CN116283950A - Phenoxazine-like compound, preparation method and application thereof, and electroluminescent device - Google Patents
Phenoxazine-like compound, preparation method and application thereof, and electroluminescent device Download PDFInfo
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- CN116283950A CN116283950A CN202310275369.2A CN202310275369A CN116283950A CN 116283950 A CN116283950 A CN 116283950A CN 202310275369 A CN202310275369 A CN 202310275369A CN 116283950 A CN116283950 A CN 116283950A
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- phenoxazine
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 33
- -1 9, 9-dimethylfluorenyl group Chemical group 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000005842 heteroatom Chemical group 0.000 claims description 51
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 22
- 239000007924 injection Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 17
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 17
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000004957 naphthylene group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 10
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
- 125000003277 amino group Chemical class 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 8
- 235000011009 potassium phosphates Nutrition 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 7
- 125000005551 pyridylene group Chemical group 0.000 claims description 7
- 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 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005576 pyrimidinylene group Chemical group 0.000 claims 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 claims description 6
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 4
- 241000720974 Protium Species 0.000 claims description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052722 tritium Inorganic materials 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 29
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 description 23
- 239000011259 mixed solution Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000009616 inductively coupled plasma Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 150000001716 carbazoles Chemical group 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical group C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 229940125961 compound 24 Drugs 0.000 description 2
- 229940125844 compound 46 Drugs 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000004038 photonic crystal Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention belongs to the technical field of semiconductors, and particularly relates to a phenoxazine-like compound, a preparation method and application thereof, and an electroluminescent device. The phenoxazine-like compound provided by the invention has a structure shown as a formula I. The structure of the phenoxazine-like compound provided by the invention contains a phenoxazine rigid group, so that the structural stability of the compound is improved; meanwhile, the compound provided by the invention takes the phenoxazine-like structure as a mother nucleus to connect a plurality of groups, and the phenoxazine-like structureThe structural groups contain strong electronicity, so that a plurality of groups are mutually crossed and separated, free rotation of the groups is avoided, the compound has higher density, the refractive index of the material is improved, and the light extraction rate is improved. The light extraction layer of the electroluminescent device is prepared by taking the phenoxazine-like compound provided by the invention as a raw material, so that the light extraction efficiency of the OLED device can be effectively improved.
Description
Technical Field
The invention belongs to the technical field of semiconductors, and particularly relates to a phenoxazine-like compound, a preparation method and application thereof, and an electroluminescent device.
Background
With the development of technology, the OLED display technology has been widely applied to the fields of smart phones, tablet computers, and the like. However, a large gap exists between the external quantum efficiency and the internal quantum efficiency of the traditional OLED device, so that the OLED device has lower light-emitting efficiency, and the development and application fields of the OLED are severely restricted.
At present, the method for improving the light-emitting efficiency of the OLED device mainly comprises the steps of forming folds on the light-emitting surface of a substrate, adding photonic crystals, micro-lens array (MLA) structures or adding a surface light extraction layer. Wherein, forming wrinkles or adding photonic crystals on the light-emitting surface of the substrate can improve the light-emitting efficiency of the OLED device, but can affect the radiation spectrum angular distribution of the OLED, thereby affecting the performance of the OLED device. The surface light extraction layer is added on the surface of the substrate, so that the light extraction efficiency of the OLED device can be improved while the performance of the OLED device is ensured, the material for preparing the light extraction layer is a light extraction material, the existing light extraction material is limited in improvement of the light extraction efficiency of the OLED device, and development of the light extraction material capable of greatly improving the light extraction efficiency of the OLED device is needed.
Disclosure of Invention
In view of the above, the invention provides a phenoxazine-like compound, a preparation method and application thereof, and an electroluminescent device, and the light extraction layer of the electroluminescent device prepared by the phenoxazine-like compound provided by the invention can effectively improve the light extraction efficiency of the OLED device.
In order to solve the technical problems, the invention provides a phenoxazine-like compound, which has a structure shown in a formula I:
wherein Z is N or-CH;
L 1 、L 2 、L 3 independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 1 、R 2 、R 3 independently substituted or unsubstituted C 6 ～C 30 Aryl, a group of the structure shown in any one of formulae 2 to 6, or a substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; and R is 1 、R 2 And R is 3 At least one of the groups is a structure shown in formula 2, formula 3 or formula 4;
wherein X is O or S;
X 1 o, S or N-R 12 ；
L 4 、L 5 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
L 6 is substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 6 is cyano, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl or containing one or more Substituted or unsubstituted C of a plurality of hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 4 、R 5 、R 7 、R 8 and R is 9 Independently is a hydrogen atom, cyano group, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, heteroaryl-substituted amino groups or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 10 、R 11 、R 12 independently C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
the substituent groups in the substituted aryl, the substituted heteroaryl, the substituted arylene and the substituted heteroarylene are independently halogen, cyano, protium, deuterium, tritium and C 1 ～C 20 Alkyl, C 6 ～C 20 Aryl or C 5 ～C 20 Heteroaryl groups.
Preferably, the phenoxazine-like compound has a structure as shown in any one of formulas I-1 to I-4:
preferably, the phenoxazine-like compound has a structure as shown in any one of formulas I-5 to I-14:
preferably, the phenoxazine-like compound has a structure as shown in formula I-15:
preferably, the phenoxazine-like compound has a structure as shown in formula I-16:
Preferably, the L 1 、L 2 、L 3 、L 4 、L 5 Independently is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthylene group;
the L is 6 Is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthylene group;
The R is 4 、R 5 、R 7 、R 8 、R 9 Independently a hydrogen atom, deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenylA substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzimidazolyl group;
the R is 6 Is cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl;
The R is 10 、R 11 、R 12 Independently are methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazoleA group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzimidazolyl group;
the substituent in the substituent group is one or more of cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, pyridyl, biphenyl, naphthyl, naphthyridinyl, furyl, dibenzofuranyl and carbazolyl.
Preferably, the phenoxazine-like compound has a structure represented by any one of the following structural formulas:
the invention also provides a preparation method of the phenoxazine-like compound, which comprises the following steps:
mixing a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, palladium acetate, a potassium phosphate aqueous solution and a first organic solvent, and performing a first reflux reaction to obtain an intermediate with a structure shown in a formula M;
mixing the intermediate, a substance with a structure shown in a formula D, a second organic solvent, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus for a second reflux reaction to obtain a phenoxazine-like compound with a structure shown in a formula I;
The invention also provides an application of the phenoxazine-like compound in electroluminescent devices, wherein the phenoxazine-like compound is prepared by the technical scheme or the preparation method.
The invention also provides an electroluminescent device, which comprises a substrate, a first electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, a hole blocking layer/electron transport layer, an electron injection layer, a second electrode layer and a light extraction layer which are sequentially laminated, wherein the light extraction layer is prepared from the phenoxazine-like compound according to the technical scheme or the phenoxazine-like compound prepared by the preparation method.
The invention provides a phenoxazine-like compound, which has a structure shown in a formula I:
wherein Z is N or-CH; l (L) 1 、L 2 、L 3 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; r is R 1 、R 2 、R 3 Independently substituted or unsubstituted C 6 ～C 30 Aryl, a group of the structure shown in any one of formulas 2 to 6, or a substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; and R is 1 、R 2 And R is 3 At least one of which is of formula 2, formula 3 or
A group of the structure shown in formula 4;
wherein X is O or S; x is X 1 O, S or N-R 12 ；L 4 、L 5 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; l (L) 6 Is substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; r is R 6 Is cyano, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; r is R 4 、R 5 、R 7 、R 8 And R is 9 Independently is a hydrogen atom, cyano group, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, heteroaryl-substituted amino groups or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; r is R 10 、R 11 、R 12 Independently C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; the substituent groups in the substituted aryl, the substituted heteroaryl, the substituted arylene and the substituted heteroarylene are independently halogen, cyano, protium, deuterium, tritium and C 1 ～C 20 Alkyl, C 6 ～C 20 Aryl or C 5 ～C 20 Heteroaryl groups. The structure of the phenoxazine-like compound contains a phenoxazine-like rigid group, so that the structural stability of the compound is improved; meanwhile, the compound provided by the invention takes the phenoxazine-like structure as a mother nucleus to connect a plurality of groups, the groups of the phenoxazine-like structure contain strong electronicity, the groups are mutually crossed and separated, free rotation of the groups is avoided, the compound has higher density, the refractive index of the material is improved, and the refractive index is higher than the corresponding light extraction rate. The light extraction layer of the electroluminescent device is prepared by taking the phenoxazine-like compound provided by the invention as a raw material, so that the light extraction efficiency of the OLED device can be effectively improved.
Drawings
Fig. 1 is a schematic structural diagram of an electroluminescent device prepared in an embodiment, in which 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer/electron transport layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a light extraction layer.
Detailed Description
The invention provides a phenoxazine-like compound, which has a structure shown in a formula I:
in the present invention, the phenoxazine-like compound preferably has a structure as shown in any one of formulas I-1 to I-4:
in the present invention, Z is C when a substituent is attached to Z.
In the present invention, the phenoxazine-like compound preferably has a structure as shown in any one of formulas I-5 to I-14:
in the present invention, the phenoxazine-like compound preferably has a structure represented by the formula I-15:
in the present invention, the phenoxazine-like compound preferably has a structure represented by the formula I-16:
in the present invention, Z is N or-CH, preferably-CH. In the present invention, Z is C when a substituent is attached to Z.
In the present invention, L 1 、L 2 、L 3 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 Is a heteroarylene group; preferably a singleA bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenylene group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthyridine group.
In the present invention, R 1 、R 2 、R 3 Independently substituted or unsubstituted C 6 ～C 30 Aryl, a group of the structure shown in any one of formulas 2 to 6, or a substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 Heteroaryl of (a). In the present invention, R 1 、R 2 And R is 3 At least one of the groups is a group having a structure represented by formula 2, formula 3 or formula 4.
In the present invention, X is O or S, preferably O.
In the present invention, X 1 O, S or N-R 12 . In the present invention, R 12 Preferably C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 More preferably methyl, ethyl, propyl, isopropyl, t-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, or a substituted or unsubstituted pyrimidinyl groupSubstituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl.
In the present invention, L 4 、L 5 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 Preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazole group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthyridine group.
In the present invention, L 6 Is substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 Preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent phenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazole group, a substituted or unsubstituted quinolylene group A substituted or unsubstituted isoquinolinyl group or a substituted or unsubstituted naphthyridinyl group.
In the present invention, R 6 Is cyano, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 Preferably cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl.
In the present invention, R 4 、R 5 、R 7 、R 8 And R is 9 Independently is a hydrogen atom, cyano group, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, heteroaryl-substituted amino groups or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 Preferably hydrogen atom, deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazoleA group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzimidazolyl group.
In the present invention, R 10 、R 11 Independently C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 Preferably methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl.
In the present invention, the heteroatom in the heteroarylene or heteroaryl group includes nitrogen, oxygen or sulfur, preferably oxygen or sulfur.
In the invention, the substituents in the substituted aryl, substituted heteroaryl, substituted arylene and substituted heteroarylene are independently halogen,Cyano, protium, deuterium, tritium, C 1 ～C 20 Alkyl, C 6 ～C 20 Aryl or C 5 ～C 20 Heteroaryl groups.
In the present invention, the phenoxazine-like compound preferably has a structure represented by any one of the following structural formulas:
more preferably
The invention also provides a preparation method of the phenoxazine-like compound, which comprises the following steps:
mixing a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, palladium acetate, a potassium phosphate aqueous solution and a first organic solvent, and performing a first reflux reaction to obtain an intermediate with a structure shown in a formula M;
mixing the intermediate, a substance with a structure shown in a formula D, a second organic solvent, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus for a second reflux reaction to obtain a phenoxazine-like compound with a structure shown in a formula I;
The invention mixes a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, palladium acetate, potassium phosphate aqueous solution and first organic solvent, and carries out first reflux reaction to obtain an intermediate with a structure shown in a formula M. In the present invention, the mixing preferably includes the steps of:
Mixing a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, a first organic solvent and palladium acetate for the first time to obtain a first mixed solution;
an aqueous potassium phosphate solution is added to the first mixed solution.
The invention mixes a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, a first organic solvent and palladium acetate for the first time to obtain a first mixed solution. In the present invention, the first organic solvent is preferably N, N-Dimethylformamide (DMF). The amount of the first organic solvent is not particularly limited as long as the material can be completely dissolved. In the present invention, the molar ratio of the substance having the structure represented by formula a to the substance having the structure represented by formula B is preferably 1:2 to 2.5, more preferably 1:2.2 to 2.3. In the present invention, the palladium acetate (Pb (OAc) 2 ) Is a reaction catalyst. In the present invention, the molar ratio of the substance having the structure represented by formula A to palladium acetate is preferably 1:0.01 to 0.03.
In the present invention, the first mixing is preferably performed under stirring. The stirring is not particularly limited as long as it can be uniformly mixed.
After the first mixed solution is obtained, the invention adds the potassium phosphate aqueous solution to the first mixed solution. In the present invention, the potassium phosphate (K 3 PO 4 ) The molar concentration of the aqueous solution is preferably 0.0098 to 0.012mol/mL, more preferably 0.01mol/mL. In the present invention, the ratio of the molar amount of the substance having the structure represented by formula A to the volume of the aqueous potassium phosphate solution is preferably 0.02mol:2.8 to 3.2mL, more preferably 0.02mol:3mL. In the present invention, the stirring is preferably accompanied during the addition of the aqueous potassium phosphate solution. The stirring is not particularly limited as long as it can be uniformly mixed.
In the present invention, the temperature of the first reflux reaction is preferably 140 to 160 ℃, more preferably 150 ℃; the time of the first reflux reaction is preferably 9 to 11 hours, more preferably 10 hours. The present invention preferably uses a spot-plating method to determine the end point of the first reflow reaction.
In the present invention, the first reflux reaction is preferably performed under a protective atmosphere, which is preferably nitrogen or argon, more preferably nitrogen.
In the present invention, the reaction equation of the first reflux reaction is shown in formula 1:
in the present invention, the first reflux reaction further preferably includes: and (3) cooling the system after the first reflux reaction, mixing with water, filtering the mixture obtained by mixing, concentrating the filtrate obtained by filtering, and purifying by a silica gel column to obtain the intermediate with the structure shown in the formula M. In the present invention, the cooling is preferably air cooling, and the temperature of the cooled system is preferably 20 to 35 ℃, more preferably 25 to 30 ℃. The invention has no special requirement on the filtration, and can be realized by adopting a conventional mode in the field. In the present invention, the concentration is preferably performed in a vacuum drying oven. The invention removes most of the solvent in the filtrate through concentration, and the invention has no special requirement on the concentration time, so long as the most of the solvent in the filtrate can be removed. The method has no special requirement on the mode of passing through the silica gel column, and can be carried out by adopting the conventional mode in the field.
After the intermediate is obtained, the intermediate, a substance with a structure shown in a formula D, a second organic solvent, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus are mixed for carrying out a second reflux reaction, so that the phenoxazine-like compound with the structure shown in the formula I is obtained. In the present invention, Q in formula D is preferably-Cl, -Br or-I, more preferably-Br. In the present invention, the mixing preferably includes the steps of:
mixing the intermediate, a substance with a structure shown in a formula D and a second organic solvent to obtain a second mixed solution;
sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus are added to the second mixed melt.
The invention mixes the intermediate, the substance with the structure shown in the formula D and the second organic solvent to obtain a second mixed solution. In the present invention, the second organic solvent is preferably toluene. The invention has no special requirement on the dosage of the second organic solvent, so long as the material can be completely dissolved. In the present invention, the molar ratio of the intermediate to the substance having the structure represented by formula D is preferably 1:1 to 1.2, more preferably 1:1.2. In the present invention, the mixing is preferably performed under stirring, and the stirring is not particularly limited as long as the mixing can be uniformly performed.
After the second mixed solution is obtained, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus are added to the second mixed solution. In the present invention, the molar ratio of the intermediate to sodium t-butoxide is preferably 1:3 to 3.5, more preferably 1:3.
In the present invention, the temperature of the second reflux reaction is preferably 100 to 110 ℃, more preferably 105 ℃; the time of the second reflux reaction is preferably 22 to 26 hours, more preferably 24 hours. The present invention preferably uses the spot-plating method to determine the end point of the second reflow reaction.
In the present invention, the second reflux reaction is preferably performed under a protective atmosphere, which is preferably nitrogen or argon, more preferably nitrogen.
In the present invention, the second reflux reaction further preferably includes: and cooling the second reflux reaction system, filtering, and spin-evaporating the filtrate obtained by filtering and passing through a silica gel column to obtain the phenoxazine-like compound with the structure shown in the formula I. In the present invention, the cooling is preferably air cooling, and the temperature of the cooled system is preferably 20 to 35 ℃, more preferably 25 to 30 ℃. The invention has no special requirement on the filtration, and can be realized by adopting a conventional mode in the field. The invention removes most of the solvent in the system through rotary evaporation, has no special requirement on rotary evaporation, and can be realized by adopting a conventional mode in the field. The method has no special requirement on the mode of passing through the silica gel column, and can be carried out by adopting the conventional mode in the field. In the present invention, the silica gel column is preferably a neutral silica gel column.
The invention also provides an application of the phenoxazine-like compound in electroluminescent devices, wherein the phenoxazine-like compound is prepared by the technical scheme or the preparation method.
The invention also provides an electroluminescent device, which comprises a substrate, a first electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, a hole blocking layer/electron transport layer, an electron injection layer, a second electrode layer and a light extraction layer which are sequentially laminated;
the light extraction layer is prepared from the phenoxazine-like compound prepared by the technical scheme or the phenoxazine-like compound prepared by the preparation method.
In the present invention, the electroluminescent device includes a substrate. In the present invention, the substrate preferably includes a transparent substrate or an opaque substrate; the transparent substrate is preferably glass or transparent plastic, more preferably glass; the opaque substrate is preferably a silicon substrate. The invention determines the use direction of the substrate according to different mechanical strength, thermal stability, transparency, surface smoothness and waterproofness of the substrate.
In the present invention, the electroluminescent device includes a first electrode layer. In the present invention, the first electrode in the first electrode layer is preferably an anode. In the present invention, the first electrode is preferably a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the present invention, when the first electrode is a transmissive electrode, the first electrode is preferably formed of a transparent metal oxide; the transparent metal oxide is preferably Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), or Indium Tin Zinc Oxide (ITZO). In the present invention, when the first electrode is a semi-transmissive electrode or a reflective electrode, the first electrode is preferably one or more of Ag, mg, al, pt, pd, au, ni, nd, ir and Cr. In the present invention, the thickness of the first electrode layer is preferably 50 to 500nm.
In the present invention, the electroluminescent device includes a hole injection layer. In the present invention, the thickness of the hole injection layer is preferably 5 to 100nm. The method for obtaining the hole injection layer is not particularly limited, and a conventional method in the art can be adopted.
In the present invention, the electroluminescent device includes a hole transport layer. In the present invention, the thickness of the hole transport layer is preferably 5 to 200nm. The hole transport layer is not particularly limited, and may be obtained by a conventional method in the art.
In the present invention, the electroluminescent device includes an electron blocking layer. In the present invention, the thickness of the electron blocking layer is preferably 5 to 200nm. The method for obtaining the electron blocking layer is not particularly limited, and a conventional method in the field can be adopted.
In the present invention, the electroluminescent device includes a light emitting layer. In the present invention, the light emitting layer preferably includes a host material, which is a green host material common in the art, and a doping material, which is a doping material common in the art. In the present invention, the host material is preferably a single host material or a double host material. In the present invention, the thickness of the light emitting layer is preferably 5 to 50nm. The invention can adjust the thickness of the light emitting layer to optimize the light emitting efficiency and the driving voltage.
In the present invention, the electroluminescent device comprises a hole blocking layer/electron transport layer. In the present invention, the hole blocking layer/electron transport layer material is a material that easily receives electrons of a cathode and transfers the received electrons to a light emitting layer, and has high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices known in the art may be used. In the present invention, the thickness of the hole blocking layer/electron transport layer is preferably 10 to 80nm.
In the present invention, the electroluminescent device includes an electron injection layer. In the present invention, the electron injection layer material is preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art can be used. In the present invention, the thickness of the electron injection layer is preferably 0.1 to 5nm.
In the present invention, the electroluminescent device includes a second electrode layer. In the present invention, the second electrode in the second electrode layer is preferably a cathode. In the present invention, the second electrode is preferably a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode preferably comprises Li, yb, ca, liF/Ca, liF/Al, al, mg, baF, ba, ag or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode preferably comprises Ag, mg, yb, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti or a compound or mixture thereof. In the present invention, the thickness of the second electrode layer is preferably dependent on the material used.
In the present invention, the electroluminescent device includes a light extraction layer. In the present invention, the thickness of the light extraction layer is preferably 20 to 100nm, more preferably 30 to 80nm.
The invention has no special requirement on the preparation method of the electroluminescent device, and can be realized by adopting the conventional method in the field. The invention preferably adopts vacuum deposition, vacuum evaporation, spin coating, casting, LB method, ink-jet printing, laser printing or LITI method to prepare the electroluminescent device.
The technical solutions provided by the present invention are described in detail below in conjunction with examples for further illustrating the present invention, but they should not be construed as limiting the scope of the present invention.
Example 1
0.02mol of raw material A1,0.044mol of raw material B1 and 0.0002mol of palladium acetate are dissolved in 150ml of DMF under the protection of nitrogen under the stirring condition to obtain a first mixed solution; to the first mixed solution was added 3mL of K having a molar concentration of 0.01mol/mL 3 PO 4 Carrying out a first reflux reaction on the aqueous solution at 150 ℃ for 10 hours, (determining that the reaction is complete by a sampling point plate), naturally cooling to 25 ℃, mixing with 100mL of water, filtering, concentrating the filtrate obtained by filtering in a vacuum drying oven, and purifying by a silica gel column to obtain an intermediate M1;
Mixing 0.01mol of intermediate M1,0.012mol of raw material D1 and 150ml of toluene under the protection of nitrogen under the condition of stirring to obtain a second mixed solution; adding 5X 10 to the second mixed solution -5 mol Pd 2 (dba) 3 ，5×10 -5 mol P(t-Bu) 3 Performing a second reflux reaction of 0.03mol of sodium tert-butoxide at 105deg.C for 24h (sampling spot plate, no bromide residue, complete reaction), and naturally cooling to 25deg.C
Filtering, spin-evaporating the filtrate, and passing through neutral silica gel column to obtain
Denoted as compound 1, elemental analysis structure (moleculeC (C) 56 H 33 N 3 O 4 ): theoretical value C,82.84; h,4.10; n,5.18; inductively coupled plasma spectrometer test value C,82.87; h,4.17; n,5.15.MS: the exact mass was 811.25, found molecular weight 812.27.
The first reflux reaction equation is:
the second reflux reaction equation is:
an intermediate was prepared according to the procedure for the preparation of intermediate M1 of example 1, except for the differences described in table 1.
TABLE 1 Structure of starting materials and products for the preparation of intermediate M
Example 2: synthesis of Compound 2
A phenoxazine-like compound was prepared as described in example 1, denoted as compound 2, except that starting material D2 was used in place of starting material D1; elemental analysis structure (molecular formula C) 56 H 33 N 3 O 4 ): theoretical value C,82.84; h,4.10; n,5.18; inductively coupled plasma spectrometer test value C,82.88; h,4.16; n,5.14.MS: the exact mass was 811.25, found molecular weight 812.26.
Example 3: synthesis of Compound 23
A phenoxazine-like compound was prepared as described in example 1, designated compound 23, except that starting material D3 was used in place of starting material D1; intermediate M2 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 54 H 33 N 3 OS 2 ): theoretical value C,80.67; h,4.14; n,5.23; s,7.98; inductively coupled plasma spectrometer test value C,80.69; h,4.19; n,5.19; s,7.96.MS: the exact mass was 803.21, found molecular weight 804.24.
Example 4: synthesis of Compound 24
A phenoxazine-like compound, designated compound 24, was produced as in example 1, except that starting material D4 was used in place of starting material D1; intermediate M2 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 56 H 35 N 3 OS 2 ): theoretical value C,81.03; h,4.25; n,5.06; s,7.72; inductively coupled plasma spectrometer test value C,81.06; h,4.31; n,5.02; s,7.76.MS: the exact mass was 829.22, found molecular weight 830.23.
Example 5: synthesis of Compound 45
A phenoxazine-like compound, designated compound 45, was produced as in example 1, except that starting material D5 was used in place of starting material D1; intermediate M3 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 65 H 40 N 6 O 3 ): theoretical value C,81.92; h,4.23; n,8.82; inductively coupled plasma spectrometer test value C,81.95; h,4.21; n,8.87.MS: the exact mass was 952.32, found molecular weight 953.36.
Example 6: synthesis of Compound 46
A phenoxazine-like compound, designated compound 46, was produced as in example 1, except that starting material D6 was used in place of starting material D1; intermediate M3 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 68 H 44 N 4 O 3 ): theoretical value C,84.63; h,4.60; n,5.81; inductively coupled plasma spectrometer test value C,84.64; h,4.63; n,5.84.MS: the exact mass was 964.34, found molecular weight 965.31.
Example 7: synthesis of Compound 135
A phenoxazine-like compound, designated compound 135, was prepared as in example 1, except that starting material D7 was used in place of starting material D1; intermediate M4 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 48 H 29 N 3 O 3 ): theoretical value C,82.86; h,4.20; n,6.04; inductively coupled plasma spectrometer test value C,82.83; h,4.17; n,6.01.MS: the exact mass was 695.22, found molecular weight 696.17.
Example 8: synthesis of Compound 136
A phenoxazine-like compound, designated compound 136, was prepared as in example 1, except that starting material D8 was used in place of starting material D1; intermediate M4 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 50 H 31 N 3 O 3 ): theoretical value C,83.20; h,4.33; n,5.82; inductively coupled plasma spectrometer test value C,83.16; h,4.33; n,5.85.MS: the exact mass was 721.24, found molecular weight 722.19.
Example 9: synthesis of Compound 157
A phenoxazine-like compound, designated compound 157, was produced as in example 1, except that starting material D9 was used in place of starting material D1; intermediate M5 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 50 H 31 N 3 OS 2 ): theoretical value C,79.66; h,4.14; n,5.57; s,8.50; inductively coupled plasma spectrometer test value C,79.62; h,4.19; n,5.54; s,8.51.MS: the exact mass was 753.19, found molecular weight 754.18.
Example 10: synthesis of Compound 158
A phenoxazine-like compound, designated compound 158, was prepared as in example 1, except that starting material D10 was used in place of starting material D1; intermediate M5 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 53 H 35 N 3 OS 2 ): theoretical value C,80.17; h,4.44; n,5.29; s,8.08; inductively coupled plasma spectrometer test value C,80.14; h,4.48n,5.27; s,8.03.MS: the exact mass was 793.22, found molecular weight 794.13.
Example 11: synthesis of Compound 281
A phenoxazine-like compound was prepared as described in example 1, designated compound 281, except that starting material D11 was used in place of starting material D1; intermediate M6 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 61 H 36 N 2 O 4 ): theoretical value C,85.10; h,4.21; n,3.25; inductively coupled plasma spectrometer test value C,85.14; h,4.24; n,3.22.MS: the exact mass was 860.27, found molecular weight 861.21.
Example 12: synthesis of Compound 282
A phenoxazine-like compound, designated compound 282, was prepared as in example 1, except that starting material D12 was used in place of starting material D1; intermediate M7 is substituted for intermediate M1; elemental analysis structure (molecular formula C) 61 H 36 N 2 O 4 ): theoretical value C,85.10; h,4.21; n,3.25; inductively coupled plasma spectrometer test value C,85.14; h,4.25; n,3.22.MS: the exact mass was 860.27, found molecular weight 861.22.
An electroluminescent device was prepared as follows:
a) Taking transparent glass as a substrate layer 1, washing an anode layer 2 (Ag (100 nm)), firstly using isopropanol and deionized water to carry out ultrasonic cleaning for 10min, then using ultraviolet rays to irradiate for 10min, and exposing the anode layer to ozone for cleaning;
b) Evaporating HAT-CN with the thickness of 10nm on the anode layer 2 by a vacuum evaporation mode to form a hole injection layer 3;
c) HT-1 with a thickness of 140nm is evaporated on the hole injection layer 3 by a vacuum evaporation method to form a hole transport layer 4;
d) EB-1 having a thickness of 30nm was vapor deposited as an electron blocking layer 5 on the hole transport layer 4 by vacuum vapor deposition;
e) A luminescent layer 6 with the thickness of 40nm is evaporated on the electron blocking layer 5, GH-2 and GH-1 are used as main materials, GD-1 is used as doping materials, and the mass ratio of GH-2, GH-1 and GD-1 is 45:45:10;
f) Evaporating ET-1 and Liq with the mass ratio of 1:1 on the luminescent layer 6 by a vacuum evaporation mode to serve as a hole blocking layer/electron transport layer 7, wherein the thickness of the hole blocking layer/electron transport layer 7 is 40nm;
g) Over the hole blocking layer/electron transport layer 7, liF with a thickness of 1nm was vacuum evaporated as an electron injection layer 8;
h) On the electron injection layer 8, mg and Ag with the mass ratio of 1:9 are used as a cathode layer 9 by vacuum evaporation, and the thickness of the cathode layer 9 is 15nm;
i) Evaporating a light extraction layer material with the thickness of 70nm on the cathode layer 9 by a vacuum evaporation mode to obtain an electroluminescent device as a light extraction layer 10; the light extraction layer material is the phenoxazine-like compound or Ref-1 prepared in examples 1-12;
wherein HAT-CN is
HT-1 is->
EB-1 is->
GD-1 is->
ET-1 is->
GH-1 is->
GH-2 is->
Liq is->
Ref-1 is->
The structure of the electroluminescent device is shown in fig. 1, wherein 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer/electron transport layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a light extraction layer;
electroluminescent devices were prepared using the phenoxazine-like compounds prepared in examples 1 to 12 and Ref-1 as light extraction layer materials, except for referring to Table 2.
Table 2 composition of electroluminescent device
At 10mA/cm using an IVL (Current-Voltage-Brightness) test system 2 The current efficiency of the prepared electroluminescent device was measured at the current density of (2), and the measurement results are shown in table 3.
TABLE 3 Properties of electroluminescent devices prepared
From the results of Table 3, it can be seen that the present invention, which uses a phenoxazine-like compound as the light extraction layer of an OLED light emitting device, can effectively improve the light extraction efficiency of the OLED light emitting device.
Although the foregoing embodiments have been described in some, but not all, embodiments of the invention, it should be understood that other embodiments may be devised in accordance with the present embodiments without departing from the spirit and scope of the invention.
Claims (10)
1. A phenoxazine-like compound is characterized by having a structure shown in a formula I:
wherein Z is N or-CH;
L 1 、L 2 、L 3 independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene group or containSubstituted or unsubstituted C of one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 1 、R 2 、R 3 independently substituted or unsubstituted C 6 ～C 30 Aryl, a group of the structure shown in any one of formulae 2 to 6, or a substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur; and R is 1 、R 2 And R is 3 At least one of the groups is a structure shown in formula 2, formula 3 or formula 4;
wherein X is O or S;
X 1 o, S or N-R 12 ；
L 4 、L 5 Independently a single bond, substituted or unsubstituted C 6 ～C 30 Arylene, substituted or unsubstituted C containing one or more heteroatoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
L 6 is substituted or unsubstituted C 6 ～C 30 Arylene or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 6 is cyano, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 4 、R 5 、R 7 、R 8 and R is 9 Independently is a hydrogen atom, cyano group, C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substitution orUnsubstituted C 6 ～C 30 Aryl, heteroaryl-substituted amino groups or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
R 10 、R 11 、R 12 independently C 1 ～C 10 Alkyl, C of (2) 1 ～C 10 Alkoxy, substituted or unsubstituted C 6 ～C 30 Aryl, or substituted or unsubstituted C containing one or more hetero atoms 5 ～C 30 The heteroatom comprising nitrogen, oxygen or sulfur;
the substituent groups in the substituted aryl, the substituted heteroaryl, the substituted arylene and the substituted heteroarylene are independently halogen, cyano, protium, deuterium, tritium and C 1 ～C 20 Alkyl, C 6 ～C 20 Aryl or C 5 ～C 20 Heteroaryl groups.
2. The phenoxazine-like compound according to claim 1, wherein the phenoxazine-like compound has a structure represented by any one of formulas I-1 to I-4:
3. the phenoxazine-like compound according to claim 1, wherein the phenoxazine-like compound has a structure represented by any one of formulas i-5 to i-14:
4. the phenoxazine-like compound according to claim 1, wherein the phenoxazine-like compound has a structure represented by the formula i-15:
5. the phenoxazine-like compound according to claim 1, wherein the phenoxazine-like compound has a structure represented by the formula i-16:
6. the phenoxazine-like compound according to any one of claims 1 to 5, wherein L 1 、L 2 、L 3 、L 4 、L 5 Independently is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthylene group;
The L is 6 Is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted naphthylene group;
the R is 4 、R 5 、R 7 、R 8 、R 9 Independently is a hydrogen atom, deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazole;
The R is 6 Is cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzoxazolyl, or substituted or unsubstituted benzimidazolyl;
the R is 10 、R 11 、R 12 Independently methyl, ethyl, propyl, isopropyl, tert-butyl, methylAn oxy group, an ethoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzimidazolyl group;
The substituent in the substituent group is one or more of cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, pyridyl, biphenyl, naphthyl, naphthyridinyl, furyl, dibenzofuranyl and carbazolyl.
7. The phenoxazine-like compound according to claim 6, wherein the phenoxazine-like compound has a structure represented by any one of the following structural formulas:
8. the process for producing a phenoxazine-like compound according to any one of claims 1 to 7, comprising the steps of:
mixing a substance with a structure shown in a formula A, a substance with a structure shown in a formula B, palladium acetate, a potassium phosphate aqueous solution and a first organic solvent, and performing a first reflux reaction to obtain an intermediate with a structure shown in a formula M;
mixing the intermediate, a substance with a structure shown in a formula D, a second organic solvent, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris (tert-butyl) phosphorus for a second reflux reaction to obtain a phenoxazine-like compound with a structure shown in a formula I;
9. Use of a phenoxazine-like compound according to any one of claims 1 to 7 or a phenoxazine-like compound according to claim 8 in an electroluminescent device.
10. An electroluminescent device comprising a substrate, a first electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer/electron transport layer, an electron injection layer, a second electrode layer, and a light extraction layer which are laminated in this order, wherein the light extraction layer is prepared from the phenoxazine-like compound according to any one of claims 1 to 7 or the phenoxazine-like compound prepared by the preparation method according to claim 8.
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