CN109553569A - 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
- CN109553569A CN109553569A CN201811566742.5A CN201811566742A CN109553569A CN 109553569 A CN109553569 A CN 109553569A CN 201811566742 A CN201811566742 A CN 201811566742A CN 109553569 A CN109553569 A CN 109553569A
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- substituted
- atom
- aryl
- layer
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 239000000463 material Substances 0.000 claims abstract description 79
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 230000005540 biological transmission Effects 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 229910052714 tellurium Inorganic materials 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 9
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 229910052710 silicon Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004020 luminiscence type Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000006884 silylation reaction Methods 0.000 claims 1
- 230000005284 excitation Effects 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 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 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 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
- 239000012043 crude product Substances 0.000 description 12
- 239000013067 intermediate product Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 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
- 238000002156 mixing Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 238000003786 synthesis reaction 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
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 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
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- -1 bromo- thio hexichol Chemical compound 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 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
- 239000011368 organic material Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- DXDMCGNRGHZNNP-UHFFFAOYSA-N (1-bromo-2-phenylpropan-2-yl)benzene Chemical class BrCC(C)(C1=CC=CC=C1)C1=CC=CC=C1 DXDMCGNRGHZNNP-UHFFFAOYSA-N 0.000 description 1
- 150000000094 1,4-dioxanes Chemical class 0.000 description 1
- RRWFUWRLNIZICP-UHFFFAOYSA-N 1-bromo-2-phenoxybenzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1 RRWFUWRLNIZICP-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
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical compound C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 1
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 229910001632 barium fluoride Inorganic materials 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
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 150000002012 dioxanes Chemical class 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
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 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
- 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 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
- 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition 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
- 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
- 230000000007 visual effect Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/10—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 carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明属于OLED技术领域且提供了一种用作主体材料的化合物,具有式(I)的结构;其中X选自C、O、S、Se、Si或Te原子;a和b分别表示电子给体D和电子受体A的个数且选自1、2或3,c和d分别选自0、1或2;L1、L2和电子给体D各自独立地选自烷基、环烷基、杂环基、芳基、杂芳基、稠芳基或稠杂芳基;电子受体A选自含氮杂环、含氰基、含磷氧基的取代基或三芳基硼类取代基。本发明化合物中的D‑(π)‑σ‑(π)‑A结构具有双极性,σ键可有效打断电子给体D与电子受体A之间的分子内电荷传输,使激发态限制为D或A的片段内的局域激发态,因而使化合物具有小的激发态偶极矩,当其用作发光层主体材料时,可有效降低蓝光材料的效率滚降,提升发光亮度和发光效率。
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。
按发光机理可分为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,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,把重心放在研发新的磷光主体材料是研究者们共通的思路。
发明内容
有鉴于此,本发明提供一种具有D-(π)-σ-(π)-A结构的化合物,所述化合物具有式(I)所示的化学结构:
其中,X选自C、O、S、Se、Si或Te原子;当X为C或Si时,R选自氢原子、烷基、芳基或杂芳基;
D表示电子给体,A表示电子受体;其中,a和b分别表示电子给体D和电子受体A的个数且a和b分别选自1、2或3;c和d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;
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、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、三芳基硼类取代基和含磷氧基类取代基中的至少一种。
本发明的化合物具有D-(π)-σ-(π)-A结构,是一种双极性材料,可以替代现有传统的D-π-A骨架结构。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,而本发明的化合物中的D-(π)-σ-(π)-A结构同样具有双极性性质,中间的σ键可以有效打断电子给体D与电子受体A之间这种传输,使得激发态限制为电子给体D或者电子受体A的片段内的局域激发态,因而使化合物具有小的激发态偶极矩,当其用于OLED器件的发光层的主体材料时,可以有效降低蓝光材料的效率滚降,提升发光亮度和发光效率。
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一种OLED器件的结构示意图;
图3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。凡是对本发明技术方案进行修改或者等同替换,而不脱离本发明技术方案的范围,均应涵盖在本发明的保护范围中。
本发明的一方面是提供一种化合物,所述化合物具有式(Ⅰ)所示的化学结构:
其中,X选自C、O、S、Se、Si或Te原子;当X为C或Si时,R选自氢原子、烷基、芳基或杂芳基;
D表示电子给体,A表示电子受体;其中,a和b分别表示电子给体D和电子受体A的个数且a和b分别选自1、2或3;c和d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、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、三芳基硼类取代基和和含磷氧基类取代基中的至少一种。
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:
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;q选自0、1、2或3;
U4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;
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,R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:
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,电子受体A选自以下基团:
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:
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:
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,所述化合物选自以下化合物:
本发明还提供一种显示面板,所述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,所述发光层的主体材料为本发明所述的化合物中的一种或多种。
根据本发明的显示面板,其中所述有机发光器件的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,当所述发光层的主体材料为红光发光材料时,所述红光发光材料的最低三重态能级T1为2.2eV;
当所述发光层的主体材料为绿光发光材料时,所述绿光发光主体材料的最低三重态能级T1为2.5eV;
当所述发光层的发光主体材料为蓝光发光材料时,所述蓝光发光主体材料的最低三重态能级T1为2.7eV。
根据本发明所述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。
根据本发明所述显示面板的一个实施方式,所述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、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本发明所述的化合物。
在本发明所述的显示面板中,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;金属氧化物例如,氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;导电性聚合物例如,聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除了以上有助于空穴注入材料及其组合之外,阳极材料还可包括其他已知的适合做阳极的材料。
在本发明所述的显示面板中,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;多层金属材料例如,LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合之外,阴极材料还可包括其他已知的适合做阴极的材料。
在本发明的一个实施例中,所述的显示面板中的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。最后在阴极上制备一层有机光学覆盖层CPL(盖帽层)。光学覆盖层CPL的材料为本发明所述的化合物。光学覆盖层CPL可以通过蒸镀或溶液法加工制备。溶液加工法包括喷墨打印法、旋转涂布、刮刀涂布、丝网印刷、卷对卷印刷等方法。
下面提供几个示例性的化合物的合成示例。
实施例1
化合物H001的合成
在250ml圆底烧瓶中,将4,4’-二溴-二苯醚(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和二芳胺(25mmol)加入到干燥的1,4-二恶烷(400毫升)中,在N2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,同时用二氯甲烷萃取,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H001-1。
在250ml圆底烧瓶中,将中间产物H001-1(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,同时用二氯甲烷萃取,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H001-2。
在250ml圆底烧瓶中,H001-2(10mmol)、1-氯-3,5-二苯基三嗪(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N2氛围下回流反应12h。得到的产品冷却到室温,加入水中,然后通过硅藻土垫过滤,同时用二氯甲烷萃取,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H001。
化合物H001元素分析结构(分子式C39H28N4O):理论值:C,82.37;H,4.96;N,9.85;O,2.81。测试值:C,82.37;H,4.96;N,9.87;O,2.79。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:568.23,测试值:568.67。
实施例2
化合物H013的合成
在250ml圆底烧瓶中,将4,4’-二溴-1-硫代二苯(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和5,10-二氢吩嗪(25mmol)加入到干燥的1,4-二恶烷(400毫升)中,在N2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,同时用二氯甲烷萃取,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H013-1。
在250ml圆底烧瓶中,将中间产物H013-1(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,同时用二氯甲烷萃取,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H013-2。
在250ml圆底烧瓶中,H013-2(10mmol)、4-溴-2,6-二苯基吡啶(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N2氛围下回流反应12h。得到的产品冷却到室温,加入水中,然后通过硅藻土垫过滤,同时用二氯甲烷萃取,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H013。
化合物H013元素分析结构(分子式C41H29N3S):理论值:C,82.66;H,4.91;N,7.05;S,5.38。测试值:C,82.66;H,4.91;N,7.04;S,5.39。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:595.21,测试值:595.75。
实施例3
化合物H024的合成
在250ml圆底烧瓶中,将4,4’-二溴-二苯基二甲基丙烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9H-咔唑(25mmol)加入到干燥的1,4-二恶烷(400毫升)中,在N2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,同时用二氯甲烷萃取,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H024-1。
在250ml圆底烧瓶中,将中间产物H024-1(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,同时用二氯甲烷萃取,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H024-2。
在250ml圆底烧瓶中,H024-2(10mmol)、1-二苯磷氧基-二苯并噻吩(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N2氛围下回流反应12h。得到的产品冷却到室温,加入水中,然后通过硅藻土垫过滤,同时用二氯甲烷萃取,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H024。
化合物H024元素分析结构(分子式C51H38NOPS):理论值:C,82.34;H,5.15;N,1.88;O,2.15;P,4.16;S,4.31。测试值:C,82.34;H,5.16;N,1.88;O,2.15;P,4.17;S,4.29。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:743.24,测试值:743.75。
实施例4
化合物H031的合成
在250ml圆底烧瓶中,将4,4’-二溴-二苯基丙烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9,9-二甲基-9,10-二氢吖啶(25mmol)加入到干燥的1,4-二恶烷(400毫升)中,在N2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,同时用二氯甲烷萃取,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H031-1。
在250ml圆底烧瓶中,将中间产物H031-1(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,同时用二氯甲烷萃取,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H031-2。
在250ml圆底烧瓶中,H031-2(10mmol)、4-溴-2,6-二苯基吡啶(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N2氛围下回流反应12h。得到的产品冷却到室温,加入水中,然后通过硅藻土垫过滤,同时用二氯甲烷萃取,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H031。
化合物H031元素分析结构(分子式C57H44N2):理论值:C,90.44;H,5.86;N,3.70。测试值:C,90.44;H,5.87;N,3.69。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:756.35,测试值:756.58。
表1示例性化合物的能级值
化合物 | HOMO(eV) | LUMO(eV) | Eg(eV) | E<sub>T</sub>(eV) |
H001 | -5.589 | -2.507 | 3.082 | 2.9348 |
H013 | -5.737 | -2.497 | 3.240 | 2.9563 |
H024 | -5.658 | -2.343 | 3.315 | 2.9806 |
H031 | -5.640 | -2.442 | 3.198 | 2.9587 |
从表1可以看出,作为主体材料,H001、H013、H024和H031显示出合适的HOMO与LUMO能级以及很高的三线态ET(>2.9ev),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。
实施例5
本实施例提供了一种有机发光器件。如图2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H001作为主体材料,Ir(ppy)3作为掺杂材料,化合物H001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。
实施例6
器件制作过程同实施例1,不同之处在于主体材料为H013,其他各层材料均相同。
实施例7
器件制作过程同实施例1,不同之处在于主体材料为H024,其他各层材料均相同。
实施例8
器件制作过程同实施例1,不同之处在于主体材料为H031,其他各层材料均相同。
对比例1
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有机发光器件的性能表征
从表2可以看出,相对于对比例中的器件,使用本发明所述化合物发光器件具有更低的驱动电压,约下降8.5%,可以有效降低器件的功耗;应用的器件具有更高的发光效率,约提升20%-25%左右,可以有效的提升器件的发光亮度及寿命。
本发明的又一方面还提供一种显示装置,其包括如上文所述的有机发光显示面板。
在本发明中,有机发光显示装置可以是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3是根据本发明的实施例提供的一种显示装置的示意图。在图3中,11表示手机显示屏。
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 (18)
1.一种化合物,所述化合物具有式(I)所示的化学结构:
其中,X选自C、O、S、Se、Si或Te原子;当X为C或Si时,R选自氢原子、烷基、芳基或杂芳基;
D表示电子给体,A表示电子受体;其中,a和b分别表示电子给体D和电子受体A的个数且a和b分别选自1、2或3;c和d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、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,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;
#表示连接位置。
3.根据权利要求2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。
4.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;q选自0、1、2或3;
U4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;
当Z为氧原子或硫原子时,q为0;
#表示连接位置。
5.根据权利要求4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:
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:
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。
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。
8.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。
9.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。
10.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。
11.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。
12.根据权利要求1所述的化合物,其特征在于,所述化合物选自以下化合物:
13.一种显示面板,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12任一项所述的化合物中的一种或多种。
14.根据权利要求13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。
15.根据权利要求13所述的显示面板,其特征在于,当所述发光层的主体材料为红光发光材料时,所述红光发光材料的最低三重态能级T1为2.2eV;
当所述发光层的主体材料为绿光发光材料时,所述绿光发光主体材料的最低三重态能级T1为2.5eV;
当所述发光层的发光主体材料为蓝光发光材料时,所述蓝光发光主体材料的最低三重态能级T1为2.7eV。
16.根据权利要求13至15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。
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、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12任一项所述的化合物。
18.一种显示装置,包括权利要求13至17任一项所述的显示面板。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811566742.5A CN109553569B (zh) | 2018-12-19 | 2018-12-19 | 化合物、显示面板以及显示装置 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811566742.5A CN109553569B (zh) | 2018-12-19 | 2018-12-19 | 化合物、显示面板以及显示装置 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109553569A true CN109553569A (zh) | 2019-04-02 |
CN109553569B CN109553569B (zh) | 2020-11-27 |
Family
ID=65870780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811566742.5A Active CN109553569B (zh) | 2018-12-19 | 2018-12-19 | 化合物、显示面板以及显示装置 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109553569B (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109956965A (zh) * | 2019-04-30 | 2019-07-02 | 上海天马有机发光显示技术有限公司 | 化合物、有机发光显示面板以及显示装置 |
CN110734438A (zh) * | 2019-10-30 | 2020-01-31 | 上海天马有机发光显示技术有限公司 | 一种化合物及包含其的有机电致发光器件、电子设备 |
CN110845538A (zh) * | 2019-11-29 | 2020-02-28 | 上海天马有机发光显示技术有限公司 | 一种有机化合物及其应用 |
CN111834537A (zh) * | 2019-07-18 | 2020-10-27 | 广州华睿光电材料有限公司 | 一种包含光取出层的有机电致发光器件 |
CN113387905A (zh) * | 2021-06-09 | 2021-09-14 | 东南大学 | 一种有机室温磷光材料、制备方法和应用 |
CN113527279A (zh) * | 2021-07-13 | 2021-10-22 | 京东方科技集团股份有限公司 | 一种发光薄膜及其制备方法、发光器件及显示装置 |
WO2023065506A1 (zh) * | 2021-10-18 | 2023-04-27 | 深圳先进技术研究院 | 一种孔雀石绿硼酸酯及其衍生物、制备方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016116487A1 (de) * | 2015-01-20 | 2016-07-28 | Cynora Gmbh | Organische moleküle zur verwendung in optoelektronischen bauelementen |
CN108026079A (zh) * | 2015-09-24 | 2018-05-11 | 株式会社Lg化学 | 化合物和包含其的有机发光器件 |
CN108129386A (zh) * | 2018-01-23 | 2018-06-08 | 吉林大学 | 基于打断共轭的给受体型分子内基激复合物发光材料及其在制备有机电致发光器件中的应用 |
-
2018
- 2018-12-19 CN CN201811566742.5A patent/CN109553569B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016116487A1 (de) * | 2015-01-20 | 2016-07-28 | Cynora Gmbh | Organische moleküle zur verwendung in optoelektronischen bauelementen |
CN108026079A (zh) * | 2015-09-24 | 2018-05-11 | 株式会社Lg化学 | 化合物和包含其的有机发光器件 |
CN108129386A (zh) * | 2018-01-23 | 2018-06-08 | 吉林大学 | 基于打断共轭的给受体型分子内基激复合物发光材料及其在制备有机电致发光器件中的应用 |
Non-Patent Citations (1)
Title |
---|
YI-ZHONG SHI,等: "Intermolecular Charge-Transfer Transition Emitter Showing Thermally Activated Delayed Fluorescence for Efficient Non-Doped OLEDs", 《ANGEW. CHEM. INT. ED.》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109956965A (zh) * | 2019-04-30 | 2019-07-02 | 上海天马有机发光显示技术有限公司 | 化合物、有机发光显示面板以及显示装置 |
CN109956965B (zh) * | 2019-04-30 | 2021-12-17 | 武汉天马微电子有限公司 | 化合物、有机发光显示面板以及显示装置 |
CN111834537A (zh) * | 2019-07-18 | 2020-10-27 | 广州华睿光电材料有限公司 | 一种包含光取出层的有机电致发光器件 |
CN110734438A (zh) * | 2019-10-30 | 2020-01-31 | 上海天马有机发光显示技术有限公司 | 一种化合物及包含其的有机电致发光器件、电子设备 |
CN110845538A (zh) * | 2019-11-29 | 2020-02-28 | 上海天马有机发光显示技术有限公司 | 一种有机化合物及其应用 |
CN110845538B (zh) * | 2019-11-29 | 2023-04-07 | 武汉天马微电子有限公司 | 一种有机化合物及其应用 |
CN113387905A (zh) * | 2021-06-09 | 2021-09-14 | 东南大学 | 一种有机室温磷光材料、制备方法和应用 |
CN113527279A (zh) * | 2021-07-13 | 2021-10-22 | 京东方科技集团股份有限公司 | 一种发光薄膜及其制备方法、发光器件及显示装置 |
WO2023065506A1 (zh) * | 2021-10-18 | 2023-04-27 | 深圳先进技术研究院 | 一种孔雀石绿硼酸酯及其衍生物、制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN109553569B (zh) | 2020-11-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110028459B (zh) | 化合物、显示面板以及显示装置 | |
CN110156756A (zh) | 化合物、显示面板以及显示装置 | |
CN109535064B (zh) | 化合物、显示面板以及显示装置 | |
CN109553569A (zh) | 化合物、显示面板以及显示装置 | |
CN110041357B (zh) | 化合物、显示面板以及显示装置 | |
CN109456256A (zh) | 化合物、显示面板以及显示装置 | |
CN110128403B (zh) | 化合物、显示面板以及显示装置 | |
CN107068888B (zh) | 一种含有酮和氮杂环类化合物的有机电致发光器件及其应用 | |
CN110156611A (zh) | 一种苯基枝化发光材料及其有机电致发光器件 | |
CN109705148A (zh) | 芳香环化合物、显示面板以及显示装置 | |
CN111892607B (zh) | 一种n杂联苯类有机化合物及其应用 | |
CN113816979B (zh) | 一种有机化合物及其电致发光的应用 | |
CN110615809B (zh) | 化合物、显示面板以及显示装置 | |
CN111454244B (zh) | 一种化合物、显示面板及显示装置 | |
CN109503466A (zh) | 有机化合物、显示面板及显示装置 | |
CN114447245A (zh) | 一种有机电致发光器件与显示设备 | |
CN108440573A (zh) | 一种化合物及制备方法、一种有机发光显示装置 | |
CN109503576B (zh) | 有机化合物、显示面板及显示装置 | |
CN110669040A (zh) | 化合物、显示面板和显示装置 | |
CN110256495A (zh) | 一种化合物、有机电致发光器件及显示装置 | |
CN113563381A (zh) | 一种有机电致发光化合物及其应用 | |
CN106749243B (zh) | 双偶极化合物、包含其的发光层主体材料、oled显示面板和电子设备 | |
CN108864042A (zh) | 一种氮杂稠环并茚化合物及有机发光显示装置 | |
CN108864054A (zh) | 一种氮杂环化合物以及有机发光显示装置 | |
CN110272410B (zh) | 一种化合物、发光材料、有机光电装置以及电子设备 |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |