CN102933529B - 有机化合物和包括该有机化合物的有机发光器件 - Google Patents
有机化合物和包括该有机化合物的有机发光器件 Download PDFInfo
- Publication number
- CN102933529B CN102933529B CN201180027516.XA CN201180027516A CN102933529B CN 102933529 B CN102933529 B CN 102933529B CN 201180027516 A CN201180027516 A CN 201180027516A CN 102933529 B CN102933529 B CN 102933529B
- Authority
- CN
- China
- Prior art keywords
- organic compound
- organic
- luminescent device
- layer
- compound
- 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
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 98
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 125000003277 amino group Chemical group 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 75
- 150000001875 compounds Chemical class 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000000463 material Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 28
- -1 heterocyclic radical Chemical class 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 14
- 230000005540 biological transmission Effects 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 230000027756 respiratory electron transport chain Effects 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000103 photoluminescence spectrum Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 101100268333 Solanum lycopersicum TFT8 gene Proteins 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001399 aluminium compounds Chemical class 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 238000000869 ion-assisted deposition Methods 0.000 description 2
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 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
- 229920000642 polymer Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 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
- 239000002356 single layer Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 0 Cc(cc(-c(c1c2c(-c3c4*)ccc1-1)ccc2-c3c(*)c2c4c(*)c(cc(*)c(*)c3)c3c2*)c-1c1)c1N Chemical compound Cc(cc(-c(c1c2c(-c3c4*)ccc1-1)ccc2-c3c(*)c2c4c(*)c(cc(*)c(*)c3)c3c2*)c-1c1)c1N 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 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
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-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
- 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
- 239000004676 acrylonitrile butadiene styrene Substances 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
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910002064 alloy oxide Inorganic materials 0.000 description 1
- VVTQWTOTJWCYQT-UHFFFAOYSA-N alumane;neodymium Chemical compound [AlH3].[Nd] VVTQWTOTJWCYQT-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000010406 cathode material Substances 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
- 239000012141 concentrate Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 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
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007789 sealing Methods 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
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 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
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/285—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
-
- 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
- C07D213/16—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 containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09G—ARRANGEMENTS OR CIRCUITS FOR CONTROL OF INDICATING DEVICES USING STATIC MEANS TO PRESENT VARIABLE INFORMATION
- G09G3/00—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes
- G09G3/20—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters
- G09G3/22—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources
- G09G3/30—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels
- G09G3/32—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels semiconductive, e.g. using light-emitting diodes [LED]
- G09G3/3208—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels semiconductive, e.g. using light-emitting diodes [LED] organic, e.g. using organic light-emitting diodes [OLED]
-
- 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
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- 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
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- 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
-
- 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
- C09K2211/1011—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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Theoretical Computer Science (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
Abstract
本发明提供适合发绿光的由通式(1)表示的新型有机化合物和包括该有机化合物的有机发光器件。式(1)中,R1-R16各自独立地选自氢原子、卤素原子、取代或未取代的烷基、取代或未取代的烃氧基、取代的氨基基团、取代或未取代的芳基和取代或未取代的杂环基。
Description
技术领域
本发明涉及新型有机化合物和包括这样的有机化合物的有机发光器件。
背景技术
有机发光器件包括阳极、阴极和设置在它们之间的有机化合物层。这两个电极将电子和空穴注入有机化合物层时,其中含有的有机化合物产生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。
目前为止已深入地进行了新型发光有机化合物的开发。这样的化合物的开发对于提供高性能有机发光器件是重要的。
作为这样的有机化合物的实例,PTL1公开了例示化合物1-A:
作为这样的有机化合物的另一实例,PTL2公开了例示化合物1:
(例示化合物1)
引用列表
专利文献
PTL 1:日本专利公开No.2008-235734(无外国对应申请)
PTL 2:日本专利公开No.2008-300753(无外国对应申请)
发明内容
PTL 1和2中公开的有机化合物自身几乎不发光。上述式中所示的例示化合物1-A和1由未取代的稠环组成。换言之,这些有机化合物具有由上述结构式表示的基本骨架。
因此,本发明提供新型有机化合物,其只以其基本骨架就能发光并且能够在绿色区域中发光。
根据本发明的方面,提供由通式(1)表示的有机化合物:
式(1)中,R1-R16各自独立地选自氢原子、卤素原子、取代或未取代的烷基、取代或未取代的烃氧基、取代的氨基基团、取代或未取代的芳基、和取代或未取代的杂环基。
根据上述本发明的方面,能够提供新型有机化合物,只以其基本骨架其就具有宽带隙和深LUMO能级。因此,只以其骨架,该有机化合物就发绿色区域中的光。此外,将取代基引入骨架提供能够发红光而不是绿光的新型有机化合物。此外,能够提供包括这样的新型有机化合物的有机发光器件。
附图说明
图1为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
根据本发明的实施方案的有机化合物由通式(1)表示:
式(1)中,R1-R16各自独立地选自氢原子、卤素原子、取代或未取代的烷基、取代或未取代的烃氧基、取代的氨基基团、取代或未取代的芳基和取代或未取代的杂环基。
芳基和杂环基能够用烷基取代。
氨基基团能够用烷基或芳基取代。
式(1)中,烷基能够是例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、辛基、1-金刚烷基或2-金刚烷基。
式(1)中,烃氧基能够是例如甲氧基、乙氧基、丙氧基、2-乙基辛氧基、苯氧基、4-叔-丁基苯氧基、苄氧基或噻吩氧基。
式(1)中,氨基基团能够是例如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-甲基-N-苯基氨基、N,N-二莱基氨基、N-苯基-N-(4-叔-丁基苯基)氨基或N-苯基-N-(4-三氟甲基苯基)氨基。
式(1)中,芳基能够为例如苯基、萘基、茚基、联苯基、三联苯基或芴基。
式(1)中,杂环基能够为例如吡啶基、唑基、二唑基、噻唑基、噻二唑基、咔唑基、吖啶基或菲咯啉基。
本发明人已将注意力集中于只由基本骨架组成的分子,其具有落在所需的发射波长区域内的峰值发射波长。根据本实施方案的基本骨架由下述结构式表示:
尽管已知化合物的基本骨架能够被取代以实现所需的发射波长,但其可能削弱该化合物的稳定性。因此,考虑化合物的稳定性,重要的是分子只由基本骨架组成并且具有尽可能接近所需的发射波长的峰值发射波长。
本实施方案中,所需的发射波长区域是绿色区域,具体地,峰值发射波长为480-530nm。
根据本实施方案的有机化合物的基本骨架与其他基本骨架之间的比较
现在将根据本实施方案的有机化合物的基本骨架与下述基本骨架进行比较:
对通过用苯基取代根据本实施方案的有机化合物的基本骨架而制备的有机化合物(表1中的c)、作为式(A)所示的未取代的基本骨架的有机化合物(表1中的a)和通过用苯基取代式(B)所示的基本骨架而制备的有机化合物(表1中的b)比较发射特性。表中的符号“-”意味着在紫外和可见区中没有观察到发射。
[表1]
作为表1中的a所示的有机化合物在紫外和可见区中几乎不发光。因此,不能测定量子产率。作为表1中的b所示的有机化合物轻微地发光。但是,该化合物发出具有550nm的峰值发射波长的黄光,原因在于发光强度在0-0的振动能级低并且在另一振动能级最大化。即,该化合物具有低发光强度并且不发绿光。根据本实施方案的作为表1中的c所示的有机化合物具有高量子产率并且发出具有516nm的峰值发射波长的绿光。
因此,作为表1中的a所示的茚并[1,2,3-cd]荧蒽骨架自身不适合作为发光材料。同样地,作为表1中的b所示的有机化合物,其具有通过将苯环稠合于上述骨架而形成的基本骨架,由于其发黄光并且几乎不发光,因此不适合作为发光材料。而根据本实施方案的作为表1中的c所示的有机化合物,其具有通过在使其共轭扩展的方向上使萘环稠合于茚并[1,2,3-cd]荧蒽骨架而形成的基本骨架,发绿光并且具有高量子产率。
尽管通常认为增加用于扩展的共轭的稠环数将颜色从蓝色变为绿色、黄色和红色,但作为表1中的b所示的结构与根据本实施方案的作为表1中的c所示的结构之间的关系与上述观点不一致。即,由从 作为表1中的b所示的化合物发出的光的颜色,预期作为表1中的c所示的化合物发红光;与预期不同,本发明人已发现作为表1中的c所示的化合物发绿光。
此外,根据本实施方案的作为表1中的c所示的有机化合物的量子产率高于作为表1中的b所示的化合物至少10倍。
此外,根据本实施方案的有机化合物的基本骨架太平坦以致形成膜时可能发生分子堆叠。这导致比分子自身的发射波长长的发射波长。为了利用形成膜时分子单独的发射波长,本发明人认为重要的是将取代基引入基本骨架。根据本实施方案的有机化合物的基本骨架的平面与引入其中的取代基的平面能够形成几乎直角的二面角。特别地,将芳基引入R1、R2、R7和R8中的至少一个中是有效的。
此外,由于在其基本骨架中具有两个五元环,因此根据本实施方案的有机化合物具有深HOMO能级。即,根据本实施方案的有机化合物具有低氧化电位。因此,根据本实施方案的有机化合物对于氧化稳定。
此外,根据本实施方案的有机化合物在其基本骨架中不具有杂原子例如氮原子。这也有助于低氧化电位,即,该有机化合物对于氧化的稳定性。
根据本实施方案的有机化合物的基本骨架具有深HOMO能级。考虑HOMO和LUMO能级与能隙之间的关系,这也意味着LUMO能级深。因此,根据本实施方案的有机化合物容易接受电子。
根据本实施方案的有机化合物不仅用作绿色发光材料,而且如果基本骨架具有使发射波长长的取代基,其也用作红色发光材料。该具有较长波长的材料对于氧化稳定,原因在于其具有与根据本实施方案的有机化合物相同的基本骨架。
用于使发射波长长的取代基的实例包括三芳基胺和蒽。为了调节发射波长,能够将这样的取代基引入根据本实施方案的有机化合物的基本骨架的R4、R5、R12和R13中的至少一个。
根据本实施方案的有机化合物能够用作有机发光器件的发光层的客体或主体材料。具体地,该有机化合物能够用作发光层的客体材料,更具体地,用作绿色发光器件的发光层的客体材料。
如果将根据本实施方案的有机化合物用作发光层的客体材料,使用的主体材料能够是具有比该客体材料浅的LUMO能级的有机化合物,换言之,其LUMO能级更接近真空能级的有机化合物。这使得该客体材料更容易接受供给到主体材料的电子。
本文中使用的术语“主体材料”是指发光层的成分中具有最高重量分数的材料。本文中使用的术语“客体材料”是指发光层的成分中具有比主体材料低的重量分数并且负责发光的材料。此外,本文中使用的术语“辅助材料”是指发光层的成分中具有比主体材料低的重量分数并且辅助客体材料发光的材料。
根据本实施方案的有机化合物也能够用作红色发光层的主体材料。
此外,根据本实施方案的有机化合物能够用作发光层以外的任何层,包括空穴注入层、空穴传输层、空穴/激子阻挡层、电子传输层和电子注入层。
根据实施方案的有机化合物的实例
根据本实施方案的有机化合物的实例包括,但并不限于,下述化合物:
例示化合物组的性质
例示化合物中,由于整个分子而不仅仅是基本骨架只由烃基团组成,因此组A中的那些化合物具有低HOMO能级。这意味着这些有机化合物具有低氧化电位,因此对于氧化稳定。
另一方面,如果任何取代基具有杂原子,如组B中那样,分子的氧化电位大幅度地变化,或者分子间相互作用变化。如果任何取代基具有杂原子,其能够使最大发射波长较长。此外,如果任何取代基具有杂原子,该化合物能够用于例如如下用途:以接近100%的高浓度将其用作电子传输材料、空穴传输材料或空穴捕集发光材料。
因此,将例示化合物示为组A和B。这些化合物只具有其基本骨架的情况下发绿光。而且,根据本实施方案的有机化合物能够发出具有比绿光长的波长的光,具体地,如果将其基本骨架取代,则为红光。
具体地,根据本实施方案的有机化合物能够用通式(2)表示:
通式(2)中,R17-R24各自独立地选自具有1-4个碳原子的烷基、和芳基。
芳基为苯基、萘基、联苯基或三联苯基。
芳基能够用具有1-4个碳原子的烷基取代。
如果R17、R18、R21和R22的任何基团为芳基,其使得与根据本实施方案的有机化合物的基本骨架的二面角大。
这抑制分子堆叠,因此提供大的抑制浓度猝灭的效果。
如果R19、R20、R23或R24为取代基,其能够使发射波长较长。如果取代基为芳基,其能够使发射波长甚至更长。
合成路线的说明
现在对根据本实施方案的有机化合物的合成路线的实例进行说明。以下示出反应式。
要合成将取代基引入所需位置的化合物,能够用另一取代基将所需位置的氢原子取代。取代基的实例包括烷基、卤素原子和苯基。
合成路线1
合成路线2
其他有机化合物和原料
通过改变上述反应式中的D1-D6,能够合成各种有机化合物。表2和3示出合成的化合物的实例。
有机发光器件的说明
接下来,对根据本发明的实施方案的有机发光器件进行说明。
根据本实施方案的有机发光器件至少包括电极对,即阳极和阴极,和设置在其间的有机化合物层。该有机化合物层含有根据本发明的有机化合物。
如果有机化合物层为发光层,其能够只由根据本发明的有机化合物形成或者能够含有另一种组分。
发光层含有另一种组分的情形意味着发光层除了负责发光的组分以外还含有主体材料或辅助材料的情形。根据本发明的有机化合物能够是主体材料、客体材料或辅助材料。
如果根据本发明的有机化合物用作客体材料,主体材料中客体材料的浓度优选为0.01重量%-20重量%,更优选为0.5重量%-10重量%。
各种研究的结果,本发明人已发现使用根据本发明的有机化合物作为发光层的主体或客体材料,特别是作为客体材料而形成的器件提供具有高效率和高亮度的光学输出并且具有极高的耐久性。
现在对使用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的实例是包括其上依次设置有阳极、发光层和阴极的基板的有机发光器件。另一实例是包括依次设置的阳极、空穴传输层、电子传输层和阴极的有机发光器件。其他实例包括:包括依次设置的阳极、空穴传输层、发光层、电子传输层和阴极的有机发光器件;包括依次设置的阳极、空穴注入层、空穴传输层、发光层、电子传输层和阴极的有机发光器件;和包括依次设置的阳极、空穴传输层、发光层、空穴/激子阻挡层、电子传输层和阴极的有机发光器件。但是,这些实例只是基本器件结构,并且根据本实施方案的有机发光器件的结构并不限于此;能够采用各种层结构,包括例如在电极和有机化合物层之间的界面包括绝缘层的结构、包括粘合层或干涉层的结构和包括由具有不同的电离电位的两层组成的电子或空穴传 输层的结构。
除了根据本发明的有机化合物以外,能够任选使用其他化合物,包括已知的低分子量或聚合物空穴注入化合物或空穴传输化合物、已知的低分子量或聚合物主体化合物或发光化合物(主体材料)、和已知的低分子量或聚合物电子注入化合物或电子传输化合物。
以下示出这样的化合物的实例。
使用的空穴注入化合物或空穴传输化合物能够是具有高空穴迁移率的材料。具有空穴注入性或空穴传输性的低分子量或聚合物材料的实例包括,但并不限于,三芳基胺、苯二胺、1,2-二苯乙烯、酞菁、卟啉、聚乙烯基咔唑、聚噻吩和其他导电聚合物。
表4示出主体化合物的具体结构式。作为主体化合物,能够使用具有表4中所示的结构式的衍生物。其他实例包括,但并不限于,稠环化合物(例如芴、萘、蒽、芘、咔唑、喹喔啉和喹啉)、有机铝络合物例如三(8-羟基喹啉合)铝、有机锌络合物、三苯基胺和聚合物例如聚芴和聚亚苯基。
[表4]
考虑例如与空穴注入化合物或空穴传输化合物的空穴迁移率的平衡来选择使用的电子注入化合物或电子传输化合物。具有电子注入性或电子传输性的化合物的实例包括,但并不限于,二唑、唑、吡嗪、三唑、三嗪、喹啉、喹喔啉、菲咯啉和有机铝络合物。
使用的阳极材料能够是具有较高功函数的材料。这样的材料的实例包括金属例如金、铂、银、铜、镍、钯、钴、硒、钒和钨以及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(IZO)。也能够使用导电聚合物例如聚苯胺、聚吡咯和聚噻吩。这些电极材料能够单独使用或者组合使用。阳极能够具有单层结构或多层结构。
另一方面,使用的阴极材料能够是具有较低功函数的材料。这样的材料的实例包括碱金属例如锂;碱土金属例如钙;和金属例如铝、钛、锰、银、铅和铬。这些金属的合金也能够使用,包括镁-银、铝- 锂和铝-镁。此外,能够使用金属氧化物例如ITO。这些电极材料能够单独使用或组合使用。阴极能够具有单层结构或多层结构。
根据本实施方案的有机发光器件中,含有根据本发明的有机化合物的层和其他有机化合物层通常采用真空沉积、离子辅助沉积、溅射、等离子体辅助沉积或使用适当的溶剂形成薄膜的已知的涂布法(例如旋转涂布、浸渍、流延、Langmuir-Blodgett(LB)技术或喷墨涂布)形成。如果采用真空沉积或溶液涂布形成这些层,它们具有优异的经时稳定性,原因在于,例如,结晶不倾向发生。如果采用涂布形成这些层,能够与适当的粘结剂树脂组合形成这些膜。
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、丙烯腈-丁二烯-苯乙烯(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。这些粘结剂树脂能够作为均聚物或共聚物单独使用或者能够作为两种以上的混合物使用。此外,能够将已知的添加剂例如增塑剂、抗氧化剂和紫外线吸收剂任选地组合使用。
包括有机发光器件的显示装置
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或照明装置。其他用途包括用于电子照相图像形成装置的曝光光源和用于液晶显示装置的背光。
显示装置包括显示单元,显示单元包括根据本实施方案的有机发光器件。显示单元具有多个像素。这些像素包括根据本实施方案的有机发光器件和用作开关器件的实例的薄膜晶体管(TFT)。将有机发光器件的阳极或阴极与TFT的漏电极或源电极连接。显示装置能够用作例如用于个人电脑的图像显示装置。显示装置也能够构成为进一步包括图像输入单元的图像输入装置。
图像输入装置包括用于从例如面阵电荷耦合器件(CCD)传感器、线阵CCD传感器或存储卡输入信息的图像输入单元和用于显示输入的信息的显示单元。图像输入装置也能够构成为还包括摄像光学系统的 摄像装置,例如数码相机。对于摄像装置或喷墨打印机,显示装置能够具有基于从外部输入的图像信息显示图像以用作显示单元的图像输出功能和基于对图像进行处理输入信息以用作控制面板的输入功能两者。显示装置也能够用作多功能打印机的显示单元。
接下来,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是根据本实施方案的有机发光器件和用作控制有机发光器件的开/关或发光强度的开关器件的实例的TFT的截面示意图。图1表示两对有机发光器件和TFT。尽管没有图示,该显示装置能够包括用于控制发光强度的晶体管。通过基于信息驱动开关器件来打开和关闭有机发光器件,显示装置显示信息。现在对详细的结构进行说明。
图1中的显示装置包括基板1,例如玻璃基板,和用于保护TFT8和有机化合物层12的设置在基板1上的防湿膜2,还包括金属栅极3、栅极绝缘体4和半导体层5。
TFT 8包括半导体层5、漏电极6和源电极7。在TFT 8上设置绝缘膜9。将有机发光器件的阳极11经由接触孔10与源电极7连接。显示装置的结构并不限于上述结构,能够为将阳极11或阴极13与TFT8的源电极7或漏电极6连接的任何结构。
尽管为了图示,在图1中将它们表示为单层,但有机化合物层12均由多个有机化合物层组成。将第一保护层14和第二保护层15设置在阴极13上以抑制有机发光器件的劣化。
根据本实施方案的显示装置的开关器件能够是任何类型。例如,能够使用单晶硅基板、金属-绝缘体-金属(MIM)器件或无定形硅(a-Si)器件。
实施例
实施例1
例示化合物A2的合成
在200mL乙醇中放入10.6g(50mmol)E1和10.5g(50mmol)E2。将该溶液加热到60℃后,滴加20mL的6M氢氧化钠水溶液。添加完成时,将该溶液加热到80℃并且搅拌2小时。冷却后,将沉淀物过滤出,用水和乙醇洗涤,并且通过在减压下在80℃下加热来进行干燥以得到18.7g深绿色固体E3(收率:86%)。接下来,将8.71g(20mmol)E3和4.49g(24mmol)E4放入100mL甲苯中。将该溶液加热到80℃后,逐渐滴加2.81g(24mmol)亚硝酸异戊酯,并且将该溶液在110℃下搅拌3小时。冷却后,用100mL水将该溶液洗涤两次。用饱和盐水洗涤有机层并且在硫酸镁上干燥。然后将该溶液过滤,并且将滤液浓缩以得到深棕色液体。通过柱色谱(甲苯/庚烷,2:3)对其进行纯化并且从氯仿/甲醇中重结晶以得到7.47g黄色晶体E5(收率:70%)。
在40mL的DMF中放入2.67g(5mmol)E5和1.60g(8mmol)E6。将0.25g(0.5mmol)的双(三苯基膦)钯(II)二氯化物和2.28g(15mmol)的1,8-二氮杂双环[5.4.0]十一碳-7-烯放入该溶液中后,将其加热到150℃并且搅拌4小时。冷却后,通过添加30mL甲醇而形成沉淀物并且将其过滤出以得到黄色固体。通过柱色谱(氯仿/庚烷,1:3)将该固体纯化并且从氯仿/甲醇中重结晶两次以得到1.77g黄色晶体的例示化合物A2(收率:67%)。
通过高性能液相色谱(HPLC),该化合物的纯度确定为不小于99%。
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下 通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A2的甲苯溶液的发射光谱。得到的光谱在516nm具有其最大强度。
实施例2
例示化合物A22的合成
除了将实施例1中使用的有机化合物E2变为E7以外,通过与实施例1中相同的反应和纯化程序制备例示化合物A22:
通过HPLC,该化合物的纯度确定为不小于99.5%。
此外,通过核磁共振(NMR)波谱法考察该化合物的结构。
1H NMR(CDCl3,400MHz)σ(ppm):8.17(s,2H),7.84-7.82(m,2H),7.70-7.67(m,2H),7.65-7.63(m,2H),7.49(s,2H),7.48(s,2H),7.46(d,2H,J=7.60Hz),7.39-7.37(m,2H),7.21-7.17(m,2H),6.40(d,2H,J=7.20Hz),1.44(s,36H)。
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A22的甲苯溶液的发射光谱。得到的光谱在517nm具有其最大强度。
实施例3
例示化合物A3的合成
在100mL甲苯中放入5.41g(20mmol)E8和5.18g(24mmol)E9。将该溶液加热到80℃后,逐渐滴加2.81g(24mmol)亚硝酸异戊酯,并且将该溶液逐渐从80℃加热且在100℃下搅拌3小时。冷却后,用100mL水将该溶液洗涤两次。用饱和盐水洗涤有机层并且在硫酸镁上 干燥。然后将该溶液过滤,并且将滤液浓缩以得到深棕色液体。通过柱色谱(甲苯/庚烷,2:3)将其纯化并且从甲苯/乙醇中重结晶以得到3.77g的E10(收率:46%)。
接下来,将4.1g(10mmol)的E10和1.08g(2mmol)的Ni(dppp) 2Cl2放入100mL甲苯中,将3.03g(30mmol)的三乙胺和3.83g(30mmol)的E11放入该溶液中,并且在100℃下将其搅拌5小时。冷却后,将该溶液过滤并且用100mL水洗涤两次。用饱和盐水将有机层洗涤并且在硫酸镁上干燥。然后将该溶液过滤,并且将滤液浓缩以得到深棕色液体。通过柱色谱(甲苯/庚烷,5:1)对其进行纯化并且从甲苯/庚烷中重结晶以得到3.19g的E12(收率:70%)。
在50mL的DMF中放入2.28g(5mmol)的E12和2.86g(10mmol)的E13。将0.25g(0.5mmol)的双(三苯基膦)钯(II)二氯化物和2.28g(15mmol)的1,8-二氮杂双环[5.4.0]十一碳-7-烯放入该溶液中后,将其加热到150℃并且搅拌4小时。冷却后,通过添加30mL甲醇来形成沉淀物并且过滤出以得到黄色固体。通过柱色谱(氯仿/庚烷,1:5)对该固体进行纯化并且从甲苯/甲醇中重结晶两次以得到3.27g黄色晶体E14(收率:72%)。接下来,将3.18g(7mmol)的E14和1.25g(7mmol)的E15放入50mL氯仿中,并且将该溶液加热到60℃且搅拌8小时。冷却后,用50mL水将该溶液洗涤两次。用饱和盐水对有机层进行洗涤并且在硫酸镁上干燥。然后将该溶液过滤,并且将滤液浓缩。通过柱色谱(氯仿/庚烷,1:2)对其进行纯化并且从甲苯/乙醇中重结晶以得到3.17g的E16(收率:85%)。
在40mL的DMF中放入2.42g(5mmol)的E16和1.60g(8mmol)的E17。将0.25g(0.5mmol)的双(三苯基膦)钯(II)二氯化物和2.28g(15mmol)的1,8-二氮杂双环[5.4.0]十一碳-7-烯放入该溶液中后,将其加热到150℃并且搅拌4小时。冷却后,通过添加30mL甲醇来形成沉淀物并且过滤出以得到黄色固体。通过柱色谱(氯仿/庚烷,1:3)对该固体进行纯化并且从氯仿/甲醇中重结晶两次以得到1.90g黄色晶体的例示化合物A3(收率:72%)。
通过HPLC,该化合物的纯度确定为不小于99%。
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A3的甲苯溶液的发射光谱。得到的光谱在524nm具有其最大强度。
实施例4
例示化合物A23的合成
除了将实施例3中使用的有机化合物E8变为E18以外,进行与实施例3中相同的反应和纯化程序:
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A23的甲苯溶液的发射光谱。得到的光谱在525nm具有其最大强度。
实施例5
例示化合物A13的合成
除了将实施例1中使用的有机化合物E2变为E19以外,通过与实施例1中相同的反应和纯化程序制备例示化合物A13:
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A13的甲苯溶液的发射光谱。得到的光谱在517nm具有其最大强度。
实施例6
例示化合物A21的合成
除了将实施例1中使用的有机化合物E6变为E20以外,进行与实施例1中相同的反应和纯化程序:
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A21的甲苯溶液的发射光谱。得到的光谱在523nm具有其最大强度。
实施例7
例示化合物A25的合成
除了将实施例1中使用的有机化合物E6变为E20,并且将E2变为E7以外,进行与实施例1中相同的反应和纯化程序。
使用可由Hitachi,Ltd.得到的F-4500,在350nm的激发波长下通过光致发光波谱法测定具有1×10-5mol/L的浓度的例示化合物A25的甲苯溶液的发射光谱。得到的光谱在520nm具有其最大强度。
实施例8
本实施例中制备的有机发光器件包括依次设置的阳极、空穴传输层、发光层、空穴/激子阻挡层、电子传输层和阴极。首先,在玻璃基板上形成具有100nm的厚度的ITO膜的图案。然后通过使用电阻加热的真空沉积在10-5Pa的压力的真空室内在基板上连续地形成下述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(40nm):G-1
发光层(30nm):主体:化合物H7(98重量%);客体:例示化合物A2(2重量%)
空穴/激子阻挡层(10nm):G-3
电子传输层(30nm):G-4
第一金属电极层(1nm):LiF
第二金属电极层(100nm):铝
使用可由Hewlett-Packard Company得到的4140B pA计测定有机发光器件的电流-电压特性,并且使用可由Topcon Corporation得到的BM7测定器件的发光强度。
实施例9-20
实施例9-20中,除了改变客体和主体材料以外,以与实施例8 中相同的方式制备有机发光器件,并且同样地评价。使用的主体材料是表5的“G-2”栏中所示的化合物。
表5示出实施例8-20的发光效率和电压。
[表5]
客体 | G-2 | 发光效率(cd/A) | 电压(V) | |
实施例8 | A2 | H7 | 16 | 4.5 |
实施例9 | A2 | H28 | 20 | 4.7 |
实施例10 | A3 | H13 | 18 | 4.2 |
实施例11 | A13 | H10 | 20 | 4.9 |
实施例12 | A22 | H8 | 20 | 4.6 |
实施例13 | A22 | H17 | 23 | 4.8 |
实施例14 | A23 | H21 | 20 | 4.6 |
实施例15 | A23 | H24 | 18 | 4.7 |
实施例16 | A24 | H6 | 17 | 4.5 |
实施例17 | A25 | H7 | 22 | 4.6 |
实施例18 | A25 | H15 | 24 | 4.6 |
实施例19 | A44 | H3 | 16 | 4.7 |
实施例20 | A45 | H2 | 20 | 4.6 |
实施例21
本实施例中制备的有机发光器件包括依次设置的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极。
通过以下过程制备具有共振结构的有机发光器件。
通过溅射在用作支撑体的玻璃基板上将铝合金(铝-钕)沉积为100nm的厚度以形成反射阳极。然后通过溅射将ITO沉积为80nm的厚度以形成透明阳极。接下来,在阳极周围形成具有1.5μm的厚度的丙烯酸系器件隔离膜,并且形成了具有3mm的半径的开口。用丙酮,然后用异丙醇(IPA)对基板进行超声清洁,然后用沸腾的IPA洗涤并且干燥。然后对基板的表面进行紫外线/臭氧清洁。
随后,通过使用电阻加热的真空沉积,在10-5Pa的压力的真空室内在基板上连续地形成下述有机层,然后通过溅射将IZO沉积为30nm的厚度以形成透明电极作为阴极。形成了阴极后,在氮气氛中将该器件密封。
以这种方式形成了有机发光器件。
空穴注入层(135nm):G-11
空穴传输层(10nm):G-12
发光层(35nm):主体:化合物H7(98重量%);客体:例示化合物A13(2重量%)
电子传输层(10nm):G-14
电子注入层(70nm):G-15(80重量%),锂(20重量%)
使用可由Hewlett-Packard Company得到的4140B pA计测定有机发光器件的电流-电压特性,并且使用可由Topcon Corporation得到的BM7测定器件的发光强度。
实施例22-26
实施例22-26中,
除了改变客体和主体材料以外,以与实施例21中同样的方式制备有机发光器件,并且同样地评价。使用的主体材料是表6的“G-13” 栏中所示的化合物。
表6示出实施例21-26的发光效率和电压。
[表6]
客体 | G-13 | 发光效率(cd/A) | 电压(V) | |
实施例21 | A13 | H7 | 22 | 4.5 |
实施例22 | A22 | H8 | 25 | 4.3 |
实施例23 | A23 | H6 | 24 | 4.1 |
实施例24 | A24 | H10 | 24 | 4.1 |
实施例25 | A25 | H22 | 26 | 4.0 |
实施例26 | A44 | H21 | 25 | 4.2 |
结果和讨论
根据本发明的实施方案的有机化合物是新型化合物,其具有高量子产率,发适合作为绿光的光,并且能够用于制备具有优异的发射特性的有机发光器件。
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6月4日提交的日本专利申请No.2010-129267的权益,在此通过引用将其全文并入本文。
附图标记列表
8 TFT
11 阳极
12 有机化合物层
13 阴极 。
Claims (10)
1.由通式(1)表示的有机化合物:
其中R1-R16各自独立地选自氢原子、具有1-4个碳原子的烷基和苯基,其中该苯基可具有1-4个碳原子的烷基作为取代基。
2.根据权利要求1的有机化合物,其中,R1、R2、R7和R8的至少一个为苯基,该苯基可具有1-4个碳原子的烷基作为取代基。
3.由下述结构表示的有机化合物:
4.有机发光器件,包括:
阳极;
阴极;和
设置在该阳极和该阴极之间的有机化合物层,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:
阳极;
阴极;和
设置在该阳极和该阴极之间的有机化合物层,该有机化合物层含有根据权利要求2的有机化合物。
6.有机发光器件,包括:
阳极;
阴极;和
设置在该阳极和该阴极之间的有机化合物层,该有机化合物层含有根据权利要求3的有机化合物。
7.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。
8.根据权利要求7的有机发光器件,其中该有机发光器件发绿光。
9.显示装置,其具有多个像素,每个像素包括根据权利要求4~8的任一项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:
用于输入图像的图像输入单元;和
用于显示该图像的显示单元,该显示单元具有多个像素,每个像素包括根据权利要求4~8的任一项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 |
---|---|---|---|
JP2010-129267 | 2010-06-04 | ||
JP2010129267A JP5627300B2 (ja) | 2010-06-04 | 2010-06-04 | 新規有機化合物およびそれを有する有機発光素子 |
PCT/JP2011/062644 WO2011152477A1 (en) | 2010-06-04 | 2011-05-26 | Novel organic compound and organic light-emitting device including the same |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102933529A CN102933529A (zh) | 2013-02-13 |
CN102933529B true CN102933529B (zh) | 2015-05-13 |
Family
ID=45066834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180027516.XA Active CN102933529B (zh) | 2010-06-04 | 2011-05-26 | 有机化合物和包括该有机化合物的有机发光器件 |
Country Status (8)
Country | Link |
---|---|
US (1) | US9145344B2 (zh) |
EP (1) | EP2576487B1 (zh) |
JP (1) | JP5627300B2 (zh) |
KR (1) | KR101513789B1 (zh) |
CN (1) | CN102933529B (zh) |
BR (1) | BR112012030833B1 (zh) |
RU (1) | RU2510390C1 (zh) |
WO (1) | WO2011152477A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3489325B1 (en) | 2013-12-05 | 2020-06-10 | LG Display Co., Ltd. | Organic electroluminescent device |
JP7109049B2 (ja) | 2018-03-20 | 2022-07-29 | セイキ住工株式会社 | 横引きスクリーン装置における可動框のロック機構 |
KR102383315B1 (ko) | 2018-03-30 | 2022-04-06 | 캐논 가부시끼가이샤 | 유기발광소자, 표시장치, 촬상 장치 및 조명 장치 |
JP7130491B2 (ja) * | 2018-08-10 | 2022-09-05 | キヤノン株式会社 | 有機化合物、有機発光素子、表示装置、撮像装置、電子機器、照明装置及び移動体 |
KR20200086782A (ko) * | 2019-01-09 | 2020-07-20 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 이를 포함하는 표시 장치 |
JP7254552B2 (ja) * | 2019-02-13 | 2023-04-10 | キヤノン株式会社 | 有機化合物及び有機発光素子 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008235734A (ja) * | 2007-03-23 | 2008-10-02 | Mitsui Chemicals Inc | 有機トランジスタ |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU1434717C (ru) * | 1986-12-23 | 1992-10-30 | Предприятие П/Я Р-6496 | 4-[1-(4-Сульфамилфенил)-5-фенил-2-пиразолинил-3]-1,8-нафтоилен-1 @ ,2 @ ,-бензимидазол в качестве люминесцирующего соединени красного свечени и люминесцирующа композици на его основе дл крашени полиэтилена |
JP3794819B2 (ja) * | 1997-04-18 | 2006-07-12 | 三井化学株式会社 | フルオランテン誘導体および有機電界発光素子 |
JP3801308B2 (ja) * | 1997-06-06 | 2006-07-26 | 三井化学株式会社 | 有機電界発光素子 |
JP2000311786A (ja) * | 1999-04-27 | 2000-11-07 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
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 |
TW200902676A (en) * | 2007-02-19 | 2009-01-16 | Idemitsu Kosan Co | Organic electroluminescent device |
DE602008004457D1 (de) * | 2007-03-09 | 2011-02-24 | Canon Kk | Organische lichtemittierende vorrichtung |
JP2008300753A (ja) * | 2007-06-04 | 2008-12-11 | Mitsui Chemicals Inc | 有機トランジスタ |
RU2368641C2 (ru) * | 2007-11-08 | 2009-09-27 | Некоммерческая организация Учреждение Институт проблем химической физики Российской академии наук (статус государственного учреждения) (ИПХФ РАН) | Электролюминесцентный материал, содержащий органическое люминесцентное вещество |
US20140231787A1 (en) * | 2011-09-22 | 2014-08-21 | Canon Kabushiki Kaisha | White organic el element and illuminating apparatus and display apparatus using the same |
-
2010
- 2010-06-04 JP JP2010129267A patent/JP5627300B2/ja active Active
-
2011
- 2011-05-26 WO PCT/JP2011/062644 patent/WO2011152477A1/en active Application Filing
- 2011-05-26 KR KR1020127033771A patent/KR101513789B1/ko active IP Right Grant
- 2011-05-26 BR BR112012030833A patent/BR112012030833B1/pt not_active IP Right Cessation
- 2011-05-26 RU RU2012155225/04A patent/RU2510390C1/ru active
- 2011-05-26 CN CN201180027516.XA patent/CN102933529B/zh active Active
- 2011-05-26 EP EP11789879.1A patent/EP2576487B1/en active Active
- 2011-05-26 US US13/701,665 patent/US9145344B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008235734A (ja) * | 2007-03-23 | 2008-10-02 | Mitsui Chemicals Inc | 有機トランジスタ |
Also Published As
Publication number | Publication date |
---|---|
EP2576487B1 (en) | 2015-07-08 |
EP2576487A4 (en) | 2013-12-25 |
WO2011152477A1 (en) | 2011-12-08 |
KR101513789B1 (ko) | 2015-04-20 |
JP5627300B2 (ja) | 2014-11-19 |
US20130076604A1 (en) | 2013-03-28 |
JP2011256113A (ja) | 2011-12-22 |
RU2510390C1 (ru) | 2014-03-27 |
KR20130040938A (ko) | 2013-04-24 |
CN102933529A (zh) | 2013-02-13 |
US9145344B2 (en) | 2015-09-29 |
BR112012030833A2 (pt) | 2016-11-16 |
BR112012030833B1 (pt) | 2018-09-25 |
EP2576487A1 (en) | 2013-04-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8962158B2 (en) | Material having indolocarbazole compound for phosphorescent light-emitting element and organic electroluminescent element using the same | |
US9019328B2 (en) | Organic compound, organic light-emitting device, and display apparatus | |
CN102405200B (zh) | 有机化合物、发光器件和图像显示装置 | |
US7973306B2 (en) | Anthracene derivatives, organic electronic devices using anthracene derivatives, and electronic apparatuses comprising organic electronic device | |
CN101870705B (zh) | 有机化合物、发光器件和图像显示装置 | |
CN102992942B (zh) | 有机化合物和具有该有机化合物的有机发光器件 | |
JP5687628B2 (ja) | 青色または緑色ルミネセンス用途のクリセン化合物 | |
CN103313958B (zh) | 有机化合物、有机电致发光元件和图像显示装置 | |
JP5773638B2 (ja) | 縮合多環化合物及びこれを用いた有機発光素子 | |
CN102933529B (zh) | 有机化合物和包括该有机化合物的有机发光器件 | |
US20170133598A1 (en) | Novel organic compound, organic light emitting device, and image display device | |
EP3527564A1 (en) | Novel heterocyclic compound and organic light emitting element using same | |
CN102245545B (zh) | 有机化合物 | |
CN102869636A (zh) | 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 | |
KR20140080451A (ko) | 중수소로 치환된 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
US20150243909A1 (en) | Blue luminescent compounds | |
JP5783879B2 (ja) | 新規有機化合物および有機発光素子 | |
US9166173B2 (en) | Organic compound | |
CN108807697B (zh) | 有机电致发光器件和菲衍生物 | |
US20120013700A1 (en) | Novel fused polycyclic compound and organic light-emitting device including the same | |
US9590183B2 (en) | Organic compound and organic light-emitting device including the same | |
CN103328419A (zh) | 有机化合物、有机发光器件和图像显示装置 | |
EP2419391B1 (en) | Novel fused polycyclic compound and organic light emitting device |
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 |