CN102869636A - 新型有机化合物和包括该新型有机化合物的有机发光器件 - Google Patents
新型有机化合物和包括该新型有机化合物的有机发光器件 Download PDFInfo
- Publication number
- CN102869636A CN102869636A CN2011800216797A CN201180021679A CN102869636A CN 102869636 A CN102869636 A CN 102869636A CN 2011800216797 A CN2011800216797 A CN 2011800216797A CN 201180021679 A CN201180021679 A CN 201180021679A CN 102869636 A CN102869636 A CN 102869636A
- Authority
- CN
- China
- Prior art keywords
- organic compound
- organic
- layer
- compound
- luminescent device
- 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.)
- Granted
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005001 aminoaryl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- MJKHEVZCENOWRU-UHFFFAOYSA-N nonacyclo[19.11.1.15,9.02,20.04,18.010,15.025,33.026,31.016,34]tetratriaconta-1(32),2(20),3,5,7,9(34),10,12,14,16,18,21,23,25(33),26,28,30-heptadecaene Chemical group C12=C([C]3C=C45)C=C6C=CC=C[C]6C1=CC=CC2=C3C=C5C=C1C2=C4C=CC=C2C2=CC=CC=C12 MJKHEVZCENOWRU-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 76
- 150000001875 compounds Chemical class 0.000 description 55
- 239000000463 material Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- -1 isobutyl- Chemical group 0.000 description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000010408 film Substances 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- HAXBIWFMXWRORI-UHFFFAOYSA-N Benzo[k]fluoranthene Chemical compound C1=CC(C2=CC3=CC=CC=C3C=C22)=C3C2=CC=CC3=C1 HAXBIWFMXWRORI-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000027756 respiratory electron transport chain Effects 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- FTOVXSOBNPWTSH-UHFFFAOYSA-N benzo[b]fluoranthene Chemical group C12=CC=CC=C1C1=CC3=CC=CC=C3C3=C1C2=CC=C3 FTOVXSOBNPWTSH-UHFFFAOYSA-N 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 238000000103 photoluminescence spectrum Methods 0.000 description 6
- 238000006862 quantum yield reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 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
- 239000004411 aluminium Substances 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
- 150000001399 aluminium compounds Chemical class 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920001940 conductive polymer Chemical class 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- VHGJAFIHUSTRGB-UHFFFAOYSA-N fluoranthen-3-amine Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3N VHGJAFIHUSTRGB-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000123 polythiophene Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003252 quinoxalines Chemical class 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
- 239000004065 semiconductor Substances 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
- 230000003335 steric effect Effects 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 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
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 238000003775 Density Functional Theory Methods 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- JKHBTMCYKLMKDN-UHFFFAOYSA-N O=C(c(c1c23)cccc1c(cccc1)c1c2-c1ccccc1)C3=O Chemical compound O=C(c(c1c23)cccc1c(cccc1)c1c2-c1ccccc1)C3=O JKHBTMCYKLMKDN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Chemical class 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical compound [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005859 coupling reaction Methods 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
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas 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
- 230000005283 ground state Effects 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 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 1
- 238000000059 patterning Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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 compound 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate 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
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- 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
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
-
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
-
- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
-
- 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
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- 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
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
-
- 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
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明提供适合用于蓝色发光器件的新型有机化合物和包括该新型有机化合物的有机发光器件。该有机化合物是醋菲并[4,5-k]苯并[e]醋菲衍生物。
Description
技术领域
本发明涉及新型有机化合物和包括该新型有机化合物的有机发光器件。
背景技术
有机发光器件包括电极对和设置在该对电极之间的有机化合物层。通过从该对电极注入电子和空穴,产生有机化合物层中含有的有机化合物的激子并且当该激子返回基态时发光。
有机发光器件也称为有机电致发光(EL)器件。
近年来,有机发光器件已显著地发展,能够提供能够实现低电压下的高亮度、较宽范围的发射波长、快速响应以及厚度和重量减小的发光器件。目前为止已发明了新型的发光有机化合物。
PTL 1公开了以下所示的IK-12作为构成发光层的有机化合物的实例,发光层为有机化合物层。该化合物具有苯并[k]荧蒽。
作为基本骨架以下示出苯并[k]荧蒽。这是其环具有共轭结构的稠环化合物。
引用列表
专利文献
PTL 1:日本专利公开No.9-241629(无对应的外国公开)
发明内容
PTL 1中公开的IK-12具有苯并[k]荧蒽并且还具有取代基。结果,能够实现蓝色发光。但是,如果引入取代基例如叔丁基,可削弱该化合物的稳定性。因此,本发明提供通过新发明基本骨架而自身实现蓝色发光并且自身具有高稳定性的新型有机化合物。
本发明提供由下述通式(1)或(3)表示的有机化合物。
通式(1)中,R1-R18各自独立地选自氢原子、卤素原子、烷基、烃氧基、氨基基团、芳基和杂环基团。
通式(3)中,R21-R38各自独立地选自氢原子、卤素原子、烷基、烃氧基、氨基基团、芳基和杂环基团。
根据本发明,能够提供以基本骨架单独来实现蓝色发光并且具有高稳定性的有机化合物。还能够提供包括该有机化合物的有机发光器件。
附图说明
图1是表示有机发光器件和与该有机发光器件连接的开关器件的截面示意图。
具体实施方式
本发明提供由下述通式(1)表示的有机化合物。
通式(1)中,R1-R18各自独立地选自氢原子、卤素原子、烷基、烃氧基、氨基基团、芳基和杂环基团。
通式(1)中烷基的实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、辛基、1-金刚烷基和2-金刚烷基。
通式(1)中烃氧基的实例包括甲氧基、乙氧基、丙氧基、2-乙基-辛氧基、苯氧基、4-叔-丁基苯氧基、苄氧基和噻吩氧基。
通式(1)中氨基基团的实例包括N-甲基氨基、N-乙基氨基、N,N-二甲基氨基、N,N-二乙基氨基、N-甲基-N-乙基氨基、N-苄基氨基、N-甲基-N-苄基氨基、N,N-二苄基氨基、苯胺基、N,N-二苯基氨基、N,N-二萘基氨基、N,N-二芴基氨基、N-苯基-N-甲苯基氨基、N,N-二(甲苯基)氨基、N-甲基-N-苯基氨基、N,N-二(茴香醚基)氨基、N- 基-N-苯基氨基、N,N-二 基氨基、N-苯基-N-(4-叔-丁基苯基)氨基和N- 苯基-N-(4-三氟甲基苯基)氨基。
通式(1)中芳基的实例包括苯基、萘基、茚基、联苯基、三联苯基和芴基。
上述取代基,即烷基、烃氧基、氨基基团、芳基和杂环基团,它们是通式(1)中的R1-R18,可具有取代基。取代基的实例包括烷基例如甲基、乙基和丙基;芳烷基例如苄基;芳基例如苯基和联苯基;杂环基团例如吡啶基和吡咯基;氨基基团例如二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基和二(甲苯基)氨基;烃氧基例如甲氧基、乙氧基、丙氧基和苯氧基;氰基;和卤素原子例如氟、氯、溴和碘。
本发明的发明人已关注基本骨架自身。具体地,本发明人试图提供只具有基本骨架的分子具有所需的发射波长区域内的峰值发射波长的化合物。
已知为了实现所需的峰值发射波长,将取代基引入基本骨架中。但是,这种情况下,可能削弱化合物的稳定性。
将有机发光器件用于显示装置时,峰值发射波长需要在430-480nm内以实现蓝色发光。
根据本发明的有机化合物是具有430-480nm的峰值发射波长的化合物。即,这样的化合物能够是蓝色有机发光器件的发光材料。
为了增加有机发光器件的发光效率,发光材料自身的量子产率需要高。
为了实现这点,要求下述条件。
1.振子强度高。
2.有助于发光的骨架具有小的振动区域。
关于条件1,重要的是改善有助于发光的发光材料的骨架的对称性。这是因为具有高对称性的分子中每个原子的转变偶极矩(transition dipole moment)容易在相同方向上取向,因此使转变偶极矩增加。高转变偶极矩导致高振子强度,这导致高量子产率。
而且,由于通过在某方向上使共轭扩展而使分子的转变偶极矩增加,因此使振子强度增加。
根据本发明的有机化合物具有通过将共轭从苯并[k]荧蒽的8-位扩展到11-位而形成的稠环结构。这样的结构具有比苯并[k]荧蒽高的转变偶极矩。
即,根据本发明的有机化合物的结构具有高振子强度。
关于条件2,基本骨架不具有旋转结构时,有机化合物已获得的能量转换为动能例如旋转或者振动能受到抑制,因此能够使作为光子发出的能量的比例增加。换言之,能够抑制量子产率的减少。
根据本发明的有机化合物的基本骨架,即醋菲基[4,5-k]苯并[e]醋菲骨架自身具有蓝色区域中的峰值发射波长。而且,该基本骨架不具有旋转结构,因此能够抑制由旋转振动引起的量子产率的减少。
基本骨架的比较例是苯并[b]荧蒽。将苯并[b]荧蒽与作为本发明的实例的醋菲基[4,5-k]苯并[e]-7,10-二苯基醋菲(例示化合物A110)进行比较时,前者的峰值发射波长为395nm,而后者的峰值发射波长为439nm。
根据本发明的有机化合物具有蓝色区域中的峰值发射波长,而比较化合物不具有蓝色区域中的峰值发射波长。比较化合物的量子产率为0.49,而根据本发明的有机化合物的量子产率为0.80。根据本发明的化合物以比比较化合物高的效率发光。
已使用作为根据本发明的有机化合物的实例的例示化合物A110进行了比较。根据本发明的有机化合物的基本骨架自身具有蓝色区域中的峰值发射波长和高量子产率。这是因为在例示化合物A110的7-和10-位提供的苯基对峰值发射波长的效果很小,而且对量子产率的效果也很小。
本发明的基本骨架
醋菲基[4,5-k]苯并[e]-7,10-二苯基醋菲(化合物A110)
因此,根据本发明的有机化合物中,基本骨架自身实现蓝色发光和高量子产率。
由于根据本发明的有机化合物在其基本骨架中具有两个五元环结构,因此HOMO/LUMO能级低。因此,根据本发明的有机化合物具有高氧化电位。
这意味着需要较大量的能量以将根据本发明的有机化合物氧化。即,根据本发明的有机化合物对于氧化稳定。
根据本发明的有机化合物的基本骨架具有高平面性并且容易通过分子间堆叠而产生受激准分子(excimer)。因此,可引入位阻基团,即体积大的取代基以防止分子间堆叠。
计算出产生高位阻效应的取代基的位置。具体地,使用密度函数理论在B3LYP/6-31G*能级通过量子化学计算进行计算。
本文中,获得基本骨架与取代基(该计算中苯基)之间的键的二面角以确定位阻效应。随着二面角接近90°,这使抑制分子间堆叠的效果增加,位阻效应增加。
表1示出计算结果。表1也示出由量子化学计算得到的吸收值(S1)。
[表1]
9-和18-位具有大二面角。即,高度抑制由分子间堆叠引起的受激准分子的产生的取代位置为9-和18-位。
在这些位置的苯基具有88°以上的二面角,基本上与基本骨架垂直。这表示这些取代位置最适合抑制受激准分子的产生。这些取代位置是由于基本上垂直配置而使共轭不易扩展并且发射波长不易向较长波长迁移的位置。
由上述结果,通过在9-和18-位引入取代基,分子间堆叠得到抑制,因此作为不容易产生受激准分子的发光材料,得到根据本发明的有机化合物。
本文中,上述“垂直”意味着在9-或18-位引入的取代基的平面与基本骨架的平面垂直。在9-或18-位引入的取代基的实例,除了苯基以外,还包括萘基、茚基、联苯基、三联苯基、芴基和叔丁基。
例如,通过引入取代基,能够将根据本发明的有机化合物的峰值发射波长调节到所需的波长。能够在适合向较长波长迁移的取代位置引入取代基,该位置选自1-至8-位和10-至17-位,即,根据本发明的有机化合物的9-和18-位以外的位置。这是因为9-和18-位对波长变化的影响很小。
将采用基本骨架与苯基之间的不同键合位置时得到的吸收值(S1)彼此进行比较。由吸收值,能够预测取代基的峰值发射波长的变化。
表1示出结果。将在其基本骨架的9-或18-位具有苯基的化合物与非取代化合物进行比较时,前者和后者之间的吸收值之差为3nm以下。另一方面,在不同的取代位置具有苯基的化合物与非取代化合物 之差为6nm-12nm。
换言之,在9-或18-位具有苯基的化合物对波长的影响很小。为了使波长向较长波长迁移,能够在选自1-至8-位和10-至17-位的位置引入取代基。
根据本发明的有机化合物中,通过在选自1-至8-位和10-至17-位的位置引入取代基,使波长向较长波长迁移并且能够获得适合绿色至红色发光的发光材料。
以下示出根据本发明的有机化合物的具体实例。但是,本发明并不限于此。
化合物A1-A146是在基本骨架上具有芳基的有机化合物并且分子只由烃组成。
通过在9-或18-位引入芳基,能够抑制浓度猝灭。这是因为由于9-或18-位的芳基在二面角方面基本上与基本骨架垂直,因此结构变为三维并且能够抑制分子间堆叠。
与基本骨架的峰值发射波长相比,在9-和18-位以外的取代位具有芳基的化合物的峰值发射波长向较长波长迁移。
通过在该位引入芳基,使基本骨架的共轭扩展,这使分子的带隙变窄。因此,这样的化合物能够发出具有比作为非取代化合物的基本骨架自身的发射波长长的波长的光。
组A中的全部有机化合物由烃组成。因此,将基本骨架的氧化电位和还原电位之和的一半设为中心位置时,在保持中心位置的同时能够改变这些有机化合物的氧化-还原的电位宽。
化合物B1-B37是烷基直接与基本骨架键合的有机化合物。
烷基直接与基本骨架键合时,根据本发明的有机化合物受到具有给电子性的烷基的影响,因此使氧化电位增加。即,组B中的例示化合物容易被氧化。
化合物C1-C33是其分子中包括杂原子的有机化合物。
根据本发明的有机化合物具有包括杂原子的取代基时,该有机化合物经历源自该杂原子的氧化-还原电位的变化。这能够使峰值发射波长向较长波长迁移。
根据本发明的有机化合物能够用作电子捕集发光材料。而且,该有机化合物具有包括杂原子的取代基时,由于氧化-还原电位变化,因此除了电子捕集发光材料以外,该有机化合物能够用于用途例如电子传输层材料、空穴传输层材料和空穴捕集发光材料。
根据本发明的有机化合物更有利地由下述通式(2)表示。这是因为通过在本发明的基本骨架的9-和18-位引入苯基,能够高度抑制受激准分子的产生。苯基在R19或R20位具有取代基时,能够进一步抑制受激准分子的产生。
而且,在R5、R6、R14、R15或R16位引入取代基时,能够显著地改变发射波长。
通式(2)中,由R5、R6、R19和R20表示的取代基各自为烷基。由R14-R16表示的取代基各自为烷基或芳基。
烷基为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基。
芳基为苯基、萘基、芴基、荧蒽基或苯并荧蒽基。芳基可具有上述的烷基作为取代基。
根据本发明的有机化合物能够用作发光层的客体材料。根据本发明的有机化合物可以是发光层的主体材料或辅助材料。
根据本实施方案的有机化合物可用于发光层以外的每个层,即空穴注入层、空穴传输层、空穴阻挡层、激子阻挡层、电子传输层和电子注入层的任一层。
本文中,主体材料是以最高重量比构成发光层的化合物。客体材料是以比主体材料低的重量比构成发光层的化合物,客体材料是有机发光器件中的主要发光化合物。辅助材料是以比主体材料低的重量比构成发光层的化合物,辅助材料为辅助客体材料的发光的化合物。
根据本发明的有机化合物用作客体材料时,客体材料相对于主体材料的浓度优选为0.01wt%-20wt%,更优选为0.5wt%-10wt%。
通过在该两个范围中的一个内改变客体材料的浓度,能够使由发光层发出的光的发射波长向较长波长迁移5nm-20nm。
根据本发明的有机化合物能够通过下述的合成路线1合成。作为 例示化合物所示的化合物也能够通过用其他取代基,例如烷基和苯基取代氢原子来合成。
为了将取代基引入由D1所示的结构,能够使用下述的合成路线。
该合成方法中,在最终合成步骤中制备由下述通式(3)所示的异构体。由于这些异构体具有基本上相同的发光特性,因此异构体可通过重结晶彼此分离或者可以以混合的形式利用。以混合的形式利用它们时,结晶度降低,因此能够预期抑制浓度猝灭的效果。即,能够以高浓度利用它们。
由通式(1)所示的化合物具有异构体。该异构体是由通式(3)表示的化合物。应指出的是,将例示化合物A1的异构体表示为“A1-2”。
通式(3)中,R21-R38各自独立地选自氢原子、卤素原子、烷基、烃氧基、氨基基团、芳基和杂环基团。
通过使用起始材料D1-D4,能够合成根据本发明的各种有机化合物。表2-5示出起始材料D1-D4和使用该起始材料合成的根据本发明的各种有机化合物。省略异构体。
[表2]
[表3]
[表4]
[表5]
现在对包括根据本实施方案的有机化合物的有机发光器件的实例进行说明。
根据本实施方案的有机发光器件具有如下结构,其中在作为电极对的实例的正极和负极之间形成发光层。此外,在正极和发光层之间可形成空穴传输层或空穴注入层。在发光层和负极之间可形成电子传输层、电子注入层、空穴阻挡层、激子阻挡层等。
根据本实施方案的有机发光器件的有机化合物层的层结构并不限于此。
根据本实施方案的有机发光器件中,可形成多个有机化合物层。多个层的实例包括空穴注入层、空穴传输层、发光层、空穴阻挡层、激子阻挡层、电子传输层和电子注入层。这些层能够适当地彼此组合。
根据本实施方案的有机发光器件中,除了根据本发明的有机化合物以外,能够任选地一起使用公知的低分子量或高分子量空穴传输化合物、发光化合物或电子传输化合物。
以下例示这样的化合物。
空穴注入/传输材料能够具有高空穴迁移率以致能够容易地将空穴从正极注入并且能够将注入的空穴传输到发光层。具有空穴注入/传输性的低分子量或高分子量材料的实例包括,但并不限于,三芳基胺衍生物、苯二胺衍生物、1,2-二苯乙烯衍生物、酞菁衍生物、卟啉衍生物、聚乙烯基咔唑、聚噻吩和其他导电聚合物。
除了表6和7中所示的化合物以及表6和7中所示的化合物的衍生物以外,主体材料的实例主要包括,但并不限于,稠环化合物(例如芴衍生物、萘衍生物、蒽衍生物、芘衍生物、咔唑衍生物、喹喔啉衍生物和喹啉衍生物)、有机铝络合物例如三(8-羟基喹啉合)铝、有机锌络合物、三苯基胺衍生物和聚合物衍生物例如聚芴衍生物和聚亚苯基衍生物。
[表6]
[表7]
电子注入/传输材料能够适当地选自容易将电子从负极注入并且能够将注入的电子传输到发光层的材料。考虑例如与空穴注入/传输材料的空穴迁移率的平衡来选择该材料。电子注入/传输材料的实例包括,但并不限于, 二唑衍生物、 唑衍生物、吡嗪衍生物、三唑衍生物、三嗪衍生物、喹啉衍生物、喹喔啉衍生物、菲咯啉衍生物和有机铝络合物。
用于正极的材料应具有尽可能高的功函数。该材料的实例包括金属单质例如金、铂、银、铜、镍、钯、钴、硒、钒和钨;它们的合金;和金属氧化物例如氧化锡、氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌。也能够使用导电聚合物例如聚苯胺、聚吡咯和聚噻吩。这些电极物质可单独使用或者以两种以上物质的组合使用。正极可具有单层结构或多层结构。
用于负极的材料应具有尽可能低的功函数。该材料的实例包括金属单质例如碱金属,例如锂;碱土金属,例如钙;铝;钛;锰;银;铅;和铬。也能够使用将这些金属单质彼此组合的合金。合金的实例包括镁-银、铝-锂和铝-镁。也能够使用金属氧化物例如氧化铟锡(ITO)。这些电极物质可单独使用或者以两种以上物质的组合使用。负极可具有单层结构或多层结构。
为了防止制备的有机发光器件接触氧、水分等,能够在该器件上形成保护层或密封层。
根据本实施方案的有机发光器件中,含有根据本实施方案的有机化合物的层和由其他有机化合物组成的层通过下述方法形成。通常,通过真空沉积法、电离气相沉积法、溅射法、等离子体沉积法或公知的包括将化合物溶解于适当的溶剂的涂布法来形成薄膜。通过真空沉积法、溶液涂布法等形成这样的膜时,不易发生结晶,因此得到的膜具有高的经时稳定性。将涂布法用于形成这样的膜时,能够将适合的粘结剂树脂与该化合物组合使用。
粘结剂树脂的实例包括,但并不限于,聚乙烯基咔唑树脂、聚碳酸酯树脂、聚酯树脂、ABS树脂、丙烯酸系树脂、聚酰亚胺树脂、酚醛树脂、环氧树脂、有机硅树脂和脲醛树脂。此外,可任选地将公知的添加剂例如增塑剂、抗氧化剂和紫外线吸收剂添加到这些粘结剂树脂中。
现在对包括根据本实施方案的有机发光器件的装置进行说明。
根据本实施方案的有机发光器件能够用于显示装置和照明装置。此外,根据本实施方案的有机发光器件能够用于电子照相图像形成装置的曝光光源和液晶显示装置的背光。
显示装置包括显示单元,该显示单元包括根据本实施方案的有机发光器件。该显示单元包括多个像素。每个像素包括根据本实施方案的有机发光器件和作为开关器件的实例的薄膜晶体管(TFT)器件。将该有机发光器件的正极或负极与TFT器件的漏电极或源电极连接。该显示装置能够用作个人电脑(PC)等的图像显示装置。该显示装置可 以是还包括图像输入单元的图像输入装置。
该图像输入装置包括:图像输入单元,用该图像输入单元将来自面阵CCD传感器、线阵CCD传感器、存储卡等的信息输入;和用于显示该输入的信息的显示单元。如果这样的图像输入装置还包括成像光学系统,则得到摄像装置例如数码相机。这样的摄像装置或喷墨打印机可具有:显示单元,其具有基于从外部输入的图像信息来显示图像的图像输出功能;和操作面板,其具有将处理信息输入该图像的输入功能。该显示装置可用于多功能打印机的显示单元。
现在对包括根据本实施方案的有机发光器件的显示装置进行说明。
图1为包括根据本实施方案的有机发光器件和TFT器件的显示装置的截面示意图,TFT器件为用于切换有机发光器件的发光/不发光或者控制发光亮度的开关器件的实例。图1示出两对有机发光器件和TFT器件。尽管图中未示出,但该显示装置可进一步包括用于控制发光亮度的晶体管。通过根据信息驱动该开关器件来开或关该有机发光器件,该显示装置进行显示,并且传输该信息。以下对该显示装置的详细结果进行说明。
图1中所示的显示装置包括由例如玻璃组成的基板1和用于保护TFT器件或有机化合物层的防湿膜2,将该防湿膜2设置在该基板1上。附图标记3表示金属栅电极,附图标记4表示栅绝缘膜,和附图标记5表示半导体层。
TFT器件8包括半导体层5、漏电极6和源电极7。将绝缘膜9设置在TFT器件8的上部。通过接触孔10将有机发光器件的正极11与源电极7连接。该显示装置的结构并不限于此。该有机发光器件的正极或负极只需与TFT器件的源电极或漏电极连接。
图1中,将多个有机化合物层表示为单一有机化合物层12。在负极13上设置用于抑制有机发光器件的劣化的第一保护层14和第二保护层15。
根据本实施方案的显示装置中,对开关器件并无特别限制。可使 用单晶硅基板、金属-绝缘体-金属(MIM)器件、无定形硅(a-Si)器件等。
实施例
实施例1
[A110和A110-2的合成]
将例示化合物A110的异构体表示为“A110-2”。
首先,在0℃下将10.5g(48mmol)的荧蒽-3-胺(E1)添加到300ml的二甲基甲酰胺中。接下来,将8.2g(48mmol)的N-溴琥珀酰亚胺添加到该混合物中。使温度返回到室温,并且将该混合物搅拌8小时。在水中将得到的沉淀物过滤,然后用乙醇进行重结晶。将晶体过滤,用庚烷洗涤,然后干燥。于是,得到了29g棕色固体E2(收率:60%)。随后,将10g(34mmol)的E2放入500ml茄型烧瓶中,并且用氩气将体系内的空气置换。接下来,在氩气氛中将150ml的甲氧基环戊烷放入烧瓶中,并且将该溶液冷却到-75℃。随后,将64ml的1.6M正丁基锂溶液滴加到其中。滴加后,使温度返回室温,并且进行搅拌1小时。接下来,再次将该混合物冷却到-75℃,并且将15g的精细粉碎的干冰添加到该混合物中。使温度逐渐返回到室温后,进行搅拌8小时,然后将1M盐酸添加到该混合物中以使反应终止。随后,用醋酸乙酯进行萃取并且将有机层浓缩以得到棕色液体。通过柱色谱(醋酸乙酯/庚烷=1:3)对该液体进行纯化并且用氯仿/甲醇进行重结晶。于是,得到了2.5g的作为绿黄色晶体的E3(收率:28%)。
接下来,将35g(150mmol)的E4和31.8g(150mmol)的E5放入500ml的乙醇/甲苯溶液(10/1)中,并且在搅拌该混合物的同时将52ml的6N氢氧化钾溶液滴加到其中。滴加后,将该混合物加热到50℃,搅拌1小时,然后冷却。将得到的沉淀物过滤并且依次用水、乙醇和异丙醇进行洗涤。通过在减压下进行加热来进行干燥以得到48.2g的黑色固体E6(收率:78%)。
接下来,将3.6g(8.95mmol)的E6和2.6g(9.74mmol)的E3放入100ml甲苯中,并且将该混合物加热到80℃。随后,然后缓慢地将1.2ml(10.4mmol)的亚硝酸异戊酯滴加到该混合物中。然后在110℃下将该混合物搅拌3小时。将该混合物冷却,然后用100ml水洗涤两次。将得到的有机层用饱和盐水溶液洗涤并且用硫酸镁干燥。随后,将得到的溶液过滤,并且将滤液浓缩以得到棕色液体。通过柱色谱(甲苯/庚烷=3:1)对该液体进行纯化并且用甲苯/乙醇进行重结晶。于是, 得到了3.17g作为异构体的混合物的黄色晶体固体(收率:62%)。
通过NMR波谱确认该化合物的结构。
1H NMR(CDCl3,400MHz)σ(ppm):8.57(dd,2H,J=8.24,4.12Hz),8.37(dd,2H,J=8.24,2.29Hz),8.21(d,2H,J=10.99Hz),7.87-7.28(m,54H),6.76(S,1H),6.58(d,1H,J=7.33Hz),6.51(s,1H),6.36(d,1H,J=7.33Hz)
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A110和A110-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在439nm具有最大强度。
实施例2
[化合物A8和A8-2的合成]
将有机化合物E7和E8添加到甲苯、乙醇和碳酸钠水溶液的混合溶剂中,并且使用四(三苯基膦)钯作为催化剂进行偶合反应(混合溶液的温度:78℃,反应时间:10小时)。反应后,用水洗涤有机层并且干燥。使用甲苯/庚烷溶剂进行柱分离,然后在甲苯溶剂中进行重结晶以得到晶体固体E9。
接下来,除了将实施例1中使用的有机化合物E4变为E9以外, 通过与实施例1的那些相同的反应和纯化来合成化合物E10。
除了将实施例1中使用的有机化合物E6变为E10以外,通过与实施例1的那些相同的反应和纯化而得到作为异构体的混合物的黄色晶体固体。通过重结晶将部分黄色晶体固体分离为化合物A8和A8-2。
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A8和A8-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在451nm具有最大强度。
实施例3
[A24和A24-2的合成]
除了将实施例2中的E7和E8分别变为E11和E12以外,进行与实施例2的那些相同的反应和纯化。
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A24和A24-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在445nm具有最大强度。
实施例4
[A54和A54-2的合成]
除了将实施例2中的E7和E5分别变为E11和E13以外,进行与实施例2的那些相同的反应和纯化。
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A54和A54-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在453nm具有最大强度。
实施例5
[A73和A73-2的合成]
除了将实施例2中的E4变为E14以外,进行与实施例2的那些相同的反应和纯化。
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A73和A73-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在455nm具有最大强度。
实施例6
[A93和A93-2的合成]
除了将实施例2中的E8和E5分别变为E12和E16以外,进行与实施例2的那些相同的反应和纯化。
在350nm的激发波长下用可由Hitachi Ltd.得到的F-4500测定含有例示化合物A93和A93-2的1×10-5mol/L甲苯溶液的光致发光光谱。两个光谱都在443nm具有最大强度。
实施例7-33
实施例7-33中,采用多层有机发光器件(正极/空穴注入层/空穴传输层/发光层/空穴·激子-阻挡层/电子传输层/负极)。在玻璃基板上将具有100nm的厚度的ITO膜图案化。在其上具有ITO膜的基板上,在10-5Pa的压力的真空室内通过电阻加热真空沉积法依次形成下述的有机层和电极层以致彼此相对的电极的面积为3mm2。
空穴传输层(30nm)G-1
发光层(30nm)主体:G-2,客体:例示化合物(5重量%)
空穴·激子-阻挡层(10nm)G-3
电子传输层(30nm)G-4
金属电极层1(1nm)LiF
金属电极层2(100nm)Al
用由Hewlett-Packard Development Company制造的pA计4140B测定每个有机发光器件的电流-电压特性,并且用由Topcon Corporation制造的BM7测定其发光亮度。
表8示出实施例7-33的发光效率和电压。表8中的客体材料是表1中的合成化合物。
[表8]
实施例34-39
实施例34-39中,制备具有正极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/负极的结构的有机发光器件。
通过溅射法在用作支撑体的玻璃基板上形成用作反射正极的铝合金(AlNd)以具有100nm的厚度。而且,通过溅射法形成用作透明正极的ITO膜以具有80nm的厚度。接下来,在正极的周边部中形成由丙烯酸系树脂组成并且具有1.5μm的厚度的器件分隔膜,并且在其中形成了具有3mm的半径的开口。依次使用丙酮和异丙醇(IPA)用超声波对基板进行洗涤。然后在沸腾下用IPA对基板进行洗涤并干燥。而且,对基板的表面进行UV/臭氧清洁。
在10-5Pa的压力的真空室内通过电阻加热真空沉积法依次形成下述的有机层。随后,通过溅射法沉积IZO以形成用作负极并且具有30nm的厚度的透明电极。形成后,在氮气氛中进行密封。
空穴注入层(95nm)G-11
空穴传输层(10nm)G-12
发光层(35nm)主体:G-13,客体:例示化合物(2重量%)
电子传输层(10nm)G-14
电子注入层(70nm)G15(80重量%)和Li(20重量%)
用由Hewlett-Packard Development Company制造的pA计4140B测定每个有机发光器件的电流-电压特性,并且用由Topcon Corporation制造的BM7测定其发光亮度。
表9示出实施例34-39的发光效率和电压。
[表9]
(结果和讨论)
根据本发明的有机化合物是显示高量子产率并且适合蓝色发光的新型化合物。将该有机化合物用于有机发光器件时,能够使发光器件具有令人满意的发光特性。
尽管已参照例示实施方案对本发明进行了说明,但应理解本发明并不限于所公开的例示实施方案。下述权利要求的范围应给予最宽泛的解释以包括所有这样的变形以及等同的结构和功能。
本申请要求于2010年4月30日提交的日本专利申请No.2010-105625的权益,在此通过引用将其全文并入本文。
附图标记列表
8TFT器件
11正极
12有机化合物层
13负极
Claims (10)
2.根据权利要求1的有机化合物,其中R1-R8和R10-R17中的至少一个选自烷基和芳基,其他的R1-R8和R10-R17为氢原子。
4.有机发光器件,包括:
电极对;和
设置在该对电极之间的有机化合物层,
其中该有机化合物层含有根据权利要求1的有机化合物。
5.有机发光器件,包括:
电极对;和
设置在该对电极之间的有机化合物层,
其中该有机化合物层含有根据权利要求3的有机化合物。
6.根据权利要求4的有机发光器件,其中该有机化合物层为发光层。
7.显示装置,包括:多个像素,每个像素包括根据权利要求4的有机发光器件和与该有机发光器件连接的开关器件。
8.图像输入装置,包括:
输入图像的图像输入单元;和
用于显示该图像的显示单元,
其中该显示单元包括多个像素,每个像素包括根据权利要求4的有机发光器件和与该有机发光器件连接的开关器件。
9.显示装置,包括:多个像素,每个像素包括根据权利要求5的有机发光器件和与该有机发光器件连接的开关器件。
10.图像输入装置,包括:
输入图像的图像输入单元;和
用于显示该图像的显示单元,
其中该显示单元包括多个像素,每个像素包括根据权利要求5的有机发光器件和与该有机发光器件连接的开关器件。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010105625A JP5700952B2 (ja) | 2010-04-30 | 2010-04-30 | 新規有機化合物およびそれを有する有機発光素子 |
JP2010-105625 | 2010-04-30 | ||
PCT/JP2011/060007 WO2011136155A1 (en) | 2010-04-30 | 2011-04-19 | Novel organic compound and organic light-emitting device including the same |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102869636A true CN102869636A (zh) | 2013-01-09 |
CN102869636B CN102869636B (zh) | 2015-05-13 |
Family
ID=44861455
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180021679.7A Expired - Fee Related CN102869636B (zh) | 2010-04-30 | 2011-04-19 | 有机化合物和包括该有机化合物的有机发光器件 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9005778B2 (zh) |
EP (1) | EP2569268B1 (zh) |
JP (1) | JP5700952B2 (zh) |
KR (1) | KR101490575B1 (zh) |
CN (1) | CN102869636B (zh) |
WO (1) | WO2011136155A1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5713699B2 (ja) | 2011-01-20 | 2015-05-07 | キヤノン株式会社 | 有機化合物、有機発光素子及び画像表示装置 |
JP6132580B2 (ja) * | 2013-02-15 | 2017-05-24 | キヤノン株式会社 | 新規縮合多環化合物およびそれを有する有機発光素子 |
JPWO2016204150A1 (ja) * | 2015-06-16 | 2018-04-05 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
CN108701771B (zh) * | 2016-02-24 | 2021-09-10 | 出光兴产株式会社 | 有机电致发光元件和电子设备 |
KR20190059296A (ko) | 2016-10-03 | 2019-05-30 | 이데미쓰 고산 가부시키가이샤 | 화합물, 조성물, 유기 일렉트로루미네센스 소자 및 전자기기 |
JP6829583B2 (ja) * | 2016-11-09 | 2021-02-10 | 出光興産株式会社 | 化合物、組成物、有機エレクトロルミネッセンス素子、及び電子機器 |
JP7114596B2 (ja) * | 2016-12-22 | 2022-08-08 | メルク パテント ゲーエムベーハー | 少なくとも2種の有機機能性化合物を含む混合物 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030027016A1 (en) * | 2000-04-21 | 2003-02-06 | Tdk Corporation | Organic EL device |
JP2003238516A (ja) * | 2002-02-19 | 2003-08-27 | Petroleum Energy Center | 新規な縮合芳香族化合物及びそれを利用した有機エレクトロルミネッセンス素子 |
CN101541713A (zh) * | 2007-04-02 | 2009-09-23 | 佳能株式会社 | 新型稠环芳族化合物和具有该化合物的有机发光器件 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3693128B2 (ja) | 1996-03-08 | 2005-09-07 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
JP4255610B2 (ja) * | 1999-12-28 | 2009-04-15 | 出光興産株式会社 | 白色系有機エレクトロルミネッセンス素子 |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
JP5252960B2 (ja) * | 2007-04-02 | 2013-07-31 | キヤノン株式会社 | 縮合環芳香族化合物及びこれを用いた有機発光素子 |
JP5414190B2 (ja) * | 2007-04-02 | 2014-02-12 | キヤノン株式会社 | 有機発光素子 |
JP5561929B2 (ja) | 2008-12-19 | 2014-07-30 | キヤノン株式会社 | 新規有機化合物 |
JP5618555B2 (ja) * | 2009-04-23 | 2014-11-05 | キヤノン株式会社 | 新規有機化合物および発光素子および画像表示装置 |
-
2010
- 2010-04-30 JP JP2010105625A patent/JP5700952B2/ja not_active Expired - Fee Related
-
2011
- 2011-04-19 EP EP11774936.6A patent/EP2569268B1/en not_active Not-in-force
- 2011-04-19 KR KR1020127030556A patent/KR101490575B1/ko not_active IP Right Cessation
- 2011-04-19 WO PCT/JP2011/060007 patent/WO2011136155A1/en active Application Filing
- 2011-04-19 CN CN201180021679.7A patent/CN102869636B/zh not_active Expired - Fee Related
- 2011-04-19 US US13/643,972 patent/US9005778B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030027016A1 (en) * | 2000-04-21 | 2003-02-06 | Tdk Corporation | Organic EL device |
JP2003238516A (ja) * | 2002-02-19 | 2003-08-27 | Petroleum Energy Center | 新規な縮合芳香族化合物及びそれを利用した有機エレクトロルミネッセンス素子 |
CN101541713A (zh) * | 2007-04-02 | 2009-09-23 | 佳能株式会社 | 新型稠环芳族化合物和具有该化合物的有机发光器件 |
Also Published As
Publication number | Publication date |
---|---|
WO2011136155A1 (en) | 2011-11-03 |
EP2569268A4 (en) | 2013-12-04 |
KR101490575B1 (ko) | 2015-02-05 |
US9005778B2 (en) | 2015-04-14 |
US20130038515A1 (en) | 2013-02-14 |
KR20130024917A (ko) | 2013-03-08 |
EP2569268A1 (en) | 2013-03-20 |
EP2569268B1 (en) | 2014-11-05 |
CN102869636B (zh) | 2015-05-13 |
JP5700952B2 (ja) | 2015-04-15 |
JP2011231086A (ja) | 2011-11-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101870705B (zh) | 有机化合物、发光器件和图像显示装置 | |
CN102405200B (zh) | 有机化合物、发光器件和图像显示装置 | |
CN102869636B (zh) | 有机化合物和包括该有机化合物的有机发光器件 | |
WO2013042584A1 (en) | Novel organic compound, organic light-emitting device, and display apparatus | |
JP5773638B2 (ja) | 縮合多環化合物及びこれを用いた有機発光素子 | |
KR101802618B1 (ko) | 신규 유기 화합물 및 그를 갖는 유기 발광 소자 및 표시 장치 | |
CN102459136B (zh) | 新型有机化合物和有机发光器件 | |
CN102245545B (zh) | 有机化合物 | |
CN102933529B (zh) | 有机化合物和包括该有机化合物的有机发光器件 | |
WO2011158767A1 (en) | Novel organic compound and organic light-emitting device having the same | |
JP4750893B1 (ja) | 新規有機化合物および有機発光素子 | |
CN109689618A (zh) | 基于胺的化合物和包含其的有机发光器件 | |
CN112239475B (zh) | 含氮化合物、电子元件和电子装置 | |
CN102131753B (zh) | 有机化合物和使用该有机化合物的有机发光器件 | |
JP5586981B2 (ja) | 新規有機化合物および有機発光素子 | |
KR101417239B1 (ko) | 신규 축합 다환 화합물 및 유기 발광 소자 | |
WO2012017977A1 (en) | Novel organic compound and organic light-emitting device including same | |
JP2012148987A (ja) | 有機化合物、有機発光素子及び表示装置 | |
KR20210040255A (ko) | 유기 화합물, 유기발광소자, 표시장치, 촬상 장치, 조명 장치 및 이동체 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150513 Termination date: 20170419 |