JP5209208B2 - 有機発光デバイスにおける発光ドーパントとして使用されるビス(アジニル)メテンホウ素錯体 - Google Patents
有機発光デバイスにおける発光ドーパントとして使用されるビス(アジニル)メテンホウ素錯体 Download PDFInfo
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- JP5209208B2 JP5209208B2 JP2006551408A JP2006551408A JP5209208B2 JP 5209208 B2 JP5209208 B2 JP 5209208B2 JP 2006551408 A JP2006551408 A JP 2006551408A JP 2006551408 A JP2006551408 A JP 2006551408A JP 5209208 B2 JP5209208 B2 JP 5209208B2
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- bis
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- light emitting
- azinyl
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- 239000002019 doping agent Substances 0.000 title claims description 26
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 25
- 229910052796 boron Inorganic materials 0.000 title claims description 21
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title claims description 19
- -1 anthracene compound Chemical class 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 40
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 72
- 239000000463 material Substances 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 229910052715 tantalum Inorganic materials 0.000 description 11
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 230000008021 deposition Effects 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 125000005259 triarylamine group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
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- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- AUUOUAPVXRPLMA-UHFFFAOYSA-N 2,2-di(quinolin-2-yl)acetonitrile Chemical compound C1=CC=CC2=NC(C(C=3N=C4C=CC=CC4=CC=3)C#N)=CC=C21 AUUOUAPVXRPLMA-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical class C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 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 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical compound C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical class C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- BJJDXAFKCKSLTE-UHFFFAOYSA-N 2,6-dimethylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C)=N1 BJJDXAFKCKSLTE-UHFFFAOYSA-N 0.000 description 1
- XGSWIASHHYQAJG-UHFFFAOYSA-N 2-(3-pentadecylphenoxy)hexanamide Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OC(CCCC)C(N)=O)=C1 XGSWIASHHYQAJG-UHFFFAOYSA-N 0.000 description 1
- CAGHCVFSSWSUAZ-UHFFFAOYSA-N 2-(3-tert-butyl-4-hydroxyphenoxy)tetradecanamide Chemical compound CCCCCCCCCCCCC(C(N)=O)OC1=CC=C(O)C(C(C)(C)C)=C1 CAGHCVFSSWSUAZ-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YPUFOHGCKCFWAW-UHFFFAOYSA-N 2-n,6-n-dinaphthalen-1-yl-2-n,6-n-dinaphthalen-2-ylnaphthalene-2,6-diamine;2-n,2-n,6-n,6-n-tetrakis(4-methylphenyl)naphthalene-2,6-diamine;2-n,2-n,6-n,6-n-tetranaphthalen-1-ylnaphthalene-2,6-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1.C1=CC=C2C(N(C=3C=C4C=CC(=CC4=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1.C1=CC=C2C(N(C=3C=C4C=CC(=CC4=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 YPUFOHGCKCFWAW-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical class N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- UNFOICLZNBECOR-UHFFFAOYSA-N 2-quinolin-2-ylacetonitrile Chemical compound C1=CC=CC2=NC(CC#N)=CC=C21 UNFOICLZNBECOR-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ORPXKVFCUSJGIS-UHFFFAOYSA-N 4-dodecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCC1=CC=C(S(N)(=O)=O)C=C1 ORPXKVFCUSJGIS-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- HOEOVAJYEQMKPZ-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline;4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-4-phenylcyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCC(CC1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 HOEOVAJYEQMKPZ-UHFFFAOYSA-N 0.000 description 1
- BITWULPDIGXQDL-UHFFFAOYSA-N 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene Chemical compound C=1C=C(C=2C3=CC=CC=C3C(C=3C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=3)=C3C=CC=CC3=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 BITWULPDIGXQDL-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004882 thiopyrans Chemical class 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
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
-
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Description
AとA'は、独立に、少なくとも1個の窒素を含む6員の芳香族環系に対応するアジン環基系を表わし;
XaとXbはそれぞれ、独立に選択した置換基であり、そのうちの2つが合わさってAまたはA'との縮合環を形成していてもよく、AまたはA'はさらに縮合環置換を含んでいてもよく;
mとnは、独立に、0〜4であり;
Yは、Hまたは置換基であり;
ZaとZbは、独立に選択した置換基であり;
1、2、3、4、1'、2'、3'、4'は、独立に選択した炭素原子または窒素原子であり;
XaとXbを、さらに置換されているものも含めてそれぞれ選択することにより、縮合した少なくとも5個の環からなる縮合環系になり;
さらに、上記縮合環系上に、非プロトン性溶媒中の濃度を10-3 M未満にして測定したときに最大発光波長が520nm未満になるような少なくとも1個の置換基が存在している。
Xa、Xb、Xc、Xdのそれぞれは、独立に選択した置換基であり、そのうちの2つが合わさって1つの縮合環を形成していてもよく、Xa、Xb、Xc、Xdのそれぞれはさらに別の縮合環置換を含んでいてもよく;
mとnは、独立に、0〜2であり;
oとpは、独立に、0〜4であり;
Yは、Hまたは置換基であり;
ZaとZbは、独立に選択した置換基であり;
さらに、上記縮合環系上に、非プロトン性溶媒中の濃度を10-3 M未満にして測定したときに最大発光波長が520nm未満になるような少なくとも1個の置換基が存在している。
Xa、Xb、Xc、Xdのそれぞれは、独立に選択した置換基であり、そのうちの2つが合わさって1つの縮合環を形成していてもよく、Xa、Xb、Xc、Xdのそれぞれはさらに別の縮合環置換を含んでいてもよく;
mとpは、独立に、0〜2であり;
nとoは、独立に、0〜4であり;
Yは、Hまたは置換基であり;
ZaとZbは、独立に選択した置換基であり;
さらに、上記縮合環系上に、非プロトン性溶媒中の濃度を10-3 M未満にして測定したときに最大発光波長が520nm未満になるような少なくとも1個の置換基が存在している。
R1とR2は、それぞれ独立に、水素原子、アリール基、アルキル基のいずれかを表わすか、R1とR2は、合わさって、シクロアルキル基を完成させる原子を表わし;
R3とR4は、それぞれ独立にアリール基を表わし、そのアリール基は、構造式(C):
R5とR6は、独立に、アリール基の中から選択される。一実施態様では、R5とR6のうちの少なくとも一方は、多環縮合環構造(例えばナフタレン)を含んでいる。
それぞれのAreは、独立に選択されたアリーレン基(例えばフェニレン基またはアントラセン基)であり;
nは1〜4の整数であり;
Ar、R7、R8、R9は、独立に選択されたアリール基である。
1,1-ビス(4-ジ-p-トリルアミノフェニル)シクロヘキサン
1,1-ビス(4-ジ-p-トリルアミノフェニル)-4-フェニルシクロヘキサン
4,4'-ビス(ジフェニルアミノ)クアドリフェニル
ビス(4-ジメチルアミノ-2-メチルフェニル)フェニルメタン
N,N,N-トリ(p-トリル)アミン
4-(ジ-p-トリルアミノ)-4'-[4-(ジ -p-トリルアミノ)-スチリル]スチルベン
N,N,N',N'-テトラ-p-トリル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラフェニル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラ-1-ナフチル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラ-2-ナフチル-4,4'-ジアミノビフェニル
N-フェニルカルバゾール
4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(1-ナフチル)-N-(2-ナフチル)アミノ]ビフェニル
4,4"-ビス[N-(1-ナフチル)-N-フェニルアミノ]p-テルフェニル
4,4'-ビス[N-(2-ナフチル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(3-アセナフテニル)-N-フェニルアミノ]ビフェニル
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン
4,4'-ビス[N-(9-アントリル)-N-フェニルアミノ]ビフェニル
4,4"-ビス[N-(1-アントリル)-N-フェニルアミノ]-p-テルフェニル
4,4'-ビス[N-(2-フェナントリル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(8-フルオランテニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ピレニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ナフタセニル
)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ペリレニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(1-コロネニル)-N-フェニルアミノ]ビフェニル
2,6-ビス(ジ-p-トリルアミノ)ナフタレン
2,6-ビス[ジ-(1-ナフチル)アミノ]ナフタレン
2,6-ビス[N-(1-ナフチル)-N-(2-ナフチル)アミノ]ナフタレン
N,N,N',N'-テトラ(2-ナフチル)-4,4"-ジアミノ-p-テルフェニル
4,4'-ビス{N-フェニル-N-[4-(1-ナフチル)-フェニル]アミノ}ビフェニル
4,4'-ビス[N-フェニル-N-(2-ピレニル)アミノ]ビフェニル
2,6-ビス[N,N-ジ(2-ナフチル)アミン]フルオレン
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン。
CO-1:アルミニウムトリスオキシン[別名、トリス(8-キノリノラト)アルミニウム(III)]
CO-2:マグネシウムビスオキシン[別名、ビス(8-キノリノラト)マグネシウム(II)]
CO-3:ビス[ベンゾ{f}-8-キノリノラト]亜鉛(II)
CO-4:ビス(2-メチル-8-キノリノラト)アルミニウム(III)-μ-オキソ-ビス(2-メチル-8-キノリノラト)アルミニウム(III)
CO-5:インジウムトリスオキシン[別名、トリス(8-キノリノラト)インジウム]
CO-6:アルミニウムトリス(5-メチルオキシン)[別名、トリス(5-メチル-8-キノリノラト)アルミニウム(III)]
CO-7:リチウムオキシン[別名、(8-キノリノラト)リチウム(I)]
CO-8:ガリウムオキシン[別名、トリス(8-キノリノラト)ガリウム(III)]
CO-9:ジルコニウムオキシン[別名、テトラ(8-キノリノラト)ジルコニウム(IV)]
CO-10:ビス(2-メチル-8-キノリナト)-4-フェニルフェノラトアルミニウム(III)
グループ1:水素、一般に1〜24個の炭素原子を有するアルキル基とアルコキシ基;
グループ2:一般に6〜20個の炭素原子を有する環基;
グループ3:一般に6〜30個の炭素原子を有する炭素環式縮合環基(例えばナフチル基、アントラセニル基、ピレニル基、ペリレニル基)を完成させるのに必要な原子群;
グループ4:一般に5〜24個の炭素原子を有する複素環式縮合環基(例えばフリル基、チエニル基、ピリジル基、キノリニル基)を完成させるのに必要な原子群;
グループ5:一般に1〜24個の炭素原子を有するアルコキシアミノ基、アルキルアミノ基、アリールアミノ基;
グループ6:フッ素基、塩素基、ホウ素基、シアノ基。
Zは、-O、-NR、-Sのいずれかであり(ただしRは、Hまたは置換基である);
R'は、場合によっては存在している1個以上の置換基を表わし、Rと個々のR'は、水素、または一般に1〜24個の炭素原子を有するアルキル基(例えばプロピル基、t-ブチル基、ヘプチル基);炭素環基または複素環基(例えばフェニル基、ナフチル基、フリル基、チエニル基、ピリジル基、キノリニル基)、一般に5〜20個の炭素原子を有する縮合芳香族環を完成させるのに必要な原子群;ハロ(例えばクロロ、フルオロ)のいずれかであり;
Lは、通常はアルキル基またはアリール基を含んでいる結合単位であり、複数のベンズアゾールを互いに共役または非共役に結合させる。
例2
例3
例4
103 アノード
105 正孔注入層(HIL)
107 正孔輸送層(HTL)
109 発光層(LEL)
111 電子輸送層(ETL)
113 カソード
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US10/768,327 | 2004-01-30 | ||
US10/768,327 US7329466B2 (en) | 2004-01-30 | 2004-01-30 | Organic element for electroluminescent devices |
PCT/US2005/002344 WO2005076385A1 (en) | 2004-01-30 | 2005-01-18 | A bis(azinyl) methene boron complex used as an emissive dopant in an organic light emitting device |
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US9666826B2 (en) * | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
US20070207345A1 (en) * | 2006-03-01 | 2007-09-06 | Eastman Kodak Company | Electroluminescent device including gallium complexes |
US20100231125A1 (en) * | 2009-03-12 | 2010-09-16 | Sheng Li | Organic light emitting device to emit in near infrared |
US8206842B2 (en) | 2009-04-06 | 2012-06-26 | Global Oled Technology Llc | Organic element for electroluminescent devices |
JP2013201153A (ja) * | 2010-06-08 | 2013-10-03 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
US8715529B1 (en) | 2012-01-23 | 2014-05-06 | Arrowhead Center, Inc. | Synthesis and applications of triazaborolopyridinium compounds and substituted triazaborolopyridinium compounds and methods of use |
KR20150131825A (ko) * | 2014-05-16 | 2015-11-25 | 에스케이케미칼주식회사 | 피로메텐 붕소 착화합물을 포함하는 염료 |
KR20150131807A (ko) * | 2014-05-16 | 2015-11-25 | 에스케이케미칼주식회사 | 피로메텐 붕소 착화합물을 포함하는 염료 |
WO2018206526A1 (en) * | 2017-05-11 | 2018-11-15 | Merck Patent Gmbh | Organoboron complexes for organic electroluminescent devices |
JP6903169B2 (ja) | 2017-06-08 | 2021-07-14 | 日東電工株式会社 | ディスプレイデバイスで使用するためのbodipy化合物 |
KR102139423B1 (ko) | 2017-12-26 | 2020-07-29 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
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US7074503B2 (en) * | 2004-01-30 | 2006-07-11 | Eastman Kodak Company | Organic element for electroluminescent devices |
US6885026B1 (en) * | 2004-01-30 | 2005-04-26 | Eastman Kodak Company | Organic element for electroluminescent devices |
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US20050170204A1 (en) | 2005-08-04 |
KR20060133566A (ko) | 2006-12-26 |
US20060210829A9 (en) | 2006-09-21 |
JP2007524238A (ja) | 2007-08-23 |
TW200538531A (en) | 2005-12-01 |
KR101212582B1 (ko) | 2012-12-14 |
KR20120007552A (ko) | 2012-01-20 |
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