CN114957189A - Compound, organic electroluminescent device and display device - Google Patents
Compound, organic electroluminescent device and display device Download PDFInfo
- Publication number
- CN114957189A CN114957189A CN202110218756.3A CN202110218756A CN114957189A CN 114957189 A CN114957189 A CN 114957189A CN 202110218756 A CN202110218756 A CN 202110218756A CN 114957189 A CN114957189 A CN 114957189A
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- China
- Prior art keywords
- compound
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- synthesis
- organic electroluminescent
- carbon atoms
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 112
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- -1 spirofluorene Chemical compound 0.000 claims description 9
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- JPAMAQWNSMPRLT-UHFFFAOYSA-N 11h-indeno[2,1-a]phenanthrene Chemical compound C1=CC=C2C3=CC=C4C5=CC=CC=C5CC4=C3C=CC2=C1 JPAMAQWNSMPRLT-UHFFFAOYSA-N 0.000 claims description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 4
- YYGRIGYJXSQDQB-UHFFFAOYSA-N Benzo[b]chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC5=CC=CC=C5C=C4C=CC3=C21 YYGRIGYJXSQDQB-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- RAASUWZPTOJQAY-UHFFFAOYSA-N Dibenz[a,c]anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C3=CC=CC=C3C2=C1 RAASUWZPTOJQAY-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 23
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000001514 detection method Methods 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- 238000001704 evaporation Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 16
- 238000001819 mass spectrum Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 15
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
- 229940127271 compound 49 Drugs 0.000 description 3
- 229940126545 compound 53 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- QRMLAMCEPKEKHS-UHFFFAOYSA-N 9,9-dimethyl-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC(C=C1)=CC=C1C1=CC=CC=C1 QRMLAMCEPKEKHS-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
- AESPYQQDASDLHC-UHFFFAOYSA-N 2h-benzo[g]thiochromene Chemical compound C1=CC=C2C=C(C=CCS3)C3=CC2=C1 AESPYQQDASDLHC-UHFFFAOYSA-N 0.000 description 1
- KCHRZPPNAWBDQZ-UHFFFAOYSA-N 5-bromo-7,7-dimethylbenzo[c]fluorene Chemical compound C1=C(Br)C2=CC=CC=C2C2=C1C(C)(C)C1=CC=CC=C12 KCHRZPPNAWBDQZ-UHFFFAOYSA-N 0.000 description 1
- BUADUHVXMFJVLH-UHFFFAOYSA-N 7-chloro-3-imidazol-1-yl-2H-1,2,4-benzotriazin-1-ium 1-oxide Chemical compound N1[N+](=O)C2=CC(Cl)=CC=C2N=C1N1C=CN=C1 BUADUHVXMFJVLH-UHFFFAOYSA-N 0.000 description 1
- SNUKBTHMZLUJKR-UHFFFAOYSA-N 9-bromo-7,7-dimethylbenzo[c]fluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=C(C=CC=C4)C4=C3C2=C1 SNUKBTHMZLUJKR-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
-
- 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
- C09K2211/1088—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
Abstract
The application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device and a display device. The structural formula of the compound is shown as the formula (I):
Description
Technical Field
The application relates to the field of electroluminescence, in particular to a compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
However, since there is a great gap between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted, and one of the most important factors is that the efficiency of the device still does not reach a desired level. This is because most of light is confined inside the light emitting device due to mode loss of the substrate, loss of surface plasmon, and waveguide effect, thereby reducing the light emitting efficiency of the device. Improving the light emitting efficiency of the device, and using light extraction materials is one of the effective methods. The light extraction Layer (CPL) can adjust the light extraction direction and the light extraction efficiency by reducing the surface plasma effect of the metal electrode, and can effectively improve the light extraction efficiency of the device, thereby improving the luminous efficiency of the device. At present, the light extraction material is of a single type and has an unsatisfactory effect, and developing a more effective light extraction material is one of the more serious challenges facing OLED workers.
In addition, the selection of the materials of the light-emitting layer and other organic functional layers also has a great influence on the current efficiency and driving voltage of the device, and functional layer materials with higher performance are still being explored.
Therefore, in order to meet the higher requirements of people for OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the art.
Disclosure of Invention
The application discloses a carbazole compound, an organic electroluminescent device and a display device, wherein the organic electroluminescent device made of the carbazole compound has lower driving voltage and higher current efficiency.
In order to achieve the purpose, the application provides the following technical scheme:
a compound has a structural formula shown as a formula (I),
wherein m and n are selected from 0 or 1;
A、B、Ar 3 each independently selected from aromatic groups containing 6 to 40 carbon atoms, wherein hydrogen in the aromatic groups containing 6 to 40 carbon atoms can be substituted by R;
Ar 1 selected from the formula (II) in which R 1 ～R 10 At least one is absent and the corresponding one carbon atom is attached to the N atom or A in formula (I); x is selected from oxygen or sulfur;
Ar 2 one selected from the following structures A-1 to A-7 or a structure represented by a formula (II),
f, e are selected from 0 or 1, and at least one of them is selected from 1;
any one of SP2 hybridized with and bonded to only two carbon atoms of A-1 to A-7 may be bonded to N or B in formula (I) as a bonding site;
the hydrogen in A-1 to A-7 may be substituted by 1 or more R;
r and R 1 ～R 14 Independently selected from hydrogen, deuterium, F, CN, alkyl group containing 1-20 carbon atoms, alkoxy group containing 1-20 carbon atoms or aryl group containing 6-40 carbon atoms.
Further, A, B, Ar 3 Selected from the group consisting of benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene, and benzindenofluorene.
Further, the aryl group with 6-40 carbon atoms is selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene and benzindenofluorene.
Further, the structure of the compound is:
further, the structure of the compound is:
further, R 1 And R 10 Each independently selected from F, CN, methoxy, phenyl or biphenyl.
Further, the compound is selected from one of structural formulas 1 to 162, wherein the compound of structural formulas 1 to 81 is as follows:
the compounds of the structural formulas 82-162 are respectively obtained by replacing O in the compounds of the structural formulas 1-81 with S.
An organic electroluminescent device comprising a compound as described herein.
A display device includes the organic electroluminescent device provided by the application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the compound shown in the formula (I) is a novel compound, and can be used for organic electroluminescent devices and used as HTL and CPL materials. In addition, the OLED device prepared by using the compound material shown in the formula (I) has low driving voltage and high luminous efficiency.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
It should be noted that: in the present application, all embodiments and preferred methods mentioned herein can be combined with each other to form new solutions, if not specifically stated. In the present application, all the technical features mentioned herein as well as preferred features may be combined with each other to form new technical solutions, if not specifically stated. In the present application, percentages (%) or parts refer to percent by weight or parts by weight relative to the composition, unless otherwise specified. In the present application, the components referred to or the preferred components thereof may be combined with each other to form a new embodiment, if not specifically stated. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "6 to 22" means that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is simply a shorthand representation of the combination of these values. The "ranges" disclosed herein may be in the form of lower limits and upper limits, and may be one or more lower limits and one or more upper limits, respectively. In the present application, unless otherwise indicated, the individual reactions or process steps may or may not be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present application.
Synthesis example 1 Synthesis of Compound 1
(1) Synthesis of intermediate M-1
A250 ml three-necked flask was charged with nitrogen, 100 ml of dried toluene, 1.69 g (0.01mol) of 4-aminobiphenyl, 3.23 g (0.01mol) of 9-bromo-7, 7-dimethyl-7H-benzo [ c ] fluorene, 0.0575 g (0.0001mol) of Pd (dba)2 (palladium bis (dibenzylideneacetone), 0.4 g (0.0002mol) of a toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015mol) of sodium tert-butoxide, heated to 60 ℃ for 12 hours, cooled, subjected to liquid separation with water, washed with water to neutrality of the organic layer, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and recrystallized from a mixed solvent of toluene and methanol to give 3.8 g of the compound represented by M-1.
Performing mass spectrum detection on the compound shown as M-1, and determining that the molecular M/z is as follows: 411.
(2) synthesis of Compound represented by formula 1
A500-ml three-necked flask was placed under nitrogen protection, 200 ml of dried toluene, 4.11 g (0.01mol) of the compound represented by M-1, 2.97 g (0.01mol) of 3-bromobenzo [ kl ] xanthene, 0.0575 g (0.0001mol) of Pd (dba)2 (palladium bis-dibenzylideneacetone), 0.4 g (0.0002mol) of a toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015mol) of sodium tert-butoxide, and the mixture was heated to reflux for 6 hours, cooled, water was added to separate the organic layer, the organic layer was washed with water to neutrality, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, and eluted with petroleum ether to obtain 5.7 g of the compound represented by formula 1.
Performing mass spectrum detection on the compound shown in the formula 1, and determining the molecular m/z as follows: 627.
the compound shown in the formula 1 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, Switzerland, Avance II 400MHz nuclear magnetic resonance spectrometer, CDCl3), delta 8.84(m, 1H), delta 8.21(d, 1H), delta 8.06(m, 1H), delta 7.97(m, 1H), delta 7.79-7.72 (m, 3H), delta 7.66(d, 1H), delta 7.64(m, 1H), delta 7.60-7.30 (m, 11H), delta 7.29-7.13 (m, 5H), delta 7.11(d, 1H), delta 6.41(m, 1H), delta 1.76(s, 6H).
Synthesis example 2 Synthesis of Compound 10
Synthesis method referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was replaced with 8-bromobenzo [ kl ] xanthene to give Compound 10.
Performing mass spectrometric detection on the compound shown in the formula 10 to determine that the molecule m/z is: 627.
synthesis example 3 Synthesis of Compound 28
(1) Synthesis of intermediate M-2
A 250 ml three-neck flask, under the protection of nitrogen, is added with 60 ml of toluene, 40 ml of ethanol and 20 ml of water, then is added with 2.97 g (0.01mol) of 8-bromobenzo [ kl ] xanthene, 1.56 g (0.01mol) of 4-chlorobenzeneboronic acid, 2.12 g (0.02mol) of sodium carbonate and 0.115 g (0.0001mol) of tetratriphenylphosphine palladium, the temperature is slowly raised to reflux reaction for 8 hours, the temperature is reduced, water is added for liquid separation, an organic layer is washed with water, magnesium sulfate is dried, after magnesium sulfate is filtered and removed, a solvent is removed under reduced pressure, the obtained solid column chromatography is separated, and petroleum ether is eluted to obtain 2.9 g of a compound shown in M-2.
Performing mass spectrum detection on the compound shown by the M-2, and determining that the M/z of the molecule is as follows: 328.
(2) synthesis of Compound represented by formula 28
Synthesis method referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene was replaced by the compound represented by M-2, the reflux time was changed from 6 hours to 24 hours to obtain Compound 28.
Performing mass spectrometric detection on the compound shown in formula 28 to determine that the molecule m/z is: 703.
synthesis example 4 Synthesis of Compound 49
(1) Synthesis of intermediate M-3
Adding 50 ml of DMF (dimethyl formamide), 2.97 g (0.01mol) of 8-bromobenzo [ kl ] xanthene into a 250 ml three-neck flask, controlling the temperature to be 20-25 ℃, adding 2.25 g (0.01mol) of N-iodosuccinimide (NIS) in batches under stirring, controlling the temperature to be 20-25 ℃ for reaction for 2 hours, heating to be 40-45 ℃ for reaction for 1 hour, heating to be 60 ℃ for reaction for 1 hour, cooling, adding water and dichloromethane for separating liquid, washing an organic layer with water, separating by silica gel column chromatography, eluting with petroleum ether to obtain 1.8 g of a compound shown in M-3.
The compound shown as the formula M-3 is subjected to mass spectrum detection, the maximum two peaks are 422 and 424, and the molecular formula of the product is determined as follows: c 16 H 8 BrIO。
The compound shown as the formula M-3 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, Switzerland, Avance II 400MHz NMR spectrometer, CDCl3), delta 8.51(m, 1H), delta 7.88(m, 1H), delta 7.82(m, 2H), delta 7.68(m, 1H), delta 7.62(d, 1H), delta 7.44(d, 1H), delta 7.10(m, 1H).
(2) Synthesis of intermediate M-4
A 250 ml three-neck bottle is filled with toluene 60 ml, ethanol 40 ml and water 20 ml under the protection of nitrogen, then 4.23 g (0.01mol) of the compound shown in M-3, 1.22 g (0.01mol) of phenylboronic acid, 2.12 g (0.02mol) of sodium carbonate and 0.115 g (0.0001mol) of palladium tetrakistriphenylphosphine are added, the temperature is slowly raised to 60 ℃ for reaction for 8 hours, the temperature is reduced, water is added for liquid separation, an organic layer is washed with water, magnesium sulfate and a small amount of 200-300-mesh silica gel are added for drying, after the magnesium sulfate and the silica gel are filtered and removed, the solvent is removed under reduced pressure, the obtained solid is recrystallized for 2 times by using a mixed solvent of chlorobenzene and methanol, and 3.1 g of the compound shown in M-4 is obtained.
Mass spectrum detection is carried out on the compound shown in M-4, the maximum two peaks are 372 and 374, and the molecular formula of the product is determined as follows: c 22 H 13 BrO。
(3) Synthesis of intermediate M-5
A 250 ml three-neck flask, under the protection of nitrogen, adding 60 ml of toluene, 40 ml of ethanol and 20 ml of water, then adding 3.23 g (0.01mol) of 5-bromo-7, 7-dimethyl-7H-benzo [ c ] fluorene, 1.56 g (0.01mol) of 4-chlorobenzeneboronic acid, 2.12 g (0.02mol) of sodium carbonate and 0.115 g (0.0001mol) of tetratriphenylphosphine palladium, slowly heating to reflux reaction for 8 hours, cooling, adding water for liquid separation, washing an organic layer with water, drying magnesium sulfate, filtering to remove the magnesium sulfate, removing the solvent under reduced pressure, carrying out chromatographic separation on the obtained solid column, eluting with petroleum ether, and obtaining 3.0 g of the compound represented by M-5.
Performing mass spectrum detection on the compound shown in M-5, and determining that the molecular M/z is as follows: 354.
(4) synthesis of intermediate M-6
A250 ml three-necked flask was charged with nitrogen, 100 ml of dried toluene, 1.69 g (0.01mol) of 4-aminobiphenyl, 3.55 g (0.01mol) of M-5, 0.0575 g (0.0001mol) of Pd (dba)2 (bis-dibenzylideneacetone palladium), 0.4 g (0.0002mol) of a toluene solution containing 10% of tri-tert-butylphosphine, 1.44 g (0.015mol) of sodium tert-butoxide, heated to reflux for 24 hours, cooled, added with water for liquid separation, washed with water of the organic layer to neutrality, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and recrystallized from a mixed solvent of toluene and ethanol to give 3.9 g of M-6-derived compound.
Performing mass spectrum detection on the compound shown as M-6, and determining that the molecular M/z is as follows: 487.
(5) synthesis of Compound 49
Referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was changed to a compound represented by M-4 and the compound represented by M-1 therein was changed to a compound represented by M-6, Compound 49 was obtained.
Performing mass spectrometric detection on the compound shown in formula 49 to determine that the molecule m/z is: 779.
the compound shown in the formula 49 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, Switzerland, Avance II 400MHz NMR spectrometer, CDCl3), δ 8.91-8.86 (m, 2H), δ 8.51(m, 1H), δ 8.23(m, 1H), δ 7.93(m, 1H), δ 7.88(m, 1H), δ 7.83(m, 1H), δ 7.74(m, 2H), δ 7.69(s, 1H), δ 7.65(m, 1H), δ 7.60(m, 1H), δ 7.58-7.32 (m, 18H), δ 7.29-7.23 (m, 3H), δ 7.19-7.13 (m, 2H), δ 1.76(s, 6H).
Synthesis example 5 Synthesis of Compound 52
(1) Synthesis of intermediate M-7
A 250 ml three-neck bottle, adding 50 ml DMF, 4.23 g (0.01mol) of a compound shown as a formula M-3, 0.1 g of cuprous iodide and 1.08 g (0.02mol) of sodium methoxide under nitrogen protection, heating to reflux for reaction for 24 hours, cooling to room temperature, adding water and dichloromethane for separating, washing an organic layer to be neutral, drying magnesium sulfate, filtering to remove magnesium sulfate, concentrating the organic layer to be dry, separating by silica gel column chromatography, adding petroleum ether: ethyl acetate 10: 0.5 (volume ratio) to obtain 2.2 g of a compound represented by M-7.
Performing mass spectrum detection on the compound shown in M-7, wherein the maximum two peaks are 326 and 328, and the molecular formula of the product is determined as follows: c 17 H 11 BrO 2 。
(2) Synthesis of Compound 52
Referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene was changed to a compound represented by M-7 and the compound represented by M-1 was changed to a compound represented by M-6, Compound 52 was obtained.
Performing mass spectrometric detection on the compound shown in formula 52 to determine that the molecule m/z is: 733.
synthesis example 6 Synthesis of Compound 53
(1) Synthesis of intermediate M-8
A 250 ml three-neck bottle is filled with nitrogen, 50 ml of DMF, 4.23 g (0.01mol) of the compound shown as the formula M-3, 0.1 g of cuprous iodide and 1.16 g (0.02mol) of KF are added, the mixture is heated to reflux reaction for 24 hours, the temperature is reduced to room temperature, water and dichloromethane are added for separating liquid, an organic layer is washed to be neutral, magnesium sulfate is dried and filtered, the organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, petroleum ether is eluted, and 1.6 g of the compound shown as M-8 is obtained.
Performing mass spectrum detection on the compound shown in M-8, wherein the maximum two peaks are 314 and 316, and determining the molecular formula of the product as follows: c 16 H 8 BrFO。
(2) Synthesis of Compound 53
Referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene was changed to a compound represented by M-8 and the compound represented by M-1 was changed to a compound represented by M-6, Compound 53 was obtained.
Performing mass spectrometric detection on the compound represented by formula 53 to determine that the molecule m/z is: 721.
synthesis example 7 Synthesis of Compound 54
(1) Synthesis of intermediate M-9
A 250 ml three-neck flask is added with nitrogen protection, 50 ml DMF, 4.23 g (0.01mol) of the compound shown as the formula M-3, 0.1 g of cuprous iodide and 1.79 g (0.02mol) of CuCN are added, the mixture is heated to reflux reaction for 24 hours, the temperature is reduced to room temperature, water and dichloromethane are added for separating liquid, an organic layer is washed to be neutral, magnesium sulfate is dried and filtered, the organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, petroleum ether is eluted, and 1.9 g of the compound shown as M-9 is obtained.
Performing mass spectrum detection on the compound shown as M-9, wherein the maximum two peaks are 321 and 323, and the molecular formula of the product is determined as follows: c 17 H 8 BrNO。
(2) Synthesis of Compound 54
Referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was changed to a compound represented by M-9 and the compound represented by M-1 therein was changed to a compound represented by M-6, Compound 54 was obtained.
Mass spectrometric detection of a compound of formula 54 determines the molecule m/z as: 728.
synthesis example 8 Synthesis of Compound 77
(1) Synthesis of intermediate M-10
A 250 ml three-necked flask is added with nitrogen protection, 30 ml DMF, 2.97 g (0.01mol) 8-bromobenzo [ kl ] xanthene, 0.5 g cuprous iodide and 1.16 g (0.02mol) KF are added, the mixture is heated to reflux reaction for 24 hours, the temperature is reduced to room temperature, water and dichloromethane are added for liquid separation, an organic layer is washed to be neutral by water, magnesium sulfate is dried, magnesium sulfate is filtered out, the organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, petroleum ether is eluted, and 0.9 g of the compound shown in M-10 is obtained.
Performing mass spectrum detection on the compound shown as M-10, and determining that the molecular M/z is as follows: 236.
(2) synthesis of intermediate M-11
Adding 80 ml of DMF (dimethyl formamide), 2.36 g (0.01mol) of 8-fluorobenzo [ kl ] xanthene shown as M-10 into a 250 ml three-necked bottle, controlling the temperature to be 20-25 ℃, adding 1.78 g (0.01mol) of N-bromosuccinimide (NBS) in batches under stirring, controlling the temperature to be 20-25 ℃, reacting for 6 hours, adding water and dichloromethane for separating, washing an organic layer with water, separating by silica gel column chromatography, eluting with petroleum ether to obtain 1.6 g of a compound shown as M-11.
The compound shown as the formula M-11 is subjected to mass spectrum detection, the maximum two peaks are 314 and 316, and the molecular formula of the product is determined as follows: c 16 H 8 BrFO。
The compound shown as the formula M-11 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, Switzerland, Avance II 400MHz NMR spectrometer, CDCl3), delta 8.49(m, 1H), delta 7.71(m, 2H), delta 7.68(m, 1H), delta 7.65(m, 1H), delta 7.46(d, 1H), delta 7.24(m, 1H), delta 7.20(m, 1H).
(3) Synthesis of Compound 77
Referring to the synthesis of Compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was changed to a compound represented by M-11 and the compound represented by M-1 therein was changed to a compound represented by M-6, Compound 77 was obtained.
Performing mass spectrum detection on the compound shown in the formula 77, and determining that the molecular m/z is as follows: 721.
synthesis example 9 Synthesis of Compound 82
Referring to the synthesis of compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene was replaced with 3-bromobenzo [ kl ] thiaanthracene, compound 82 was obtained.
And (2) carrying out mass spectrum detection on the compound shown as 82, and determining that the molecular m/z is as follows: 643.
synthesis of comparative Compounds
Synthesis of comparative Compound H-1:
referring to the synthesis of compound 1 in example 1, except that 3-bromobenzo [ kl ] xanthene was changed to 8-bromobenzo [ kl ] xanthene and the compound represented by M-1 was changed to N- ([1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine, compound H-1 was obtained.
Performing mass spectrum detection on the compound shown in H-1, and determining that the molecular m/z is as follows: 577.
synthesis of comparative Compound H-2
Reference was made to the synthesis of compound 1 of example 1 except that the compound represented by M-1 was changed to N- ([1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine to give compound H-2.
Performing mass spectrum detection on the compound shown in H-2, and determining that the molecular m/z is as follows: 577.
materials used in device examples:
device example 1
The examples used the compounds of the present application as hole transport materials in organic electroluminescent devices, and the comparative examples used H-1 to H-4 as hole transport materials in organic electroluminescent devices.
The organic electroluminescent device has the following structure: ITO/HIL02(100 nm)/hole transport material (40nm)/EM1(30nm)/TPBI (30nm)/LiF (0.5nm)/Al (150 nm).
The preparation process of the organic electroluminescent device is as follows:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent conductive layer (serving as an anode) in a cleaning agent, then washing the glass substrate in deionized water, ultrasonically removing oil in a mixed solvent of acetone and ethanol, baking the glass substrate in a clean environment until the water is completely removed, cleaning the glass substrate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cation beams to improve the surface property and improve the binding capacity with a hole injection layer;
placing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, performing vacuum evaporation on the anode to form HIL02 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100 nm;
respectively carrying out vacuum evaporation on the compound and the contrast material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
vacuum evaporating EM1 on the hole transport layer to serve as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
vacuum evaporating TPBI on the organic light-emitting layer to be used as an electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
and (3) evaporating 0.5nm LiF and 150nm Al on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
The luminance, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.
The organic electroluminescent device properties are shown in table 1 below. And testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance.
TABLE 1
| Hole transport material | Required luminance cd/m 2 | Drive voltage V | Current efficiency cd/A |
| HT-1 | 1000 | 5.62 | 1.58 |
| HT-2 | 1000 | 5.88 | 1.62 |
| HT-3 | 1000 | 5.39 | 1.69 |
| HT-4 | 1000 | 5.61 | 1.51 |
| 1 | 1000 | 5.26 | 1.78 |
| 82 | 1000 | 5.33 | 1.86 |
| 3 | 1000 | 5.38 | 2.01 |
| 4 | 1000 | 5.22 | 1.98 |
| 6 | 1000 | 5.12 | 2.31 |
| 13 | 1000 | 5.27 | 2.19 |
| 17 | 1000 | 5.01 | 2.11 |
| 25 | 1000 | 5.28 | 2.01 |
| 28 | 1000 | 5.18 | 1.96 |
| 35 | 1000 | 5.16 | 2.12 |
| 46 | 1000 | 5.11 | 1.89 |
| 49 | 1000 | 4.52 | 1.96 |
| 53 | 1000 | 4.62 | 2.01 |
| 54 | 1000 | 4.37 | 2.03 |
| 56 | 1000 | 4.51 | 1.98 |
| 59 | 1000 | 4.58 | 1.82 |
| 66 | 1000 | 4.33 | 1.98 |
| 71 | 1000 | 4.62 | 2.21 |
| 77 | 1000 | 4.53 | 2.19 |
From the data in table 1, it is understood that the organic electroluminescent device using the compound of the present application as a hole transport material can improve the luminous efficiency and reduce the driving voltage. The current efficiency of the organic electroluminescent device prepared by the compound can reach more than 1.8 cd/A. Particularly, the effect of the devices corresponding to the compounds 49-77 is more excellent, and the driving voltage of the devices corresponding to the compounds 49-77 can be reduced to be lower than 4.65V.
Device example 2
The compound of the application is selected as a CPL material in an organic electroluminescent device in the embodiment, and H-1-H-4 are selected as CPL materials in the organic electroluminescent device in the comparative embodiment.
The above numbered examples and comparative examples respectively provide an organic electroluminescent device having the structure: ITO/HIL02(100nm)/NPB (40nm)/EM1(30nm)/TPBI (30nm)/LiF (0.5 nm)/Mg: ag (2: 8) (15nm)/CPL (70 nm).
The preparation process of the organic electroluminescent device is as follows:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent conductive layer (serving as an anode) in a cleaning agent, then washing the glass substrate in deionized water, ultrasonically removing oil in a mixed solvent of acetone and ethanol, baking the glass substrate in a clean environment until the water is completely removed, cleaning the glass substrate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cation beams to improve the surface property and improve the binding capacity with a hole injection layer;
placing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, performing vacuum evaporation on the anode to form HIL02 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100 nm;
carrying out vacuum evaporation on NPB (N-propyl bromide) on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
vacuum evaporating EM1 on the hole transport layer to serve as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
vacuum evaporating TPBI on the organic light-emitting layer to be used as an electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
vacuum evaporating 0.5nm LiF on the electron transport layer to form an electron injection layer;
and vacuum evaporating Mg/Ag on the electron injection layer to be used as a cathode, wherein the ratio of Mg to Ag is 2: 8, the thickness of the evaporation film is 15 nm;
CPL material was vacuum-deposited on the cathode to a thickness of 70 nm.
The organic electroluminescent devices of the examples and the comparative examples are prepared by the method, and the difference is only in the selection of the CPL material, which is detailed in Table 2.
And (4) performance testing:
the brightness and the current efficiency of the prepared organic electroluminescent device are measured by using a Hangzhou remote production OLED-1000 multichannel accelerated aging life and photochromic performance analysis system test, and the test results are shown in Table 2.
TABLE 2
| CPL material | Required luminance cd/m 2 | Current efficiency cd/A |
| H-1 | 1000 | 2.01 |
| H-2 | 1000 | 2.02 |
| H-3 | 1000 | 1.98 |
| H-4 | 1000 | 1.99 |
| 1 | 1000 | 2.56 |
| 82 | 1000 | 2.67 |
| 3 | 1000 | 2.68 |
| 4 | 1000 | 2.32 |
| 6 | 1000 | 2.65 |
| 13 | 1000 | 2.58 |
| 35 | 1000 | 2.59 |
| 44 | 1000 | 2.69 |
| 47 | 1000 | 2.77 |
As can be seen from the data in table 2 above, the compound provided by the present application can be used as a CPL material of an organic electroluminescent device to improve the luminous efficiency. Specifically, the current efficiency of the organic electroluminescent device prepared by the compound can reach more than 2.3cd/A, and some can reach more than 2.6 cd/A.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.
Claims (9)
1. A compound is characterized in that the structural formula of the compound is shown as a formula (I),
wherein m and n are selected from 0 or 1;
A、B、Ar 3 each independently selected from aromatic groups containing 6 to 40 carbon atoms, wherein hydrogen in the aromatic groups containing 6 to 40 carbon atoms can be substituted by R;
Ar 1 selected from the formula (II) in which R 1 ～R 10 At least one is absent and the corresponding one carbon atom is attached to the N atom or A in formula (I); x is selected from oxygen or sulfur;
Ar 2 one selected from the following structures A-1 to A-7 or a structure represented by a formula (II),
f, e are selected from 0 or 1, and at least one of them is selected from 1;
any one of SP2 hybridized with and bonded to only two carbon atoms of A-1 to A-7 may be bonded to N or B in formula (I) as a bonding site;
the hydrogen in A-1 to A-7 may be substituted by 1 or more R;
r and R 1 ～R 14 Independently selected from hydrogen, deuterium, F, CN, alkyl group containing 1-20 carbon atoms, alkoxy group containing 1-20 carbon atoms or aryl group containing 6-40 carbon atoms.
2. The compound of claim 1, wherein A, B, Ar is 3 Selected from the group consisting of benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene, and benzindenofluorene.
3. The compound of claim 1, wherein the aryl group having 6 to 40 carbon atoms is selected from the group consisting of benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzoanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene, and benzoindenofluorene.
4. The compound of claim 1, wherein the compound has the structure:
5. the compound of claim 4, wherein the compound has the structure:
6. a compound of claim 5, wherein R is 1 And R 10 Each independently selected from F, CN, methoxy, phenyl or biphenyl.
7. The compound of claim 1, wherein the compound is selected from one of structural formulas 1-162, and wherein the compounds of structural formulas 1-81 are as follows:
the compounds of the structural formulas 82-162 are respectively obtained by replacing O in the compounds of the structural formulas 1-81 with S.
8. An organic electroluminescent device, characterized in that it comprises a compound according to any one of claims 1 to 7.
9. A display apparatus comprising the organic electroluminescent device according to claim 8.
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| CN114957187A (en) * | 2021-02-24 | 2022-08-30 | 阜阳欣奕华材料科技有限公司 | Compound, organic electroluminescent device and display device |
| CN114957188A (en) * | 2021-02-26 | 2022-08-30 | 阜阳欣奕华材料科技有限公司 | Compound, organic electroluminescent device and intermediate compound |
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