CN115215842A - Compound, organic electroluminescent device and display device - Google Patents
Compound, organic electroluminescent device and display device Download PDFInfo
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- CN115215842A CN115215842A CN202110408904.8A CN202110408904A CN115215842A CN 115215842 A CN115215842 A CN 115215842A CN 202110408904 A CN202110408904 A CN 202110408904A CN 115215842 A CN115215842 A CN 115215842A
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- Prior art keywords
- compound
- carbon atoms
- organic electroluminescent
- electroluminescent device
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000000463 material Substances 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- -1 spirofluorene Chemical compound 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 claims description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- 238000001704 evaporation Methods 0.000 description 18
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001514 detection method Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940125846 compound 25 Drugs 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 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 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 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
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 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
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WCEBGEPQNMFINU-UHFFFAOYSA-N 5-bromo-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2C(OC3=CC=CC4=CC=CC2=C34)=C1 WCEBGEPQNMFINU-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KYFXEQHPAQBDRQ-UHFFFAOYSA-N OB(C(C=CC=C1)=C1C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=N1)O Chemical group OB(C(C=CC=C1)=C1C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=N1)O KYFXEQHPAQBDRQ-UHFFFAOYSA-N 0.000 description 1
- QHZHWFKZIRMHRT-UHFFFAOYSA-N [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 QHZHWFKZIRMHRT-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CNJGOTMNEZTZME-UHFFFAOYSA-N benzo[a]thianthrene Chemical compound C1=CC=CC=2C=CC=3SC=4C=CC=CC4SC3C21 CNJGOTMNEZTZME-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 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
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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Abstract
The present application relates to electroluminescent collarsDisclosed are 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, an organic electroluminescence (OLED) display technology has been applied to the fields of smart phones, tablet computers, and the like, and further, will be expanded to the large-size application field of televisions and the like. 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.
The selection of the hole layer, the light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency, the driving voltage and the lifetime 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 compound can be used as a main body material of an OLED (organic light emitting diode) light emitting device, and the obtained organic light emitting device has lower driving voltage and higher current efficiency, is particularly suitable for a red light emitting device or a green light emitting device, is used for reducing the driving voltage of the red light emitting device or the green light emitting device and improves the light emitting efficiency of the two devices.
In order to achieve the purpose, the application provides the following technical scheme:
the application provides a compound, which is shown as a formula (I),
wherein X is selected from O or S;
A. b is independently selected from aryl groups containing 6 to 40 carbon atoms consisting of carbon and hydrogen;
m and n are selected from 0 or 1;
Ar 1 、Ar 2 each independently selected from the group consisting of an aromatic group having 6 to 40 carbon atoms consisting of carbon and hydrogen, a nitrogen-containing aromatic group having 3 to 40 carbon atoms, and Ar 1 And Ar 2 One is an aromatic group containing 6 to 40 carbon atoms consisting of carbon and hydrogen, and the other is a nitrogen-containing aromatic group containing 3 to 40 carbon atoms;
the hydrogen in the compound shown in the formula (I) can be substituted by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and aryl containing 6-40 carbon atoms.
The position at which A is linked to the benzoxanthene skeleton and the position at which B is linked to the benzoxanthene skeleton are both specific linking positions, but Ar is a linking position 1 Connection of A, ar 2 The linkage of B and B is not particularly limited as long as the constituent structure of formula (1) retains a conjugated aromatic structure. In addition, composition Ar 1 、Ar 2 And any possible linkage between the aromatic groups of a and B are encompassed by the claims of the present application.
Further, ar 1 Or Ar 2 An aromatic group containing 6 to 40 carbon atoms consisting of a medium carbon and hydrogen, and A and B are each independently at least one selected from benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, ar 1 Or Ar 2 Wherein the nitrogen-containing aromatic group containing 3-40 carbon atoms is selected from pyridine, pyrimidine, triazine, imidazole, benzimidazole, naphthoimidazole, thiazole, benzothiazole, oxazole, benzoxazole, pyrazole, purine or aromatic heterocycle shown in formula (II);
wherein, in the formula (II), X 11 ～X 18 Selected from N or CR x And X 11 ～X 18 At least one is selected from N, R x Selected from H, alkyl groups containing 1 to 20 carbon atoms, aryl groups containing 6 to 40 carbon atoms, and X 11 ～X 18 At least one of them is selected from C. X 11 ～X 18 C in (3) is used for participating in forming a bond with B and A or a benzoxanthene and benzothianthrene mother ring.
Further, the compound is selected from one of the following formulas 1 to 228, wherein oxygen in benzoxanthene in the formulas 1 to 228 can be replaced by S;
further, the compound may be an isomer of any of the compounds represented by the formulae 1 to 228.
The following isomers are illustrated as follows:
for compound 50, the structure is as above, isomers thereof but including the single species are not limited to the following structure:
isomers of the compounds with other specific structures can be understood with reference to the above explanations.
In the above specific structures, each of the following benzoxanthene structures is included:
replacing the benzoxanthene structure with a benzothianthene structure:
the novel compounds formed are referred to as thios and are also included in the technical solution of the present application.
The present application also provides an organic electroluminescent device comprising a compound of the present application.
Further, the material of the electron transport layer of the organic electroluminescent device is the compound of the application.
Further, the host material of the light-emitting layer of the organic electroluminescent device is the compound.
Further, the organic electroluminescent device is a red device.
Further, the organic electroluminescent device is a red phosphorescent device.
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 formula (I) is prepared by taking benzoxanthene or benzothianthene as a mother nucleus, limiting each substituent to be substituted at the position of the benzoxanthene or benzothianthene, and limiting a specific substituent group for improving the material performance, so that an organic electroluminescent device prepared by using the compound has higher luminous efficiency, lower driving voltage and longer service life.
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 obtained by a person of ordinary skill in the art based on the embodiments in the present application without making any creative effort belong to 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 new embodiments, 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" indicates that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is only a shorthand representation of the combination of these numbers. 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, individual reactions or operational 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.
A synthetic route to a compound of formula (I-A):
a synthetic route for a compound represented by the formula (I-B):
specific synthesis examples:
(1) Synthesis of intermediate M-703
Adding 50 ml of DMF (dimethyl formamide) and 2.97 g (0.01 mol) of 8-bromobenzo [ kl ] xanthene into a 250 ml three-neck flask, controlling the temperature to be 20-25 ℃, adding 2.25 g (0.01 mol) of N-iodosuccinimide (NIS) in batches under stirring, controlling the temperature to be 20-25 ℃ for reacting for 2 hours, heating to be 40-45 ℃ for reacting for 1 hour, heating to be 60 ℃ for reacting for 1 hour, cooling, adding water and dichloromethane for separating, washing an organic layer with water, separating by silica gel column chromatography, and eluting with petroleum ether to obtain 1.8 g of a compound shown in M-703.
Mass spectrometric detection of the compound of formula M-3, with the largest two peaks at 422, 424, determined the product molecular formula: c 16 H 8 BrIO。
The compound shown as the formula M-703 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), 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-704
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 4.23 g (0.01 mol) of the compound shown in M-703, 1.22 g (0.01 mol) of phenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetrakistriphenylphosphine palladium, slowly heating to 60 ℃ for reaction for 8 hours, cooling, adding water for liquid separation, washing an organic layer with water, adding magnesium sulfate and a small amount of 200-300-mesh silica gel for drying, filtering to remove the magnesium sulfate and the silica gel, removing the solvent under reduced pressure, and recrystallizing the obtained solid with a mixed solvent of chlorobenzene and methanol for 2 times to obtain 3.1 g of the compound shown in M-704.
The compound shown in M-704 is subjected to mass spectrum detection, 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-705
Synthesis method reference was made to the synthesis of M-704 except that phenylboronic acid was changed to 3-phenylboronic acid to give the compound shown as M-705.
The compound shown in M-704 is detected by mass spectrometry, the maximum two peaks are 448 and 450, and the molecular formula of the product is determined as follows: c 28 H 17 BrO。
Synthesis example 1 Synthesis of Compound 1
A 500 ml three-neck flask, under nitrogen protection, 100 ml dioxane and 20 ml water are added, 3.73 g (0.01 mol) of the compound represented by M-704, 3.53 g (0.01 mol) of 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetratriphenylphosphine palladium are added, the mixture is slowly heated to reflux reaction for 12 hours, the temperature is reduced, water is added, the obtained solid is filtered, after drying under reduced pressure, the solid is separated by silica gel column chromatography, and petroleum ether: dichloromethane: ethyl acetate =9:1:0.1 Elution (vol/vol) gave 5.1 g of Compound 1.
Compound 1 was detected by mass spectrometry, m/z:601.
synthesis example 2 Synthesis of Compound 25
Reference Compound 1 was synthesized by simply replacing 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid with (4 '- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) - [1,1' -biphenyl ] -4-yl) phenylboronic acid to give compound 25.
Compound 25 was detected by mass spectrometry, m/z:677.
synthesis example 3 Synthesis of Compound 37
Reference Compound 1 was synthesized by simply changing 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid therein to a compound represented by M-37-1 and changing M-704 therein to a compound represented by M-705 to give Compound 37.
Compound 37 was detected by mass spectrometry, m/z:753.
synthesis example 4 Synthesis of Compound 112
(1) Synthesis of intermediate M-706
The synthesis of reference M-704 was performed by simply replacing the phenylboronic acid with (4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid to give intermediate M-706.
Performing mass spectrum detection on the intermediate M-706, determining that the maximum two peaks are 603 and 605, and determining that the molecular formula of the product is C 37 H 22 BrN 3 O。
(2) Synthesis of Compound 112
Synthesis procedure reference was made to the synthesis of Compound 1 except that M-704 was changed to M-706 and 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was changed to phenylboronic acid to give compound 112.
Compound 112 was detected by mass spectrometry, m/z:601.
the synthesis of products not shown in the above synthesis examples can be achieved by conventional methods according to methods known in the art.
The embodiment of the device comprises:
the specific structures of several materials used in this application are as follows:
synthesis of D-1:
referring to the synthesis of Compound 1 in example 1 except for replacing M-4 therein with 8-bromobenzo [ kl ] xanthene, the compound represented by D-1 was obtained.
Mass spectrometric detection of compound D-1, m/z:525.
synthesis of D-2:
referring to the synthesis of D-1, except that 8-bromobenzo [ kl ] xanthene was replaced by 9-bromobenzo [ kl ] xanthene, the compound represented by D-2 was obtained.
Mass spectrometric detection of compound D-2, m/z:525.
synthesis of D-4
Referring to the synthesis of D-1, except that 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was replaced with (4- (4, 6-bis ([ 1,1' -biphenyl ] -4-yl) -1,3, 5-triazin-2-yl) phenyl) phenylboronic acid, the compound represented by D-4 was obtained.
The mass spectrum detection is carried out on the compound D-4, and the mass spectrum detection ratio of m/z:601.
device example 1
The compound of the present application was selected as an electron transport material in an organic electroluminescent device in the examples, and D-1 to D4 were selected as an electron transport material in an organic electroluminescent device in the comparative examples.
The organic electroluminescent device has the following structure: ITO/HIL02 (100 nm)/HT (40 nm)/EM 1 (30 nm)/electron transport material (30 nm)/LiF (0.5 nm)/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 100nm;
vacuum evaporation plating HT on the hole injection layer as a hole transmission layer, wherein the evaporation plating rate is 0.1nm/s, and the evaporation plating film thickness is 40nm;
vacuum evaporating EM1 on the hole transport layer to be used as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
respectively carrying out vacuum evaporation on the organic light-emitting layer to form a comparison compound and the compound of the invention as an electron transport layer of an organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm and Al with the thickness of 150nm are evaporated 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
| Electron transport material | Required luminance cd/m 2 | Drive voltage V | Current efficiency cd/A |
| D-1 | 1000 | 6.22 | 1.46 |
| D-2 | 1000 | 6.18 | 1.56 |
| D-3 | 1000 | 6.77 | 1.65 |
| D-4 | 1000 | 6.19 | 1.58 |
| 1 | 1000 | 5.62 | 2.3 |
| 1S | 1000 | 5.51 | 2.52 |
| 2 | 1000 | 5.31 | 1.82 |
| 25 | 1000 | 4.99 | 2.23 |
| 37 | 1000 | 5.68 | 2 |
| 53 | 1000 | 5.76 | 1.96 |
| 62 | 1000 | 5.82 | 1.73 |
| 85 | 1000 | 5.07 | 1.61 |
| 98 | 1000 | 5.3 | 2.13 |
| 100 | 1000 | 5.44 | 1.77 |
| 107 | 1000 | 5.35 | 2.2 |
| 112 | 1000 | 4.98 | 2.13 |
| 164 | 1000 | 4.22 | 1.88 |
| 211 | 1000 | 4.59 | 1.59 |
| 218 | 1000 | 4.36 | 1.66 |
| 223 | 1000 | 3.65 | 1.81 |
| 224 | 1000 | 3.88 | 1.69 |
| 225 | 1000 | 3.66 | 2.17 |
As can be seen from the data in table 1, compared with the comparative example, the organic electroluminescent device prepared by using the compound of the embodiment of the present application has significantly reduced driving voltage, significantly improved current efficiency, and particularly significantly reduced voltage of 223 to 225, and more outstanding effect.
Device example 2
In the examples, the compound of the present application was selected as the red host material in the organic electroluminescent device, and in the comparative examples, D-1 to D4 were selected as the red host material in the organic electroluminescent device.
The structure of the organic electroluminescent device is as follows: ITO/NPB (20 nm)/Red host material (35 nm): ir (piq) 3[10% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein "Ir (piq) 3," 10% "" means the doping ratio of the red dye, i.e., the weight part ratio of the red host material to Ir (piq) 3 is 100.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, vacuum evaporating a hole transport layer NPB on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20nm;
vacuum evaporating a red light main body material and a dye Ir (piq) 3 on the hole transport layer to be used as a light emitting layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 35nm;
sequentially vacuum evaporating an electron transport layer TPBI and an electron transport layer Alq3 on the light-emitting layer, wherein the evaporation rates are both 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
and (3) evaporating 0.5nm LiF and 150nm Al on the electron transport layer in vacuum to form an electron injection layer and a cathode.
All organic electroluminescent devices are prepared by the method, the difference is only in the selection of red light main body materials, and the specific details are shown in the following table 2.
And (4) performance testing:
the brightness, the driving voltage 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 the following table.
TABLE 2
As can be seen from the above table, compared to the comparative compound, the compound provided by the present application as the red host material of the organic electroluminescent device can improve the light emitting efficiency and reduce the driving voltage.
It will be apparent to those skilled in the art that various changes and modifications can 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 (10)
1. A compound, wherein the compound is represented by formula (I),
wherein X is selected from O or S;
A. b is independently selected from aryl groups containing 6 to 40 carbon atoms consisting of carbon and hydrogen;
m and n are selected from 0 or 1;
Ar 1 、Ar 2 independently selected from an aromatic group having 6 to 40 carbon atoms consisting of carbon and hydrogen, a nitrogen-containing aromatic group having 3 to 40 carbon atoms, and Ar 1 And Ar 2 One is an aromatic group containing 6 to 40 carbon atoms consisting of carbon and hydrogen, and the other is a nitrogen-containing aromatic group containing 3 to 40 carbon atoms;
the hydrogen in the compound shown in the formula (I) can be substituted by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and aryl containing 6-40 carbon atoms.
2. The compound of claim 1, wherein Ar 1 Or Ar 2 An aromatic group containing 6 to 40 carbon atoms consisting of a medium carbon and hydrogen, and A and B are each independently at least one selected from benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
3. The compound of claim 1, wherein Ar 1 Or Ar 2 Wherein the nitrogen-containing aromatic group containing 3-40 carbon atoms is selected from pyridine, pyrimidine, triazine, imidazole, benzimidazole, naphthoimidazole, thiazole, benzothiazole, oxazole, benzoxazole, pyrazole, purine or aromatic heterocycle shown in formula (II);
wherein, in the formula (II), X 11 ～X 18 Selected from N or CR x And X 11 ～X 18 At least one is selected from N, R x Selected from H, alkyl groups containing 1 to 20 carbon atoms, aryl groups containing 6 to 40 carbon atoms, and X 11 ～X 18 At least one of them is selected from C.
4. The compound of claim 1, wherein the compound is selected from the group consisting of formulas 1 to 228, wherein the oxygen in benzoxanthene in formulas 1 to 228 is replaced by S;
5. the compound of claim 4, wherein the compound is an isomer of any of the compounds represented by formula 1 to 228.
6. An organic electroluminescent element comprising the compound according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the compound is an electron transport layer material or a host material of a light emitting layer.
8. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device is a red device.
9. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device is a red phosphorescent device.
10. A display device comprising the organic electroluminescent element as claimed in any one of claims 6 to 9.
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| US20150001479A1 (en) * | 2013-07-01 | 2015-01-01 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
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| CN114907281A (en) * | 2022-06-06 | 2022-08-16 | 吉林省元合电子材料有限公司 | Organic photoelectric functional material containing special-shaped fluorene structure and application thereof |
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