CN114478562A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN114478562A CN114478562A CN202011149103.6A CN202011149103A CN114478562A CN 114478562 A CN114478562 A CN 114478562A CN 202011149103 A CN202011149103 A CN 202011149103A CN 114478562 A CN114478562 A CN 114478562A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000010410 layer Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- -1 cyano, hydroxy Chemical group 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 150000003252 quinoxalines Chemical class 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- 239000012300 argon atmosphere Substances 0.000 description 19
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BBCAQPYJVYMQFB-UHFFFAOYSA-N sodium;2-methylpropane Chemical compound [Na+].C[C-](C)C BBCAQPYJVYMQFB-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- QXBWTYBCNFKURT-UHFFFAOYSA-N (2-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=CC=C1B(O)O QXBWTYBCNFKURT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WXNQFIBYBUTLFH-UHFFFAOYSA-N 1-(trifluoromethylsulfonyl)dibenzofuran Chemical compound FC(S(=O)(=O)C1=CC=CC=2OC3=C(C21)C=CC=C3)(F)F WXNQFIBYBUTLFH-UHFFFAOYSA-N 0.000 description 1
- DFUGYZQSDFQVPU-UHFFFAOYSA-N 1-benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=COC2=C1 DFUGYZQSDFQVPU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I. The compound has a polycyclic aromatic hydrocarbon structure, specifies the types of substituent groups on a parent nucleus, can be used as a blue fluorescent main body material or a blue phosphorescent main body material, is applied to an organic electroluminescent device, and can enable the device to have high luminous efficiency and long service life.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
Organic Electroluminescence (EL) is an electric energy excited organic material to emit light, which was discovered as early as 50 years ago, but until the appearance of Organic Light Emitting Diodes (OLEDs) in 1987, the phenomenon of electroluminescence has not received much attention. Briefly, the OLED is a device for generating electroluminescence by using a multi-layer organic thin film structure, which is easy to manufacture, requires a very low driving voltage, and has excellent display characteristics and qualities such as self-luminescence, wide viewing angle, high efficiency, wide color gamut, and flexible display, compared to a Liquid Crystal Display (LCD), and thus has become a mainstream flat panel display of a new generation.
The OLED functional material with high performance is selected and reasonably matched, so that the comprehensive characteristics of high efficiency, long service life and low voltage of the device are exerted. Materials constituting the organic material layer, such as hole transport materials, light emitting materials, electron transport materials, etc., should have characteristics of having fluorescence with higher efficiency in the visible light region, having higher conductivity, and exhibiting good semiconductor characteristics; has good film forming property, and the formed film has better uniformity and the like.
In recent years, due to rapid development of OLED devices, requirements for device performance are gradually increased, however, the types of existing organic electroluminescent materials are few, and the performance of the devices, such as efficiency and lifetime, cannot meet the requirements at present.
CN1701111A discloses a material for an organic electroluminescent device comprising a compound in which a nitrogen-containing heterocyclic group is attached to an aryl carbazolyl group or a carbazolylalkylene group, and an organic electroluminescent device comprising a cathode, an anode and an organic thin film layer comprising at least one layer and located between the cathode and the anode, wherein at least one of the organic thin film layers comprises the above-mentioned material for an organic electroluminescent device. The material can provide an organic electroluminescent device emitting blue light of high color purity. However, the device has a problem of low lifetime and needs to be further improved.
CN101193842A discloses a biphenyl derivative having a specific structure and an organic electroluminescent device in which an organic thin film layer composed of one or more layers including at least a light-emitting layer is sandwiched between a cathode and an anode, and at least one of the layers contains the biphenyl derivative alone or as a component of a mixture, whereby an organic EL device having a long life can be provided. The invention provides devices with luminous efficiency and voltage that need to be further optimized.
Therefore, there is a need in the art to develop new organic electroluminescent compounds to improve the performance of devices.
Disclosure of Invention
The invention aims to provide a compound, in particular to an organic electroluminescent material, and particularly to a luminescent layer host material, wherein the compound can be used as a fluorescent host material or a phosphorescent host material and can obtain higher luminous efficiency and longer service life when being applied to a device.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
in the formula I, Ar is1And Ar2Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
in the formula I, Z1And Z2Each independently selected from CR1R2、O、S、SiR3R4Or N-L3-R5Any one of the above;
in formula I, ring a and ring B each independently have any one of the structures shown by formula C1, formula C2, or formula C3:
formula C1 is fused to the five-membered ring in formula I through chemical bond a, formula C2 is fused to the five-membered ring in formula I through chemical bond b or C, formula C3 is fused to the five-membered ring in formula I through chemical bond d, e or f;
y is selected from CR9R10、O、S、SiR11R12Or N-L4-R13Any one of the above;
said L1-L4Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;
the R is1-R13Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxyAny one of a group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;
Ar1、Ar2、R1-R13、L1-L4wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of halogen, cyano, hydroxyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl and C8-C30 arylalkenyl.
The invention provides a novel organic electroluminescent compound, which has a polycyclic aromatic hydrocarbon structure, specifies the types of substituent groups on a parent nucleus, has large conjugation stability and a rigid structure, is applied to an organic electroluminescent device, and can obtain higher luminous efficiency and longer service life.
In the present invention, "substituted group" means a selection range of substituents when a "substituted or unsubstituted" group is substituted, the number is not particularly limited as long as the requirement of a compound bond is satisfied, and exemplarily, 1, 2, 3, 4 or 5, and when the number of substituents is 2 or more, the 2 or more substituents may be the same or different.
In the present invention, halogen represents a chlorine atom, a fluorine atom, a bromine atom or the like.
In the present invention, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
In the present invention, the number of carbons in the C6-C30 aryl group may be specifically C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., including but not limited to the following groups such as naphthalene, anthracene, phenanthrene, pyrene, etc.;
in the present invention, the number of carbons of the aryloxy group C6-C30 may be specifically C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, and the like, including but not limited to the following groups: furan, benzofuran, dibenzofuran, and the like;
in the present invention, C8-C30 arylalkenyl refers to a group in which an aryl group and an alkenyl group are linked by a single bond, C8-C30 refers to the total carbon number of the group, and does not refer to the carbon number of the aryl group alone, and the carbon number of the C8-C30 arylalkenyl group may be specifically C3, C4, C5, C6, C7, C8, C9, and the like, including but not limited to the following groups: styryl, triphenylene, fluoranthene, pentacene, and the like;
in the present invention, the number of carbons in the C3-C30 heteroaryl group may be specifically C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, and the like, including but not limited to the following groups: carbazole, thiophene, indole, pyrimidine, and the like;
in the present invention, the number of carbons of the C1-C10 alkyl group may be specifically C2, C3, C4, C5, C6, C7, C8, C9, and the like, including but not limited to the following groups: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl, and the like;
in the present invention, the number of carbons of the C1-C10 alkoxy group may be specifically C2, C3, C4, C5, C6, C7, C8, C9, and the like, including but not limited to the following groups: methoxy, ethoxy, propoxy, and the like;
in the present invention, the number of carbons of the C1-C10 cycloalkyl group may be specifically C3, C4, C5, C6, C7, C8, C9, and the like, including but not limited to the following groups: cyclopropane, cyclobutane, cyclopentane, cyclohexane, etc.;
in the present invention, the number of carbons of the C1-C10 silyl group may be specifically C2, C3, C4, C5, C6, C7, C8, C9, and the like, including but not limited to the following groups: methylsilyl, ethylsilyl, dimethylsilyl, trimethylsilyl, and the like.
Preferably, the compound has any one of the structures shown in the following formulas I-1 to I-7:
in the formula I-1, R is6' having and R6The same selection range;
ar is1、Ar2、L1、L2、Z1、Z2、Y、R6-R8All have the same limitations as beforeAnd (5) determining the range.
Preferably, the compounds have the structures shown in formula I-1 to formula I-3.
Preferably, at least one of the rings a and B is a group of formula C3, preferably, only one and preferably, only one is a group of formula C3.
Preferably, Ar is1And Ar2Each independently selected from hydrogen or a substituted or unsubstituted C6-C30 aryl group, preferably hydrogen or any one of the following substituted or unsubstituted:
wherein the wavy line indicates the bond of the group;
Ar1and Ar2Wherein, the substituted groups are respectively and independently selected from C6-C30 aryl or C8-C30 aryl alkenyl, preferably any one or at least two combinations of phenyl, naphthyl, phenanthryl or styryl.
Preferably, Z is1And Z2Each independently selected from O, S or N-L3-R5Preferably O or S.
Preferably, in formula I-1, Z is1And Z2Are all O, or Z1And Z2Are both S.
Preferably, in formula I-1, Ar is1And Ar2At least one of which is a substituted or unsubstituted C6-C30 aryl group, preferably, only one of which is a substituted or unsubstituted C6-C30 aryl group.
Preferably, in formula I-1, Ar is1And Ar2And only one of them is selected from any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group;
Ar1and Ar2Wherein, the substituted groups are respectively and independently selected from C6-C30 aryl or C8-C30 aryl alkenyl, preferably any one or at least two combinations of phenyl, naphthyl, phenanthryl or styryl.
When the compound has a structure represented by the formula I-1, Z is preferred in the present invention1And Z2Are both O or Z1And Z2The fluorescent material is an S structure, and aromatic groups are further substituted on the basis, particularly aromatic groups with large conjugated structures, and the structure has large conjugated stability and a rigid structure, can be used as a blue fluorescent host material, and further improves the luminous efficiency and the service life of the device.
Preferably, in formula I-2 or formula I-3, Ar is1And Ar2Are all hydrogen.
Preferably, in formula I-2 or formula I-3, Y is N-L4-R13And/or, said Z1And Z2At least one term of the two is N-L3-R5。
Preferably, said R is5And R13Each independently selected from any one of hydrogen or substituted or unsubstituted C3-C30 heteroaryl, preferably substituted or unsubstituted triazine and derivative groups thereof, substituted or unsubstituted pyridine and derivative groups thereof, substituted or unsubstituted pyrimidine and derivative groups thereof, substituted or unsubstituted quinazoline and derivative groups thereof, substituted or unsubstituted quinoxaline and derivative groups thereof.
When the compound has a structure shown in formula I-2 or formula I-3, at least one N heteroatom is preferably contained, and the heteroaryl is substituted on the N heteroatom, the structure has a large conjugated stable system, can be used as a blue phosphorescent host material, and can enable a device to have higher luminous efficiency and longer service life.
Preferably, said R is5And R13Each independently selected from any one of the following groups:
wherein the wavy line indicates the bond of the group.
Preferably, R5And R13Wherein each of said substituted groups is independently selected from C6-C30 aryl, preferably phenyl.
Preferably, said L1-L4Each independently selected from a single bond or a substituted or unsubstituted C6-C30 arylene group, preferably any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, and a substituted or unsubstituted phenanthrylene group.
Preferably, the compound has any one of the following structures shown as M1 to M8:
the compounds of formula I provided by the present invention can be synthesized by methods conventional in the art, and thus the preparation method is not particularly limited, and the following representative synthetic routes are provided only by way of example:
wherein TMS represents a tetramethylsilane group, and Y represents a halogen. The method for preparing the compound of the present invention is not limited to the above method, and those skilled in the art can make routine adjustments according to the prior art.
The second purpose of the invention is to provide the application of the compound in the first purpose, wherein the compound is applied to an organic electroluminescent device, preferably used as a luminescent layer material, preferably a luminescent layer host material of the organic electroluminescent device.
The invention also aims to provide an organic electroluminescent device which comprises an anode, a cathode and an organic functional layer positioned between the anode and the cathode, wherein the organic functional layer contains the compound for one purpose.
Preferably, the organic functional layer includes a light-emitting layer containing the compound according to one of the objects.
Preferably, the organic functional layer further comprises any one or at least two of an electron transport layer, an electron blocking layer, an electron injection layer, a hole blocking layer or a hole transport layer.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel organic electroluminescent compound, which has a polycyclic aromatic hydrocarbon structure, specifies the types of substituent groups on a parent nucleus, can be used as a blue fluorescent main body material or a blue phosphorescent main body material, is applied to an organic electroluminescent device, and can ensure that the device has higher luminous efficiency and longer service life.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The following synthesis examples exemplarily provide several methods for preparing specific compounds, and compounds not providing the preparation methods are synthesized by similar methods, which are not described in detail, and those skilled in the art can synthesize compounds of the general formula provided by the present invention and compounds of the prior art by themselves without any difficulty.
The reagents used in the following synthesis examples were all commercially available and the test instrument used to characterize the structure of the compounds was Bruker DRX 400.
Synthesis of intermediate A-6:
in the above synthesis steps, Suzuki refers to an organic coupling reaction known in the art, Bromination refers to a Bromination reaction, Deprotection refers to a Deprotection reaction, and cyclization refers to a cyclization reaction.
(1) Synthesis of A-2
A dry flask was equipped with a magnetic stir bar under argon atmosphere to mix 1- ((trifluoromethyl) sulfonyl) dibenzo [ b, d ] furan (20.0g, 63.2mmol, 10 equivalents), benzofuran-3-ylboronic acid (1.13 g, 69.6mmol, 1.1 equivalents), potassium phosphate (33.6g, 158.1mmol, 2.5 equivalents), palladium acetate (0.3g, 1.3mmol, 0.02 equivalents) and 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (hos, 1.2g, 2.5mmol, 0.04 equivalents), add tetrahydrofuran (THF, 400mL) and water (100mL), and reflux the reaction overnight. The crude product was purified by column chromatography. The desired product was isolated as a colorless oil (15.0g, 52.8mmol, yield 83.3%).
(3) Synthesis of A-3
A-2(15.0g, 52.7mmol, 1.0 equiv.) was dissolved in a dry flask charged with dichloromethane (DCM, 150mL), N-bromosuccinimide (9.4g, 52.7mmol, 1.0 equiv.) was added, and the resulting mixture was stirred at room temperature overnight. The crude product was purified by filtration over alumina. The desired product was isolated as a colorless oil (16.2g, 44.3mmol, 84.1% yield).
(3) Synthesis of A-4
A dry flask was equipped with a magnetic stir bar under an argon atmosphere, A-3 copper iodide (0.3g, 1.3mmol, 0.03 equiv.), bis (triphenylphosphine) palladium (II) chloride (0.6g, 0.9mmol, 0.02 equiv.) and trimethylsilylacetylene (18.9mL, 133.8mmol, 3.0 equiv.) were mixed, triethylamine (500mL) was added, and the reaction mixture was refluxed overnight. The crude product was purified by column chromatography. The desired product was isolated as a white solid (13.6g, 35.7mmol, yield 80.1%).
(4) Synthesis of A-5
The oven dried flask was equipped with a magnetic stir bar, A-4(10.0g, 26.3mmol, 1.0 equiv.), potassium carbonate (0.7g, 5.3mmol, 0.2 equiv.). Methanol (100mL) was added and the reaction mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure. The residue was taken up in DCM (100mL) and washed twice with water (2X 50 mL). The organic phase was concentrated under reduced pressure. The desired product was obtained as a white solid (8.1g, 26.3mmol, yield 100%).
(5) Synthesis of A-6
An oven dried flask was charged with A-5(8.1g, 26.0mmol, 1.0 equiv.), platinum chloride (690mg, 2.6mmol, 0.1 equiv.) under an argon atmosphere. Toluene (500mL) was added and the reaction mixture was refluxed overnight. The crude product was purified by column chromatography. The desired product was isolated as a white solid (3.1g, 10.0mmol, yield 38.7%).
Synthesis of intermediate A-9:
(1) synthesis of A-7
(Methylsulfanylphenyl) boronic acid and 28g (87mmol) cesium carbonate were mixed in 200mL water and 200mL N, N-dimethylformamide. A further 0.71g (1.7mmol) of SPhos and 1.68g (1.7mmol) of Pd were added2(dba)3And the mixture was refluxed for 17 hours, cooled to room temperature, and after separation of the organic phase, washed with water (3 × 200mL) and 200mL brine, then dried over magnesium sulfate and reduced under reduced pressure. Pressurization gave a grey residue which was further purified by crystallization from heptane, yield: 5.9g (15.9mmol, 91% yield).
(2) Synthesis of A-8
To 30g (80mmol) of A-7 was added 60mL of acetic acid, and the mixture was cooled to 0 ℃. 18.2mL (160mmol) of 30% H was added dropwise2O2The solution was stirred for 16 hours. Adding Na2SO3Solution, organic phase was separated and solvent was removed under reduced pressure. Yield: 26g (65mmol, 80% yield).
(3) Synthesis of A-9
A mixture of 133g (230mmol) of A-8 and 200mL of trifluoromethanesulfonic acid was stirred at 50 ℃ for 3 days. 600 g (2.9mol) of potassium carbonate in 3 l of water are then added dropwise and stirred for 5 hours at 75 ℃. 500mL of toluene was added, and the mixture was stirred at room temperature overnight. The organic phase was separated and reduced under reduced pressure. The residue was further purified by column chromatography (heptane/DCM). Yield: 39g (117mmol, 52% yield).
Synthesis example 1 Synthesis of Compound M1
A-6(10.0g, 32.4mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-10(13.5g, 31.1mmol, 95.9% yield). A-10(13g, 28.4mmol), A-11(25.4g, 85.1mmol), (tris (dibenzylideneacetone) dipalladium (1.3g, 70.9mmol), toluene (150mL), 1, 4-dioxane (150mL) and water (150mL) were added to the flask under an argon atmosphere and refluxed overnight to give crude product M1(4g, 7.1mmol, 25% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ7.91(4H)，7.89(2H)，7.66(3H),7.59(1H),7.52(2H),7.51(2H)，7.41(1H)，7.39(4H)，7.38(2H)，7.32(2H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝156.5，150.6，146，138.4，137.2，136.4，133.1，130.9，129.2，129，128.8，127.9，127.9 127.6，127.4，125.6，124.7，123.9，123.3，122.3，120.9，117.7，111.5，106.4，106，96.2.
synthesis example 2 Synthesis of Compound M2
A-6(10.0g, 32.4mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-10(13.5g, 31.1mmol, 95.9% yield). A-10(13g, 28.4mmol), A-12(25.4g, 84mmol), (tris (dibenzylideneacetone) dipalladium (1.3g, 70.9mmol), toluene (150mL), 1, 4-dioxane (150mL) and water (150mL) were added to the flask under an argon atmosphere and refluxed overnight to give crude product M2(4g, 6.1mmol, 26% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8(2H)，7.92(1H),7.91(2H),7.89(2H),7.73(1H),7.66(2H),7.59(3H),7.58(1H),7.41(1H),7.39(2H),7.38(2H),7.32(2H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝156.5，150.6，146，137.2,136.4,134.2,133.1,132.7,130.9,129,128.8,128.2,128.1,128.1,127.7,127.4,126.2,126.1,125.6,124.7,123.9,123.3,122.3,117.7,111.5,106.4,106,96.2.
synthesis example 3 Synthesis of Compound M3
A-9(10.0g, 31.2mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-13(13.5g, 30.5mmol, 93.9% yield). A-13(13g, 28.4mmol), A-14(25.4g, 84mmol), (tris (dibenzylideneacetone) palladium (1.3g, 70.9mmol), toluene (150mL), 1, 4-dioxane (150mL) and water (150mL) were added to the flask under an argon atmosphere and refluxed overnight to give crude product M3(4g, 5.2mmol, 24% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.45(2H)，7.98(2H),7.91(2H),7.8(1H),7.78(1H),7.72(2H),7.64(2H),7.56(2H),7.53(1H),7.52(2H),7.5(2H),7.45(2H)，7.39(3H),7.3(1H),6.95(2H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝151.9，139.9，139.9，138.8，137.5，137.2，137.1，136.4，134，133.1，132.8，130.9，130.9，129，129，128.6，128.6，128.5，127.9，127.8，127.4，126.9，126.4，126.2，125.6，124.4，123.3，122.8，122.8，122.5，121.1.
synthesis example 4 Synthesis of Compound M4
A-9(10.0g, 31.2mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-13(13.5g, 30.5mmol, 93.9% yield). A-13(13g, 28.4mmol), A-15(25.4g, 84mmol), (tris (dibenzylideneacetone) dipalladium (1.3g, 70.9mmol), toluene (150mL), 1, 4-dioxane (150mL) and water (150mL) were added to the flask under an argon atmosphere and refluxed overnight to give crude product M4(4g, 5.2mmol, 24% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.93(2H)，8.32(1H)，7.98(1H)，7.88(2H)，7.82(1H)，7.8(1H)，7.79(1H)，7.78(1H)，7.71(2H)，7.53(1H)，7.52(2H)，7.51(4H)，7.5(2H)，7.41(2H)，7.25(4H)，7.12(1H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝151.9，142，140.9，139.9，138.8，137.1，135.4，134，133.4，133.3，130.9，129.6，129.5，129.2，129，128.3，127.9，127.6，127.2，126.6，126.4，126.3，126.2，126.1，125，124.4，124.3，123.3，123.3，122.8，122.7，122.6，122.5，122.4，121.5，121.1，119.5，119.1.
synthesis example 5 Synthesis of Compound M5
A-6(10.0g, 32.4mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-10(13.5g, 31.1mmol, 95.9% yield). A-13(13g, 28.4mmol), 2-chloroaniline (18.2g,142mmol), tert-butyl sodium (34.1g, 360mmol), 305mg (1.5mmol) palladium (II) acetylacetonate dissolved in 500mL toluene under an argon atmosphere was added to the flask to give A-17(8g, 19mmol, 80% yield). Finally A-17(8g, 19mmol), A-18 were dissolved in 200mL THF (containing 4.2g NaH) under nitrogen and stirred at room temperature for 12h to give the final product M5(8g, 10mmol, 92% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.16(1H)，8.12(1H)，8.06(1H)，8.05(1H)，7.89(1H)，7.8(1H)，7.79(2H)，7.66(3H)，7.63(1H)，7.59(2H)，7.51(2H)，7.5(1H)，7.49(1H)，7.42(1H)，7.41(1H)，7.38(1H)，7.32(1H)，7.29(2H)
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝161，156.5，156.5，155.8，149.3，146，146，133，132.3，131.8，129.2，129.2，128.7，128.5，128.3，127.7，127.5，127.5，127.4，126.6，125.5，124.7，124.6，123.9，123.3，121.4，120.4，119.8，118.9，117.2，111.8，111.5，111.5，109.5，107.6，107.1，106.4，106.4，12.9
synthesis example 6 Synthesis of Compound M6
A-9(10.0g, 31.2mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-13(13.5g, 30.5mmol, 93.9% yield). A-13(13g, 28.4mmol), 2-chloroaniline (18.2g,142mmol), tert-butyl sodium (34.1g, 360mmol), (305mg, 1.5mmol) palladium (II) acetylacetonate were added to the flask under an argon atmosphere and dissolved in 500mL of toluene to give A-19(8g, 18.2mmol, 75% yield). Finally A-19(8g, 19mmol), A-20 were dissolved in 200mL THF (containing 4.2g NaH) under nitrogen and stirred at room temperature for 12h to give final product M6(7g, 9.2mmol, 89% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.28(4H)，8.12(1H)，8.09(1H)，7.98(1H)，7.86(1H)，7.8(2H)，7.78(2H)，7.63(1H)，7.52(1H)，7.51(5H)，7.5(1H)，7.46(1H)，7.41(1H)7.29(1H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝172.2，172.2，170.7，142.5，142.4，138.4，138.3，136.1，134.7，134，133.5，131.2，131.1，130.9，129.8，129.2，127.5，126.6，126.4，126.2，124.4，124.3，123.8，122.8，122.6，121.4，121.3，121.1，119.8，118.7，110，109.5.
synthesis example 7 Synthesis of Compound M7
A-21(10.0g, 31.2mmol) and A-22 were dissolved in 200mL THF (containing 4.2g NaH) under nitrogen, and stirred at room temperature for 12h to give A-23(7.5g, 8.9 mmol). A-23(7.5g, 8.9mmol) and further iodine in THF (13.2g, 52mmol) were added to a flask containing 10mL of THF under an argon atmosphere to give product A-24(6.5g, 14.5 mmol). A-24(6.5g, 14.5mmol), 2-chloroaniline (18.2g,142mmol), tert-butyl sodium (34.1g, 360mmol), (305mg, 1.5mmol) palladium (II) acetylacetonate were added to the flask under an argon atmosphere and dissolved in 500mL of toluene to give M7(7g, 16.2mmol, 75% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.63(1H)，8.45(1H)，8.12(1H)，7.98(1H)，7.96(1H)，7.94(1H)，7.8(1H)，7.79(1H)，7.78(1H)，7.63(1H)，7.55(1H)，7.52(1H)，7.51(2H)，7.5(1H)，7.41(2H)，7.4(1H)，7.29(1H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝170.3，161.6，160.6，144.4，143.1，142.5，138.4，138.3，136.1，135.8，135.8，133.9，133.5，133，130.8，129.2，129.2，128.7，127.5，126.2，124.4，124.3，123.8，122.8，122.6，121.7，121.4，121.1，120.5，119.8，119.6，117.9，111.1，108.7，103，97.8.
synthesis example 8 Synthesis of Compound M8
A-9(10.0g, 31.2mmol) and then (13.2g, 52mmol) of iodine in THF were added to a flask containing 10mL of THF under an argon atmosphere to react to give product A-13(13.5g, 30.5mmol, 93.9% yield). A-13(13g, 28.4mmol), 2-chloroaniline (18.2g,142mmol), tert-butyl sodium (34.1g, 360mmol), (305mg, 1.5mmol) palladium (II) acetylacetonate were added to the flask under an argon atmosphere and dissolved in 500mL of toluene to give A-19(8g, 18.2mmol, 75% yield). Finally A-19(8g, 19mmol), A-24 were dissolved in 200mL THF (containing 4.2g NaH) under nitrogen and stirred at room temperature for 12h to give final product M8(7.5g, 8.9mmol, 87% yield).
Nuclear magnetic data:
1HNMR(CD3CN，400MHz，300K)δ8.51(1H)，8.45(1H)，8.16(1H)，8.12(1H)，8.06(1H)，7.98(1H)，7.86(1H)，7.8(2H)，7.79(1H)，7.78(2H)，7.67(2H)，7.63(1H)，7.52(1H)，7.51(2H)，7.5(1H)，7.41(1H)，7.29(1H).
13C NMR(CD3CN，101MHz，300K)δ[ppm]＝161，155.8，142.5，138.4，138.3，134.4，133，131.8，130.9，129.2，128.7，127.9，127.5，127.4，127.3，127.2，126.6，126.2，126.1，125.5，124.9，124.4，124.3，123.8，122.8，121.4，121.1，119.8，109.5，109.5，107.6.
examples 1 to 9, comparative examples 1 to 3
This embodiment provides a red organic electroluminescent diode (the light-emitting layer is a mixed phosphorescent host), and the organic electroluminescent device includes a following structure stacked in sequence: substrate/hole injection layer (HIL, HATCN, 5 nm)/hole transport layer (HTL, SpMA1, 125 nm)/electron blocking layer (EBL, SpMA3, 10 nm)/light emitting layer (EML, 35 nm)/optional hole blocking layer (HBL, ST2, 10 nm)/electron transport layer (ETL, ST2: LiQ 50%: 50%, 30 nm)/electron injection layer (ETL, LiQ, 1nm), and finally a cathode. The cathode is formed of an aluminum layer having a thickness of 100 nm. The materials of the light-emitting layer are detailed in table 1.
The preparation method of the organic electroluminescent diode comprises the following steps:
before coating, a glass plate coated with structured ITO (indium tin oxide) with a thickness of 50nm was subjected to an oxygen plasma treatment followed by an argon plasma treatment. These plasma treated glass plates form the substrate of the OLED and the functional layers are then deposited in sequence in a vacuum chamber by thermal vapor deposition.
Wherein the light-emitting dopant in the light-emitting layer is added to one or more host materials in a specific volume ratio by co-evaporation.
And (4) performance testing:
the following performance tests were performed for the organic electroluminescent diodes of the above examples and comparative examples:
(1) at 1000cd/m2The driving voltage, External Quantum Efficiency (EQE) and current efficiency were measured at the luminous density of (a).
(2) At 1000cd/m2The electroluminescence spectrum was measured at the luminous density of (a) and the CIE1931 color coordinates (CIEx and CIEy) were calculated therefrom.
(3) At 40mA/cm2The T95 lifetime (the time for the luminance to drop to 95% of its starting value in operation) of the device was measured at a current density of (1).
The test results are shown in table 1.
TABLE 1
As shown in the above table, the light-emitting layer comprises two or three materials, including a host material (host material) and a light-emitting dopant (emitter), and the ratio of M1: IC 3: TEG5 (72%: 25%: 3%) as an example means that the material M1 is present in the light-emitting layer at a volume ratio of 72%, IC3 is present at a volume ratio of 25%, and TEG5 is present at a volume ratio of 3%. The electron transport layer works the same.
As shown in Table 1, the compound provided by the invention can be used as a light-emitting main material of an organic electroluminescent device, so that the light-emitting efficiency of the device can be effectively improved (more than 62 cd/A), the driving voltage can be reduced (less than 3.4V), and the service life can be prolonged (more than 500 h).
Although the compound D1 used in comparative example 1 has the same core as that of the present application, the effect of the compound D1 having an arylamine group substituted on the core is significantly inferior to that of the examples, because the electron transport property of the arylamine group alone is inferior and the effect as a light-emitting host material is inferior to that of a strong electron-withdrawing group such as triazine or diazine.
TABLE 2 Material Structure
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A compound having the structure of formula I;
in the formula I, Ar is1And Ar2Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
in the formula I, Z1And Z2Each independently selected from CR1R2、O、S、SiR3R4Or N-L3-R5Any one of the above;
in formula I, ring a and ring B each independently have any one of the structures shown by formula C1, formula C2, or formula C3:
formula C1 is fused to the five-membered ring in formula I through chemical bond a, formula C2 is fused to the five-membered ring in formula I through chemical bond b or C, formula C3 is fused to the five-membered ring in formula I through chemical bond d, e or f;
y is selected from CR9R10、O、S、SiR11R12Or N-L4-R13Any one of the above;
said L1-L4Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;
the R is1-R13Each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar1、Ar2、R1-R13、L1-L4wherein each of said substituted groups is independently selected from the group consisting of halogen, cyano, hydroxy, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, C8-C30 arylalkenyl, or a combination of at least two thereof.
2. The compound of claim 1, wherein the compound has any one of the structures shown in formulas I-1 to I-7 below:
in the formula I-1, R is6' having and R6The same limitations apply;
ar is1、Ar2、L1、L2、Z1、Z2、Y、R6-R8All having the same limitations as defined in claim 1.
3. A compound according to claim 1 or 2, wherein at least one of ring a and ring B is a group of formula C3, preferably wherein only one and only one is a group of formula C3.
4. A compound of any one of claims 1-3, wherein Ar is1And Ar2Each independently selected from hydrogen or a substituted or unsubstituted C6-C30 aryl group, preferably hydrogen or any one of the following substituted or unsubstituted:
wherein the wavy line indicates the bond of the group;
Ar1and Ar2Wherein, the substituted groups are respectively and independently selected from C6-C30 aryl or C8-C30 aryl alkenyl, preferably any one or at least two combinations of phenyl, naphthyl, phenanthryl or styryl.
5. A compound according to any one of claims 2 to 4, wherein Z is1And Z2Each independently selected from O, S or N-L3-R5Preferably O or S;
preferably, in formula I-1, Z is1And Z2Are all O, or Z1And Z2Are all S;
preferably, in formula I-1, Ar is1And Ar2At least one of which is a substituted or unsubstituted C6-C30 aryl group, preferably, only one of which is a substituted or unsubstituted C6-C30 aryl group;
preferably, in formula I-2 or formula I-3, Ar is1And Ar2Are all hydrogen;
preferably, in formula I-2 or formula I-3, Y is N-L4-R13And/or, said Z1And Z2At least one item in the group is N-L3-R5。
6. A compound according to any one of claims 1 to 5 wherein R is5And R13Each independently selected from any one of hydrogen or substituted or unsubstituted C3-C30 heteroaryl, preferably substituted or unsubstituted triazine and derivative group thereof, substituted or unsubstituted pyridine and derivative group thereof, substituted or unsubstituted pyrimidine and derivative group thereof, substituted or unsubstituted quinazoline and derivative group thereof, substituted or unsubstituted quinoxaline and derivative group thereof;
preferably, said R is5And R13Each independently selected from any one of the following groups:
wherein the wavy line indicates the bond of the group;
preferably, R5And R13Wherein each of said substituted groups is independently selected from C6-C30 aryl, preferably phenyl.
7. A compound according to any one of claims 1 to 6 wherein L is1-L4Each independently selected from a single bond or a substituted or unsubstituted C6-C30 arylene group, preferably any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, and a substituted or unsubstituted phenanthrylene group.
8. The compound of claim 1, having any one of the following structures M1 to M8:
9. use of a compound according to any of claims 1 to 8 in an organic electroluminescent device, preferably as a light-emitting layer material, preferably a light-emitting layer host material, of said organic electroluminescent device.
10. An organic electroluminescent device comprising an anode, a cathode and an organic functional layer between the anode and the cathode, wherein the organic functional layer contains a compound according to any one of claims 1 to 8;
preferably, the organic functional layer comprises a light-emitting layer containing a compound according to any one of claims 1 to 8.
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Application publication date: 20220513 |