CN111825600A - Organic photoelectric material containing C60 condensed ring and preparation method and application thereof - Google Patents
Organic photoelectric material containing C60 condensed ring and preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 91
- 238000002360 preparation method Methods 0.000 title claims description 32
- 238000002347 injection Methods 0.000 claims abstract description 44
- 239000007924 injection Substances 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- -1 tertiary amine cation Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 28
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical group ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 20
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910003472 fullerene Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000005691 oxidative coupling reaction Methods 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- DUWVJDMUIDJMDV-UHFFFAOYSA-N azanylidyne(nitrosulfonyloxy)methane Chemical compound [O-][N+](=O)S(=O)(=O)OC#N DUWVJDMUIDJMDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical class 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- ASQOQJYHIYYTEJ-GBESFXJTSA-N (1r,7s,9as)-7-decyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ol Chemical compound O[C@@H]1CCCN2C[C@@H](CCCCCCCCCC)CC[C@H]21 ASQOQJYHIYYTEJ-GBESFXJTSA-N 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 2
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 2
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 2
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Photovoltaic Devices (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic photoelectric material containing C60 condensed rings, wherein the organic photoelectric material containing C60 condensed rings has a structure shown in a formula I; the organic photoelectric material provided by the invention has a C60 condensed ring framework, so that the organic photoelectric material has good thermal stability and is beneficial to improving the film-forming property in the later processing and using process; c60 condensed rings in the organic photoelectric material are cooperated with substituents such as halogen, cyano and the like with strong electron-withdrawing performance, so that molecules are endowed with strong reduction potential, and the organic photoelectric material can be used as a guest material to improve the hole injection performance. The organic photoelectric material containing the C60 condensed ring is used as a hole injection layer object material of an OLED device, so that the injection of charges can be effectively increased, the driving voltage of the OLED device is reduced, the overall efficiency of the device is improved, and the service life of the device is prolonged.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic photoelectric material, and a preparation method and application thereof.
Background
The research of organic electroluminescent devices, which use organic anthracene crystals as light emitting materials, started in 1963, but the driving voltage of the devices was as high as 400V, and the efficiency and lifetime of the devices were inferior to those of inorganic electroluminescent devices, thus failing to attract attention. Until the time of the year 1987, it was,tang et al, a method of vacuum deposition coating, firstly using an arylamine derivative HTM1 as a hole transport layer and 8-hydroxyquinoline aluminum as a light emitting layer, realized a luminance of 1000cd/m at a driving voltage of 10V2Green light emission of (2). The organic electroluminescent device has been a focus of research due to its advantages of low volume, low driving voltage, fast response, wide viewing angle, and capability of realizing large-area full-color flat panel display, and the research focus is not limited to the organic electroluminescent theory, but has a significant breakthrough in the practical performance of the device.
In order to further improve the brightness, efficiency and lifetime of the organic electroluminescent device, a multilayer structure is generally used in the device, and the multilayer structure includes a light emitting layer and various auxiliary organic layers, such as a hole injection layer, a hole transport layer, an electron transport layer, etc., which function to improve the injection efficiency of carriers between interfaces of the layers and balance the transport of carriers between the layers, thereby improving the brightness and efficiency of the device.
CN105348300A discloses an organic photoelectric material, a preparation method and a use thereof, wherein the organic photoelectric material is formed by connecting indole groups on the basis of phenoxazine to form a carbazole structure, and further introduces R through chemical modification1And R2Structural groups forming a twisted non-planar structure; the non-planar structure effectively avoids the tight accumulation of molecules, improves the fluorescence quantum efficiency, shows higher thermal stability and glass transition temperature, is easy to form a good amorphous film, and can obtain more stable effect and longer service life in an electroluminescent device; the compound having the non-planar structure is used for a hole transport or hole injection layer in an organic electroluminescent device, and can reduce operating voltage and power consumption.
CN107954884A discloses a high glass transition temperature hole injection material, its preparation and application, the hole injection material is a small molecule arylamine derivative, having the structure as shown in the following
The cavityThe injection material has high glass transition temperature and decomposition temperature, high HOMO energy level, good hole mobility and good solubility, and can be used as a doping type hole injection material to obtain a stable evaporation type OLED device.
CN103319490A discloses a hole injection material for an organic electroluminescent device, and the synthesis method of the hole injection material is as follows: introducing straight-chain alkane groups into the alpha position of the traditional phthalocyanine ring structure, and substituting ions with different metals in the center of the phthalocyanine ring; the hole injection material is simple and convenient to synthesize and purify and easy to industrially prepare, the accumulation of a pi-pi conjugated system of material molecules after film formation is enhanced through the interaction between modified alkyls, the carrier migration rate of the material is improved, and partial isomers can be generated in the synthesis process of alpha-tetraalkyl substituted phthalocyanine, so that the defect that the film roughness is too large due to excessive crystallization in the traditional phthalocyanine molecule film preparation process is avoided.
However, in the prior art, most of the materials of the doped hole injection layer are lewis acid type metal complexes, halogens, grapheme and quinone compounds, the metal complexes and the halogens have the problem of poor stability during device processing, and the grapheme compounds have more steps and higher cost in synthesis.
Based on this, it is a research focus in the field to develop an organic photoelectric material with good stability, high hole injection efficiency and simple preparation process.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic photoelectric material containing C60 condensed rings, a preparation method and an application thereof, wherein the organic photoelectric material is endowed with stronger reduction potential and stability by the mutual cooperative matching of the C60 condensed rings and substituents, and can assist a hole transport layer to carry out efficient hole injection.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic photoelectric material containing a C60 condensed ring, where the organic photoelectric material containing a C60 condensed ring has a structure shown in formula I:
wherein R is1-R6Each independently selected from one of hydrogen, halogen, cyano, nitro, sulfonic acid, carboxyl, carbonyl, aldehyde, acyl, tertiary amine cation, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, alkynyl or isocyano, and R1-R6Not hydrogen at the same time.
The organic photoelectric material containing C60 condensed rings provided by the invention has a C60 condensed ring framework, so that the organic photoelectric material has good thermal stability and is beneficial to improving the film-forming property in the later-stage processing and using process; c60 condensed rings in the organic photoelectric material are cooperated with at least one substituent group with strong electron-withdrawing performance such as halogen, cyano and the like, so that a molecule is endowed with a strong reduction potential, and the organic photoelectric material can be used as a guest material to improve the hole injection performance.
When the organic photoelectric material containing the C60 condensed ring is doped into a host material of a hole injection layer as a guest material, the HOMO energy level of the host material is close to the LUMO energy level of the guest material, and the energy level difference between the HOMO energy level and the LUMO energy level of the guest material can reach less than or equal to 0.30eV, so that electrons of the HOMO energy level can be favorably transited to the LUMO energy level of the guest material, a free hole is formed, and the conductivity of an OLED device is improved; meanwhile, the organic photoelectric material containing the C60 condensed ring can bend an interface energy band as a guest material, so that holes can be injected in a tunneling mode, and the hole injection efficiency is improved. Therefore, the organic photoelectric material containing the C60 condensed ring provided by the invention is used as a guest material of a hole injection layer of an OLED device, so that the injection of charges can be effectively increased, the driving voltage of the OLED device is reduced, the overall efficiency of the device is improved, and the service life of the device is prolonged.
Preferably, the substituted or unsubstituted alkyl group is a substituted or unsubstituted C1-C10 linear or branched alkyl group, such as a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10 linear alkyl group, a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9 or C10 branched alkyl group; the C1-C10 linear or branched alkyl group illustratively includes, but is not limited to, any of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, isopropyl, tert-butyl, 2-methylbutyl, or 3-ethylhexyl.
Preferably, the halogen is F, Cl, Br or I;
preferably, the substituted or unsubstituted aryl group is a substituted or unsubstituted C6 to C30 aryl group, such as a substituted or unsubstituted C6, C7, C8, C9, C10, C12, C15, C18, C20, C22, C25, C28, C29 or C30 aryl group.
Preferably, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted C3 to C30 heteroaryl group, such as a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C18, C20, C23, C25, C27, C29 or C30 heteroaryl group, wherein the heteroatom in the heteroaryl group is N, O, S, P or the like; the C3-C30 heteroaryl group illustratively includes, but is not limited to, any one of pyridyl, pyrrolyl, indolyl, quinolinyl, furanyl, thienyl, thiazolyl, imidazolyl, or pyrazinyl.
Preferably, the substituted or unsubstituted cycloalkyl group is a substituted or unsubstituted C3 to C30 cycloalkyl group, such as a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C18, C20, C23, C25, C27, C29 or C30 cycloalkyl group.
Preferably, the substituent in the substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted alkenyl is F, Cl, Br, I, cyano, trifluoromethyl, sulfonic acid, nitro, carboxyl, carbonyl, aldehyde, tertiary amine cation, alkoxy or aryloxy.
Preferably, said R is1-R6Each independently selected from fluoro-substituted phenyl, chloro-substituted phenyl, trifluoromethyl-substituted phenyl, cyano-substituted phenyl, trifluoromethyl, trichloromethyl, methyl, ethyl, fluoro-substituted ethyl, chloro-substituted ethyl, cyano-substituted ethyl, dicyano-substituted vinyl, cyano-substituted alkoxy, cyano-substituted arylolOne of an oxy group, a fluoro-substituted alkoxy group, or a fluoro-substituted aryloxy group.
Preferably, said R is1-R6Wherein the fluorine-substituted aryl group contains at least one of F, Cl, Br, I, cyano, trifluoromethyl, trichloromethyl, fluorine-substituted ethyl, chlorine-substituted ethyl, cyano-substituted phenyl, fluorine-substituted phenyl, chlorine-substituted phenyl, trifluoromethyl-substituted phenyl, dicyano-substituted vinyl, cyano-substituted alkoxy, cyano-substituted aryloxy, fluorine-substituted alkoxy, fluorine-substituted aryloxy, sulfonic acid group, nitro group, carboxyl group, carbonyl group, aldehyde group, acyl group or tertiary amine cation.
Preferably, the organic photoelectric material containing the C60 condensed ring is any one or a combination of at least two of the following compounds 1-8:
in another aspect, the present invention provides a method for preparing an organic photoelectric material containing a C60 fused ring, the method comprising: reacting fullerene shown in a formula II with a compound shown in a formula III in the presence of an oxidative coupling agent to obtain the organic photoelectric material containing C60 condensed ring shown in the formula I, wherein the reaction formula is as follows:
wherein R is1-R6Each independently selected from one of hydrogen, halogen, cyano, nitro, sulfonic acid, carboxyl, carbonyl, aldehyde, acyl, tertiary amine cation, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, alkynyl or isocyano, and R1-R6Not hydrogen at the same time.
Preferably, the molar ratio of the fullerene of formula II to the compound of formula III is 1 (1.8-2.4), such as 1:1.85, 1:1.9, 1:1.95, 1:2, 1:2.05, 1:2.1, 1:2.15, 1:2.2, 1:2.25, 1:2.3, 1:2.35 or 1:2.4, more preferably 1:2.
Preferably, the molar ratio of the oxidative coupling agent to the fullerene of formula II is (0.5-1): 1, for example, 0.55:1, 0.6:1, 0.65:1, 0.7:1, 0.75:1, 0.8:1, 0.85:1, 0.9:1, 0.95:1 or 1:1, and more preferably 0.7: 1.
Preferably, the oxidative coupling agent is 2, 3-dichloro-5, 6-dicyan-p-benzoquinone.
Preferably, the reaction is carried out in an organic solvent;
preferably, the organic solvent is any one or a combination of at least two of toluene, benzene, chlorobenzene, bromobenzene and xylene, and is further preferably chlorobenzene;
preferably, the reaction temperature is 100-150 ℃, for example 105 ℃, 110 ℃, 115 ℃, 120 ℃, 125 ℃, 130 ℃, 135 ℃, 140 ℃, 145 ℃ or 150 ℃, and the specific values between the above values are limited to the space and the conciseness, and the invention does not exhaust the specific values included in the range, and more preferably 120 ℃.
Preferably, the reaction time is 6 to 15 hours, such as 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, 9 hours, 9.5 hours, 10 hours, 10.5 hours, 11 hours, 12 hours, 13 hours, 14 hours or 14.5 hours, and the specific values between the above values are not exhaustive, and for brevity, the invention does not list the specific values included in the range, and more preferably 10 hours.
In another aspect, the present invention provides a hole injection layer for an OLED device, the hole injection layer including a host material and a guest material, the guest material being an organic photoelectric material including a C60 fused ring as described above.
Preferably, the main body material is an arylamine compound;
preferably, the molar ratio of the host material to the guest material in the hole injection layer is (25-38: 1), for example, 25.5:1, 26:1, 26.5:1, 27:1, 28:1, 29:1, 30:1, 31:1, 32:1, 32.5:1, 33:1, 33.5:1, 34:1, 35:1, 36:1, 37:1, or 37.5:1, and more preferably 33.3: 1.
Preferably, the thickness of the hole injection layer is 30-70 nm, such as 35nm, 40nm, 45nm, 50nm, 55nm, 60nm, 65nm or 68nm, and the specific values therebetween are limited by space and for brevity, the invention is not exhaustive of the specific values included in the range, and more preferably 50 nm.
In another aspect, the present invention provides an OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, the hole injection layer being the hole injection layer for OLED devices as described above.
In another aspect, the present invention provides an electronic device comprising an OLED device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the organic photoelectric material provided by the invention is an organic compound containing C60 condensed rings and has a C60 condensed ring framework, so that the organic photoelectric material has good thermal stability and is beneficial to improving the film-forming property in the later processing and using process; c60 condensed rings in the organic photoelectric material are cooperated with substituents such as halogen, cyano and the like with strong electron-withdrawing performance, so that molecules are endowed with strong reduction potential, and the organic photoelectric material can be used as a guest material to improve the hole injection performance. The organic photoelectric material containing the C60 condensed ring is used as a hole injection layer object material of an OLED device, so that the injection of charges can be effectively increased, the driving voltage of the OLED device is reduced, the overall efficiency of the device is improved, and the service life of the device is prolonged.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The raw materials 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ), chlorobenzene, and reagents required for separation and purification used in examples 1 to 8 of the present invention were purchased from carbofuran reagents, and fullerene C60, compound 1a, compound 2a, compound 3a, compound 4a, compound 5a, compound 6a, compound 7a, and compound 8a were all commercially available chemical products.
Example 1
This example provides an organic photoelectric material compound 1 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 1 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.40g of compound 1a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 1.
Characterization data: mass spectrum MS: 887;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.85(s,3H)，2.99(m,1H)，3.32(d,1H)，3.37(t,1H)。
Example 2
This example provides an organic photoelectric material compound 2 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 2 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.82g of compound 2a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 2.
Characterization data: mass spectrum MS: 901;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.85(s,3H)，2.99(m,1H)，3.36(d,1H)，3.40(t,1H)。
Example 3
This example provides an organic photoelectric material compound 3 containing C60 fused ring, which has the following structural formula
The reaction scheme for preparing compound 3 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 1.10g of compound 3a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 3.
Characterization data: mass spectrum MS: 1039;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.99(m,1H)，3.32(d,1H)，3.37(t,1H)。
Example 4
This example provides an organic photoelectric material compound 4 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 4 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.92g of compound 4a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 4.
Characterization data: mass spectrum MS: 949;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.99(m,1H)，3.32(d,1H)，3.37(t,1H)，6.43(d,2H)，6.58(t,1H)，7.04(t,2H)。
Example 5
This example provides an organic photoelectric material compound 5 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 5 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.75g of compound 5a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 5.
Characterization data: mass spectrum MS: 861 (a);
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.85(s,3H)，2.99(m,1H)，3.35(d,1H,)，3.39(t,1H)，6.51(d,1H,)，6.52(t,1H)，6.90(t,1H)，6.95(d,1H)，7.32(s,2H)，7.46(s,1H)。
Example 6
This example provides an organic photoelectric material containing C60 condensed ringsA compound 6 having the formula
The reaction scheme for the preparation of compound 6 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.75g of compound 6a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 6.
Characterization data: mass spectrum MS: 861 (a);
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.52(d,2H)，2.85(s,3H)，2.99(m,1H)，3.30(d,1H,)，3.32(t,1H)，7.08(t,1H)，7.13(d,2H)，7.14(s,1H)，7.18(t,2H)，7.28,1H)。
Example 7
This example provides an organic photoelectric material compound 7 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 7 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.87g of compound 7a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 7.
Characterization data: mass spectrum MS: 923;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.54(d,2H)，2.99(m,1H)，3.30(d,1H,)，3.32(t,1H)，6.35(d,1H)，6.50(t,1H)，6.62(s,2H)，6.86(t,1H)，6.91(s,1H)，6.96(s,1H)，7.08(t,1H)，7.13(d,2H)，7.18(t,2H)。
Example 8
This example provides an organic photoelectric material compound 8 containing C60 fused ring, which has the following structural formula
The reaction scheme for the preparation of compound 8 is:
the preparation method comprises the following steps:
0.49g of fullerene C60(1mmol), 0.91g of compound 8a (2mmol), 0.16g of 2, 3-dichloro-5, 6-dicyan p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene were put in a reaction flask and reacted at 120 ℃ for 10 hours; obtaining a crude product through suction filtration and concentration; and then separating and purifying by using a 200-300-mesh silica gel column to obtain a product compound 8.
Characterization data: mass spectrum MS: 942 to;
nuclear magnetism1H-NMR(400 MHz，CDCl3)：1.53(d,2H)，2.99(m,1H)，3.38(d,1H,)，3.75(t,1H)，6.37(s,1H)，6.96(s,2H)，7.08(s,1H)，7.58(s,1H)，7.66(s,2H)。
Application examples 1 to 8
The preparation method of the OLED device specifically comprises the following steps:
(1) preparing an anode:
ultrasonically cleaning a transparent anode electrode Indium Tin Oxide (ITO) substrate in isopropanol for 10min, exposing the substrate to ultraviolet light for 30min, and then treating the substrate with plasma for 10 min;
(2) preparation of hole injection layer:
putting the treated ITO substrate into evaporation equipment, and firstly mixing and evaporating a layer of 50nm NPB and a mixture of the organic photoelectric materials containing C60 condensed rings, provided by the embodiments 1-8 of the invention (namely, NPB is respectively mixed with compounds 1-8, and the mol ratio of NPB to the compounds 1-8 is 33.3: 1);
(3) preparation of hole transport layer:
continuing vapor deposition, and vapor depositing NPB with the thickness of 30nm on the mixed film layer;
(4) preparation of a light-emitting layer:
then mixing and evaporating CBP and 5% Ir (ppy)3The film thickness of the mixture of (1) was 30 nm;
(5) preparation of an electron transport layer:
then evaporating 30nm Alq3 (8-hydroxyquinoline aluminum);
(6) preparing a cathode:
and evaporating 2nm LiF, and finally evaporating 150nm metal Al to form a metal cathode, thereby obtaining the OLED device.
Comparative example 1
The comparative example is different from application examples 1 to 8 in that only one layer of NPB with the thickness of 50nm is evaporated in the step (2), and other compounds are not doped.
In the application examples and the comparative examples, the corresponding structural formula of the materials is as follows:
and (3) performance testing:
the OLED devices provided in application examples 1-8 and comparative example 1 are tested for luminous efficiency, and the test method comprises the following steps: the drive voltage data was measured at a luminance of 1000nits and the half-life data was measured at a current density of 10mA/cm2Calculated under the condition.
The performance test results are shown in table 1:
TABLE 1
| Serial number | Hole injection layer material (molar ratio) | Drive voltage (V) | Half life (h) |
| Example 1 | NPB compound 1 ═ 33.3:1 | 3.9V | 7300 |
| Example 2 | NPB compound 2 ═ 33.3:1 | 3.8V | 7600 |
| Example 3 | NPB compound 3 ═ 33.3:1 | 4.0V | 7350 |
| Example 4 | NPB compound 4 ═ 33.3:1 | 3.9V | 7450 |
| Example 5 | NPB compound 5 ═ 33.3:1 | 4.1V | 7200 |
| Example 6 | NPB Compound 6 ═33.3:1 | 4.0V | 7300 |
| Example 7 | NPB compound 7 ═ 33.3:1 | 4.1V | 7300 |
| Example 8 | NPB compound 8 ═ 33.3:1 | 3.8V | 7800 |
| Comparative example 1 | NPB | 4.6V | 6000 |
The data in table 1 show that the organic photoelectric material containing the C60 condensed ring provided by the invention is highly suitable for being used as a guest material of a hole injection layer in an OLED device, and can effectively improve the hole injection efficiency; compared with the OLED device using NPB as the hole injection layer in the comparative example 1, the OLED device has lower driving voltage (below 4.2V) and longer half-life (above 7000 hours).
The applicant states that the organic photoelectric material containing C60 condensed rings, the preparation method and the application thereof are illustrated by the above examples, but the invention is not limited to the above examples, i.e. the invention is not limited to the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. An organic photoelectric material containing C60 condensed rings is characterized in that the organic photoelectric material containing C60 condensed rings has a structure shown in a formula I:
wherein R is1-R6Each independently selected from one of hydrogen, halogen, cyano, nitro, sulfonic acid, carboxyl, carbonyl, aldehyde, acyl, tertiary amine cation, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, alkynyl or isocyano, and R1-R6Not hydrogen at the same time.
2. The organic photoelectric material containing the C60 condensed ring according to claim 1, wherein the substituted or unsubstituted alkyl group is a substituted or unsubstituted C1 to C10 linear or branched alkyl group;
preferably, the halogen is F, Cl, Br or I;
preferably, the substituted or unsubstituted aryl group is a substituted or unsubstituted C6-C30 aryl group;
preferably, the substituted or unsubstituted heteroaryl is substituted or unsubstituted C3-C30 heteroaryl;
preferably, the substituted or unsubstituted cycloalkyl is substituted or unsubstituted C3 to C30 cycloalkyl;
preferably, the substituent in the substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl and substituted alkenyl is F, Cl, Br, I, cyano, trifluoromethyl, sulfonic group, nitro, carboxyl, carbonyl, aldehyde group, tertiary amine cation, alkoxy or aryloxy;
preferably, said R is1-R6Each independently selected from fluoro-substituted phenyl, chloro-substituted phenyl, trifluoromethyl-substituted phenyl, cyano-substituted phenyl, trifluoromethyl, trichloromethyl, methyl, ethyl, fluoro-substituted ethyl, chloro-substitutedOne of ethyl, cyano-substituted ethyl, dicyano-substituted vinyl, cyano-substituted alkoxy, cyano-substituted aryloxy, fluoro-substituted alkoxy or fluoro-substituted aryloxy;
preferably, said R is1-R6Wherein the fluorine-substituted aryl group contains at least one of F, Cl, Br, I, cyano, trifluoromethyl, trichloromethyl, fluorine-substituted ethyl, chlorine-substituted ethyl, cyano-substituted phenyl, fluorine-substituted phenyl, chlorine-substituted phenyl, trifluoromethyl-substituted phenyl, dicyano-substituted vinyl, cyano-substituted alkoxy, cyano-substituted aryloxy, fluorine-substituted alkoxy, fluorine-substituted aryloxy, sulfonic acid group, nitro group, carboxyl group, carbonyl group, aldehyde group, acyl group or tertiary amine cation.
3. The organic photoelectric material containing the C60 condensed ring according to claim 1 or 2, wherein the organic photoelectric material containing the C60 condensed ring is any one of the following compounds 1 to 8 or a combination of at least two of the following compounds:
4. a preparation method of the organic photoelectric material containing the C60 condensed ring according to any one of claims 1 to 3, wherein the preparation method comprises the following steps: reacting fullerene shown in a formula II with a compound shown in a formula III in the presence of an oxidative coupling agent to obtain the organic photoelectric material containing C60 condensed ring shown in the formula I, wherein the reaction formula is as follows:
wherein R is1-R6Each independently selected from hydrogen, halogen, cyano, nitroOne of a sulfonic acid group, a carboxyl group, a carbonyl group, an aldehyde group, an acyl group, a tertiary amine cation, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, an alkynyl group, or an isocyano group, and R1-R6Not hydrogen at the same time.
5. The preparation method according to claim 4, wherein the molar ratio of the fullerene shown in the formula II to the compound shown in the formula III is 1 (1.8-2.4), preferably 1: 2;
preferably, the molar ratio of the oxidative coupling agent to the fullerene shown in the formula II is (0.5-1: 1), and more preferably 0.7: 1;
preferably, the oxidative coupling agent is 2, 3-dichloro-5, 6-dicyan-p-benzoquinone.
6. The production method according to claim 4 or 5, characterized in that the reaction is carried out in an organic solvent;
preferably, the organic solvent is any one or a combination of at least two of toluene, benzene, chlorobenzene, bromobenzene and xylene, and is further preferably chlorobenzene;
preferably, the reaction temperature is 100-150 ℃, and further preferably 120 ℃;
preferably, the reaction time is 6 to 15 hours, and more preferably 10 hours.
7. A hole injection layer for an OLED device, wherein the hole injection layer comprises a host material and a guest material, and the guest material is the organic photoelectric material containing the C60 condensed ring according to any one of claims 1 to 3.
8. The hole injection layer for an OLED device according to claim 7, wherein the host material is an arylamine compound;
preferably, the molar ratio of the host material to the guest material in the hole injection layer is (25-38): 1, and more preferably 33.3: 1;
preferably, the thickness of the hole injection layer is 30 to 70nm, and more preferably 50 nm.
9. An OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, wherein the hole injection layer is the hole injection layer for the OLED device of claim 7 or 8.
10. An electronic device, characterized in that it comprises an OLED device as claimed in claim 9.
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