CN113354641B - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
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- CN113354641B CN113354641B CN202110626297.2A CN202110626297A CN113354641B CN 113354641 B CN113354641 B CN 113354641B CN 202110626297 A CN202110626297 A CN 202110626297A CN 113354641 B CN113354641 B CN 113354641B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims description 87
- 239000010410 layer Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000002560 nitrile group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 150000001975 deuterium Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 238000005538 encapsulation Methods 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 abstract description 6
- 239000013310 covalent-organic framework Substances 0.000 abstract 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 238000007725 thermal activation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 150000003254 radicals Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 101100317378 Mus musculus Wnt3 gene Proteins 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 4
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102000008016 Eukaryotic Initiation Factor-3 Human genes 0.000 description 4
- 108010089790 Eukaryotic Initiation Factor-3 Proteins 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 125000004431 deuterium atom Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- PCMKGEAHIZDRFL-UHFFFAOYSA-N 3,6-diphenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 PCMKGEAHIZDRFL-UHFFFAOYSA-N 0.000 description 3
- FHJJVSJWFYYPAC-UHFFFAOYSA-N 3-carbazol-9-yl-9h-carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C2NC3=CC=CC=C3C2=C1 FHJJVSJWFYYPAC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- ADKNEEZYAPNTPM-UHFFFAOYSA-N 1-azapentacyclo[10.7.1.02,7.08,20.014,19]icosa-2,4,6,8(20),9,11,14,16,18-nonaen-13-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC3=C2N1C1=CC=CC=C13 ADKNEEZYAPNTPM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- JGGSOWGJMBNDHS-UHFFFAOYSA-N 10-phenyl-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C1=CC=CC=C1 JGGSOWGJMBNDHS-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFJQWBKCAVSFQQ-UHFFFAOYSA-N BrC1=CC(I)=C(CSCC(C=CC(Br)=C2)=C2I)C=C1 Chemical compound BrC1=CC(I)=C(CSCC(C=CC(Br)=C2)=C2I)C=C1 LFJQWBKCAVSFQQ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- DAYOYSNRJMKALF-UHFFFAOYSA-N ethyl 4-bromo-2-iodobenzoate Chemical compound CCOC(=O)C1=CC=C(Br)C=C1I DAYOYSNRJMKALF-UHFFFAOYSA-N 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical class [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
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Abstract
The invention relates to an organic compound, which is a thermal activation delayed fluorescence type covalent organic framework material, and synthesizes a series of delayed fluorescence molecules containing phosphoryl or sulfonyl groups, wherein the molecules have higher stability and internal quantum efficiency and are suitable for being used as materials for organic electroluminescent elements. The invention also relates to application of the organic compound and a material containing the organic compound and used for an organic electroluminescent element. The material has the characteristics of low starting voltage, high luminous efficiency and high brightness.
Description
Technical Field
The invention belongs to the technical field of materials for organic electroluminescent elements, and particularly relates to an organic compound and a preparation method and application thereof.
Background
Due to the wide application prospect in the fields of smart phones, televisions, wearable displays and solid-state lighting, organic light-emitting diodes (OLEDs) have been widely researched and paid attention to in the scientific and industrial fields for decades. According to the statistical rule of quantum spin, the traditional fluorescent OLED device can utilize 25% of singlet excitons generated by electric excitation at most, and when the light output efficiency of the device is 20%, the maximum external quantum efficiency is generally not more than 5%. In order to improve the efficiency of OLED devices, how to effectively utilize the remaining 75% of triplet excitons of non-radiative transitions has become a major concern for researchers.
The discovery of phosphorescent electroluminescent devices is a milestone event in the history of OLED development, making 100% in-device quantum efficiency possible. Currently, devices employing phosphorescent materials of iridium, platinum, and other heavy metal complexes have achieved external quantum efficiencies in excess of 20%. However, due to the limited resource and high cost of the iridium, platinum and other noble metal phosphorescent materials, the development of an OLED device based on a triplet exciton utilization mechanism of a cheap pure organic material becomes a hot spot of current research. In recent years, OLED materials and devices based on a Thermally Activated Delayed Fluorescence (TADF) mechanism have attracted considerable attention from researchers. The organic micromolecule material with smaller energy level difference between the singlet excited state and the triplet excited state is utilized, and the triplet excitons can be converted into the singlet excitons through the reverse intersystem crossing process under the action of environmental heat energy, so that delayed fluorescence is emitted. The mechanism adopts pure organic micromolecular material without noble metal, so that the fluorescent device can effectively utilize the energy of triplet excitons, the external quantum efficiency of the device is close to or even reaches the level of a phosphorescent device, and the method has important significance for effectively saving resources, protecting the environment, reducing the production cost and realizing industrialization.
Currently, the external quantum efficiency of organic electroluminescent devices based on thermally activated delayed fluorescent materials has exceeded 25%, but due to their long delay lifetime, the devices exhibit a severe efficiency roll-off at high current densities. Therefore, in order to further improve the efficiency and stability of the device, the development of a new and efficient thermally activated delayed fluorescence material is currently an important challenge.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a novel organic compound which is a raw material for an organic electroluminescent element material, and which can provide an organic electroluminescent element material and an organic electroluminescent element having a reduced starting voltage, a high luminous efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic compound having the structure of formula (I):
wherein, W 1 ～W 4 Identically or differently representing N or CR 5 Or any two adjacent radicals W 1 、W 2 、W 3 、 W 4 Represents a group of the following formula (II) or (III),
wherein Z, identically or differently on each occurrence, denotes CR 6 Or N, and ^ indicates the corresponding adjacent group W in formula I 1 And W 2 、W 2 And W 3 Or W 3 And W 4 ；
T 1 Represents SO 2 Or CO;
T 2 representation O, S, NAr 3 Or CR 7 R 8 ；
L represents a single bond, or one of a sub-aromatic ring system or a sub-heteroaromatic ring system having 5 to 60 carbon atoms;
R 1 ～R 8 each, the same or different, is selected from hydrogen, deuterium, a compound having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 Branched or cyclic chains ofHetero alkyl group having C 2 ～C 40 Alkenyl or alkynyl group of (A), one of an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R 1 ～R 8 Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar 1 、Ar 2 、Ar 3 each of which is identical or different and is selected from aromatic or heteroaromatic ring systems having from 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R; ar (Ar) 1 And Ar 2 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 4 ) 2 、 N(R 9 ) 2 、C(＝O)Ar 4 、C(＝O)R 9 、P(＝O)(Ar 4 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 9 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 9 C＝CR 9 、C≡C、Si(R 9 ) 2 、Ge(R 9 ) 2 、Sn(R 9 ) 2 、C＝O、 C＝S、C＝Se、C＝NR 9 、P(＝O)(R 9 )、SO、SO 2 、NR 9 O, S or CONR 9 And wherein one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R may optionally be joined or condensed in formMono-or polycyclic, aliphatic, aromatic or heteroaromatic ring systems which may be interrupted by one or more radicals R 9 Substitution;
R 9 each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 4 ) 2 、 N(R 10 ) 2 、C(＝O)Ar 4 、C(＝O)R 10 、P(＝O)(Ar 4 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R 9 Each radical in (a) may be substituted by one or more radicals R 10 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 10 C＝CR 10 、C≡C、Si(R 10 ) 2 、Ge(R 10 ) 2 、Sn(R 10 ) 2 、C＝O、 C＝S、C＝Se、C＝NR 10 、P(＝O)(R 10 )、SO、SO 2 、NR 10 O, S or CONR 10 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 10 Substitution;
Ar 4 identical or different at each occurrence, from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be interrupted by one or more nonaromatic radicals R 10 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 4 Can also be selected from N (R) through a single bond 10 )、C(R 10 ) 2 Oxygen or sulfur bridging groups;
R 10 selected from hydrogenAtom, deuterium atom, fluorine atom, nitrile group, having C 1 ～C 20 An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R 10 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, wherein two or more adjacent substituents R 10 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Aromatic or heteroaromatic ring systems in the sense of the present invention are intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or an S atom. Thus, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains 5 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH 2 The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethyloctenyl, ethylheptenyl, cycloheptenyl, n-octyl, cyclooctenyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, or neopentylAlkynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentyloxy group, a sec-pentyloxy group, a 2-methylbutyloxy group, a n-hexyloxy group, a cyclohexyloxy group, a n-heptyloxy group, a cycloheptyloxy group, a n-octyloxy group, a cyclooctyloxy group, a 2-ethylhexyloxy group, a pentafluoroethoxy group and a 2,2, 2-trifluoroethoxy group. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone 2 The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present 2 The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R 10 Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene,Anthracene, benzanthracene, phenanthrene, pyrene,
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] indole, perylene, anthracene, phenanthrene, perylene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or a group derived from a combination of these systems.
Further, the formula (I) mainly comprises the following structures shown in formula (I) -1 to formula (I) -20:
wherein R is 1 ～R 5 、L、Ar 1 、Ar 2 And T 2 The definitions of (a) are the same as those described above.
Further, L is selected from a single bond, or groups represented by the following (1) to (18), or a combination thereof:
where the symbols used are as defined above and one dotted bond indicates the bond to the compound body and the other dotted bond indicates the bond to N.
Further, the-NAr 1 Ar 2 The structure of (1) mainly comprises the following steps:
wherein the symbols used are the same as defined above and the dashed bonds indicate bonding to L.
Further, the organic compound mainly comprises the following compounds represented by PP281 to PP 493:
the use of said organic compounds in materials for organic components.
Further, the organic compound is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
Further, the organic compound is applied to a luminescent layer material, an electron transporting/hole blocking layer material or an encapsulating layer material.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers disposed between the first electrode and the second electrode, at least one of the organic layers containing the organic compound.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particular preference is given to systems having three light-emitting layers, where the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, at least one of these layers comprises the organic compounds according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the electron transport layer and in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10 -5 Pa, preferablyLess than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10 -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A light-emitting device includes the organic electroluminescent element.
The material for organic devices of the present invention contains the organic compound of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The organic compound of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material, and in this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, an encapsulation layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that: the organic compound has high internal quantum efficiency and high glass transition temperature, and is suitable for being used as a material for an organic electroluminescent element. The material for organic electroluminescent elements containing the organic compound has the characteristics of low starting voltage, high luminous efficiency and high brightness. The organic compound of the present invention has excellent thermal stability and film-forming properties, and can be used for a material for an organic electroluminescent element, a display device, and a lighting device, and can prolong the service life thereof, thereby reducing the production cost of the material for an organic electroluminescent element, the display device, and the lighting device.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-luminescent layer, 6-hole transport/electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely a few embodiments of the invention, rather than a full embodiment, and are not to be construed as limiting the invention in any way. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without making any creative effort, shall fall within the protection scope of the present invention.
The following test instruments and methods for performance testing of OLED materials and devices in the examples are as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
The synthesis of the compound PP281 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
50.0mmol of indolo [3,2,1-de ] acridin-8-one is dissolved in 100mL of glacial acetic acid, 22.0mmol of potassium iodate and 33.0mmol of potassium iodide are added, the mixture is heated, refluxed, stirred and reacted for 3 hours, cooled to room temperature, filtered, and a filter cake is washed with water, sodium carbonate aqueous solution and water to obtain an intermediate Int-1 as a white solid with a yield of 93%.
The second step: preparation of Compound PP281
24.0mmol of intermediate Int-1 is dissolved in 80mL of xylene, under the protection of nitrogen, 20.0mmol of 3, 6-di-tert-butylcarbazole (CAS:37500-95-1), 80.0mmol of anhydrous potassium carbonate, 2.0mmol of cuprous iodide and 5.0mmol of N, N' -dimethylethylenediamine are added, the mixture is heated up, refluxed and stirred for reaction for 15 hours, cooled to room temperature, filtered, the filtrate is concentrated under reduced pressure to dryness, and separated and purified by a silica gel column to obtain a product PP281, a white solid with the yield of 92 percent, HRMS: 547.2763[ M + H] + 。
Example 2
Referring to the synthesis method of example 1, only 3, 6-di-tert-butylcarbazole in the second step of example 1 is replaced by corresponding amine, the mass and the amount of the compound are changed according to the molar weight, and other experimental parameters are correspondingly adjusted according to actual needs to prepare compounds PP282 to PP 302.
Example 3
Preparation of compound PP 368:
the first step is as follows: preparation of Compound Int-2
0.10mol of intermediate Int-1 and 0.12mol of pinacol diboron are dissolved in 80mL of DMF, and 0.15mol of anhydrous potassium acetate and 1.0mmol of PdCl are added under the protection of nitrogen 2 (dppf) as a catalyst, heating to 90 ℃, stirring for reacting for 8 hours, cooling to room temperature, adding 200mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-2 in white solid with the yield of 92%.
The second step is that: preparation of Compound PP368
20.0mmol of intermediate Int-2 was dissolved in 60mL of toluene, and 18.0mmol of 9- (3-bromophenyl) was added under nitrogen) -3, 6-di-tert-butylcarbazole, 80.0mmol of anhydrous potassium carbonate, 0.2mmol of Pd (PPh) 3 ) 4 Heating, refluxing and stirring the catalyst, 30mL of ethanol and 30mL of water, reacting for 10 hours, cooling to room temperature, adding 100mL of toluene and 50mL of water, separating an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a product PP368, a white solid, the yield of 87%, HRMS: 623.3078[ M + H] + 。
Example 4
Preparation of compounds PP367, PP 369-PP 401, referring to the synthesis method of example 3, only the 9- (3-bromophenyl) -3, 6-di-tert-butylcarbazole of the second step of example 3 is replaced by the corresponding halide, the mass and the amount of the compound are changed according to the molar weight, and other experimental parameters are correspondingly adjusted according to actual needs to prepare compounds PP367, PP 369-PP 401.
Example 5
Synthesis of Compound PP305, comprising the following steps:
the first step is as follows: preparation of Compound Int-3
50.0mmol of phenothiazine is dissolved in 100mL of xylene, under the protection of nitrogen, 60.0mmol of o-bromoiodobenzene, 0.15mol of anhydrous potassium carbonate, 5.0mmol of cuprous iodide and 15.0mmol of N, N' -dimethylethylenediamine are added, the mixture is heated, refluxed, stirred and reacted for 15 hours, cooled to room temperature, filtered, the filtrate is concentrated under reduced pressure to dryness, and is separated and purified by a silica gel column, so that an intermediate Int-3 is obtained, namely a yellow solid, and the yield is 87%.
The second step is that: preparation of Compound Int-4
25.0mmol of intermediate Int-3 is dissolved in 80mL of toluene, under the protection of nitrogen, 37.5mmol of sodium tert-butoxide, 0.2mmol of palladium acetate and 0.4mmol of Xanphos (CAS:161265-03-8) are added, the mixture is heated under reflux and stirred for reaction for 12 hours, the mixture is cooled to room temperature, 50mL of water is added, ethyl acetate is used for extraction, an organic phase is collected, the organic phase is dried and filtered, and the filtrate is concentrated under reduced pressure and dried and is separated and purified by a silica gel column, so that the compound Int-4 is obtained, yellow solid and the yield is 82%.
The third step: preparation of Compound Int-5
20.0mmol of intermediate Int-4 is dissolved in 100mL of dichloromethane, the temperature is reduced by using an ice-water bath, 65.0mmol of M-chloroperoxybenzoic acid (85%) is added in batches, the mixture is stirred and reacted for 12 hours at room temperature, the mixture is filtered, filtrate is washed by 1M sodium bicarbonate aqueous solution and washed by water, an organic phase is collected, the organic phase is dried and filtered, the filtrate is decompressed, concentrated and dried, and is separated and purified by using a silica gel column, so that a compound Int-5 is obtained, white solid is obtained, and the yield is 92%.
The fourth step: preparation of Compound Int-6
Referring to the first synthesis step of example 1, intermediate Int-6 was prepared in 90% yield as a white solid by replacing only indolo [3,2,1-de ] acridin-8-one of the first step of example 1 with intermediate Int-5.
The fifth step: preparation of Compound PP305
Referring to the synthesis procedure of the second step of example 1, compound PP305 was prepared as a white solid in 94% yield from replacing only Int-1 in the second step of example 1 with intermediate Int-6 and 3, 6-di-tert-butylcarbazole with 3, 6-diphenylcarbazole (CAS:56525-79-2), HRMS: 623.1809[ M + H] + 。
Example 6
Referring to the synthesis method of example 5, only 3, 6-diphenylcarbazole in the fifth step of example 5 is replaced by corresponding amine, the mass and the amount of the compound are changed according to the molar weight, and other experimental parameters are correspondingly adjusted according to actual needs to prepare compounds PP303, PP304 and PP306 to PP 330.
Example 7
Preparation of compound PP 366:
the first step is as follows: preparation of Compound Int-7
Referring to the first step synthesis of example 3, intermediate Int-7 was prepared in 93% yield as a white solid by replacing only Int-1 in the first step of example 3 with intermediate Int-6.
The second step is that: preparation of Compound Int-8
20.0mmol of intermediate Int-7 is dissolved in 60mL of toluene, and 20.0mmol of p-bromoiodobenzene, 60.0mmol of anhydrous sodium carbonate and 0.1mmol of Pd (PPh) are added under nitrogen protection 3 ) 4 Heating, refluxing and stirring the catalyst, 30mL of ethanol and 30mL of water for reaction for 10 hours, cooling to room temperature, adding 100mL of toluene and 50mL of water, separating an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-8 with a white solid yield of 85%.
The third step: preparation of Compound PP366
24.0mmol of intermediate Int-8 are dissolved in 80mL of toluene and 20.0mmol of 5, 10-dihydro-5-phenylphenazine (CAS: 49662-1) are added under nitrogen7-1), 30.0mmol of sodium tert-butoxide, 0.1mmol of Pd 2 (dba) 3 And (2) heating, refluxing and stirring the catalyst and 0.2mmol of Xanphos for reaction for 10 hours, cooling to room temperature, adding 50mL of toluene and 50mL of water, separating an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a product PP366, a white solid with the yield of 89%, HRMS: 638.1920[ M + H] + 。
Example 8
Preparation of compounds PP331 to PP365 referring to the synthesis method of example 7, only 5, 10-dihydro-5-phenylphenazine in the third step of example 7 was replaced with corresponding amine, the mass and amount of the compound was changed according to the molar amount, and other experimental parameters were adjusted accordingly according to actual needs to prepare compounds PP331 to PP 365.
Example 9
Synthesis of Compound PP405, comprising the following steps:
the first step is as follows: preparation of Compound Int-9
Under the protection of nitrogen, 0.10mol of 1-fluorocarbazole and 0.12mol of 2-thiophenol-1-iodonaphthalene are dissolved in 150mL of dry xylene, then 0.30mol of anhydrous potassium carbonate, 10.0mmol of cuprous iodide and 30.0mmol of N, N' -dimethylethylenediamine are added, the mixture is heated, refluxed, stirred and reacted for 12 hours, cooled to room temperature, filtered, decompressed, concentrated and dried in a vacuum manner, and separated and purified by a silica gel column to obtain a compound Int-9 which is a yellow solid with the yield of 88%.
The second step is that: preparation of Compound Int-10
Under the protection of nitrogen, 20.0mmol of Int-9 is dissolved in 60mL of dry DMF, the temperature is reduced to 0 ℃, 24.0mmol of sodium hydride (60% oil dispersion) is added, the mixture is stirred and reacted for 1 hour, the temperature is raised to room temperature and the mixture is stirred and reacted for 10 hours, the reaction liquid is poured into 200mL of ice water, the mixture is filtered, a filter cake is washed by water, and the mixture is separated and purified by a silica gel column to obtain the compound Int-10, yellow solid and the yield is 58%.
The third step: preparation of Compound Int-11
Referring to the preparation process of the third step in example 5, intermediate Int-11 was prepared in a white solid with a yield of 91% by replacing only Int-4 of the third step in example 5 with intermediate Int-10 prepared in the previous step.
The fourth step: preparation of Compound Int-8
Referring to the preparation process of the third step in example 1, intermediate Int-12 was prepared as a white solid with a yield of 87% by merely replacing Int-2 of the third step in example 1 with intermediate Int-11 prepared in the previous step.
The fifth step: preparation of Compound PP405
20.0mmol of intermediate Int-12 is dissolved in 80mL of toluene, and 18.0mmol of 3, 9' -bicarbazole (CAS:18628-07-4), 30.0mmol of sodium tert-butoxide, 0.05mmol of Pd are added under nitrogen protection 2 (dba) 3 Heating the catalyst and 0.1mmol of Xanphos, refluxing and stirring for reaction for 10 hours, cooling to room temperature, adding 50mL of toluene and 50mL of water, separating an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a product PP405, a white solid with the yield of 92 percent, HRMS: 686.1918[ M + H] + 。
Example 10
Referring to the synthesis method of example 9, 3, 9' -bicarbazole obtained in the fifth step of example 9 is replaced with corresponding amine, the mass and the amount of the compound are changed according to the molar weight, and other experimental parameters are adjusted according to actual needs to prepare compounds PP402 to PP404 and PP406 to PP 436.
Example 11
The synthesis of the compound PP477 comprises the following steps:
the first step is as follows: preparation of Compound Int-13
Under the protection of nitrogen, 50.0mmol of 3-bromocarbazole and 60.0mol of 4-bromo-2-iodobenzylsulfide are dissolved in 100mL of dry xylene, 150.0mmol of anhydrous potassium carbonate, 5.0mmol of cuprous iodide and 15.0mmol of N, N' -dimethylethylenediamine are added, the mixture is heated, refluxed and stirred for reaction for 12 hours, cooled to room temperature, filtered, the filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column, so that the compound Int-13 is obtained, namely a yellow solid, and the yield is 93%.
The second step is that: preparation of Compound Int-14
Dissolving 20.0mmol of Int-13 in 40mL of acetonitrile and 40mL of dichloromethane, cooling to 0 ℃, adding 2.0mmol of vanadium pentoxide, adding 24.0mmol (50%) of hydrogen peroxide, stirring for reaction for 1 hour, heating to 10 ℃, stirring for reaction for 1 hour, adding 200mL of ice water, extracting with dichloromethane, collecting an organic phase, washing with saturated sodium bisulfite aqueous solution, washing with water, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound Int-14, namely a white solid, wherein the yield is 85%.
The third step: preparation of Compounds Int-15 and Int-15
Under the protection of nitrogen, 55mL of concentrated sulfuric acid is cooled to 0 ℃, 40.0mmol of Int-14 is added in batches, the mixture is stirred and reacted for 1 hour, the mixture is heated to room temperature and stirred and reacted for 2 hours, the reaction liquid is poured into 200g of crushed ice, anhydrous potassium carbonate solid is added in batches to be adjusted to be alkaline, dichloromethane is used for extraction, an organic phase is collected and dried, the filtrate is concentrated under reduced pressure and dried, and then silica gel column separation and purification are carried out, so that a compound Int-15 is obtained, white solid is obtained, the yield is 65%, and the compound Int-15' is obtained, and the yield is 27%.
The fourth step: preparation of Compound Int-16
Referring to the preparation process of the third step in example 5, intermediate Int-16 was prepared as a white solid with a yield of 95% by replacing only Int-4 of the third step in example 5 with intermediate Int-15 prepared in the previous step.
With reference to the same synthetic method described above, the following intermediates were prepared:
the fifth step: preparation of Compound PP477
20.0mmol of intermediate Int-16 was dissolved in 80mL of toluene and 48.0mmol of 9, 10-dihydro-9, 9-dimethylacridine (CAS:53884-62-1), 60.0mmol of sodium tert-butoxide, 0.1mmol of Pd were added under nitrogen 2 (dba) 3 Catalyst and 0.2mL of 10% tert-butyl phosphorus toluene solution are heated to 100 DEG CThe reaction was stirred for 10 hours, cooled to room temperature, 50mL of toluene and 50mL of water were added, the organic phase was separated, dried, filtered, the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column separation to give the product PP477 as a white solid in a yield of 76%, HRMS: 720.2702[ M + H] + 。
Example 12
Preparation of Compounds PP437 to PP476, PP478, PP479, PP492 and PP493 with reference to the synthetic method of example 11, only Int-16 in the fifth step of example 11 was replaced with the corresponding intermediate prepared in the fourth step, only 9, 10-dihydro-9, 9-dimethylacridine in the fifth step of example 11 was replaced with the corresponding amine, the mass amount of the compound was changed according to the molar amount, and other experimental parameters were adjusted as necessary to prepare Compounds PP437 to PP476, PP478, PP479, PP492 and PP 493.
Example 13
The synthesis of the compound PP486 comprises the following steps:
the first step is as follows: preparation of Compound Int-20
Referring to the first preparation step of example 11, intermediate Int-20 was prepared in a yield of 68% as a yellow solid by replacing only 4-bromo-2-iodobenzylsulfide of the first step of example 11 with ethyl 4-bromo-2-iodobenzoate (CAS: 1261646-75-6).
The second step is that: preparation of Compound Int-21
20.0mmol of Int-20 is dissolved in 40mL of THF and 40mL of water, 0.1mol of sodium hydroxide is added, the mixture is heated and refluxed for reaction for 5 hours, the mixture is cooled to room temperature, 100mL of water is added, THF is removed by concentration under reduced pressure, concentrated hydrochloric acid is added dropwise to adjust the mixture to acidity, the mixture is filtered, and the filter cake is washed with water to obtain the compound Int-21 as a white solid with a yield of 92%.
The third step: preparation of Compound Int-22
Under the protection of nitrogen, 55mL of concentrated sulfuric acid is cooled to 0 ℃, 4.0mmol of boric acid is added, 40.0mmol of Int-21 is added in batches, the mixture is stirred and reacted for 2 hours, the temperature is raised to 40 ℃, the mixture is stirred and reacted for 2 hours, the mixture is cooled to room temperature, the reaction solution is poured into 200g of crushed ice, the mixture is filtered, a filter cake is washed by water, and the mixture is separated and purified by a silica gel column to obtain a compound Int-22 which is a white solid and has the yield of 87%.
In a similar synthetic process as described above, the following intermediates were prepared:
the fourth step: preparation of Compound PP486
Referring to the preparation process of the fifth step in example 11, only Int-16 of the fifth step in example 11 was replaced with Int-22 and 9, 10-dihydro-9, 9-dimethylacridine of the fifth step in example 11 was replaced with carbazole to prepare compound PP486 as a white solid in a yield of 72%, HRMS: 600.2092[ M + H] + 。
Example 14
Referring to the synthesis method of example 13, the preparation of compounds PP 480-PP 485 and PP 487-PP 491 included only replacing Int-22 in the fourth step of example 13 with the corresponding intermediate prepared in the third step, replacing carbazole in the fourth step of example 13 with the corresponding amine, changing the mass and amount of the compounds according to the molar weight, and adjusting other experimental parameters according to actual needs, thereby preparing compounds PP 480-PP 485 and PP 487-PP 491.
Preparation of organic electroluminescent element
Test examples 1 to 20
The following compound C was used as a hole injection material, the compound TAPC was used as a hole transport material, the compound mCP was used as an electron blocking layer material, the compounds PP281 to PP493 of the present invention were used as a dopant material of a light emitting layer, the compound F was used as a host material of a light emitting layer, the compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
The compound
The light-emitting element was sequentially deposited on ITO glass by an EL deposition apparatus manufactured by DOV.
The results of examining the properties of the obtained organic electroluminescent element are shown in Table 1, in which the driving voltage (V), the current efficiency (LE), and the luminance were measured at a current density of 10mA/cm 2 Under the conditions, the lifetime LT 95% of the element was determined to be 1000cd/cm at the initial luminance 2 And (4) obtaining the product.
TABLE 1 test results of device Properties
As can be seen from table 1, the organic electroluminescent device prepared from the compound of the present invention exhibits low voltage and high efficiency.
In Table 1, only some of the properties of the compounds in PP281 to PP493 are listed, and the properties of other compounds are substantially consistent with the structures of the compounds listed in the table, and are not listed due to space limitation.
As shown in fig. 1, which is a schematic view of a bottom emission example of the organic electroluminescent device of the present invention, the compound prepared according to the present invention is contained in the light emitting layer 5.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily think of the changes or substitutions within the technical scope of the present invention, and shall cover the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (9)
1. An organic compound having the structure of formula (I):
wherein, W 1 ～W 4 Identically or differently representing N or CR 5 Or any two adjacent radicals W 1 、W 2 、W 3 、W 4 Represents a group of the following formula (III),
wherein Z, identically or differently at each occurrence, denotes CR 6 Or N, and ^ indicates the corresponding adjacent group W in formula I 1 And W 2 、W 2 And W 3 Or W 3 And W 4 ；T 1 Denotes SO 2 Or CO;
l represents a single bond, or one of a sub-aromatic ring system or a sub-heteroaromatic ring system having 5 to 60 carbon atoms;
R 1 ～R 6 each of which is the same or different and is selected from hydrogen, deuterium, an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms;
the-NAr 1 Ar 2 The structure of (a) is selected from the group shown below:
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, a halogen atom, an organic group, a, an organic group, a, an organic group, an organic compounds, an organic group, a, an organic group, an organic compounds, a 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 One of alkenyl or alkynyl groups, aromatic or heteroaromatic ring systems having 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms,
wherein the dashed bond indicates bonding to L;
T 2 representation O, S, NAr 3 Or CR 7 R 8 ；
Ar is 3 Selected from phenyl, naphthyl; said R is 7 、R 8 Selected from methyl, phenyl, fluorenyl.
2. The organic compound according to claim 1, wherein the formula (I) includes the structures represented by the following formulae (I) -1, formula (I) -11, formula (I) -12:
wherein R is 1 ～R 5 、L、-NAr 1 Ar 2 Is as defined in claim 1.
3. The organic compound according to claim 1, wherein L is selected from a single bond, groups represented by the following (1) to (3), and combinations thereof:
，
the R has the meaning given in claim 1, and one dotted bond indicates a bond to the compound body and the other dotted bond indicates a bond to N.
4. An organic compound, characterized in that the organic compound comprises the following compounds represented by PP281 to PP 493:
5. use of the organic compound according to any one of claims 1 to 4 in a material for an organic element.
6. The use according to claim 5, wherein the organic compound is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
7. Use according to claim 6, wherein the organic compound is used in a light emitting layer material, an electron transporting/hole blocking layer material or an encapsulation layer material.
8. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers between the first electrode and the second electrode, wherein at least one of the organic layers contains the organic compound according to any one of claims 1 to 4.
9. A light-emitting device comprising the organic electroluminescent element according to claim 8.
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