JP2015214526A - Novel organic compound and organic light emitting element having the same - Google Patents
Novel organic compound and organic light emitting element having the same Download PDFInfo
- Publication number
- JP2015214526A JP2015214526A JP2014099898A JP2014099898A JP2015214526A JP 2015214526 A JP2015214526 A JP 2015214526A JP 2014099898 A JP2014099898 A JP 2014099898A JP 2014099898 A JP2014099898 A JP 2014099898A JP 2015214526 A JP2015214526 A JP 2015214526A
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- layer
- organic
- organic light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 238000002347 injection Methods 0.000 claims abstract description 35
- 239000007924 injection Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 54
- 239000000758 substrate Substances 0.000 claims description 41
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 108091008695 photoreceptors Proteins 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 230000010365 information processing Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003446 ligand Substances 0.000 abstract description 9
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 abstract description 5
- 230000009257 reactivity Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000010409 thin film Substances 0.000 description 20
- 239000010408 film Substances 0.000 description 16
- -1 pentarenyl group Chemical group 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 229910052744 lithium Inorganic materials 0.000 description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000003230 hygroscopic agent Substances 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 229910052751 metal Chemical class 0.000 description 6
- 239000002184 metal Chemical class 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 230000003287 optical effect Effects 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Chemical class 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 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 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 150000002503 iridium Chemical class 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910021424 microcrystalline silicon Inorganic materials 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 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
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003281 rhenium Chemical class 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
- 150000003303 ruthenium Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 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 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
Abstract
Description
本発明は、新規有機化合物及びそれを有する有機発光素子、画像表示装置、画像情報処理装置、照明装置、電子写真方式の画像形成装置、露光装置に関する。 The present invention relates to a novel organic compound, an organic light-emitting element having the same, an image display device, an image information processing device, an illumination device, an electrophotographic image forming device, and an exposure device.
有機発光素子は、電極間に蛍光性又は燐光性有機化合物を含む薄膜を挟持させて、各電極から電子及びホール（正孔）を注入することにより、蛍光性又は燐光性化合物の励起子を生成させ、この励起子が基底状態に戻る際に放射される光を利用する素子である。 Organic light-emitting devices generate excitons of fluorescent or phosphorescent compounds by sandwiching a thin film containing a fluorescent or phosphorescent organic compound between electrodes and injecting electrons and holes from each electrode. And an element that utilizes light emitted when the exciton returns to the ground state.
有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化の可能性があることから、広汎な用途への可能性を示唆している。そのなかで駆動電圧を低減させる方法の一つとして、陰極と有機化合物層の間に、仕事関数の小さいアルカリ金属を電子注入層として挿入させる方法が知られている。しかし、このような電子注入層を用いた場合、水分に対するアルカリ金属の高い反応性により変質するため、陰極からの電子注入が著しく低下することが問題となっている。 Recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, thin and lightweight light-emitting devices at low applied voltage, so they can be used in a wide range of applications. Suggests the possibility. As one of the methods for reducing the drive voltage, a method is known in which an alkali metal having a small work function is inserted as an electron injection layer between the cathode and the organic compound layer. However, when such an electron injection layer is used, it deteriorates due to the high reactivity of the alkali metal with respect to moisture, so that there is a problem that the electron injection from the cathode is remarkably reduced.
アルカリ金属を用いた様々な化合物が提案されているが、特許文献１には、アルカリ金属、アルカリ土類金属、希土類を含む遷移金属等を電子注入層のドーパントに用いた有機発光素子が記載されている。特許文献２には、金属酸化物あるいは金属塩を電子注入層のドーパントに用いた有機発光素子が記載されている。また、特許文献３には、金属炭酸塩を電子注入層のドーパントに用いた有機発光素子が記載されている。さらに、非特許文献１には、重金属錯体の合成原料として、ピリジルピロール構造を有するリチウム化合物が記載されている。 Various compounds using an alkali metal have been proposed. Patent Document 1 describes an organic light-emitting device using an alkali metal, an alkaline earth metal, a transition metal containing a rare earth, or the like as a dopant for an electron injection layer. ing. Patent Document 2 describes an organic light emitting device using a metal oxide or a metal salt as a dopant for an electron injection layer. Patent Document 3 describes an organic light emitting device using metal carbonate as a dopant for an electron injection layer. Furthermore, Non-Patent Document 1 describes a lithium compound having a pyridylpyrrole structure as a raw material for synthesizing a heavy metal complex.
本発明は、耐湿性の高い有機発光素子を実現するのに適した新規有機化合物とそれを有する有機発光素子を提供することにある。 An object of the present invention is to provide a novel organic compound suitable for realizing an organic light emitting device having high moisture resistance and an organic light emitting device having the same.
本発明は、
下記一般式［１］、［２］いずれかで示されることを特徴とする有機化合物を提供する。
The present invention
Provided is an organic compound represented by any one of the following general formulas [1] and [2].
（式［１］、［２］において、Ｒ１〜Ｒ１０は、水素原子、直鎖または分岐状の炭素原子数１乃至４のアルキル基、置換あるいは無置換のアリール基、からそれぞれ独立に選ばれる。）を提供する。 (In the formulas [1] and [2], R1 to R10 are each independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group. )I will provide a.
本発明により耐湿性の高い有機化合物を提供することができる。そして耐湿性の高い有機発光素子を提供することができる。 According to the present invention, an organic compound having high moisture resistance can be provided. And an organic light emitting element with high moisture resistance can be provided.
以下、本発明に関して詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明に係る有機化合物は、下記一般式［１］、［２］いずれかで示されることを特徴とする有機化合物である。 The organic compound according to the present invention is an organic compound represented by any one of the following general formulas [1] and [2].
（式［１］、［２］において、Ｒ１〜Ｒ１０は、水素原子、直鎖または分岐状の炭素原子数１乃至４のアルキル基、置換あるいは無置換のアリール基、からそれぞれ独立に選ばれる。） (In the formulas [1] and [2], R1 to R10 are each independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group. )
直鎖または分岐状の炭素原子数１乃至４のアルキル基の具体例としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基から選ばれる置換基である。 Specific examples of the linear or branched alkyl group having 1 to 4 carbon atoms are selected from methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and tert-butyl group. It is a substituent.
アリール基の具体例としては、フェニル基、ナフチル基、ペンタレニル基、インデニル基、アズレニル基、アントリル基、ピレニル基、インダセニル基、アセナフテニル基、フェナントリル基、フェナレニル基、フルオランテニル基、アセフェナントリル基、アセアントリル基、トリフェニレニル基、クリセニル基、ナフタセニル基、ペリレニル基、ペンタセニル基、ビフェニル基、ターフェニル基、フルオレニル基などが挙げられるが、もちろんこれに限定されるものではない。好ましくは、フェニル基、ナフチル基、フルオレニル基、ピレニル基、フェナンスリル基である。 Specific examples of the aryl group include phenyl group, naphthyl group, pentarenyl group, indenyl group, azulenyl group, anthryl group, pyrenyl group, indacenyl group, acenaphthenyl group, phenanthryl group, phenalenyl group, fluoranthenyl group, acephenanthryl. Groups, aceanthryl groups, triphenylenyl groups, chrycenyl groups, naphthacenyl groups, perylenyl groups, pentacenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, and the like, but are not limited thereto. Preferred are phenyl group, naphthyl group, fluorenyl group, pyrenyl group, and phenanthryl group.
上記アリール基が有してもよい置換基として、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、デシル基、ｉｓｏ−プロピル基、ｉｓｏ−ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｉｓｏ−ペンチル基、ネオペンチル基、ｔｅｒｔ−オクチル基、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、２−フルオロエチル基、２，２，２−トリフルオロエチル基、パーフルオロエチル基、３−フルオロプロピル基、パーフルオロプロピル基、４−フルオロブチル基、パーフルオロブチル基、５−フルオロペンチル基、６−フルオロヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロペンチルメチル基、シクロヘキシルメチル基、シクロヘキシルエチル基、４−フルオロシクロヘキシル基、ノルボルニル基、アダマンチル基等のアルキル基、メトキシ基、エトキシ基、ｔｅｒｔ−ブトキシ基、ｉｓｏ−プロポキシ基等のアルコキシ基、フェニル基、ナフチル基等のアリール基、フッ素等のハロゲン原子等が挙げられるが、これら置換基に限定されるものではない。 As the substituent that the aryl group may have, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, an iso-propyl group, an iso-butyl group, sec-butyl group, tert-butyl group, iso-pentyl group, neopentyl group, tert-octyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2,2-trifluoro Ethyl group, perfluoroethyl group, 3-fluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, perfluorobutyl group, 5-fluoropentyl group, 6-fluorohexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl Group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl Group, cyclohexylethyl group, 4-fluorocyclohexyl group, norbornyl group, adamantyl group and other alkyl groups, methoxy group, ethoxy group, tert-butoxy group, iso-propoxy group and other alkoxy groups, phenyl group, naphthyl group and other aryl groups Groups, halogen atoms such as fluorine, and the like, but are not limited to these substituents.
式［１］についてより好ましくは、下記一般式［３］で示される化合物である。 More preferred for the formula [1] is a compound represented by the following general formula [3].
（式［３］において、Ｒ１１〜Ｒ１６は、水素原子、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、フェニル基、ナフチル基、フルオレニル基、フェナンスリル基、からそれぞれ独立に選ばれる。） (In Formula [3], R11 to R16 are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, and a phenanthryl group.)
式［２］についてより好ましくは、下記一般式［４］で示される化合物である。 More preferred for the formula [2] is a compound represented by the following general formula [4].
（式［４］において、Ｒ１７〜Ｒ２４は、水素原子、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、フェニル基、ナフチル基、フルオレニル基、フェナンスリル基、からそれぞれ独立に選ばれる。） (In Formula [4], R17 to R24 are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, and a phenanthryl group.)
本発明者等は、アルカリ金属の中でリチウムに注目した。リチウムは、水との反応性はアルカリ金属中では最も穏かである。そこで、耐湿性が高い有機発光素子を実現するために、リチウムを配位子で覆って、水分と反応し難くし、より耐水性が高くなるような設計を行った。さらに、有機発光素子作製時に真空加熱蒸着を行うため、耐熱性も兼ね備えた設計を行う必要がある。これまで、フッ化リチウムのような無機化合物が有機発光素子に使用されているが、それは水分に対して反応性が高く、吸湿してしまう。 The present inventors paid attention to lithium among alkali metals. Lithium has the mildest reactivity with water among alkali metals. Therefore, in order to realize an organic light-emitting device with high moisture resistance, a design was made such that lithium is covered with a ligand so that it does not easily react with moisture, and water resistance becomes higher. Furthermore, since vacuum heating vapor deposition is performed at the time of producing the organic light-emitting element, it is necessary to design with heat resistance. So far, inorganic compounds such as lithium fluoride have been used in organic light emitting devices, but they are highly reactive with moisture and absorb moisture.
これらを考慮し、耐水性と耐熱性の両方を兼ね備えるための第一の設計要素として、五員環の二座配位子による錯体の安定性向上が挙げられる。一般的に、単座配位より二座配位の方がより安定な錯体を形成する。さらに、配位結合の安定度として、三員環＜四員環＜五員環＞六員環の序列で示される。第二の設計要素として、ゼロ価の二座配位子を第二の配位子として用いることで、中心のリチウム原子を立体的に水から守る構造にすることが挙げられる。非特許文献１に示されている錯体は、五員環の二座配位子が一つで錯体を形成されているが、さらに立体的に保護した構造が、本発明の一般式［１］乃至［２］のいずれかの化合物である。 Considering these, as a first design element for having both water resistance and heat resistance, improvement of the stability of the complex by a five-membered bidentate ligand can be mentioned. In general, bidentate coordination forms a more stable complex than monodentate coordination. Furthermore, the stability of the coordination bond is indicated by the order of three-membered ring <four-membered ring <five-membered ring> six-membered ring. As a second design element, a structure in which a central lithium atom is sterically protected from water by using a zero-valent bidentate ligand as a second ligand can be mentioned. In the complex shown in Non-Patent Document 1, a complex is formed by one bidentate bidentate ligand having a five-membered ring, but a sterically protected structure is represented by the general formula [1] of the present invention. To any compound of [2].
本発明者等は、鋭意検討した結果、陰極から電子の注入性を有し、水分に対する反応性が極めて低い電子注入材料を発見するに至った。その電子注入材料は、上記一般式［１］乃至［２］で示される、リチウム錯体化合物である。 As a result of intensive studies, the present inventors have found an electron injection material having an electron injection property from the cathode and a very low reactivity to moisture. The electron injection material is a lithium complex compound represented by the above general formulas [1] to [2].
一般式［１］乃至［２］の具体例としては、下記のような構造があげられるが、これらに限定されるものではない。 Specific examples of the general formulas [1] to [2] include the following structures, but are not limited thereto.
例示化合物のうちＡ１−１乃至Ａ１−２５に示す化合物は、Ａ群である。 Of the exemplified compounds, the compounds represented by A1-1 to A1-25 are Group A.
Ａ群は、配位子として、フェナントロリン構造を有するため、平面性が高く、より疎水性の向上が期待できる。さらに、Ａ−１乃至Ａ−１２は、置換基としてアルキル基を有する。そのため分子のスタック性を緩和する効果が期待できる。Ａ−１３乃至Ａ−２５は、フェニル基やアリール基を置換基として有しているため、より疎水性の向上が期待でき、好ましい。 Since the group A has a phenanthroline structure as a ligand, it has high planarity and can be expected to improve hydrophobicity. Furthermore, A-1 to A-12 have an alkyl group as a substituent. Therefore, the effect of relaxing the stacking property of the molecule can be expected. Since A-13 thru | or A-25 have a phenyl group or an aryl group as a substituent, a hydrophobic improvement can be anticipated more and it is preferable.
例示化合物のうちＢ１−１乃至Ｂ１−２５に示す化合物は、Ｂ群である。 Of the exemplified compounds, the compounds represented by B1-1 to B1-25 are Group B.
Ｂ群は、配位子として、ビピリジン構造を有するため、ピリジン間に単結合で連結されている。従って、Ａ群より柔軟な構造であるため、分子間相互作用を軽減でき、昇華性の向上が期待できる。さらに、Ｂ−１乃至Ｂ−１２は、置換基としてアルキル基を有する。そのため分子のスタック性を緩和する効果が期待できるＢ−１３乃至Ｂ−２５は、フェニル基やアリール基を置換基として有する。そのためより疎水性の向上が期待でき、好ましい。 Since the group B has a bipyridine structure as a ligand, it is linked by a single bond between pyridines. Therefore, since the structure is more flexible than the group A, intermolecular interaction can be reduced, and improvement in sublimation can be expected. Furthermore, B-1 thru | or B-12 have an alkyl group as a substituent. Therefore, B-13 to B-25, which can be expected to reduce the stacking property of molecules, have a phenyl group or an aryl group as a substituent. Therefore, the improvement of hydrophobicity can be expected, which is preferable.
陰極からの電子注入を効率よく行うため、上記一般式［１］乃至［２］で示される、リチウム錯体化合物が陰極と接する電子注入層に含まれることが好ましい。その際、上記一般式［１］乃至［２］で示される、リチウム錯体化合物が単独で電子注入層であっても、他材料と混合された状態であってもよい。他材料と混合されている状態である場合、上記一般式［１］乃至［２］で示される、リチウム錯体化合物がゲスト材料とであるとするとゲスト材料の含有率は、有機化合物層である電子注入層の全量に対し、５０重量％以下である。そしてそれ以外はホスト材料や更に他の添加物である。 In order to efficiently inject electrons from the cathode, the lithium complex compound represented by the general formulas [1] to [2] is preferably included in the electron injection layer in contact with the cathode. At that time, the lithium complex compound represented by the above general formulas [1] to [2] may be an electron injection layer alone or may be mixed with other materials. When the lithium complex compound represented by the above general formulas [1] to [2] is a guest material in a state where it is mixed with another material, the content of the guest material is an electron that is an organic compound layer. It is 50 weight% or less with respect to the whole quantity of an injection | pouring layer. The others are host materials and other additives.
ここでいうホスト材料とは電子注入層の多くを構成する材料のことである。 The host material here refers to a material constituting most of the electron injection layer.
（有機発光素子の説明）
次に本実施形態に係る有機発光素子を説明する。
(Description of organic light emitting device)
Next, the organic light emitting device according to this embodiment will be described.
本実施形態に係る有機発光素子は一対の電極である陽極と陰極と、それらの間に配置される有機化合物層とを有し、この有機化合物層が発光層と前記陰極に接する電子注入層と有し、前記電子注入層として一般式［１］で示される有機化合物を有する素子である。 The organic light-emitting device according to this embodiment has a pair of electrodes, an anode and a cathode, and an organic compound layer disposed therebetween, and the organic compound layer is in contact with the light-emitting layer and the cathode. And an element having an organic compound represented by the general formula [1] as the electron injection layer.
本発明に係る有機化合物を用いて作製される有機発光素子としては、基板上に、順次陽極、発光層、電子注入層、陰極を設けた構成のものが挙げられる。他にも順次陽極、正孔輸送層、電子輸送層、電子注入層、陰極を設けた構成のものが挙げられる。また順次陽極、正孔輸送層、発光層、電子輸送層、電子注入層、陰極を設けたものや順次陽極、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層、陰極を設けたものや順次、陽極、正孔輸送層、発光層、正孔・エキシトンブロッキング層、電子輸送層、電子注入層、陰極を設けたものが挙げられる。ただしこれら５種の多層型の例はあくまでごく基本的な素子構成であり、本発明に係る化合物を用いた有機発光素子の構成はこれらに限定されるものではない。 Examples of the organic light emitting device produced using the organic compound according to the present invention include a structure in which an anode, a light emitting layer, an electron injection layer, and a cathode are sequentially provided on a substrate. In addition, a structure in which an anode, a hole transport layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided can be used. Also sequentially provided anode, hole transport layer, light emitting layer, electron transport layer, electron injection layer, cathode and sequentially anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, Examples thereof include those provided with a cathode, and those provided with an anode, a hole transport layer, a light emitting layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, and a cathode in this order. However, these five types of multilayer type are just basic device configurations, and the configuration of the organic light emitting device using the compound according to the present invention is not limited to these.
以下にこれらの化合物例を挙げる。 Examples of these compounds are given below.
正孔注入輸送性材料としては、陽極からの正孔の注入を容易にして、かつ注入された正孔を発光層へ輸送できるように正孔移動度が高い材料が好ましい。また有機発光素子中において結晶化等の膜質の劣化を防ぐために、ガラス転移点温度が高い材料が好ましい。正孔注入輸送性能を有する低分子及び高分子系材料としては、トリアリールアミン誘導体、アリールカルバゾール誘導体、フェニレンジアミン誘導体、スチルベン誘導体、フタロシアニン誘導体、ポルフィリン誘導体、ポリ（ビニルカルバゾール）、ポリ（チオフェン）、その他導電性高分子が挙げられる。さらに上記の正孔注入輸送性材料は、電子阻止層にも好適に使用される。 As the hole injecting and transporting material, a material having a high hole mobility is preferable so that the injection of holes from the anode can be facilitated and the injected holes can be transported to the light emitting layer. In order to prevent deterioration of film quality such as crystallization in the organic light emitting device, a material having a high glass transition temperature is preferable. Low molecular and high molecular weight materials having hole injection and transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole), poly (thiophene), Other examples include conductive polymers. Further, the hole injecting / transporting material is also preferably used for the electron blocking layer.
以下に、正孔注入輸送性材料として用いられる化合物の具体例を示すが、もちろんこれらに限定されるものではない。 Specific examples of the compound used as the hole injecting and transporting material are shown below, but the present invention is not limited to these.
主に発光機能に関わる発光材料としては、縮環化合物（例えばフルオレン誘導体、ナフタレン誘導体、ピレン誘導体、ペリレン誘導体、テトラセン誘導体、アントラセン誘導体、ルブレン等）、キナクリドン誘導体、クマリン誘導体、スチルベン誘導体、トリス（８−キノリノラート）アルミニウム等の有機アルミニウム錯体、イリジウム錯体、白金錯体、レニウム錯体、銅錯体、ユーロピウム錯体、ルテニウム錯体、及びポリ（フェニレンビニレン）誘導体、ポリ（フルオレン）誘導体、ポリ（フェニレン）誘導体等の高分子誘導体が挙げられる。 The light-emitting materials mainly related to the light-emitting function include condensed ring compounds (for example, fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, tris (8 -Quinolinolate) High organometallic complexes such as aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, poly (phenylene vinylene) derivatives, poly (fluorene) derivatives, poly (phenylene) derivatives, etc. Examples include molecular derivatives.
以下に、発光材料として用いられる化合物の具体例を示すが、もちろんこれらに限定されるものではない。 Although the specific example of the compound used as a luminescent material is shown below, of course, it is not limited to these.
発光層に含まれる発光層ホスト材料あるいは発光アシスト材料としては、芳香族炭化水素化合物もしくはその誘導体の他、カルバゾール誘導体、ジベンゾフラン誘導体、ジベンゾチオフェン誘導体、トリス（８−キノリノラート）アルミニウム等の有機アルミニウム錯体、有機ベリリウム錯体等が挙げられる。なお、ホスト材料に対する発光材料（ゲスト材料）の濃度は０．１質量％以上３０質量％以下であることが好ましく、０．５ｗｔ％以上１０ｗｔ％以下であることがより好ましい。 As a light emitting layer host material or a light emission assist material contained in the light emitting layer, an aromatic hydrocarbon compound or a derivative thereof, a carbazole derivative, a dibenzofuran derivative, a dibenzothiophene derivative, an organoaluminum complex such as tris (8-quinolinolato) aluminum, Organic beryllium complex etc. are mentioned. Note that the concentration of the light-emitting material (guest material) with respect to the host material is preferably 0.1% by mass or more and 30% by mass or less, and more preferably 0.5% by weight or more and 10% by mass or less.
以下に、発光層ホスト材料あるいは発光層アシスト材料として用いられる化合物の具体例を示すが、もちろんこれらに限定されるものではない。 Specific examples of the compound used as the light emitting layer host material or the light emitting layer assist material are shown below, but the present invention is of course not limited thereto.
電子輸送性材料としては、陰極から注入された電子を発光層へ輸送することができるものから任意に選ぶことができ、正孔輸送性材料の正孔移動度とのバランス等を考慮して選択される。電子輸送性能を有する材料としては、オキサジアゾール誘導体、オキサゾール誘導体、ピラジン誘導体、トリアゾール誘導体、トリアジン誘導体、キノリン誘導体、キノキサリン誘導体、フェナントロリン誘導体、有機アルミニウム錯体、縮環化合物（例えばフルオレン誘導体、ナフタレン誘導体、クリセン誘導体、アントラセン誘導体等）が挙げられる。さらに上記の電子輸送性材料は、正孔阻止層にも好適に使用される。 The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Is done. Materials having electron transport performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, condensed compounds (for example, fluorene derivatives, naphthalene derivatives, Chrysene derivatives, anthracene derivatives, etc.). Further, the above electron transporting material is also suitably used for the hole blocking layer.
以下に、電子輸送性材料として用いられる化合物の具体例を示すが、もちろんこれらに限定されるものではない。 Specific examples of the compound used as the electron transporting material are shown below, but of course not limited thereto.
陽極の構成材料としては仕事関数がなるべく大きなものがよい。例えば、金、白金、銀、銅、ニッケル、パラジウム、コバルト、セレン、バナジウム、タングステン等の金属単体あるいはこれらを組み合わせた合金、酸化錫、酸化亜鉛、酸化インジウム、酸化錫インジウム（ＩＴＯ）、酸化亜鉛インジウム等の金属酸化物が使用できる。またポリアニリン、ポリピロール、ポリチオフェン等の導電性ポリマーも使用できる。 As the material for the anode, a material having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., or an alloy combining them, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), zinc oxide Metal oxides such as indium can be used. In addition, conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.
これらの電極物質は一種類を単独で使用してもよいし、二種類以上を併用して使用してもよい。また、陽極は一層で構成されていてもよく、複数の層で構成されていてもよい。 These electrode materials may be used alone or in combination of two or more. Moreover, the anode may be composed of a single layer or a plurality of layers.
一方、陰極の構成材料としては仕事関数の小さなものがよい。例えばリチウム等のアルカリ金属、カルシウム等のアルカリ土類金属、アルミニウム、チタニウム、マンガン、銀、鉛、クロム等の金属単体が挙げられる。あるいはこれら金属単体を組み合わせた合金も使用することができる。例えばマグネシウム−銀、アルミニウム−リチウム、アルミニウム−マグネシウム等が使用できる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。これらの電極物質は一種類を単独で使用してもよいし、二種類以上を併用して使用してもよい。また陰極は一層構成でもよく、多層構成でもよい。 On the other hand, the material constituting the cathode is preferably a material having a small work function. Examples thereof include alkali metals such as lithium, alkaline earth metals such as calcium, and simple metals such as aluminum, titanium, manganese, silver, lead, and chromium. Or the alloy which combined these metal single-piece | units can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, etc. can be used. A metal oxide such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination of two or more. The cathode may have a single layer structure or a multilayer structure.
本発明の有機発光素子を構成する有機化合物層（正孔注入層、正孔輸送層、電子阻止層、発光層、正孔阻止層、電子輸送層、電子注入層等）は、以下に示す方法により形成される。 The organic compound layer (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device of the present invention is a method shown below. It is formed by.
発明の有機発光素子を構成する有機化合物層は、真空蒸着法、イオン化蒸着法、スパッタリング、プラズマ等のドライプロセスを用いることができる。またドライプロセスに代えて、適当な溶媒に溶解させて公知の塗布法（例えば、スピンコーティング、ディッピング、キャスト法、ＬＢ法、インクジェット法等）により層を形成するウェットプロセスを用いることもできる。 The organic compound layer constituting the organic light-emitting device of the invention can use a dry process such as a vacuum deposition method, an ionization deposition method, sputtering, or plasma. In place of the dry process, a wet process in which a layer is formed by a known coating method (for example, spin coating, dipping, casting method, LB method, ink jet method, etc.) after dissolving in an appropriate solvent may be used.
ここで真空蒸着法や溶液塗布法等によって層を形成すると、結晶化等が起こりにくく経時安定性に優れる。また塗布法で成膜する場合は、適当なバインダー樹脂と組み合わせて膜を形成することもできる。 Here, when a layer is formed by a vacuum deposition method, a solution coating method, or the like, crystallization or the like hardly occurs and the temporal stability is excellent. Moreover, when forming into a film by the apply | coating method, a film | membrane can also be formed combining with a suitable binder resin.
上記バインダー樹脂としては、ポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ＡＢＳ樹脂、アクリル樹脂、ポリイミド樹脂、フェノール樹脂、エポキシ樹脂、シリコン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。 Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like. .
また、これらバインダー樹脂は、ホモポリマー又は共重合体として一種類を単独で使用してもよいし、二種類以上を混合して使用してもよい。さらに必要に応じて、公知の可塑剤、酸化防止剤、紫外線吸収剤等の添加剤を併用してもよい。 Moreover, these binder resins may be used alone as a homopolymer or a copolymer, or may be used in combination of two or more. Furthermore, you may use together additives, such as a well-known plasticizer, antioxidant, and an ultraviolet absorber, as needed.
（有機発光素子の用途）
本発明の有機発光素子は、画像表示装置や照明装置の構成部材として用いることができる。他にも、電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライト、白色光源にカラーフィルターを有する発光装置等の用途がある。カラーフィルターは例えば赤、緑、青の３つの色が透過するフィルターが挙げられる。
(Applications of organic light emitting devices)
The organic light emitting device of the present invention can be used as a constituent member of an image display device or a lighting device. In addition, there are uses such as an exposure light source of an electrophotographic image forming apparatus, a backlight of a liquid crystal display device, and a light emitting device having a color filter in a white light source. Examples of the color filter include filters that transmit three colors of red, green, and blue.
画像表示装置はカラーフィルターを有してもよい、その場合画像表示装置は、基板と、画素に対応した有機発光素子と、カラーフィルターを有し、発光層は白色光を発し、カラーフィルターが各画素に対応した白色光を赤や緑や青に変換する。本発明に係る式１で示す有機化合物は、この有機発光層の電子注入層に用いられる。この有機発光素子は発光層が１つであっても２つ以上の複数でもよい。蛍光発光材料や燐光発光材料は発色したい色ごとに適宜選べばよい。一方の副発光層には１種の色、他方の副発光層には２種の色が発光するように発光材料を適宜設けてもよい。燐光発光材料は例えばイリジウム錯体である。 The image display device may include a color filter. In that case, the image display device includes a substrate, an organic light emitting element corresponding to the pixel, and a color filter, the light emitting layer emits white light, and the color filter The white light corresponding to the pixel is converted into red, green or blue. The organic compound represented by Formula 1 according to the present invention is used for the electron injection layer of the organic light emitting layer. This organic light emitting device may have one light emitting layer or a plurality of two or more. A fluorescent light emitting material or a phosphorescent light emitting material may be appropriately selected for each color to be developed. A light-emitting material may be provided as appropriate so that one sub-light-emitting layer emits one color and the other sub-light-emitting layer emits two colors. The phosphorescent material is, for example, an iridium complex.
すなわち発光層は第一の副発光層と第二の副発光層を有し、有機発光素子が白色光を発光する場合、その白色光は第一の副発光層と第二の副発光層のそれぞれの発光色が混ざって得られる光であればよい。 That is, the light emitting layer has a first sub light emitting layer and a second sub light emitting layer, and when the organic light emitting element emits white light, the white light is emitted from the first sub light emitting layer and the second sub light emitting layer. Any light obtained by mixing the respective emission colors may be used.
画像表示装置において基板は透明基板でも不透明基板でもよい。ここでいう透明とは、素子が発光する光に対して透明であるという意味である。基板が透明基板である場合、素子が発光した光が基板を透過して外部にとりだされるいわゆるボトムエミッション構成もよい。 In the image display device, the substrate may be a transparent substrate or an opaque substrate. The term “transparent” as used herein means that the element is transparent to light emitted. When the substrate is a transparent substrate, a so-called bottom emission configuration in which light emitted from the element is transmitted through the substrate and taken out to the outside may be used.
本発明の画像表示装置は、本発明の有機発光素子を表示部に有する。尚、この表示部は複数の画素を有する。 The image display device of the present invention has the organic light emitting device of the present invention in a display portion. This display unit has a plurality of pixels.
そしてこの画素は、本発明の有機発光素子と、発光輝度を制御するための能動素子（スイッチング素子）又は増幅素子の一例であるトランジスタとを有し、この有機発光素子の陽極又は陰極とトランジスタのドレイン電極又はソース電極とが電気接続されている。ここで画像表示装置は、ＰＣ等の画像表示装置として用いることができる。上記トランジスタとして、例えば、ＴＦＴ素子が挙げられ、このＴＦＴ素子は、例えば、基板の絶縁性表面に設けられている。 The pixel includes the organic light emitting device of the present invention and a transistor which is an example of an active device (switching device) or an amplifying device for controlling light emission luminance. The anode or cathode of the organic light emitting device and the transistor A drain electrode or a source electrode is electrically connected. Here, the image display device can be used as an image display device such as a PC. An example of the transistor is a TFT element, and this TFT element is provided on, for example, an insulating surface of a substrate.
画像表示装置は、エリアＣＣＤ、リニアＣＣＤ、メモリーカード等からの画像情報を入力する画像入力部を有し、入力された画像を表示部に表示する情報処理装置でもよい。 The image display device may be an information processing device that includes an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, or the like, and displays the input image on the display unit.
また、撮像装置やインクジェットプリンタが有する表示部は、タッチパネル機能を有していてもよい。このタッチパネル機能の駆動方式は特に限定されない。 In addition, a display unit included in the imaging device or the inkjet printer may have a touch panel function. The driving method of the touch panel function is not particularly limited.
また画像表示装置はマルチファンクションプリンタの表示部に用いられてもよい。 The image display device may be used for a display unit of a multifunction printer.
照明装置は例えば室内を照明する装置である。照明装置は白色（色温度が４２００Ｋ）、昼白色（色温度が５０００Ｋ）、その他青から赤のいずれの色を発光するものであってもよい。 The lighting device is, for example, a device that illuminates a room. The lighting device may emit white light (color temperature is 4200K), day white light (color temperature is 5000K), or any other color from blue to red.
本発明の照明装置は、本発明の有機発光素子と、この有機発光素子と接続するＡＣ／ＤＣコンバーター回路（交流電圧を直流電圧に変換する回路）とを有している。尚、この照明装置は、カラーフィルターをさらに有してもよい。 The lighting device of the present invention includes the organic light-emitting element of the present invention and an AC / DC converter circuit (a circuit that converts an alternating voltage into a direct voltage) connected to the organic light-emitting element. In addition, this illuminating device may further have a color filter.
本発明の電子写真方式の画像形成装置は、感光体とそれを露光する露光部を有する。 The electrophotographic image forming apparatus of the present invention has a photoreceptor and an exposure unit that exposes the photoreceptor.
ここで画像形成装置に備える露光部は、本発明の有機発光素子を含んでいる。 Here, the exposure unit provided in the image forming apparatus includes the organic light emitting device of the present invention.
また電子写真方式の画像形成装置は、感光体とこの感光体の表面を帯電させる帯電手段と、感光体を露光して靜電潜像を形成するための露光部と、感光体の表面に形成された静電潜像を現像するための現像器とを有する画像形成装置である。 The electrophotographic image forming apparatus is formed on the surface of the photoconductor, a charging unit for charging the surface of the photoconductor, an exposure unit for exposing the photoconductor to form an electrostatic latent image. And a developing device for developing the electrostatic latent image.
また本発明の有機発光素子は、感光体を露光するための露光装置の構成部材として使用することができる。本発明の有機発光素子を有する露光装置は、例えば、本発明の有機発光素子を所定の方向に沿って列を形成して配置されている露光装置がある。 The organic light-emitting device of the present invention can be used as a constituent member of an exposure apparatus for exposing a photoreceptor. The exposure apparatus having the organic light emitting element of the present invention includes, for example, an exposure apparatus in which the organic light emitting elements of the present invention are arranged in rows along a predetermined direction.
次に、図面を参照しながら本発明の画像表示装置につい説明する。図１は、有機発光素子とこの有機発光素子に接続されるＴＦＴ素子とを有する画像表示装置の例を示す断面模式図である。尚、図１の画像表示装置１を構成する有機発光素子として、本発明の有機発光素子が用いられている。 Next, the image display apparatus of the present invention will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an example of an image display device having an organic light emitting element and a TFT element connected to the organic light emitting element. In addition, the organic light emitting element of this invention is used as an organic light emitting element which comprises the image display apparatus 1 of FIG.
図１の画像表示装置１は、ガラス等の基板１１とその上部にＴＦＴ素子又は有機化合物層を保護するための防湿膜１２が設けられている。また符号１３は金属のゲート電極１３である。符号１４はゲート絶縁膜１４であり、１５は半導体層である。 The image display device 1 in FIG. 1 includes a substrate 11 made of glass or the like and a moisture-proof film 12 for protecting the TFT element or the organic compound layer on the substrate 11. Reference numeral 13 denotes a metal gate electrode 13. Reference numeral 14 denotes a gate insulating film 14 and reference numeral 15 denotes a semiconductor layer.
ＴＦＴ素子１８は、半導体層１５とドレイン電極１６とソース電極１７とを有している。ＴＦＴ素子１８の上部には絶縁膜１９が設けられている。コンタクトホール２０を介して有機発光素子を構成する陽極２１とソース電極１７とが接続されている。 The TFT element 18 includes a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on the TFT element 18. The anode 21 and the source electrode 17 constituting the organic light emitting element are connected via the contact hole 20.
尚、有機発光素子に含まれる電極（陽極、陰極）とＴＦＴに含まれる電極（ソース電極、ドレイン電極）との電気接続の方式は、図１に示される態様に限られるものではない。つまり陽極又は陰極のうちいずれか一方とＴＦＴ素子ソース電極またはドレイン電極のいずれか一方とが電気接続されていればよい。 The method of electrical connection between the electrodes (anode and cathode) included in the organic light emitting element and the electrodes (source electrode and drain electrode) included in the TFT is not limited to the mode shown in FIG. That is, it is only necessary that either one of the anode or the cathode is electrically connected to either the TFT element source electrode or the drain electrode.
図１の画像表示装置１では多層の有機化合物層を１つの層の如く図示をしているが、有機化合物層２２は、複数層であってよい。陰極２３の上には有機発光素子の劣化を抑制するための第一の保護層２４や第二の保護層２５が設けられている。 In the image display device 1 of FIG. 1, the multiple organic compound layers are illustrated as one layer, but the organic compound layer 22 may be a plurality of layers. On the cathode 23, the 1st protective layer 24 and the 2nd protective layer 25 for suppressing deterioration of an organic light emitting element are provided.
図１の画像表示装置１が白色を発する画像表示装置の場合、図１中の有機化合物層２２に含まれる発光層は、赤色発光材料、緑色発光材料及び青色発光材料を混合してなる層としてもよい。また赤色発光材料からなる層、緑色発光材料からなる層、青色発光材料からなる層をそれぞれ積層させてなる積層型の発光層としてもよい。さらに別法として、赤色発光材料からなる層、緑色発光材料からなる層、青色発光材料からなる層を横並びにするなりして一の発光層の中にドメインを形成した態様であってもよい。 When the image display device 1 of FIG. 1 is an image display device that emits white, the light emitting layer included in the organic compound layer 22 in FIG. 1 is a layer formed by mixing a red light emitting material, a green light emitting material, and a blue light emitting material. Also good. Alternatively, a layered light emitting layer in which a layer made of a red light emitting material, a layer made of a green light emitting material, and a layer made of a blue light emitting material are laminated may be used. Furthermore, as another method, a mode in which a layer is formed in one light emitting layer by arranging a layer made of a red light emitting material, a layer made of a green light emitting material, and a layer made of a blue light emitting material side by side.
図１の画像表示装置１ではスイッチング素子としてトランジスタを使用しているが、これに代えてＭＩＭ素子をスイッチング素子として用いてもよい。 In the image display device 1 of FIG. 1, a transistor is used as a switching element, but an MIM element may be used as a switching element instead.
また図１の画像表示装置１に使用されるトランジスタは、単結晶シリコンウエハを用いたトランジスタに限らず、基板の絶縁性表面上に活性層を有する薄膜トランジスタでもよい。活性層として単結晶シリコンを用いた薄膜トランジスタ、活性層としてアモルファスシリコンや微結晶シリコンなどの非単結晶シリコンを用いた薄膜トランジスタ、活性層としてインジウム亜鉛酸化物やインジウムガリウム亜鉛酸化物等の非単結晶酸化物半導体を用いた薄膜トランジスタであってもよい。尚、薄膜トランジスタはＴＦＴ素子とも呼ばれる。 1 is not limited to a transistor using a single crystal silicon wafer, but may be a thin film transistor having an active layer on an insulating surface of a substrate. Thin film transistor using single crystal silicon as active layer, thin film transistor using non-single crystal silicon such as amorphous silicon or microcrystalline silicon as active layer, non-single crystal oxidation such as indium zinc oxide or indium gallium zinc oxide as active layer A thin film transistor using a physical semiconductor may be used. The thin film transistor is also called a TFT element.
図１の画像表示装置１に含まれるトランジスタは、Ｓｉ基板等の基板内に形成されていてもよい。ここで基板内に形成されるとは、Ｓｉ基板等の基板自体を加工してトランジスタを作製することを意味する。つまり、基板内にトランジスタを有することは、基板とトランジスタとが一体に形成されていると見ることもできる。 The transistor included in the image display device 1 of FIG. 1 may be formed in a substrate such as a Si substrate. Here, being formed in the substrate means that a transistor is manufactured by processing the substrate itself such as a Si substrate. In other words, having a transistor in a substrate can be regarded as the substrate and the transistor being integrally formed.
基板内にトランジスタを設けるかどうかについては、精細度によって選択される。例えば１インチでＱＶＧＡ程度の精細度の場合はＳｉ基板内に有機発光素子を設けることが好ましい。 Whether or not the transistor is provided in the substrate is selected depending on the definition. For example, in the case of a definition of about 1 inch and QVGA, it is preferable to provide an organic light emitting element in the Si substrate.
以下、本発明について実施例を用いて詳細に説明する。なお本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described in detail with reference to examples. The present invention is not limited to these.
（実施例１）［例示化合物Ａ−１の合成］
以下に示す合成スキームにより合成した。
Example 1 Synthesis of Exemplary Compound A-1
The synthesis was performed according to the following synthesis scheme.
中間体ＭｅＰＰの合成 Synthesis of intermediate MePP
ディーンスタークトラップを備えた５０ｍｌの二口ナスフラスコに、２−ピコリルアミン ２．０ｇ（１８．５ｍｍｏｌ）、アセチルアセトン １．６ｇ（１６．４ｍｍｏｌ）、ｐ−トルエンスルホン酸一水和物 ０，３１ｇ（１．６４ｍｍｏｌ）、キシレン ３０ｍｌを投入し、１７０℃で撹拌した。反応終了後、冷却しシリカゲルカラムクロマトグラフィー（展開溶媒：酢酸エチル／ヘプタン＝１／５）にて精製し、中間体ＭｅＰＰを２．４４ｇ（収率：８９．７％）得た。 In a 50 ml two-necked eggplant flask equipped with a Dean-Stark trap, 2.0 g (18.5 mmol) of 2-picolylamine, 1.6 g (16.4 mmol) of acetylacetone, 0,31 g of p-toluenesulfonic acid monohydrate ( 1.64 mmol) and 30 ml of xylene were added and stirred at 170 ° C. After completion of the reaction, the reaction mixture was cooled and purified by silica gel column chromatography (developing solvent: ethyl acetate / heptane = 1/5) to obtain 2.44 g of intermediate MePP (yield: 89.7%).
例示化合物Ａ−１の合成 Synthesis of exemplary compound A-1
３０ｍｌ二口フラスコに、中間体ＭｅＰＰを４００ｍｇ（２．３５ｍｍｏｌ）、フェナントロリンを４２３ｍｇ（２．３５ｍｍｏｌ）、トルエン１０ｍｌを投入し、室温で撹拌した。続いて、この溶液にｔＢｕＯＬｉを１８８ｍｇ（２．３５ｍｍｏｌ）投入し、８０℃で６時間撹拌した。撹拌終了後、ろ過を行い例示化合物Ａ−１を３６０ｍｇ（収率：４２．９％）得た。さらに、昇華精製を行い、Ａ−１の昇華精製品を２３０ｍｇ得た。
質量分析法により、例示化合物Ａ−１のＭ＋である３５８を確認した。
A 30 ml two-necked flask was charged with 400 mg (2.35 mmol) of the intermediate MePP, 423 mg (2.35 mmol) of phenanthroline, and 10 ml of toluene, and stirred at room temperature. Subsequently, 188 mg (2.35 mmol) of tBuOLi was added to this solution and stirred at 80 ° C. for 6 hours. After the stirring, filtration was performed to obtain 360 mg (yield: 42.9%) of Exemplary Compound A-1. Furthermore, sublimation purification was performed to obtain 230 mg of A-1 sublimation purified product.
358 which is M + of exemplary compound A-1 was confirmed by mass spectrometry.
また、１ＨＮＭＲ測定により、例示化合物Ａ−１の構造を確認した。
１Ｈ ＮＭＲ（ｄ６−ＤＭＳＯ，５００ＭＨｚ） σ（ｐｐｍ）：９．１１（ｄ，２Ｈ），８．５０（ｄ，２Ｈ），８．２１（ｓ，１Ｈ），８．００（ｄ，２Ｈ），７．７８（ｄｄ，２Ｈ），７．５４（ｔ，１Ｈ），７．３３（ｔ，１Ｈ），６．７６（ｄ，１Ｈ），５．５９（ｓ，１Ｈ），２．２５（ｓ，３Ｈ），２．１２（ｓ，３Ｈ）
Moreover, the structure of exemplary compound A-1 was confirmed by 1 HNMR measurement.
1 H NMR (d6-DMSO, 500 MHz) σ (ppm): 9.11 (d, 2H), 8.50 (d, 2H), 8.21 (s, 1H), 8.00 (d, 2H) , 7.78 (dd, 2H), 7.54 (t, 1H), 7.33 (t, 1H), 6.76 (d, 1H), 5.59 (s, 1H), 2.25 ( s, 3H), 2.12 (s, 3H)
次に、５０ｍｌビーカーに化合物Ａ−１を２００ｍｇ、水を１０ｍｌ混合し、室温にて一晩放置したが、変化がなかった。同様に、参考までに下記構造式で示す参考例化合物を２００ｍｇ、水を１０ｍｌ混合したが、混合した瞬間に分解してしまった。 Next, 200 mg of compound A-1 and 10 ml of water were mixed in a 50 ml beaker and left at room temperature overnight, but there was no change. Similarly, for reference, 200 mg of a reference example compound represented by the following structural formula and 10 ml of water were mixed, but they were decomposed at the moment of mixing.
例示化合物Ａ−１の耐水性試験
石英基板（６５ｍｍ×３０ｍｍ）を真空蒸着装置（株式会社アルバック製）にセットし、抵抗加熱による真空蒸着によって、例示化合物Ａ−１からなる薄膜を成膜した。このとき真空チャンバー内の圧力条件を１×１０−５Ｐａとし、当該薄膜の膜厚を１５０ｎｍとした。
Water Resistance Test of Illustrative Compound A-1 A quartz substrate (65 mm × 30 mm) was set in a vacuum vapor deposition apparatus (manufactured by ULVAC, Inc.), and a thin film composed of Illustrative compound A-1 was formed by vacuum vapor deposition using resistance heating. At this time, the pressure condition in the vacuum chamber was 1 × 10 −5 Pa, and the thickness of the thin film was 150 nm.
次に、例示化合物Ａ−１を成膜した石英基板（薄膜付基板）を、６０分間、純水を入れたシャーレの中に浸漬し放置した。次に、純水に浸漬した薄膜付基板を、光学顕微鏡（オリンパス社製、ＭＸ−８０）を用いて観察した結果、浸漬の前後において膜の状態が特に変化していないことを確認した。 Next, the quartz substrate (substrate with a thin film) on which Example Compound A-1 was formed was immersed in a petri dish containing pure water for 60 minutes and allowed to stand. Next, as a result of observing the substrate with a thin film immersed in pure water using an optical microscope (manufactured by Olympus Corporation, MX-80), it was confirmed that the state of the film was not particularly changed before and after the immersion.
次に、純水に浸漬した薄膜付基板について、吸光光度計（日立分光光度計Ｕ−２８１０）を用いて、吸収波長３５０ｎｍにおける吸光度を測定し、予め測定しておいた浸漬前の薄膜付基板での測定値と比較した結果、変化率は５％であった。また膜厚測定器（ＫＬＡ Ｔｅｎｃｏｒ社製、Ｐ−１６）を用いて、浸漬前後の薄膜の膜厚を測定したところ、膜厚が変化していないことが確認された。 Next, with respect to the substrate with a thin film immersed in pure water, the absorbance at an absorption wavelength of 350 nm was measured using an absorptiometer (Hitachi spectrophotometer U-2810), and the substrate with a thin film before immersion that had been measured in advance was measured. As a result of comparison with the measured value, the rate of change was 5%. Moreover, when the film thickness of the thin film before and behind immersion was measured using the film thickness measuring device (K-16 made by KLA Tencor, P-16), it was confirmed that the film thickness did not change.
（実施例２）［例示化合物Ａ−１３の合成］
以下に示す合成スキームにより合成した。
Example 2 [Synthesis of Exemplified Compound A-13]
The synthesis was performed according to the following synthesis scheme.
中間体ＰｈＰＰの合成 Synthesis of intermediate PhPP
ディーンスタークトラップを備えた５０ｍｌの二口ナスフラスコに、２−ピコリルアミン １．０８ｇ（１０．０ｍｍｏｌ）、１，３−ジフェニル−１，３−プロパンジオン ２．０ｇ（８．９２ｍｍｏｌ）、ｐ−トルエンスルホン酸一水和物 ０．１７ｇ（８．９２ｍｍｏｌ）、キシレン ４０ｍｌを投入し、１７０℃で撹拌した。反応終了後、冷却しシリカゲルカラムクロマトグラフィー（展開溶媒：酢酸エチル／ヘプタン＝１／５）にて精製し、中間体ＭｅＰＰを１．６３ｇ（収率：６１．７％）得た。 In a 50 ml two-necked eggplant flask equipped with a Dean-Stark trap, 1.08 g (10.0 mmol) of 2-picolylamine, 2.0 g (8.92 mmol) of 1,3-diphenyl-1,3-propanedione, p- Toluenesulfonic acid monohydrate 0.17 g (8.92 mmol) and xylene 40 ml were added and stirred at 170 ° C. After completion of the reaction, the reaction mixture was cooled and purified by silica gel column chromatography (developing solvent: ethyl acetate / heptane = 1/5) to obtain 1.63 g (yield: 61.7%) of intermediate MePP.
例示化合物Ａ−１３の合成 Synthesis of exemplary compound A-13
３０ｍｌ二口フラスコに、中間体ＰｈＰＰを５００ｍｇ（１．６９ｍｍｏｌ）、フェナントロリンを３００ｍｇ（１．６９ｍｍｏｌ）、トルエン１０ｍｌを投入し、室温で撹拌した。続いて、この溶液にｔＢｕＯＬｉを１４０ｍｇ（１．６９ｍｍｏｌ）投入し、８０℃で６時間撹拌した。撹拌終了後、ろ過を行い例示化合物Ａ−１３を４６０ｍｇ（収率：５６．５％）得た。さらに、昇華精製を行い、Ａ−１３の昇華精製品を３００ｍｇ得た。
質量分析法により、例示化合物Ａ−１３のＭ＋である４８３を確認した。
A 30 ml two-necked flask was charged with 500 mg (1.69 mmol) of intermediate PhPP, 300 mg (1.69 mmol) of phenanthroline, and 10 ml of toluene, and stirred at room temperature. Subsequently, 140 mg (1.69 mmol) of tBuOLi was added to this solution and stirred at 80 ° C. for 6 hours. After the stirring, filtration was performed to obtain 460 mg (yield: 56.5%) of Exemplary Compound A-13. Furthermore, sublimation purification was performed to obtain 300 mg of A-13 sublimation purified product.
By mass spectrometry, 483 which was M + of the exemplary compound A-13 was confirmed.
また、１ＨＮＭＲ測定により、例示化合物Ａ−１３の構造を確認した。
１Ｈ ＮＭＲ（ｄ６−ＤＭＳＯ，５００ＭＨｚ） σ（ｐｐｍ）：９．１１（ｄ，２Ｈ），８．５０（ｄ，２Ｈ），８．３３（ｂｒ，１Ｈ），８．００（ｄ，２Ｈ），７．８２（ｄ，２Ｈ）７．７８（ｄｄ，２Ｈ），７．４５（ｂｒ，１Ｈ），７．３８（ｄ，２Ｈ），７．００−７．３２（ｍ，８Ｈ），６．５６（ｓ，１Ｈ）
次に、５０ｍｌビーカーに化合物Ａ−１３を２００ｍｇ、水を１０ｍｌ混合し、室温にて一晩放置したが、変化がなかった。
Moreover, the structure of exemplary compound A-13 was confirmed by 1 HNMR measurement.
1 H NMR (d6-DMSO, 500 MHz) σ (ppm): 9.11 (d, 2H), 8.50 (d, 2H), 8.33 (br, 1H), 8.00 (d, 2H) 7.82 (d, 2H) 7.78 (dd, 2H), 7.45 (br, 1H), 7.38 (d, 2H), 7.00-7.32 (m, 8H), 6 .56 (s, 1H)
Next, 200 mg of compound A-13 and 10 ml of water were mixed in a 50 ml beaker and left at room temperature overnight, but there was no change.
例示化合物Ａ−１３の耐水性試験
石英基板（６５ｍｍ×３０ｍｍ）を真空蒸着装置（株式会社アルバック製）にセットし、抵抗加熱による真空蒸着によって、例示化合物Ａ−１３からなる薄膜を成膜した。このとき真空チャンバー内の圧力条件を１×１０−５Ｐａとし、当該薄膜の膜厚を１５０ｎｍとした。
Water resistance test of Exemplified Compound A-13 A quartz substrate (65 mm × 30 mm) was set in a vacuum vapor deposition apparatus (manufactured by ULVAC, Inc.), and a thin film made of Exemplified Compound A-13 was formed by vacuum evaporation by resistance heating. At this time, the pressure condition in the vacuum chamber was 1 × 10 −5 Pa, and the thickness of the thin film was 150 nm.
次に、例示化合物Ａ−１３を成膜した石英基板（薄膜付基板）を、６０分間、純水を入れたシャーレの中に浸漬し放置した。次に、純水に浸漬した薄膜付基板を、光学顕微鏡（オリンパス社製、ＭＸ−８０）を用いて観察した結果、浸漬の前後において膜の状態が特に変化していないことを確認した。 Next, the quartz substrate (substrate with a thin film) on which Example Compound A-13 was formed was immersed in a petri dish containing pure water for 60 minutes and allowed to stand. Next, as a result of observing the substrate with a thin film immersed in pure water using an optical microscope (manufactured by Olympus Corporation, MX-80), it was confirmed that the state of the film was not particularly changed before and after the immersion.
次に、純水に浸漬した薄膜付基板について、吸光光度計（日立分光光度計Ｕ−２８１０）を用いて、吸収波長３５０ｎｍにおける吸光度を測定し、予め測定しておいた浸漬前の薄膜付基板での測定値と比較した結果、変化率は５％であった。また膜厚測定器（ＫＬＡ Ｔｅｎｃｏｒ社製、Ｐ−１６）を用いて、浸漬前後の薄膜の膜厚を測定したところ、膜厚が変化していないことが確認された。 Next, with respect to the substrate with a thin film immersed in pure water, the absorbance at an absorption wavelength of 350 nm was measured using an absorptiometer (Hitachi spectrophotometer U-2810), and the substrate with a thin film before immersion that had been measured in advance was measured. As a result of comparison with the measured value, the rate of change was 5%. Moreover, when the film thickness of the thin film before and behind immersion was measured using the film thickness measuring device (K-16 made by KLA Tencor, P-16), it was confirmed that the film thickness did not change.
（実施例３）［例示化合物Ａ−２０の合成］
実施例２と同様にして、フェナントロリンを以下の化合物Ｂｐｈｅｎに変えて、例示化合物Ａ−２０を合成した。
(Example 3) [Synthesis of Exemplified Compound A-20]
Exemplified compound A-20 was synthesized in the same manner as in Example 2 except that phenanthroline was changed to the following compound Bphen.
質量分析法により、例示化合物Ａ−２０のＭ＋である６３５を確認した。また、実施例２と同様の耐水試験を実施し耐水性があることを確認した。 By mass spectrometry, 635 which was M + of the exemplary compound A-20 was confirmed. Moreover, the water resistance test similar to Example 2 was implemented, and it confirmed that there was water resistance.
（実施例４）［例示化合物Ｂ−１合成］
実施例１と同様にして、フェナントロリンを以下の化合物Ｂｐｙに変えて、例示化合物Ｂ−１を合成した。
Example 4 Synthesis of Exemplary Compound B-1
Exemplified compound B-1 was synthesized in the same manner as in Example 1, except that phenanthroline was changed to the following compound Bpy.
質量分析法により、例示化合物Ｂ−１のＭ＋である３３４を確認した。また、実施例１と同様の耐水試験を実施し耐水性があることを確認した。 By mass spectrometry, 334, which was M + of the exemplary compound B-1, was confirmed. Moreover, the water resistance test similar to Example 1 was implemented, and it confirmed that there was water resistance.
（実施例５）［例示化合物Ｂ−１３合成］
実施例２と同様にして、フェナントロリンを以下の化合物Ｂｐｙに変えて、例示化合物Ｂ−１３を合成した。
Example 5 Synthesis of Exemplified Compound B-13
Exemplified compound B-13 was synthesized in the same manner as in Example 2 except that phenanthroline was changed to the following compound Bpy.
質量分析法により、例示化合物Ｂ−１３のＭ＋である４５８を確認した。また、実施例２と同様の耐水試験を実施し耐水性があることを確認した。 By mass spectrometry, 458 which was M + of the exemplary compound B-13 was confirmed. Moreover, the water resistance test similar to Example 2 was implemented, and it confirmed that there was water resistance.
（実施例６）［例示化合物Ｂ−５合成］
実施例１と同様にして、フェナントロリンを以下の化合物Ｍｂｐｙに変えて、例示化合物Ｂ−５を合成した。
Example 6 Synthesis of Exemplary Compound B-5
Exemplified Compound B-5 was synthesized in the same manner as Example 1 except that phenanthroline was changed to the following compound Mbpy.
質量分析法により、例示化合物Ｂ−５のＭ＋である３６２を確認した。また、実施例１と同様の耐水試験を実施し耐水性があることを確認した。 By mass spectrometry, 362 as M + of Exemplified Compound B-5 was confirmed. Moreover, the water resistance test similar to Example 1 was implemented, and it confirmed that there was water resistance.
（実施例７）［例示化合物Ｂ−２１の合成］
実施例２と同様にして、フェナントロリンを以下の化合物ｔＢｕｂｐｙに変えて、例示化合物Ｂ−２１を合成した。
(Example 7) [Synthesis of Exemplified Compound B-21]
Exemplified compound B-21 was synthesized in the same manner as in Example 2, except that phenanthroline was changed to the following compound tBubpy.
質量分析法により、例示化合物Ｂ−２１のＭ＋である５７１を確認した。また、実施例２と同様の耐水試験を実施し耐水性があることを確認した。 By mass spectrometry, 571 which was M + of the exemplary compound B-21 was confirmed. Moreover, the water resistance test similar to Example 2 was implemented, and it confirmed that there was water resistance.
（実施例８）［例示化合物Ａ−１の有機発光素子］
本実施例では、基板上に、陽極、ホール注入層、発光層、電子輸送層、電子注入層、陰極が順次形成された有機発光素子を作製した。
Example 8 [Organic Light-Emitting Device of Exemplary Compound A-1]
In this example, an organic light emitting device was fabricated in which an anode, a hole injection layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate.
まずガラス基板上に、ＩＴＯを成膜し、所望のパターニング加工を施すことによりＩＴＯ電極（陽極）を形成した。このときＩＴＯ電極の膜厚を１００ｎｍとした。このようにＩＴＯ電極が形成された基板をＩＴＯ基板として、以下の工程で使用した。 First, an ITO film was formed on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps.
上記ＩＴＯ基板上に、下記表１に示す有機化合物層及び電極層を連続成膜した。尚、このとき対向する電極（電極層、陰極）の電極面積が３ｍｍ２となるようにし、吸湿剤による封止を行った。 On the ITO substrate, organic compound layers and electrode layers shown in Table 1 below were continuously formed. At this time, the electrode area of the opposing electrodes (electrode layer, cathode) was set to 3 mm 2 and sealing with a hygroscopic agent was performed.
得られた素子について、素子の特性を測定・評価した。ＩＴＯ電極を正極、Ａｌ電極を負極にして電圧を印加したところ、最大発光効率が３．０ｃｄ／Ａの赤色発光が観測された。また、得られた素子の安定性を評価するために、３０００ｃｄ／ｍ２の初期輝度で駆動させた時の輝度が５０％減少する寿命を測定したところ５００時間を越えた。測定装置は、具体的には電流電圧特性をヒューレッドパッカード社製・微小電流計４１４０Ｂで測定し、発光輝度は、トプコン社製ＢＭ７で測定した。 About the obtained element, the characteristic of the element was measured and evaluated. When voltage was applied with the ITO electrode as the positive electrode and the Al electrode as the negative electrode, red light emission with a maximum light emission efficiency of 3.0 cd / A was observed. Further, in order to evaluate the stability of the obtained device, the lifetime at which the luminance was reduced by 50% when measured at an initial luminance of 3000 cd / m 2 was measured and exceeded 500 hours. Specifically, the measuring apparatus measured the current-voltage characteristics with a microammeter 4140B manufactured by Hured Packard, and the emission luminance was measured with BM7 manufactured by Topcon.
また、吸湿剤による封止を行わない有機発光素子でも、赤色発光を確認し、さらに長時間駆動後も変わらず赤色発光することも確認した。 In addition, even in an organic light-emitting element that was not sealed with a hygroscopic agent, red light emission was confirmed, and it was also confirmed that red light emission remained unchanged after being driven for a long time.
（実施例９乃至１９）
実施例８の電子注入層を本発明に係る化合物に、発光層のホスト材料とゲスト材料を適宜変更する以外は、実施例８と同様の方法により有機発光素子を作製した。得られた素子について実施例８と同様に素子の特性を測定・評価したところ、輝度５０％減少寿命はすべて５００時間を越えた。ここで、実施例１３乃至１９は、初期輝度が５０００ｃｄ／ｍ２の輝度半減寿命を評価した。
(Examples 9 to 19)
An organic light emitting device was produced in the same manner as in Example 8 except that the electron injection layer of Example 8 was changed to the compound according to the present invention and the host material and guest material of the light emitting layer were appropriately changed. The device characteristics of the obtained device were measured and evaluated in the same manner as in Example 8. As a result, all the lifetimes with reduced brightness by 50% exceeded 500 hours. Here, Examples 13 to 19 evaluated the luminance half-life with an initial luminance of 5000 cd / m 2.
また、吸湿剤による封止を行わない有機発光素子でも、赤色発光を確認し、さらに長時間駆動後も変わらず発光することも確認した。結果の一部を表２に示す。 In addition, even in an organic light emitting device that is not sealed with a hygroscopic agent, red light emission was confirmed, and it was also confirmed that light was emitted unchanged after being driven for a long time. Some of the results are shown in Table 2.
（比較例１）［実施例１で説明した参考例化合物の有機発光素子］
実施例８の電子注入層を参考例化合物に変更する以外、実施例８と同様の方法により有機発光素子を作製し、吸湿剤による封止を行わなかった。得られた素子について実施例８と同様に素子の特性を測定・評価したところ、最大発光効率が３．０ｃｄ／Ａの赤色発光が観測されたが、特性の測定・評価中に発光面を顕微鏡観察したところ、ダークスポット（非発光エリア）が多数発生していた。従って、素子寿命測定を行うことができなかった。
Comparative Example 1 [Organic Light-Emitting Device of Reference Example Compound Explained in Example 1]
An organic light emitting device was produced in the same manner as in Example 8 except that the electron injection layer in Example 8 was changed to the reference compound, and sealing with a hygroscopic agent was not performed. When the characteristics of the obtained device were measured and evaluated in the same manner as in Example 8, red light emission with a maximum light emission efficiency of 3.0 cd / A was observed. When observed, many dark spots (non-light emitting areas) were generated. Therefore, element lifetime measurement could not be performed.
（実施例２０）［例示化合物Ａ−１の有機発光素子］
本実施例では、表３に示すように、電子注入層を２種類の材料からなる有機発光素子を作製した。素子作製方法は、実施例８と同様の方法で行った。
Example 20 [Organic Light-Emitting Element of Illustrative Compound A-1]
In this example, as shown in Table 3, an organic light-emitting element composed of two types of materials for the electron injection layer was produced. The element manufacturing method was performed in the same manner as in Example 8.
得られた素子について、素子の特性を測定・評価した。ＩＴＯ電極を正極、Ａｌ電極を負極にして電圧を印加したところ、最大発光効率が３．０ｃｄ／Ａの赤色発光が観測された。また、得られた素子の安定性を評価するために、３０００ｃｄ／ｍ２の初期輝度で駆動させた時の輝度が５０％減少する寿命を測定したところ５００時間を越えた。測定装置は、具体的には電流電圧特性をヒューレッドパッカード社製・微小電流計４１４０Ｂで測定し、発光輝度は、トプコン社製ＢＭ７で測定した。 About the obtained element, the characteristic of the element was measured and evaluated. When voltage was applied with the ITO electrode as the positive electrode and the Al electrode as the negative electrode, red light emission with a maximum light emission efficiency of 3.0 cd / A was observed. Further, in order to evaluate the stability of the obtained device, the lifetime at which the luminance was reduced by 50% when measured at an initial luminance of 3000 cd / m 2 was measured and exceeded 500 hours. Specifically, the measuring apparatus measured the current-voltage characteristics with a microammeter 4140B manufactured by Hured Packard, and the emission luminance was measured with BM7 manufactured by Topcon.
また、吸湿剤による封止を行わない有機発光素子でも、赤色発光を確認し、さらに長時間駆動後も変わらず赤色発光することも確認した。 In addition, even in an organic light-emitting element that was not sealed with a hygroscopic agent, red light emission was confirmed, and it was also confirmed that red light emission remained unchanged after being driven for a long time.
（実施例２１乃至２４）
実施例２０の電子注入層のゲスト材料を適宜変更する以外は、実施例２０と同様の方法により有機発光素子を作製した。得られた素子について実施例２０と同様に素子の特性を測定・評価したところ、輝度５０％減少寿命はすべて５００時間を越えた。
(Examples 21 to 24)
An organic light-emitting device was produced in the same manner as in Example 20 except that the guest material for the electron injection layer in Example 20 was changed as appropriate. When the characteristics of the obtained device were measured and evaluated in the same manner as in Example 20, the brightness reduced lifetime by 50% exceeded all 500 hours.
また、吸湿剤による封止を行わない有機発光素子でも、赤色発光を確認し、さらに長時間駆動後も変わらず発光することも確認した。結果の一部を表４に示す。 In addition, even in an organic light emitting device that is not sealed with a hygroscopic agent, red light emission was confirmed, and it was also confirmed that light was emitted unchanged after being driven for a long time. A part of the results is shown in Table 4.
＜結果と考察＞
実施例１乃至７より、本発明の新規リチウム錯体は、耐水性があることが確認された。また、実施例８乃至２４より、特定のリチウム錯体を有する有機発光素子は、長時間駆動が可能であることも確認された。
<Results and discussion>
From Examples 1 to 7, it was confirmed that the novel lithium complex of the present invention has water resistance. Further, from Examples 8 to 24, it was confirmed that the organic light-emitting device having a specific lithium complex can be driven for a long time.
以上実施形態や実施例をあげて説明したように、式１で示す有機化合物を有する有機発光素子は、長時間の使用による経時変化を引き起こす原因の一つとされる湿気による劣化等に耐える素子である。 As described above with reference to the embodiments and examples, the organic light-emitting element having the organic compound represented by Formula 1 is an element that can withstand deterioration due to moisture, which is one of the causes of changes over time due to long-term use. is there.
本発明のリチウム錯体は、耐水性という観点で優れた化合物である。特に、この錯体を、有機発光素子を構成する電子注入層に含ませることで、良好な発光特性を有する有機発光素子を得ることができる。従って、本発明の有機発光素子は、画像表示装置、画像情報処理装置、照明装置、電子写真方式の画像形成装置及び露光装置に含まれる構成部材（デバイス）として利用することができる。 The lithium complex of the present invention is an excellent compound from the viewpoint of water resistance. In particular, by including this complex in the electron injection layer constituting the organic light emitting device, an organic light emitting device having good light emitting characteristics can be obtained. Therefore, the organic light emitting device of the present invention can be used as a component (device) included in an image display device, an image information processing device, an illumination device, an electrophotographic image forming device, and an exposure device.
１８ ＴＦＴ素子
２１ 陽極
２２ 有機化合物層
２３ 陰極
18 TFT element 21 Anode 22 Organic compound layer 23 Cathode
Claims (15)
（式［１］、［２］において、Ｒ１〜Ｒ１０は、水素原子、直鎖または分岐状の炭素原子数１乃至４のアルキル基、置換あるいは無置換のアリール基、からそれぞれ独立に選ばれる。） An organic compound represented by any one of the following general formulas [1] and [2].
(In the formulas [1] and [2], R1 to R10 are each independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group. )
（式［３］において、Ｒ１１〜Ｒ１６は、水素原子、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、フェニル基、ナフチル基、フルオレニル基、フェナンスリル基、からそれぞれ独立に選ばれる。） The organic compound according to claim 1, wherein the organic compound is the compound represented by the general formula [1], and further represented by the following general formula [3].
(In Formula [3], R11 to R16 are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, and a phenanthryl group.)
（式［４］において、Ｒ１７〜Ｒ２４は、水素原子、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、フェニル基、ナフチル基、フルオレニル基、フェナンスリル基、からそれぞれ独立に選ばれる。） The organic compound according to claim 1, wherein the organic compound is the compound represented by the general formula [2], and further represented by the following general formula [4].
(In Formula [4], R17 to R24 are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a fluorenyl group, and a phenanthryl group.)
前記画素が、請求項４乃至７のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続されている能動素子と、を有することを特徴とする、画像表示装置。 Having a plurality of pixels,
An image display device, wherein the pixel includes the organic light-emitting element according to claim 4 and an active element connected to the organic light-emitting element.
画像情報を入力するための入力部と、を有し、
前記表示部が、請求項８に記載の画像表示装置であることを特徴とする、画像情報処理装置。 A display for displaying an image;
An input unit for inputting image information,
An image information processing apparatus, wherein the display unit is the image display apparatus according to claim 8.
前記有機発光素子に接続されているＡＣ／ＤＣコンバーター回路と、を有することを特徴とする、照明装置。 An organic light emitting device according to any one of claims 4 to 7,
And an AC / DC converter circuit connected to the organic light emitting element.
前記感光体を露光する露光部と、
を有し、
前記露光部が、請求項４乃至７のいずれか一項に記載の有機発光素子を有することを特徴とする、電子写真方式の画像形成装置。 A photoreceptor,
An exposure unit for exposing the photoreceptor;
Have
An electrophotographic image forming apparatus, wherein the exposure unit includes the organic light-emitting element according to claim 4.
前記露光装置が、請求項１乃至７のいずれか一項に記載の有機発光素子を有し、
前記有機発光素子が、所定の方向に列を形成して配置されていることを特徴とする、露光装置。 An exposure apparatus for exposing a photoreceptor,
The exposure apparatus has the organic light emitting element according to any one of claims 1 to 7,
An exposure apparatus, wherein the organic light emitting elements are arranged in rows in a predetermined direction.
請求項７に記載の有機発光素子と、
カラーフィルターを有し、
前記発光層は白色光を発する画像表示装置。 A substrate,
An organic light emitting device according to claim 7,
Have a color filter,
The light emitting layer is an image display device that emits white light.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014099898A JP2015214526A (en) | 2014-05-13 | 2014-05-13 | Novel organic compound and organic light emitting element having the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014099898A JP2015214526A (en) | 2014-05-13 | 2014-05-13 | Novel organic compound and organic light emitting element having the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2015214526A true JP2015214526A (en) | 2015-12-03 |
Family
ID=54751776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014099898A Pending JP2015214526A (en) | 2014-05-13 | 2014-05-13 | Novel organic compound and organic light emitting element having the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2015214526A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105820178A (en) * | 2016-04-22 | 2016-08-03 | 山西大学 | Amino pyrrole metal lithium compound as well as preparation method and application thereof |
-
2014
- 2014-05-13 JP JP2014099898A patent/JP2015214526A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105820178A (en) * | 2016-04-22 | 2016-08-03 | 山西大学 | Amino pyrrole metal lithium compound as well as preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101612650B1 (en) | Novel organic compound, organic light-emitting device, and display apparatus | |
| CN104871333B (en) | Organic illuminating element and display device | |
| JP5777408B2 (en) | Fused polycyclic compound and organic light emitting device using the same | |
| JP2012082187A (en) | New condensed polycyclic compound, and organic light-emitting element having the same | |
| KR20100092472A (en) | Luminescent-element material and luminescent element | |
| RU2477266C1 (en) | Novel organic compound and organic light-emitting device | |
| WO2012086366A1 (en) | Fused polycyclic compound and organic light emitting device using the same | |
| JP4880450B2 (en) | Organometallic complex, luminescent solid, organic EL device and organic EL display | |
| JP2003336043A (en) | Material for light-emitting device and light-emitting device using it | |
| JP5627300B2 (en) | Novel organic compound and organic light emitting device having the same | |
| JP2015115331A (en) | Organic light-emitting element and display device | |
| JP5783879B2 (en) | Novel organic compounds and organic light emitting devices | |
| JP2014086463A (en) | Novel fused polycyclic compound | |
| JP5679789B2 (en) | Novel organic compound and organic light emitting device having the same | |
| JP5721533B2 (en) | Dispirodibenzonaphthacene compound and organic light-emitting device using the same | |
| WO2011018951A1 (en) | Pyrene derivative and organic light-emitting device using the same | |
| JP2014051448A (en) | NAPHTHO[1,2-b]TRIPHENYLENE COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT HAVING THE SAME | |
| JP5495606B2 (en) | Novel condensed polycyclic compound and organic light emitting device having the same | |
| JP2015212243A (en) | Novel organic compound and organic light-emitting element having the same | |
| JP5836771B2 (en) | Novel organic compound and organic light emitting device having the same | |
| JP2015214526A (en) | Novel organic compound and organic light emitting element having the same | |
| JP5751990B2 (en) | Novel condensed polycyclic compound and organic light emitting device having the same | |
| JP2012092047A (en) | Pyrazoloindole compound, and organic light emitting element employing the same | |
| JP2013049651A (en) | Condensed polycyclic compound and organic light-emitting element having the same | |
| JP5534705B2 (en) | Novel condensed polycyclic compounds and organic light emitting devices |