JP2010263065A - Organic light-emitting element - Google Patents
Organic light-emitting element Download PDFInfo
- Publication number
- JP2010263065A JP2010263065A JP2009112499A JP2009112499A JP2010263065A JP 2010263065 A JP2010263065 A JP 2010263065A JP 2009112499 A JP2009112499 A JP 2009112499A JP 2009112499 A JP2009112499 A JP 2009112499A JP 2010263065 A JP2010263065 A JP 2010263065A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- light emitting
- formula
- condensed polycyclic
- 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.)
- Withdrawn
Links
- -1 benzo terphenyls Chemical class 0.000 claims abstract description 138
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- 125000005581 pyrene group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000101 thioether group Chemical group 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 61
- 239000000463 material Substances 0.000 description 25
- 239000010408 film Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000758 substrate Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 239000000470 constituent Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 150000008376 fluorenones Chemical class 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000006384 methylpyridyl group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 2
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 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
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 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
- 229920002050 silicone resin Polymers 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
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- AKJYCUBHAHKANS-UHFFFAOYSA-N 18,19-diphenylpentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),2(11),3,5,7,9,12,14,16,18-decaene Chemical group C1=CC=CC=C1C1=CC2=CC=CC(C=3C4=C5C=CC=CC5=CC=3)=C2C4=C1C1=CC=CC=C1 AKJYCUBHAHKANS-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical class 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 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
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 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
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 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
- 239000000113 methacrylic resin Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 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
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical class C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000011135 tin Substances 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
本発明は、有機発光素子に関する。 The present invention relates to an organic light emitting device.
有機発光素子は、陽極と陰極との間に蛍光性有機化合物を含む薄膜を挟持させてなる電子素子である。また各電極から電子及びホール（正孔）を注入することにより、蛍光性有機化合物の励起子が生成され、この励起子が基底状態に戻る際に、有機発光素子は光を発する。 An organic light emitting device is an electronic device in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode. Further, by injecting electrons and holes from each electrode, excitons of the fluorescent organic compound are generated, and the organic light emitting element emits light when the excitons return to the ground state.
近年、有機発光素子における進歩は著しく、その特徴として、低電圧で高輝度、発光波長の多様性、高速応答性、発光デバイスの薄型化・軽量化が可能であることが挙げられる。 2. Description of the Related Art In recent years, organic light-emitting devices have made remarkable progress, and their features include low voltage, high brightness, a variety of emission wavelengths, high-speed response, and light-emitting devices that can be made thinner and lighter.
しかし、フルカラーディスプレイ等への応用を考えた場合、現在有機発光素子が有する発光効率、安定性ではまだ不十分であり、さらなる改良が必要である。 However, when considering application to a full-color display or the like, the light emission efficiency and stability of the organic light-emitting element are still insufficient, and further improvement is necessary.
そこでさらなる素子特性の向上を目的としてさまざまな研究が行われている。例えば、特許文献１では、発光層の構成材料、より具体的には発光層のドーパントとして、ペリフルオランテン骨格を有する有機化合物を使用した有機発光素子が開示されている。また特許文献２では、発光層をナフタセン誘導体とインデノペリレン誘導体との混合物で構成した有機発光素子が開示されている。 Therefore, various studies have been conducted for the purpose of further improving device characteristics. For example, Patent Document 1 discloses an organic light-emitting device using an organic compound having a perfluoranthene skeleton as a constituent material of the light-emitting layer, more specifically, as a dopant of the light-emitting layer. Patent Document 2 discloses an organic light-emitting device in which a light-emitting layer is composed of a mixture of a naphthacene derivative and an indenoperylene derivative.
本発明は、上述した従来技術の問題点を解決するためになされたものであり、その目的は、耐久性に優れた有機発光素子を提供することである。 The present invention has been made to solve the above-described problems of the prior art, and an object of the present invention is to provide an organic light emitting device having excellent durability.
本発明の有機発光素子は、陽極と陰極と、
該陽極と該陰極との間に挟持され少なくとも発光層を有する有機化合物層と、から構成され、
該発光層に下記一般式［１］で示される縮合多環化合物と、下記一般式［２］で示される縮合多環化合物とが含まれることを特徴とする。
The organic light-emitting device of the present invention comprises an anode, a cathode,
An organic compound layer sandwiched between the anode and the cathode and having at least a light emitting layer,
The light emitting layer contains a condensed polycyclic compound represented by the following general formula [1] and a condensed polycyclic compound represented by the following general formula [2].
本発明によれば、耐久性に優れた有機発光素子を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the organic light emitting element excellent in durability 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.
本発明の有機発光素子は、陽極と陰極と、該陽極と該陰極との間に挟持され少なくとも発光層を有する有機化合物層と、から構成される。 The organic light emitting device of the present invention comprises an anode, a cathode, and an organic compound layer sandwiched between the anode and the cathode and having at least a light emitting layer.
以下、図面を参照しながら本発明の有機発光素子について詳細に説明する。 Hereinafter, the organic light emitting device of the present invention will be described in detail with reference to the drawings.
図１は、本発明の有機発光素子における実施形態の一例を示す断面外略図である。図１の有機発光素子１０は、基板１上に、陽極２、ホール輸送層３、発光層４、電子輸送層５及び陰極６がこの順に積層されている。
FIG. 1 is a schematic cross-sectional view illustrating an example of an embodiment of the organic light-emitting device of the present invention. In the organic
ただし、図１はあくまでごく基本的な素子構成であり、本発明の有機発光素子の構成はこれに限定されるものではない。例えば、電極と有機化合物層との界面に絶縁性層、接着層又は干渉層を設ける、正孔輸送層がイオン化ポテンシャルの異なる２層から構成される等多様な層構成をとることができる。 However, FIG. 1 is a very basic element structure, and the structure of the organic light-emitting element of the present invention is not limited to this. For example, various layer configurations such as providing an insulating layer, an adhesive layer, or an interference layer at the interface between the electrode and the organic compound layer, and a hole transport layer including two layers having different ionization potentials can be employed.
本発明の有機発光素子は、発光層４に下記一般式［１］で示される縮合多環化合物と、下記一般式［２］で示される縮合多環化合物とが含まれている。 In the organic light emitting device of the present invention, the light emitting layer 4 contains a condensed polycyclic compound represented by the following general formula [1] and a condensed polycyclic compound represented by the following general formula [2].
まず一般式［１］で示される縮合多環化合物について説明する。 First, the condensed polycyclic compound represented by the general formula [1] will be described.
式［１］において、Ｒ1乃至Ｒ36は、それぞれ水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアルコキシ基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換のアリールオキシ基、置換アミノ基、ハロゲン原子、スルフィド基及びシリル基からなる群より選ばれる置換基である。 In the formula [1], R 1 to R 36 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, It is a substituent selected from the group consisting of a substituted or unsubstituted aryloxy group, a substituted amino group, a halogen atom, a sulfide group and a silyl group.
Ｒ1乃至Ｒ36で表されるアルキル基として、メチル基、メチル−ｄ１基、メチル−ｄ３基、エチル基、エチル−ｄ５基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−デシル基、ｉｓｏ−プロピル基、ｉｓｏ−プロピル−ｄ７基、ｉｓｏ−ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−ブチル−ｄ９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−トリフルオロメチル基、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、クロロメチル基、トリクロロメチル基、２−クロロエチル基、２，２，２−トリクロロエチル基、４−クロロブチル基、５−クロロペンチル基、６−クロロヘキシル基、ブロモメチル基、２−ブロモエチル基、ヨードメチル基、２−ヨードエチル基、ヒドロキシメチル基、ヒドロキシエチル基、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、アダマンチル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the alkyl group represented by R 1 to R 36 include methyl group, methyl-d1 group, methyl-d3 group, ethyl group, ethyl-d5 group, n-propyl group, n-butyl group, n-pentyl group, n -Hexyl group, n-heptyl group, n-octyl group, n-decyl group, iso-propyl group, iso-propyl-d7 group, iso-butyl group, sec-butyl group, tert-butyl group, tert-butyl- d9 group, iso-pentyl group, neopentyl group, tert-octyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2,2-trifluoromethyl group, perfluoroethyl group 3-fluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, perfluorobutyl group, 5-fluoropentyl group, 6-fluoro Hexyl group, chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, 5-chloropentyl group, 6-chlorohexyl group, bromomethyl group, 2-bromoethyl group , Iodomethyl group, 2-iodoethyl group, hydroxymethyl group, hydroxyethyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylethyl group, 4-fluorocyclohexyl group, norbornyl group And adamantyl group and the like, but are not limited thereto.
Ｒ1乃至Ｒ36で表されるアルコキシ基として、上述したアルキル基を有するアルキルオキシ基、及びアラルキルオキシ基を挙げることができる。具体的には、メトキシ基、エトキシ基、プロポキシ基、２−エチル−オクチルオキシ基、ベンジルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the alkoxy group represented by R 1 to R 36 include the above-described alkyloxy groups having an alkyl group and aralkyloxy groups. Specific examples include a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, and the like, but of course not limited thereto.
Ｒ1乃至Ｒ36で表されるアリール基として、フェニル基、フェニル−ｄ５基、４−メチルフェニル基、４−メトキシフェニル基、４−エチルフェニル基、４−フルオロフェニル基、４−トリフルオロメチルフェニル基、３，５−ジメチルフェニル基、２，６−ジエチルフェニル基、メシチル基、４−ｔｅｒｔ−ブチルフェニル基、ジトリルアミノフェニル基、ビフェニル基、ターフェニル基、ナフチル基、ナフチル−ｄ７基、アセナフチレニル基、アントリル基、アントリル−ｄ９基、フェナントリル基、フェナントリル−ｄ９基、ピレニル基、ピレニル−ｄ９基、アセフェナントリレニル基、アセアントリレニル基、クリセニル基、ジベンゾクリセニル基、ベンゾアントリル基、ベンゾアントリル−ｄ１１基、ジベンゾアントリル基、ナフタセニル基、ピセニル基、ペンタセニル基、フルオレニル基、トリフェニレニル基、ペリレニル基、ペリレニル−ｄ１１基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the aryl group represented by R 1 to R 36, a phenyl group, a phenyl -d5 group, 4-methylphenyl group, a 4-methoxyphenyl group, 4-ethylphenyl group, a 4-fluorophenyl group, 4-trifluoromethyl Phenyl group, 3,5-dimethylphenyl group, 2,6-diethylphenyl group, mesityl group, 4-tert-butylphenyl group, ditolylaminophenyl group, biphenyl group, terphenyl group, naphthyl group, naphthyl-d7 group Acenaphthylenyl group, anthryl group, anthryl-d9 group, phenanthryl group, phenanthryl-d9 group, pyrenyl group, pyrenyl-d9 group, acephenanthrenyl group, aceanthrylenyl group, chrysenyl group, dibenzochrysenyl group, benzo Anthryl, benzoanthryl-d11, dibenzoanthryl, naphth Seniru group, picenyl group, a pentacenyl group, a fluorenyl group, a triphenylenyl group, a perylenyl group, but perylenyl -d11 groups and the like, but the present invention is of course not limited thereto.
Ｒ1乃至Ｒ36で表される複素環基として、ピロリル基、ピリジル基、ピリジル−ｄ５基、ビピリジル基、メチルピリジル基、ピリミジニル基、ピラジニル基、ピリダジニル基、ターピロリル基、チエニル基、チエニル−ｄ４基、ターチエニル基、プロピルチエニル基、ベンゾチエニル基、ジベンゾチエニル基、ジベンゾチエニル−ｄ７基、フリル基、フリル−ｄ４基、ベンゾフリル基、イソベンゾフリル基、ジベンゾフリル基、ジベンゾフリル−ｄ７基、キノリル基、キノリル−ｄ６基、イソキノリル基、キノキサリニル基、ナフチリジニル基、キナゾリニル基、フェナントリジニル基、インドリジニル基、フェナジニル基、カルバゾリル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、アクリジニル基、フェナジニル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the heterocyclic group represented by R 1 to R 36 include pyrrolyl, pyridyl, pyridyl-d5, bipyridyl, methylpyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, terpyrrolyl, thienyl, and thienyl-d4. Group, tertenyl group, propylthienyl group, benzothienyl group, dibenzothienyl group, dibenzothienyl-d7 group, furyl group, furyl-d4 group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, dibenzofuryl-d7 group, quinolyl Group, quinolyl-d6 group, isoquinolyl group, quinoxalinyl group, naphthyridinyl group, quinazolinyl group, phenanthridinyl group, indolizinyl group, phenazinyl group, carbazolyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, acridinyl group, Jiniru group, and the like, but the invention is of course not limited thereto.
Ｒ1乃至Ｒ36で表されるアリールオキシ基として、上述したアリール基又は複素環基を有するアリールオキシ基を挙げることができる。具体的には、フェノキシ基、４−ｔｅｒｔ−ブチルフェノキシ基、チエニルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the aryloxy group represented by R 1 to R 36 include the aryloxy group having the aryl group or heterocyclic group described above. Specific examples include a phenoxy group, a 4-tert-butylphenoxy group, a thienyloxy group, and the like, but are not limited thereto.
Ｒ1乃至Ｒ36で表される置換アミノ基として、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the substituted amino group represented by R 1 to R 36 include a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, a dianisolylamino group, and the like. It is not a thing.
Ｒ1乃至Ｒ36で表されるハロゲン原子として、フッ素、塩素、臭素、ヨウ素等が挙げられるが、もちろんこれらに限定されるものではない。 As the halogen atom represented by R 1 to R 36, fluorine, chlorine, bromine, and iodine and the like, but the present invention is of course not limited thereto.
Ｒ1乃至Ｒ36で表されるシリル基として、トリメチルシリル基、トリエチルシリル基、トリイソプロピルシリル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the silyl group represented by R 1 to R 36 include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and a triisopropylsilyl group.
上記アルキル基、アルコキシ基、アリール基、複素環基及びアリールオキシ基がさらに有してもよい置換基として、メチル基、エチル基、プロピル基等のアルキル基、フェニル基、ビフェニル基等のアリール基、チエニル基、ピロリル基、ピリジル基等の複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基等の置換アミノ基、メトキシ基、エトキシ基等のアルコキシ基、フッ素、塩素、臭素、ヨウ素等のハロゲン原子、水酸基、シアノ基、ニトロ基等が挙げられるが、もちろんこれらに限定されるものではない。 As the substituent that the alkyl group, alkoxy group, aryl group, heterocyclic group and aryloxy group may further have, an alkyl group such as a methyl group, an ethyl group or a propyl group, an aryl group such as a phenyl group or a biphenyl group , Heterocyclic groups such as thienyl group, pyrrolyl group and pyridyl group, substituted amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group and dianisolylamino group, methoxy group and ethoxy group And alkoxy groups such as fluorine, chlorine, bromine, iodine and the like, hydroxyl groups, cyano groups, nitro groups, and the like, but are not limited thereto.
式［１］において、Ｒ1乃至Ｒ36は、それぞれ同じであっても異なっていてもよい。また式［１］において、隣り合う置換基が互いに結合して、例えば、ベンゼン環等の環構造を形成してもよい。 In the formula [1], R 1 to R 36 may be the same or different. In the formula [1], adjacent substituents may be bonded to each other to form a ring structure such as a benzene ring.
式［１］で表される縮合多環化合物の具体例を以下に示す。ただし、これらの化合物はあくまでも具体例であり、本発明はこれらに限定されるものではない。 Specific examples of the condensed polycyclic compound represented by the formula [1] are shown below. However, these compounds are only specific examples, and the present invention is not limited to these.
次に、一般式［２］で示される縮合多環化合物について説明する。 Next, the condensed polycyclic compound represented by the general formula [2] will be described.
式［２］において、Ｒ1乃至Ｒ32は、それぞれ水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアルコキシ基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基、ハロゲン原子、スルフィド基及びシリル基からなる群より選ばれる置換基である。 In the formula [2], R 1 to R 32 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, It is a substituent selected from the group consisting of a substituted amino group, a halogen atom, a sulfide group and a silyl group.
Ｒ1乃至Ｒ32で表されるアルキル基として、メチル基、メチル−ｄ１基、メチル−ｄ３基、エチル基、エチル−ｄ５基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−デシル基、ｉｓｏ−プロピル基、ｉｓｏ−プロピル−ｄ７基、ｉｓｏ−ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−ブチル−ｄ９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−トリフルオロメチル基、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、クロロメチル基、トリクロロメチル基、２−クロロエチル基、２，２，２−トリクロロエチル基、４−クロロブチル基、５−クロロペンチル基、６−クロロヘキシル基、ブロモメチル基、２−ブロモエチル基、ヨードメチル基、２−ヨードエチル基、ヒドロキシメチル基、ヒドロキシエチル基、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、アダマンチル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the alkyl group represented by R 1 to R 32 include methyl group, methyl-d1 group, methyl-d3 group, ethyl group, ethyl-d5 group, n-propyl group, n-butyl group, n-pentyl group, n -Hexyl group, n-heptyl group, n-octyl group, n-decyl group, iso-propyl group, iso-propyl-d7 group, iso-butyl group, sec-butyl group, tert-butyl group, tert-butyl- d9 group, iso-pentyl group, neopentyl group, tert-octyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2,2-trifluoromethyl group, perfluoroethyl group 3-fluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, perfluorobutyl group, 5-fluoropentyl group, 6-fluoro Hexyl group, chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, 5-chloropentyl group, 6-chlorohexyl group, bromomethyl group, 2-bromoethyl group , Iodomethyl group, 2-iodoethyl group, hydroxymethyl group, hydroxyethyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylethyl group, 4-fluorocyclohexyl group, norbornyl group And adamantyl group and the like, but are not limited thereto.
Ｒ1乃至Ｒ32で表されるアルコキシ基として、上述したアルキル基を有するアルキルオキシ基、及びアラルキルオキシ基を挙げることができる。具体的には、メトキシ基、エトキシ基、プロポキシ基、２−エチル−オクチルオキシ基、ベンジルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the alkoxy group represented by R 1 to R 32 include the above-described alkyloxy groups having an alkyl group and aralkyloxy groups. Specific examples include a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, and the like, but of course not limited thereto.
Ｒ1乃至Ｒ32で表されるアリール基として、フェニル基、フェニル−ｄ５基、４−メチルフェニル基、４−メトキシフェニル基、４−エチルフェニル基、４−フルオロフェニル基、４−トリフルオロメチルフェニル基、３，５−ジメチルフェニル基、２，６−ジエチルフェニル基、メシチル基、４−ｔｅｒｔ−ブチルフェニル基、ジトリルアミノフェニル基、ビフェニル基、ターフェニル基、ナフチル基、ナフチル−ｄ７基、アセナフチレニル基、アントリル基、アントリル−ｄ９基、フェナントリル基、フェナントリル−ｄ９基、ピレニル基、ピレニル−ｄ９基、アセフェナントリレニル基、アセアントリレニル基、クリセニル基、ジベンゾクリセニル基、ベンゾアントリル基、ベンゾアントリル−ｄ１１基、ジベンゾアントリル基、ナフタセニル基、ピセニル基、ペンタセニル基、フルオレニル基、トリフェニレニル基、ペリレニル基、ペリレニル−ｄ１１基等が挙げられるが、もちろんこれらに限定されるものではない。 As the aryl group represented by R 1 to R 32 , phenyl group, phenyl-d5 group, 4-methylphenyl group, 4-methoxyphenyl group, 4-ethylphenyl group, 4-fluorophenyl group, 4-trifluoromethyl Phenyl group, 3,5-dimethylphenyl group, 2,6-diethylphenyl group, mesityl group, 4-tert-butylphenyl group, ditolylaminophenyl group, biphenyl group, terphenyl group, naphthyl group, naphthyl-d7 group Acenaphthylenyl group, anthryl group, anthryl-d9 group, phenanthryl group, phenanthryl-d9 group, pyrenyl group, pyrenyl-d9 group, acephenanthrenyl group, aceanthrylenyl group, chrysenyl group, dibenzochrysenyl group, benzo Anthryl, benzoanthryl-d11, dibenzoanthryl, naphth Seniru group, picenyl group, a pentacenyl group, a fluorenyl group, a triphenylenyl group, a perylenyl group, but perylenyl -d11 groups and the like, but the present invention is of course not limited thereto.
Ｒ1乃至Ｒ32で表される複素環基として、ピロリル基、ピリジル基、ピリジル−ｄ５基、ビピリジル基、メチルピリジル基、ピリミジニル基、ピラジニル基、ピリダジニル基、ターピロリル基、チエニル基、チエニル−ｄ４基、ターチエニル基、プロピルチエニル基、ベンゾチエニル基、ジベンゾチエニル基、ジベンゾチエニル−ｄ７基、フリル基、フリル−ｄ４基、ベンゾフリル基、イソベンゾフリル基、ジベンゾフリル基、ジベンゾフリル−ｄ７基、キノリル基、キノリル−ｄ６基、イソキノリル基、キノキサリニル基、ナフチリジニル基、キナゾリニル基、フェナントリジニル基、インドリジニル基、フェナジニル基、カルバゾリル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、アクリジニル基、フェナジニル基等が挙げられるが、もちろんこれらに限定されるものではない。 As the heterocyclic group represented by R 1 to R 32 , pyrrolyl group, pyridyl group, pyridyl-d5 group, bipyridyl group, methylpyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, terpyrrolyl group, thienyl group, thienyl-d4 Group, tertenyl group, propylthienyl group, benzothienyl group, dibenzothienyl group, dibenzothienyl-d7 group, furyl group, furyl-d4 group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, dibenzofuryl-d7 group, quinolyl Group, quinolyl-d6 group, isoquinolyl group, quinoxalinyl group, naphthyridinyl group, quinazolinyl group, phenanthridinyl group, indolizinyl group, phenazinyl group, carbazolyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, acridinyl group, Jiniru group, and the like, but the invention is of course not limited thereto.
Ｒ1乃至Ｒ36で表されるアリールオキシ基として、上述したアリール基又は複素環基を有するアリールオキシ基を挙げることができる。具体的には、フェノキシ基、４−ｔｅｒｔ−ブチルフェノキシ基、チエニルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the aryloxy group represented by R 1 to R 36 include the aryloxy group having the aryl group or heterocyclic group described above. Specific examples include a phenoxy group, a 4-tert-butylphenoxy group, a thienyloxy group, and the like, but are not limited thereto.
Ｒ1乃至Ｒ32で表される置換アミノ基として、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基等が挙げられるが、もちろんこれらに限定されるものではない。 As the substituted amino group represented by R 1 to R 32, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, dianisolylamino an amino group and the like are of course limited to It is not a thing.
Ｒ1乃至Ｒ32で表されるハロゲン原子として、フッ素、塩素、臭素、ヨウ素等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the halogen atom represented by R 1 to R 32 include, but are not limited to, fluorine, chlorine, bromine, iodine and the like.
Ｒ1乃至Ｒ32で表されるシリル基として、トリメチルシリル基、トリエチルシリル基、トリイソプロピルシリル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the silyl group represented by R 1 to R 32 include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and a triisopropylsilyl group.
上記アルキル基、アルコキシ基、アリール基、複素環基及びアリールオキシ基がさらに有してもよい置換基として、メチル基、エチル基、プロピル基等のアルキル基、フェニル基、ビフェニル基等のアリール基、チエニル基、ピロリル基、ピリジル基等の複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基等の置換アミノ基、メトキシ基、エトキシ基等のアルコキシ基、フッ素、塩素、臭素、ヨウ素等のハロゲン原子、水酸基、シアノ基、ニトロ基等が挙げられるが、もちろんこれらに限定されるものではない。 As the substituent that the alkyl group, alkoxy group, aryl group, heterocyclic group and aryloxy group may further have, an alkyl group such as a methyl group, an ethyl group or a propyl group, an aryl group such as a phenyl group or a biphenyl group , Heterocyclic groups such as thienyl group, pyrrolyl group and pyridyl group, substituted amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group and dianisolylamino group, methoxy group and ethoxy group And alkoxy groups such as fluorine, chlorine, bromine, iodine and the like, hydroxyl groups, cyano groups, nitro groups, and the like, but are not limited thereto.
式［２］において、Ｒ1乃至Ｒ32は、それぞれ同じであっても異なっていてもよい。 In the formula [2], R 1 to R 32 may be different even in respectively the same.
式［２］で表される縮合多環化合物の具体例を以下に示す。ただし、これらの化合物はあくまでも具体例であり、本発明はこれらに限定されるものではない。 Specific examples of the condensed polycyclic compound represented by the formula [2] are shown below. However, these compounds are only specific examples, and the present invention is not limited to these.
また本発明の有機発光素子において、好ましくは、発光層４にピレン骨格を有する縮合多環化合物がさらに含まれる。ここでピレン骨格を有する縮合多環化合物として、例えば、下記に示される化合物を挙げることができる。ただし下記に示される化合物はあくまでも具体例であり、本発明はこれらに限定されるものではない。 In the organic light emitting device of the present invention, the light emitting layer 4 preferably further includes a condensed polycyclic compound having a pyrene skeleton. Here, examples of the condensed polycyclic compound having a pyrene skeleton include the following compounds. However, the compounds shown below are only specific examples, and the present invention is not limited thereto.
本発明の有機発光素子において、発光層４は、式［１］及び式［２］の縮合多環化合物のみで構成されていてもよいが、好ましくは、ホストとゲスト（ドーパント）とで構成される。発光層４がホストとゲストとで構成される場合、式［１］及び式［２］の縮合多環化合物は、ホストとして使用してもよいし、ゲストとして使用してもよい。 In the organic light emitting device of the present invention, the light emitting layer 4 may be composed of only the condensed polycyclic compound of the formula [1] and the formula [2], but is preferably composed of a host and a guest (dopant). The When the light emitting layer 4 is comprised with a host and a guest, the condensed polycyclic compound of Formula [1] and Formula [2] may be used as a host, and may be used as a guest.
発光層が、キャリア輸送性のホストとゲストとからなる場合、発光に至る主な過程は、以下のいくつかの過程からなる。
１．発光層内での電子・正孔の輸送。
２．ホストの励起子生成。
３．ホスト分子間の励起エネルギー伝達。
４．ホストからゲストへの励起エネルギー移動。
When the light-emitting layer is composed of a carrier transporting host and guest, the main process leading to light emission includes the following several processes.
1. Transport of electrons and holes in the light emitting layer.
2. Host exciton generation.
3. Excitation energy transfer between host molecules.
4). Excitation energy transfer from host to guest.
それぞれの過程における所望のエネルギー移動や、発光はさまざまな失活過程と競争で起こる。 Desired energy transfer and light emission in each process occur by various deactivation processes and competition.
ここで有機発光素子の発光効率を高めるためには、発光中心材料そのものの発光量子収率が大きい方が好ましい。しかしながら、ホストとホストとの間、又はホストとゲストとの間のエネルギー移動が以下の効率的にできるか、についても大きな問題となる。また、通電による発光劣化は今のところ原因は明らかではないが、少なくとも発光中心材料そのもの、又は当該発光中心材料の周辺に存在する分子に起因する発光中心材料の環境変化に関連したものと想定される。 Here, in order to increase the light emission efficiency of the organic light emitting device, it is preferable that the emission center material itself has a higher emission quantum yield. However, whether or not energy transfer between the host and the host or between the host and the guest can be efficiently performed is also a big problem. In addition, although the cause of luminescence degradation due to energization is not clear at present, it is assumed that it is related to the environmental change of the luminescent center material due to at least the luminescent center material itself or molecules existing around the luminescent center material. The
一方、式［１］及び式［２］の縮合多環化合物は、いずれも分子中にジフェニルベンゾフルオランテン骨格という共通骨格を有しているので、双方の化合物の相溶性は良好である。そこで、式［１］及び式［２］の縮合多環化合物を発光層のホスト又はゲストとして使用すると、式［１］及び式［２］の縮合多環化合物は、それぞれ発光層４となる薄膜内に均一に分散される。これにより発光層内においてゲストとゲストとが会合されにくくなる。 On the other hand, the condensed polycyclic compounds of the formulas [1] and [2] both have a common skeleton called a diphenylbenzofluoranthene skeleton in the molecule, so that both compounds have good compatibility. Therefore, when the condensed polycyclic compound of the formula [1] and the formula [2] is used as a host or guest of the light emitting layer, the condensed polycyclic compound of the formula [1] and the formula [2] is a thin film that becomes the light emitting layer 4 respectively. Uniformly distributed within. This makes it difficult for the guests to associate with each other in the light emitting layer.
また式［１］の縮合多環化合物のＨＯＭＯエネルギーは、式［２］の縮合多環化合物のＨＯＭＯエネルギーと比べて浅い。このため、式［１］の縮合多環化合物を発光層のゲストとして使用すると、式［１］の縮合多環化合物がホール（正孔）をトラップしやすいため、発光領域が陽極側に偏りやすい。従って、素子を連続駆動したときに素子の劣化を引き起こすと考えられる。 Further, the HOMO energy of the condensed polycyclic compound of the formula [1] is shallower than the HOMO energy of the condensed polycyclic compound of the formula [2]. For this reason, when the condensed polycyclic compound of the formula [1] is used as a guest in the light emitting layer, the condensed polycyclic compound of the formula [1] tends to trap holes, so that the light emitting region tends to be biased toward the anode side. . Therefore, it is considered that the element is deteriorated when the element is continuously driven.
そこで上述したホールのトラップを防ぐために、例えば、発光層内において、ホールだけでなく電子をトラップする形態にすることが考えられる。こうすることで発光層内の発光領域を特定の箇所に偏らせることなく広げることができる。 In order to prevent the above-described hole trapping, for example, it is conceivable to form not only holes but also electrons in the light emitting layer. By doing so, the light emitting region in the light emitting layer can be expanded without being biased to a specific location.
ここでホール及び電子をそれぞれ十分にトラップするためには、好ましくは、ホストのＨＯＭＯがゲストのＨＯＭＯよりも０．３ｅＶよりも深く設定し、ホストのＬＵＭＯがゲストのＬＵＭＯよりも０．３ｅＶよりも浅く設定する。一方、式［１］の縮合多環化合物のエネルギーギャップは２．１ｅＶ程度であるため、上述したＨＯＭＯ及びＬＵＭＯの関係を実現するには、ホストは２．７ｅＶ程度のエネルギーギャップを有するのが好ましい。 Here, in order to sufficiently trap holes and electrons, preferably, the host HOMO is set to be deeper than the guest HOMO by 0.3 eV, and the host LUMO is more than 0.3 eV than the guest LUMO. Set shallow. On the other hand, since the energy gap of the condensed polycyclic compound of the formula [1] is about 2.1 eV, the host preferably has an energy gap of about 2.7 eV in order to realize the above-described relationship between HOMO and LUMO. .
このようにホストがエネルギーギャップの広い材料とすることにより、このホストの発光波長が短波長領域に存在することになる。これに対して、式［１］の縮合多環化合物の吸収帯は短波長領域にはほとんど存在しないため、式［１］の縮合多環化合物のみをゲストとして使用すると、ホストとゲストとの間におけるエネルギー移動効率が低下し、色純度が低下する。 Thus, when the host is made of a material having a wide energy gap, the emission wavelength of the host exists in a short wavelength region. On the other hand, since the absorption band of the condensed polycyclic compound of the formula [1] hardly exists in the short wavelength region, when only the condensed polycyclic compound of the formula [1] is used as a guest, In this case, the energy transfer efficiency is lowered and the color purity is lowered.
そこで式［２］の縮合多環化合物を、例えば、補助ドーパント（アシストドーパント）として、式［１］の縮合多環化合物と共に発光層の構成材料として使用する。このとき式［２］の縮合多環化合物は式［１］の縮合多環化合物との相溶性が良好で、かつホストの発光領域に吸収帯を有するので、ホストから式［１］の縮合多環化合物へのエネルギー移動をスムーズかつ効率的に行うことができる。従って、ゲスト本来の発光を取り出すことができると共に素子を長寿命化することもできる。また式［１］の縮合多環化合物をゲストとして使用する場合、式［２］の縮合多環化合物を当該ゲストに対応するホストとして使用しても同様の効果が現われる。 Therefore, the condensed polycyclic compound of the formula [2] is used as a constituent material of the light emitting layer together with the condensed polycyclic compound of the formula [1] as an auxiliary dopant (assist dopant), for example. At this time, the condensed polycyclic compound of the formula [2] has good compatibility with the condensed polycyclic compound of the formula [1] and has an absorption band in the light emitting region of the host. Energy transfer to the ring compound can be performed smoothly and efficiently. Therefore, the light emitted from the guest can be extracted and the life of the device can be extended. Further, when the condensed polycyclic compound of the formula [1] is used as a guest, the same effect appears even if the condensed polycyclic compound of the formula [2] is used as a host corresponding to the guest.
他方、上述したピレン骨格を有する縮合多環化合物は、アモルファス性に優れ、高いガラス転移温度を有するため耐熱性が高い。このため、当該ピレン骨格を有する縮合多環化合物を発光層のホストとして使用すると、安定した良好な薄膜を形成することができるので、ムラのない均一な発光を得ることができる。 On the other hand, the above-mentioned condensed polycyclic compound having a pyrene skeleton is excellent in amorphous properties and has a high glass transition temperature, and thus has high heat resistance. For this reason, when the condensed polycyclic compound having the pyrene skeleton is used as a host of the light emitting layer, a stable and good thin film can be formed, and uniform light emission without unevenness can be obtained.
以上より、発光層４の構成材料として式［１］の縮合多環化合物と式［２］の縮合多環化合物とを組み合わせて使用することにより、長い期間輝度を維持することができると共に、通電劣化を小さくすることができる。また式［１］の縮合多環化合物及び式［２］の縮合多環化合物に加えて、ピレン骨格を有する縮合多環化合物を発光層４の構成材料として使用することにより通電劣化をさらに小さくすることができる。 As described above, the combined use of the condensed polycyclic compound of the formula [1] and the condensed polycyclic compound of the formula [2] as the constituent material of the light emitting layer 4 can maintain the luminance for a long period of time and Deterioration can be reduced. Further, in addition to the condensed polycyclic compound of the formula [1] and the condensed polycyclic compound of the formula [2], the use of a condensed polycyclic compound having a pyrene skeleton as a constituent material of the light emitting layer 4 further reduces the deterioration of energization. be able to.
式［１］の縮合多環化合物、又は式［１］及び式［２］の縮合多環化合物を発光層４のゲストとして使用する場合、ホストに対するゲストの濃度は０．０１重量％乃至５０重量％、好ましくは、１重量％乃至２０重量％である。ゲストはホストからなる層の全体に均一に含まれてもよく、濃度勾配を有して含まれてもよい。またある領域に部分的に含ませることでゲスト材料を含まないホストからなる層の領域があってもよい。 When the condensed polycyclic compound of the formula [1] or the condensed polycyclic compound of the formulas [1] and [2] is used as the guest of the light emitting layer 4, the concentration of the guest with respect to the host is 0.01 wt% to 50 wt%. %, Preferably 1% to 20% by weight. The guest may be uniformly contained in the entire layer composed of the host, or may be contained with a concentration gradient. In addition, a region of a layer made of a host that does not include the guest material may be provided by being partially included in a certain region.
本発明の有機発光素子は、発光層４の構成材料として、式［１］及び式［２］の縮合多環化合物を使用する。また、これらの化合物に加えて、必要に応じてこれまで知られている低分子系及びポリマー系の正孔輸送性材料、発光性材料あるいは電子輸送性材料等を一緒に使用してもよい。 The organic light emitting device of the present invention uses the condensed polycyclic compound of the formula [1] and the formula [2] as a constituent material of the light emitting layer 4. In addition to these compounds, if necessary, low molecular weight and polymer hole transporting materials, light emitting materials, electron transporting materials and the like may be used together.
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、また注入された正孔を発光層に輸送する優れたモビリティを有することが好ましい。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、フェニレンジアミン誘導体、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ピラゾリン誘導体、ピラゾロン誘導体、オキサゾール誘導体、フルオレノン誘導体、ヒドラゾン誘導体、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、及びポリ（ビニルカルバゾール）、ポリ（シリレン）、ポリ（チオフェン）、その他導電性高分子が挙げられるが、これらに限定されるものではない。 The hole injecting and transporting material preferably has excellent mobility for facilitating the injection of holes from the anode and transporting the injected holes to the light emitting layer. Low molecular and high molecular weight materials having hole injection and transport performance include triarylamine derivatives, phenylenediamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, pyrazolone derivatives, oxazole derivatives, fluorenone derivatives, hydrazones. Examples include, but are not limited to, derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinyl carbazole), poly (silylene), poly (thiophene), and other conductive polymers.
電子注入輸送性材料としては、陰極からの電子の注入を容易にし、注入された電子を発光層に輸送する機能を有するものから任意に選ぶことができる。また、正孔輸送材料のキャリア移動度とのバランス等を考慮し選択される。電子注入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、チアゾール誘導体、チアジアゾール誘導体、ピラジン誘導体、トリアゾール誘導体、トリアジン誘導体、ペリレン誘導体、キノリン誘導体、キノキサリン誘導体、フルオレノン誘導体、アントロン誘導体、フェナントロリン誘導体、有機金属錯体等が挙げられるが、これらに限定されるものではない。 The electron injection / transport material can be arbitrarily selected from those having a function of facilitating injection of electrons from the cathode and transporting the injected electrons to the light emitting layer. Further, it is selected in consideration of the balance with the carrier mobility of the hole transport material. Materials having electron injection and transport performance include oxadiazole derivatives, oxazole derivatives, thiazole derivatives, thiadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, fluorenone derivatives, anthrone derivatives, phenanthroline derivatives. , Organometallic complexes and the like, but are not limited thereto.
次に本発明の有機発光素子を構成するその他の部材について説明する。 Next, other members constituting the organic light emitting device of the present invention will be described.
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又はこれらの合金、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、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。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、陽極は一層で構成されていてもよいし、複数の層で構成されていてもよい。 As a constituent material of 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, or alloys thereof, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. The metal oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. 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、仕事関数が小さいものがよい。例えば、リチウム、ナトリウム、カリウム、カルシウム、マグネシウム、アルミニウム、インジウム、ルテニウム、チタニウム、マンガン、イットリウム、銀、鉛、錫、クロム等の金属単体が挙げられる。また、これらの金属を組み合わせて合金にしてもよい。例えば、リチウム−インジウム、ナトリウム−カリウム、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、マグネシウム−インジウム等の合金が使用できる。また、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、陰極は一層で構成されていてもよいし、複数の層で構成されていてもよい。 On the other hand, the material constituting the cathode is preferably a material having a small work function. Examples thereof include simple metals such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, ruthenium, titanium, manganese, yttrium, silver, lead, tin, and chromium. Further, these metals may be combined to form an alloy. For example, alloys such as lithium-indium, sodium-potassium, magnesium-silver, aluminum-lithium, aluminum-magnesium, and magnesium-indium can be used. Also, metal oxides such as indium tin oxide (ITO) can be used. These electrode materials may be used alone or in combination of two or more. Moreover, the cathode may be composed of a single layer or a plurality of layers.
本発明の有機発光素子で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜等を用いて発色光をコントロールすることも可能である。 Although it does not specifically limit as a board | substrate used with the organic light emitting element of this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film or the like on the substrate.
尚、作製した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッ素樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜、さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属等をカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。 Note that a protective layer or a sealing layer can be provided for the manufactured element in order to prevent contact with oxygen, moisture, or the like. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluororesins, polyparaxylene, polyethylene, silicone resins, and polystyrene resins, and photocurable resins. Can be mentioned. Further, it is possible to cover glass, a gas-impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
本発明の素子は、基板上に薄膜トランジスタ（ＴＦＴ）を作製し、それに接続して作製することも可能である。 The element of the present invention can be manufactured by forming a thin film transistor (TFT) on a substrate and connecting it.
また、素子の光取り出し方向に関しては、ボトムエミッション型（基板側から光を取り出す構成）及びトップエミッション型（基板の反対側から光を取り出す構成）のいずれも可能である。 As for the light extraction direction of the element, either a bottom emission type (a configuration in which light is extracted from the substrate side) or a top emission type (a configuration in which light is extracted from the opposite side of the substrate) is possible.
本発明の有機発光素子において、発光層及びその他の有機化合物層は、以下に示す方法により形成される。一般には、真空蒸着法、イオン化蒸着法、スパッタリング、プラズマを用いて作製する。また、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）により薄膜を形成してもよい。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。 In the organic light emitting device of the present invention, the light emitting layer and other organic compound layers are formed by the following method. In general, it is manufactured using a vacuum deposition method, an ionization deposition method, sputtering, or plasma. Further, it may be dissolved in an appropriate solvent to form a thin film by a known coating method (for example, spin coating, dipping, casting method, LB method, ink jet method, etc.). In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
上記結着樹脂としては、広範囲な結着性樹脂より選択できる。例えば、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、ポリアリレート樹脂、ポリスチレン樹脂、ＡＢＳ樹脂、ポリブタジエン樹脂、ポリウレタン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ポリアミド樹脂、ポリイミド樹脂、ポリエチレン樹脂、ポリエーテルスルホン樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、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。また、これらは単独又は共重合体ポリマーとして１種又は２種以上混合してもよい。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。 The binder resin can be selected from a wide range of binder resins. For example, polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, ABS resin, polybutadiene resin, polyurethane resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, polyamide resin, polyimide resin, polyethylene resin, Examples include, but are not limited to, polyethersulfone resins, diallyl phthalate resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins, and the like. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer. Furthermore, you may use together additives, such as a well-known plasticizer, antioxidant, and an ultraviolet absorber, as needed.
以下、実施例により本発明をさらに具体的に説明するが、本発明はこれらに限定されるものではない。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited thereto.
＜ＨＯＭＯエネルギー及びＬＵＭＯエネルギーの評価＞
後述する実施例において、発光層の構成材料として使用される化合物について、ＨＯＭＯエネルギー及びＬＵＭＯエネルギーの評価を行った。
<Evaluation of HOMO energy and LUMO energy>
In Examples described later, HOMO energy and LUMO energy were evaluated for compounds used as constituent materials of the light emitting layer.
まず真空蒸着法により、ガラス基板上に、発光層の構成材料からなる薄膜（膜厚２０ｎｍ）を形成した。次に、この薄膜について、大気下光電子分光装置（測定機器名：ＡＣ−２、理研機器製）を用いてＨＯＭＯエネルギーを測定した。また、この薄膜について、分光光度計（測定機器名：Ｕ−３０１０、日立製作所製）を用いて、紫外−可視光吸収スペクトル測定を行い、当該吸収スペクトルの吸収端からエネルギーギャップを求めた。次に、このようにして得られたＨＯＭＯエネルギーの値とエネルギーギャップの値とを用いてＬＵＭＯエネルギーを算出した。結果を表１に示す。 First, a thin film (thickness 20 nm) made of the constituent material of the light emitting layer was formed on a glass substrate by vacuum deposition. Next, the HOMO energy of this thin film was measured using an atmospheric photoelectron spectrometer (measuring instrument name: AC-2, manufactured by Riken Kikai Co., Ltd.). Moreover, about this thin film, the ultraviolet-visible light absorption spectrum measurement was performed using the spectrophotometer (measurement apparatus name: U-3010, Hitachi Ltd. make), and the energy gap was calculated | required from the absorption edge of the said absorption spectrum. Next, LUMO energy was calculated using the HOMO energy value and the energy gap value thus obtained. The results are shown in Table 1.
＜実施例１＞
図１に示される有機発光素子を以下に示す方法により作製した。
<Example 1>
The organic light emitting device shown in FIG. 1 was produced by the method shown below.
ガラス基板（基板１）上に、スパッタ法により酸化錫インジウム（ＩＴＯ）を成膜して陽極２を形成した。このとき陽極２の膜厚を１２０ｎｍとした。次に、これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いで純水で洗浄後乾燥した。さらに、ＵＶ／オゾン洗浄を施した。以上に示す通りに処理を行った基板を透明導電性支持基板として使用した。 On the glass substrate (substrate 1), indium tin oxide (ITO) was formed by sputtering to form the anode 2. At this time, the film thickness of the anode 2 was 120 nm. Next, this was ultrasonically washed successively with acetone and isopropyl alcohol (IPA), then washed with pure water and dried. Further, UV / ozone cleaning was performed. The substrate processed as described above was used as a transparent conductive support substrate.
次に、下記に示される化合物Ａ１とクロロホルムとを混合して、濃度０．１重量％のクロロホルム溶液を調製した。 Next, Compound A1 shown below and chloroform were mixed to prepare a chloroform solution having a concentration of 0.1% by weight.
次に、このクロロホルム溶液を陽極２上に滴下し、スピンコートを行うことにより薄膜を成膜した。次に、真空オーブン中において、８０℃で１０分間の条件で加熱乾燥し薄膜中の溶剤を完全に除去することによりホール輸送層３を形成した。このときホール輸送層３の膜厚は１０ｎｍであった。 Next, this chloroform solution was dropped on the anode 2 and spin coating was performed to form a thin film. Next, the hole transport layer 3 was formed by heating and drying in a vacuum oven at 80 ° C. for 10 minutes to completely remove the solvent in the thin film. At this time, the film thickness of the hole transport layer 3 was 10 nm.
次に、真空蒸着法により、ホール輸送層３上に、ホストである例示化合物Ｎｏ．２−２と、ゲスト（第一ゲスト）である例示化合物Ｎｏ．１−１とを、重量比にして９８：２となるように共蒸着して発光層４を形成した。このとき発光層４の膜厚を４０ｎｍとし、蒸着時の真空度を１．０×１０-4Ｐａとし、成膜速度を０．１ｎｍ／ｓｅｃ乃至０．２ｎｍ／ｓｅｃとした。 Next, the exemplified compound No. which is a host is formed on the hole transport layer 3 by a vacuum deposition method. 2-2 and Exemplified Compound No. 1 which is a guest (first guest). 1-1 was co-evaporated to a weight ratio of 98: 2 to form the light emitting layer 4. At this time, the thickness of the light emitting layer 4 was 40 nm, the degree of vacuum during vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 0.1 nm / sec to 0.2 nm / sec.
次に、真空蒸着法により、発光層４上に、２，９−ビス［２−（９，９’−ジメチルフルオレニル）］−１，１０−フェナントロリンを成膜して電子輸送層５を形成した。このとき電子輸送層５の膜厚を２０ｎｍとし、蒸着時の真空度を１．０×１０-4Ｐａとし、成膜速度を０．１ｎｍ／ｓｅｃ乃至０．２ｎｍ／ｓｅｃとした。 Next, 2,9-bis [2- (9,9′-dimethylfluorenyl)]-1,10-phenanthroline is formed on the light-emitting layer 4 by vacuum deposition to form the electron transport layer 5. Formed. At this time, the thickness of the electron transport layer 5 was 20 nm, the degree of vacuum during vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 0.1 nm / sec to 0.2 nm / sec.
次に、真空蒸着法により、電子輸送層５上に、フッ化リチウムを成膜しＬｉＦ膜を形成した。このときＬｉＦ膜の膜厚を０．５ｎｍとし、蒸着時の真空度を１．０×１０-4Ｐａとし、成膜速度を０．０１ｎｍ／ｓｅｃとした。次に、真空蒸着法により、ＬｉＦ膜上にアルミニウムを成膜しＡｌ膜を形成した。このときＡｌ膜の膜厚を１００ｎｍとし、蒸着時の真空度を１．０×１０-4Ｐａとし、成膜速度を０．５ｎｍ／ｓｅｃ乃至１．０ｎｍ／ｓｅｃとした。ここで、上記ＬｉＦ膜及びＡｌ膜（アルミニウム−リチウム合金膜）は、電子注入電極（陰極６）として機能する。 Next, a lithium fluoride film was formed on the electron transport layer 5 by a vacuum deposition method to form a LiF film. At this time, the film thickness of the LiF film was set to 0.5 nm, the degree of vacuum during vapor deposition was set to 1.0 × 10 −4 Pa, and the film formation rate was set to 0.01 nm / sec. Next, aluminum was formed on the LiF film by vacuum deposition to form an Al film. At this time, the thickness of the Al film was set to 100 nm, the degree of vacuum at the time of vapor deposition was set to 1.0 × 10 −4 Pa, and the film formation rate was set to 0.5 nm / sec to 1.0 nm / sec. Here, the LiF film and the Al film (aluminum-lithium alloy film) function as an electron injection electrode (cathode 6).
次に、水分の吸着によって素子劣化が起こらないように、乾燥空気雰囲気中で保護用ガラス板をかぶせてアクリル樹脂系接着材で封止した。以上のようにして有機発光素子を得た。 Next, a protective glass plate was placed in a dry air atmosphere and sealed with an acrylic resin adhesive so as not to cause element degradation due to moisture adsorption. An organic light emitting device was obtained as described above.
得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ電極（陰極６）を負極にして、２０ｍＡ／ｃｍ2の電流を印加したところ赤色の発光を観測した。 When an electric current of 20 mA / cm 2 was applied to the obtained device with an ITO electrode (anode 2) as a positive electrode and an Al electrode (cathode 6) as a negative electrode, red light emission was observed.
次に、素子に印加する電流を１００ｍＡ／ｃｍ2に設定し、素子の信頼性を調べた。ここで、信頼性とは、１００ｍＡ／ｃｍ2に設定し、素子を連続駆動させたときの初期輝度に対する１００時間後の輝度の割合を示すものである。結果を表２に示す。 Next, the current applied to the device was set to 100 mA / cm 2 and the reliability of the device was examined. Here, the reliability refers to the ratio of the luminance after 100 hours to the initial luminance when the element is continuously driven at 100 mA / cm 2 . The results are shown in Table 2.
＜実施例２＞
実施例１において、化合物Ａ１の代わりに、下記に示す化合物Ａ２とクロロホルムとを混合して、濃度０．１重量％のクロロホルム溶液を調製した。
<Example 2>
In Example 1, instead of Compound A1, Compound A2 shown below and chloroform were mixed to prepare a chloroform solution having a concentration of 0.1% by weight.
これ以外は、実施例１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１と同様に評価した。結果を表２に示す。 Except for this, an organic light emitting device was fabricated in the same manner as in Example 1. The obtained device was evaluated in the same manner as in Example 1. The results are shown in Table 2.
＜比較例１＞
実施例１において、例示化合物Ｎｏ．２−２の代わりに、ルブレンを発光層のホストとして使用した。これ以外は、実施例１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１と同様に評価した。結果を表２に示す。
<Comparative Example 1>
In Example 1, Exemplified Compound No. Instead of 2-2, rubrene was used as the host of the light emitting layer. Except for this, an organic light emitting device was fabricated in the same manner as in Example 1. The obtained device was evaluated in the same manner as in Example 1. The results are shown in Table 2.
＜実施例３＞
実施例１において、例示化合物Ｎｏ．２−２の代わりに、例示化合物Ｎｏ．３−３を発光層のホストとして使用した。また第二ゲスト（アシストドーパント）として例示化合物Ｎｏ．２−２を使用した。さらに例示化合物Ｎｏ．１−１、Ｎｏ．２−２及びＮｏ．３−３の重量比が、２：１：９７となるように共蒸着をして発光層４を形成した。これ以外は、実施例１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１と同様に評価した。結果を表２に示す。
<Example 3>
In Example 1, Exemplified Compound No. Instead of 2-2, Exemplified Compound No. 3-3 was used as the host of the light emitting layer. As the second guest (assist dopant), Exemplified Compound No. 2-2 was used. Furthermore, Exemplified Compound No. 1-1, no. 2-2 and No. The light emitting layer 4 was formed by co-evaporation so that the weight ratio of 3-3 was 2: 1: 97. Except for this, an organic light emitting device was fabricated in the same manner as in Example 1. The obtained device was evaluated in the same manner as in Example 1. The results are shown in Table 2.
上記表２より、式［１］及び式［２］で示される縮合多環化合物がいずれも含まれている有機発光素子は、連続駆動時の輝度劣化を低減することが示された。また式［１］及び式［２］で示される縮合多環化合物に加えてピレン骨格を有する縮合多環化合物が含まれている有機発光素子は、連続駆動時の輝度劣化をさらに低減することが示された。 From the above Table 2, it was shown that the organic light-emitting device containing both the condensed polycyclic compounds represented by the formula [1] and the formula [2] reduces luminance deterioration during continuous driving. In addition to the condensed polycyclic compound represented by the formula [1] and the formula [2], the organic light-emitting device including the condensed polycyclic compound having a pyrene skeleton can further reduce luminance deterioration during continuous driving. Indicated.
１ 基板
２ 陽極
３ ホール輸送層
４ 発光層
５ 電子輸送層
６ 陰極
１０ 有機発光素子
DESCRIPTION OF SYMBOLS 1 Board | substrate 2 Anode 3 Hole transport layer 4 Light emitting layer 5 Electron transport layer 6
Claims (2)
該陽極と該陰極との間に挟持され少なくとも発光層を有する有機化合物層と、から構成され、
該発光層に下記一般式［１］で示される縮合多環化合物と、下記一般式［２］で示される縮合多環化合物とが含まれることを特徴とする、有機発光素子。
An organic compound layer sandwiched between the anode and the cathode and having at least a light emitting layer,
An organic light-emitting device, wherein the light emitting layer contains a condensed polycyclic compound represented by the following general formula [1] and a condensed polycyclic compound represented by the following general formula [2].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009112499A JP2010263065A (en) | 2009-05-07 | 2009-05-07 | Organic light-emitting element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009112499A JP2010263065A (en) | 2009-05-07 | 2009-05-07 | Organic light-emitting element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2010263065A true JP2010263065A (en) | 2010-11-18 |
Family
ID=43360920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009112499A Withdrawn JP2010263065A (en) | 2009-05-07 | 2009-05-07 | Organic light-emitting element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2010263065A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030702A (en) * | 2010-12-01 | 2011-04-27 | 天津市佰斯康科技有限公司 | Hole-transporting material and synthesis method thereof |
| JP2013106000A (en) * | 2011-11-16 | 2013-05-30 | Udc Ireland Ltd | Organic electroluminescent element, material for organic electroluminescent element, and light emitting device, display device and illumination device each using organic electroluminescent element |
| US9997717B2 (en) | 2014-12-12 | 2018-06-12 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
-
2009
- 2009-05-07 JP JP2009112499A patent/JP2010263065A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030702A (en) * | 2010-12-01 | 2011-04-27 | 天津市佰斯康科技有限公司 | Hole-transporting material and synthesis method thereof |
| JP2013106000A (en) * | 2011-11-16 | 2013-05-30 | Udc Ireland Ltd | Organic electroluminescent element, material for organic electroluminescent element, and light emitting device, display device and illumination device each using organic electroluminescent element |
| US9997717B2 (en) | 2014-12-12 | 2018-06-12 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4677221B2 (en) | Organic light emitting device | |
| JP4455625B2 (en) | Organic light emitting device | |
| KR101124749B1 (en) | Indenochrysene derivative and organic light-emitting device using same | |
| JP3848306B2 (en) | Anthryl derivative-substituted compound and organic light emitting device using the same | |
| JP3848307B2 (en) | Aminoanthryl derivative-substituted compound and organic light-emitting device using the same | |
| JP5089235B2 (en) | Fused heterocyclic compounds and organic light emitting devices | |
| JP5366505B2 (en) | Indenopyrene compound and organic light-emitting device using the same | |
| JP3840235B2 (en) | Organic light emitting device | |
| JP4599142B2 (en) | Organic light emitting device | |
| JP4035482B2 (en) | Substituted anthryl derivative and organic light emitting device using the same | |
| JP4429149B2 (en) | Fluorene compound and organic light emitting device | |
| KR101115156B1 (en) | Benzofluoranthene compound and organic light-emitting device using the compound | |
| JP5159164B2 (en) | Benzo [ghi] fluoranthene derivative and organic light-emitting device using the same | |
| JP2007186449A (en) | Compound substituted with aminobisanthryl-derived group and organic light-emitting element by using the same | |
| WO2007123256A1 (en) | Compound and organic light emitting device | |
| JP2007230951A (en) | Silyl compound, luminescent material and organic electroluminescent element using the same | |
| JP2006176493A (en) | Aminoanthryl derivative-substituted pyrene compound and organic light-emitting device | |
| JP2006219392A (en) | Bisanthryl derived group-substituted compound and organic light emitting device | |
| JP4871613B2 (en) | Organic light emitting device | |
| JP5031294B2 (en) | Amine compounds and organic light emitting devices | |
| US8173275B2 (en) | Azaindenochrysene derivative and organic light-emitting device | |
| JP2007169182A (en) | Fluorenylene compound and organic light-emitting element using it | |
| JP2010263065A (en) | Organic light-emitting element | |
| JP5110922B2 (en) | Asymmetric fluorene compound and organic light emitting device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20120807 |