CN116332978B - Organic compound, preparation method thereof and organic electroluminescent device comprising organic compound - Google Patents
Organic compound, preparation method thereof and organic electroluminescent device comprising organic compound Download PDFInfo
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- CN116332978B CN116332978B CN202310620465.6A CN202310620465A CN116332978B CN 116332978 B CN116332978 B CN 116332978B CN 202310620465 A CN202310620465 A CN 202310620465A CN 116332978 B CN116332978 B CN 116332978B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 diethylphenyl Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 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 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 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 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 210000003936 merozoite Anatomy 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 69
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 238000013461 design Methods 0.000 abstract description 6
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 238000013508 migration Methods 0.000 abstract description 3
- 230000005281 excited state Effects 0.000 abstract description 2
- 230000005283 ground state Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 117
- 238000006243 chemical reaction Methods 0.000 description 105
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 86
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
- 238000001035 drying Methods 0.000 description 42
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000003208 petroleum Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 37
- 239000002994 raw material Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 21
- 238000002347 injection Methods 0.000 description 21
- 239000007924 injection Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- 239000012295 chemical reaction liquid Substances 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000012790 confirmation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000009987 spinning Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940125898 compound 5 Drugs 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite Substances 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-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
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 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
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical class N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 240000003186 Stachytarpheta cayennensis Species 0.000 description 1
- 235000009233 Stachytarpheta cayennensis Nutrition 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
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 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
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 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
- 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000010792 warming Methods 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
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- 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
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- 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
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an organic compound, a preparation method thereof and an organic electroluminescent device comprising the same; the organic compound has a structure shown in a formula I. According to the invention, the organic compound introduces a more rigid cycloalkyl structure on the basis of a mother nucleus through a specific molecular structure design, so that the carrier transmission and migration are facilitated; meanwhile, a rigid molecular group with high steric hindrance is introduced into the molecular structure, so that the gap between a singlet state and a triplet state can be reduced to the greatest extent; the multi-ring conjugated rigid structure effectively inhibits vibration of a molecular ground state and an excited state, and has a narrow emission band; as the doping material of the luminous layer of the OLED device, the luminous efficiency and the luminous service life of the device can be effectively improved, and industrialization can be realized.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to an organic compound, a preparation method thereof and an organic electroluminescent device comprising the same.
Background
Organic Light Emitting Diodes (OLEDs) are increasingly coming into the field of view as a new and promising display technology. An OLED is an electroluminescent device formed from a multi-layer organic thin film structure.
The core of the OLED display technology is an organic luminescent material, and the full color gamut is realized based on the mixture of a red light material, a green light material and a blue light material. The development of novel luminescent materials is a source force for promoting the continuous progress of electroluminescent technology and is also a research hotspot of the organic electroluminescent industry. The development of the novel blue light organic electroluminescent material is expected to realize high luminous efficiency and better service life of the device, and meanwhile, the blue light luminescent material with narrow half-peak width and high color purity is also the key point for developing the blue light luminescent material.
At present, multiple vibration effect (MR effect) is adopted, and vibration opposite to hetero atoms such as boron and nitrogen oxygen is utilized to construct a polycyclic aromatic compound formed by condensing a plurality of aromatic rings by the hetero atoms such as boron atoms and nitrogen oxygen, namely, a special rigid material system containing the hetero atoms such as boron atoms and nitrogen oxygen is prepared. Such fluorescent molecules have high radiative transition rates, narrow half-widths, high color purity, but do not perform particularly well in terms of device lifetime and luminous efficiency, and the industrialization process of this technology still faces a number of key issues.
For example CN115651004a discloses an organic compound containing nitrogen heteroboron and its use; the organic compound is convenient to improve the stability of material molecules and the conductivity of the material by substituting an aromatic ring on a functional group with aza-boron, and is used as a blue light fluorescent main material to prepare a light-emitting device, so that the service life of the device is prolonged. On the one hand, the compound is used as a main body material, and on the other hand, the organic compound has limited improvement on the service life of the device.
As another example, CN114685538A discloses a boron-nitrogen compound and an organic light-emitting device prepared from the same; the boron-nitrogen compound molecular structure contains an aromatic ring and a boron-nitrogen structure and is used as a doping material of the light-emitting layer; however, the lifetime of the OLED device including the same is low.
Therefore, development of a luminescent material which has high luminous efficiency and long luminous life and can realize industrialization is a problem to be solved in the art.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide an organic compound, a preparation method thereof and an organic electroluminescent device comprising the same. The organic compound is designed by a specific molecular structure, is used as a doping material of a light-emitting layer of the OLED device, can effectively improve the light-emitting efficiency and the light-emitting service life of the device, and can realize industrialization.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic compound having a structure according to formula I:
a formula I;
wherein ring Ar 1 Ring Ar 2 Each independently selected from any one of the following structures:
、、。
R 11 、R 12 、R 13 each independently selected from any one of hydrogen, deuterium, nitrile groups, halogen groups, substituted or unsubstituted C1-C20 straight or branched chain alkyl groups, substituted or unsubstituted C1-C20 straight or branched chain alkoxy groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C6-C30 heteroaryl groups, wherein heteroatoms in the C6-C30 heteroaryl groups contain at least one of O, S, N, si, se.
m 1 An integer of 0 to 4, for example, 0, 1, 2, 3, 4; m is m 2 An integer of 0 to 5, for example, 0, 1, 2, 3, 4, 5; m is m 3 An integer of 0 to 3, for example, 0, 1, 2, 3, etc.
The dashed lines represent the merozoic chemical bonds, and their optional merozoic positions.
In the present invention,the middle horizontal line represents a single bond.
The R is 1 、R 2 Each independently selected from any one of the following structures:
、、、、。
wherein R is 14 、R 15 、R 16 、R 17 Each independently selected from any one of hydrogen, deuterium, nitrile groups, halogen groups, substituted or unsubstituted C1-C20 straight or branched chain alkyl groups, substituted or unsubstituted C1-C20 straight or branched chain alkoxy groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C6-C30 heteroaryl groups, wherein heteroatoms in the C6-C30 heteroaryl groups contain at least one of O, S, N, si, se.
X is selected from O, S, CR 21 R 22 Any of which, R 21 、R 22 Selected from methyl groups.
m 4 An integer of 0 to 5, for example, 0, 1, 2, 3, 4, 5; m is m 5 An integer of 0 to 9, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9; m is m 6 An integer of 0 to 7, for example, 0, 1, 2, 3, 4, 5, 6, 7; m is m 7 Is an integer of 0 to 4, and may be, for example, 0, 1, 2, 3, 4.
". Times" indicates a ligation site.
R 3 Selected from hydrogen, deuterium, nitrile groups, halogen groups, substituted or unsubstituted C1-C20 straight or branched alkyl groupsAny one of chain alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C6-C30 heteroaryl, wherein hetero atoms in the C6-C30 heteroaryl at least contain one of O, S, N, si, se.
The substituent group is selected from any one of deuterium, nitrile group, halogen group, substituted or unsubstituted C1-C20 straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C20 straight-chain or branched-chain alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C6-C30 heteroaryl, wherein hetero atoms in the C6-C30 heteroaryl at least contain one of O, S, N, si, se.
The ring Ar 1 、Ar 2 At least one group beingThe method comprises the steps of carrying out a first treatment on the surface of the And/or, the R 1 、R 2 At least one group of +.>。
According to the invention, the organic compound is provided with a high conjugated electron distribution system by introducing a cycloalkyl structure on the basis of a mother nucleus through a specific molecular structure design, so that molecules are effectively and orderly stacked, and the optimal carrier transmission and migration are exerted under a certain electric field; meanwhile, some rigid and high-steric-hindrance molecular groups are synthesized in a molecular structure, so that the molecules combine long-range interaction and delocalization in a quite unique mode, the effect of short-distance high radiation attenuation rate is caused, and the gap between a singlet state and a triplet state can be reduced to the greatest extent by charge density reorganization; the multi-ring conjugated rigid structure effectively inhibits the vibration of the molecular ground state and the excited state, and the reaction is carried out in a narrower emission band; as the doping material of the luminous layer of the OLED device, the luminous efficiency and the luminous service life of the device can be effectively improved, and industrialization can be realized.
In the present invention, the C1-C20 may be, for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.
The C6-C30 may be, for example, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.
The following Wen Ruyou is the same expression and meaning.
Preferably, said R 3 At least one selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, phenyl, tolyl, xylyl, diethylphenyl, isopropylphenyl, 1, 3-diisopropylphenyl, tert-pentylphenyl, 1, 3-di-tert-butylphenyl, naphthyl, anthracenyl or phenanthryl.
Preferably, said R 11 、R 12 、R 13 、R 14 、R 15 Each independently selected from any one of the following structures:
。
". Times" indicates a ligation site.
Preferably, said R 16 、R 17 Each independently selected from any one of the following structures:
。
preferably, the organic compound has any one of the structures shown below:
、、、、、、、、。
The ring Ar 1 Ring Ar 2 、R 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
Preferably, the organic compound has any one of the structures shown below:
、、、、、、、、the method comprises the steps of carrying out a first treatment on the surface of the The R is 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
Preferably, the organic compound has any one of the structures shown below:
、；
the R is 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
In the present invention, ring Ar is further preferable 1 Ring Ar 2 、R 1 、R 2 、R 3 The inclusion of a C1-C6 straight or branched alkyl group is advantageous in improving color purity.
In the present invention, the "substitution" means substitution of a hydrogen atom with at least one substituent, which illustratively includes, but is not limited to: deuterium, nitrile, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, pyridyl, bipyridyl, dibenzocarbazolyl, benzothienyl, dibenzothienyl, dibenzofuranyl, and the like.
Preferably, the organic compound is selected from any one of the following compounds 1 to 174:
。
in a second aspect, the present invention provides a method for producing an organic compound according to the first aspect, the synthetic route of which is as follows:
。
in the invention, when the intermediate 1 reacts with the raw material C, as the triarylamine group carried by the intermediate 1 is larger, the steric hindrance of chlorine ortho to the triarylamine group is larger when the intermediate reacts with the larger group, the intermediate C is influenced by the steric hindrance, the raw material C firstly reacts with the chlorine in the meta position of the three-way amino group, the ortho chlorine hardly reacts or the yield is extremely low, and impurities can be removed in the subsequent process.
Illustratively, the specific preparation method of the organic compound comprises:
synthesis of intermediate 1: raw material B (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then adding the raw materials A (1.0 eq) and Pd respectively 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq), heating to 90 ℃ for reaction for 16 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily substance, adding methanol, stirring and gradually separating out the product, namely the intermediate 1.
Synthesis of intermediate 2: raw material C (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Intermediate 1 (1.1 eq) and Pd were added separately 2 (dba) 3 （0.03eq）、P(t-Bu) 3 (0.2 eq), heating to 110 ℃ for reaction for 24 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:2, pouring out all product points, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring to gradually precipitate solid, and drying to obtain intermediate 2.
Synthesis of intermediate 3: intermediate 2 (1.0 eq) was dissolved in dichloromethane, cooled to 0 ℃, boron tribromide (5.0 eq) was added, after 4 hours of reaction, the reaction was stopped by adding water, the organic phase was retained by separation, dried over anhydrous magnesium sulfate, concentrated, purified by column chromatography, all product spots were washed out with dichloromethane, and spun-dried to give intermediate 3.
Synthesis of intermediate 4: intermediate 3 (1.0 eq) was dissolved in dichloromethane, triethylamine (5.0 eq) was added, the temperature was lowered to-10 ℃, trifluoroacetic anhydride (3.0 eq) was added dropwise, and the reaction was carried out at room temperature for 4 hours. The reaction was quenched by addition of water, the organic phase was collected, dried over anhydrous sulfuric acid, concentrated under reduced pressure, and purified by column chromatography to afford intermediate 4.
Synthesis of intermediate 5: intermediate 4 (1.0 eq) was added to the reaction flask, followed by feed D (1.1 eq) and Pd (pph) 3 ) 4 (0.01 eq) and K 2 CO 3 (2.0 eq) and toluene was added: ethanol: water=2:1:1 mixed solvent liquid, and the temperature is raised to 90 ℃ under the protection of nitrogen gas for reaction for 16 hours. After the reaction was completed, the temperature was lowered to room temperature, the solution was separated, the organic layer was dried by spin-drying, and purified by column chromatography using methylene chloride: and (3) pouring out all product points from petroleum ether=1:4 mixed solvent liquid, spin-drying to obtain oily matter, and adding petroleum ether, stirring to separate out white solid, namely the intermediate 5.
Synthesis of the organic compound: intermediate 5 (1.0 eq) was dissolved in tert-butylbenzene and stirred for 15 minutes at-40℃under nitrogen. Tert-butyllithium (2.0 eq) was injected, then the temperature was raised to 60℃for 2 hours, then the reaction was evacuated to remove a small amount of n-pentane, the reaction was cooled to-40℃again, boron tribromide (2.0 eq) was added, and the mixture was stirred at room temperature for 30 minutes. Then the reaction solution was cooled to 0℃and DIPEA (5.0 eq) was added thereto and the reaction solution was slowly returned to room temperature, and the reaction solution was heated to 100℃for 2 hours and then cooled to room temperature. The reaction solution was washed with brine, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, half of the tert-butylbenzene was distilled off, and then methanol was added thereto and stirred to precipitate a large amount of yellow solid. The yellow solid was purified by column chromatography to remove the isomer compounds generated during the reaction, using methylene chloride: petroleum ether=1:6 mixed solvent solution washes out all product points to obtain the organic compound.
Or when R is 3 In the case of methyl, the synthetic route of the organic compound is as follows:
。
in the present invention, the raw materials B and C may be commercially available or prepared by themselves, and the synthetic route of the raw materials B and C includes, for example:
。
illustratively, the specific preparation method of the raw material B or the raw material C comprises the following steps:
scheme one:
synthesis of intermediate c1/c 2: raw material a (1.0 eq) was dissolved in tetrahydrofuran and added to a 10% aqueous sulfuric acid solution, stirred and heated to 50 ℃, and an aqueous sodium bromate (2.0 eq) solution was added dropwise for reaction for 4-5 hours. After the reaction, cooling, separating liquid, extracting once by tetrahydrofuran, combining organic layers, washing for 2 times, drying by anhydrous magnesium sulfate, purifying and removing the isomer compound generated in the reaction by column chromatography, and using dichloromethane: petroleum ether=1:4, all product points were flushed out, and collected and spin-dried to give an oil, intermediate c1/c2.
Synthesis of raw materials B1/B2/C1/C2: the starting material d-1 (1.0 eq) or the starting material d-2 (1.0 eq) was added to the reaction flask, and then t-Buona (2.0 eq) and anhydrous toluene were added and stirred under nitrogen for 30 minutes. Respectively adding intermediate c1 or intermediate c2 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purifying by column chromatography, flushing out all product points with dichloromethane and petroleum ether=1:4, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring to gradually precipitate product, and obtaining raw materials B1, B2, C1 or C2.
Scheme 2:
(a) Raw material e (1.0 eq) was dissolved in THF, naOH solution (6.0 eq) was added at room temperature and reacted for 5 hours at 50 ℃. TLC detection reaction was complete. The THF solvent was turned off, diluted with water and washed with ethyl acetate (ethyl acetate was discarded). Acidifying the water phase with hydrochloric acid to adjust pH=2, extracting the organic phase with ethyl acetate, washing with salt water, drying with magnesium sulfate, and spin-drying to obtain a product intermediate d1;
(b) Intermediate d1 (1.0 eq), copper powder (1.5 eq), and cuprous oxide (0.3 eq) were added sequentially to quinoline under nitrogen. The temperature is raised to 230 ℃ for reaction for 10min. After the reaction was completed, the reaction mixture was cooled to room temperature. The solution was poured into water, PH was adjusted to approximately 1 with hydrochloric acid, then extracted 3 times with methyl tert-butyl ether, the organic phases were combined, washed with water, dried and spun-dried. Purification by column (petroleum ether: ethyl acetate=1:1) gives product intermediate d2;
(c) Intermediate d2 (1.0 eq) was dissolved in t-butanol, triethylamine (1.1 eq) was added, and DPPA (1.1 eq) was added dropwise under nitrogen. After completion of the dropwise addition, the reaction was refluxed overnight (12 h). Cooling to room temperature after the reaction is finished, pouring the mixture into ice water and stirring the mixture for 30 minutes. Extracting the organic phase with ethyl acetate, washing with water, drying, spin drying, and purifying with column (petroleum ether to dichloromethane=10:1) to obtain product intermediate d3;
(d) Intermediate d3 (1.0 eq) was dissolved in DCM and a small amount of trifluoroacetic acid was added dropwise at room temperature, and stirred at room temperature for 1 hour after the addition. TLC detects the completion of the reaction of the starting materials, spin-dry the solvent. The residue was dissolved in DCM, washed 2 times with aqueous sodium hydroxide, brine, dried over magnesium sulfate and spun-dried to give product intermediate c3;
(e) The starting material d-3 (1.0 eq) or starting material d-4 (1.0 eq) was added to the reaction flask, and then t-Buona (2.0 eq) and anhydrous toluene were added and stirred under nitrogen for 30 minutes. Then respectively adding the intermediate c3 and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily matter, adding stone And stirring the oil ether to gradually precipitate a product, thus obtaining the raw material B3 or C3.
In addition, intermediate c3 (1.0 eq) was dissolved in acetonitrile, copper bromide (1.2 eq) was added and cooled to 0 ℃ under nitrogen. Tert-butyl nitrite (1.5 eq) was added dropwise. Naturally warming to room temperature and reacting overnight (12 h). Pouring into water, stirring, extracting organic phase with petroleum ether, washing with saline solution, drying, and spin drying. Purification by column (petroleum ether washing) gives starting material 1.
Raw material 1 (1.0 eq) was added to a reaction flask, followed by t-BuONa (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then respectively adding the intermediate c3 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1: and 4, pouring out all product points, collecting and spin-drying to obtain oily matters, and adding petroleum ether to stir and gradually separating out products to obtain a raw material 2.
In a third aspect, the present invention provides an organic electroluminescent device comprising an organic compound according to the first aspect.
In the invention, the organic electroluminescent device comprises a cathode, an organic film layer and an anode which are sequentially arranged; the organic thin film layer includes a light emitting layer; the material of the light emitting layer comprises the organic compound according to the first aspect.
In the present invention, the organic compound may be used as a doping material of the light emitting layer; the material of the light emitting layer may contain 1 to 5% by mass of a doping material, for example, 1%, 2%, 3%, 4%, 5% by mass, and the like.
In the present invention, the preparation method of the light emitting layer includes, but is not limited to, a vacuum evaporation method, a solution coating method, and the like; the solution coating method refers to spin coating, dip coating, blade coating, ink jet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
Preferably, the material of the light emitting layer further comprises a host material.
In the present invention, the host materials include, but are not limited to: condensed aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. In particular, the fused aromatic ring derivatives include, but are not limited to: anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, including, but not limited to: carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.
In the present invention, the light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and combining the holes with the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq 3); carbazole-based compounds; a dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzocarbazole-based, benzothiazole-based, and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) based polymers; a spiro compound; polyfluorene; rubrene, etc., but is not limited thereto.
Preferably, the organic thin film layer further includes at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.
In the present invention, the material of the hole transport layer is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and has high hole mobility. Illustratively, the hole transport layer materials include, but are not limited to, aromatic amine compounds, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
In the present invention, the material of the hole injection layer is a material that receives holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the material of the hole injection layer is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. The materials of the hole injection layer include, but are not limited to: metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrenes, quinacridones, perylenes, anthraquinones, conductive polymers (e.g., polyaniline, polythiophene), and the like, and may further contain a compound capable of p-doping.
In the present invention, a light-emitting auxiliary layer (multi-layer hole transporting layer) may be further added between the hole transporting layer and the light-emitting layer. The light-emitting auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes also referred to as a second hole transport layer. The light emitting auxiliary layer enables holes transferred from the anode to smoothly move to the light emitting layer, and can block electrons transferred from the cathode to confine electrons in the light emitting layer, reduce potential barrier between the hole transporting layer and the light emitting layer, reduce driving voltage of the organic electroluminescent device, further increase utilization ratio of holes, thereby improving luminous efficiency and lifetime of the device.
In the present invention, the electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, materials known in the art, such as an arylamine-based organic material, may be used.
In the present invention, the hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and materials known in the art, such as triazine-based compounds, may be used.
In the present invention, the electron transport layer may function to promote electron transport. The material of the electron transport layer is a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer, and a material having high electron mobility is suitable. The electron transport layer may include an electron buffer layer, a hole blocking layer, an electron transport layer, and the like.
In the present invention, the electron injection layer may function to promote electron injection. The material of the electron injection layer has an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the hole injection layer, and in addition, has an excellent thin film forming ability. Specific examples thereof include, but are not limited to: fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and the like, and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives and the like.
In the invention, the organic electroluminescent device comprises at least one organic thin film layer.
In the present invention, as a material of the anode, a material having a large work function is generally preferable so that holes are smoothly injected into the organic material layer. Including but not limited to: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO, al or SnO 2 Sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)](PEDOT), polypyrrole and polyaniline.
As the cathode material, a material having a small work function is generally preferable so that electrons are smoothly injected into the organic material layer. Materials for the cathode include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials, e.g. LiF/Al or LiO 2 Al, etc.
In the present invention, the organic electroluminescent device may be of a top emission type, a bottom emission type or a bi-directional emission type, depending on the materials used.
In the present invention, the existing hole injection material, hole transport material, electron blocking layer material, host material, hole blocking layer material, electron transport layer material, and electron injection material may be used for other layer materials in the OLED device.
In the invention, the cathode surface of the organic electroluminescent device is also provided with a light extraction layer.
The numerical ranges recited herein include not only the recited point values, but also any point values between the recited numerical ranges that are not recited, and are limited to, and for the sake of brevity, the invention is not intended to be exhaustive of the specific point values that the recited range includes.
Compared with the prior art, the invention has the beneficial effects that:
according to the organic compound provided by the invention, through a specific molecular structure design, cycloalkyl is introduced into a mother nucleus structure, and a multi-aromatic ring structure is introduced, so that the organic compound is used as a doping material of a light-emitting layer of an OLED device, the light-emitting efficiency and the light-emitting service life of the device can be effectively improved, and industrialization can be realized.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of intermediate d2 in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the compound-1 provided in example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the compound-5 provided in example 2 of the present invention;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of intermediate c2 in example 3 of the present invention;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the compound-97 provided in example 3 of the present invention.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
In addition, it should be noted that the numerical values set forth in the following examples are as precise as possible, but those skilled in the art will understand that each numerical value should be construed as a divisor rather than an absolute precise numerical value due to measurement errors and experimental operation problems that cannot be avoided.
Example 1
The present embodiment provides an organic compound, which is compound 1; the preparation method of the organic compound comprises the following steps:
the preparation method of the raw material B-1 comprises the following steps:
(a) Raw material e-1 (1.0 eq) was dissolved in THF, naOH solution (6.0 eq) was added at room temperature, and the reaction was carried out at 50℃for 5 hours. TLC detection reaction was complete. The THF solvent was removed by rotary evaporation, diluted with water and washed with ethyl acetate. Acidifying the water phase with hydrochloric acid to adjust pH=2, extracting the organic phase with ethyl acetate, washing with salt water, drying with magnesium sulfate, and spin-drying to obtain a product intermediate d1;
(b) Intermediate d1 (1.0 eq), copper powder (1.5 eq), and cuprous oxide (0.3 eq) were added sequentially to quinoline under nitrogen. The temperature is raised to 230 ℃ for reaction for 10min. After the reaction was completed, the reaction mixture was cooled to room temperature. The solution was poured into water, PH was adjusted to approximately 1 with hydrochloric acid, then extracted 3 times with methyl tert-butyl ether, the organic phases were combined, washed with water, dried and spun-dried. Purifying by column (petroleum ether: ethyl acetate=1:1) to obtain product intermediate d2 (nuclear magnetic resonance spectrum of intermediate d2 is shown in fig. 1);
(c) Intermediate d2 (1.0 eq) was dissolved in t-butanol, triethylamine (1.1 eq) was added, and DPPA (1.1 eq) was added dropwise under nitrogen. After completion of the dropwise addition, the reaction was refluxed overnight (12 h). After the reaction, cooling to room temperature, pouring the mixture into ice water and stirring the mixture for 30 minutes. Extracting the organic phase with ethyl acetate, washing with water, drying, spin drying, and purifying with column (petroleum ether to dichloromethane=10:1) to obtain product intermediate d3;
(d) Intermediate d3 (1.0 eq) was dissolved in DCM and a small amount of trifluoroacetic acid was added dropwise at room temperature, and stirred at room temperature for 1 hour after the addition. TLC detects the completion of the reaction of the starting materials, spin-dry the solvent. The residue was dissolved in DCM, washed 2 times with aqueous sodium hydroxide, brine, dried over magnesium sulfate and spun-dried to give product intermediate c3;
(e) Intermediate c3 (1.0 eq) was dissolved in acetonitrile, copper bromide (1.2 eq) was added and cooled to 0 ℃ under nitrogen protection; tert-butyl nitrite (1.5 eq) was added dropwise and allowed to react overnight (12 h) at room temperature. Pouring into water, stirring, extracting organic phase with petroleum ether, washing with saline solution, drying, and spin drying. Purifying by column (petroleum ether washing) to obtain raw material 1;
(f) Raw material 1 (1.0 eq) was addedAdding t-Buona (2.0 eq) and anhydrous toluene into a reaction bottle, and stirring for 30 minutes under the protection of nitrogen; then respectively adding the intermediate c3 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring and gradually separating out product raw material B-1.
The raw material A-1 is the existing material (CAS: 960305-14-0);
the specific synthetic procedure for compound 1 is as follows:
(1) Raw material B-1 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then respectively adding the raw materials A-1 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq), heating to 90 ℃ for reaction for 16 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily substance, adding methanol, stirring and gradually separating out a product, namely an intermediate 1 (yield: 74.8%);
(2) Raw material B-1 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. The intermediate 1 (1.1 eq) and Pd were added separately 2 (dba) 3 （0.03eq）、P(t-Bu) 3 (0.2 eq), heating to 110 ℃ for reaction for 24 hours, and cooling after the completion of the spot plate confirmation reaction. Cooling the reaction solution to 50deg.C, adding water to stop the reaction, stirring for 10 min, standing for separating liquid, and spin-drying toluene layer to obtain blackA coloured oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1:2, pouring out all product points, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring to gradually precipitate solid, and drying to obtain intermediate 2 (yield: 50.4%);
(3) Intermediate 2 (1.0 eq) was dissolved in tert-butylbenzene and stirred for 15 minutes at-40℃under nitrogen. Tert-butyllithium (2.0 eq) was injected, then the temperature was raised to 60℃for 2 hours, then the reaction was evacuated to remove a small amount of n-pentane, the reaction was cooled to-40℃again, boron tribromide (2.0 eq) was added, and the mixture was stirred at room temperature for 30 minutes. Then the reaction solution was cooled to 0℃and DIPEA (5.0 eq) was added thereto and the reaction solution was slowly returned to room temperature, and the reaction solution was heated to 100℃for 2 hours and then cooled to room temperature. The reaction solution was washed with brine, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, half of the tert-butylbenzene was distilled off, and then methanol was added thereto and stirred to precipitate a large amount of yellow solid. The yellow solid was purified by column chromatography with dichloromethane: petroleum ether = 1:6 to obtain the purified compound-1 (yield: 20.3%).
The obtained compound-1 was subjected to detection analysis, and the results were as follows:
HPLC purity: > 99.2%.
Mass spectrometry test: a mass spectrometer model Waters XEVO TQD, using an ESI source.
Test value ((ESI, M/Z): [ M+H ] +): 811.15;
elemental analysis:
the calculated values are: c, 87.38, H, 7.83, B, 1.33, N, 3.45;
the test values are: c, 87.11, H, 7.97, B, 1.54, N, 3.67.
Nuclear magnetic resonance hydrogen spectrum: the results are shown in FIG. 2.
Example 2
The embodiment provides an organic compound, the organic compound is compound 5, and the preparation method of the organic compound includes:
the preparation method of the B-5 comprises the following steps:
the starting material d-1 (1.0 eq) was added to the reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Intermediate c3 (1.0 eq) and Pd obtained in the same manner as in example 1 were each added 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1: and 4, pouring out all product points, collecting and spin-drying to obtain oily matters, and adding petroleum ether to stir and gradually separating out products to obtain the raw material B-5.
The specific synthesis steps of the compound 5 are as follows:
(1) Raw material B-5 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then respectively adding the raw materials A-1 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq), heating to 90 ℃ for reaction for 16 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily substance, adding methanol, stirring to gradually precipitate a product, namely an intermediate 1 (yield: 72.6%);
(2) Raw material B-5 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then adding intermediate 1 (1.1 eq) and Pd in turn 2 (dba) 3 （0.03eq）、P(t-Bu) 3 (0.2 eq), heating to 110 ℃ for reaction for 24 hours, and cooling after the completion of the spot plate confirmation reaction. ReactionWhen the temperature of the solution is reduced to 50 ℃, water is added to stop the reaction, the mixture is stirred for 10 minutes, the mixture is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:2, pouring out all product points, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring to gradually precipitate solid, and drying to obtain intermediate 2 (yield: 48.6%);
(3) Intermediate 2 (1.0 eq) was dissolved in tert-butylbenzene and stirred for 15 minutes at-40℃under nitrogen. Tert-butyllithium (2.0 eq) was injected, then the temperature was raised to 60℃for 2 hours, then the reaction was evacuated to remove a small amount of n-pentane, the reaction was cooled to-40℃again, boron tribromide (2.0 eq) was added, and the mixture was stirred at room temperature for 30 minutes. Then the reaction solution was cooled to 0℃and DIPEA (5.0 eq) was added thereto and the reaction solution was slowly returned to room temperature, and the reaction solution was heated to 100℃for 2 hours and then cooled to room temperature. The reaction solution was washed with brine, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, half of the tert-butylbenzene was distilled off, and then methanol was added thereto and stirred to precipitate a large amount of solid. During the reaction, several different isomer compounds (e.g., compound 5a, compound 5 b) are produced, and then the solid containing the isomers is purified by column chromatography, and the isomer compounds produced during the reaction are removed by using methylene chloride: petroleum ether = 1:6 to obtain purified compound-5 (yield: 9.4%).
The resulting compound-5 was subjected to detection analysis, and the results were as follows:
HPLC purity: > 99.3%.
Mass spectrometry test: a mass spectrometer model Waters XEVO TQD, using an ESI source.
Test value ((ESI, M/Z): [ M+H ] +): 735.03;
elemental analysis:
the calculated values are: c, 86.62, H, 8.09, B, 1.47, N, 3.81;
the test values are: c, 86.40, H, 8.18, B, 1.60, N, 3.97.
Nuclear magnetic resonance hydrogen spectrum: the results are shown in FIG. 3.
Example 3
The embodiment provides an organic compound, the organic compound is a compound 97, and the preparation method of the organic compound 97 includes:
the preparation method of the raw material B-97 comprises the following steps:
(a) Raw material a (1.0 eq) was dissolved in tetrahydrofuran and added to a 10% aqueous sulfuric acid solution, stirred and heated to 50 ℃, and an aqueous sodium bromate (2.0 eq) solution was added dropwise to react for 4.5 hours. After the reaction, cooling, separating liquid, extracting once by tetrahydrofuran, combining organic layers, washing for 2 times, drying by anhydrous magnesium sulfate, purifying and removing the isomer compound generated in the reaction by column chromatography, and using dichloromethane: petroleum ether = 1:4, flushing out a product point, collecting and spin-drying to obtain oily substance, and obtaining an intermediate c2 (a nuclear magnetic resonance spectrogram of the intermediate c2 is shown in figure 4);
(b) Intermediate c2 (1.0 eq) was added to the reaction flask, followed by t-BuONa (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Then respectively adding the raw materials d-1-97 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq) was allowed to react at 90℃for 10 hours, after the completion of the spot-plate reaction, the reaction mixture was cooled to about 50℃and then quenched by adding water, stirred for 10 minutes, and the mixture was allowed to stand still for separation, followed by spin-drying of the toluene layer to give a black oil. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily matters, adding petroleum ether, and stirring to gradually separate out products to obtain B-97;
raw material C-97 is the existing material (CAS: 1352756-38-7)
The specific preparation steps of compound 97 include:
(1) Raw material B-97 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene under nitrogen protectionStirring for 30 minutes. Then respectively adding the raw materials A-1 (1.0 eq) and Pd 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.2 eq), heating to 90 ℃ for reaction for 16 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:4, pouring out all product points, collecting and spin-drying to obtain oily substance, adding methanol, stirring to gradually precipitate a product, namely an intermediate 1 (yield: 71.1%);
(2) Raw material C-97 (1.0 eq) was added to a reaction flask, followed by t-Buona (2.0 eq) and anhydrous toluene, and stirred under nitrogen for 30 minutes. Intermediate 1 (1.1 eq) and Pd were added separately 2 (dba) 3 （0.03eq）、P(t-Bu) 3 (0.2 eq), heating to 110 ℃ for reaction for 24 hours, and cooling after the completion of the spot plate confirmation reaction. When the temperature of the reaction liquid is reduced to 50 ℃, water is added to stop the reaction, the reaction is stirred for 10 minutes, the reaction liquid is separated still, and the toluene layer is dried by spinning to obtain black oily matter. Purification by column chromatography, with dichloromethane: petroleum ether = 1:2, pouring out all product points, collecting and spin-drying to obtain oily substance, adding petroleum ether, stirring to gradually precipitate solid, and drying to obtain intermediate 2 (yield: 55.3%);
(3) Intermediate 2 (1.0 eq) was dissolved in tert-butylbenzene, stirred at-40 ℃ under nitrogen for 15 min, tert-butyllithium (2.0 eq) was injected, then heated to 60 ℃ for 2 h, then vacuum was applied to remove a small amount of n-pentane, the reaction was cooled to-40 ℃, boron tribromide (2.0 eq) was added, and stirred at room temperature for 30 min. Then the reaction solution was cooled to 0℃and DIPEA (5.0 eq) was added thereto and the reaction solution was slowly returned to room temperature, and the reaction solution was heated to 100℃for 2 hours and then cooled to room temperature. The reaction solution was washed with brine, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, half of the tert-butylbenzene was distilled off, and then methanol was added thereto and stirred to precipitate a large amount of solid. During the reaction, several different isomer compounds (e.g., compound 97a, compound 97b, compound 97c, compound 97d, compound 97 e) are produced, and then the isomer-containing solid is purified by column chromatography to remove the isomer compounds produced during the reaction, using methylene chloride: petroleum ether = 1:6 to give a purified compound 97 (yield: 7.4%).
The resulting compound 97 was subjected to detection analysis, and the result was as follows:
HPLC purity: > 99.2%.
Mass spectrometry test: a mass spectrometer model Waters XEVO TQD, using an ESI source.
Test value ((ESI, M/Z): [ M+H ] +): 809.31;
elemental analysis:
the calculated values are: c, 86.11, H, 9.10, B, 1.34, N, 3.46;
the test values are: c, 85.87, H, 9.27, B, 1.53, N, 3.67.
Nuclear magnetic resonance hydrogen spectrum: the results are shown in FIG. 5.
Examples 4 to 50
Examples 4 to 50 provide an organic compound, respectively, the synthetic method of which is referred to the synthetic methods of examples 1 to 3; the specific structures and characterization of the results of the organic compounds provided in examples 4-50 are shown in Table 1:
TABLE 1
Application example 1
The application example provides an organic electroluminescent device, which comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer (comprising a compound 1), a hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a light extraction layer which are sequentially laminated; the preparation method of the organic electroluminescent device comprises the following steps:
a. ITO anode: washing ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing with ultrasonic waves for 30min, washing with distilled water for 2 times repeatedly, washing with ultrasonic waves for 10min, baking with a vacuum oven at 220 ℃ for 2 hours after washing, and cooling after baking is finished, so that the glass substrate can be used. Using the substrate as an anode, and using an evaporator to perform an evaporation device process, and evaporating other functional layers on the substrate in sequence;
b. HIL (hole injection layer): vacuum evaporating the hole injection layer material HT-1 at an evaporating rate of 1 Å/s) And P-dopant (>). The evaporation rate ratio of HT-1 to P-dock is 97:3, hil thickness 10 nm;
c. HTL (hole transport layer): vacuum evaporating 120nm HT-1 on the hole injection layer as a hole transport layer at an evaporation rate of 1.5 Å/s;
d. EBL (electron blocking layer): vacuum evaporating 10nm EBL-1 on the hole transport layer at an evaporation rate of 0.5 Å/s) As an electron blocking layer;
e. EML (light emitting layer): then, a Host material having a thickness of 20nm was vacuum-deposited on the electron blocking layer at a deposition rate of 1 Å/s (Host,) And a doping material (compound 1) as a light-emitting layer; wherein the evaporation rate ratio of Host to compound 1 is 98:2;
f. HBL (hole blocking layer): vacuum evaporating HB-1 of 5nm on the surface of the light-emitting layer at an evaporation rate of 0.5 Å/s) As a hole blocking layer;
g. ETL (electron transport layer): vacuum evaporating 3 on the surface of the hole blocking layer at an evaporation rate of 1 Å/s0nm ET-1%) As an electron transport layer;
h. EIL (electron injection layer): evaporating Yb film layer 1.0nm at an evaporation rate of 0.5 Å/s to form an electron injection layer;
i. And (3) cathode: and evaporating magnesium and silver at an evaporation rate ratio of 1 Å/s, wherein the evaporation rate ratio is 1:9, and the thickness is 18 nm, so that the OLED device is obtained.
The invention also comprises a light extraction layer arranged on the surface of the cathode, CPL-1 with the thickness of 70nm is vacuum evaporated on the surface of the cathode at the evaporation rate of 1 Å/s) As a light extraction layer; packaging the substrate subjected to evaporation: firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
Application examples 2 to 50
Application examples 2 to 50 respectively provide an organic electroluminescent device differing from application example 1 only in that the compound 1 was replaced with the same amount of the compound 2, 5, 8, 11, 19, 20, 22, 24, 25, 26, 27, 32, 35, 42, 44, 45, 46, 49, 55, 61, 62, 65, 67, 69, 70, 72, 77, 80, 82, 86, 89, 92, 93, 96, 97, 100, 110, 114, 116, 128, 133, 143, 151, 152, 153, 154, 156, 163, 165, and other structures, materials and preparation methods were the same as application example 1.
Comparative application examples 1 to 3
Comparative examples 1 to 3 each provide an organic electroluminescent device differing from example 1 only in that the compound 1 was replaced with an equivalent amount of the compound a #, respectively) Compound b%) Compound c (>) Other structures, materials and preparation methods are the same as in application example 1.
Performance testing
The organic electroluminescent devices provided in application examples 1 to 50 and comparative application examples 1 to 3 were characterized for driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits), and the test results are shown in table 2.
TABLE 2
Note that: in the blue top emission device, the current efficiency is greatly affected by chromaticity, and thus, the ratio of the luminous efficiency to CIEy is defined as a BI value, i.e., bi= (cd/a)/CIEy, taking into consideration the factor of chromaticity on efficiency.
As can be seen from the table, the organic compound provided by the invention has a specific molecular structure design, and the driving voltage of the organic electroluminescent device prepared by using the organic compound as a doping material in the luminescent layer is low and is 3.19-3.35V; the luminous efficiency is high and is 9-10.48 cd/A; the service life of the T95 is 505-538 h.
As is clear from the comparison of application examples 1 and comparative application examples 1 to 3, the luminous efficiency and the lifetime of the device are greatly reduced, not in the specific structural design of the present invention.
And compared with the comparative compound b, the novel cycloalkyl structure is introduced into the compound 61, so that a high conjugated electron distribution system of the compound is improved, molecules are effectively and orderly stacked, and optimal carrier transmission and migration are exerted, and the luminous efficiency and the service life of the compound are improved.
By introducing a more rigid cycloalkyl structure into the compound 97 of the present invention compared with the comparative compound c, the single-triplet gap can be reduced to the greatest extent, intermolecular aggregation and crystallization are avoided, and the stability is better, thereby improving the lifetime of the device.
In summary, according to the organic compound provided by the invention, through a specific molecular structure design, a relatively rigid cycloalkyl structure is introduced into a mother nucleus structure, and meanwhile, a multi-aromatic ring structure is introduced, so that the organic compound is used as a doping material of a light-emitting layer of an OLED device, the light-emitting efficiency and the light-emitting service life of the device can be effectively improved, and industrialization can be realized.
The applicant declares that the above is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be apparent to those skilled in the art that any changes or substitutions that are easily conceivable within the technical scope of the present invention disclosed by the present invention fall within the scope of the present invention and the disclosure.
Claims (7)
1. An organic compound, characterized in that the organic compound has a structure represented by formula I:
a formula I;
wherein ring Ar 1 Ring Ar 2 Each independently selected from any one of the following structures:
、；
R 11 any one selected from the following groups:
hydrogen, hydrogen,；
m 1 An integer of 0 to 4;
the dashed line represents a merozoite chemical bond, and its optional merozoite position;
the R is 1 、R 2 Each independently selected from any one of the following structures:
、、、
、；
wherein R is 14 、R 15 、R 16 、R 17 Each independently selected from any one of the following groups:
hydrogen, hydrogen,；
X is selected from O, S, CR 21 R 22 Any of which, R 21 、R 22 Selected from methyl;
m 4 an integer of 0 to 5; m is m 5 An integer of 0 to 9; m is m 6 An integer of 0 to 7; m is m 7 An integer of 0 to 4;
". Times" represent the site of attachment;
R 3 selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, phenyl, tolyl, xylyl, diethylphenyl, isopropylphenyl, 1, 3-diisopropylphenylAny one of tert-pentylphenyl and 1, 3-di-tert-butylphenyl;
the ring Ar 1 、Ar 2 At least one group beingThe method comprises the steps of carrying out a first treatment on the surface of the And/or, the R 1 、R 2 At least one group of +.>。
2. The organic compound according to claim 1, wherein the organic compound has any one of the following structures:
；
the ring Ar 1 Ring Ar 2 、R 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
3. The organic compound according to claim 1, wherein the organic compound has any one of the following structures:
；
the R is 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
4. An organic compound according to claim 3, wherein the organic compound has any one of the following structures:
；
the R is 1 、R 2 、R 3 Each independently has the same defined range as in formula I.
5. An organic compound, characterized in that the organic compound is selected from any one of the following compounds 1-174:
；
；
；
；
；
；
；/>
；/>
；/>
6. a process for producing an organic compound according to any one of claims 1 to 5, wherein the synthetic route of the process is as follows:
；
or alternatively, the first and second heat exchangers may be,
when R is 3 When methyl:
。
7. an organic electroluminescent device, characterized in that the organic electroluminescent device comprises the organic compound according to any one of claims 1 to 5.
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