CN114805390B - 一种有机化合物及其电致发光的应用 - Google Patents
一种有机化合物及其电致发光的应用 Download PDFInfo
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- CN114805390B CN114805390B CN202210508535.4A CN202210508535A CN114805390B CN 114805390 B CN114805390 B CN 114805390B CN 202210508535 A CN202210508535 A CN 202210508535A CN 114805390 B CN114805390 B CN 114805390B
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- triazinyl
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- substituted
- heteroaryl
- aryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- -1 1,3, 4-triazinyl Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 15
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 15
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 15
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 15
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 22
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 15
- 125000002950 monocyclic group Chemical group 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004969 haloethyl group Chemical group 0.000 description 2
- 125000004970 halomethyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWGAMUODYKBQLG-UHFFFAOYSA-N N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 Chemical class N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 PWGAMUODYKBQLG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004440 column chromatography Methods 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
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 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
- 239000000975 dye Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 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
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound 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
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
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Abstract
本发明提供了一种有机化合物,具有式Ⅰ所示结构。本发明提供了一种以N原子杂环为骨架的发光层主体材料,具有合适的LUMO和HOMO值,同时其具有较高的三线态能级,可以有效阻挡激子的传输,将激子限制在发光层中,提升空穴的传输,利于提升器件的发光效率和寿命。
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种有机化合物及其电致发光的应用。
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,把重心放在研发磷光主体材料是研究者们共通的思路。
现在使用的磷光材料存在寿命不够长,效率不够高及驱动电压比较高的缺陷,是目前亟需解决的问题。
发明内容
有鉴于此,本发明要解决的技术问题在于提供一种有机化合物及其电致发光的应用,可以有效提升器件的发光效率和寿命。
本发明提供了一种有机化合物,具有式Ⅰ所示结构:
其中,R1选自取代或未取代的芳基、杂芳基或芳胺基;
R2选自取代或未取代的芳基或杂芳基。
本发明提供了一种有机发光器件,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括空穴传输层,所述空穴传输层中含有至少一种上述有机化合物。
本发明提供了一种有机发光器件,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括电子阻挡层,所述电子阻挡层中含有至少一种上述有机化合物。
本发明提供了一种显示面板,包括上述有机发光器件。
与现有技术相比,本发明提供了一种有机化合物,具有式Ⅰ所示结构。本发明提供了一种以N原子杂环为骨架的发光层主体材料,具有合适的LUMO和HOMO值,同时其具有较高的三线态能级,可以有效阻挡激子的传输,将激子限制在发光层中,提升空穴的传输,利于提升器件的发光效率和寿命。
附图说明
图1为本发明提供的有机发光器件的结构示意图。
具体实施方式
本发明提供了一种有机化合物,具有式Ⅰ所示结构:
其中,R1选自取代或未取代的芳基、杂芳基或芳胺基;
R2选自取代或未取代的芳基或杂芳基。
可选的,所述R1选自取代或未取代的C6~C20的芳基、C3~C20的杂芳基或NR3R4;
所述R3、R4独立的选自取代或未取代的C6~C20的芳基或C3~C20的杂芳基;
所述C6~C20的芳基、C3~C20的杂芳基、R3、R4的取代基独立的选自氘、卤素、氰基、C1~C10的烷基、C1~C10的卤代烷基,C1~C10的氘代烷基,取代或未取代的芳胺基、C6~C12的芳基或C3~C20的杂芳基。
可选的,所述R1选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~5个环稠合形成的稠环杂芳基或NR3R4;所述杂芳基的杂原子选自N、O或S;
上述稠合形成稠合杂芳基的环可以是单环芳基或单环杂芳基,且至少包括一个单环杂芳基。上述单环杂芳基为五元环或六元环,其杂原子可以为N、O、S中的一种或多种。
可选的,所述稠合形成稠合杂芳基的单环芳基为苯基。
可选的,所述稠合形成稠合杂芳基的单环杂芳基包括但不限于吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、吡喃基等。
所述R3、R4独立的选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~5个环稠合形成的稠环杂芳基;所述杂芳基的杂原子选自N、O或S;
上述稠合形成稠合杂芳基的环可以是单环芳基或单环杂芳基,且至少包括一个单环杂芳基。上述单环杂芳基为五元环或六元环,其杂原子可以为N、O、S中的一种或多种。
可选的,所述稠合形成稠合杂芳基的单环芳基为苯基。
可选的,所述稠合形成稠合杂芳基的单环杂芳基包括但不限于吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、吡喃基等。
所述R1的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基,C1~C6的氘代烷基,取代或未取代的芳胺基、单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~3个环稠合形成的稠环杂芳基中的一种或多种。
上述稠合形成稠合杂芳基的环可以是单环芳基或单环杂芳基,且至少包括一个单环杂芳基。上述单环杂芳基为五元环或六元环,其杂原子可以为N、O、S中的一种或多种。
可选的,所述稠合形成稠合杂芳基的单环芳基为苯基。
可选的,所述稠合形成稠合杂芳基的单环杂芳基包括但不限于吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、吡喃基等。
上述芳胺基由N原子和芳基和/或杂芳基组成,所述芳基可以选自取代或非取代的苯基、萘基、蒽基、菲基或联苯基;所述杂芳基可以选自取代或非取代的吡啶基、咔唑基、二苯并呋喃基或二苯并噻吩基。上述芳基、杂芳基可以进一步被D、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基,C1~C6的氘代烷基,苯基、萘基、二苯胺基、咔唑基中的一种或多种取代。可选的,所述C1~C6的烷基选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基或新戊基。可选的,所述C1~C6的氘代烷基选自氘代甲基、氘代乙基、氘代正丙基、氘代异丙基、氘代正丁基、氘代异丁基或氘代叔丁基。
可选的,所述R1选自取代或未取代的苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、蒽基、菲基、芘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、吲哚并咔唑基、菲啰啉基或N R3R4;
所述R3、R4独立的选自取代或未取代的苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、二苯并呋喃基或二苯并噻吩基。
可选的,所述R1的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基、C1~C6的氘代烷基,取代或未取代的苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基、二苯并噻吩基或N R5R6;
所述R5、R6独立的选自取代或未取代的苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基、二苯并噻吩基、二苯胺基中的一种或多种。
可选的,所述取代基可进一步被氘、卤素、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C5氘代烷基、苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基、二苯并噻吩基、二苯胺基中的一种或多种取代。
可选的,所述C1~C5的烷基选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基或新戊基。可选的,所述C1~C5的卤代烷基选自卤代甲基、卤代乙基、卤代正丙基、卤代异丙基、卤代正丁基、卤代异丁基或卤代叔丁基。可选的,所述C1~C5的氘代烷基选自氘代甲基、氘代乙基、氘代正丙基、氘代异丙基、氘代正丁基、氘代异丁基或氘代叔丁基。
可选的,所述R2选自取代或未取代的C6~C20的芳基或C3~C20的杂芳基;
所述R2的取代基独立的选自氘、卤素、氰基、C1~C10的烷基、C1~C10的卤代烷基,C1~C10的氘代烷基,取代或未取代的芳胺基、C6~C12的芳基或C3~C20的杂芳基。
可选的,所述R2选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~3个环稠合形成的稠环杂芳基。
上述稠合形成稠环杂芳基的环可以是单环芳基或单环杂芳基,且至少包括一个单环杂芳基。上述单环杂芳基为五元环或六元环,其杂原子可以为N、O、S中的一种或多种。
可选的,所述稠合形成稠合杂芳基的单环芳基为苯基。
可选的,所述稠合形成稠合杂芳基的单环杂芳基包括但不限于吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、吡喃基等。
可选的,所述R2选自取代或未取代的苯基、萘基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、蒽基、菲基、芘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基或二苯并噻吩基。
可选的,所述R2的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基、C1~C6的氘代烷基,取代或未取代的苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基或二苯并噻吩基。
可选的,所述C1~C6的烷基选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基或新戊基。可选的,所述C1~C6的卤代烷基选自卤代甲基、卤代乙基、卤代正丙基、卤代异丙基、卤代正丁基、卤代异丁基或卤代叔丁基。可选的,所述C1~C6的氘代烷基选自氘代甲基、氘代乙基、氘代正丙基、氘代异丙基、氘代正丁基、氘代异丁基或氘代叔丁基。
可选的,所述有机化合物,具有以下任一结构:
上述结构式中的单键表示甲基。
上述有机化合物可按以下路线制备:
然后用上述产物和R1B(OH)2进行取代反应即可制备得到上述有机化合物。
本发明提供了一种有机发光器件,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括空穴传输层,所述空穴传输层中含有至少一种上述有机化合物。
本发明提供了一种有机发光器件,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括电子阻挡层,所述电子阻挡层中含有至少一种上述有机化合物。
本发明提供了一种显示面板,包括上述有机发光器件。
本发明提供的有机发光器件可以为本领域技术人员熟知的有机发光器件,本发明可选的,所述有机发光器件包括基板、ITO阳极、第一空穴传输层、第二空穴传输层、电子阻挡层、发光层、第一电子传输层、第二电子传输层、阴极(镁银电极,镁银质量比为1:9)和盖帽层(CPL)。
本发明可选的,所述有机发光器件的阳极材料可选自金属-铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金;如金属氧化物-氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;如导电性聚合物-聚苯胺、聚吡咯、聚(3-甲基噻吩)等,除以上有助于空穴注入材料及其组合,还包括已知的适合做阳极的材料。
本发明可选的,所述有机发光器件的阴极材料可选自金属-铝、镁、银、铟、锡、钛等及它们的合金;如多层金属材料-LiF/Al、LiO2/Al、BaF2/Al等;除以上有助于电子注入的材料及其组合,还包括已知的适合做阴极的材料。
本发明可选的,所述有机光电装置,如有机发光器件中的有机薄膜层至少有一层发光层(EML),还可以包含其他功能层,包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)。
本发明可选的,所述有机发光器件按照以下方法制备:
在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。
本发明可选的,形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明提供了一种显示装置,包括上述显示面板。
在本发明中,有机发光器件(OLED器件)可以用在显示装置中,其中有机发光显示装置可以是手机显示屏、电脑显示屏、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。
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
反应路线如下:
1)C的合成:
向三口瓶中通入氮气置换15min,加入0.20mol反应物A、0.20mol反应物B、500mLDMF,缓慢加入0.6mol碳酸铯,开始搅拌,升温至180℃反应6h,反应结束后,冷却至室温。用二氯甲烷萃取分离有机相,水洗至中性,使用无水MgSO4干燥有机相,过滤后将滤液减压蒸馏浓缩;以淋洗剂EA:Hept=1:10过柱,得到中间体C。
2)D的合成:
向三口瓶中通入氮气置换15min,加入0.175mol中间体C、0.0035mol烯丙基氯化[1,3-双(2,6-二异丙基苯)咪唑-2-基]钯、0 525mol碳酸钾、800mL DMAc,开始搅拌,升温至125℃反应12h,反应结束后,冷却至室温。用二氯甲烷萃取分离有机相,水洗至中性,使用无水MgSO4干燥有机相,过滤后将滤液减压蒸馏浓缩;以淋洗剂DCM:Hept=1:4过柱,得到中间体D。
3)F的合成:
向三口瓶中通入氮气置换15min,加入0.1mol中间体D、0.09mol反应物E和180mLN-甲基2-吡咯烷酮,开始搅拌,升温至150℃反应16h。反应结束后冷却至室温,反应液减压蒸馏除去溶剂,所得固体粗品用二氯甲烷溶解后水洗至中性,分液后,有机相用无水MgSO4干燥后减压蒸馏,所得固体用乙酸乙酯和石油醚(体积比1:3)混合溶剂重结晶,得到中间体F。
4)G的合成:
向三口瓶中通入氮气置换15min,加入0.07mol中间体F、0.17molPPh3、300mL二氯苯,开始搅拌,回流反应5h,反应结束后,冷却至室温。用二氯甲烷和去离子水萃取分离有机相,使用无水MgSO4干燥有机相,过滤后,将滤液减压蒸馏除去溶剂。使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯,得到中间体G。
5)H的合成:
将10mmol的中间体G、10mmol的反应物J、0.5mmol的Pd2dba3(三(二亚苄基丙酮)二钯(0))和30mmol的叔丁醇钠溶于80mL的甲苯中,在80℃下搅拌3小时。将反应溶液冷却至室温,使用40mL的水和50mL的乙醚萃取有机层三次。使用无水MgSO4干燥萃取的有机层,蒸发溶剂。用硅胶柱色谱法分离和纯化得到中间体H。
6)H1的合成:
在250mL圆底烧瓶中,将10mmol反应物H,12mmol反应物G1和80mmol Na2CO3分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)溶剂中,形成混合溶液,然后将0.5mmol Pd(PPh3)4加入到上述混合溶液中,在氮气气氛下进行回流反应20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MgSO4干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到化合物H1。
MALDI-TOF:m/z:计算值:C48H31N3O:665.25,实测值:665.33。
化合物元素分析结果:计算值:C48H31N3O(%):C,86.59;H,4.69;N,6.31;O,2.40;测试值:C,86.58;H,4.70;N,6.32;O,2.41。
实施例2
化合物H3的合成方法与H1的合成方法相似,区别在于,将反应6)中的G1替换为等摩尔量的G3。
MALDI-TOF:m/z:计算值:C48H29N3O:663.23,实测值:663.49。
化合物元素分析结果:计算值:C48H29N3O(%):C,86.86;H,4.40;N,6.33;O,2.41;测试值:C,86.84;H,4.41;N,6.35;O,2.40。
实施例3
化合物H10的合成方法与H1的合成方法相似,区别在于,将反应6)中的G1替换为等摩尔量的G10。
MALDI-TOF:m/z:计算值:C60H40N4O:832.32,实测值:832.56。
化合物元素分析结果:计算值:C60H40N4O(%):C,86.51;H,4.84;N,6.73;O,1.92;测试值:C,86.53;H,4.83;N,6.74;O,1.91。
实施例4
化合物H23的合成方法与H1的合成方法相似,区别在于,将反应1)中的B替换为等摩尔量的B’;将反应6)中的G1替换为等摩尔量的G23。
MALDI-TOF:m/z:计算值:C56H35N3O:765.28,实测值:765.52。
化合物元素分析结果:计算值:C56H35N3O(%):C,87.82;H,4.61;N,5.49;O,2.09;测试值:C,87.80;H,4.62;N,5.50;O,2.08。
实施例5
化合物H33的合成方法与H23的合成方法相似,区别在于,将反应6)中的G23替换为等摩尔量的G33。
MALDI-TOF:m/z:计算值:C48H21D10N3O:675.31,实测值:675.49。
化合物元素分析结果:计算值:C48H21D10N3O(%):C,85.30;H,6.11;N,6.22;O,2.37;测试值:C,85.32;H,6.10;N,6.22;O,2.36。
实施例6
化合物H23的合成方法与H1的合成方法相似,区别在于,将反应5)中的J替换为等摩尔量的J’;将反应6)中的G1替换为等摩尔量的G78。
MALDI-TOF:m/z:计算值:C52H31N3O:713.25,实测值:713.54。
化合物元素分析结果:计算值:C52H31N3O(%):C,87.49;H,4.38;N,5.89;O,2.24;测试值:C,87.48;H,4.39;N,5.87;O,2.25。
应用例1
本应用例提供一种OLED器件,如图1所示,图1为本发明提供的有机发光器件的结构示意图,包括依次层叠的基板1,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与盖帽层9。其中氧化铟锡(ITO)阳极15nm、第一空穴传输层10nm、第二空穴传输层95nm、发光层30nm、第一电子传输层35nm、第二电子传输层5nm、阴极15nm(镁银电极,镁银质量比为1:9)、盖帽层(CPL)100nm。
OLED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30min,然后暴露在臭氧下清洁10min;将通过磁控溅射所得的具有ITO阳极2的玻璃基板安装到真空沉积设备上;
(2)在真空度为2×10-6Pa下,在ITO阳极层2上真空蒸镀化合物HAT-CN,厚度为10nm,作为第一空穴传输层3;
(3)在第一空穴传输层3上真空蒸镀化合物TAPC作为第二空穴传输层4,厚度为95nm;
(4)在第二空穴传输层4上真空蒸镀发光层5,采用本发明提供的有机化合物H1和化合物H101作为主体材料(H1与H101的质量比为55:45),Ir(piq)2(acac)作为掺杂材料,主体材料和Ir(piq)2(acac)的质量比为97:3,厚度为30nm;
(5)在发光层上真空蒸镀化合物BCP作为第一电子传输层6,厚度为35nm;
(6)在第一电子传输层6上真空蒸镀化合物Alq3作为第二电子传输层7,厚度为5nm;
(7)在第二电子传输层7上真空蒸镀镁银电极作为阴极8,Mg和Ag质量比为1:9,厚度为15nm;
(8)在阴极8上真空蒸镀高折射率的化合物CBP,厚度为100nm,作为阴极覆盖层(盖帽层)9使用。
所述OLED器件中用到的化合物结构如下:
应用例2~8
将应用例1中步骤(4)中的有机化合物H1分别替换为等量的化合物H3、H10、H23、H33、H78、H88或H94,其他制备步骤同应用例1。
对比例
一种OLED器件,其与应用例1的区别仅在于,将步骤(4)中的主体材料用等量的对比化合物HH替换;其它原料及制备步骤均相同。
OLED器件的性能评价:
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度下(10mA/cm2)的启亮电压和电流效率(CE,Cd/A),Von为亮度1Cd/m2下的启亮电压;通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);具体数据如表1所示。
表1 OLED器件性能检测结果
从表1可以看出,相较于对比例(REF)的有机电致发光器件,应用例1-8的有机电致发光器件性能得到大幅提升。主要体现为器件的驱动电压降低了3.6%以上,效率提升了6.1%以上,而器件的LT95寿命提升了5.9%以上。这可能是因为本发明特殊的结构,本发明以吲哚基团与类吖啶基团稠合形成核心基团,吲哚并类吖啶衍生物作为发光层的主体材料时,由于其较大的电子云密度,使发光层的空穴迁移率得以提升,有助于有机发光层中的电子与空穴达到平衡,提高电致发光器件的发光效率以及降低有机电致发光器件的驱动电压。吲哚与类吖啶基团进行键合,降低了分子对称性,可以改善化合物的成膜性,从而提高电流效率和发光效率。
以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以对本发明进行若干改进和修饰,这些改进和修饰也落入本发明权利要求的保护范围内。
Claims (11)
1.一种有机化合物,具有式Ⅰ所示结构:
其中,
所述R1选自取代或未取代的C6~C20的芳基、C3~C20的杂芳基或NR3R4;
所述R3、R4独立的选自取代或未取代的C6~C20的芳基、C3~C20的杂芳基或芴基;
所述C6~C20的芳基、C3~C20的杂芳基、R3、R4的取代基独立的选自氘、卤素、氰基、C1~C10的烷基、C1~C10的卤代烷基,C1~C10的氘代烷基,取代或未取代的芳胺基、C6~C12的芳基或C3~C20的杂芳基;
所述R2选自取代或未取代的C6~C20的芳基或C3~C20的杂芳基;
所述R2的取代基独立的选自氘、卤素、氰基、C1~C10的烷基、C1~C10的卤代烷基,C1~C10的氘代烷基,取代或未取代的芳胺基、C6~C12的芳基或C3~C20的杂芳基。
2.根据权利要求1所述的有机化合物,其特征在于,所述R1选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~5个环稠合形成的稠环杂芳基或NR3R4;
所述R3、R4独立的选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~5个环稠合形成的稠环杂芳基;
所述杂芳基的杂原子选自N、O或S;
所述R1的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基,C1~C6的氘代烷基,取代或未取代的芳胺基、单环芳基、2个环稠合形成的稠环芳基、单环杂芳基、2~3个环稠合形成的稠环杂芳基中的一种或多种。
3.根据权利要求2所述的有机化合物,其特征在于,所述R1选自取代或未取代的苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、蒽基、菲基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、吲哚并咔唑基、菲啰啉基或NR3R4;
所述R3、R4独立的选自取代或未取代的苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、二苯并呋喃基或二苯并噻吩基。
4.根据权利要求3所述的有机化合物,其特征在于,所述R1的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基、C1~C6的氘代烷基,取代或未取代的苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、二苯并呋喃基、二苯并噻吩基或N R5R6;
所述R5、R6独立的选自取代或未取代的苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、二苯并呋喃基、二苯并噻吩基中的一种或多种。
5.根据权利要求4所述的有机化合物,其特征在于,所述苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、二苯并呋喃基、二苯并噻吩基或N R5R6可进一步被氘、卤素、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C5氘代烷基、苯基、联苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、芴基、吖啶基、二苯并呋喃基、二苯并噻吩基、二苯胺基中的一种或多种取代。
6.根据权利要求1所述的有机化合物,其特征在于,所述R2选自取代或未取代的单环芳基、2~3个环稠合形成的稠环芳基、单环杂芳基、2~3个环稠合形成的稠环杂芳基。
7.根据权利要求6所述的有机化合物,其特征在于,所述R2选自取代或未取代的苯基、萘基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、蒽基、菲基、芘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、二苯并呋喃基或二苯并噻吩基。
8.根据权利要求1所述的有机化合物,其特征在于,所述R2的取代基选自氘、卤素、氰基、C1~C6的烷基、C1~C6的卤代烷基、C1~C6的氘代烷基,取代或未取代的苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、1,2,3-三嗪基,1,3,5-三嗪基、1,3,4-三嗪基、萘基、喹啉基、喹喔啉基、异喹啉基、喹唑啉基、咔唑基、吖啶基、二苯并呋喃基或二苯并噻吩基。
9.一种有机化合物,其特征在于,具有以下任一结构:
10.一种有机发光器件,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层,所述发光层中含有至少一种如权利要求1-9任一项所述的有机化合物。
11.一种显示面板,包括权利要求10所述的有机发光器件。
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