JP5653179B2 - フェナンスレン化合物及びこれを用いた有機発光素子 - Google Patents
フェナンスレン化合物及びこれを用いた有機発光素子 Download PDFInfo
- Publication number
- JP5653179B2 JP5653179B2 JP2010248352A JP2010248352A JP5653179B2 JP 5653179 B2 JP5653179 B2 JP 5653179B2 JP 2010248352 A JP2010248352 A JP 2010248352A JP 2010248352 A JP2010248352 A JP 2010248352A JP 5653179 B2 JP5653179 B2 JP 5653179B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- organic light
- light emitting
- phenanthrene
- group
- 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.)
- Active
Links
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 title claims description 67
- -1 Phenanthrene compound Chemical class 0.000 title claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 30
- 150000002894 organic compounds Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 119
- 239000010410 layer Substances 0.000 description 99
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 36
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000005647 linker group Chemical group 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- OSOLELDZBFOFHO-UHFFFAOYSA-N 2-phenylphenanthrene Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3C=CC2=C1 OSOLELDZBFOFHO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 235000002597 Solanum melongena Nutrition 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- HJNAELFLZXCHQK-UHFFFAOYSA-N 2-chlorophenanthrene Chemical compound C1=CC=C2C3=CC=C(Cl)C=C3C=CC2=C1 HJNAELFLZXCHQK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 3
- XDPLWYUXKVCBFV-UHFFFAOYSA-N 1-bromo-3-(3-chlorophenyl)benzene Chemical group ClC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 XDPLWYUXKVCBFV-UHFFFAOYSA-N 0.000 description 3
- LZPXPKCKNYQPGF-UHFFFAOYSA-N 4-[3-(3-chlorophenyl)phenyl]dibenzothiophene Chemical compound ClC1=CC=CC(C=2C=C(C=CC=2)C=2C3=C(C4=CC=CC=C4S3)C=CC=2)=C1 LZPXPKCKNYQPGF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RTIRXIMCVNYZRZ-UHFFFAOYSA-N 2-chloro-7-methylphenanthrene Chemical compound ClC1=CC=C2C3=CC=C(C)C=C3C=CC2=C1 RTIRXIMCVNYZRZ-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000002987 phenanthrenes Chemical class 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 238000001296 phosphorescence spectrum Methods 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004544 sputter deposition Methods 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
- 239000000126 substance Substances 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- ZDSDLOXRDHDBLG-UHFFFAOYSA-N 1,1'-biphenyl;phenanthrene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3C=CC2=C1 ZDSDLOXRDHDBLG-UHFFFAOYSA-N 0.000 description 1
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RKLROMDZXDQSDF-UHFFFAOYSA-N 1-phenylphenanthrene Chemical compound C1=CC=CC=C1C1=CC=CC2=C1C=CC1=CC=CC=C21 RKLROMDZXDQSDF-UHFFFAOYSA-N 0.000 description 1
- DLLLHLGSCWQNBU-UHFFFAOYSA-N 2,7-diphenylphenanthrene Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=C(C=4C=CC=CC=4)C=C3C=CC2=C1 DLLLHLGSCWQNBU-UHFFFAOYSA-N 0.000 description 1
- YJOPFYAGQUNPCZ-UHFFFAOYSA-N 2-(4-chloro-2-formylphenyl)-5-methylbenzaldehyde Chemical group O=CC1=CC(C)=CC=C1C1=CC=C(Cl)C=C1C=O YJOPFYAGQUNPCZ-UHFFFAOYSA-N 0.000 description 1
- VTUSCUYDAUMZIN-UHFFFAOYSA-N 5-chloro-2-(2-formylphenyl)benzaldehyde Chemical group O=CC1=CC(Cl)=CC=C1C1=CC=CC=C1C=O VTUSCUYDAUMZIN-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 150000000918 Europium Chemical class 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes 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
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001572 beryllium Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 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
- 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 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
- 238000012905 input function Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 238000004949 mass spectrometry 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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) Polymers 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
- 125000003367 polycyclic group Chemical group 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
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 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
- 230000002463 transducing effect Effects 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- 238000000870 ultraviolet spectroscopy 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
- 238000007740 vapor deposition Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Description
工程(a):3−ブロモ−3’−クロロビフェニルと、アリール基(Ar−)の基礎となるボロン酸誘導体とのPd触媒によるカップリング反応を行う工程
工程(b):工程(a)で得られた化合物と、フェナンスレンユニットの基礎となるビスピナコールボロン酸エステル誘導体とのPd触媒によるカップリング反応を行う工程
尚、上記合成スキームにおいて、本発明の要旨の範囲内でAr及びRをそれぞれ適宜選択することができ、所望のフェナンスレン化合物を合成することができる。
(i)(基板/)陽極/発光層/陰極
(ii)(基板/)陽極/ホール輸送層/電子輸送層/陰極
(iii)(基板/)陽極/ホール輸送層/発光層/電子輸送層/陰極
(iv)(基板/)陽極/ホール注入層/ホール輸送層/発光層/電子輸送層/陰極
(v)(基板/)陽極/ホール輸送層/発光層/ホール・エキシトンブロッキング層/電子輸送層/陰極
4−クロロ−2,2’−ジホルミルビフェニル:5.33g(21.8mmol)
酢酸:250mL
mBP−Bpin2(ボロン酸エステル):1.50g(3.69mmol)
2−クロロフェナンスレン:1.65g(7.76mmol)
酢酸パラジウム:83mg(0.37mmol)
XPhos(2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルビフェニル):528mg(1.11mmol)
リン酸カリウム:2.35g(11.1mmol)
トルエン:80mL
水:2mL
実測値:m/z=506.34、計算値:C40H26=506.20
[1H−NMR(400MHz、CDCl3)]
δ 8.79(d,2H),8.73(d,2H),8.19(d,2H),8.08(s,2H),8.01(dd,2H),7.92(d,2H),7.90−7.60(m,14H).
例示化合物A04のトルエン希薄溶液を調製した後、この希薄溶液について、アルゴン雰囲気下、77K、励起波長350nmの条件下で燐光スペクトルの測定を行った。得られた燐光スペクトルの第一発光ピークのピーク波長からT1エネルギーを求めた。その結果、T1エネルギーは波長換算値で466nmであった。
ガラス基板上に、加熱蒸着により、例示化合物A04を成膜して測定用の薄膜を形成した。このとき測定用の薄膜の膜厚を20nmとした。次に、紫外可視分光光度計(日本分光株式会社製V−560)を用いて、上記測定用の薄膜について吸光スペクトルを測定した。得られた吸光スペクトルの吸収端よりエネルギーギャップを求めた。その結果、吸光スペクトルの吸収端は347nmであり、例示化合物A04のエネルギーギャップは3.57eVであった。
上記のエネルギーギャップの測定に用いた測定用の薄膜を用いて、光電子分光装置AC−3(理研計器株式会社製)によりイオン化ポテンシャルを測定した。測定の結果、例示化合物A04のイオン化ポテンシャルは6.43eVであった。
LUMO準位は、イオン化ポテンシャル値とエネルギーギャップ値の差から見積ることができる。ここで例示化合物A04では、LUMO準位は−2.86eVであった。
2−クロロフェナンスレン:3.00g(14.1mmol)
ビス(ピナコラト)ジボロン:4.30g(16.9mmol)
ビス(ジベンジリデンアセトン)パラジウム(0):406mg(0.71mmol)
トリシクロヘキシルホスフィン:593mg(2.12mmol)
酢酸カリウム:2.77g(28.2mmol)
1,4−ジオキサン:100mL
3−ブロモ−3’−クロロビフェニル:3.00g(11.2mmol)
4−ジベンゾチオフェンボロン酸:2.63g(11.6mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):352mg(0.31mmol)
トルエン:60mL
エタノール:30mL
10重量%炭酸ナトリウム水溶液:30mL
PT−Bpin:583mg(1.92mmol)
4−(3’−クロロビフェニル−3−イル)ジベンゾチオフェン:646mg(1.74mmol)
酢酸パラジウム:24mg(0.11mmol)
SPhos(2―ジシクロヘキシルホスフィノ―2’,6’−ジメトキシビフェニル):130mg(0.32mmol)
リン酸カリウム:1.11g(5.23mmol)
トルエン:25mL
水:0.6mL
実測値:m/z=512.30、計算値:C38H24S=512.16
[1H−NMR(400MHz、CDCl3)]
δ 8.77(d,1H),8.72(d,1H),8.30−8.15(m,3H),8.09(d,2H),7.98(dd,1H),7.91(d,1H),7.88−7.55(m,13H),7.48(m,2H).
MePT−Bpin:440mg(1.38mmol)
4−(3’−クロロビフェニル−3−イル)ジベンゾチオフェン:394mg(1.06mmol)
酢酸パラジウム:14mg(0.062mmol)
SPhos(2―ジシクロヘキシルホスフィノ―2’,6’−ジメトキシビフェニル):78mg(0.19mmol)
リン酸カリウム:675mg(3.18mmol)
トルエン:18mL
水:0.4mL
実測値:m/z=526.37、計算値:C39H26S=526.18
下記に示す比較化合物H01乃至H05について、実施例1と同様の方法でT1エネルギー及びLUMO準位の評価を行った。結果を表3に示す。実施例1乃至3の結果と合わせて、結果を表3に示す。
基板上に、陽極/ホール輸送層/発光層/ホールブロッキング層/電子輸送層/陰極がこの順に設けられている有機発光素子を、以下に示す方法で作製した。尚、本実施例で使用した化合物の一部を下記に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて例示化合物A09を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて例示化合物B08を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H02を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H03を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H05を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
Claims (11)
- 前記R1乃至R21がいずれも水素原子であることを特徴とする、請求項1に記載のフェナンスレン化合物。
- 陽極と陰極と、
前記陽極と前記陰極との間に挟持される有機化合物層と、から構成される有機発光素子において、
前記有機化合物層に請求項1又は2に記載のフェナンスレン化合物が含まれることを特徴とする、有機発光素子。 - 前記フェナンスレン化合物が発光層に含まれることを特徴とする、請求項3に記載の有機発光素子。
- 前記発光層がホストとゲストとからなり、前記ホストが前記フェナンスレン化合物であることを特徴とする、請求項4に記載の有機発光素子。
- 前記ゲストが燐光発光材料であることを特徴とする、請求項5に記載の有機発光素子。
- 前記燐光発光材料がイリジウム錯体であることを特徴とする、請求項6に記載の有機発光素子。
- 請求項3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するスイッチング素子とを有することを特徴とする、表示装置。
- 画像を表示するための表示部と、画像情報を入力するための入力部と、を有し、
前記表示部が複数の画素を有し、
前記複数の画素が、請求項3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するスイッチング素子と、を有することを特徴とする、画像入力装置。 - 請求項3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、照明装置。
- 露光光源を有する電子写真方式の画像形成装置であって、
前記露光光源が、請求項3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、画像形成装置。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010248352A JP5653179B2 (ja) | 2010-11-05 | 2010-11-05 | フェナンスレン化合物及びこれを用いた有機発光素子 |
KR1020137013613A KR101523153B1 (ko) | 2010-11-05 | 2011-10-25 | 페난트렌 화합물 및 이를 사용한 유기 발광 디바이스 |
EP11837957.7A EP2635545A1 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
CN2011800521037A CN103347841A (zh) | 2010-11-05 | 2011-10-25 | 菲化合物和使用该菲化合物的有机发光器件 |
PCT/JP2011/075016 WO2012060307A1 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
US13/880,250 US8729541B2 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010248352A JP5653179B2 (ja) | 2010-11-05 | 2010-11-05 | フェナンスレン化合物及びこれを用いた有機発光素子 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2012097056A JP2012097056A (ja) | 2012-05-24 |
JP2012097056A5 JP2012097056A5 (ja) | 2013-12-12 |
JP5653179B2 true JP5653179B2 (ja) | 2015-01-14 |
Family
ID=46024420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010248352A Active JP5653179B2 (ja) | 2010-11-05 | 2010-11-05 | フェナンスレン化合物及びこれを用いた有機発光素子 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8729541B2 (ja) |
EP (1) | EP2635545A1 (ja) |
JP (1) | JP5653179B2 (ja) |
KR (1) | KR101523153B1 (ja) |
CN (1) | CN103347841A (ja) |
WO (1) | WO2012060307A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5818870B2 (ja) * | 2012-12-27 | 2015-11-18 | キヤノン株式会社 | 有機発光素子及び表示装置 |
JP6095391B2 (ja) * | 2013-02-06 | 2017-03-15 | キヤノン株式会社 | 有機発光素子 |
KR101733151B1 (ko) * | 2014-08-21 | 2017-05-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69625134T2 (de) * | 1995-08-03 | 2003-10-02 | Kyocera Mita Corp., Osaka | Phenanthrylendiaminderivate und elektrophotoempfindliche Materialien, die diese verwenden |
KR101634423B1 (ko) * | 2005-05-31 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광 발광 다이오드에서의 트리페닐렌 호스트 |
US8154195B2 (en) * | 2007-07-07 | 2012-04-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8330350B2 (en) * | 2007-07-07 | 2012-12-11 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
JP2009051764A (ja) * | 2007-08-27 | 2009-03-12 | Hodogaya Chem Co Ltd | 置換されたフェナントレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
DE102008008953B4 (de) * | 2008-02-13 | 2019-05-09 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP2009215333A (ja) * | 2008-03-07 | 2009-09-24 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子 |
JP2009221442A (ja) * | 2008-03-19 | 2009-10-01 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子 |
WO2010002850A1 (en) * | 2008-06-30 | 2010-01-07 | Universal Display Corporation | Hole transport materials containing triphenylene |
-
2010
- 2010-11-05 JP JP2010248352A patent/JP5653179B2/ja active Active
-
2011
- 2011-10-25 US US13/880,250 patent/US8729541B2/en active Active
- 2011-10-25 WO PCT/JP2011/075016 patent/WO2012060307A1/en active Application Filing
- 2011-10-25 EP EP11837957.7A patent/EP2635545A1/en not_active Withdrawn
- 2011-10-25 KR KR1020137013613A patent/KR101523153B1/ko not_active IP Right Cessation
- 2011-10-25 CN CN2011800521037A patent/CN103347841A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
CN103347841A (zh) | 2013-10-09 |
JP2012097056A (ja) | 2012-05-24 |
EP2635545A1 (en) | 2013-09-11 |
WO2012060307A1 (en) | 2012-05-10 |
US8729541B2 (en) | 2014-05-20 |
US20130207096A1 (en) | 2013-08-15 |
KR20140058395A (ko) | 2014-05-14 |
KR101523153B1 (ko) | 2015-05-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5618753B2 (ja) | 有機発光素子 | |
JP5677036B2 (ja) | 有機発光素子 | |
JP5669550B2 (ja) | インドロフェノキサジン化合物及びこれを用いた有機発光素子 | |
JP5751985B2 (ja) | 縮合多環化合物およびそれを有する有機発光素子 | |
KR101463705B1 (ko) | 크산톤 화합물, 이를 포함하는 유기 발광 디바이스, 디스플레이 장치, 화상 입력 장치 및 조명 장치 | |
JP5729957B2 (ja) | ジベンゾチオフェン化合物およびそれを有する有機発光素子 | |
JP5901167B2 (ja) | スピロ[シクロペンタ[def]トリフェニレン−4,9’−フルオレン]化合物及びそれを有する有機発光素子 | |
JP2012072099A (ja) | インドロ[3,2,1−jk]カルバゾール化合物及びこれを有する有機発光素子 | |
JP6071390B2 (ja) | 新規有機化合物、それを有する有機発光素子及び表示装置 | |
JP5773638B2 (ja) | 縮合多環化合物及びこれを用いた有機発光素子 | |
JP2012020947A (ja) | 新規スピロ(アントラセン−9,9’−フルオレン)−10−オン化合物及びこれを有する有機発光素子 | |
WO2014057873A1 (ja) | ホスフィンオキサイド誘導体およびそれを有する発光素子 | |
KR101490575B1 (ko) | 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자 | |
JP5574860B2 (ja) | ジベンゾスベロン骨格を有する有機発光素子用材料 | |
JP5653179B2 (ja) | フェナンスレン化合物及びこれを用いた有機発光素子 | |
JP5751984B2 (ja) | 縮合多環化合物及びこれを有する有機発光素子 | |
JP5586981B2 (ja) | 新規有機化合物および有機発光素子 | |
JP5645465B2 (ja) | 新規有機化合物 | |
JP5495665B2 (ja) | 有機化合物及びこれを用いた有機発光素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131028 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131028 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141021 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141118 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 5653179 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |