
在本發明中,該芳胺基的碳原子數目沒有特別限制,但是,碳數在6至50較佳。其實例,包括:經取代或未經取代的單環二芳基胺基(diarylamine)、經取代或未經取代的多環二芳基胺基,或經取代或未經取代的單環與多環的二芳基胺基。
在本發明中,該芳氧基、該芳硫氧基、該芳磺氧基與該芳烷胺基的碳原子的數目沒有特別限制,但是,數目在6至50較佳。在該芳氧基、該芳硫氧基、該芳磺氧基與該芳烷胺基中之芳香基與前述該芳香基之例子相同。
在本發明中,在該烷硫氧基、該烷磺氧基、該烷胺基與該芳烷胺基中之該烷基與前述的該烷基之例子相同。
在本發明中,在一種雜芳胺基中的該雜芳基會係從前述的雜環基之例子中選擇出來。
在本發明中,該亞芳基、該伸烯基、該茀烯基與該雜亞芳基各自是該芳香基、該烯基、該茀基與該雜芳基的二價基團。除了這些基團是二價的基團,有關於該芳香基、該烯基、該茀基與該雜芳基的敘述可適用於該亞芳
基、該伸烯基、該茀烯基與該雜亞芳基。
在本發明中,該經取代之亞芳基意指苯基、聯苯基、萘基、茀基、芘基、菲基、迫聯萘基(perylene group)、四苯基、蒽基等,經其他取代基取代。
在本發明中,該經取代之雜亞芳基意指吡啶基苯硫基(thiophenyl group)、三氮雜苯基、喹啉基、啡啉基、咪唑基、噻唑基、噁唑基、咔唑基與合併的雜環基,例如:苯並喹啉基(benzoquinoline group)、苯並咪唑基、苯噁唑基(benoxazole group)、苯並噻唑基、苯並咔唑基、二苯並噻吩(dibenzothiophenyl group)基等,經其他取代基取代。
在本發明中,相鄰取代基意指當有二個以上取代基時,每一個相鄰之取代基。
在本發明中,與一個相鄰的取代基形成脂肪族環、芳香族環、脂肪族雜環,或芳香族雜環意指每一個相鄰的取代基產生一個鍵結,形成一個五員至七員的多環或單環。
在本發明中,螺旋鍵結意指一種結構,在該結構中,二環狀有機化合物連接至一個原子,而且可包括透過一個原子來連接兩個環狀化合物的結構中的一個環狀化合物的連接是斷開的結構。
本發明提供一種新穎熒蔥化合物,以化學式1表示。該化合物基於其結構特性,可在有機電子裝置中用作有機材料層。
在本發明的一個實施例中,R1至R3基團以
-(L)p-(Y)q表示。
在本發明的一個實施例中,p為0至10之一整數。
在本發明的一個實施例中,p為1。
在本發明的一個實施例中,p為0。
在本發明的一個實施例中,q為1至10之一整數。
在本發明的一個實施例中,q為1。
在本發明的一個實施例中,L為經取代或未經取代之亞芳基、經取代或未經取代之茀烯基、經取代或未經取代之雜亞芳基。
在本發明的一個實施例中,L為經取代或未經取代之亞芳基。
在本發明的一個實施例中,L為經取代或未經取代之伸苯基(phenylene group)。
在本發明的一個實施例中,Y為氫。
在本發明的一個實施例中,R4係經取代或未經取代之苯並喹啉基、經取代或未經取代的啡啉基、經取代或未經取代的嘧啶基、經取代或未經取代的三氮雜苯基、經取代或未經取代之苯菲啶基(benzophenanthridine group)、經取代或未經取代之喹啉基、經取代或未經取代之咔唑基、經取代或未經取代之苯並咔唑基、經取代或未經取代之二苯並噻吩基(dibenzothiophene group)、經取代或未經取代之二苯並呋喃基、經取代或未經取代之膦氧化物基、經取代
或未經取代之苯並噻吩基(benzothiophene group)、經取代或未經取代之苯並呋喃基(benzofuran group)、經取代或未經取代之喹唑啉基。
在本發明的一個實施例中,R4藉由鍵結到相鄰之取代基而形成脂肪族環。
在本發明的一個實施例中,R4藉由鍵結到相鄰之取代基而形成芳香族環。
在本發明的一個實施例中,R4係經至少一下列取代基所取代之苯基、或為至少一下列取代基、或複數個相鄰的R4彼此形成經至少一下列取代基所取代之碳氫環。
*意指被連接到由化學式1、一苯基或複數個相鄰之R4彼此鍵結所形成的碳氫環上,該些取代基可為未經取代或經額外取代,其中,用來經額外取代之取代基係選自經取代或未經取代之烷基;經取代或未經取代之芳香基及經取代或未經取代包含一個以上氮(N)、氧(O)、硫(S)與磷(P)原子之雜環基。
在本發明的一個實施例中,該取代基係額外經氫、甲基(methyl group)、乙基(ethyl group)、苯基、萘基、聯苯基或吡啶基所取代。
在本發明的一個實施例中,該碳氫環係芳香族環、脂肪族環或脂肪族環與芳香族環之稠合環,且為單環或多環。
在該取代基中,「經取代」意指鍵結到一化合物碳原子之氫原子經其他原子或官能基所置換,且「取代基」包括全部的氫、其他原子與官能基。在本發明中,取代的位置沒有限制,只要它的位置是一個經氫原子取代之位置就行,也就是一可以經取代基取代之位置,而且,當有二或以上個取代時,該二或以上個取代基可為彼此相同或不同。
在本發明的一個實施例中,R4係經取代或未經取代之苯並喹啉基。
在本發明的一個實施例中,R4係經取代或未經取代之啡啉基。
在本發明的一個實施例中,R4係經取代或未經取代之嘧啶基。
在本發明的一個實施例中,R4係經一苯基取代之嘧啶基。
在本發明的一個實施例中,R4係經一聯苯基取代之嘧啶基。
在本發明的一個實施例中,R4係經取代或未經取代之三氮雜苯基。
在本發明的一個實施例中,R4係經一苯基取代之三氮雜苯基。
在本發明的一個實施例中,R4係經一萘基取代之三氮雜苯基。
在本發明的一個實施例中,R4係經取代或未經取代之苯菲啶基。
在本發明的一個實施例中,R4係經取代或未經取代之喹啉基。
在本發明的一個實施例中,R4係經一苯基取代之喹啉基。
在本發明的一個實施例中,R4係經一吡啶基取代之喹啉基。
在本發明的一個實施例中,R4係具有一菲啶基(phenanthridine group)與一苯並咪唑基鍵結在一起之結構之取代基。
在本發明的一個實施例中,R4係具有一喹啉基與一苯並咪唑基鍵結在一起之結構之取代基。
在本發明的一個實施例中,R4係經取代或未經取代之苯並咔唑基,該苯並咔唑基係
在本發明的一個實施例中,R4係一個經取代或未經取代的二苯並噻吩基,該二苯並噻吩基係連接到本發明化合物的熒蒽核心上,連接的位置是在下列二苯並噻吩基結構中的位置6或位置2。
在本發明的一個實施例中,R4係一個經取代或未經取代的二苯並呋喃基,該二苯並呋喃基係連接到本發明化合物的熒蒽核心上,連接的位置是在下列二苯並呋喃基結構中的位置6或位置2。
在本發明的一個實施例中,R4係經取代或未經取代之膦氧化物基。
在本發明的一個實施例中,R4係經一苯基取代之膦氧化物基。
在本發明的一個實施例中,R4係經取代或未經取代之苯並噻吩。
在本發明的一個實施例中,R4係經一苯基取代之苯並噻吩。
在本發明的一個實施例中,R4係經取代或未經取代之苯並呋喃。
在本發明的一個實施例中,R4係經一苯基取代之苯並呋喃。
在本發明的一個實施例中,R4係經取代或未經取代之喹唑啉基。
在本發明的一個實施例中,R4係經一苯基取代之喹唑啉基。
在本發明的一個實施例中,R4係經取代或未經取代之菲基(phenanthrene group)。
在本發明的一個實施例中,R4係經取代或未經取代之吡啶基。
在本發明的一個實施例中,R4係經一吡啶基取代之吡啶基。
本發明中所提及的化合物,較佳之特定實例包括下列化合物,但不僅限於這些例子。
在本發明的一個實施例中,R4係下列結構式中之任一個。
在本發明的一個實施例中,R4係下列結構式中的任一個。
在本發明的一個實施例中,化學式1係由下列化合物1平38中的任一個來表示。
藉由將熒蔥當作核心結構,而且加入不同之取代基,如化學式1所示。化學式1的化合物可具有適當的用於有機電子裝置之有機材料層的特性。
化合物的共軛長度與能帶差(energy band gap)有密切的關聯。具體說明,當共軛長度愈長,能帶差愈小。如前所述,化學式1的化合物核心共軛受限,因此,能帶差大。
在本發明的一個實施例中,具有不同能帶差值的化合物可藉由在該核心結構中R1至R7與R’的位置上加入不同的取代基來合成,其中,該核心結構如前所述,具有大的能帶差。基本上,藉由在該具有大的能帶差的核心結構上加入取代基來調整能帶差是簡單的,然而,當一個
核心結構具有小能帶差時,難以藉由加入取代基的方式,來大幅度調整能帶差。
此外,化合物的最高佔據分子軌域(HOMO)與最低未佔分子軌域(LUMO)能階,可以藉由在該核心結構的位置R1至R7與R’上加入不同的取代基來調整,其中,該核心結構具有前述之結構。
此外,藉由將不同取代基加到具有前述結構之核心結構上,就能夠合成具有該被加入取代基獨特特性之化合物。例如:將通常使用在電洞注入層材料、電洞傳輸層材料、發光層材料與電子傳輸層材料中之取代基加到該核心結構上,能合成出滿足各有機材料層所需條件之材料。
化學式1之化合物在核心結構中包含熒蔥化合物,因此,具有適合當作有機發光裝置中電洞注入及/或電子傳輸材料的能階。在本發明中,具有低驅動電壓與高發光效率之裝置能夠藉由選擇具有適當能階之化合物來獲得,而該化合物之適當能階取決於化學式1之化合物中的取代基,以及在有機發光裝置中利用該化合物。
此外,藉由將不同取代基加到核心結構,可以微調該化合物的能階差,而且同時改善有機材料間之介面特性,因此,這些材料能會有不同的應用。
同時,由於化學式1之化合物本身的高玻璃轉換溫度(Tg),使得該化合物具有優秀的熱穩定性,這種熱穩定性的增強係提供裝置的驅動穩定性的重要因素。
化學式1的化合物可由後續描述的製備例來製備。
本發明的化學式1的化合物,是由乙烷合萘醌(acenaphthenequinone)與經取代之丙酮(propanone)反應合成之化合物;使一取代基接到乙炔基苯(ethynyl benzene),再讓該乙炔基苯(ethynyl benzene)跟該被合成之化合物反應,就能夠得到化學式1之化合物。
另一種方式,是由乙烷合萘醌(acenaphthenequinone)與經取代之丙酮反應合成之化合物,然後,將不同取代基加到該熒蔥衍生物上,就能得到化學式1之化合物。
本發明還提供一種使用該熒蔥衍生物之有機電子裝置。
在本發明的一個實施例中,提供一種有機電子裝置,包含:一第一電極、一第二電極及一層以上之有機材料,其介於該第一電極與該第二電極之間,其中,該些有機材料層包含該熒蔥化合物。
該有機電子裝置可選自由有機發光裝置、有機太陽能電池與有機電晶體所組成之群組。
該有機電子裝置之該有機材料層,可做成單層結構,但是,也可以做成多層結構,其中將二層以上之有機材料層堆疊。例如:本發明之該有機發光裝置,可有包含電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層等之結構。然而,該有機發光裝置之結構不限於前
述的例子,而可以包含較少數目之有機材料層。
在本發明的另一實施例中,該有機電子裝置可為一般類型之有機電子裝置,其中,一陽極、一層以上之有機材料層及一陰極係依序地積層到一基板上。
在本發明的另一實施例中,該有機電子裝置係反轉類型之有機電子裝置,其中,一陰極、一層以上之有機材料層及一陽極係依序地積層到一基板上。
除了在一層以上之有機材料層中包含本發明之化合物(即熒蔥化合物),本發明的該有機電子裝置可利用在相關領域之材料與方法來製造。
例如:製造本發明之該有機電子裝置,可將一第一電極、一有機材料層及一第二電極依序地積層在一基板上。此時,利用物理氣相沉積(PVD)法,例如:濺鍍法或電子束蒸發法,將金屬、具有導電性的金屬氧化物或合金沉積在基板上,成形一陽極;成形一包含電洞注入層、電洞傳輸層、發光層、電子傳輸層之有機材料層,積層在該陽極上,然後,在其上沉積一可用來當作陰極的材料,來製造該有機電子裝置。除了這個方法之外,該有機電子裝置,可以藉由在一基板上連續沉積一陰極材料、一有機材料層及陽極材料來製造。
此外,當製造該有機電子裝置時,熒蔥化合物係利用溶液塗佈法與真空沉積法來形成一有機材料層。這裡所指的溶液塗佈法係指旋轉塗佈法、浸泡塗佈法、刮刀塗佈法、噴墨印刷法、網版印刷法、噴塗法,或類似方法,
但不限於前述例子。
在本發明的一個實施例中,該有機電子裝置可為有機發光裝置。
在本發明的一個實施例中,該有機發光裝置包括:一第一電極、一第二電極及一層以上包含介於該第一電極與該第二電極間之發光層之有機材料層,其中,該一層以上之有機材料層包含該熒蔥化合物。
在本發明的一個實施例中,該有機材料層,包括:電洞注入層、電洞傳輸層或電洞同時注入與傳輸層,而且該電洞注入層、該電洞傳輸層、或該電洞同時注入與傳輸層包含該熒蔥化合物。
在本發明的一個實施例中,該有機材料層,包括:電子傳輸層、電子注入層、或電子同時傳輸與注入層,而且該電子傳輸層、該電子注入層、或該電子同時注入與傳輸層包含該熒蔥化合物。
在本發明的一個實施例中,該發光層包含該熒蔥化合物。
在本發明的一個實施例中,該發光層包含該熒蔥化合物,作為該發光層之主發光體材料。
在本發明的一個實施例中,該發光層包含該熒蔥化合物,作為該發光層之主發光體材料,而且依據在一有機發光裝置中所需要之特性,在工業界中所屬相關技術領域已知的摻雜物中選擇一摻雜物。
在本發明的一個實施例中,該有機發光裝置進
一步包含一層以上之材料層,選自由電洞注入層、電洞傳輸層、電子傳輸層、電子注入層、電子阻障層與電洞阻障層所組成之群組。
在本發明的另一個實施例中,除了包含以化學式1表示之該熒蔥化合物之有機材料層,該有機發光裝置之該有機材料層可包含:包含芳胺基、咔唑基或苯並咔唑基化合物之一電洞注入層或電洞傳輸層。
在本發明的一個實施例中,該有機發光裝置係上發光型(top-emission type)、下發光型(bottom-emission type)或雙面發光型(dual-emission type),依所使用的材料來決定。
例如:在本發明之有機電子裝置的實施例中,該有機電子裝置之結構如圖1與圖2所示,但該結構不限於前述例子。
圖1說明一有機電子裝置之結構,其中,依序地堆疊一基板(1)、一陽極(2)、一發光層(3)及一陰極(4)。在此結構中,在該發光層(3)中可包含該熒蔥化合物。
圖2說明一有機電子裝置的結構,其中,依序地堆疊一基板(1)、一陽極(2)、一電洞注入層(5)、一電洞傳輸層(6)、一發光層(3)、一電子傳輸層(7)及一陰極(4)。在此結構中,在一層以上之該電洞注入層(5)、該電洞傳輸層(6)、該發光層(3)及該電子傳輸層(7)中可包含該熒蔥化合物。
在本發明的一個實施例中,該有機電子裝置係有機太陽能電池。
在本發明的一個實施例中,有機太陽能電池,包含:一第一電極、一第二電極及一層以上包含一介於該第一電極與該第二電極間之光活性層之有機材料層,其中,該一層以上之有機材料層包含該熒蔥化合物。
在本發明的一個實施例中,該有機材料層,包括:電子傳輸層、電子注入層或電子同時傳輸與注入層,而且該電子傳輸層、該電子注入層或該電子同時傳輸與注入層包含該熒蔥化合物。
在本發明的另一個實施例中,該光活性層包含該熒蔥化合物。
在本發明的另一個實施例中,該有機材料層,包含:一電子供體(electron donor)與一電子受體(electron acceptor),而且,該電子供體或該電子受體包含該熒蔥化合物。
在本發明的一個實施例中,當該有機太陽能電池接受到從外部光源來的光子之後,在該電子供體與該電子受體間產生電子與電洞,該產生的電洞通過電子供體層傳輸到陽極。
在本發明的一個實施例中,該有機太陽能電池進一步包含數層外加的有機材料層,該有機太陽能電池之該有機材料層,可以藉由使用同時具有數種功能之有機材料,來減少有機材料層的數目。
在本發明的一個實施例中,該有機電子裝置係有機電晶體。
在本發明的一個實施例中,有機電晶體,包含:一源極、一汲極、一閘極及一層以上包含該熒蔥化合物之有機材料層。
在本發明的一個實施例中,該有機電晶體包含一電荷產生層,其可含有該熒蔥化合物。
在本發明的另一個實施例中,該有機電晶體包含一絕緣層,其位於該基板與該閘極上。
當該有機電子裝置包含數層有機材料層時,該些有機材料層可由相同材料或不同材料所形成。
在本發明的一個實施例中,該第一電極是陰極,而且該第二電極是陽極。
在本發明的一個實施例中,該第一電極是陽極,而且該第二電極是陰極。
必要時,要考慮光學特性及物理性質來選擇該基板。例如:該基板較佳是透明的,不過,堅硬的材料也可用來當作該基板,該基板也可由可撓曲的材料所製成,例如:塑膠。
該基板之材料,除了玻璃和石英,包含:聚對苯二甲酸乙烯酯(PET)、聚萘二甲酸乙二酯(PEN)、聚丙烯(PP)、聚乙醯胺(PI)、聚碳酸酯(PC)、聚苯乙烯(PS)、聚縮醛(POM)、丙烯腈-苯乙烯(AS)共聚合物、丙烯腈-丁二烯-苯乙烯(ABS)共聚合物、三醋酸纖維素(TAC)、聚芳酯化合物(PAR)等,但不限於此。
用來當作陰極的材料,通常較佳需要具有小的
功函數(work function),使得電子順利注入到有機材料層。陰極材料之特定實例,包括:金屬,例如:鎂(magnesium)、鈣(calcium)、鈉(sodium)、鉀(potassium)、鈦(titanium)、銦(indium)、釔(yttrium)、鋰(lithium)、釓(gadolinium)、鋁(aluminum)、銀(silver)、錫(tin)、鉛(lead)或其合金;多層結構材料,例如:LiF/Al或LiO2/Al等,但不限於此。
用來當作陽極之材料,通常較佳需要具有大的功函數,使得電洞順利注入到有機材料層。可用於本發明之陽極材料之特定實例,包括:金屬,例如:釩(vanadium)、鉻(chromium)、銅(copper)、鋅(zinc)或金(gold)或其合金;金屬氧化物,例如:氧化鋅(zinc oxides)、銦氧化物(indium oxides)、銦錫氧化物(indium tin oxides)(ITO)、或銦鋅氧化物(indium zinc oxides)(IZO);金屬與氧化物之混合物,例如:ZnO:Al或SnO2:Sb;導電聚合物,例如:聚3-甲基塞吩(poly(3-methylthiophene))、聚3,4-乙烯-1,2-二氧基塞吩(PEDOT)、聚吡咯(polypyrrole)、與聚苯胺(polyaniline)等,但不限於此。
該電洞傳輸層係從電洞注入層接受電洞且將電洞傳輸到發光層之一層,而且電洞傳輸材料較佳為一種具有高電洞移動性(mobility),能夠從陽極或電洞注入層接受電洞、使電洞移動到發光層之材料。特定實例,包括:以芳胺類(arylamine-based)有機材料、導電聚合物、同時具有共軛部分(conjugated parts)與非共軛部分(non-conjugated parts)之段共聚合物(block copolymer)等,但不限於此。
該電洞注入層係從電極注入電洞之一層,而且,電洞注入材料較佳係具有能夠傳輸電洞的能力,因此,在陽極上產生電洞注入效果,及對發光層或發光材料具有優良的電洞注入效應,防止在發光層中產生之激發子(excitions)移動到電子注入層或電子注入材料,以及再加上具有優良的薄膜成形能力之化合物。該電洞注入材料之最高被佔據的分子軌域(HOMO)較佳係介於陽極功函數與周圍有機材料層HOMO間。該電洞注入材料特定實例,包括:金屬卟啉(porphyrin)、寡聚噻吩(oligothiophene)、芳胺類(arylamine-based)有機材料、酞花青(phthalocyanine)衍生物、己腈六氮雜聯伸三苯類(hexanitrile hexazatriphenylene-based)有機材料、喹吖酮類(quinacridone-based)導電聚合物、迫聯萘類(perylene-based)有機材料、蔥醌(anthraquinone)及聚苯胺與聚噻吩類(polyaniline-and polythiophene-based)導電聚合物等,但不限於此。
該發光材料係藉由從電洞傳輸層與電子傳輸層分別接收電洞與電子,使該電洞與該電子結合,能在可見光區發出光之材料,較佳材料為在螢光與磷光方面具有合適的量子效率。特定實例,包括:8-氫氧基喹啉鋁(8-hydroxy-quinoline aluminum)錯合物(Alq3);咔唑類(carbazole-based)化合物;二聚體化之苯乙烯基(dimerized styryl)化合物;BAlq;10-苯並喹啉金屬(10-hydroxybenzoquinoline-metal)化合物;苯並噁唑、苯並噻唑與苯並咪唑類(benzoxazole-benzthiazole-and
benzimidazole-based)化合物;聚對位苯基乙烯類(poly(p-phenylenevinylene),(PPV)-based)聚合物;螺旋化合物(spiro compound);聚芴(polyfluorene);紅螢烯(rubrene)等,但不限於此。
該發光層可包含主發光體材料與摻雜物材料。該主發光體材料,包括:稠合的芳香族環衍生物、含有雜環之化合物等。特別說明,該稠合的芳香族環衍生物,包括:蔥(anthracene)衍生物、芘(pyrene)衍生物、萘(naphthalene)衍生物、稠五苯(pentacene)衍生物、菲(phenathrene)化合物、熒蔥化合物等,而該含有雜環之化合物,包括:一咔唑衍生物、二苯並呋喃(dibenzofuran)衍生物、階梯狀呋喃(furan)化合物、嘧啶(pyrimidine)衍生物等,但不限於此。
該摻雜物材料,包含有機化合物、金屬或金屬化合物。
該摻雜物材料,包含:芳香胺(aromatic amine)衍生物、苯乙烯胺(styrylamine)化合物、硼(boron)錯合物、熒蔥化合物、金屬錯合物(metal complex)等。特別說明,當該稠合的芳香族環衍生物具有經取代或未經取代之芳胺基(arylamino group)時,該芳香胺衍生物,包括:含芳胺基的芘(arylamino-containing pyrene)、蔥、克萊辛(crycene)及二茚並芘(periflanthene);且該苯乙烯胺化合物,包括:一化合物,其中,經取代或未經取代之芳胺基係用至少一個芳基乙烯基(arylvinyl group)所取代,以及選自由芳香基(aryl group)、矽烷基(silyl group)、烷基(alkyl group)、環烷基
(cycloalkyl group)與芳胺基(arylamino group)所組成的群組之一個以上之取代基係經取代或未經取代。特別說明,該苯乙烯胺化合物,包括:苯乙烯胺、苯乙烯二胺(styryldiamine)、苯乙烯三胺(styryltriamine)、苯乙烯四胺(stylryltetramine)等,但不限於此。另外,該金屬錯合物,包括:一銥(iridium)錯合物、鉑(platinum)錯合物等,但不限於此。
該電子傳輸層係從電子注入層接收電子,而且將電子傳輸到發光層之一層,而合適的電子傳輸材料係一種具有高電子移動性、能夠從陰極接受電子、將電子移動到發光層之材料。其特定實例,包括:8-氫氧基喹啉之鋁錯合物、包含Alq3之錯合物、有機自由基化合物(organic radical compound)、氫氧基黃酮-金屬(hydroxyflavone-metal)錯合物等,但不限於此。根據相關領域中的技術,該電子傳輸層能跟任何一種所需的陰極材料一起使用。特別說明,該合適的陰極材料之實例為一般具有小功函數的材料,伴隨著為一鋁層或一銀層。該陰極材料,包括:銫(cesium)、鋇(barium)、鈣(calcium)、鐿(ytterbium)與釤(samarium),而且伴隨著一鋁層或一銀層。
該電子注入層係從電極注入電子之一層,而且電子注入材料較佳係具有傳輸電子能力、在陰極中具有電子注入效應與對一發光層或發光材料具有優良電子注入效應、防止在發光層中產生的激發子移動到電子注入層及優良薄膜成形能力之化合物,其特定實例,包括:芴酮
(fluorenone)、蒽醌二甲烷anthraquinodimethane、聯苯醌(diphenoquinone)、噻喃二氧化物(thiopyran dioxide)、噁唑(oxazole)、噁二唑(oxadiazole)、三唑(triazole)、咪唑(imidazole)、苝四羧酸(perylene tetracarboxylic acid)、亞茀基甲烷(fluorenylidene methane)、蔥酮(anthrone)等,與其衍生物、金屬錯合物、含氮的五員環衍生物等,但不限於此。
該金屬錯合物,包括:8-羥基喹啉鋰(8-hydroxyquinolinato lithium)、二(8-羥基喹啉)鋅(bis(8-hydroxyquinolinato)zinc)、二(8-羥基喹啉)銅(bis(8-hydroxyquinolinato)copper)、二(8-羥基喹啉)錳(bis(8-hydroxyquinolinato)manganese)、三(8-羥基喹啉)鋁(tris(8-hydroxyquinolinato)aluminum)、三(2-甲基-8-羥基喹啉)鋁(tris(2-methyl-8-hydroxyquinolinato)aluminum)、三(8-羥基喹啉)鎵(tris(8-hydroxyquinolinato)gallium)、二(10-羥苯甲基[h]喹啉)鈹(bis(10-hydroxybenzo[h]quinolinato)beryllium)、二(10-羥苯甲基[h]喹啉)鋅(bis(10-hydroxybenzo[h]quinolinato)zinc)、二(2-甲基-8-喹啉)氯化鎵(bis(2-methyl-8-quinolinato)chlorogallium)、二(2-甲基-8-喹啉)(鄰-甲酚)鎵(bis(2-methyl-8-quinolinato)(o-cresolato)gallium)、二(2-甲基-8-喹啉)(1-萘酚)鋁(bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum)、二(2-甲基-8-喹啉)(2-萘酚)鎵
(bis(2-methyl-8-quinolinato)(2-naphtholato)gallium)等,但不限於此。
該電洞阻障層係阻擋電洞到達陰極的一層,且一般而言,與該電洞注入層在相同的條件下成形。其特定實例,包括:噁二唑衍生物、三唑衍生物、啡啉(phenanthroline)衍生物、BCP、鋁錯合物等,但不限於此。
該電子阻障層係藉由阻擋電子的同時,接收電洞,改善電子-電洞再結合的機率之一層,而且具有電洞傳輸能力並具有極低電子傳輸能力之材料才合適。作為電子阻障層之材料,必要時可使用上述電洞傳輸層材料,但不限於前述材料,也可使用已知之電子阻障層材料。
本發明中的該有機電子裝置,依據所使用的材料,可為上發光型、下發光型或雙面發光型。
以下詳細敘述製備化學式1之製備方法及包含化學式1之有機發光裝置之製程,以資參考。然而,下列的例子僅作為說明之用,並不限制本發明的範圍。
製備例
(1)化合物A-1的製備
在乙醇(600ml)中置入乙烷合萘醌(acenaphthenequinone)(30g,164mmol)與1,3-二苯基2-丙酮(1,3-diphenyl-2-propanone)(34g,164mmol),然後加入氫氧化鉀(KOH)(27.6g,492mmol),讓此混合物在85℃,攪拌回流(reflux)48小時,接著讓溫度降回到室溫,將300ml的水加入該混合物中,過濾出固體產物,並且加以乾燥,可得到化合物A-1(45g,產率77%),MS:[M+H]+=357
(2)化合物A-2的製備
在二甲苯(xylene)(500mL)中置入化合物A-1(30g,84.2mmol)與1-溴-4-乙炔苯(1-bromo-4-ethynylbenzene)(16.8g,92.8mmol),然後將該混合物在140℃,攪拌回流48小時,接著讓溫度降回到室溫,將300ml的乙醇加入該混合物中,
過濾出固體產物,並且加以乾燥,可得到化合物A-2(31.3g,產率74%),MS:[M+H]+=510
(3)化合物A-3的製備
在二甲苯(xylene)(500mL)中置入化合物A-1(30g,84.2mmol)與1-溴-4-乙炔苯(1-bromo-4-ethynylbenzene)(16.8g,92.8mmol),然後將該混合物在140℃,攪拌回流48小時,接著讓溫度降回到室溫,將300ml的乙醇加入該混合物中,過濾出固體產物,並且加以乾燥,可得到化合物A-2(29.7g,產率69%),MS:[M+H]+=510
(4)化合物B-1的製備
在乙醇(300ml)中置入乙烷合萘醌(6.9g,38mmol)與1,3-二(4-溴苯基)丙-2-酮(1,3-bis(4-bromophenyl)propan-2-one)
(14g,38mmol),然後加入氫氧化鉀(KOH)(6.4g,114mmol),讓此混合物在85℃,攪拌回流48小時,接著讓溫度降回到室溫,將200ml的水加入該混合物中,過濾出固體產物,並且加以乾燥,可得到化合物B-1(17.3g,產率88%),MS:[M+H]+=515
(5)化合物B-2的製備
在二甲苯(xylene)(200mL)中加入化合物B-1(17.3g,33.6mmol)與乙炔苯(ethynylbenzene)(4.1g,40.3mmol),然後將該混合物在140℃,攪拌回流48小時,接著讓溫度降回到室溫,將200ml的乙醇加入該混合物中,過濾出固體產物,並且加以乾燥,可得到化合物B-2(14.3g,產率72%),MS:[M+H]+=589
(6)化合物C-1的製備
在二氧陸圜(dioxane)(300mL)中加入化合物A-2(30g,58.9mmol)與雙戊酰二硼(bis(pinacolato)diboron)(16.5g,64.8mmol),然後加入醋酸鉀(potassium acetate)(17.3g,177mmol),接著再加入Pd(dppf)Cl2CH2Cl2(0.96g,2mol%),然後將該混合物攪拌回流6小時,接著讓溫度降回到室溫,將該混合物過濾得到濾液。將該濾液(filtrate)以真空蒸餾及溶於氯仿(chloroform)後,利用乙醇將該處理過的產物再結晶,然後過濾及乾燥,可得到化合物C-1(27.2g,產率83%),MS:[M+H]+=557
(7)化合物C-2的製備
在二氧陸圜(dioxane)(300mL)中加入化合物A-3(30g,58.9mmol)與雙戊酰二硼(16.5g,64.8mmol),然後加入醋酸鉀(17.3g,177mmol),接著再加入Pd(dppf)Cl2CH2Cl2(0.96g,2mol%),然後將該混合物攪拌回流6小時,接著讓溫度降回到室溫,將該混合物過濾得到濾液。將該濾液(filtrate)以真空蒸餾及溶於氯仿(chloroform)後,利用乙醇將該處理過的產物再結晶,然後過濾及乾燥,可得到化合物C-2(26.2g,產率80%),MS:[M+H]+=557
實施例
實施例1:化合物2的製備
在四氫呋喃(tetrahydrofuran)(THF)(200mL)中加入化合物C-1(17.6g,31.6mmol)與2-溴-1,10-啡啉(2-bromo-1,10-phenanthroline)(8.2g,31.6mmol)後,先加入2M的碳酸鉀(potassium carbonate)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物2(16.5g,產率86%),MS:[M+H]+=609
實施例2:化合物6的製備
在四氫呋喃(THF)(200mL)中加入化合物C-1(17.6g,31.6mmol)與2-氯-4,6-二苯基嘧啶(2-chloro-4,6-diphenylpyrimidine)(8.4g,31.6mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物6(15.6g,產率75%),MS:[M+H]+=661
實施例3:化合物7的製備
在四氫呋喃(THF)(200mL)中加入化合物C-1(17.6g,31.6mmol)與4-氯-2,6-二苯基嘧啶(4-chloro-2,6-diphenylpyrimidine)(8.4g,31.6mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物7(14.6g,產率70%),MS:[M+H]+=661
實施例4:化合物8的製備
在四氫呋喃(THF)(200mL)中加入化合物C-1(17.6g,31.6mmol)與2-氯-4,6-二苯基-1,3,5-三氮雜苯(2-chloro-4,6-diphenyl-1,3,5-triazine)(8.4g,31.6mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物8(16.1g,產率77%),MS:[M+H]+=662
實施例5:化合物26的製備
在四氫呋喃(THF)(200mL)中加入化合物A-2(15g,29.4mmol)與4-二苯並噻吩硼酸(4-dibenzothiophene boronic acid)(6.7g,29.4mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物26(12.6g,產率70%),MS:[M+H]+=613
實施例6:化合物27的製備
在四氫呋喃(THF)(200mL)中加入化合物A-2(15g,29.4mmol)與4-二苯並呋喃硼酸(4-dibenzofuran boronic acid)(6.2g,29.4mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物27(13.5g,產率77%),MS:[M+H]+=597
實施例7:化合物11的製備
在四氫呋喃(THF)(200mL)中加入化合物C-2(15g,26.8mmol)與2-氯-4,6-二苯基-1,3,5-三氮雜苯(8.4g,31.6mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.67g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物11(13.3g,產率75%),MS:[M+H]+=661
實施例8:化合物24的製備
在甲苯(toluene)(150mL)中加入化合物A-2(15g,29.5mmol)與11H-苯並[α]咔唑(11H-benzo[a]carbazole)(6.4g,
29.5mmol)後,先加入四丁氧基鈉(sodium tetrabutoxide)(NaOtBu)(15g),再加入Pd(PtBu4)2(0.16g,1mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物24(11.4g,產率60%),MS:[M+H]+=645
實施例9:化合物32的製備
在四氫呋喃(THF)(200mL)中加入化合物C-1(18g,32.4mmol)與(4-溴苯基)二苯基氧化膦((4-bromophenyl)diphenylphosphineoxide)(11.6g,32.4mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.75g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物32(13.7g,產率64%),MS:[M+H]+=706
實施例10:化合物38的製備
在四氫呋喃(THF)(200mL)中加入化合物C-1(15.0g,27.0mmol)與4’-(4-溴苯基)-2,2’:6’,2”-三吡啶(4’-(4-bromophenyl)-2,2’:6’,2”-terpyridine)(10.5g,27.0mmol)後,先加入2M的碳酸鉀(K2CO3)水溶液(100mL),再加入Pd(PPh3)4(0.62g,2mol%),然後將該混合物攪拌回流4小時,接著讓溫度降回到室溫,過濾出固體產物,然後利用氯仿與乙醇,將該固體產物再結晶,然後過濾及乾燥,可得到化合物38(15.5g,產率78%),MS:[M+H]+=737
實驗例:製造有機發光裝置及量測其特性
實驗例1-1
將一玻璃基板置入溶有清潔劑的蒸餾水中,以超音震盪清潔,其中,該玻璃基板上覆蓋一層膜厚500埃(Å)的銦錫氧化物(ITO),此時,使用一項費歇爾公司(Fischer Corporation)的產品當作該清潔劑,該蒸餾水經密理博公司(Millipore Corporation)所生產的過濾器過濾兩次。在該ITO
玻璃基板清洗30分鐘之後,再以蒸餾水進行超音波清洗10分鐘,重複兩次,在蒸餾水清洗完畢之後,使用一異丙醇、丙酮與甲醇的溶劑,進行超音波清洗,接著,將該玻璃基板乾燥,然後送到電漿清洗機中,以氧氣電漿清洗5分鐘,再送到真空沉積裝置(vacuum deposition apparatus)中。
將己腈六氮雜聯伸三苯(HAT),化學式為
,以真空熱沉積(thermal vacuum depositing)
的方式,在上述製備的該透明ITO電極上,形成一層厚度100埃的電洞注入層。
在該電洞注入層上,將4-4’-雙[N-(1-萘基)-N-苯胺基]聯苯(4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl)(NPB),化學式為
,以真空沉積的方式,形成一層厚
度1000埃的電洞傳輸層。
接著,將下列GH,化學為與
GD,化學式為,使用重量比10:1之GH與GD,
以真空沉積的方式,在該電洞傳輸層上,形成一膜厚230埃的發光層。
將化合物2,以真空沉積的方式,在該發光層上,形成一膜厚350埃的電子注入與傳輸層。
在該電子注入與傳輸層上,依序地沉積厚度15埃之氟化鋰(LiF)及厚度2000埃之鋁,形成一陰極。
在上述的製程中,該有機材料的沉積速率維持在0.4至0.7埃/秒(Å/sec)、該陰極的該氟化鋰的沉積速率是0.3埃/秒、該鋁的沉積速率是2埃/秒,進行沉積時的真空度維持在2x10-7至5x10-8托(torr),以此方式,製造出該有機發光裝置。
實驗例1-2
除了將實驗例1-1的化合物2換成化合物8外,該有機發光裝置是使用與實驗例1-1相同的方法來製造。
實驗例1-3
除了將實驗例1-1的化合物2換成化合物11外,該有機發光裝置是使用與實驗例1-1相同的方法來製造。
實驗例1-4
除了將實驗例1-1的化合物2換成化合物32外,該有機發光裝置是使用與實驗例1-1相同的方法來製造。
實驗例1-5
除了將實驗例1-1的化合物2換成化合物38外,該有機發光裝置是使用與實驗例1-1相同的方法來製造。
比較例1
除了將實驗例1-1的化合物2換成下列化學式
(ET-B)之化合物外,該有機發光裝置是使
用與實驗例1-1相同的方法來製造。
當施加電流(10mA/cm2)到由實驗例1-1至實驗例1-5,以及比較例1的該有機發光裝置時,可以得到如下表一的結果。
實驗例2-1
將己腈六氮雜聯伸三苯(HAT),化學式如前所示,以真空熱沉積的方式,在實驗例1-1中所製備的透明ITO電極上,形成一膜厚100埃的電洞注入層。
將4-4’-雙[N-(1-萘基)-N-苯胺基]聯苯(NPB)(膜厚700埃)、己腈六氮雜聯伸三苯(HAT)(膜厚50埃)與4-4’-雙[N-(1-萘基)-N-苯胺基]聯苯(NPB)(膜厚700埃),依序地以真空沉積的方式,在該電洞注入層上形成一電洞傳輸層。
接著,將下列BH,化學式為與BD,
化學式為,使用重量比25:1之BH與BD,
以真空沉積的方式,在該電洞傳輸層上形成一膜厚200埃的發光層。
將化合物7與喹啉鋰(lithium quinolate)(LiQ),
化學式,使用重量比1:1之化合物7與LiQ,以真
空沉積的方式,在該發光層上,形成一膜厚300埃的電子注入與傳輸層。
依序地將厚度15埃的氟化鋰(LiF)及2000埃的鋁,沉積在該電子注入與傳輸層上,形成一陰極。
在上述的製程中,該有機材料的沉積速率維持在0.4至0.7埃/秒(Å/sec)、該陰極的該氟化鋰的沉積速率是0.3埃/秒、該鋁的沉積速率是2埃/秒,進行沉積時的真空度維持在2x10-7至5x10-8托(torr),以此方式,製造出該有機發光裝置。
實驗例2-2
除了將實驗例2-1的化合物7換成化合物2外,該有機發光裝置是使用與實驗例2-1相同的方法來製造。
實驗例2-3
除了將實驗例2-1的化合物7換成化合物27外,該有機發光裝置是使用與實驗例2-1相同的方法來製造。
實驗例2-4
除了將實驗例2-1的化合物7換成化合物38之外,該有機發光裝置是使用與實驗例2-1相同的方法來製造。
比較例2
除了將實驗例2-1的化合物7換成下列化學式
(ET-C)的化合物之外,該有機發光裝置是
使用與實驗例2-1相同的方法來製造。
當施加電流(10mA/cm2)到由實驗例2-1至2-4,以及比較例2的該有機發光裝置時,可以得到如下表二的結果。
由表二可知,本發明的該新穎化合物能被用來當作有機材料層的材料,該有機材料層是用於包含有機發光裝置的有機電子裝置中,而且,包含有機發光裝置的有機電子裝置,其中,該有機發光裝置使用該新穎化合物,在效率、驅動電壓、穩定性等方面,表現出良好的特性。特別是本發明的該新穎化合物,具有優良的熱穩定性、深的HOMO能階與電洞穩定性,因而表現出優良的特性。該新穎化合物能被單獨地使用,或與n型摻雜物(如LiQ)混合後使用在有機電子裝置包含之有機發光裝置中。因為本發明的該新穎化合物的熱穩定性,該化合物改善了效率與裝置的穩定性。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧發光層
4‧‧‧陰極
Claims (15)
- 一種熒蔥化合物,如以下化學式1所示:[化學式1]
- 如申請專利範圍第1項所述之熒蔥化合物,其如以下化學式2所示:
- 如申請專利範圍第1項所述之熒蔥化合物,其中,R4係經至少一下列取代基所取代之一苯基;或係至少一下列取代基,或複數個相鄰R4彼此形成一碳氫環,其中該碳氫環係經至少一下列取代基所取代:
- 如申請專利範圍第3項所述之熒蔥化合物,其中,該些取代基更以氫、甲基、乙基、苯基、萘基(naphthyl group)、聯苯基(biphenyl group)或吡啶基(pyridine group)所取代。
- 如申請專利範圍第1項所述之熒蔥化合物,其中化 學式1為以下化合物1至38之任一者所示:
- 一種有機電子裝置,包含一第一電極;一第二電極;以及一或多層有機材料層,係設置於該第一電極與該第二電極間,其中一或多層該有機材料層包含申請專利範圍第1至5項中任一項所述之之熒蔥化合物。
- 如申請專利範圍第6項所述之有機電子裝置,其係選自由:有機發光裝置、有機太陽能電池以及機電晶體中所組成之群組。
- 如申請專利範圍第6項所述之有機電子裝置,其中,該有機電子裝置係一有機發光裝置,包含:一第一電極;一第二電極;以及一或多層有機材料層,其包括一發光層,係設置於該第一電極與該第二電極間,其中,一或多層該有機材料層含有該熒蔥化合物。
- 如申請專利範圍第8項所述之有機電子裝置,其中,該有機材料層包括一電子傳輸層、一電子注入層或一電子注入及傳輸層,該電子傳輸層、該電子注入層或該電子注入及傳輸層同時含有該熒蔥化合物。
- 如申請專利範圍第8項所述之有機電子裝置,其中,該發光層包含該熒蔥化合物。
- 如申請專利範圍第8項所述之有機電子裝置,其中,該有機材料層包括一電洞傳輸層或一電洞注入層,且該電洞傳輸層或該電洞注入層包含該熒蔥化合物。
- 如申請專利範圍第8項所述之有機電子裝置,其中,該有機材料層包含一層或兩層或兩層以上選自由:該電洞注入層、該電洞傳輸層、該電子傳輸層、該電子注入層、一電子阻障層以及一電洞阻障層所組成的群組。
- 如申請專利範圍第6項所述之有機電子裝置,其中,該有機電子裝置係一太陽能電池,包含: 一第一電極;一第二電極;以及一或多層有機材料層,包含:一光活性層介於該第一電極與該第二電極之間,其中,該有機材料層包含該熒蔥化合物。
- 如申請專利範圍第13項所述之有機電子裝置,其中,該有機材料層包含一光活化(photoactive)層,而且該光活化層包含該熒蔥化合物。
- 如申請專利範圍第6項之有機電子裝置,其中,該有機電子裝置係一有機電晶體,包含:一源極;一汲極;一閘極;以及一或多層有機材料層,其中,該有機材料層包含該熒蔥化合物。
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EP2924020A4 (en) | 2016-06-15 |
EP2924020A1 (en) | 2015-09-30 |
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TWI610920B (zh) | 2018-01-11 |
KR101775188B1 (ko) | 2017-09-05 |
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KR101739612B1 (ko) | 2017-05-24 |
KR20140065345A (ko) | 2014-05-29 |
JP6158937B2 (ja) | 2017-07-05 |
WO2014081168A1 (ko) | 2014-05-30 |
US10680182B2 (en) | 2020-06-09 |
CN104703969A (zh) | 2015-06-10 |
EP2924020B1 (en) | 2019-01-16 |
US20150236273A1 (en) | 2015-08-20 |
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