CN115340534A - Compound, organic electroluminescent device and display device - Google Patents
Compound, organic electroluminescent device and display device Download PDFInfo
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- CN115340534A CN115340534A CN202110517150.XA CN202110517150A CN115340534A CN 115340534 A CN115340534 A CN 115340534A CN 202110517150 A CN202110517150 A CN 202110517150A CN 115340534 A CN115340534 A CN 115340534A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 105
- 239000000463 material Substances 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- -1 spirofluorene Chemical compound 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960005544 indolocarbazole Drugs 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- UFZNZKGKBWOSJG-UHFFFAOYSA-N purin-2-one Chemical compound O=C1N=CC2=NC=NC2=N1 UFZNZKGKBWOSJG-UHFFFAOYSA-N 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000003786 synthesis reaction Methods 0.000 description 49
- 238000001514 detection method Methods 0.000 description 34
- 238000001819 mass spectrum Methods 0.000 description 24
- 239000010410 layer Substances 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BUADUHVXMFJVLH-UHFFFAOYSA-N 7-chloro-3-imidazol-1-yl-2H-1,2,4-benzotriazin-1-ium 1-oxide Chemical compound N1[N+](=O)C2=CC(Cl)=CC=C2N=C1N1C=CN=C1 BUADUHVXMFJVLH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
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- 239000003208 petroleum Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WCEBGEPQNMFINU-UHFFFAOYSA-N 5-bromo-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2C(OC3=CC=CC4=CC=CC2=C34)=C1 WCEBGEPQNMFINU-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 1
- KYFXEQHPAQBDRQ-UHFFFAOYSA-N OB(C(C=CC=C1)=C1C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=N1)O Chemical group OB(C(C=CC=C1)=C1C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=NC(C(C=C2)=CC=C2C2=CC=CC=C2)=N1)O KYFXEQHPAQBDRQ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- QHZHWFKZIRMHRT-UHFFFAOYSA-N [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 QHZHWFKZIRMHRT-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device and a display device. The structural formula of the compound is shown as the formula (I):
Description
Technical Field
The application relates to the field of electroluminescence, in particular to a compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
The selection of the hole layer, the light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency, the driving voltage and the lifetime of the device, and functional layer materials with higher performance are still being explored.
Therefore, in order to meet the higher requirements of people for OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the art.
Disclosure of Invention
The application discloses a compound, an organic electroluminescent device and a display device.
In order to achieve the purpose, the application provides the following technical scheme:
the application provides a compound, which is shown as a formula (I),
wherein X is selected from O or S;
A. b is respectively and independently selected from substituted or unsubstituted aromatic groups containing 6 to 40 carbon atoms, and A and B are different;
m and n are selected from 0 or 1;
Ar 1 、Ar 2 selected from unsaturated aromatic group of 3-40 carbon atoms, C-1-C-7, and, ar 1 、Ar 2 One of which is selected from unsaturated aromatic groups with 3 to 40 carbon atoms, and the other is selected from one of C-1 to C-7:
wherein X 1 ～X 12 Each independently selected from NR 1 、O、S、CR 2 R 3 And X 1 And X 2 At least one selected from NR 1 ，X 3 And X 4 At least one selected from NR 1 ，X 5 And X 6 At least one selected from NR 1 ，X 7 And X 8 At least one selected from NR 1 ，X 9 And X 10 At least one selected from NR 1 ，X 11 And X 12 At least one selected from NR 1 ；
R 1 Selected from alkyl groups having 1 to 20 carbon atoms or aromatic groups having 6 to 40 carbon atoms; r 2 、R 3 Each independently selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, and R 2 And R 3 The carbon atoms on the above may be linked to form a ring;
the hydrogen in the compound shown in the formula (I) can be replaced by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and aryl containing 6-40 carbon atoms.
Further, the C-1 to C-7 can form a fused aromatic structure with the structure described by formula C-X:
wherein, the number of the carbon atoms in the formula C-X is one or more, and the carbon atoms in the formula C-X are connected with the formulas C-1-C-7 through chemical bonds. This description is as follows:
when C-X and C-1 are linked by a chemical bond, the following structures are included, but not limited to:
other aspects may be appreciated with reference to the above description.
Further, A and B are independently selected from one or more of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, ar 1 At least one selected from carbazole, benzocarbazole, indolocarbazole, and indenocarbazole.
Further, ar 2 At least one selected from pyridine, pyrimidine, triazine, quinoline, isoquinoline, imidazole, benzimidazole, thiazole, benzothiazole, oxazole, benzoxazole, pyrazole or purine.
Further, the compound is selected from one of the following formulas I-1 to I-60 and II-1 to II-60:
in the specific structure listed above, AThe position linked to the benzoxanthene mother ring, B and the position linked to the benzoxanthene mother ring are linked at specific positions. Composition Ar 1 、Ar 2 Any possible connection between the individual aromatic groups of a, B is included in the claims of the present application. As long as the structure constituting formula (1) maintains a conjugated aromatic system.
In addition, the compounds of the present application also include isomers of the compounds of formulas I-1 to I-60 and formulas II-1 to II-60.
The following isomers are exemplified as follows:
compound I-16 is structurally as above, but includes, without limitation, the following structures, all defined as isomers of I-16:
isomers of the compounds with other specific structures can be understood with reference to the above explanations.
The application also provides an organic electroluminescent device comprising the compound of the application.
Further, the material of the electron transport layer of the organic electroluminescent device is the compound of the application.
Further, the host material of the light-emitting layer of the organic electroluminescent device is the compound.
Further, the organic electroluminescent device is a red device.
Further, the organic electroluminescent device is a red phosphorescent device.
A display device includes the organic electroluminescent device provided by the application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the compound shown in formula (I) is prepared by taking benzoxanthene or benzothianthene as a mother nucleus, limiting the substitution of each substituent group at the position of the benzoxanthene or benzothianthene, and simultaneously limiting a specific substituent group, and can be used as ETL and Host materials for improving the material performance, so that an organic electroluminescent device prepared by using the compound has higher luminous efficiency, lower driving voltage and longer service life.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
It should be noted that: in the present application, all embodiments and preferred methods mentioned herein can be combined with each other to form new solutions, if not specifically stated. In the present application, all the technical features mentioned herein and preferred features may be combined with each other to form new solutions, if not specifically stated. In the present application, percentages (%) or parts refer to percent by weight or parts by weight relative to the composition, unless otherwise specified. In the present application, the components referred to or the preferred components thereof may be combined with each other to form new embodiments, if not specifically stated. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "6 to 22" indicates that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is only a shorthand representation of the combination of these numbers. The "ranges" disclosed herein may be in the form of lower limits and upper limits, and may be one or more lower limits and one or more upper limits, respectively. In the present application, unless otherwise indicated, the individual reactions or process steps may or may not be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present application.
When X is selected from oxygen, the synthesis is illustrated as follows:
the specific synthetic processes of the intermediates M-703, M-803, M-903, M-704 and M-705 are as follows:
1) Synthesis of intermediate M-703
Adding 50 ml of DMF (dimethyl formamide), 2.97 g (0.01 mol) of 8-bromobenzo [ kl ] xanthene into a 250 ml three-neck flask, controlling the temperature to be 20-25 ℃, adding 2.25 g (0.01 mol) of N-iodosuccinimide (NIS) in batches under stirring, controlling the temperature to be 20-25 ℃ for reaction for 2 hours, heating to be 40-45 ℃ for reaction for 1 hour, heating to be 60 ℃ for reaction for 1 hour, cooling, adding water and dichloromethane for separating, washing an organic layer with water, carrying out silica gel column chromatography separation, and eluting with petroleum ether to obtain 0.8 g of a compound shown by M-703, 1.2 g of a compound shown by M-803 and 0.9 g of a compound shown by M-903.
Mass spectrometric detection was performed on the compound of formula M-703, the two largest peaks were 422, 424, and the molecular formula of the product was determined to be: c 16 H 8 BrIO。
The compound shown as the formula M-703 was subjected to nuclear magnetic detection, and the data were analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), delta 8.51 (m, 1H), delta 7.88 (m, 1H), delta 7.82 (m, 2H), delta 7.68 (m, 1H), delta 7.62 (d, 1H), delta 7.44 (d, 1H), delta 7.10 (m, 1H).
Mass spectrometric detection of the compound of formula M-803 shows that the two largest peaks are 422, 424, and the molecular formula of the product is determined as: c 16 H 8 BrIO。
The compound represented by the formula M-803 was subjected to nuclear magnetic detection, and the data were analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), delta 7.91 (m, 1H), delta 7.87 (m, 1H), delta 7.70-7.67 (m, 2H), delta 7.20 (m, 1H), delta 7.13 (m, 1H), delta 6.92 (d, 1H), delta 6.33 (m, 1H).
Mass spectrometric detection of the compound of formula M-903 showed that the two largest peaks were 422, 424, confirming the product molecular formula: c 16 H 8 BrIO。
The compound shown as the formula M-903 was subjected to nuclear magnetic detection, and the data were analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), delta 8.39 (m, 1H), delta 7.98 (m, 1H), delta 7.88 (m, 1H), delta 7.76 (m, 1H), delta 7.68 (m, 1H), delta 7.43 (d, 1H), delta 7.11 (m, 1H), delta 5.99 (d, 1H).
2) Synthesis of intermediate M-704
A 250 ml three-neck flask is put into a nitrogen protection bottle, 80 ml of toluene, 60 ml of ethanol and 20 ml of water are added, 4.23 g (0.01 mol) of a compound shown in M-703, 2.87 g (0.01 mol) of 9-phenylcarbazole-3-boric acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetratriphenylphosphine palladium are added, the temperature is slowly increased to 60 ℃ for reaction for 8 hours, the temperature is reduced, water is added for liquid separation, an organic layer is washed by water, magnesium sulfate and a small amount of 200-300-mesh silica gel are added for drying, the magnesium sulfate and the silica gel are removed by filtration, the solvent is removed by decompression, and the obtained solid is recrystallized by using a mixed solvent of toluene and ethanol to obtain 3.6 g of the compound shown in M-704.
Performing mass spectrum detection on the compound shown in M-704, wherein the largest two peaks are 537 and 539, and the molecular formula of the product is determined as follows: c 34 H 20 BrNO。
(3) Synthesis of intermediate M-705
The reaction process refers to the synthesis of M-704, except that 9-phenylcarbazole-3-boric acid is changed to 4- (4, 6-diphenyl-1, 3, 5-triazine-2-yl) phenylboronic acid, after the reaction is finished, the temperature is reduced, water is added, the obtained solid is filtered, and after the reduced pressure drying, the solid is separated by silica gel column chromatography, and petroleum ether: dichloromethane: ethyl acetate =9:1:0.5 (volume ratio) elution was performed, compound M-705.
The mass spectrum detection is carried out on the compound M-705, the maximum two peaks are 603 and 605, and the molecular formula of the product is determined as follows: c 37 H 22 BrN 3 O。
Synthesis example 1 Synthesis of Compound I-1-1
A 500 ml three-neck flask, under the protection of nitrogen, 150 ml dioxane and 30 ml water are added, 5.38 g (0.01 mol) of a compound shown in M-704, 3.53 g (0.01 mol) of 4- (4, 6-phenyl 1,3, 5-triazine-2-yl) phenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of palladium tetratriphenylphosphine are added, the mixture is slowly heated to reflux reaction for 12 hours, the temperature is reduced, water is added, the obtained solid is filtered, and after drying under reduced pressure, the mixture is separated by silica gel column chromatography, petroleum ether: dichloromethane: ethyl acetate =9:1:0.5 (volume ratio) to give 5.8 g of Compound I-1-1.
The mass spectrum detection is carried out on the compound I-1-1, and the mass spectrum detection is carried out on the mass spectrum detection result, wherein the mass spectrum detection ratio of m/z:766.
synthesis example 2 Synthesis of Compound II-1-1
Synthesis method with reference to the synthesis of Compound I-1, except that M-704 was replaced by M-705 and 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was replaced by 9-phenylcarbazole-3-boronic acid to give the compound represented by II-1-1.
Mass spectrometric detection of compound II-1-1, m/z:766.
synthesis example 3 Synthesis of Compound I-4-1
(1) And (3) synthesis of an intermediate M-I-4:
the synthesis method refers to the synthesis of M-704, except that 9-phenylcarbazole-3-boric acid is replaced by
Obtaining M-I-4.
The mass spectrum detection is carried out on the compound shown as M-I-4, the maximum two peaks are 653 and 655, and the molecular formula of the product is determined as follows: C43H28BrNO.
(2) Synthesis of Compound I-4-1:
reference was made to the synthesis of compound I-1-1 except that M-704 was changed to M-I-4 to give the compound represented by I-4-1.
The mass spectrum detection is carried out on the compound shown as I-4-1, and the mass spectrum detection is carried out on the m/z:882.
synthesis example 4 Synthesis of Compound I-46-1
Reference was made to the synthesis of compound I-1-1 except that the 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was replaced by
To obtain the compound shown as I-46-1.
The mass spectrum detection is carried out on the compound shown as I-46-1, and the mass spectrum detection is carried out on the m/z:727.
synthesis example 5 Synthesis of Compound I-52-1
Reference was made to the synthesis of compound I-1-1, except that the 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was replaced by
To obtain the compound shown as I-52-1.
The mass spectrum detection is carried out on the compound shown as I-52-1, and the mass spectrum detection is carried out on the m/z:652.
synthesis example 6 Synthesis of Compound II-4-1
Synthesis of reference Compound II-1-1, except that 9-phenylcarbazole-3-boronic acid was replaced
To obtain the compound shown as II-4-1.
Mass spectrum detection is carried out on the compound shown as II-4, and the mass spectrum detection ratio of m/z:882.
synthesis example 7 Synthesis of Compound II-46-1
(1) Synthesis of intermediate M-II-46
The reaction process refers to the synthesis of M-704, except that 9-phenylcarbazole-3-boric acid is replaced by
The compound shown in M-II-46 is subjected to mass spectrum detection, the maximum two peaks are 564 and 566, and the molecular formula of the product is determined as follows: c 35 H 21 BrN 2 O。
(2) Synthesis of Compound II-46-1
Synthesis of reference Compound II-1-1 except that M-705 was changed to M-II-46 to give the compound represented by II-46-1.
The mass spectrum detection is carried out on the compound shown as II-46-1, and the mass spectrum detection is carried out on the m/z:727.
the synthesis of products not shown in the above synthesis examples can be achieved by conventional methods using methods known in the art.
Device embodiment:
the specific structures of several materials used in this application are as follows:
synthesis of D-1:
referring to the synthesis of compound I-1-1 of example 1 except that M-704 was changed to 8-bromobenzo [ kl ] xanthene, the compound shown as D-1 was obtained.
Mass spectrometric detection of compound D-1, m/z:525.
d-2 synthesis:
referring to the synthesis of D-1, except that 8-bromobenzo [ kl ] xanthene was replaced by 9-bromobenzo [ kl ] xanthene, the compound represented by D-2 was obtained.
Mass spectrometric detection of compound D-2, m/z:525.
synthesis of D-4:
referring to the synthesis of D-1, except that 4- (4, 6-phenyl-1, 3, 5-triazin-2-yl) phenylboronic acid was replaced with (4- (4, 6-bis ([ 1,1' -biphenyl ] -4-yl) -1,3, 5-triazin-2-yl) phenyl) phenylboronic acid, the compound represented by D-4 was obtained.
The mass spectrum detection is carried out on the compound D-4, and the mass spectrum detection ratio of m/z:601.
synthesis of D-5:
(1) Synthesis of M-D-5
Referring to the synthesis of M-704, the compound represented by M-D-5 was obtained by replacing M-703 with M-803.
Mass spectrum detection is carried out on the compound shown as M-D-5, the maximum two peaks are 537 and 539, and the molecular formula of the product is determined as follows: c 34 H 20 BrNO。
(2) Synthesis of D-5
Referring to the synthesis of D-1, except that 8-bromobenzo [ kl ] xanthene therein was changed to M-D-5, a compound represented by D-5 was obtained.
Mass spectrometric detection of compound D-5, m/z:766.
synthesis of D-6:
(1) Synthesis of M-D-6
Referring to the synthesis of M-704, the M-703 was simply replaced by M-903 to give the compound represented by M-D-6.
Mass spectrum detection is carried out on the compound shown as M-D-6, the maximum two peaks are 537 and 539, and the molecular formula of the product is determined as follows: c 34 H 20 BrNO。
2) Synthesis of D-6
Referring to the synthesis of D-1, except that 8-bromobenzo [ kl ] xanthene therein was changed to M-D-6, a compound represented by D-6 was obtained.
The mass spectrum detection is carried out on the compound D-6, and the mass spectrum detection ratio of m/z:766.
device example 1
Examples the compounds of the present application were selected as electron transport materials in organic electroluminescent devices, and comparative examples D-1 to D4 were selected as electron transport materials in organic electroluminescent devices.
The organic electroluminescent device has the following structure: ITO/HIL02 (100 nm)/HT (40 nm)/EM 1 (30 nm)/electron transport material (30 nm)/LiF (0.5 nm)/Al (150 nm).
The preparation process of the organic electroluminescent device is as follows:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent conductive layer (serving as an anode) in a cleaning agent, then washing the glass substrate in deionized water, ultrasonically removing oil in a mixed solvent of acetone and ethanol, baking the glass substrate in a clean environment until the water is completely removed, cleaning the glass substrate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cation beams to improve the surface property and improve the binding capacity with a hole injection layer;
placing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, vacuum evaporating HIL02 on the anode as hole injectionEntering a layer, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 100nm;
evaporating HT on the hole injection layer in vacuum to serve as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40nm;
vacuum evaporating and plating EM1 on the hole transport layer to serve as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30nm;
respectively vacuum evaporating a comparison compound and the compound of the invention on the organic light-emitting layer to be used as an electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm and Al with the thickness of 150nm are evaporated on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
The luminance, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.
The organic electroluminescent device properties are shown in table 1 below. And testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance.
TABLE 1
Wherein, the compound represented by the formula I-1-1 is a compound formed when X is O in the formula I-1, and the compounds represented by the formula I-3-1, I-34-1, I-40-1, I-46-1, I-53-1, I-56-1, I-58-1, I-59-1, II-1-1, II-3-1, II-46-1, II-53-1, II-56-1, II-58-1 and II-59-1 are of the same structure, and the like, and all the compounds are formed when X is O in the corresponding compounds. The compound represented by I-1S is a compound wherein O in I-1 is replaced with S form.
As can be seen from the data in Table 1, compared with the comparative example, the organic electroluminescent device prepared by using the compounds of the embodiment of the application has the advantages of obviously reduced driving voltage and obviously improved current efficiency, and especially the devices using the compounds I-34-1, I-40-1, I-58-1, I-59-1, II-58-1 and II-59-1 as electron transport materials have the advantages of obviously reduced voltage and more remarkable effect.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.
Claims (10)
1. A compound is shown as a formula (I),
wherein X is selected from O or S;
A. b is independently selected from substituted or unsubstituted aromatic groups containing 6 to 40 carbon atoms;
m and n are selected from 0 or 1;
Ar 1 、Ar 2 selected from unsaturated aromatic group with 3-40 carbon atoms or one of C-1-C-7, and Ar 1 、Ar 2 One of which is selected from unsaturated aromatic groups with 3 to 40 carbon atoms, and the other is selected from one of C-1 to C-7:
wherein X 1 ～X 12 Each independently selected from NR 1 、O、S、CR 2 R 3 And X 1 And X 2 At least one selected from NR 1 ，X 3 And X 4 At least one selected from NR 1 ，X 5 And X 6 At least one selected from NR 1 ，X 7 And X 8 At least one selected from NR 1 ，X 9 And X 10 At least one is selected fromNR 1 ，X 11 And X 12 At least one selected from NR 1 ；
R 1 Selected from alkyl groups having 1 to 20 carbon atoms or aromatic groups having 6 to 40 carbon atoms; r 2 、R 3 Each independently selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, and R 2 And R 3 The carbon atoms on the above may be linked to form a ring;
the hydrogen in the compound shown in the formula (I) can be replaced by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and aryl containing 6-40 carbon atoms.
2. The compound of claim 1, wherein C-1 to C-7 can form a fused aromatic structure with at least one structure represented by the formula C-X:
wherein, in the formula C-X, the carbon atoms at the position are connected with the formulas C-1 to C-7 through chemical bonds.
3. The compound of claim 1, wherein A and B are independently selected from the group consisting of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene, and hydrogenated benzanthracene, or a combination thereof.
4. The compound of claim 1, wherein Ar is Ar 1 At least one selected from carbazole, benzocarbazole, indolocarbazole, and indenocarbazole.
5. The compound of claim 1, wherein Ar 2 At least one selected from pyridine, pyrimidine, triazine, quinoline, isoquinoline, imidazole, benzimidazole, thiazole, benzothiazole, oxazole, benzoxazole, pyrazole or purineOne kind of the method.
6. The compound of claim 1, wherein the compound is selected from one of the following formulas I-1 to I-60 and II-1 to II-60:
7. the compound of claim 6, wherein said compound further comprises an isomer of any of said compounds of formulas I-1 through I-60 and II-1 through II-60.
8. An organic electroluminescent element comprising the compound according to any one of claims 1 to 7.
9. An electromechanical light emitting device according to claim 8, wherein said compound is an electron transport layer material or a light emitting layer host material.
10. A display apparatus comprising the organic electroluminescent device according to claim 8 or 9.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010225864A (en) * | 2009-03-24 | 2010-10-07 | Yamamoto Chem Inc | Organic transistor |
| US20150001479A1 (en) * | 2013-07-01 | 2015-01-01 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| US20160133857A1 (en) * | 2014-11-10 | 2016-05-12 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| US20170331051A1 (en) * | 2016-05-13 | 2017-11-16 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
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| JP2010225864A (en) * | 2009-03-24 | 2010-10-07 | Yamamoto Chem Inc | Organic transistor |
| US20150001479A1 (en) * | 2013-07-01 | 2015-01-01 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| US20160133857A1 (en) * | 2014-11-10 | 2016-05-12 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| US20170331051A1 (en) * | 2016-05-13 | 2017-11-16 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
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