CN114230597B - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
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- CN114230597B CN114230597B CN202111644439.4A CN202111644439A CN114230597B CN 114230597 B CN114230597 B CN 114230597B CN 202111644439 A CN202111644439 A CN 202111644439A CN 114230597 B CN114230597 B CN 114230597B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims description 38
- 239000010409 thin film Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 16
- 230000005540 biological transmission Effects 0.000 abstract description 12
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
- -1 polycyclic aromatic compound Chemical class 0.000 abstract description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 7
- 229910052796 boron Inorganic materials 0.000 abstract description 6
- 230000002349 favourable effect Effects 0.000 abstract description 6
- 238000007738 vacuum evaporation Methods 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 4
- 230000002776 aggregation Effects 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract description 4
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000005191 phase separation Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000003003 spiro group Chemical group 0.000 abstract description 2
- 230000003313 weakening effect Effects 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000007806 chemical reaction intermediate Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 6
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- 102100020895 Ammonium transporter Rh type A Human genes 0.000 description 3
- 101100087409 Arabidopsis thaliana RH18 gene Proteins 0.000 description 3
- 101100248236 Arabidopsis thaliana RH33 gene Proteins 0.000 description 3
- 101100248237 Arabidopsis thaliana RH34 gene Proteins 0.000 description 3
- 101100301843 Arabidopsis thaliana RH49 gene Proteins 0.000 description 3
- 101100301844 Arabidopsis thaliana RH50 gene Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 101100125689 Oryza sativa subsp. japonica EIF4A3B gene Proteins 0.000 description 3
- 101150089059 RH17 gene Proteins 0.000 description 3
- 101150107345 Rhag gene Proteins 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical class 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material 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
- 238000004140 cleaning Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 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
- 238000005265 energy consumption Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 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
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic compound and application thereof, wherein the compound is a condensed aromatic derivative containing boron and nitrogen, the compound utilizes heterogeneous elements such as boron, nitrogen and the like to connect aromatic condensed rings to form a polycyclic aromatic compound with a large conjugated plane, the polycyclic aromatic compound has higher luminous efficiency, aggregation among molecules can be effectively inhibited by introducing substituents, the phenomenon of fluorescence weakening caused by aggregation is avoided, the luminous efficiency of a device is improved, and simultaneously, the triplet state energy level of the molecules can be effectively regulated and controlled, and the service life of the device is effectively prolonged. The spiro structure can also enable the compound to obtain higher thermal stability and glass transition temperature Tg, which is beneficial to forming a stable and uniform film in the thermal vacuum evaporation process, and meanwhile, phase separation is reduced, and the stability of the device is maintained. The device has higher carrier transmission rate and balanced carrier transmission performance, is favorable for balancing hole and electron transmission in the device, and simultaneously obtains a wider carrier composite region, thereby improving luminous efficiency.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
With the continuous advancement of the field of illumination and display of OLEDs, research on core materials thereof is also focused on, because an OLED device with good efficiency and long service life is usually the result of optimized matching of device structures and various organic materials. In order to prepare the OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be continuously researched and innovated so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
The core organic luminescent material of the OLED display technology is based on the mixture of a red light material, a green light material and a blue light material to realize the full color gamut. The development of novel luminescent materials is a source force for promoting the continuous progress of electroluminescent technology and is also a research hotspot of the organic electroluminescent industry. At present, multiple vibration effects are adopted, and vibration of boron, nitrogen, oxygen and other hetero atoms is utilized to construct a polycyclic aromatic compound formed by condensing a plurality of aromatic rings by a single boron atom, nitrogen, oxygen and other hetero atoms, namely, a special rigid material system containing boron atoms, nitrogen, oxygen and other hetero atoms is prepared. The fluorescent molecules realize lower lighting voltage, high luminous efficiency and better service life of the device.
In view of this, the present invention has been made.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide an organic compound and application thereof.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
it is an object of the present invention to provide an organic compound having a structure as shown in formula I:
wherein R is 1 -R 7 Independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or substitutedOr unsubstituted C2-C20 unsaturated hydrocarbon groups.
In the invention, the organic compound has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of the device. The device has higher carrier transmission rate and balanced carrier transmission performance, is favorable for balancing hole and electron transmission in the device, and simultaneously obtains a wider carrier composite region, thereby improving luminous efficiency.
In the present invention, the C6-C30 may be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.
The C5-C30 may be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.
The C2-C20 may be C2, C4, C5, C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.
It is a second object of the present invention to provide an organic electroluminescent material comprising an organic compound according to one of the objects.
It is a further object of the present invention to provide a light-emitting layer material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising an organic compound according to one of the objects.
It is a fifth object of the present invention to provide a display panel comprising an OLED device as defined in object four.
A sixth object of the present invention is to provide an organic light emitting display device including the display panel as set forth in fifth object.
Compared with the prior art, the invention has the following beneficial effects:
the condensed aromatic derivative containing boron and nitrogen, which is disclosed by the invention, is a polycyclic aromatic compound with a large conjugated plane, which is formed by connecting aromatic condensed rings by utilizing heterogeneous elements such as boron, nitrogen and the like, has higher luminous efficiency, and can effectively inhibit intermolecular aggregation by introducing substituents, avoid fluorescence weakening phenomenon caused by aggregation, improve the luminous efficiency of a device, and simultaneously can effectively regulate and control the triplet state energy level of molecules and effectively prolong the service life of the device. The spiro structure can also enable the compound to obtain higher thermal stability and glass transition temperature Tg, which is beneficial to forming a stable and uniform film in the thermal vacuum evaporation process, and meanwhile, phase separation is reduced, and the stability of the device is maintained. The device has higher carrier transmission rate and balanced carrier transmission performance, is favorable for balancing hole and electron transmission in the device, and simultaneously obtains a wider carrier composite region, thereby improving luminous efficiency.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device according to the present invention, in which 1 is a substrate, 2 is an ITO anode, 3 is a first hole transport layer, 4 is a second hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a first electron transport layer, 8 is a second electron transport layer, 9 is a cathode, 10 is a cap layer, and the direction of the arrow represents the light emitting direction of the device.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
It is an object of the present invention to provide an organic compound having a structure as shown in formula I:
wherein R is 1 -R 7 Independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or substituted or unsubstituted C2-C20 unsaturated hydrocarbyl.
In the invention, the organic compound has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of the device. The device has higher carrier transmission rate and balanced carrier transmission performance, is favorable for balancing hole and electron transmission in the device, and simultaneously obtains a wider carrier composite region, thereby improving luminous efficiency.
In the present invention, the C6-C30 may be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.
The C5-C30 may be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.
The C2-C20 may be C2, C4, C5, C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.
In one embodiment, R 1 Phenyl substituted with a phenyl, pyridinyl or C1-C5 (e.g., C1, C2, C3, C4 or C5) alkyl group.
In one embodiment, R 2 -R 7 Independently selected from the group consisting of hydrogen, C1-C5 (e.g., C1, C2, C3, C4, or C5) alkyl, C1-C5 alkyl-substituted phenyl, C1-C5 alkyl, and cyano-substituted phenyl, pyridinyl, quinolinyl, Wherein the wavy line represents the attachment site of the group.
In one embodiment, the substituents in the substituted C6-C30 aryl, substituted C5-C30 heteroaryl, or substituted C2-C20 unsaturated hydrocarbyl are selected from protium, deuterium, methyl, isopropyl, t-butyl, cyano, or halogen.
In one embodiment, the organic compound is any one of the following compounds:
it is a second object of the present invention to provide an organic electroluminescent material comprising an organic compound according to one of the objects.
It is a further object of the present invention to provide a light-emitting layer material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising an organic compound according to one of the objects.
In the OLED device provided by the invention, the anode material can be metal, metal oxide or conductive polymer; wherein the metal comprises copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof, the metal oxide comprises Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide, indium Gallium Zinc Oxide (IGZO) and the like, and the conductive polymer comprises polyaniline, polypyrrole, poly (3-methylthiophene) and the like. In addition to the above materials and combinations thereof that facilitate hole injection, materials known to be suitable as anodes are included.
In the OLED device, the cathode material may be a metal or a multi-layer metal material; wherein the metal comprises aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys, and the multilayer metal material comprises LiF/Al, liO 2 /Al、BaF 2 Al, etc. Materials suitable for use as cathodes are also known in addition to the above materials that facilitate electron injection and combinations thereof.
In the OLED device, the organic thin film layer includes at least one light emitting layer (EML) and any one or a combination of at least two of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), or an Electron Injection Layer (EIL) disposed at both sides of the light emitting layer. In addition to the organic compound according to one of the objects of the present invention, the hole/electron injection and transport layer may be a carbazole compound, an arylamine compound, a benzimidazole compound, a metal compound, or the like. A cap layer (CPL) may also optionally be provided on the cathode (the side remote from the anode) of the OLED device.
In one embodiment, the organic thin film layer includes a light emitting layer including a host material including an organic compound according to one of the objects and a doping material.
The OLED device can be prepared by the following method: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. Among them, known film forming methods such as vapor deposition, sputtering, spin coating, dipping, ion plating, and the like can be used for forming the organic thin layer.
It is a fifth object of the present invention to provide a display panel comprising an OLED device as defined in object four.
A sixth object of the present invention is to provide an organic light emitting display device including the display panel as set forth in fifth object.
The following are illustrative examples of the preparation of the organic compounds according to the invention:
example 1
Synthesis of intermediate d-1
In a nitrogen atmosphere, 1, 2-dichlorobenzene as a reaction solvent was added, a reaction intermediate a-1 (2 mmol), a reaction intermediate b-1 (2.2 mmol), potassium carbonate (7 mmol), cuI (0.5 mmol) as a catalyst and 18-crown-6 (0.5 mmol) as a ligand were sequentially added, and the mixture was heated to 100℃and reacted for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic phase was collected by suction filtration, followed by addition of dichloromethane/H 2 O was extracted, and the collected organic phase was extracted with anhydrous Na 2 SO 4 Drying, suction filtering, collecting filtrate, spin-removing solvent, and purifying by column chromatography to obtain intermediate c-1.
A solution of t-butyllithium in pentane (8.0 mL,1.70M,13.5 mmol) was slowly added to a solution of c-1 (2.40 mmol) in t-butylbenzene (100 mL) at-78deg.C, followed by a reaction at 60℃for 4 hours. After the reaction was completed, the temperature was lowered to-78℃and boron tribromide (15 mmol) was slowly added thereto, followed by stirring at room temperature for 1 hour. N, N-diisopropylethylamine (20 mmol) was added at room temperature and the reaction was stopped after a further 6 hours at 145 ℃. And (3) spin-drying the solvent in vacuum and performing column chromatography purification to obtain a target intermediate d-1.
MALDI-TOF: m/z: C43H26BFN2:600.22, test value was 600.00.
Compound elemental analysis results: calculated value C,86.01; h,4.36; b,1.80; f,3.16; n,4.67; test value: c,86.01; h,4.36; b,1.80; f,3.16; n,4.67.
Synthesis of RH02
In a round-bottomed flask, intermediate d-1 (4 mmol), compound e-1 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. Cooling the resulting mixture to room temperature, addingIn water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the desired product RH02.
MALDI-TOF: m/z: C58H36BN5:813.31, test value 813.25.
Compound elemental analysis results: calculated value C,85.61; h,4.46; b,1.33; n,8.61; test value: c,85.62; h,4.45; b,1.33; n,8.61.
Example 2: synthesis of Compound RH33
In a round-bottomed flask, intermediate d-1 (4 mmol), compound e-4 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH33.
MALDI-TOF: m/z: C64H40BN5:889.34, test value 889.30.
Compound elemental analysis results: calculated value C,86.38; h,4.53; b,1.21; n,7.87; test value: c,86.37; h,4.54; b,1.21; n,7.87.
Example 3: synthesis of Compound RH49
In a round-bottomed flask, intermediate d-1 (4 mmol), compound e-5 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was returned under nitrogen atmosphereThe reaction was carried out for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH49.
MALDI-TOF: m/z: C63H39BN4:862.33, test value 862.30.
Compound elemental analysis results: calculated C,87.70; h,4.56; b,1.25; n,6.49; test value: c,87.69; h,4.57; b,1.24; n,6.50.
Example 4:
synthesis of intermediate d-2
In a nitrogen atmosphere, 1, 2-dichlorobenzene as a reaction solvent was added, a reaction intermediate a-2 (2 mmol), a reaction intermediate b-2 (2.2 mmol), potassium carbonate (7 mmol), cuI (0.5 mmol) as a catalyst and 18-crown-6 (0.5 mmol) as a ligand were sequentially added, and the mixture was heated to 100℃and reacted for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic phase was collected by suction filtration, followed by addition of dichloromethane/H 2 O was extracted, and the collected organic phase was extracted with anhydrous Na 2 SO 4 Drying, suction filtering, collecting filtrate, spin-removing solvent, and purifying by column chromatography to obtain intermediate c-2.
A solution of t-butyllithium in pentane (8.0 mL,1.70M,13.5 mmol) was slowly added to a solution of c-2 (2.40 mmol) in t-butylbenzene (100 mL) at-78deg.C, followed by a reaction at 60℃for 4 hours. After the reaction was completed, the temperature was lowered to-78℃and boron tribromide (15 mmol) was slowly added thereto, followed by stirring at room temperature for 1 hour. N, N-diisopropylethylamine (20 mmol) was added at room temperature and the reaction was stopped after a further 6 hours at 145 ℃. And (3) spin-drying the solvent in vacuum and performing column chromatography purification to obtain a target intermediate d-2.
MALDI-TOF: m/z: C43H26BClN2:616.19, test value 616.17.
Compound elemental analysis results: calculated C,83.71; h,4.25; b,1.75; cl,5.75; n,4.54; test value: c,83.70; h,4.26; b,1.75; cl,5.75; n,4.54.
Synthesis of Compound RH03
In a round-bottomed flask, intermediate d-2 (4 mmol), compound e-1 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH03.
MALDI-TOF: m/z: C58H36BN5:813.31, test value 813.25.
Compound elemental analysis results: calculated value C,85.61; h,4.46; b,1.33; n,8.61; test value: c,85.60; h,4.47; b,1.32; n,8.62.
Example 5: synthesis of Compound RH34
In a round-bottomed flask, intermediate d-2 (4 mmol), compound e-4 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH34.
MALDI-TOF: m/z: C64H40BN5:889.34, test value 889.30.
Compound elemental analysis results: calculated value C,86.38; h,4.53; b,1.21; n,7.87; test value: c,86.37; h,4.54; b,1.21; n,7.87.
Example 6: synthesis of Compound RH50
In a round-bottomed flask, intermediate d-2 (4 mmol), compound e-5 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH50.
MALDI-TOF: m/z: C63H39BN4:862.33, test value 862.30.
Compound elemental analysis results: calculated C,87.70; h,4.56; b,1.25; n,6.49; test value: c,87.69; h,4.56; b,1.25; n,6.50.
Example 7:
synthesis of intermediate d-3
In a nitrogen atmosphere, 1, 2-dichlorobenzene as a reaction solvent was added, a reaction intermediate a-3 (2 mmol), a reaction intermediate b-1 (2.2 mmol), potassium carbonate (7 mmol), cuI (0.5 mmol) as a catalyst and 18-crown-6 (0.5 mmol) as a ligand were added in sequence, and the mixture was heated to 100℃and reacted for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic phase was collected by suction filtration, followed by addition of dichloromethane/H 2 O was extracted, and the collected organic phase was extracted with anhydrous Na 2 SO 4 Drying, suction filtering, collecting filtrate, spin-removing solvent, and purifying by column chromatography to obtain intermediate c-3.
A solution of t-butyllithium in pentane (8.0 mL,1.70M,13.5 mmol) was slowly added to a solution of c-3 (2.40 mmol) in t-butylbenzene (100 mL) at-78deg.C, followed by a reaction at 60℃for 4 hours. After the reaction was completed, the temperature was lowered to-78℃and boron tribromide (15 mmol) was slowly added thereto, followed by stirring at room temperature for 1 hour. N, N-diisopropylethylamine (20 mmol) was added at room temperature and the reaction was stopped after a further 6 hours at 145 ℃. And (3) spin-drying the solvent in vacuum and performing column chromatography purification to obtain a target intermediate d-3.
MALDI-TOF: m/z: C43H26BFN2:600.22, test value was 600.20.
Compound elemental analysis results: calculated value C,86.01; h,4.36; b,1.80; f,3.16; n,4.67; test value: c,86.01; h,4.36; b,1.80; f,3.16; n,4.67.
Synthesis of Compound RH17
In a round-bottomed flask, intermediate d-2 (4 mmol), compound e-2 (6 mmol) and Pd (PPh) were added 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH17.
MALDI-TOF: m/z: C64H40BN5:889.34, test value 889.30.
Compound elemental analysis results: calculated value C,86.38; h,4.53; b,1.21; n,7.87; test value: c,86.39; h,4.53; b,1.20; n,7.87.
Example 8: synthesis of Compound RH18
In a round-bottomed flask, the intermediate d-3 (4 mmol), compound e-3 (6 mmol) and Pd (PPh) 3 ) 4 (0.3 mmol) was added to a mixture of toluene (180 mL)/ethanol (150 mL) and an aqueous solution of potassium carbonate (15 mmol) (10 mL), and the mixture was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give the desired product RH18.
MALDI-TOF: m/z: C64H40BN5:889.34, test value 889.31.
Compound elemental analysis results: calculated value C,86.38; h,4.53; b,1.21; n,7.87; test value: c,86.39; h,4.54; b,1.20; n,7.86.
Device example 1
The present embodiment provides an organic light emitting device, as shown in fig. 1, including: the substrate 1, the ITO anode 2, the first hole transport layer 3, the second hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the first electron transport layer 7, the second electron transport layer 8, the cathode 9 (magnesium silver electrode, magnesium silver mass ratio is 9:1) and the cap layer (CPL) 10, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the electron blocking layer 5 is 30nm, the thickness of the light emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 30nm, the thickness of the second electron transport layer 8 is 5nm, the thickness of the magnesium silver electrode 9 is 15nm and the thickness of the cap layer (CPL) 10 is 100nm.
The OLED device was prepared as follows:
1) Cutting the glass substrate 1 into 50mm×50mm×0.7mm sizes, respectively sonicating in isopropyl alcohol and deionized water for 30 minutes, and then exposing to ozone for about 10 minutes for cleaning; mounting the obtained glass substrate with the ITO anode 2 onto a vacuum deposition apparatus;
2) Evaporating a hole buffer layer material HT-1:HAT-CN on an ITO anode 2 in a vacuum evaporation mode, wherein the mass ratio of the compound HT1 to the HAT-CN is 98:2 to obtain a layer with the thickness of 10nm, and the layer is used as a first hole transport layer 3;
3) Vacuum evaporating a material HT-1 of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with the thickness of 95nm, wherein the layer is used as the second hole transport layer 4;
4) Evaporating a material Prime-1 on the second hole transport layer 4 to obtain a layer with the thickness of 30nm, wherein the layer is used as an electron blocking layer 5;
5) A light-emitting layer 6 was co-deposited on the electron blocking layer 5 using the organic compound RH02 provided in example 1 of the present invention as a host material, ir (piq) 2 (acac) as doping materials, organic compounds RH02 and Ir (piq) 2 (acac) a mass ratio of 19:1, a thickness of 30nm; the method comprises the steps of carrying out a first treatment on the surface of the
6) Vacuum evaporating a first electron transport layer 7 compound ET-1 on the light-emitting layer 6 to obtain a first electron transport layer 7 with the thickness of 30nm;
7) Vacuum evaporating material LiF of the second electron transport layer 8 on the first electron transport layer 7 to obtain a second electron transport layer 8 with a thickness of 5 nm;
8) Vacuum evaporating magnesium and silver on the second electron transport layer 8 to obtain a cathode 9 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9:1;
9) The high refractive index hole-type material CPL-1 was vacuum deposited on the cathode 9 to a thickness of 100nm, and used as a cathode coating layer (capping layer or CPL) 10.
The materials mentioned in the above steps HAT-CN, HT-1, prime-1, ir (piq) 2 The structural formulas of (acac), ET-1 and CPL-1 are respectively shown as follows:
device example 2
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH03 provided by the present invention; the other preparation steps were identical.
Device example 3
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH17 provided by the present invention; the other preparation steps were identical.
Device example 4
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH18 provided by the present invention; the other preparation steps were identical.
Device example 5
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH33 provided by the present invention; the other preparation steps were identical.
Device example 6
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH34 provided by the present invention; the other preparation steps were identical.
Device example 7
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH49 provided by the present invention; the other preparation steps were identical.
Device example 8
The present device example differs from device example 1 only in that the organic compound RH02 in step (5) is replaced with an equivalent amount of the organic compound RH50 provided by the present invention; the other preparation steps were identical.
Device comparative example 1
The device comparative example differs from device example 1 only in that the organic compound RH02 in step (5) was treated with an equivalent amount of the comparative compound M1Replacement; the other preparation steps were identical.
Device comparative example 2
The device comparative example differs from device example 1 only in that the organic compound RH02 in step (5) was treated with an equivalent amount of the comparative compound M2Replacement; the other preparation steps were identical.
Performance evaluation of OLED device:
testing the currents of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain the current densities of the OLED device under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device under different voltages, the OLED device with the same current density (10 mA/cm 2 ) Is the luminance 1Cd/m 2 A lower turn-on voltage; lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance 2 Under test conditions; the specific data are shown in table 1.
Table 1 OLED device performance test results
As can be seen from the data of table 1, the electroluminescent device using the organic compound of the present invention has a lower on-luminance voltage than the device of comparative example 1, and the on-luminance voltage is reduced by about 6.2% (as in table 1 above, the on-luminance voltage is obtained by taking the on-luminance voltage of device comparative example 2 as 100%, the relative on-luminance voltage) so that the power consumption of the device can be effectively reduced; devices using the organic compounds of the present invention have higher current efficiencies, about 7.9% to 9.8% improvement over comparative example 2 (the current efficiencies in table 1 above are relative current efficiencies obtained by taking the current efficiencies of device comparative example 2 as 100%); devices using the organic compounds of the present invention have longer lifetimes, which are about 8.0% to 9.8% longer than those of comparative example 1 (LT 95 in table 1 above is relative LT95 obtained by taking LT95 of device comparative example 2 as 100%).
The applicant states that the organic compounds of the present invention and their use are illustrated by the above examples, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (7)
1. An organic compound, characterized in that the organic compound is any one of the following compounds:
2. an organic electroluminescent material, characterized in that it comprises the organic compound according to claim 1.
3. A light-emitting layer material, characterized in that the light-emitting layer material comprises the organic compound according to claim 1.
4. An OLED device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound of claim 1.
5. The OLED device of claim 4, wherein the organic thin film layer includes a light-emitting layer including a host material including the organic compound of claim 1 and a doping material.
6. A display panel comprising the OLED device of claim 4 or 5.
7. An organic light-emitting display device, characterized in that the organic light-emitting display device comprises the display panel according to claim 6.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112106218A (en) * | 2018-08-20 | 2020-12-18 | 株式会社Lg化学 | Organic light emitting diode |
| CN112204762A (en) * | 2018-10-12 | 2021-01-08 | 株式会社Lg化学 | Organic light emitting device |
| CN112250701A (en) * | 2020-05-08 | 2021-01-22 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
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| KR102112411B1 (en) * | 2017-09-28 | 2020-05-18 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112106218A (en) * | 2018-08-20 | 2020-12-18 | 株式会社Lg化学 | Organic light emitting diode |
| CN112204762A (en) * | 2018-10-12 | 2021-01-08 | 株式会社Lg化学 | Organic light emitting device |
| CN112250701A (en) * | 2020-05-08 | 2021-01-22 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
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