CN110028459A - 化合物、显示面板以及显示装置 - Google Patents
化合物、显示面板以及显示装置 Download PDFInfo
- Publication number
- CN110028459A CN110028459A CN201910441335.XA CN201910441335A CN110028459A CN 110028459 A CN110028459 A CN 110028459A CN 201910441335 A CN201910441335 A CN 201910441335A CN 110028459 A CN110028459 A CN 110028459A
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- Prior art keywords
- unsubstituted
- substituted
- atom
- layer
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 239000000463 material Substances 0.000 claims abstract description 84
- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 10
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 10
- -1 heteroaromatic ketone Chemical class 0.000 claims abstract description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 150000003457 sulfones Chemical class 0.000 claims abstract description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 81
- 230000005540 biological transmission Effects 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052710 silicon Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 230000004888 barrier function Effects 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000006884 silylation reaction Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000013067 intermediate product Substances 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 4
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- IELSRSCLRGXCFP-UHFFFAOYSA-N 1-phenyladamantan-2-amine Chemical compound NC1C(C2)CC(C3)CC2CC13C1=CC=CC=C1 IELSRSCLRGXCFP-UHFFFAOYSA-N 0.000 description 2
- XQCWLKDHJVKLGS-UHFFFAOYSA-N 2,2-bis(4-iodophenyl)adamantane Chemical compound C1=CC(I)=CC=C1C1(C=2C=CC(I)=CC=2)C(C2)CC3CC2CC1C3 XQCWLKDHJVKLGS-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical class N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 239000012965 benzophenone Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- AELBZZMQJAJEJW-UHFFFAOYSA-N 1-bromo-9-phenylcarbazole Chemical compound BrC1=CC=CC(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 AELBZZMQJAJEJW-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N acridan acid Natural products C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000004411 aluminium Substances 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000004292 cytoskeleton Anatomy 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
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 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 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000003724 hair brightness Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 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
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009967 tasteless effect Effects 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
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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Abstract
本发明提供一种具有D‑(π)‑σ‑(π)‑A型化学结构的化合物,所述化合物具有式(I)所示的化学结构,L1和L2选自单键、C1‑C20亚烷基、C3‑C20亚环烷基、C3‑C20亚杂环基、C6‑C40亚芳基、C4‑C40亚杂芳基、C10‑C60的亚稠芳基或C10‑C60的亚稠杂芳基中的至少一种;电子给体D选自C1‑C20烷基、C3‑C20环烷基、C1‑C20烷氧基、C3‑C20杂环基、C6‑C40芳基、C4‑C40杂芳基、C10‑C60的亚稠芳基、C10‑C60的亚稠杂芳基、C12‑C40的咔唑基及其衍生物基团、C12‑C40的二苯胺基及其衍生物基团、C18‑C60的三苯胺基及其衍生物基团、C12‑C40的吖啶基及其衍生物基团;电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基、砜类取代基和含磷氧基类取代基。本发明提供了一系列D‑(π)‑σ‑(π)‑A结构的双极性材料,可提升发光亮度和发光效率EQE。
Description
技术领域
本发明涉及有机电致发光材料技术领域,具体地涉及一种化合物以及包括该化合物的显示面板以及显示装置。
背景技术
有机电致发光材料(OLED)作为新一代显示技术,具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点,已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
发光机理上有电致荧光和电致磷光两种,荧光是单重态激子的辐射衰减跃迁所发射的光,磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论,单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25%的限制,外量子效率普遍低于5%;电致磷光材料的内量子效率理论上达到100%,外量子效率可达20%。1998年,我国吉林大学的马於光教授和美国普林斯顿大学的Forrest教授分别报道了采用锇配合物和铂配合物作为染料掺杂入发光层,第一次成功得到并解释了磷光电致发光现象,并开创性的将所制备磷光材料应用于电致发光器件。
由于磷光重金属材料有较长的寿命(μs),在高电流密度下,可能导致三线态-三线态湮灭和浓度淬灭,造成器件性能衰减,因此通常将重金属磷光材料掺杂到合适的主体材料中,形成一种主客体掺杂体系,使得能量传递最优化,发光效率和寿命最大化。在目前的研究现状中,重金属掺杂材料商业化已成熟,很难开发可替代的掺杂材料。因此,把重心放在研发磷光主体材料是研究者们共通的思路。
发明内容
鉴于此,本发明提供一种以D-(π)-σ-(π)-A结构的双极性化合物,所述化合物具有式(I)所示的化学结构:
其中,D表示电子给体,A表示电子受体;其中,m和n分别表示电子给体D和电子受体A的个数且m和n分别选自1、2或3,p和q分别表示L1和L2的个数且分别选自0、1或2;
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种;
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种;
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基、砜类取代基和含磷氧基类取代基中的至少一种。
本发明提供了一系列以D-(π)-σ-(π)-A结构的双极性材料,替代传统的D-π-A双极性材料,具有很强的分子内电荷传输能力,导致大的偶极矩μs;该系列的有机化合物D-(π)-σ-(π)-A结构同样具有双极性性质,中间的σ键可以有效打断供体D和受体A之间这种传输,使得激发态限制为供体D或者受体A的片段内的局域激发态,具有小的激发态偶极矩,提升发光亮度和发光效率EQE。
本发明的化合物作为磷光主体材料可满足以下设计要求:
(i)主体材料的三线态能级ET高于磷光客体材料的ET,防止从客体材料到主体材料之间的三线态能量倒流,从而将三线态激子最大程度限制在发光层内;
(ii)主体材料的HOMO能级与LUMO能级与相邻层材料的能级相匹配,以减少空穴和电子注入势垒,降低器件的驱动电压;此外,主体材料的HOMO和LUMO能级差Eg应大于磷光客体材料的HOMO和LUMO能级差Eg,有利于主体到客体的能量转移以及载流子在磷光客体上的直接俘获;
(iii)主体材料具有较高的载流子传输速率以及平衡的载流子传输性能,以利于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域,提高发光效率;
(iv)主体材料具有良好的热稳定性和成膜性,适当的玻璃化温度Tg,以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。
作为电致发光器件中的主体材料,具有较高的三线态能级ET和较大的分子密度,较高的玻璃化温度和分子热稳定性,有效提高载流子的平衡迁移,扩宽激子复合区域,有效提高光的取出效率,使得器件的发光效率和寿命有了很大提升,在电致发光器件技术领域中可以得到很好的应用。
本发明的化合物所涉及的金刚烷(Adamantane)的化学名称为三环[3,3,1,13,7]癸烷,是由10个碳原子和16个氢原子构成的环状四面体碳氢化合物,外观为无色晶体,熔点268℃,相对密度1.07,折光率1.568,无毒、无味,易升华,不溶于水,微溶于苯。金刚烷的单元组成是椅式构像环己烷,整个环系具有对称性及刚性特征。金刚烷是一种具备与金刚石构造相同结构的碳原子数为10的脂环式碳水化合物,由于它的结构单位全部是椅子型状的环己烷,因此它具有结构整齐,透明性和稳定性等优良的特点,通常情况下不与硝酸及高锰酸钾作用,但其分子中的氢原子易发生SNl型亲核取代反应和SE2型亲电取代反应。另外,在一定条件下,金刚烷分子也会发生骨架重排、氧化、烷基化等类型的反应,使得其在医药、功能高分子、润滑剂、表面活性剂、催化剂、照相材料等方面具有广泛的用途,被誉为新一代精细化工原料。
本发明还提供了一种显示面板和一种显示装置。
附图说明
图1是本发明实施例提供的化合物的化学通式;
图2是本发明实施例提供的化合物的所采用的母核金刚烷的结构示意图;
图3是本发明实施例提供的一种OLED的结构示意图;
图4是本发明实施例提供的一种显示装置的示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明,这些实施例只是用于说明本发明,本发明不限于以下实施例。
本发明的一方面提供一种化合物,所述化合物具有式(I)所示的化学结构:
其中,D表示电子给体,A表示电子受体;其中,m和n分别表示电子给体D和电子受体A的个数且m和n分别选自1、2或3,p和q分别表示L1和L2的个数且分别选自0、1或2;
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种;
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、取代或未取代的C12-C40的吖啶基及其衍生物基团中的至少一种;
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基、砜类取代基和含磷氧基类取代基中的至少一种。
本发明提供的化合物是D-(π)-σ-(π)-A结构的双极性材料,其替代传统的D-π-A双极性材料,具有很强的分子内电荷传输,导致大的偶极矩μs;该系列的有机化合物D-(π)-σ-(π)-A结构同样具有双极性性质,中间的σ键可以有效打断供体D和受体A之间这种传输,使得激发态限制为供体D或者受体A的片段内的局域激发态,具有小的激发态偶极矩,提升发光亮度和发光效率EQE。
本发明提供的化合物作为电致发光器件中的主体材料时,具有较高的三线态能级ET和较大的分子密度,较高的玻璃化温度和分子热稳定性,可有效提高载流子的平衡迁移,扩宽激子复合区域,可有效提高光的取出效率,使得器件的发光效率和寿命有了很大提升,在电致发光器件技术领域中可以得到很好的应用。
根据本发明所述化合物的一个实施方式,L1与L2选自相同的基团。
根据本发明所述化合物的一个实施方式,L1与L2选自不同的基团。
根据本发明所述化合物的一个实施方式,p=0,q=1。
根据本发明所述化合物的一个实施方式,m=n=1。
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
其中,m、n和p各自独立地选自0、1、2或3;
U1、U2、U3各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
#表示连接位置。
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
其中,R选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C10-C30稠芳基、取代或未取代的C4-C40杂芳基。
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
Z选自C原子、N原子、O原子、S原子或Si原子;
其中,m、n和q各自独立地选自0、1、2或3;U1、U2、U3和U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
当Z为氧原子或硫原子时,q为0;
#表示连接位置。
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
Z选自C原子、N原子、O原子、S原子或Si原子;X选自C原子、N原子、O原子或S原子;m、n、p和q各自独立地选自0、1、2或3;
U1、U2、U3、U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
当Z或X为氧原子或硫原子时,p或q为0;
#表示连接位置。
根据本发明所述化合物的一个实施方式,所述电子给体D选自以下基团中的至少一种:
其中,R1、R2、R3和R4分别独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基。
根据本发明所述化合物的一个实施方式,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置;
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40芳基、C4-C40杂芳基。
根据本发明所述化合物的一个实施方式,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
根据本发明所述化合物的一个实施方式,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
根据本发明所述化合物的一个实施方式,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
根据本发明所述化合物的一个实施方式,所述化合物选自下列化合物:
根据本发明的化合物可以用作OLED发光层的主体材料。
本发明提供了四个示例性化合物H002、H018、H075和H077的制备方法,如下示例性实施例1至实施例4所述。
实施例1
化合物H002的合成
在250ml圆底烧瓶中,将中间产物H002-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60ml)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时(h)。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H002-2。
在250ml圆底烧瓶中,H002-2(10mmol)、3-溴-9-苯基-9H-咔唑(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30ml)/乙醇(20ml)和碳酸钾(12mmol)水溶液(10ml)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物H002-3。
在250ml圆底烧瓶中,H002-3(10mmol)、4-溴-2,6-二联苯基三嗪(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30ml)/乙醇(20ml)和碳酸钾(12mmol)水溶液(10ml)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物H002。
化合物H002元素分析:理论值:C,84.59;H,6.23;N,9.18;测试值:C,84.59;H,6.23;N,9.18。MALDI-TOF MS:m/z C43H38N4的计算值:610.31;测量值:610.30。
实施例2
化合物H018的合成
在250ml圆底烧瓶中,将2-金刚烷酮(15mmol)、5-氨基嘧啶(40mmol)、HCl(20ml),在氩气氛围下回流14小时,得到双氨基苯基金刚烷产物H018-1。
在250ml圆底烧瓶中,将中间产物H018-1(15mmol)和NaNO2(40mmol)、HCl(20ml),在0℃下氩气氛围下搅拌6小时。再加入KI(40mmol),在0℃下氩气氛围下搅拌48小时。得到的中间体,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H018-2。
在250ml圆底烧瓶中,将中间产物H018-2(15mmol)和醋酸钾(80mmol)与干燥的1,4-二氧六环(100ml)、Pd(PPh3)2Cl2(0.8mmol)和联硼酸频那醇酯(50mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物H018。
化合物H018元素分析:理论值:C,78.75;H,8.13;N,13.12;测试值:C,78.75;H,8.13;N,13.12。MALDI-TOF MS:m/z C42H52N6的计算值:640.43;测量值:640.42。
实施例3
中间体H075-1的合成
在250ml圆底烧瓶中,将2-金刚烷酮(15mmol)、苯胺(40mmol)、HCl(20ml),在氩气氛围下回流14小时,得到双氨基苯基金刚烷产物H075-0。
在250ml圆底烧瓶中,将中间产物H075-0(15mmol)和NaNO2(40mmol)、HCl(20ml),在0℃下氩气氛围下搅拌6小时。再加入KI(40mmol),在0℃下氩气氛围下搅拌48小时。得到的中间体,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H075-1。
化合物H075的合成
在250ml圆底烧瓶中,将2,2-双(4-碘代-苯基)-金刚烷(15mmol)、氧化亚铜(40mmol)、DMAC(20ml),在氩气氛围下回流48小时,得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H075-2。
在250ml圆底烧瓶中,将中间产物H075-2(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60ml)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H075-3。
在250ml圆底烧瓶中,H075-3(10mmol)、2-氯-4,6-二苯基-1,3,5-三嗪(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30ml)/乙醇(20ml)和碳酸钾(12mmol)水溶液(10ml)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物H075。
化合物H075元素分析:理论值:C,89.70;H,6.16;N,4.14;测试值:C,89.70;H,6.15;N,64.15。MALDI-TOF MS:m/z C51H42N2的计算值:682.3;测量值:682.2。
实施例4
化合物H077的合成
在250ml圆底烧瓶中,将2,2-双(4-碘代-苯基)-金刚烷(15mmol)、9,9-二甲基-9,10-二氢吖啶(20mmol),氧化亚铜(40mmol)、DMAC(20ml),在氩气氛围下回流48小时,得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H077-1。
在250ml圆底烧瓶中,将中间产物H077-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60ml)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物H077-2。
在250ml圆底烧瓶中,H077-2(10mmol)、2-氯-4,6-二苯基-1,3,5-三嗪(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30ml)/乙醇(20ml)和碳酸钾(12mmol)水溶液(10ml)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物H077。
化合物H077元素分析:理论值:C,77.70;H,15.33;N,6.97;测试值:C,77.70;H,15.33;N,6.97。MALDI-TOF MS:m/z,C52H123N4的计算值:803.97;测量值:803.96。
化合物性能测试
(1)化合物模拟计算
运用密度泛函理论(DFT),利用Gaussian 09程序包在B3LYP/6-31G(d)计算水平下,优化并计算得到本发明的化合H002、H018、H075和H077的分子前线轨道的分布情况;同时基于含时密度泛函理论(TD-DFT),模拟计算了H002、H018、H075和H077各化合物分子的单线态能级S1和三线态能级T1,结果如表1所示,其中Eg=HOMO-LUMO,Eg的数值取绝对值。
表1示例性化合物的能级
化合物 | HOMO(eV) | LUMO(eV) | Eg(eV) | E<sub>T</sub>(eV) |
H002 | -5.276 | -1.752 | 3.524 | 3.0217 |
H018 | -5.575 | -1.465 | 4.110 | 3.1603 |
H075 | -5.257 | -1.840 | 3.417 | 2.9840 |
H077 | -5.248 | -0.727 | 4.521 | 3.1482 |
从表1可以看出,作为主体材料,H002、H018、H075和H077显示出合适的HOMO与LUMO能级以及很高的三线态ET(>2.85ev),适合应用于红光(ET至少>2.2ev)、绿光(ET至少>2.5ev)和蓝光(ET至少>2.7ev),可以有效地实现主客体之间的能量传递且不会有电荷回传的风险。
本发明还提供一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,其中发光层包括主体材料和客体材料,其特征在于,所述发光层的主体材料为以上所述的化合物中的一种或多种。
根据本发明的显示面板的一个实施方式,所述发光层为蓝色发光层,所述主体材料为蓝色发光层的主体材料。
根据本发明的显示面板的一个实施方式,所述发光层为绿色发光层,所述主体材料为绿色发光层的主体材料。
根据本发明的显示面板的一个实施方式,所述主体材料的单重态能级S1高于所述客体材料的单重态能级S1,且主体材料的单重态能级S1与客体材料的单重态能级S1的差值小于0.8eV;所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1,且主体材料的三重态能级T1与客体材料的三重态能级T1的差值小于0.4eV。
根据本发明的显示面板的一个实施方式,所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
本发明的一个方面还提供一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,以及位于所述阴极背离所述阳极一侧的盖帽层,以及位于所述阳极与所述阴极之间的有机层,所述有机层包括电子传输层、空穴传输层和发光层,所述盖帽层与所述电子传输层、空穴传输层、发光层中的至少一者的材料为以上所述的化合物。
在本发明提供的显示面板中,有机发光器件的阳极材料可以选自金属例如铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金。阳极材料也可以选自金属氧化物如氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;阳极材料还可以选自导电性聚合物例如聚苯胺、聚吡咯、聚(3-甲基噻吩)等。此外,阳极材料还可以选自除以列举的阳极材料以外的有助于空穴注入的材料及其组合,其包括已知的适合做阳极的材料。
在本发明提供的显示面板中,有机发光器件的阴极材料可以选自金属例如铝、镁、银、铟、锡、钛等及它们的合金。阴极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的阴极材料以外,阴极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做阴极的材料。
有机发光器件可以按照本领域公知的方法进行制作,在此不再详述。在本发明中,有机发光器件可以这样制作: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。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
下面提供了示例性的器件实施例,用于说明本发明的化合物在有机发光显示面板中的实际应用。
器件实施例1
本实施例提供了一种有机发光器件。如图3所示,有机发光器件包括:玻璃基板1、ITO阳极2、第一空穴传输层3、第二空穴传输层4、发光层5、第一电子传输层6、第二电子传输层7、阴极8(镁银电极,镁银质量比为9:1)和盖帽层(CPL)9,其中ITO阳极2的厚度是15nm,第一空穴传输层3的厚度是10nm、第二空穴传输层4的厚度是95nm、发光层5的厚度是30nm、第一电子传输层6的厚度是35nm、第二电子传输层7的厚度是5nm、镁银电极8的厚度是15nm和盖帽层(CPL)9的厚度是100nm。
本发明的有机发光器件的制备步骤如下:
1)将玻璃基板1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10分钟来进行清洁;将所得的具有ITO阳极的玻璃基板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HAT-CN,厚度为10nm,该层作为第一空穴传输层3;
3)在第一空穴传输层3上真空蒸镀第二空穴传输层2材料为TAPC,厚度为110nm,作为第二空穴传输层4;
4)空穴传输层4上共沉积发光层5,其中,化合物H002作为主体材料,Ir(ppy)3作为掺杂材料,化合物H003与Ir(ppy)3的质量比为19:1,厚度为30nm;
5)在发光层5上真空蒸镀第一电子传输层6,第一电子传输层6的材料为BPen,厚度为30nm;
6)在第一电子传输层6上真空蒸镀第二电子传输层7,第二电子传输层7的材料为Alq3,厚度为5nm;
7)在第二电子传输层7上真空蒸镀镁银电极,其中,质量比Mg:Ag为9:1,厚度为15nm,作为阴极8;
8)在阴极8上真空蒸镀高折射率的空穴型材料CBP,厚度为100nm,作为阴极覆盖层(盖帽层或CPL)9使用。
本实施例涉及的化合物及其结构如下所示。
器件实施例2
器件制作过程同器件实施例1,不同之处在于主体材料为H018,其他各层材料均相同。
器件实施例3
器件制作过程同器件实施例1,不同之处在于主体材料为H075,其他各层材料均相同。
器件实施例4
器件制作过程同器件实施例1,不同之处在于主体材料为H077,其他各层材料均相同。
器件对比例1
对比器件制作过程同实施例1,不同之处在于主体材料为CzTRZ,其他各层材料均相同。
表2器件性能表征
编号 | 主体材料 | 驱动电压(V) | EQE/% | CE(cd/A) |
实施例1 | H002 | 3.50 | 27.2 | 128.9 |
实施例2 | H018 | 3.12 | 30.3 | 134.7 |
实施例3 | H075 | 3.49 | 31.7 | 120.1 |
实施例4 | H077 | 3.76 | 33.6 | 126.8 |
对比例1 | CzTRZ | 4.10 | 24.2 | 103.2 |
由表2可知,与对比例1相比,应用本发明的化合物的光学器件的驱动电压较低,电流效率较高,亮度较高。
本发明还提供了一种显示装置,其包括如上文所述的有机发光显示面板。在本发明中,有机发光器件可以是OLED,其可以用在有机发光显示装置中,其中有机发光显示装置可以是手机显示屏、电脑显示屏、液晶电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。图4是根据本发明实施例提供的一种显示装置的示意图。在图4中,10表示手机显示面板,20表示显示装置。
本申请虽然以较佳实施例公开如上,但并不是用来限定权利要求,任何本领域技术人员在不脱离本申请构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (23)
1.一种化合物,其特征在于,所述化合物具有式(I)所示的化学结构:
其中,D表示电子给体,A表示电子受体;其中,m和n分别表示电子给体D和电子受体A的个数且m和n分别选自1、2或3,p和q分别表示L1和L2的个数且分别选自0、1或2;
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种;
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、取代或未取代的C12-C40的吖啶基及其衍生物基团中的至少一种;
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基、砜类取代基和含磷氧基类取代基中的至少一种。
2.根据权利要求1所述的化合物,其特征在于,L1与L2选自相同的基团。
3.根据权利要求1所述的化合物,其特征在于,L1与L2选自不同的基团。
4.根据权利要求1所述的化合物,其特征在于,p=0,q=1。
5.根据权利要求1所述的化合物,其特征在于,m=n=1。
6.根据权利要求1所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
其中,m、n和p各自独立地选自0、1、2或3;
U1、U2、U3各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
#表示连接位置。
7.根据权利要求6所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
其中,R选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C10-C30稠芳基、取代或未取代的C4-C40杂芳基。
8.根据权利要求1所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
Z选自C原子、N原子、O原子、S原子或Si原子;
其中,m、n和q各自独立地选自0、1、2或3;U1、U2、U3和U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
当Z为氧原子或硫原子时,q为0;
#表示连接位置。
9.根据权利要求8所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
10.根据权利要求1所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
Z选自C原子、N原子、O原子、S原子或Si原子;X选自C原子、N原子、O原子或S原子;m、n、p和q各自独立地选自0、1、2或3;
U1、U2、U3、U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种;
当Z或X为氧原子或硫原子时,p或q为0;
#表示连接位置。
11.根据权利要求10所述的化合物,其特征在于,所述电子给体D选自以下基团中的至少一种:
其中,R1、R2、R3和R4分别独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基。
12.根据权利要求1所述的化合物,其特征在于,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置;
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40芳基、C4-C40杂芳基。
13.根据权利要求1所述的化合物,其特征在于,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
14.根据权利要求1所述的化合物,其特征在于,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
15.根据权利要求1所述的化合物,其特征在于,所述电子受体A选自以下基团中的至少一种:
其中,#表示连接位置。
16.根据权利要求1所述的化合物,其特征在于,所述化合物选自下列化合物:
17.一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,其中发光层包括主体材料和客体材料,其特征在于,所述发光层的主体材料为权利要求1至16任一项所述的化合物中的一种或多种。
18.根据权利要求17所述的显示面板,其特征在于,所述发光层为蓝色发光层,所述主体材料为蓝色发光层的主体材料。
19.根据权利要求17所述的显示面板,其特征在于,所述发光层为绿色发光层,所述主体材料为绿色发光层的主体材料。
20.根据权利要求17所述的显示面板,其特征在于,所述主体材料的单重态能级S1高于所述客体材料的单重态能级S1,且主体材料的单重态能级S1与客体材料的单重态能级S1的差值小于0.8eV;所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1,且主体材料的三重态能级T1与客体材料的三重态能级T1的差值小于0.4eV。
21.根据权利要求17至20任一项所述的显示面板,其特征在于,所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
22.一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,以及位于所述阴极背离所述阳极一侧的盖帽层,以及位于所述阳极与所述阴极之间的有机层,所述有机层包括电子传输层、空穴传输层和发光层,所述盖帽层与所述电子传输层、空穴传输层、发光层中的至少一者的材料为权利要求1至17任一项所述的化合物。
23.一种显示装置,包括权利要求17至22任一项所述的显示面板。
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---|---|---|---|---|
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WO2021233311A1 (zh) * | 2020-05-20 | 2021-11-25 | 陕西莱特光电材料股份有限公司 | 有机化合物以及使用其的电子元件和电子装置 |
US20220220084A1 (en) * | 2019-12-30 | 2022-07-14 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic component and electronic apparatus |
CN115490601A (zh) * | 2022-04-18 | 2022-12-20 | 陕西莱特光电材料股份有限公司 | 有机化合物、电子元件及电子装置 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1202608A2 (en) * | 2000-10-30 | 2002-05-02 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Organic light-emitting devices |
US6777111B1 (en) * | 1999-08-04 | 2004-08-17 | Kabushiki Kaisha Chuo Kenkyusho | Electro luminescent element |
CN102482571A (zh) * | 2009-03-20 | 2012-05-30 | 罗门哈斯电子材料韩国有限公司 | 新的有机电致发光化合物和使用该化合物的有机电致发光设备 |
CN104178123A (zh) * | 2013-05-28 | 2014-12-03 | 海洋王照明科技股份有限公司 | 吡咯并吲哚基蓝光磷光主体材料及其制备方法和有机电致发光器件 |
CN104529870A (zh) * | 2015-01-23 | 2015-04-22 | 武汉大学 | 一类金刚烷衍生物及其作为有机电致磷光主体材料的应用 |
CN105190930A (zh) * | 2013-04-11 | 2015-12-23 | 新日铁住金化学株式会社 | 有机电致发光元件用金刚烷化合物及有机电致发光元件 |
WO2017205425A1 (en) * | 2016-05-24 | 2017-11-30 | President And Fellows Of Harvard College | Compounds for organic light emitting diode materials |
-
2019
- 2019-05-24 CN CN201910441335.XA patent/CN110028459B/zh active Active
- 2019-12-31 US US16/732,136 patent/US11785841B2/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6777111B1 (en) * | 1999-08-04 | 2004-08-17 | Kabushiki Kaisha Chuo Kenkyusho | Electro luminescent element |
EP1202608A2 (en) * | 2000-10-30 | 2002-05-02 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Organic light-emitting devices |
CN102482571A (zh) * | 2009-03-20 | 2012-05-30 | 罗门哈斯电子材料韩国有限公司 | 新的有机电致发光化合物和使用该化合物的有机电致发光设备 |
CN105190930A (zh) * | 2013-04-11 | 2015-12-23 | 新日铁住金化学株式会社 | 有机电致发光元件用金刚烷化合物及有机电致发光元件 |
CN104178123A (zh) * | 2013-05-28 | 2014-12-03 | 海洋王照明科技股份有限公司 | 吡咯并吲哚基蓝光磷光主体材料及其制备方法和有机电致发光器件 |
CN104529870A (zh) * | 2015-01-23 | 2015-04-22 | 武汉大学 | 一类金刚烷衍生物及其作为有机电致磷光主体材料的应用 |
WO2017205425A1 (en) * | 2016-05-24 | 2017-11-30 | President And Fellows Of Harvard College | Compounds for organic light emitting diode materials |
Non-Patent Citations (2)
Title |
---|
HIROHIKO FUKAGAWA ET AL.: "Novel Hole-Transporting Materials with High Triplet Energy for Highly Efficient and Stable Organic Light-Emitting Diodes", 《J. PHYS. CHEM. C》 * |
顾宇: "基于金刚烷桥连的高能隙有机电致磷光主体材料的合成及其性能研究", 《中国优秀博硕士学位论文全文数据库(博士)信息科技辑》 * |
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US11434208B2 (en) * | 2019-12-30 | 2022-09-06 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic component and electronic apparatus |
US11444252B2 (en) | 2019-12-30 | 2022-09-13 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Nitrogen-containing compound, organic electroluminescent device and electronic apparatus |
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