JPWO2005112520A1 - 発光素子 - Google Patents
発光素子 Download PDFInfo
- Publication number
- JPWO2005112520A1 JPWO2005112520A1 JP2006513616A JP2006513616A JPWO2005112520A1 JP WO2005112520 A1 JPWO2005112520 A1 JP WO2005112520A1 JP 2006513616 A JP2006513616 A JP 2006513616A JP 2006513616 A JP2006513616 A JP 2006513616A JP WO2005112520 A1 JPWO2005112520 A1 JP WO2005112520A1
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- Japan
- Prior art keywords
- group
- ring
- atom
- light emitting
- substituent
- Prior art date
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- Granted
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- 239000000463 material Substances 0.000 claims abstract description 170
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 107
- 125000001424 substituent group Chemical group 0.000 claims abstract description 93
- 125000003118 aryl group Chemical group 0.000 claims abstract description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 71
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 41
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 28
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 26
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 24
- 239000000470 constituent Substances 0.000 claims abstract description 21
- 125000004429 atom Chemical group 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229910052697 platinum Inorganic materials 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 239000003446 ligand Substances 0.000 claims description 19
- 125000004986 diarylamino group Chemical group 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- 150000003624 transition metals Chemical group 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 36
- 239000011365 complex material Substances 0.000 abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- -1 aromatic amine compound Chemical class 0.000 description 209
- 239000010410 layer Substances 0.000 description 95
- 238000000034 method Methods 0.000 description 52
- 0 C*(C)CC1NCC1 Chemical compound C*(C)CC1NCC1 0.000 description 44
- 125000003277 amino group Chemical group 0.000 description 36
- 125000003710 aryl alkyl group Chemical group 0.000 description 34
- 230000000052 comparative effect Effects 0.000 description 26
- 125000001931 aliphatic group Chemical group 0.000 description 25
- 238000010549 co-Evaporation Methods 0.000 description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 19
- 125000005842 heteroatom Chemical group 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- 125000002252 acyl group Chemical group 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- 125000003367 polycyclic group Chemical group 0.000 description 14
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 13
- 238000000576 coating method Methods 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000004423 acyloxy group Chemical group 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 8
- 125000005110 aryl thio group Chemical group 0.000 description 8
- 125000005368 heteroarylthio group Chemical group 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 150000003058 platinum compounds Chemical class 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 5
- 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 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000003963 dichloro group Chemical group Cl* 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoric acid amide group Chemical group P(N)(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 description 4
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 125000000400 lauroyl group Chemical group O=C([*])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 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 4
- 150000003057 platinum Chemical class 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 description 4
- 125000005106 triarylsilyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- PFMTUGNLBQSHQC-UHFFFAOYSA-N 4,5-diazafluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CN=C3C2=N1 PFMTUGNLBQSHQC-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
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- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
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- 238000003618 dip coating Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
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- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
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- 230000005283 ground state Effects 0.000 description 3
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 3
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- 150000002503 iridium Chemical class 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
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- 125000003696 stearoyl group Chemical group O=C([*])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 3
- 238000000859 sublimation Methods 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
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- 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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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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Abstract
Description
1.発光層内での電子・ホールの輸送
2.ホストの励起子生成
3.ホスト分子間の励起エネルギー伝達
4.ホストからゲストへの励起エネルギー移動
5.ゲストの三重項励起子生成
6.ゲストの三重項励起子から基底状態時の燐光発光
[1] 対向した電極間に2成分以上の材料で構成された発光層を有する有機発光素子において、該発光層の主構成材料が金属錯体であり、かつ副構成材料が燐光発光性発光材料である発光素子。
[2] 前記燐光発光性発光材料が白金又はイリジウム金属を有する材料である上記[1]に記載の発光素子。
[8] 前記発光性有機金属錯体が燐光発光性金属錯体である[7]に記載の発光素子。
本発明の有機発光素子の発光層では、ゲスト材料として燐光発光性発光材料が用いられる。燐光発光性発光材料としては、好ましくは遷移金属を有する燐光発光性発光材料であり、より好ましくは白金又はイリジウムを有する燐光発光性発光材料である。白金を有する燐光発光性発光材料としては、例えば、下記一般式(1)で示される白金錯体が挙げられる。
一般式(7)で表される白金錯体は、種々の手法で合成できる。例えば、配位子と白金化合物(錯体前駆体)を適当な溶媒及び適当な塩基の存在下、必要に応じ不活性ガス雰囲気下で反応させることにより容易に得ることができる。不活性ガスとしては、窒素ガス、アルゴンガス等が挙げられる。
前記錯体前駆体としては、無機及び有機白金化合物の何れも用いることができ、好ましい無機白金化合物としては、塩化白金、臭化白金及びヨウ化白金等の白金ハロゲン化物、塩化白金酸ナトリウム、塩化白金酸カリウム、臭化白金酸カリウム及びヨウ化白金酸カリウム等のハロゲン化白金酸塩が挙げられる。塩化白金及び塩化白金酸カリウムが、入手の容易さ等からより好ましく用いられる。
前記イリジウム錯体は、例えば、M.Nonoyama,Bull.Chem.Soc.Jpn.,1974,47(3),767−768に記載の方法などにより得られる。すなわち、理論量の2−フェニルピリジン等の配位子と塩化イリジウム水和物を反応させ、次いで塩基の存在下にアセチルアセトンと反応させてアセチルアセトナート錯体に誘導し、これをグリセロール中で理論量の配位子と反応させることにより得られる。
発光層のホスト材料である金属錯体は典型元素、遷移元素又はランタノイド系元素から選ばれる金属元素と配位子から形成される金属錯体が挙げられる。この金属錯体は中性金属錯体もしくはイオン性金属錯体であってもかまわないが、中性金属錯体であることが好ましい。さらに好ましくは発光性を有する金属錯体であり、さらに好ましくは燐光発光性を有する金属錯体であることが好ましい。燐光発光性を有する金属錯体とは、結晶中、固体中又は溶液中、室温又は低温において燐光発光する金属錯体を示す。
デジタルソースメータ:ケースレーインスツルメンツ社製 2400
色彩色度(輝度)計:ミノルタ製 CS−100
発光スペクトル測定装置:オーシャンオプティクス社製 分光蛍光計USB2000
素子構成として、図1に示す有機層が4層の素子を使用した。ITO基板上に、以下の有機層と電極層を10−4Paの真空チャンバー内で抵抗加熱による真空蒸着し、連続製膜した。
有機層1(ホール輸送層)(40nm):α−NPD
有機層2(発光層)(35nm):所定のホスト/所定のゲスト
有機層3(ブロッキング層)(10nm)BCP(バソクプロイン)
有機層4(電子輸送層)(35nm):Alq3
電極層1(0.5nm):LiF
電極層2(100nm):Al
例示化合物(E−3)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2時の駆動電圧は、7.25Vであった。また、100cd/m2時のCIE色度と発光ピークは、x=0.649、y=0.350、614nmであった。100cd/m2での外部量子効率(QE)は10.5%、パワー効率6.7lm/W、輝度−電流効率は15.4cd/Aであった。最高外部量子効率は11.1%であった。最高輝度は23,620cd/m2であった。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2での外部量子効率(QE)は9.0%、パワー効率8.3lm/W、輝度−電流効率は11.9cd/A、駆動電圧は4.5Vであった。100cd/m2での駆動電圧は、比較例1よりも約2.7V低電圧化した。また、100cd/m2時のCIE色度と発光ピークは、x=0.651、y=0.349、620nmであった。最高外部量子効率は9.1%であった。最高輝度は22,760cd/m2(10.8V、568mA/cm2、3.0%QE)であった。
例示化合物(E−5)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2時の駆動電圧は、7.39Vであった。
例示化合物(E−5)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2での外部量子効率(QE)は10.4%、パワー効率8.7lm/W、輝度−電流効率は14.3cd/A、駆動電圧は5.15Vであった。また、100cd/m2時のCIE色度と発光ピークは、x=0.649、y=0.350、622nmであった。100cd/m2での駆動電圧は、比較例2よりも約2V低電圧化した。発光閾値(1cd/m2)は2.68V、最高外部量子効率は10.6%、最高輝度は34,730cd/m2(13V、569mA/cm2、4.4%QE)であった。
例示化合物(E−3)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子の半減寿命を評価した(図2)。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子の半減寿命を評価した(図2)。初期輝度1500cd/m2、電流密度14.55mA/cm2、定電流DC駆動で282時間通電したところ、輝度は864.8cd/m2(対初期輝度57.65%)であった。駆動電圧は半減寿命に近づいてきた時でも11から12V程度で電圧の上昇が抑えられた。色度座標は変化が見られなかった。
この結果から、本実施例の素子は、例示化合物(E−3)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子(比較例3)と比較して寿命が長くなることが明らかとなった(図2)。
例示化合物(1−11)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2時の駆動電圧は10.40Vであった。100cd/m2時のCIE色度と発光ピークは、x=0.639、y=0.357、630nmであった。100cd/m2での外部量子効率(QE)は3.1%、パワー効率1.3lm/W、輝度−電流効率は4.1cd/Aであった。最高外部量子効率は3.3%であった。最高輝度は15270cd/m2(駆動電圧17.5V、電流639mA/cm2、外部量子効率1.8%)であった。
例示化合物(1−11)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2での外部量子効率(QE)は3.8%、パワー効率3.1lm/W、輝度−電流効率は5.0cd/A、駆動電圧は5.0Vであった。100cd/m2での駆動電圧は、比較例4よりも約5.4V低電圧化した。また、100cd/m2時のCIE色度と発光ピークはx=0.645、y=0.355、627nmであった。最高外部量子効率は4.6%であった。最高輝度は11,110cd/m2(駆動電圧11.5V、電流990mA/cm2、外部量子効率0.85%)であった。
例示化合物(1−101)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2時の外部量子効率(QE)は3.4%、駆動電圧は12.03Vであった。
例示化合物(1−101)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。この素子の100cd/m2での外部量子効率(QE)は5.9%、パワー効率3.2lm/W、輝度−電流効率は6.3cd/A、駆動電圧は6.17Vであった。また、100cd/m2時のCIE色度と発光ピークは、x=0.673、y=0.326、618nmであった。100cd/m2での駆動電圧は、比較例5よりも約5.8V低電圧化した。また、外部量子効率は2.5%高くなった。発光閾値(1cd/m2)は2.94V、最高外部量子効率は6.2%、最高輝度は8,198cd/m2(駆動電圧12.3V、電流586mA/cm2、外部量子効率1.3%)であった。
比較例4と同様に例示化合物(1−11)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子の半減寿命を評価した。初期輝度1,500cd/m2、電流密度62.5mA/cm2、定電流DC駆動での輝度半減期は3.2時間であった(図3)。
実施例4と同様に例示化合物(1−11)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子の半減寿命を評価した(図3)。初期輝度1,500cd/m2、電流密度68.2mA/cm2、定電流DC駆動での輝度半減期は184.2時間であった(図3)。例示化合物(1−11)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した素子(比較例6)と比較して寿命が長くなることが明らかとなった(図3)。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−29)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は7.7%、パワー効率5.0lm/W、輝度−電流効率は9.7cd/A、駆動電圧は6.2Vであった。100cd/m2での駆動電圧は、比較例1よりも約1.1V低電圧化した。100cd/m2時のCIE色度と発光ピークはx=0.637、y=0.363、619nmであった。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−30)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は7.0%、パワー効率5.4lm/W、輝度−電流効率は8.5cd/A、駆動電圧は5.0Vであった。100cd/m2での駆動電圧は、比較例1よりも約2.3V低電圧化した。100cd/m2時のCIE色度と発光ピークはx=0.639、y=0.361、619nmであった。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−32)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は4.5%、パワー効率3.5lm/W、輝度−電流効率は5.7cd/A、駆動電圧は5.1Vであった。100cd/m2での駆動電圧は、比較例1よりも約2.2V低電圧化した。100cd/m2時のCIE色度と発光ピークはx=0.635、y=0.365、621nmであった。
例示化合物(E−3)をゲスト材料として、ホスト材料(4−34)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は6.7%、パワー効率4.4lm/W、輝度−電流効率は7.9cd/A、駆動電圧は5.7Vであった。100cd/m2での駆動電圧は、比較例1よりも約1.6V低電圧化した。100cd/m2時のCIE色度と発光ピークはx=0.635、y=0.364、619nmであった。
例示化合物(E−2)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2時の駆動電圧は8.1Vであった。100cd/m2での外部量子効率(QE)は10.9%、パワー効率4.8lm/Wであった。100cd/m2時のCIE色度と発光ピークはx=0.665、y=0.332、621nmであった。
例示化合物(E−2)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は11.3%、パワー効率5.5lm/W、駆動電圧は7.0Vであった。100cd/m2での駆動電圧は、比較例7よりも1.1V低電圧化した。100cd/m2時のCIE色度と発光ピークはx=0.654、y=0.346、624nmであった。
例示化合物(1―105)をゲスト材料として、ホスト材料(CBP)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2時の駆動電圧は6.7Vであった。100cd/m2での外部量子効率(QE)は10.2%、パワー効率16.7lm/Wであった。
例示化合物(1−105)をゲスト材料として、ホスト材料(4−1)中に6重量%、共蒸着によるドーピングを行って、発光層を形成した。100cd/m2での外部量子効率(QE)は5.4%、パワー効率10.9lm/W、駆動電圧は5.8Vであった。100cd/m2での駆動電圧は、比較例8よりも1.0V低電圧化した。
Claims (11)
- 対向した電極間に2成分以上の材料で構成された発光層を有する有機発光素子において、該発光層の主構成材料が金属錯体であり、かつ副構成材料が燐光発光性発光材料である発光素子。
- 前記燐光発光性発光材料が白金又はイリジウム金属を有する材料である請求の範囲第1項に記載の発光素子。
- 前記燐光発光性発光材料が、下記一般式(2)に示される材料である請求の範囲第3項に記載の発光素子。
(式中、環A、環B、環C及び環Dは、この中の何れか2つの環が置換基を有していてもよい含窒素複素環を示し、残りの2つの環が置換基を有していてもよい芳香環または芳香族複素環を示し、環Aと環B、環Aと環C又は/及び環Bと環Dとで縮合環を形成してもよく、また、それぞれの環と前記置換基とで縮合環を形成していてもよい。X1、X2、X3及びX4は、この中のいずれか二つが白金原子に配位結合する窒素原子を示し、残りの二つは炭素原子又は窒素原子を表す。Q1、Q2、及びQ3は、それぞれ独立して、二価の原子又は原子団あるいは結合手を示すが、Q1、Q2、及びQ3が同時に結合手を表すことは無い。Z1、Z2、Z3及びZ4は、いずれか二つが配位結合手を示し、残りの二つが共有結合手、酸素原子又は硫黄原子を示す。) - 前記発光層の主構成材料における金属錯体が発光性有機金属錯体である請求の範囲第1項〜請求の範囲第6項のいずれか1項に記載の発光素子。
- 前記発光性有機金属錯体が燐光発光性金属錯体である請求の範囲第7項に記載の発光素子。
- 前記燐光発光性金属錯体が下記一般式(6)で表される錯体である請求の範囲第8項に記載の発光素子。
(式中、R1、R2、R3、R4、R5、R6、R7及びR8は、それぞれ独立して水素原子、アルキル基、アリール基、複素環基、アリル基、ハロゲン原子、アルコキシ基、ジアルキルアミノ基、ジアリールアミノ基又は重合性基が重合した基を示し、それぞれの置換基が他の置換基と結合してもよい。R9及びR10はそれぞれ独立して、アルキル基、アルコキシ基、アリール基又はハロゲン化アルキル基を表す。また、R9及びR10は重合性基又は該重合性基が重合した基を示す。Raは水素原子又はアルキル基を示す。nは1から3の整数を示し、n1は1から3の整数を示すが、nとn1の和は2又は3である。Mは遷移金属原子を示す。) - 請求の範囲第1項〜請求の範囲第10項のいずれか1項に記載の発光素子を有する表示装置。
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JP4642016B2 (ja) | 2003-05-09 | 2011-03-02 | 富士フイルム株式会社 | 有機電界発光素子及び白金化合物 |
JP4813032B2 (ja) * | 2004-09-21 | 2011-11-09 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4531509B2 (ja) | 2004-09-27 | 2010-08-25 | 富士フイルム株式会社 | 発光素子 |
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JP4790298B2 (ja) * | 2005-04-08 | 2011-10-12 | 日本放送協会 | 良溶解性イリジウム錯体及び有機el素子 |
EP3093898B1 (en) * | 2006-03-30 | 2017-12-13 | Konica Minolta Holdings, Inc. | Organic electroluminescence device and lighting device |
JP4980938B2 (ja) * | 2008-01-18 | 2012-07-18 | 三井化学株式会社 | 有機電界発光素子 |
US9034483B2 (en) * | 2008-09-16 | 2015-05-19 | Universal Display Corporation | Phosphorescent materials |
DE102008063470A1 (de) * | 2008-12-17 | 2010-07-01 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
JP5770441B2 (ja) * | 2009-09-30 | 2015-08-26 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子用材料、及び有機電界発光素子 |
JP4659910B2 (ja) * | 2010-01-07 | 2011-03-30 | 富士フイルム株式会社 | 発光素子 |
JP5097808B2 (ja) * | 2010-08-30 | 2012-12-12 | 富士フイルム株式会社 | 発光素子 |
JP2014231477A (ja) * | 2011-09-21 | 2014-12-11 | シャープ株式会社 | アルコキシ基を有する遷移金属錯体、及びこれを用いた有機発光素子、色変換発光素子、光変換発光素子、有機レーザーダイオード発光素子、色素レーザー、表示装置、照明装置並びに電子機器 |
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JP2014049696A (ja) * | 2012-09-03 | 2014-03-17 | Nippon Hoso Kyokai <Nhk> | 有機電界発光素子 |
DE102013111552A1 (de) | 2013-10-21 | 2015-04-23 | Osram Oled Gmbh | Organisches lichtemittierendes Bauelement |
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JP7105012B2 (ja) * | 2018-10-31 | 2022-07-22 | 四川知本快車創新科技研究院有限公司 | 赤色oled応用のための増加した放出量子収率を有する白金(ii)シッフ塩基錯体 |
CN112898962B (zh) * | 2021-01-30 | 2024-03-12 | 西安交通大学 | (C^N)Pt(II)(N-Donor)Cl型多核聚集诱导磷光增强发光材料 |
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