CN114605433B - Indenothiophene dioxide structure-containing organic material and application thereof - Google Patents
Indenothiophene dioxide structure-containing organic material and application thereof Download PDFInfo
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- CN114605433B CN114605433B CN202210335055.2A CN202210335055A CN114605433B CN 114605433 B CN114605433 B CN 114605433B CN 202210335055 A CN202210335055 A CN 202210335055A CN 114605433 B CN114605433 B CN 114605433B
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- organic material
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- electron withdrawing
- organic
- unsubstituted aromatic
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- 239000011368 organic material Substances 0.000 title claims abstract description 28
- LQIINACETPLXNV-UHFFFAOYSA-N 2H-indeno[2,1-b]thiophene 3,3-dioxide Chemical group O=S1(C2=CC(C=CC=C3)=C3C2=CC1)=O LQIINACETPLXNV-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- -1 n-octyl Chemical group 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 30
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000004431 deuterium atom Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 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 claims 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 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 abstract description 6
- 238000000034 method Methods 0.000 description 44
- 239000007787 solid Substances 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 238000000921 elemental analysis Methods 0.000 description 25
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 238000005259 measurement Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- PGGAYCHAGYRSPB-UHFFFAOYSA-N 1-bromo-2-(3-chlorophenoxy)benzene Chemical compound ClC1=CC=CC(OC=2C(=CC=CC=2)Br)=C1 PGGAYCHAGYRSPB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000001425 triazolyl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RRWFUWRLNIZICP-UHFFFAOYSA-N 1-bromo-2-phenoxybenzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1 RRWFUWRLNIZICP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- JYGHOGAUQCUXJQ-UHFFFAOYSA-N 1-bromo-2-(3-chlorophenyl)sulfanylbenzene Chemical compound ClC1=CC=CC(SC=2C(=CC=CC=2)Br)=C1 JYGHOGAUQCUXJQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 150000001975 deuterium Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BATOISXASQUNHX-UHFFFAOYSA-N 1-bromo-2-phenylsulfanylbenzene Chemical compound BrC1=CC=CC=C1SC1=CC=CC=C1 BATOISXASQUNHX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000001276 controlling effect Effects 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- OBUOMTRFSCUDKS-UHFFFAOYSA-N isoquinolin-6-ylboronic acid Chemical compound C1=NC=CC2=CC(B(O)O)=CC=C21 OBUOMTRFSCUDKS-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- GWSIHDYDBUZCJX-UHFFFAOYSA-N (2,3-diphenylquinoxalin-6-yl)boronic acid Chemical group OB(C1=CC=C2N=C(C3=CC=CC=C3)C(C3=CC=CC=C3)=NC2=C1)O GWSIHDYDBUZCJX-UHFFFAOYSA-N 0.000 description 1
- GTHCRSAGVUPPTG-UHFFFAOYSA-N (5-pyridin-3-ylpyridin-2-yl)boronic acid Chemical group B(C1=NC=C(C=C1)C2=CN=CC=C2)(O)O GTHCRSAGVUPPTG-UHFFFAOYSA-N 0.000 description 1
- WQKCDNPPGJJRHG-UHFFFAOYSA-N (6-pyridin-2-ylpyridin-3-yl)boronic acid Chemical group N1=CC(B(O)O)=CC=C1C1=CC=CC=N1 WQKCDNPPGJJRHG-UHFFFAOYSA-N 0.000 description 1
- XNHXNEXGBTXJIA-UHFFFAOYSA-N 1-bromo-4-chloro-2-phenoxybenzene Chemical compound ClC1=CC=C(Br)C(OC2=CC=CC=C2)=C1 XNHXNEXGBTXJIA-UHFFFAOYSA-N 0.000 description 1
- FQYUKLYDZMMIKD-UHFFFAOYSA-N 1-bromo-4-chloro-2-phenylsulfanylbenzene Chemical compound ClC(C=C1)=CC(SC2=CC=CC=C2)=C1Br FQYUKLYDZMMIKD-UHFFFAOYSA-N 0.000 description 1
- BXLDBXFOJFBOQI-UHFFFAOYSA-N B(O)(O)O.O1C=NC2=C1C=CC=C2 Chemical group B(O)(O)O.O1C=NC2=C1C=CC=C2 BXLDBXFOJFBOQI-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- KFTLUGFBPAVEIA-UHFFFAOYSA-N OB(O)C1=NC2=C(C=CC=C2)C2=C1C=CC=C2 Chemical compound OB(O)C1=NC2=C(C=CC=C2)C2=C1C=CC=C2 KFTLUGFBPAVEIA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
The invention relates to the technical field of organic electroluminescent display, in particular to an organic material containing indenothiophene dioxide structure, and also discloses application of the organic material in an organic electroluminescent device. The indenothiophene dioxide structure-containing organic material provided by the invention is shown in a general formula (I), can be applied to the field of organic electroluminescence, and can be used as an electron transport material. The structural compound provided by the invention is applied to an OLED device, can reduce the driving voltage, improve the luminous efficiency of the device and prolong the service life of the device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a novel organic material containing indenothiophene dioxide structure, and also relates to application of the novel organic material in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements on the performance of flat panel display devices are increasing. Currently the main display technologies are plasma display devices, field emission display devices and organic electroluminescent display devices (OLEDs). Compared with a liquid crystal display device, the OLEDs do not need a backlight source, have wider visual angles and low power consumption, and have response speed which is 1000 times that of the liquid crystal display device, so that the OLEDs have wider application prospect.
Since the first report of high efficiency Organic Light Emitting Diodes (OLEDs), many scholars have been devoted to research how to improve the performance of OLED devices. The organic electron transport material is an important material for OLED devices. The organic charge transport material is an organic semiconductor material which can realize controllable directional and orderly movement of carriers under the action of an electric field when carriers (electrons or holes) are injected, thereby carrying out charge transport. The organic charge transport material is mainly transported holes, called hole type transport material, mainly transported electrons, called electron type transport material, or simply electron transport material. Organic charge transport materials have been developed to date, wherein hole transport materials are more various and have better properties, while electron transport materials are less various and have poorer properties. For example, the electron transport material Alq3 commonly used at present has high working voltage and serious power consumption due to low electron mobility; some electron transport materials such as LG201 have low triplet energy levels, and when phosphorescent materials are used as the light-emitting layer, an exciton blocking layer needs to be added, otherwise efficiency is lowered; still other materials, such as Bphen, crystallize easily, resulting in reduced lifetime. These problems with electron transport materials are all bottlenecks that affect the development of organic electroluminescent display devices. Therefore, the development of new electron transport materials with better performance would have important practical application value.
Disclosure of Invention
The invention aims to develop an electron transport material of an organic electroluminescent device, which is applied to an OLED device, can reduce driving voltage, improve luminous efficiency of the device and prolong service life of the device.
Specifically, in a first aspect, the present invention provides an indenothiophene dioxide structure-containing organic material having a structure as shown in general formula (i):
wherein X is selected from O, S, se, NR X1 、CR X2 R X3 、PR X4 And SiR X5 R X6 ；
R 1 ～R 4 Each independently represents H, deuterium atom, halogen atom, straight-chain or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, R 1 ～R 4 At least one of which is a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties and is linked to a parent nucleus represented by the general formula (I) through a C atom on the group;
R X1 、R X2 、R X3 、R X4 、R X5 and R is X6 Each independently selected from H, deuterium atom, halogen atom, substituted or unsubstituted alkyl, alkoxy or heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, alkylsilyl, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, aryl, aryloxy, heteroaryl, heteroaryloxy, arylsilyl, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfanyl, sulfinyl, sulfonyl, phosphino;
m, n, p and q are each independently selected from integers from 1 to 4. Preferably, m, n, p and q are each independently selected from 1 or 2. More preferably, m, n, p and q are all 1.
The halogen atom is F, cl, br or I.
Straight chain alkyl means a compound of the formula C n H 2n+1 Linear alkyl groups including, but not limited to, methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like.
Branched alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like.
Cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
Alkylamino refers to a group on the amino group wherein at least one H is substituted with an alkyl group.
As a preferred embodiment of the present invention, the R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from any one of H, deuterium atom, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted spirobifluorenyl and substituted or unsubstituted naphthyl.
Preferably, said R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from any one of H, deuterium atoms and substituted or unsubstituted pyridyl.
More preferably, the R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from any one of H, deuterium atoms and pyridyl.
The R is 1 ～R 4 Represents a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties. The R is 1 ～R 4 When two or more of them represent substituted or unsubstituted aromatic groups having hetero atoms and having electron withdrawing properties, the groups represented are the same or different.
As a preferred embodiment of the present invention, in the general formula (I), the X is selected from O, S.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties contains at least one heteroatom, which is optionally selected from the group consisting of N atom, S atom and O atom.
The substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties may be a monocyclic aromatic hydrocarbon or a polycyclic aromatic hydrocarbon; the polycyclic aromatic hydrocarbon may be a polyphenylarene, a biphenyl type polycyclic aromatic hydrocarbon or a polycyclic aromatic hydrocarbon.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a hetero atom and having an electron withdrawing property is a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, the polycyclic aromatic hydrocarbon group is optionally selected from a polybenzoic aliphatic hydrocarbon group, a biphenyl type polycyclic aromatic hydrocarbon group and a condensed ring aromatic hydrocarbon group, the number of the hetero atoms contained is 1 to 6, and the hetero atoms are optionally selected from N, O, S.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a hetero atom and having an electron withdrawing property is a group containing at least one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, 1, 10-phenanthroline, pyridazinyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl;
the phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, 1, 10-phenanthroline, pyridazinyl, pyrimidinyl, pyrazinyl, benzopyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl may also have a substituent; the substituent is selected from alkyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphthoyl, benzimidazolyl, naphthyl, pyridyl, pyridoyl, pyrrolyl, imidazolyl, imidazo, pyrazolyl, pyrazolo, diazinyl, 1, 10-phenanthroline, s-triazinyl, fluorenyl, dibenzofuran, dibenzothiophene, quinolinyl, isoquinoline, carbazolyl;
the hydrogen on the substituent may be further substituted with 1 or more of any of the following groups, respectively: alkyl, phenyl, deuterated phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl.
As a further preferred embodiment, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of substituted or unsubstituted quinazolinyl, phenyl, biphenyl, benzopyrazinyl, oxadiazolyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, pyridinyl, 1, 10-phenanthroline, pyrazinyl, s-triazinyl, quinolinyl, isoquinolinyl, pyrimidinyl;
wherein the substituent groups employed in the substitution are optionally selected from one or more of the following groups: c (C) 1 ～C 5 Alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzoyl, naphthoyl, benzimidazolyl, naphthyl, pyridyl, 1, 10-phenanthroline-o-yl, pyrazino-yl, s-triazinyl, fluorenyl, dibenzofuranyl, quinolinyl;
the hydrogen on the substituents may be further substituted with at least one of any of the following groups, respectively: c (C) 1 ～C 5 Alkyl, phenyl, benzo, naphthyl, naphtho, pyridinyl, biphenyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl.
As a more preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from any of the substituents shown in the following structures:
wherein "- -" in each substituent group represents a substitution position.
Still further preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
as a preferred embodiment of the present invention, the organic material is selected from the group consisting of compounds represented by the following structural formula:
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in a second aspect, the present invention provides the use of an indenothiophene dioxide structure-containing organic material as described in the manufacture of an organic electroluminescent device.
Preferably, the indenothiophene dioxide structure-containing organic material is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising an electron transport layer comprising an indenothiophene dioxide structure-containing organic material according to the present invention.
Specifically, the invention provides an organic electroluminescent device which sequentially comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top, wherein an electron transport material of the electron transport layer comprises the compound shown in the general formula (I).
As a preferred embodiment, the thickness of the electron transport layer may be 10 to 50nm, preferably 20 to 40nm.
In a fourth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The invention provides a novel organic material compound containing indenothiophene dioxide structure, which is specifically shown in a general formula (I), wherein the indenothiophene dioxide structure is taken as a mother core, the mother core of the series of compounds has stronger electron withdrawing capability and good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; the electron-withdrawing group is connected with the organic light-emitting diode, so that the electron injection capability can be effectively enhanced, the electron transmission performance can be improved, the organic light-emitting diode can be well applied to OLED devices, the organic light-emitting diode can be used as an electron transmission material, and the photoelectric performance of the devices can be effectively improved.
The organic material containing indenothiophene dioxide structure provided by the invention can be used as an electron transmission material, has higher electron transmission performance, better film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, and can effectively improve the photoelectric performance of a device. Meanwhile, the Organic Light Emitting Diode (OLED) has the advantages of good thermal stability, stability and high efficiency, and can be well applied to OLED devices. Therefore, the driving voltage can be reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the device has important practical application value. The organic electroluminescent device made of the organic material has the characteristics of low driving voltage, high luminous efficiency and long service life. The device can be applied in the fields of display and illumination.
Detailed Description
The technical scheme of the invention is described in detail through specific examples. The following examples are given to illustrate the present invention but are not to be construed as limiting the scope of the invention, and all equivalent changes or modifications that may be made without departing from the spirit of the invention as disclosed herein are intended to be included within the scope of the appended claims.
According to the preparation method provided by the invention, the preparation method can be realized by adopting known common means by a person skilled in the art, such as further selecting a proper catalyst and a proper solvent, determining a proper reaction temperature, a proper time, a proper material ratio and the like, and the invention is not particularly limited. Unless otherwise indicated, starting materials for solvents, catalysts, bases, etc. used in the preparation process may be synthesized by published commercial routes or by methods known in the art. By adopting the preparation method provided by the invention, a series of compounds shown in the general formula (I) are prepared.
Synthetic intermediates
Synthesis of intermediate M1
The synthetic route is as follows:
the specific operation steps are as follows:
(1) In a 2L three-necked flask, 2-bromobenzo [ b ] was added]Thiophene (21.3 g,0.1 mol), methyl 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (26.2 g,0.1 mol), sodium carbonate (26.5 g,0.25 mol), toluene 200mL, ethanol 200mL, water 150mL, pd (PPh) was added after the reaction system was replaced with nitrogen for protection 3 ) 4 (11.5 g,10 mmol). The reaction was heated at reflux for 6 hours and stopped. The solvent was distilled off, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and purified by column chromatography to give 23.0g of white solid M1-1 in a yield of about 86%.
(2) Into a 1L three-necked flask, M1-1 (26.8 g,0.1 mol), sodium hydroxide (0.8 g,0.2 mol), 200mL of ethanol, and the reaction was refluxed for 2 hours to stop the reaction. The pH is regulated to 2-3 by 50% dilute hydrochloric acid, stirred for half an hour, and filtered by suction to obtain 24.9g of white solid M1-2 with the yield of about 98%.
(3) Into a 1L three-necked flask, M1-2 (25.4 g,0.1 mol), 25g of methanesulfonic acid and 200mL of toluene were added, stirring and heating were started, the reaction was carried out at 90-100℃for 2 hours, the temperature was lowered to room temperature, 200mL of distilled water was added, stirring was carried out for half an hour, and suction filtration was carried out to obtain 21.2g of a white solid M1-3, the yield of which was about 90%.
(4) M1-3 (23.6 g,0.1 mol) and 600mL of methylene chloride are added into a 2L three-necked flask, stirring is started, an aqueous hydrogen peroxide solution (40 mL,0.4mol, 30%) is slowly added dropwise, the reaction is carried out at room temperature for 2 hours, 100mL of saturated aqueous sodium bicarbonate solution is added after the reaction is finished, stirring and liquid separation are carried out, and the mixture is dried by spinning to obtain 24.1g of white solid M1-4 with the yield of about 90%.
(5) 1-bromo-2- (3-chlorophenoxy) benzene (28.4 g,0.1 mol) and 400mL of THF were added to a 2L three-necked flask under nitrogen protection, cooled to-78deg.C, and n-butyllithium (100 mL,0.25 mol) was slowly added dropwise with stirring for about 1 hour, and the dropping funnel was flushed with 50mL of THF and incubated for 1 hour. M1-4 (26.8 g,0.1 mol) was slowly added dropwise to the low temperature system at-78℃and then the dropping funnel was rinsed with a small amount of THF, and after completion of the addition, the temperature was kept for 1 hour, and then the temperature was slowly raised to room temperature, and the reaction was stirred at room temperature for 1 hour, and the reaction was completed. The pH was adjusted to neutral, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried, yielding 42.6g of white solid M1-5 in about 90% yield.
(6) M1-5 (47.3 g,0.1 mol), 50mL of concentrated hydrochloric acid and 200mL of glacial acetic acid are added into a 1L three-necked flask, stirring and heating are started, reaction is carried out at 100 ℃ for 4 hours, and the temperature is reduced to room temperature. The mixture was neutralized, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried by spin-drying to give 38.7g of white solid M1 in a yield of about 85%.
Product MS [ M+H ]] + :455; elemental analysis (C) 27 H 15 ClO 3 S): theoretical value: c,71.29%; h,3.32%; cl,7.79%; o,10.55%; s,7.05%; actual measurement value: c:71.18%, H:3.29%.
Synthesis of intermediate M2
The synthetic route is as follows:
the procedure for the preparation of this compound refers to the procedure for intermediate M1 in which in step (5) the reactant 1-bromo-2-phenoxybenzene was used instead of 1-bromo-2- (3-chlorophenoxy) benzene, the remaining conditions being unchanged, to give 35.7g of a white solid in about 85% yield. After the step (6), the step (7) is performed, specifically as follows:
(7) Into a 1L three-necked flask, M2-6 (45.5 g,0.1 mol) and 200mL of methylene chloride were added, stirring was started, the temperature was controlled at 0-5℃and bromine (1.6 g,0.1 mol) was added thereto, followed by reaction at 0-5℃for 3 hours. The mixture was neutralized, the organic phase was separated, subjected to column chromatography and dried to obtain 44.9g of M2 as a white solid in a yield of about 90%.
Product MS [ M+H ]] + :500; elemental analysis (C) 27 H 15 BrO 3 S): theoretical value: c,64.94%; h,3.03%; br,16.00%; o,9.61%; s,6.42%; actual measurement value: c:64.91%, H:3.10%.
Synthesis of intermediate M3
The synthesis method comprises the following steps:
preparation procedure referring to the procedure for intermediate M1, intermediate M3 was prepared by substituting methyl 4-chloro-2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate for methyl 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate and substituting 1-bromo-2- (3-chlorophenoxy) benzene for 1-bromo-2-phenoxybenzene, following the above synthetic route, to give 36.4g of white solid in about 80% yield.
Product MS [ M+H ]] + :455; elemental analysis (C) 27 H 15 ClO 3 S): theoretical value: c,71.29%; h,3.32%; cl,7.79%; o,10.55%; s,7.05%; actual measurement value: c:71.24%, H:3.28%.
Synthesis of intermediate M4
The preparation process refers to the method of the intermediate M1, and the synthesis method is as follows:
the synthesis of intermediate M4 was performed according to the above synthetic route substituting methyl 4-chloro-2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate for methyl 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate to yield 36.2g of white solid in about 74% yield.
Product MS [ M+H ]] + :490; elemental analysis (C) 27 H 14 Cl 2 O 3 S): theoretical value: c,66.27%; h,2.88%; cl,14.49%; o,9.81%; s,6.55%; actual measurement value: c:66.13%, H:2.76%.
Synthesis of intermediate M5
The preparation process of the intermediate refers to the method of the intermediate M1 in the step (6), and the operation in the step (7) is as follows: into a 1L three-necked flask, M5-6 (45.5 g,0.1 mol) and 200mL of methylene chloride were charged, stirring was started, the temperature was controlled at 0-5℃and bromine (1.6 g,0.1 mol) was added thereto, followed by reaction at 0-5℃for 3 hours. The mixture was neutralized, and the organic phase was separated and dried to obtain 41.6g of M5 as a white solid in a yield of about 78%.
Product MS [ M+H ]] + : 534. Elemental analysis (C) 27 H 14 BrClO 3 S): theoretical value: c,60.75%; h,2.64%; br, 14.97%; cl,6.64%; o,8.99%; s,6.01%; actual measurement value: c:60.62%, H:2.59%.
Synthesis of intermediate M6
Preparation referring to the procedure for intermediate M1, in step (5), the reactant (2-bromophenyl) (3-chlorophenyl) sulfane was substituted for 1-bromo-2- (3-chlorophenoxy) benzene, the remaining conditions unchanged, to give 35.4g of a white solid in about 75% yield.
Product MS [ M+H ]] + :471; elemental analysis (C) 27 H 15 ClO 2 S 2 ): theoretical value: c,68.86%; h,3.21%; cl,7.53%; o,6.79%; s,13.61%; actual measurement value: c:68.83%, H:3.20%.
Synthesis of intermediate M7
Preparation procedure referring to the procedure for intermediate M2, (2-bromophenyl) (phenyl) sulfane was used instead of 1-bromo-2-phenoxybenzene, the remaining conditions unchanged, to give 39.7g of a white solid in about 77% yield.
Product MS [ M+H ]] + :516; elemental analysis (C) 27 H 15 BrO 2 S 2 ): theoretical value: c,62.92%; h,2.93%; br,15.50%; o,6.21%; s,12.44%; actual measurement value: c:62.91%, H:2.94%.
Synthesis of intermediate M8
Preparation procedure referring to the procedure for intermediate M3, (2-bromophenyl) (phenyl) sulfane was used instead of 1-bromo-2-phenoxybenzene, the remaining conditions unchanged, to give 38.07g of a white solid in about 81% yield.
Product MS [ M+H ]] + :471; elemental analysis (C) 27 H 15 ClO 2 S 2 ): theoretical value: c,68.86%; h,3.21%; cl,7.53%; o,6.79%; s,13.61%; actual measurement value: c:68.84%, H:3.25%.
Synthesis of intermediate M9
Preparation referring to the procedure for intermediate M4, (2-bromo-5-chlorophenyl) (phenyl) sulfane was substituted for 1-bromo-4-chloro-2-phenoxybenzene, the remaining conditions unchanged, to give 38.4g of a white solid in about 76% yield.
Product MS [ M+H ]] + :506; elemental analysis (C) 27 H 14 Cl 2 O 2 S 2 ): theoretical value: c,64.16%; h,2.79%; cl, 14.03%; o,6.33%; s,12.69%; actual measurement value: c:64.18%, H:2.75%.
Synthesis of intermediate M10
Preparation procedure referring to the procedure for intermediate M5, (2-bromophenyl) (3-chlorophenyl) sulfane was substituted for 1-bromo-2- (3-chlorophenoxy) benzene, the remaining conditions unchanged, to give 37.92g of a white solid in about 69% yield.
Product MS [ M+H ]] + :550; elemental analysis (C) 27 H 14 BrClO 2 S 2 ): theoretical value: c,58.98%; h,2.57%; br, 14.53%; cl,6.45%; o,5.82%; s,11.66%; actual measurement value: 58.96% of C and 2.55% of H.
Synthesis of intermediate M11
The synthetic route is as follows:
preparation procedure referring to the procedure for intermediate M1, the synthesis was performed according to the scheme shown above, substituting the reactant (2-bromophenyl) (3-chlorophenyl) sulfane for 1-bromo-2- (3-chlorophenoxy) benzene, with the remaining conditions unchanged. In step (7), M11-6 (47.1 g,0.1 mol), NCS (14.6 g,0.11 mol), carbon tetrachloride 100g, alCl are added 3 0.48g, at 70-80 deg.C for 2h, filtering, column chromatography, spin drying the solvent, drying to obtain 37.96g white solid with a yield of about 65%.
Product MS [ M+H ]] + :506; elemental analysis (C) 27 H 14 Cl 2 O 2 S 2 ): theoretical value: c,64.16%; h,2.79%; cl, 14.03%; o,6.33%; s,12.69%; actual measurement value: 64.13% of C and 2.77% of H.
Other types of intermediates similar to the structure of the invention can be correspondingly substituted and synthesized by referring to the method, and target intermediates can be obtained, and the description of the method is omitted in the invention.
The synthesis of specific target compounds was performed using the above intermediates synthesized according to the present invention.
EXAMPLE 1 Synthesis of Compound I-13
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was stirred magnetically, and M1 (45.5 g,0.1 mol), naphthothiazole boric acid (32.9 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and dioxane (400 ml) were sequentially added after nitrogen substitution, followed by stirring. After a further nitrogen displacement (0.8 g,4 mmol) tri-tert-butylphosphine and (1.4 g,1.5 mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and reducing the temperature after the reaction is finished. The mixture was neutralized, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried by spin-drying to give 47.1g of a white solid in a yield of about 78%.
Product MS [ M+H ]] + :604; elemental analysis (C) 38 H 21 NO 3 S 2 ): theoretical value: c,75.60%; h,3.51%; n,2.32%; o,7.95%; s,10.62%; actual measurement value: c:75.62%, H:3.49%, N:2.33%.
EXAMPLE 2 Synthesis of Compound I-16
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1, substituting benzoxazole boric acid for naphthothiazole boric acid, the remaining conditions remain unchanged, yielding 38.6g of a white solid in about 72% yield.
Product MS [ M+H ]] + :538; elemental analysis (C) 34 H 19 NO 4 S): theoretical value: c,75.96%; h,3.56%; n,2.61%; o,11.90%; s,5.96%; actual measurement value: c:75.87%, H:3.53%, N:2.64%.
EXAMPLE 3 Synthesis of Compound I-19
The synthetic route is as follows:
the preparation process comprises the following steps: into a 1L three-necked flask, M2 (49.9 g,0.1 mol), 1-pyridine-4-phenylboronic acid (19.9 g,0.1 mol), sodium carbonate (10.6 g,0.1 mol), toluene 150mL, ethanol 150mL, water 150mL were placed, and the reaction system was purged with nitrogen and then Pd (PPh) 3 ) 4 (11.5 g,0.01 mol). The reaction was heated to reflux (the temperature in the system was about 78 ℃ C.) for 3 hours, and the reaction was stopped. The solvent was removed by evaporation, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column chromatographed on petroleum ether/ethyl acetate (2:1), the solvent was dried by spinning, slurried with ethyl acetate, and filtered to give 46.5g of a white solid in about 81% yield.
Product MS [ M+H ]] + :574; elemental analysis (C) 38 H 23 NO 3 S): theoretical value: c,79.56%; h,4.04%; n,2.44%; o,8.37%; s,5.59%; actual measurement value: c:79.51%, H:4.06%, N:2.41%.
EXAMPLE 4 Synthesis of Compound I-30
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1, substituting M3 for M1, benzo [1,10] phenanthroline-6-boronic acid for naphthothiazole boronic acid, the remaining conditions remain unchanged, yielding 42.1g of a white solid in about 65% yield.
Product MS [ M+H ]] + ：649; elemental analysis (C) 43 H 24 N 2 O 3 S): theoretical value: c,79.61%; h,3.73%; n,4.32%; o,7.40%; s,4.94%; actual measurement value: c:79.59%, H:3.74%, N:4.31%.
EXAMPLE 5 Synthesis of Compound I-50
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1,4- (phenyl-d 5) quinazoline-5, 6,7,8-d 4-2-boronic acid instead of naphthothiazole boronic acid, the remaining conditions were unchanged, yielding 47.5g of a white solid in about 75% yield.
Product MS [ M+H ]] + :634; elemental analysis (C) 41 H 15 D 9 N 2 O 3 S): theoretical value: c,77.70%; h,5.25%; n,4.42%; o,7.57%; s,5.06%; actual measurement value: c:77.68%, H:5.23%, N:4.39%.
EXAMPLE 6 Synthesis of Compound I-51
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1, substituting M3 for M1,4- (phenyl-d 5) quinoline-2-boronic acid for naphthothiazole boronic acid, the remaining conditions unchanged, gave 50.3g of a white solid in about 80% yield.
Product MS [ M+H ]] + :629; elemental analysis (C) 42 H 20 D 5 NO 3 S): theoretical value: c,80.23%; h,4.81%; n,2.23%; o,7.63%; s,5.10%; actual measurement value: c:80.21%, H:4.79%, N:2.21%.
EXAMPLE 7 Synthesis of Compound I-53
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1, the equivalent of isoquinoline-6-boronic acid, cesium carbonate, tri-t-butylphosphine, tris (dibenzylideneacetone) dipalladium was changed to 2 with M4 instead of M1 and isoquinoline-6-boronic acid instead of naphthothiazole boronic acid, and the remaining conditions were unchanged, to obtain 47.2g of a white solid in about 70% yield.
Product MS [ M+H ]] + :675; elemental analysis (C) 45 H 26 N 2 O 3 S): theoretical value: c,80.10%; h,3.88%; n,4.15%; o,7.11%; s,4.75%; actual measurement value: c:80.11%, H:3.86%, N:4.12%.
EXAMPLE 8 Synthesis of Compound I-54
The synthetic route is as follows:
the preparation process comprises the following steps: into a 1L three-necked flask, M5 (53.4 g,0.1 mol), isoquinoline-6-boric acid (25.5 g,0.1 mol), sodium carbonate (21.2 g,0.2 mol), toluene 150mL, ethanol 150mL, water 150mL were placed, and after the reaction system was replaced with nitrogen, pd (PPh) was added 3 ) 4 (11.5 g,0.01 mol). The reaction was heated to reflux (the temperature in the system was about 78 ℃ C.) for 3 hours, and the reaction was stopped. Evaporating off the solvent, extracting with dichloromethane, drying with anhydrous magnesium sulfate, filtering,petroleum ether/ethyl acetate (2:1) column chromatography, spin-drying solvent, beating with ethyl acetate, filtering to obtain 39.5g white solid I-54-1, yield about 68%.
1L three-necked flask, magnetic stirring, nitrogen substitution, and then adding the product I-54-1 (58.2 g,0.1 mol), phenanthridin-6-ylboronic acid (30.5 g,0.1 mol), cesium carbonate (39 g,0.12 mol) and dioxane 400ml obtained in the previous step in sequence, and stirring was started. After a further nitrogen displacement (0.8 g,4 mmol) tri-tert-butylphosphine and (1.4 g,1.5 mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and reducing the temperature after the reaction is finished. The mixture was neutralized, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried by spin-drying to give 52.8g of white solid I-54 in a yield of about 73%.
Product MS [ M+H ]] + :725; elemental analysis (C) 49 H 28 N 2 O 3 S): theoretical value: c,81.20%; h,3.89%; n,3.86%; o,6.62%; s,4.42%; actual measurement value: c:80.18%, H:3.84%, N:3.82%.
EXAMPLE 9 Synthesis of Compound I-64
The synthetic route is as follows:
preparation procedure referring to the procedure of example 1, substituting M6 for M1 and substituting 2, 3-diphenylquinoxaline-6-boronic acid for naphthothiazole boronic acid, the remaining conditions remain unchanged, yielding 59.6g of a white solid in about 83% yield.
Product MS [ M+H ]] + :717; elemental analysis (C) 47 H 28 N 2 O 2 S 2 ): theoretical value: c,78.75%; h,3.94%; n,3.91%; o,4.46%; s,8.94%; actual measurement value: c:78.79%, H:3.93%, N:3.90%.
EXAMPLE 10 Synthesis of Compound I-68
The synthesis method comprises the following steps:
preparation procedure referring to the procedure of example 1, substituting M6 for M1 and substituting 2- ([ 1,1' -biphenyl ] -4-yl) -1,3, 4-oxadiazole-5-boronic acid for naphthothiazole boronic acid, the remaining conditions were unchanged, 49g of white solid was obtained in about 75% yield.
Product MS [ M+H ]] + :657; elemental analysis (C) 41 H 24 N 2 O 3 S 2 ): theoretical value: c,74.98%; h,3.68%; n,4.27%; o,7.31%; s,9.76%; actual measurement value: c:74.96%, H:3.67%, N:4.21%.
EXAMPLE 11 Synthesis of Compound I-70
The synthesis method comprises the following steps:
preparation procedure referring to the procedure of example 1, substituting M8 for M1 and 1-phenyl-2- (4-boronic acid-phenyl) -4-benzo [ d ] imidazole for naphthothiazole boronic acid, the remaining conditions were unchanged to give 50.6g of a white solid in about 72% yield.
Product MS [ M+H ]] + :705; elemental analysis (C) 46 H 28 N 2 O 2 S 2 ): theoretical value: c,78.38%; h,4.00%; n,3.97%; o,4.54%; s,9.10%; actual measurement value: c:78.34%, H:4.06%, N:3.96%.
EXAMPLE 12 Synthesis of Compound I-75
The synthesis method comprises the following steps:
preparation procedure referring to the procedure of example 1, substituting M7 for M1 and substituting 4-pyridine-phenylboronic acid for naphthothiazole boronic acid, the remaining conditions remain unchanged to give 45.9g of white solid in about 78% yield.
Product MS [ M+H ]] + : 590. Elemental analysis (C) 38 H 23 NO 2 S 2 ): theoretical value: c,77.39%; h,3.93%; n,2.38%; o,5.43%; s,10.87%; actual measurement value: c:77.34%, H:3.95%, N:2.34%.
EXAMPLE 13 Synthesis of Compound I-80
The synthesis method comprises the following steps:
preparation procedure referring to the procedure of example 1, substituting M11 for M1 and substituting 2,2' -bipyridine-5-boronic acid for naphthothiazole boronic acid, the remaining conditions remain unchanged to give 47.6g of white solid in about 64% yield.
Product MS [ M+H ]] + :745; elemental analysis (C) 47 H 28 N 4 O 2 S 2 ): theoretical value: c,75.79%; h,3.79%; n,7.52%; o,4.30%; s,8.61%; actual measurement value: c:75.77%, H:3.75%, N:7.54%.
EXAMPLE 14 Synthesis of Compound I-81
The synthetic route is as follows:
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preparation procedure referring to the procedure of example 1, substituting M9 for M1 and substituting [3,3' -bipyridyl ] -6-yl boronic acid for naphthothiazole boronic acid, the remaining conditions remain unchanged to give 49.2g of a white solid in about 66% yield.
Product MS [ M+H ]] + :745; elemental analysis (C) 47 H 28 N 4 O 2 S 2 ): theoretical value: c,75.79%; h,3.79%; n,7.52%; o,4.30%; s,8.61%; actual measurement value: c:75.71%, H:3.72%, N:7.49%.
According to the synthetic schemes of examples 1 to 14, other compounds of I-1 to I-112 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 15
The embodiment provides a group of OLED green light devices, which have the following structure: ITO/HATCN (1 nm)/HT 01 (40 nm)/NPB (25 nm)/EML (30 nm)/electron transport layer (35 nm)/LiF (1 nm)/Al containing any of the compounds provided in examples 1-14, prepared by:
(1) Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in a mixed solvent of acetone and ethanol (volume ratio is 1:1), baking in a clean environment until the moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
(2) Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, vacuum evaporating HATCN as a first hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 1nm; evaporating a second hole injection layer HT01, wherein the evaporation rate is 0.1nm/s, and the thickness is 40nm; then, an NPB layer is evaporated on the hole injection layer film to be a hole transport layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 25nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
(3) Vacuum evaporation of EML (electro-luminescence) on hole transport layer as light emitting layer of device, wherein the EML comprises main material and dye material, and the evaporation rate of main material PRH01 is regulated to 0.1nm/s by using multi-source co-evaporation method, and the dye material Ir (piq) 2 The concentration of acac is 5%, and the total film thickness of evaporation is 30nm; wherein PRH01, ir (piq) 2 The structural formula of acac is as follows:
(4) Evaporating the compound provided in the embodiment 1 as an electron transport material of an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm;
(5) Sequentially vacuum evaporating LiF with the thickness of 1nm on the electron transport layer to serve as an electron injection layer of the device, and continuously evaporating an Al layer on the electron injection layer to serve as a cathode of the device, wherein the film thickness of the evaporated film is 150nm; the OLED-1 device of the present invention was obtained.
Referring to the preparation method of the OLED device, only the electron transport materials in the step (4) are replaced by other compounds synthesized in the examples 2-14, so that OLED-2-OLED-14 devices are obtained.
The electron transport materials in the step (4) are respectively replaced by compounds I-82, I-87, I-95, I-96, I-105, I-106 and I-110 in the list synthesized by the invention, so that OLED-15-OLED-21 devices are respectively prepared.
According to the same procedure as above, only the electron transport material in step (4) was replaced with a comparative compound, the structural formula was as follows, and comparative example devices OLED-22, OLED-23 were obtained.
The performance of the devices OLED-1 to OLED-23 obtained by the method is detected, and the detection results are shown in Table 1.
TABLE 1
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The results in Table 1 show that the novel organic material is used for organic electroluminescent devices, is used as an electron transport material of an electron transport layer, and the prepared device has obviously lower voltage than a comparative example under the condition of same brightness, has obviously better efficiency and service life than the comparative example, and is a novel electron transport material with good performance.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (13)
1. An indenothiophene dioxide structure-containing organic material, characterized by having a structure as shown in general formula (i):
wherein, the X is selected from O, S;
R 1 ～R 4 each independently represents H, deuterium atom, halogen atom, straight-chain or branched alkyl, cycloalkyl, amino, alkylamino, aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, and R 1 ～R 4 At least one of which is a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties, andthe C atom on the per group is connected with a parent nucleus shown in the general formula (I);
the straight-chain or branched-chain alkyl is selected from methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl and neopentyl;
the cycloalkyl is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl;
the alkylamino represents at least one H on the amino group substituted by methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl;
the aromatic group containing benzene ring and/or aromatic heterocycle is selected from phenyl, pyridyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, spirobifluorenyl and naphthyl;
the substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties is selected from the group shown in the following structure:
wherein "-" in each of the above groups represents a substitution position;
m, n, p and q are each independently selected from integers from 1 to 4.
2. The organic material of claim 1, wherein m, n, p and q are each independently selected from 1 or 2.
3. The organic material of claim 1, wherein m, n, p, and q are each 1.
4. The organic material of claim 1, wherein R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from any one of H, deuterium atom, phenyl, pyridyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, spirobifluorenyl and naphthyl.
5. The organic material of claim 1 or 4, wherein R 1 ～R 4 Except for the substituted or unsubstituted aromatic group containing hetero atoms and having electron withdrawing property, the rest groups are selected from any one of H, deuterium atoms and pyridyl.
6. The organic material of claim 1 or 4, wherein R 1 ～R 4 When two or more of the substituted or unsubstituted aromatic groups having heteroatom-containing and electron withdrawing properties are represented, the substituted or unsubstituted aromatic groups having heteroatom-containing and electron withdrawing properties may be the same or different.
7. The organic material of claim 1 or 4, wherein R 1 ～R 4 And one or any two of them represent a substituted or unsubstituted aromatic group containing a heteroatom and having electron withdrawing properties.
8. The organic material of claim 1, wherein the organic material is selected from the group consisting of compounds of the following structural formula:
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9. use of the indenothiophene dioxide structure-containing organic material according to any of claims 1 to 8 for the preparation of an organic electroluminescent device.
10. The use according to claim 9, characterized in that the indenothiophene dioxide structure-containing organic material is used as an electron transport material in an organic electroluminescent device.
11. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an electron transport layer, the electron transport layer comprises the organic material containing indenothiophene dioxide structure according to any one of claims 1 to 8.
12. A display device comprising the organic electroluminescent device as claimed in claim 11.
13. A lighting device comprising the organic electroluminescent device as claimed in claim 11.
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