CN115109065B - 有机化合物、主体材料和有机电致发光器件 - Google Patents
有机化合物、主体材料和有机电致发光器件 Download PDFInfo
- Publication number
- CN115109065B CN115109065B CN202210921528.7A CN202210921528A CN115109065B CN 115109065 B CN115109065 B CN 115109065B CN 202210921528 A CN202210921528 A CN 202210921528A CN 115109065 B CN115109065 B CN 115109065B
- Authority
- CN
- China
- Prior art keywords
- compound
- organic
- unsubstituted
- substituted
- groups
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 45
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 239000000126 substance Substances 0.000 claims abstract description 12
- 239000010410 layer Substances 0.000 claims description 46
- 239000012044 organic layer Substances 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 abstract description 9
- 125000005842 heteroatom Chemical group 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 66
- -1 arylphosphine groups Chemical group 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 40
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
- 238000004128 high performance liquid chromatography Methods 0.000 description 31
- 238000000034 method Methods 0.000 description 30
- 238000006257 total synthesis reaction Methods 0.000 description 25
- 239000007858 starting material Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000012300 argon atmosphere Substances 0.000 description 9
- 229910052796 boron Inorganic materials 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 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 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229910052805 deuterium Inorganic materials 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000004404 heteroalkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 4
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229940127204 compound 29 Drugs 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003480 eluent Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 101100269674 Mus musculus Alyref2 gene Proteins 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 101100537098 Mus musculus Alyref gene Proteins 0.000 description 1
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 101150095908 apex1 gene Proteins 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- VKRWRNVGVPSVLA-UHFFFAOYSA-N n,n'-bis(2-phenylphenyl)oxamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1NC(=O)C(=O)NC1=CC=CC=C1C1=CC=CC=C1 VKRWRNVGVPSVLA-UHFFFAOYSA-N 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D471/06—Peri-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
- C07D471/22—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 systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- 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
- C07D498/22—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 four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- 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
-
- 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
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明公开了有机化合物、主体材料和有机电致发光器件,该有机化合物具有如式(1)所示的化学结构,Ar1选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基,Z1–Z8选自‑CR1‑或N;A、B和C选自取代或未取代的C6–C30芳基或C5–C30杂芳基,至少一个选自O、S、‑CR2R3‑、‑NR4‑、‑SiR5R6‑、
Description
技术领域
本发明属于有机光电材料领域,特别涉及有机化合物、主体材料和有机电致发光器件。
背景技术
有机电致发光(OLED)器件是一类具有类三明治结构的器件,包括正负电极膜层及夹在电极膜层之间的有机功能材料层,该技术已被广泛应用于新型照明灯具、智能手机和平板电脑等产品的显示面板,还将向电视等大尺寸显示产品应用领域扩展,是发展快、技术要求高的新型显示技术。OLED材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和应用前景。
随着多媒体信息技术的发展,对平板显示器件性能要求越来越高,目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件,其中OLED具有自身发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列优点,与液晶显示器件相比,OLED不需要背光源、视角宽和功耗低,响应速度是液晶显示器件的1000倍,具有更广阔的应用前景。自OLED第一次被报道以来,许多学者致力于研究提高器件效率和稳定性。Forrest和Thompson等研究人员发现过渡金属配合物能应用于Ph OLEDs,磷光材料存在很强的自旋轨道耦合作用,能同时利用单线态和三线态激子,使磷光电致发光器件内量子效率在理论上达到100%,然而磷光材料激发态寿命较长,当三线态激子浓度较高时容易形成三线态-三线态凐灭和三线态-极化子间凐灭。通常将磷光材料作为客体材料掺入到主体材料中,以此降低自浓度淬灭过程,磷光有机电致发光器件主体材料所需的特性:(1)较高的三线态能级;(2)较好的载流子迁移率且能与相邻层能级匹配;(3)高的热稳定性和成膜稳定性。目前OLED显示和照明得到广泛的商业化应用,客户终端对OLED屏体光电和寿命要求不断提升,除在OLED面板制程工艺上精益求精,开发满足更高器件指标的OLED材料特别是稳定高效的主体材料具有重要的应用价值。
发明内容
基于此,本发明提供一类稳定高效的可用于红色和绿色磷光有机电致发光器件的有机化合物,其具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配,同时还具有较高的热稳定性和成膜稳定性,用于红色和绿色磷光有机电致发光器件能够降低驱动电压,提高器件发光效率,延长器件寿命。
本发明的一方面提供一种有机化合物,其具有如式(1)所示的化学结构:
式(1)中,Ar1选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基;
Z1–Z8相同或不相同,独立选自-CR1-或N;
A、B和C独立选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基,且至少一个选自O、S、-CR2R3-、-NR4-、-SiR5R6-或者如下基团中的一种或多种:
其中,X2和X3各自独立选自-CR7-、-SiR8-或N;
X1、X4、X5和X6各自独立选自O、S、-CR9R10-、-NR11-或-SiR12R13-;
R和R1-R13相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1–C30烷基、取代或未取代的C1–C30杂烷基、取代或未取代的C3–C30环烷基、取代或未取代的C3–C30杂环烷基、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或者与相邻的原子键合成环。
本发明还提供一种主体材料,其包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物选自式(1)所示的有机化合物中的一种或多种,所述第二主体化合物的化学结构由通式(2)表示:
式(2)中,Ar5、Ar6和Ar7各自独立选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或与相邻的原子键合成环。
本发明还提供一种有机层,包括式(1)所示的有机化合物中的一种或多种、或者所述主体材料中的一种或多种。
本发明还提供一种有机电致发光器件,其包括第一电极、第二电极和所述有机层,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一种。
本发明还提供一种显示或照明装置,其包括所述有机电致发光器件。
与现有技术相比,本发明的有益效果在于:本发明的有机化合物引入大量稠环,使整体的环变大的同时,为避免化合物的三线态能级降低,在环中引入了碳单键或杂原子基团,使整个化合物的共轭适中,保证化合物的三线态能级维持一个较高的水平同时,提高热稳定性。本发明的有机化合物作为主体材料用于有机电致发光器件,具有较高的三线态能级、较好的载流子迁移率、较高的热稳定性和成膜稳定性,用于红色和绿色磷光有机电致发光器件能够降低驱动电压,提高器件发光效率,延长器件寿命。
具体实施方式
以下详细说明具体公开的有机化合物及其在有机电致发光器件中应用的实施方式,本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效,还可以通过另外不同的具体实施方式加以实施或应用,本说明书中的各项细节也可以基于不同观点与应用,在没有背离本发明的精神下进行各种修饰或改变。
在进一步描述本发明具体实施方式之前,应理解,本发明的保护范围不局限于下述特定的具体实施方案;还应当理解,本发明实施例中使用的术语是为了描述特定的具体实施方案,而不是为了限制本发明的保护范围;在本发明说明书和权利要求书中,除非文中另外明确指出,单数形式“一个”、“一”和“这个”包括复数形式。
以下对本发明的化合物通式结构中取代基描述如下,但取代基并不限于此:
【取代或未取代】是指经选自以下的一个或更多个取代基取代:氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基和杂芳基,苊基,化合物基团,或未取代;或者经连接以上示例的取代基中的两个或更多个取代基的取代基取代,或未取代;例如,“连接两个或更多个取代基的取代基”可包括联苯基,即联苯基可为芳基,或者为连接两个苯基的取代基。
【烷基】可为直链或支链的,并且碳原子数没有特别限制,包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基。
以上对烷基的描述也可用于芳烷基、芳烷基胺基、烷基芳基和烷基胺基中的烷基。
【杂烷基】可为含杂原子的直链或支链的烷基,并且碳原子数没有特别限制,包括但不限于可以烷氧基、烷硫基、烷基磺酰基等。烷氧基例如可以包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基等。烷硫基包括但不限于甲硫基、乙硫基、正丙硫基、异丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、新戊硫基、异戊硫基、正己硫基、3,3-二甲基丁硫基、2-乙基丁硫基、正辛硫基、正壬硫基、正癸硫基、苄硫基等。
【环烷基】可为环状的,并且碳原子数没有特别限制,包括但不限于环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等。
【杂环烷基】可为含杂原子的环烷基,并且碳原子数没有特别限制,包括但不限于等。
【芳基】没有特别限定,芳基可为单环芳基或多环芳基,单环芳基包括但不限于苯基、联苯基、三联苯基、四联苯基、五联苯基等,多环芳基包括但不限于萘基、蒽基、菲基、芘基、苝基、芴基等,芴基可为经取代的,例如9,9’-二甲基芴基、9,9’-二苯并芴基等。此外,取代基中的两个可彼此结合形成螺环结构,例如9,9’-螺二芴基等。
以上对芳基的描述可用于亚芳基,不同之处在于亚芳基为二价。
以上对芳基的描述可用于芳氧基、芳基硫基、芳基磺酰基、芳基膦基、芳烷基、芳烷基胺基、芳烯基、烷基芳基、芳基胺基和芳基杂芳基胺基中的芳基。
【杂芳基】包含N、O、P、S、Si和Se中的一个或多个作为杂原子,包括但不限于吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基、螺[芴-9,9'-氧杂蒽]、苯联萘基、二萘并呋喃基、萘苯并呋喃基、二萘并噻吩基、萘苯并噻吩基、三苯基氧化膦、三苯基硼烷等。
以上对杂芳基的描述可用于杂芳基胺基和芳基杂芳基胺基中的杂芳基。
以上对杂芳基的描述可用于亚杂芳基,不同之处在于亚杂芳基为二价的。
本发明提供的一种有机化合物,其具有如式(1)所示的化学结构:
式(1)中,Ar1选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基;
Z1–Z8相同或不相同,独立选自-CR1-或N;
A、B和C独立选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基,且至少一个选自O、S、-CR2R3-、-NR4-、-SiR5R6-或者如下基团中的一种或多种:
其中,X2和X3各自独立选自-CR7-、-SiR8-或N;
X1、X4、X5和X6各自独立选自O、S、-CR9R10-、-NR11-或-SiR12R13-;
R和R1-R13相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1–C30烷基、取代或未取代的C1–C30杂烷基、取代或未取代的C3–C30环烷基、取代或未取代的C3–C30杂环烷基、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或者与相邻的原子键合成环。
一些实施方式中,式(1)中,A、B和C独立选自取代或未取代的C6–C30亚芳基、取代或未取代的C5–C30亚杂芳基,且与相邻基团连接的方式选自单键、多键或者与相邻基团形成并环中的一种或多种。
一些实施方式中,式(1)中,A或B独立选自O、S、-CR16R17-、-NR18-、-SiR19R20-;其中:R16-R20相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1–C30烷基、取代或未取代的C1–C30杂烷基、取代或未取代的C3–C30环烷基、取代或未取代的C3–C30杂环烷基、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或者与相邻的原子键合成环。
一些实施方式中,式(1)中,Ar1选自取代或未取代的C5–C30杂芳基,其中杂原子选自N或O,且至少含有两个N。
一些实施方式中,式(1)中,Ar1选自苯基、联苯基、成环数为2–4的稠环芳基、咔唑基、中的一种或多种。
一些实施方式中,式(1)所示的有机化合物选自以下化学结构中的一种或多种:
一些实施方式中,式(1)所示的有机化合物选自以下化学结构中的一种或多种:
/>
/>
本发明还提供一种主体材料,其包含至少一种第一主体化合物和至少一种第二主体化合物,其中第一主体化合物选自有机化合物中的一种或多种,第二主体化合物的化学结构由通式(2)表示:
式(2)中,Ar5、Ar6和Ar7各自独立选自取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或与相邻的原子键合成环。
一些实施方式中,式(2)中,Ar5、Ar6和Ar7选自如下基团中的一种或多种:
其中,X7和X8相同或不相同,独立选自单键、O、S、-CR28R29-、-SiR30R31-或者-NR32-;
M1和M2相同或不相同,各自独立地选自O、S、-CR33R34-、-SiR35R36-或者-NR37-;
Z9–Z30相同或不相同,各自独立地选自-CR38-、-SiR39-、N;
R26–R39相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1–C30烷基、取代或未取代的C1–C30杂烷基、取代或未取代的C3–C30环烷基、取代或未取代的C3–C30杂环烷基、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基或者与相邻的原子键合成环;
A选自氢、氘、取代或未取代的C3–C30环烷基、取代或未取代的C3–C30杂环烷基、取代或未取代的C6–C30芳基、或取代或未取代的C5–C30杂芳基。
一些实施方式中,式(2)所示的第二主体化合物选自以下化学结构中的一种或多种:
/>
/>
/>
本发明还提供一种包括上述任意有机化合物中的一种或多种、或者上述主体材料中的一种或多种的有机层。
本发明还提供一种有机电致发光器件,其包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机层,可为底部或顶部发光器件结构,其有机层可为单层结构,也可为层合有两个或多个有机层的多层串联结构,有机层包括空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,可使用制备有机电致发光器件的常见方法和材料来制备,采用化合物作为有机电致发光器件的有机层。
本发明的有机电致发光器件中,第一电极为阳极层,阳极材料可以是具有大功函数的材料使空穴顺利地注入有机层,可以是金属、金属氧化物、金属和氧化物的组合、导电聚合物等,金属氧化物例如可以是氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明的有机电致发光器件中,第二电极为阴极层,阴极材料可以是具有小功函数的材料,使电子顺利地注入有机层;可以是金属或多层结构材料,金属可以是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡和铅或其合金,优选镁和银。
本发明的有机电致发光器件中,空穴注入层的材料优选最高占据分子轨道(HOMO)介于阳极材料的功函数与周围有机层的HOMO之间的材料,在低电压下从阳极接收空穴。
本发明的有机电致发光器件中,空穴传输层的材料对空穴具有高迁移率,适合作为接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,包括但不限于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
本发明的有机电致发光器件中,本发明提供的有机化合物可应用于器件的发光层。
本发明的有机电致发光器件中,电子传输层的材料对电子具有高迁移率,适合作为有利地接收来自阴极的电子并将电子传输至发光层的材料。
本发明的有机电致发光器件中,覆盖层的材料通常具有高折射率,有助于提高有机电致发光器件的光效率,特别是外部发光效率。
本发明还提供一种显示或照明装置,包括上述任意有机电致发光器件。
以下通过特定的具体实例说明本发明的实施方式。
合成实施例
上述式(1)所示的有机化合物合成可以使用已知方法进行,例如使用镍、钯等过渡金属的交叉偶合反应,其他合成方法例如使用镁或锌等过渡金属的C-C、C-N偶联生成反应等,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki、Buchwald反应,本发明以下实施例举例说明,但并不限于这些实施例举例的化合物和合成方法。
以下实施例中初始原料和溶剂和一些常用的OLED中间体类等产品购于国内的OLED中间体厂商,各种钯催化剂、配体等购于sigma-Aldrich公司,1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定,HPLC数据使用岛津LC-20AD高效液相仪来测定。
以下实施例中使用物质为:
合成实施例1
化合物1的合成
1)中间体1-1的合成
在氩气氛围下,向反应容器中加入化合物1-A 27.5克(100mmol),化合物1-B 28.5克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),三叔丁基膦四氟硼酸盐580毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到38.8克化合物1-1,HPLC纯度99.9%,收率81%。LCMS:M/Z 479.16(M+);1HNMR(400MHz,DMSO-d6)δ6.53(dd,1H),6.96-7.06(m,3H),7.14(dd,1H),7.19(dd,1H),7.36-7.56(m,4H),7.60-7.70(m,2H),7.72-7.84(m,4H),8.24(dd,1H),8.25-8.34(m,2H),9.77(s,2H).
2)化合物1的合成
在氩气氛围下,向反应容器中加入化合物1-1 48.0克(100mmol)、化合物1-C 38.8克(100mmol)、碘化亚铜190毫克(1mmol)、BPPO 392毫克(1mmol)和K3PO4 42.5克(200mmol)。加入DMSO 300mL。混合物在90℃下搅拌24小时后,降至室温,用500mL乙酸乙酯稀释混合物500ml水洗涤有机层三次,有机层减压浓缩。得到粗品通过硅胶快速色谱法纯化(乙酸乙酯/石油醚=1:100),获得产品化合物1,HPLC纯度99.9%,收率70%。LC MS:M/Z 705.24(M+);1HNMR(400MHz,DMSO-d6)δ6.93(dd,1H),7.10-7.25(m,8H),7.35(dd,1H),7.38-7.54(m,7H),7.59-7.70(m,7H),7.72-7.84(m,4H),8.21-8.31(m,2H),8.31(dd,1H).
实施例2
化合物29的合成
1)中间体29-1的合成
在氩气氛围下,向反应容器中加入化合物29-A 34.2克(100mmol),化合物1-B27.2克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),三叔丁基膦四氟硼酸盐580毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/石油醚=1:100),得到47.5克化合物29-1,HPLC纯度99.9%,收率87%。LC MS:M/Z 546.05(M+)。
1HNMR(400MHz,DMSO-d6)δ6.98(dd,1H),7.12(dd,1H),7.33(d,1H),7.37-7.46(m,1H),7.46-7.54(m,3H),7.60-7.70(m,2H),7.72-7.84(m,4H),8.03(d,1H),8.09(dd,1H),8.27(m,1H),8.30-8.37(m,1H).
2)化合物29的合成
氩气氛围下,反应器中加入化合物29-1 54.5g(100mmol)、化合物29-C 33.9g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到57.2g的化合物29,收率87%,HPLC纯度99.9%。LC MS:M/Z657.13(M+);1HNMR(400MHz,DMSO-d6)δ6.95(dd,1H),7.33(d,1H),7.37-7.46(m,1H),7.46-7.54(m,4H),7.60-7.70(m,2H),7.72-7.84(m,4H),7.90(dd,1H),7.98(m,3H),8.03(d,1H),8.21(dd,1H),8.27(m,1H),8.45(dd,3H).
实施例3
化合物51的合成
除了起始原料更换为51-A和51-C以外,其他与实施例2相同。LC MS:M/Z 601.18(M+)。合成总收率:64%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.06(d,2H),7.17(dd,2H),7.28-7.37(m,2H),7.37-7.46(m,1H),7.49(m,1H),7.60-7.69(m,2H),7.69-7.84(m,10H),7.92(dd,2H),8.27(dt,1H).
实施例4
化合物75的合成
除了起始原料更换为75-A、75-B和75-C以外,其他与实施例2相同。LC MS:M/Z652.19(M+)。合成总收率:65%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.95(dd,1H),7.13(d,1H),7.33(m,3H),7.44-7.55(m,6H),7.72(dt,4H),7.90(dd,1H),8.02(dd,3H),8.21(dd,1H),8.30-8.40(m,4H).
实施例5
化合物97的合成
除了起始原料更换为97-A、97-B和97-C以外,其他与实施例2相同。LC MS:M/Z578.17(M+)。合成总收率:66%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.30(d,4H),6.95(dd,1H),7.47-7.56(m,3H),7.69-7.82(m,4H),7.82-7.91(m,2H),7.90(dd,1H),8.21(dd,1H),8.23-8.35(m,4H),8.80(d,1H),9.51(d,1H).
实施例6
化合物121的合成
1)中间体121-1的合成
在氩气氛围下,向反应容器中加入化合物121-A 31.2克(100mmol),化合物1-B27.2克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),三叔丁基膦四氟硼酸盐580毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/石油醚=1:100),得到41.8克化合物121-1,HPLC纯度99.9%,收率81%。LC MS:M/Z 515.10(M+)。1HNMR(400MHz,DMSO-d6)δ7.01(dd,1H),7.14(dd,1H),7.30-7.54(m,6H),7.60-7.70(m,3H),7.72-7.84(m,5H),8.21-8.31(m,2H),8.31(dd,1H).
2)化合物121的合成
在氩气氛围下,向反应容器中加入化合物121-1 51.6克(100mmol),化合物121-C42.7克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),三叔丁基膦四氟硼酸盐580毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/石油醚=1:100),得到70.4克化合物121,HPLC纯度99.9%,收率81%。LC MS:M/Z 869.32(M+)。1HNMR(400MHz,DMSO-d6)δ6.91(dd,1H),7.00(m,2H),7.04-7.11(m,4H),7.14(dd,1H),7.20-7.54(m,17H),7.58(dd,1H),7.61-7.70(m,2H),7.67-7.77(m,2H),7.73-7.84(m,4H,),8.21-8.34(m,5H).
实施例7
化合物140的合成
除了起始原料更换为140-B和140-C以外,其他与实施例6相同。LC MS:M/Z 908.33(M+)。合成总收率:64%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.80(dd,1H),7.00(m,2H),7.08(m,4H),7.14(m,2H),7.18-7.31(m,10H),7.31-7.44(m,5H),7.44-7.66(m,9H),7.70(dd,1H),7.87(dd,1H),8.21-8.30(m,2H),8.26-8.35(m,3H).
实施例8
化合物150的合成
除了起始原料更换为150-A、1-B和150-C以外,其他与实施例2相同。LC MS:M/Z735.32(M+)。合成总收率:60%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ1.67-1.73(m,18H),6.92(t,2H),7.10-7.19(m,4H),7.26(dd,1H),7.31(d,1H),7.37-7.48(m,1H),7.49(dt,1H),7.54(ddd,3H),7.60-7.70(m,3H),7.72-7.84(m,4H),8.21-8.31(m,2H),8.31(dd,1H).
实施例9
化合物172的合成
除了起始原料更换为51-A、75-B和172-C以外,其他与实施例2相同。LC MS:M/Z606.18(M+)。合成总收率:60%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.17(dd,2H),7.44-7.55(m,6H),7.68-7.78(m,4H),7.89-7.95(m,4H),8.26(m,2H),8.30-8.40(m,4H).
实施例10
化合物190的合成
除了起始原料更换为140-A、97-B和190-C以外,其他与实施例6相同。LC MS:M/Z677.26(M+)。合成总收率:63%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.80(dd,1H),6.91-7.18(m,12H),7.24(m,4H),7.42-7.56(m,5H),7.57-7.66(m,2H),7.78(dd,2H),7.82-7.91(m,3H),8.25-8.35(m,2H).
实施例11
化合物H-4的合成
除了起始原料更换为H-4-A、H-4-B和H-4-C以外,其他与实施例1相同。LC MS:M/Z515.15(M+)。合成总收率:50%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.82(m,2H),6.90-6.99(m,3H),7.10-7.18(m,2H),7.19(m,2H),7.25(dd,1H),7.31(m,1H),7.35(dd,1H),7.45(m,2H),7.51-7.57(m,2H),7.66(dd,1H),7.86(d,1H),7.98(dd,1H),8.24(dd,1H,),8.31(dd,1H).
实施例12
化合物H-19的合成
/>
除了起始原料更换为H-19-A、H-19-B和H-19-C以外,其他与实施例1相同。LC MS:M/Z591.18(M+)。合成总收率:61%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.02(dd,2H),7.17(m,2H),7.21(dd,2H),7.35(dd,2H),7.38-7.51(m,6H),7.52-7.69(m,5H),7.85(dd,2H),7.91(d,2H),8.57(d,2H).
实施例13
化合物H-30的合成
除了起始原料更换为75-A、H-30-B和75-C以外,其他与实施例2相同。LC MS:M/Z573.17(M+)。合成总收率:59%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.95(dd,1H),7.13(d,1H),7.17-7.26(m,2H),7.27-7.48(m,7H),7.69-7.83(m,5H),7.89(m,2H),7.99-8.09(m,4H),8.21(dd,1H).
实施例14
化合物H-38的合成
除了起始原料更换为H-38-A、H-38-B和H-38-C以外,其他与实施例2相同。LC MS:M/Z665.31(M+)。合成总收率:59%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ1.67-1.73(s,18H),6.95(dd,1H),7.24(m,3H),7.35(m,1H),7.40-7.49(m,7H),7.49(t,1H),7.49-7.56(m,2H),7.63-7.70(m,2H),7.89(m,2H),8.00-8.06(m,1H),8.21(dd,1H).
实施例15
化合物H-43的合成
除了起始原料更换为51-A、H-43-B和H-43-C以外,其他与实施例1相同。LC MS:M/Z673.25(M+)。合成总收率:61%;HPLC纯度:99.9%。
1HNMR(400MHz,DMSO-d6)δ6.59(d,2H),6.95(dd,2H),7.17(t,2H),7.36(dd,1H),7.44-7.51(m,4H),7.52-7.68(m,8H),7.83(t,1H),7.86-7.95(m,6H),8.03(m,3H),8.21(dd,2H).
实施例16
化合物H-46的合成
除了起始原料更换为51-A、H-46-B和H-46-C以外,其他与实施例2相同。LC MS:M/Z723.27(M+)。合成总收率:57%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.59(dd,2H),7.06-7.14(m,2H),7.17(t,2H),7.44-7.51(m,4H),7.52-7.78(m,9H),7.81-7.97(m,9H),8.12(dd,2H),8.21(dd,1H),8.74-8.80(m,1H),9.05(d,1H)
实施例17
化合物H-69的合成
除了起始原料更换为H-19-B和H-69-C以外,其他与实施例6相同。LC MS:M/Z675.27(M+)。合成总收率:59%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.96-7.04(m,2H),7.08(m,4H),7.14(dd,1H),7.20-7.30(m,6H),7.29(dd,1H),7.31-7.43(m,3H),7.44-7.51(m,2H),7.53-7.71(m,11H),8.21-8.27(m,2H),8.31(dd,1H).
实施例18
化合物H-76的合成
除了起始原料更换为H-76-A、H-19-B和H-76-C以外,其他与实施例2相同。LC MS:M/Z529.13(M+)。合成总收率:58%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.92(m,3H),6.97(d,1H,),7.08(m,3H),7.14(dd,1H),7.28(d,1H),7.38(m,3H),7.44-7.51(m,2H),7.52-7.67(m,3H),8.24(dd,1H),8.31(dd,1H).
实施例19
化合物H-81的合成
除了起始原料更换为51-A、H-19-B和H-81-C以外,其他与实施例2相同。LC MS:M/Z475.13(M+)。合成总收率:62%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.17(dd,2H),7.44-7.67(m,7H),7.70-7.78(m,4H),7.92(dd,2H),8.26(dd,2H).
实施例20
化合物H-90的合成
除了起始原料更换为51-A、H-19-B和H-90-C以外,其他与实施例2相同。LC MS:M/Z625.23(M+)。合成总收率:59%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.14-7.27(m,4H),7.32-7.40(m,4H),7.44-7.53(m,6H),7.53-7.67(m,7H),7.75(dd,2H),7.85(dd,2H),7.92(dd,2H).
实施例21
化合物E-3的合成
1)中间体E-3-1的合成
氩气氛围下,反应器中加入E-3-A 31.5g(100mmol)、E-3-B 12.2g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到28.2g的化合物E-3-1,收率75%,HPLC纯度99.5%。LC MS:M/Z 311.01(M+)。1HNMR(400MHz,DMSO-d6)δ7.44-7.55(m,6H,),8.30-8.40(m,4H,)
2)化合物E-3的合成
氩气氛围下,反应器中加入E-3-1 31.2g(100mmol)、E-3-C 30.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到39.0g的化合物E-3,收率80%,HPLC纯度99.9%。LC MS:M/Z 487.18(M+)。1HNMR(400MHz,DMSO-d6)δ7.37-7.45(m,2H),7.45-7.59(m,8H),7.72-7.78(m,1H),7.78-7.85(m,1H),8.02-8.10(m,1H),8.24-8.31(m,2H),8.31-8.40(m,4H),8.69-8.76(m,1H),8.76-8.82(m,1H)
实施例22
化合物E-16的合成
除了起始原料更换为E-16-B和E-16-C以外,其他与实施例21相同。LC MS:M/Z576.66(M+)。合成总收率:51%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.45-7.68(m,9H),7.81-7.87(m,1H),7.96-8.05(m,1H),8.05-8.16(m,3H),8.12-8.23(m,4H),8.30-8.40(m,2H),8.45-8.53(m,1H),8.93(d,1H),9.09(t,1H),9.76(d,1H).
实施例23
化合物E-25的合成
除了起始原料更换为E-25-B和E-25-C以外,其他与实施例21相同。LC MS:M/Z550.22(M+)。合成总收率:44%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.19(m,1H),7.32-7.43(m,2H),7.44-7.57(m,7H),7.53-7.66(m,6H),7.69-7.77(m,3H),7.88-7.97(m,3H),8.17-8.23(m,1H),8.30-8.40(m,3H).
实施例24
化合物E-35的合成
除了起始原料更换为E-35-A、E-35-B和E-36-C以外,其他与实施例21相同。LC MS:M/Z550.22(M+)。合成总收率:38%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.31(m,3H),7.39-7.57(m,8H),7.70(dd,2H),7.76(dd,2H),7.88-7.96(m,3H),7.96-8.02(m,3H),8.49(dd,1H),9.09(t,1H)
实施例25
化合物E-47的合成
除了起始原料更换为E-48-B和E-48-C以外,其他与实施例21相同。LC MS:M/Z667.27(M+)。合成总收率:45%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ1.69(s,6H),7.28(m,1H),7.35(m,3H),7.42-7.57(m,8H),7.57-7.65(m,1H),7.61-7.71(m,2H),7.78-7.84(m,1H),7.85-7.91(m,1H),7.93-8.01(m,1H),8.08(dd,2H),8.30-8.40(m,2H),8.45-8.53(m,2H),8.56(dd,1H),9.09(dd,2H).
实施例26
化合物E-59的合成
/>
除了起始原料更换为E-59-A、E-59-B和E-59-C以外,其他与实施例21相同。LC MS:M/Z627.27(M+)。合成总收率:45%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ1.69(s,6H),7.31-7.77(m,19H),7.85-7.97(m,3H),7.95-8.02(m,2H),8.10-8.17(m,1H),8.46-8.54(m,1H),9.07(t,1H).
实施例27
化合物E-67的合成
除了起始原料更换为E-35-A、E-67-B和E-67-C以外,其他与实施例21相同。LC MS:M/Z656.09(M+)。合成总收率:40%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.35(m,2H),7.45(m,2H),7.49-7.59(m,4H),7.81-7.87(m,1H),7.88(dd,2H),7.97-8.06(m,2H),8.02-8.14(m,4H),8.16(dd,1H),8.93(d,1H),9.76(d,1H).
实施例28
化合物E-76的合成
氩气氛围下,反应器中加入E-35-A 31.8g(100mmol)、E-16-B 51.6g(300mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到36.8g的化合物E-76,收率80%,HPLC纯度99.9%。LC MS:M/Z 459.17(M+)。1HNMR(400MHz,DMSO-d6)δ7.56-7.68(m,6H),7.95-8.05(m,3H),8.08(d,3H),8.11-8.21(m,3H),8.45-8.53(m,3H),9.09(t,3H).
实施例29
化合物E-87的合成
除了起始原料更换为E-59-A、E-35-B和E-87-C以外,其他与实施例21相同。LC MS:M/Z601.22(M+)。合成总收率:46%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ7.31(m,1H),7.35-7.62(m,9H),7.63-7.82(m,8H),7.88-7.95(m,3H),7.95-8.05(m,1H),8.01-8.08(m,1H),8.26-8.34(m,1H),8.46-8.54(m,1H),8.70(t,1H),8.95(m,1H).
实施例30
化合物E-96的合成
除了起始原料更换为E-35-A、E-25-B和E-96-C以外,其他与实施例21相同。LC MS:M/Z567.19(M+)。合成总收率:41%;HPLC纯度:99.9%。1HNMR(400MHz,DMSO-d6)δ6.78-6.86(m,2H),6.89-6.99(m,3H),7.08(dd,1H),7.34-7.43(m,2H),7.43-7.53(m,4H),7.54-7.61(m,4H),7.64(dd,1H),7.69-7.77(m,4H),7.88-7.96(m,4H).
器件实施例1:单主体材料有机电致发光器件的制备
有机电致发光器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的化合物):RD(Ir配合物)=94:6(40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。有机电致发光器件的制造方法如下:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN,40nm的TAPC和10nm的TCTA。
(3)在上述TCTA上蒸镀厚度为40nm的发光层(EML),其中本发明化合物1与RD的质量比为94:6。
(4)在上述发光层上蒸镀厚度为30nm的电子传输层(ETL)材料。
(5)在上述电子传输层上蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后在上述电子注入层上蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装。
器件实施例2-10
除了在形成发光层时,分别以化合物29、51、75、97、121、140、150、172、和190替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
器件对比例1-2
除了在形成发光层时,分别以化合物RH-01、化合物RH-02替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
以上制得的有机电致发光器件通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率,使用配备电源和光电二极管作为检测单元的Polaronix(McScienceCo.)寿命测量系统得到黑暗条件下的器件寿命。每一组器件实施例和器件对比例1均与器件对比例2的器件在同一批次中产出并测试,如表1所示。
表1:器件实施例1-10及器件对比例1-2的测试结果
根据表1的结果可知,作发光器件的发光层时,器件实施例1-10所使用的化合物与器件对比例1-2中使用的化合物形成的器件相比,发光效率均有所提高(最高达到25%),寿命提高高达40%以上。据此,上述实施例和对比例中的器件结构除了发光层不同外,其它均一致,基于RH-01和RH-02的器件性能为参考,包含本发明的有机化合物的器件电流效率有显著提升,同时其寿命也有所提升。
器件实施例11:多主体材料有机电致发光器件的制备
器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的主体材料:RD(Ir配合物)(40nm)=98:2/ETL(30nm)/LiF(1nm)/Al(80nm),有机电致发光器件的制造方法:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN、40nm的TAPC和10nm的TCTA。
(3)蒸镀厚度为40nm的发光层(EML)(其中,本发明的主体材料与RD的质量比为98:2),其中在该主体材料中,第一主体化合物H-4与第二主体化合物E-3的质量比为2:3。
(4)蒸镀厚度为30nm的电子传输层(ETL)材料。
(5)蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装。
器件实施例12-20
除了在形成发光层时,分别以化合物组合物H-19和E-16、H-30和E-25、H-38和E-35、H-43和E-47、H-46和E-59、H-69和E-67、H-76和E-76、H-81和E-87、H-90和E-965替代化合物H-4和E-3外,采用与器件实施例11相同的方法制作有机电致发光器件。
器件对比例3-4
除了在形成发光层时,分别以化合物CBP、化合物Ref1和Ref2替代化合物H-4和E-3以外,采用与器件实施例11相同的方法制作有机电致发光器件。
以上制得的有机电致发光器件通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率,使用配备电源和光电二极管作为检测单元的Polaronix(McScienceCo.)寿命测量系统得到黑暗条件下的器件寿命,每一组器件实施例和器件对比例3和4的器件在同一批次中产出并测试,如表2所示。
表2:器件实施例11-20及器件对比例3-4的测试结果
根据表2的结果可知,作发光器件的发光层时,器件实施例11-20所使用的化合物与器件对比例1-2中使用的化合物形成的器件相比,电压均有所降低,发光效率均有所提高(最高达到20%),寿命提高高达40%以上。据此,上述实施例和对比例中的器件结构除了发光层不同外,其它均一致,基于Ref1和Ref2的器件性能为参考,包含本发明的有机化合物的器件电流效率有显著提升,同时其寿命也有所提升。
以上,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (7)
1.有机化合物,其特征在于,选自以下化学结构中的一种:
2.有机化合物,选自以下化学结构中的一种:
3.一种主体材料,所述主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物选自权利要求1或2所述有机化合物中的一种或多种,所述第二主体化合物选自以下化学结构中的一种:
4.权利要求1或2所述有机化合物、或者权利要求3所述主体材料在有机电致发光器件中的应用。
5.一种有机层,包括权利要求1或2所述有机化合物中的一种或多种、或者权利要求3所述主体材料中的一种或多种。
6.一种有机电致发光器件,其包括第一电极、第二电极和权利要求5所述的有机层,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一种。
7.一种显示或照明装置,其包括权利要求6所述的有机电致发光器件。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210921528.7A CN115109065B (zh) | 2022-08-02 | 2022-08-02 | 有机化合物、主体材料和有机电致发光器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210921528.7A CN115109065B (zh) | 2022-08-02 | 2022-08-02 | 有机化合物、主体材料和有机电致发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115109065A CN115109065A (zh) | 2022-09-27 |
CN115109065B true CN115109065B (zh) | 2024-01-26 |
Family
ID=83334009
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210921528.7A Active CN115109065B (zh) | 2022-08-02 | 2022-08-02 | 有机化合物、主体材料和有机电致发光器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115109065B (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110804054A (zh) * | 2018-08-06 | 2020-02-18 | 北京鼎材科技有限公司 | 一种化合物及其应用 |
CN114195701A (zh) * | 2021-12-30 | 2022-03-18 | 上海钥熠电子科技有限公司 | 一种稠环芳胺化合物及其在有机电致发光器件中的应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018182259A1 (ko) * | 2017-03-30 | 2018-10-04 | 주식회사 엘지화학 | 유기 발광 소자 |
KR20210083464A (ko) * | 2019-12-26 | 2021-07-07 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
CN114105997B (zh) * | 2021-01-28 | 2023-05-19 | 陕西莱特光电材料股份有限公司 | 一种含氮化合物及包含其的电子元件和电子装置 |
CN114805386B (zh) * | 2022-06-08 | 2024-02-09 | 上海钥熠电子科技有限公司 | 有机化合物、主体材料和有机光电器件 |
-
2022
- 2022-08-02 CN CN202210921528.7A patent/CN115109065B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110804054A (zh) * | 2018-08-06 | 2020-02-18 | 北京鼎材科技有限公司 | 一种化合物及其应用 |
CN114195701A (zh) * | 2021-12-30 | 2022-03-18 | 上海钥熠电子科技有限公司 | 一种稠环芳胺化合物及其在有机电致发光器件中的应用 |
Also Published As
Publication number | Publication date |
---|---|
CN115109065A (zh) | 2022-09-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101412437B1 (ko) | 신규한 화합물 및 이를 이용한 유기 전자 소자 | |
KR102192691B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 | |
KR102172580B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
CN114805386B (zh) | 有机化合物、主体材料和有机光电器件 | |
KR20180063709A (ko) | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 | |
CN114835590A (zh) | 一种有机化合物及其在有机光电器件的应用 | |
KR20210089294A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20190007257A (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
CN114890935A (zh) | 一种化合物及其在有机光电器件的应用 | |
CN115448932A (zh) | 一种化合物、有机光电器件及显示或照明装置 | |
KR102316570B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20200052236A (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
KR102107086B1 (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
KR102120917B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR102120916B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 | |
KR20180137332A (ko) | 안트라센 유도체 및 이를 포함하는 유기 발광 소자 | |
KR20210048018A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20200068568A (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
CN115304498A (zh) | 一种化合物及其在有机光电器件中的应用 | |
CN115109065B (zh) | 有机化合物、主体材料和有机电致发光器件 | |
CN114335399A (zh) | 有机电致发光器件及包括其的电子装置 | |
KR20190034782A (ko) | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 | |
KR102201551B1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20210010407A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20210070442A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
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 | ||
CB03 | Change of inventor or designer information | ||
CB03 | Change of inventor or designer information |
Inventor after: Wang Xiangcheng Inventor after: He Mu Inventor before: Wang Peng Inventor before: Wang Xiangcheng Inventor before: He Mu |
|
GR01 | Patent grant | ||
GR01 | Patent grant |