CN116120265A - 一种含芳胺基团的发光辅助材料及其制备方法与应用 - Google Patents
一种含芳胺基团的发光辅助材料及其制备方法与应用 Download PDFInfo
- Publication number
- CN116120265A CN116120265A CN202111341735.7A CN202111341735A CN116120265A CN 116120265 A CN116120265 A CN 116120265A CN 202111341735 A CN202111341735 A CN 202111341735A CN 116120265 A CN116120265 A CN 116120265A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- auxiliary material
- group
- aromatic amine
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 59
- 150000004982 aromatic amines Chemical group 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 14
- 125000005264 aryl amine group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
- 238000005406 washing Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 15
- 239000000376 reactant Substances 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- -1 methoxy, phenyl Chemical group 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 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 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 3
- 238000000746 purification Methods 0.000 claims 3
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000005457 optimization Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical compound C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 1
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/14—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
技术领域
本发明涉及有机发光材料技术领域,更具体的说是涉及一种含芳胺基团的发光辅助材料及其制备方法与应用。
背景技术
现有技术中有机电致发光(OLED)器件技术既可以用来制造显示产品,也可以用于制作照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。利用有机发光现象的有机电气元件通常具有阳极、阴极及它们之间包括有机物层的结构,为了提高有机电气元件的效率和稳定性,有机物层通常由各种不同物质构成的多层结构组成。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类,分别为电荷注入传输材料和发光材料;进一步,还可将电荷注入传输材料分为电子注入传输材料、电子阻挡材料、空穴注入传输材料和空穴阻挡材料,还可以将发光材料分为主体发光材料和掺杂材料。
空穴传输层(HTL)负责调节空穴的注入速度和注入量,在所述OLED中,酞菁铜(CuPc)、4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N’-二苯基-N,N’-双(3-甲基苯基)-(1,1’-联苯基)-4,4’-二胺(TPD)、4,4’,4”-三(3-甲基苯基苯基氨基)三苯胺(MTDATA)等常用作在空穴传输区域中包含的化合物。然而,使用这些材料的OLED在量子效率和使用寿命方面存在问题,这是因为当在高电流下驱动OLED时,在阳极与空穴注入层之间出现热应力,并且所述热应力显著降低装置的使用寿命。此外,由于空穴传输区域中使用的有机材料具有非常高的空穴迁移率,所以可能破坏空穴-电子电荷平衡并且量子效率(cd/A)可能降低。
为了解决上述问题,现有技术中通常会在空穴输送层和发光层之间加入发光辅助层(即设置多层空穴输送层)提高器件寿命和效率,发光辅助层能够起到减少空穴传输层与发光层之间的势垒,降低有机电致发光器件的驱动电压的作用,进一步增加空穴的利用率,从而改善器件的发光效率和寿命,降低驱动电压,但是现有能够形成发光辅助层的功能材料较少,特别是OLED的寿命和发光效率提升不明显,玻璃化温度较低等问题,因此如何提供一种寿命长效率高的发光辅助材料是本领域技术人员亟需解决的问题。
发明内容
有鉴于此,本发明提供了一种含芳胺基团的发光辅助材料及其制备方法与应用,本发明材料具有较高的玻璃化温度,通过器件结构优化,可有效提升OLED器件的寿命和发光效率的同时降低驱动电压。
为了达到上述目的,本发明采用如下技术方案:
一种含芳胺基团的发光辅助材料,所述发光辅助材料的结构通式如式I所示:
其中,环A为经取代或未经取代的C6~C20芳基;
X为O、S、-C(R1)(R2)-和NR3中的任意一种;R1-R3各自独立的表示经取代或未经取代的C1~C12烷基、经取代或未经取代的C6~C18芳基和经取代或未经取代的3元~30元杂芳基中的任意一种;
R为经取代或未经取代的C1~C10烷基、经取代或未经取代的C6~C30芳基和经取代或未经取代的3元~30元杂芳基中的任意一种;
Ar1和Ar2为经取代或未经取代的C3~C20环烷基、经取代或未经取代的3元~30元杂环烷基、经取代或未经取代的C6~C30芳基、经取代或未经取代的3元~20元杂芳基、经取代或未经取代的C10~C30稠环基和取代或未取代的C5-C30螺环基中的至少一种。
优选地,所述环A为联苯基、苯基和萘基中的任意一种。
优选地,所述R1-R3为甲基、乙基、苯基、联苯基、甲基苯和萘基中的任意一种。
优选地,所述R为氢、甲基、乙基、叔丁基、甲基苯、甲氧基、苯基、萘基、联苯基、菲基、咔唑基、芴基、二甲基芴、三联苯基、苯并呋喃、苯并噻吩和吡啶基中的任意一种。
优选地,所述杂环烷基和所述杂芳基中杂原子为N、O、S、Si、P和Se等中的至少一种。
优选地,所述发光辅助材料通式I的结构为:
优选地,式1-a、所述式1-b和所述式1-c的结构为:
优选地,X为O或者S;R为氢、甲基、乙基、叔丁基、甲基苯、甲氧基、苯基、萘基、联苯基、菲基、咔唑基、二甲基芴、三联苯基和吡啶基中的任意一种。
优选地,所述Ar1与Ar2在任意可连接位置与N进行连接,所述Ar1和所述Ar2独立的选自以下基团中的至少一种:
优选地,所述取代基独立的选自卤素、氘和氰基中的至少一种。
进一步地,在上述技术方案中“取代”意指与化合物的碳原子键合的氢原子变成另外的取代基,并且取代的位置没有限制,只要该位置为氢原子被取代的位置(即,取代基可以取代的位置)即可,并且当存在两个或更多个取代基取代时,两个或更多个取代基可以彼此相同或不同。
需要说明的是:取代或未取代的烷基可以是甲基、乙基、异丙基、正丙基、叔丁基等未取代烷基,也可以是三氯甲基、氰基取代异丙基等取代烷基。取代或未取代的芳基可以是苯基、奈基、联苯等未取代芳基,也可以是苄基等取代芳基。取代或未取代的环烷基可以是环丙烷基、环己烷基等未取代环烷基,也可是含有卤素、氰基、羰基等基团的取代环烷基。取代或未取代的烷氧基可以是甲氧基、乙氧基和丙氧基等未取代的烷氧基,也可以是含有卤素、氰基、羰基等基团的取代烷氧基。取代或未取代的烷胺基可以是甲基氨基、乙基氨基、丙基氨基、异丙基氨基等未取代的烷胺基,也可以是卤素,氰基,硝基等取代的烷胺基。取代或未取代的烯烃基可以是乙烯基、丙烯基等未取代的烯烃基,也可以是含有卤素、氰基、羰基等基团的取代烯烃基。取代或未取代的炔烃基可以是乙炔基、丙炔基等未取代的炔烃基,也可以是含有卤素、氰基、羰基等基团的取代炔烃基。取代或未取代的杂环基可以是呋喃基、噻唑基、吡唑基、哌嗪基、吡啶基、嘧啶基、吡咯基等未取代的杂环基,也可以是卤素、氰基、羰基等基团取代的杂环基。取代或未取代的稠环基可以是萘基、蒽基、菲基、芘基、苝基、芴基、苯并芴基、三亚苯基未取代的稠环基,也可以是卤素、氰基、羰基等基团取代的稠环基。
优选地,所述发光辅助材料选自以下结构中的任意一种:
以上仅列举了一些具体的结构式,但本发明请求保护的系列发光辅助材料不局限上述分子结构,凡是本发明公开的基团及其取代位置的简单变换就可以得到其他具体的分子结构,在此不再一一赘述,且其均应落入本发明申请的保护范围。
优选地,上述所述种含芳胺基团的发光辅助材料的制备方法,具体包括以下步骤:
(1)Ar1与Ar2不相同:
1)N2保护下,将中间体A-1(1.0eq)、反应物B-1(1-1.2eq)、四(三苯基膦)钯(0.01-0.02eq)和碳酸钾(2.1-2.3eq)依次加入到甲苯、乙醇和水(体积比为2-4:1:1)的混合溶剂中,升温至100-120℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥得滤饼,将所述滤饼置于1,4-二氧六环中重结晶,得到化合物中间体C-1;
2)将所述中间体C-1(1.0eq)和反应物D-1(1.0-1.2eq)溶于甲苯,在氮气氛围下加入Pd2(dba)3(0.01eq)、P(t-Bu)3(0.02-0.05eq)和t-BuONa(2.0-2.5eq)后,使反应温度缓慢升温到110℃,并且搅拌混合物反应10h,反应结束后使用硅藻土趁热抽滤,除去盐和催化剂,得到滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,然后用乙酸乙酯萃取水相,合并有机相,接着使用硫酸镁干燥合并后的有机相,并且使用旋转式蒸发器去除溶剂,最后以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物中间体E-1;
3)将所述中间体E-1(1.0eq)和反应物F-1(1.0-1.2eq)溶于甲苯后,在氮气氛围下加入Pd2(dba)3(0.01eq)、P(t-Bu)3(0.02-0.05eq)和t-BuONa(2.0-2.5eq)后,使反应温度缓慢升温到110℃,并且搅拌混合物反应10h,反应结束后使用硅藻土趁热抽滤,除去盐和催化剂,得到滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,然后用乙酸乙酯萃取水相,合并有机相,接着使用硫酸镁干燥合并后的有机相,并且使用旋转式蒸发器去除溶剂,最后以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物通式1;其中,反应合成路线如下:
(2)Ar1与Ar2相同:
1)N2保护下,将中间体A-1(1.0eq)、反应物B-1(1-1.2eq)、四(三苯基膦)钯(0.01-0.02eq)和碳酸钾(2.1-2.3eq)依次加入到甲苯、乙醇和水(体积比为2-4:1:1)的混合溶剂中,升温至100-120℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥得滤饼,将所述滤饼置于1,4-二氧六环中重结晶,得到化合物中间体C-1;
2)将所述中间体C-1(1.0eq)和反应物D-1(1.0-1.2eq)溶于甲苯,在氮气氛围下加入Pd2(dba)3(0.01eq)、P(t-Bu)3(0.02-0.05eq)和t-BuONa(2.0-2.5eq)后,使反应温度缓慢升温到110℃,并且搅拌混合物反应10h,反应结束后使用硅藻土趁热抽滤,除去盐和催化剂,得到滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,然后用乙酸乙酯萃取水相,合并有机相,接着使用硫酸镁干燥合并后的有机相,并且使用旋转式蒸发器去除溶剂,最后以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物通式1;其中,反应合成路线如下:
其中,R、X、Ar1、Ar2、环A如上述通式1中所定义,Ha l 1、Ha l2和Ha l3为氯、溴和碘中的任意一种。
上述所述一种含芳胺基团的发光辅助材料用于制备有机电致发光器件的应用。
优选地,所述有机电致发光器件包括:第一电极、有机物层、第二电极;其中,所述有机物层包含上述所述含芳胺基团的发光辅助材料。
优选地,所述有机物层包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种,且至少其中一层包括所述含芳胺基团的发光辅助材料;且本发明公开制备的含芳胺基团的发光辅助材料可以是单一形态或与其它物质混合存在于有机物层中;在上述有机发光元件包含多个有机物层的情况下,上述有机物层可以由相同物质或不同物质形成。
优选地,所述有机物层包括发光层,所述发光层中包括主体材料和所述含芳胺基团的发光辅助材料。
优选地,所述主体材料与所述含芳胺基团的发光辅助材料的质量比为90:10~99.5:0.5。
优选地,在制造有机发光元件时,可以利用真空蒸镀法,也可以利用溶液涂布法来形成有机物层。其中,所谓溶液涂布法是指,旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但并非仅限于此。
优选地,本发明的有机发光元件根据所使用的材料,可以为顶部发光型、底部发光型或双向发光型。
本发明所述的器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
经由上述的技术方案可知,与现有技术相比,本发明的有益效果如下
(1)本发明以苯并萘并呋喃或苯并萘并噻吩骨架通过联苯,三联苯或苯基萘与芳胺类基团进行连接,得到具有优异性能的用于蓝光发光辅助层的有机电致发光化合物,制得的器件具有高发光效率、驱动电压低和使用寿命长等特点。
(2)本发明化合物中的芳胺基团使得其有很强的空穴传输能力,单三芳胺结构能够降低分子的结晶性,降低分子的平面性,阻止分子在平面上移动的同时,高的空穴传输速率能够降低器件的驱动电压,提高有机电致发光器件的效率,寿命。
(3)本发明利用苯并萘并呋喃或苯并萘并噻吩具有刚性平面结构,并通过具有桥联π基团的联苯,三联苯或苯基萘进一步降低分子的对称性,增加分子的构象异构体,使化合物不易结晶,不易聚集,具有良好的成膜性和热稳定性,具有较高的玻璃化温度;两个功能基团之间的桥联π基团使用联苯基,特别是3,5-联苯基时,具有更好的效率和长使用寿命。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据提供的附图获得其他的附图。
图1为本发明实施例化合物1的核磁共振氢谱;
图2为本发明实施例化合物40的核磁共振氢谱;
图3为本发明实施例化合物3的核磁共振氢谱;
图4为本发明实施例化合物9的核磁共振氢谱。
具体实施方式
下面将对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
制备化合物1,具体步骤如下:
1):在氮气保护体系下,称取中间体A-1(50mmol)、反应物B-1(55mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(105mmol)加入甲苯(300ml)、乙醇(100ml和水(100ml)的混合溶液中,升温至100℃,反应8h,反应停止后体系冷却至室温,溶液内有沉淀析出,将沉淀物减压过滤,过滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥滤饼,然后置于1,4-二氧六环中重结晶,得到中间体C-1所示化合物(17.4g,Ms:405.01,产率:86%);
2):在反应容器中加入中间体C-1(40mmol)和反应物D-1(88mmol)溶于400ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.6mmol)、P(t-Bu)3(1.2mmol)、t-BuONa(120mmol),使反应温度缓慢升温到110℃后,搅拌混合物反应10h,反应结束后,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相后与有机像合并,接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂,以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物1(22.36g,产率:81%);
HPLC纯度:>99.7%。
质谱测试:理论值为689.86;测试值为690.19;
元素分析:
理论值:C,90.54;H,5.11;N,2.03;O,2.32
测试值:C,90.38;H,5.26;N,2.09;O,2.47
核磁共振氢谱:如图1所示;
具体的反应原理如下:
实施例2
制备化合物40,具体步骤如下:
1):C-40反应步骤与实施例1:C-1反应步骤相同(17.2g,产率:85%);
2):在反应容器中加入中间体C-40(40mmol)和反应物D-40(48mmol)溶于甲苯后,在氮气氛围下加入Pd2(dba)3(0.4mmol)、P(t-Bu)3(0.8mmol)和t-BuONa(80mmol),添加后缓慢升温到110℃,并且搅拌混合物反应10h;反应结束后,使用硅藻土趁热抽滤反应液,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相后与有机相合并,接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂;最后以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物中间体E-40(20.0g,Ms:587.67,产率:85%);
3)在反应容器中加入中间体E-40(30mmol)和反应物F-40(36mmol)溶于甲苯之后,在氮气氛围下加入Pd2(dba)3(0.3mmol)、P(t-Bu)3(0.6mmol)和t-BuONa(60mmol),添加后,缓慢升温到110℃,并且搅拌混合物反应10h,反应结束后,使用硅藻土趁热抽滤反应液,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相后与有机相合并,接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂;最后以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得化合物40(19.9g,产率:80%);
HPLC纯度:≥99.8%。
质谱测试:理论值为830;测试值为830.23。
元素分析:
理论值:C,89.72;H,4.74;N,1.69;O,3.86
测试值:C,89.66;H,4.90;N,1.56;O,3.98
核磁共振氢谱:如图2所示;
具体的反应原理如下:
因其它化合物的制备方法均与上述所列举的2个实施例相同,所以在此不再穷举,本发明又选取121个化合物作为实施例,其质谱、分子式及产率如表1所示:
表1其它化合物的分子式、质谱及产率
其中,化合物3和5的核磁共振氢谱如图3和4所示,其余不再穷举。
此外,为了进一步说明本发明公开制备的发光辅助材料在电致发光器件中的应用效果,发明人还进行了下述测试实验,具体如下:
应用例1器件实施例
采用实施例1化合物1制备有机电致发光器件,具体工艺如下:
a、ITO阳极:将涂层厚度为150nm的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,然后转移至等甩干机内进行甩干,最后用真空烘箱220℃烘烤2小时,烘烤结束后降温即可使用。以该基板为阳极,使用蒸镀机进行蒸镀器件工艺,在其上依次蒸镀其它功能层;
j、将蒸镀完成的基板进行封装:首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
器件结构:ITO/Ag/ITO/HT:P-dopant(10nm,3%)/HT(120nm)/化合物1(10nm)/Host:Dopant(25nm,2%)/ET:Liq(35nm,50%)/Yb(1nm)/Mg:Ag(18nm,1:9)/CPL(70nm)。
其中,相应物质的化学式如下:
应用例2-123
按照上述有机电致发光器件的制备方法制备应用例2-123的有机电致发光器件,区别在于将应用例1中的化合物1分别替换为其它122个化合物,形成发光辅助层;
对比例1-12
按照应用例1相同的制备方案制备有机电致发光器件,其中将化合物1分别替换为对比化合物1-12;其中,对比化合物1-12的结构式如下:
并对得到的器件的发光特性进行测试,测量采用KEITHLEY 2400型源测量单元,CS-2000分光辐射亮度计,以评价驱动电压,发光效率,具体测试结果如下表2所示:
表2应用例1-123和对比例1-12电致发光器件的性能检测结果
从表2可以看出,使用本发明提供的发光辅助材料制备的有机电致发光器件与对比例1~12提供的现有的有机电致发光器件相比,在驱动电压、发光效率、BI和寿命方面均得到显著提高。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
1.一种含芳胺基团的发光辅助材料,其特征在于,所述发光辅助材料的结构通式如式I所示:
其中,环A为经取代或未经取代的C6~C20芳基;
X为O、S、-C(R1)(R2)-和NR3中的任意一种;R1-R3各自独立的表示经取代或未经取代的C1~C12烷基、经取代或未经取代的C6~C18芳基和经取代或未经取代的3元~30元杂芳基中的任意一种;
R为经取代或未经取代的C1~C10烷基、经取代或未经取代的C6~C30芳基和经取代或未经取代的3元~30元杂芳基中的任意一种;
Ar1和Ar2为经取代或未经取代的C3~C20环烷基、经取代或未经取代的3元~30元杂环烷基、经取代或未经取代的C6~C30芳基、经取代或未经取代的3元~20元杂芳基、经取代或未经取代的C10~C30稠环基和取代或未取代的C5-C30螺环基中的至少一种。
4.根据权利要求1-3任一项所述的一种含芳胺基团的发光辅助材料,其特征在于,所述R为氢、甲基、乙基、叔丁基、甲基苯、甲氧基、苯基、萘基、联苯基、菲基、咔唑基、芴基、二甲基芴、三联苯基、苯并呋喃、苯并噻吩和吡啶基中的任意一种。
8.一种含芳胺基团的发光辅助材料的制备方法,其特征在于,包括以下具体步骤:
(1)Ar1与Ar2不相同
1)N2保护下,将中间体A-1、反应物B-1、四(三苯基膦)钯和碳酸钾依次加入到甲苯、乙醇和水的混合溶剂中,升温至100-120℃反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后将沉淀依次用水洗涤、乙醇洗涤、干燥和重结晶后,得到中间体C-1;
2)将所述中间体C-1和反应物D-1溶于甲苯后,N2保护下依次加入Pd2(dba)3、P(t-Bu)3和t-BuONa,升温至110℃反应10h,反应结束后抽滤,滤液冷却至室温,然后依次经过洗涤、分液、萃取、干燥、去除溶剂和纯化后即得化合物中间体E-1;
3)将所述中间体E-1和反应物F-1溶于甲苯后,N2保护下依次加入Pd2(dba)3、P(t-Bu)3和t-BuONa,升温至110℃反应10h,反应结束后抽滤,滤液冷却至室温,然后依次经过洗涤、分液、萃取、干燥、去除溶剂和纯化后即得化合物通式1;其中,反应合成路线如下:
(2)Ar1与Ar2相同:
1)N2保护下,将中间体A-1、反应物B-1、四(三苯基膦)钯和碳酸钾依次加入到甲苯、乙醇和水的混合溶剂中,升温至100-120℃反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后将沉淀依次用水洗涤、乙醇洗涤、干燥和重结晶后,得到中间体C-1;
2)将所述中间体C-1和反应物D-1溶于甲苯后,N2保护下依次加入Pd2(dba)3、P(t-Bu)3和t-BuONa,升温至110℃反应10h,反应结束后抽滤,滤液冷却至室温,然后依次经过洗涤、分液、萃取、干燥、去除溶剂和纯化后即得化合物通式1;其中,反应合成路线如下:
9.一种含芳胺基团的发光辅助材料的应用,其特征在于,权利要求1-7任一所述的含芳胺基团的发光辅助材料或者权利要求8所述制备方法得到的含芳胺基团的发光辅助材料在制备有机电致发光器件中的应用。
10.一种有机电致发光器件,包括:第一电极、有机物层、第二电极;其特征在于,所述有机物层包含权利要求1-7任一所述的含芳胺基团的发光辅助材料或者权利要求8所述制备方法得到的含芳胺基团的发光辅助材料。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111341735.7A CN116120265A (zh) | 2021-11-12 | 2021-11-12 | 一种含芳胺基团的发光辅助材料及其制备方法与应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111341735.7A CN116120265A (zh) | 2021-11-12 | 2021-11-12 | 一种含芳胺基团的发光辅助材料及其制备方法与应用 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116120265A true CN116120265A (zh) | 2023-05-16 |
Family
ID=86305006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111341735.7A Pending CN116120265A (zh) | 2021-11-12 | 2021-11-12 | 一种含芳胺基团的发光辅助材料及其制备方法与应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116120265A (zh) |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015088183A1 (ko) * | 2013-12-13 | 2015-06-18 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN104781233A (zh) * | 2012-11-13 | 2015-07-15 | 德山新勒克斯有限公司 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
US20160133850A1 (en) * | 2014-11-07 | 2016-05-12 | Samsung Display Co., Ltd. | Organic electroluminescent device |
CN106574179A (zh) * | 2014-08-13 | 2017-04-19 | 三星Sdi株式会社 | 有机光电装置和显示装置 |
US20170125689A1 (en) * | 2014-06-18 | 2017-05-04 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
CN107667098A (zh) * | 2015-05-27 | 2018-02-06 | 德山新勒克斯有限公司 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
CN111689889A (zh) * | 2020-07-21 | 2020-09-22 | 上海钥熠电子科技有限公司 | 芳香胺化合物及其应用 |
CN113501800A (zh) * | 2021-04-02 | 2021-10-15 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料、电子元件及电子装置 |
CN116082282A (zh) * | 2021-11-04 | 2023-05-09 | 奥来德(上海)光电材料科技有限公司 | 一种发光辅助材料及其制备方法与电致发光器件 |
-
2021
- 2021-11-12 CN CN202111341735.7A patent/CN116120265A/zh active Pending
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104781233A (zh) * | 2012-11-13 | 2015-07-15 | 德山新勒克斯有限公司 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
WO2015088183A1 (ko) * | 2013-12-13 | 2015-06-18 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US20170125689A1 (en) * | 2014-06-18 | 2017-05-04 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
CN106574179A (zh) * | 2014-08-13 | 2017-04-19 | 三星Sdi株式会社 | 有机光电装置和显示装置 |
US20160133850A1 (en) * | 2014-11-07 | 2016-05-12 | Samsung Display Co., Ltd. | Organic electroluminescent device |
CN107667098A (zh) * | 2015-05-27 | 2018-02-06 | 德山新勒克斯有限公司 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
CN111689889A (zh) * | 2020-07-21 | 2020-09-22 | 上海钥熠电子科技有限公司 | 芳香胺化合物及其应用 |
CN113501800A (zh) * | 2021-04-02 | 2021-10-15 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料、电子元件及电子装置 |
CN116082282A (zh) * | 2021-11-04 | 2023-05-09 | 奥来德(上海)光电材料科技有限公司 | 一种发光辅助材料及其制备方法与电致发光器件 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113717059B (zh) | 一种有机化合物及包含其的电子元件和电子装置 | |
CN113285038B (zh) | 一种有机电致发光器件及电子装置 | |
CN111848417A (zh) | 一种苯并蒽衍生物的有机电致发光化合物及其制备方法和应用 | |
CN111848501A (zh) | 一种含氮化合物以及使用其的电子元件和电子装置 | |
CN113121588B (zh) | 一种有机化合物及包含其的电子元件和电子装置 | |
CN115557920B (zh) | 一种发光辅助材料、其制备方法及有机电致发光器件 | |
CN115197184A (zh) | 一种发光辅助材料及其制备方法和应用 | |
CN115304566A (zh) | 一种发光辅助材料及其制备方法和应用 | |
CN114790184A (zh) | 一种发光辅助材料及其制备方法、发光器件、发光装置 | |
CN115960001A (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN113121553B (zh) | 一种有机化合物及包含其的电子元件和电子装置 | |
CN114989069A (zh) | 含氮化合物和电子元件及电子装置 | |
CN116462593B (zh) | 一种有机发光辅助材料及其制备方法与其在有机电致发光器件中的应用 | |
CN113214280A (zh) | 有机化合物及包含其的电子器件和电子装置 | |
CN112759524A (zh) | 一种芳香胺衍生物及其有机电致发光器件 | |
CN112457278A (zh) | 一种有机电致发光化合物及其制备方法与应用 | |
JP4721475B2 (ja) | ジインデノピセン化合物及びこれを使用した有機発光素子 | |
CN115521212B (zh) | 有机材料、电子元件及电子装置 | |
CN113764604B (zh) | 一种组合物及包含其的电子元件和电子装置 | |
CN115583887A (zh) | 一种有机电致发光化合物及其制备方法和应用 | |
CN116120265A (zh) | 一种含芳胺基团的发光辅助材料及其制备方法与应用 | |
CN115093335B (zh) | 一种发光辅助材料及其制备方法和应用 | |
CN110872294A (zh) | 一种发光材料及其应用 | |
CN113380954B (zh) | 有机电致发光器件及电子装置 | |
CN114426539B (zh) | 有机化合物及包含其的有机电致发光器件和电子装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |