CN114105873A - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
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- CN114105873A CN114105873A CN202111376615.0A CN202111376615A CN114105873A CN 114105873 A CN114105873 A CN 114105873A CN 202111376615 A CN202111376615 A CN 202111376615A CN 114105873 A CN114105873 A CN 114105873A
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- substituted
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- organic compound
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 43
- 239000010409 thin film Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 3
- -1 dibenzofuranyl group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 150000001616 biphenylenes Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 150000003220 pyrenes Chemical class 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000007738 vacuum evaporation Methods 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 2
- 238000005191 phase separation Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000000605 extraction 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000008020 evaporation Effects 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000009825 accumulation Methods 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
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000008033 biological extinction Effects 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research 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
- 238000010189 synthetic method Methods 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
- 238000001771 vacuum 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
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- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- 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
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
本发明提供一种有机化合物及其应用,本发明提供的有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。本发明的有机化合物适用于OLED器件的有机覆盖层,使得OLED器件具有较高的电流效率,较低的驱动电压。
Description
技术领域
本发明属于有机电致发光材料领域,涉及一种有机化合物及其应用。
背景技术
OLED经过几十年的发展,已经取得了长足的进步。虽然其内量子效率已经接近100%,但外量子效率却仅有大约20%左右。大部分的光由于基板模式损失、表面等离子损失与波导效应等因素被限制在发光器件内部,导致了大量能量损失。顶发射器件中,通过在半透明金属电极Al上蒸镀一层有机覆盖层(Capping Layer,CPL),调节光学干涉距离,抑制外光反射,抑制表面等离子体能移动引起的消光,从而提高光的取出效率,提升发光效率。
现有的材料为了使分子的密度增加,并达到高的热稳定性,分子结构设计的很大并且疏松,分子间不能达到紧密的堆积,从而在蒸镀时造成分子凝胶孔洞太多,覆盖紧密性不良,且折射率低,现有的材料折射率一般1.9以下,并不能满足高折射率的要求。
因此,在本领域,对于有机覆盖层材料的进一步开发是研究的重点。
发明内容
针对现有技术的不足,本发明的目的在于提供一种有机化合物及其应用。
为达此目的,本发明采用以下技术方案:
本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如下式I所示结构:
其中,Ar1-Ar3独立地选自C6~C18亚芳基或者C5~C18的亚杂芳基;
在本发明中,所述C6~C18各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18等。
所述C5~C18各自独立地可以为C5、C7、C9、C10、C12、C13、C14、C15、C16、C18等。
所述C6~C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3~C30各自独立地可以为C4、C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物以含有氮杂环的芳香胺为中心骨架,利用这样的材料可以提高顶发射有机光电装置的光取出效率和发光效率(对蓝光像素做最有效),缓解OLED器件发光的角度依存性(对红/绿光像素最有效),同时有效阻挡外部环境中的水和氧,保护OLED显示面板不受水氧侵蚀。
本发明的目的之二在于提供一种电致发光材料,所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种有机覆盖层材料,其特征在于,所述有机覆盖层材料包括如目的之一所述的有机化合物。
本发明的目的之四在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之二所述的有机电致发光材料。
本发明的目的之五在于提供一种显示面板,所述显示面板包括如目的之四所述的OLED器件。
本发明的目的之六在于提供一种有机发光显示装置,所述有机发光显示装置包括如目的之五所述的显示面板。
相对于现有技术,本发明具有以下有益效果:
本发明提供的有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。本发明的有机化合物适用于OLED器件的有机覆盖层,使得OLED器件具有较高的电流效率和较低的驱动电压。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如下式I所示结构:
其中,Ar1-Ar3独立地选自C6~C18亚芳基或者C5~C18的亚杂芳基;
在本发明中,所述C6~C18各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18等。
所述C5~C18各自独立地可以为C5、C7、C9、C10、C12、C13、C14、C15、C16、C18等。
所述C6~C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3~C30各自独立地可以为C4、C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物以含有氮杂环的芳香胺为中心骨架,利用这样的材料可以提高顶发射有机光电装置的光取出效率和发光效率(对蓝光像素做最有效),缓解OLED器件发光的角度依存性(对红/绿光像素最有效),同时有效阻挡外部环境中的水和氧,保护OLED显示面板不受水氧侵蚀。
在一个实施方式中,Ar1-Ar3独立地选自取代的或未取代的亚苯基、取代的或未取代的亚联苯基或取代的或未取代的亚萘基。
在一个实施方式中,A1、A2和A3独立地选自取代的或未取代的苯基基团、取代的或未取代的联苯基基团、取代的或未取代的萘基基团、取代的或未取代的菲基基团、取代的或未取代的三亚苯基基团、取代的或未取代的芴基基团、取代的或未取代的咔唑基基团、取代的或未取代的二苯并呋喃基基团、取代的或未取代的二苯并噻吩基基团、取代的或未取代的嘧啶基基团、取代的或未取代的三嗪基基团、取代的或未取代的蒽、取代的或未取代的芘、取代或未取代的B基团。
在一个实施方式中,所述有机化合物为具有如下所示结构的化合物:
其中Ar1-Ar3的限定范围与权利要求1中相同,A1选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种。
在一个实施方式中,所述有机化合物为具有如下所示结构的化合物:
其中Ar1-Ar3的限定范围与权利要求1中相同。
在一个实施方式中,所述有机化合物为如下化合物中的任意一种:
本发明的目的之二在于提供一种电致发光材料,所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种有机覆盖层材料,其特征在于,所述有机覆盖层材料包括如目的之一所述的有机化合物。
本发明的目的之四在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之二所述的有机电致发光材料。
在一个实施方式中,所述OLED器件还包括有机覆盖层,所述有机覆盖层的材料包括如目的之一所述的有机化合物。
本发明提供的OLED器件中,阳极材料可以为金属、金属氧化物或导电性聚合物;其中,所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金,所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等,所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合,还包括已知的适合做阳极的材料。
所述OLED器件中,阴极材料可以为金属或多层金属材料;其中,所述金属包括铝、镁、银、铟、锡、钛等及它们的合金,所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合,还包括已知的适合做阴极的材料。
所述OLED器件中,有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)或电子注入层(EIL)中的任意一种或至少两种的组合。
所述OLED器件可以通过以下方法制备:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。其中,形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之五在于提供一种显示面板,所述显示面板包括如目的之四所述的OLED器件。
本发明的目的之六在于提供一种有机发光显示装置,所述有机发光显示装置包括如目的之五所述的显示面板。
本发明提供的化合物的制备方法属于现有技术,本领域技术人员可以根据常规技术知识选择具体的合成方法,本发明仅示例性的提供合成路径,但不限于以下合成路径。
本发明提供的式Ⅰ化合物的代表合成路径如下:
以下示例性地列举几种本发明所述有机化合物的制备实施例:
制备实施例1
化合物P1的合成:
具体制备方法具体包括以下步骤:
(1)将P1-1(0.5mmol)、P1-2(1.1mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.04mol)、Ligand(0.04mol,以下制备实施例中Ligand均指该化合物)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在110℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P1。
测试目标产物P1的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C42H27N7,计算值为629.2,测试值为629.2。
元素分析:理论值C,80.11;H,4.32;N,15.57;测试值C,80.11;H,4.31;N,15.58。
制备实施例2
化合物P3的合成:
具体制备方法具体包括以下步骤:
将P3-1(0.5mmol)、P3-2(1.1mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.04mol)、Ligand(0.04mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在110℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P3。
测试目标产物P3的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C45H30N4,计算值为626.3,测试值为626.2。
元素分析:理论值C,86.24;H,4.82;N,8.94;测试值C,86.23;H,4.83;N,8.94。
制备实施例3
化合物P9的合成:
具体制备方法具体包括以下步骤:
将P9-1(0.5mmol)、P9-2(1.1mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.04mol)、Ligand(0.04mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在110℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P9。
测试目标产物P9的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C45H30N4,计算值为627.2,测试值为627.1。
元素分析:理论值C,84.19;H,4.66;N,11.16;测试值C,84.19;H,4.67;N,11.16。
制备实施例4
化合物P20的合成:
具体制备方法具体包括以下步骤:
将P20-1(0.5mmol)、P20-2(1.1mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.04mol)、Ligand(0.04mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在110℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P20。
测试目标产物P20的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C47H30N4O,计算值为666.2,测试值为666.1。
元素分析:理论值C,84.66;H,4.54;N,8.40;测试值C,84.66;H,4.55;N,8.40。
制备实施例5
化合物P52的合成:
具体制备方法具体包括以下步骤:
将P52-1(0.5mmol)、P52-2(0.5mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.02mol)加入THF 3mL溶液中混合,放入50mL的烧瓶中,在78℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P52-3。
将P52-3(0.5mmol)、P52-4(0.6mmol)、KO(t-Bu)(1.0mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.02mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在110℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到产物P52。
测试目标产物P52的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C49H30N4O2,计算值为706.2,测试值为706.1。
元素分析:理论值C,83.27;H,4.28;N,7.93;测试值C,83.27;H,4.28;N,7.93。
具体实施方式中所使用的本发明化合物的制备方法均与上述方法相似,不一一赘述,仅提供其表征结果,质谱分析与元素分析结果如表1所示。
表1
性能测试一材料折射率表征
通过椭偏仪测试化合物在460nm、530nm和620nm波长处的折射率。
测试结果如表2所示。
表2
以下列举几种本发明所述有机化合物应用于OLED器件中的应用例:
器件实施例1
本实施例提供一种有机电致发光器件,具体制备步骤如下:
1)将带有氧化铟锡(ITO)阳极层2(厚度为15nm)的玻璃基板切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30分钟,然后暴露在臭氧下约10min来进行清洁,将清洗后的基板1安装到真空沉积设备上;
2)在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料化合物b和p掺杂材料化合物a,掺杂比例为3%(质量比);厚度为5nm,作为空穴注入层3;
3)在空穴注入层3上真空蒸镀空穴传输层材料化合物b,厚度为100nm作为第一空穴传输层4;
4)在第一空穴传输层4上真空蒸镀空穴传输型材料化合物c,厚度为5nm作为第二空穴传输层5;
5)第二空穴传输层5上真空蒸镀一层发光层6,其中,化合物d作为主体材料,化合物e作为掺杂材料,掺杂比例为3%(质量比),厚度为30nm;
6)在发光层6上真空蒸镀电子传输型材料化合物f,厚度为30nm,作为第一电子传输层7;
7)第一电子传输层7上真空蒸镀电子传输材料化合物g和n掺杂材料化合物h,掺杂质量比例为1:1;厚度为5nm,作为第二电子传输层8;
8)在第二电子传输层8上真空蒸镀镁银电极,其中,Mg:Ag为9:1,厚度为10nm,作为阴极9;
9)在阴极9上真空蒸镀本发明的化合物P1,厚度为100nm,作为盖帽层10使用。
上述步骤中使用的化合物结构如下:
器件实施例2-22
本应用例与应用例1的区别仅在于,将其中的有机化合物P1用等量的如表3所示实施例2-22对应的有机化合物替换,其他制备步骤均相同。
对比例1
本对比例与应用例1的区别在于,将其中的有机化合物1用等量的化合物A替换,其他制备步骤均相同。
对比例2
本对比例与应用例1的区别在于,将其中的有机化合物1用等量的化合物B替换,其他制备步骤均相同。
对比例3
本对比例与应用例1的区别在于,将其中的有机化合物1用等量的化合物C替换,其他制备步骤均相同。
OLED器件的性能评价:
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度下(10mA/cm2)的启亮电压和电流效率(CE,Cd/A),Von为亮度1Cd/m2下的启亮电压;通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);具体数据如表3所示。
表3
由表3数据可以看出,本申请所述有机化合物作为OLED器件的有机覆盖层材料,可以使得器件具有较高的电流效率(6.8cd/A以上),较低的驱动电压(3.55V以下)。
申请人声明,本发明通过上述实施例来说明本发明的有机化合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (15)
2.根据权利要求1所述的有机化合物,其特征在于,Ar1-Ar3独立地选自取代的或未取代的亚苯基、取代的或未取代的亚联苯基或取代的或未取代的亚萘基。
3.根据权利要求1所述的有机化合物,其特征在于,A1、A2和A3独立地选自取代的或未取代的苯基基团、取代的或未取代的联苯基基团、取代的或未取代的萘基基团、取代的或未取代的菲基基团、取代的或未取代的三亚苯基基团、取代的或未取代的芴基基团、取代的或未取代的咔唑基基团、取代的或未取代的二苯并呋喃基基团、取代的或未取代的二苯并噻吩基基团、取代的或未取代的嘧啶基基团、取代的或未取代的三嗪基基团、取代的或未取代的蒽、取代的或未取代的芘、取代或未取代的B基团。
9.一种有机电致发光材料,其特征在于,所述有机电致发光材料包括如权利要求1-8中任一项所述的有机化合物。
10.一种有机覆盖层材料,其特征在于,所述有机覆盖层材料包括如权利要求1-8中任一项所述的有机化合物。
11.一种OLED器件,其特征在于,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如权利要求9所述的有机电致发光材料。
12.根据权利要求10所述的OLED器件,其特征在于,所述OLED器件还包括有机覆盖层,所述有机覆盖层的材料包括如权利要求1-8中任一项所述的有机化合物。
13.一种显示面板,其特征在于,所述显示面板包括如权利要求11或12所述的OLED器件。
14.一种有机发光显示装置,其特征在于,包括如权利要求13所述的显示面板。
15.一种电子设备,其特征在于,所述电子设备包括如权利要求13所述的显示面板。
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