CN113135903A - Aromatic dibenzofuran derivative and application thereof - Google Patents
Aromatic dibenzofuran derivative and application thereof Download PDFInfo
- Publication number
- CN113135903A CN113135903A CN202010053542.0A CN202010053542A CN113135903A CN 113135903 A CN113135903 A CN 113135903A CN 202010053542 A CN202010053542 A CN 202010053542A CN 113135903 A CN113135903 A CN 113135903A
- Authority
- CN
- China
- Prior art keywords
- general formula
- group
- substituted
- unsubstituted
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 Aromatic dibenzofuran derivative Chemical class 0.000 title claims abstract description 27
- 239000010410 layer Substances 0.000 claims abstract description 59
- 230000000903 blocking effect Effects 0.000 claims abstract description 19
- 239000002346 layers by function Substances 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 10
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 10
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 10
- 150000001975 deuterium Chemical group 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- 229910052722 tritium Inorganic materials 0.000 claims description 10
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 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 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000002541 furyl group Chemical group 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
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 54
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 238000002347 injection Methods 0.000 abstract description 13
- 239000007924 injection Substances 0.000 abstract description 13
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 4
- 230000006798 recombination Effects 0.000 abstract description 4
- 238000005215 recombination Methods 0.000 abstract description 4
- 230000005855 radiation Effects 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 230000005540 biological transmission Effects 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 25
- 239000002994 raw material Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000005070 sampling Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000008204 material by function Substances 0.000 description 6
- 238000010025 steaming Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an aromatic dibenzofuran derivative and application thereof, belonging to the technical field of semiconductors, and the structure of the compound provided by the invention is shown as a general formula (I):
the invention also discloses application of the compound. The compound provided by the invention has stronger hole transmission capability, and under the appropriate HOMO energy level, the hole injection and transmission performance is improved; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; when the material is used as a light-emitting functional layer material of an OLED light-emitting device, the invention is matched withThe branched chains within the range can effectively improve the exciton utilization rate and the radiation efficiency.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to an aromatic dibenzofuran derivative and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
At present, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, but compared with actual product application requirements, the light emitting efficiency, the service life, and other performances of the OLED device need to be further improved. The research on the improvement of the performance of the OLED light emitting device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the OLED photoelectric functional material are needed to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two broad categories from the application, i.e., charge injection transport materials and light emitting materials, and further, the charge injection transport materials can be further divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light emitting materials can be further divided into main light emitting materials and doping materials.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, and as a host material of a light-emitting layer, a material having good bipolar property, appropriate HOMO/LUMO energy level, etc. is required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in the devices with different structures can also be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device, different functional film layers of the OLED device and the photoelectric characteristic requirements of the device, a more suitable OLED functional material or material combination with high performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display illumination industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and the development of organic functional materials with higher performance is very important as a material enterprise.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides an aromatic dibenzofuran derivative and its application. The compound has higher glass transition temperature, higher molecular thermal stability and proper HOMO energy level, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme of the invention is as follows:
an aromatic dibenzofuran derivative, the structure of which is shown as the general formula (1):
general formula (A)1) In, R2、R3、R4Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, an adamantyl group or a structure represented by the general formula (2)2May also be represented by the structure of the general formula (3), and R2、R3、R4At least one of them is represented by the general formula (2); r1、R7、R8Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, an adamantyl group or a structure represented by the general formula (3), and R1、R2、R7、R8At least one of them is represented by the general formula (3); r5、R6Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group or an adamantyl group;
in the general formula (2), R9、R10、R11、R12、R13、R14、R15、R16Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, C1-10Alkyl of (C)1-10Alkenyl group of (C)3-10And substituents at adjacent positions may be bonded to form a ring;
in the general formula (3), L represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
in the general formula (3), Ar1、Ar2Each independently represents a substituted or unsubstituted 6-to 60-membered aryl group, a substituted or unsubstituted 5-to 60-membered heteroaryl group containing one or more heteroatoms;
the substituent of the substituted 6-60-membered aryl and the substituted 5-60-membered heteroaryl is selected from one or more of protium atom, deuterium atom, tritium atom, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl or carbazolyl;
the heteroatom in the heteroaryl group is selected from nitrogen, oxygen or sulfur.
Preferably, the structure of the aromatic dibenzofuran derivative is shown as a general formula (4), a general formula (5) or a general formula (6):
ar is1、Ar2Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted diphenylfluorenyl group;
the substituent of the substitutable group is one or more selected from deuterium, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, cyclohexane, adamantyl, phenyl, naphthyl and biphenyl.
Preferred embodiment, R3Represented by the structure shown in the general formula (2), R1Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
Preferred embodiment, R3Represented by the structure shown in the general formula (2), R8Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
Preferred embodiment, R2Represented by the structure shown in the general formula (2), R7Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
Preferred embodiment, R2Represented by the structure shown in the general formula (2), R8Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
Preferred embodiment, R4Represented by the structure shown in the general formula (2), R8Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
Preferably, the molecular weight of the structure represented by the general formula (1) is less than or equal to 1200, and more preferably, the molecular weight is within 1000.
The preferable specific structure of the aromatic dibenzofuran derivative is as follows:
An organic electroluminescent device, at least one functional layer of the organic electroluminescent device contains the aromatic dibenzofuran derivative.
The organic electroluminescent device comprises an electron blocking layer, wherein the electron blocking layer contains the aromatic dibenzofuran derivative.
A lighting or display element comprising the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound takes a dibenzofuran structure as a center, is connected with carbazole and arylamine derivatives, and has higher hole mobility; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; can effectively improve the exciton utilization rate, reduce the voltage of the device, improve the current efficiency of the device and prolong the service life of the device. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
(2) The branched chain of the compound contains arylamine derivatives, so that the distance between molecules is increased, and the compound has higher Tg temperature and smaller intermolecular force. The compound has lower vapor deposition temperature due to smaller intermolecular force, thereby not only ensuring that the vapor deposition material is not decomposed in mass production for a long time, but also reducing the deformation influence of the heat radiation of the vapor deposition temperature on the Mask, and widening the industrial processing window of the material.
(3) When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved, and the compound has good application effect and industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a substrate layer, 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 an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a CPL layer.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
Preparation of intermediates I-1 and II-1:
adding 0.01mol of raw material A-1, 0.01mol of raw material B-1 and 150ml of toluene into a 250ml three-neck bottle under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate I-1;
adding 0.01mol of intermediate I-1 and 0.01mol of raw material C into a 250ml three-mouth bottle under the protection of nitrogen150ml of toluene are mixed with stirring and then 5X 10 are added-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain an intermediate S-1;
adding 0.01mol of intermediate S-1, 0.0075mol of bis (pinacolato) diboron and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-4mol Pd(dppf)Cl20.025mol of potassium acetate, heating to 105 ℃, refluxing and reacting for 24 hours, sampling a point plate, showing that no bromide is left, and completely reacting; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain an intermediate II-1;
the preparation methods of other intermediates I and II are similar to the preparation methods of the intermediate I-1 and the intermediate II-1, and the specific structures of the raw material A, the raw material B, the raw material C, the intermediate I and the intermediate II used in the invention are shown in Table 1.
TABLE 1
Preparation of intermediate III-1:
adding 0.01mol of raw material D-1 and 0.012mol of raw material E-1 into a 250ml three-neck flask under the protection of nitrogen, dissolving with mixed solvent (90ml of toluene and 45ml of ethanol), and adding 1X 10-4mol Pd(PPh3)4，0.03molK2CO3Heating and refluxing the aqueous solution (2M) for 15 hours, sampling a sample, and confirming the completion of the reaction; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain an intermediate M-1;
adding 0.01mol of intermediate M-1, 150ml of NMP into a 250ml three-mouth bottle under the protection of nitrogen, stirring and dissolving, and then adding 0.025mol of K2CO3Carrying out reflux reaction for 24 hours, sampling a sample, and completely reacting; naturally cooling to room temperature, filtering, carrying out rotary evaporation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate III-1;
the preparation method of other intermediate III is similar to that of intermediate III-1, and the specific structures of the raw material D, the raw material E and the intermediate III used in the invention are shown in Table 2.
TABLE 2
EXAMPLE 1 preparation of Compound 56
(1) In a 250ml three-necked flask, 0.012mol of intermediate II-1 and 0.01mol of intermediate III-1 were added under nitrogen protection, dissolved in a mixed solvent (90ml of toluene and 45ml of ethanol), and then 1X 10 was added-4mol Pd(PPh3)4，0.03molK2CO3An aqueous solution (2M),heating and refluxing for reaction for 15 hours, sampling a point plate, and displaying that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate T-1;
(2) adding 0.01mol of raw material F-1, 0.01mol of intermediate T-1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, sampling a sample point plate, and confirming the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the compound 56.
EXAMPLE 3 preparation of Compound 75
(1) Adding 0.01mol of intermediate I-3, 0.01mol of intermediate III-2 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate T-3;
(2) adding 0.01mol of raw material F-1, 0.01mol of intermediate T-3 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, sampling a sample point plate, and confirming the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain a compound 75.
For structural analysis of the compounds prepared in examples, the molecular weight was measured using MS and prepared by dissolving in deuterated chloroform solventAnd measured by a 500MHz NMR instrument1The results of H-NMR are shown in tables 3 and 4.
The preparation of the other compounds was similar to that of the compound of example 1 or 3, and the specific structures of intermediate I, starting material II and product used in this example are shown in table 3, and table 4 shows nuclear magnetic data of the specific structures shown.
TABLE 3
TABLE 4
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
The compound is used in a light-emitting device and mainly used as an electron blocking layer material. The compounds prepared in the above examples of the present invention were tested for thermal performance, T1 energy level, HOMO energy level and hole mobility, respectively, and the test results are shown in table 5:
TABLE 5
Note: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg is tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901); and (3) testing hole mobility, namely preparing the material into a single-charge device and measuring by using an SCLC (liquid crystal display cell) method.
The data in the table show that the compound has high glass transition temperature, can improve the phase stability of the material film, and further improves the service life of the device; the compound contains an electron donor and an electron acceptor, so that electrons and holes of an OLED device applying the compound reach a balanced state, the recombination rate of the electrons and the holes is ensured, the efficiency and the service life of the OLED device are improved, and the material has a high triplet state energy level, can block energy loss of a light-emitting layer, and improves the light-emitting efficiency of the device. Meanwhile, the material has a proper HOMO energy level, so that the problem of carrier injection can be solved, and the voltage of a device can be reduced; under a shallow LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, improves the recombination efficiency of excitons in a light-emitting layer, reduces energy loss, and enables the energy of a main material of the light-emitting layer to be fully transferred to a doped material, thereby improving the luminous efficiency of the material after being applied to a device; therefore, after the organic material is applied to the electron blocking layer of the OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The application effect of the synthesized OLED material in the device is explained in detail through device examples 1-32 and device comparative examples 1-4. Compared with the devices of comparative examples 1 to 4, the devices of examples 2 to 32 of the invention have the same manufacturing process, and the same substrate material and electrode material are adopted, so that the film thickness of the electrode material is kept consistent, except that the material of the electron barrier layer in the device is replaced.
Device example 1:
the preparation process comprises the following steps:
as shown in fig. 1, the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer 1. HT-1 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. Next, HT-1 was evaporated to a thickness of 130nm as a hole transport layer 4. The compound 56 of the invention was subsequently evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that BH-1 used by the OLED light emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light emitting layer is 20 nm. After the light-emitting layer 6, ET-1 and Liq are continuously evaporated, wherein the mass ratio of ET-1 to Liq is 1: 1. The vacuum-deposited film thickness of this material was 35nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a Yb layer having a film thickness of 1nm, which is an electron-injecting layer 8, was formed by a vacuum evaporation apparatus. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1:9, and is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10.
Device examples 2 to 32:
the preparation method and the device structure of the device embodiments 2-32 are the same as those of the device embodiment 1, except that: the compounds 62, 75, 82, 97, 118, 122, 123, 124, 149, 157, 180, 182, 198, 201, 205, 209, 225, 239, 240, 252, 267, 291, 312, 338, 372, 378, 385, 386, 406, 414, 430 of the present application are used as electron blocking organic materials for organic electroluminescent devices.
Device comparative examples 1 to 4:
the devices of comparative examples 1 to 4 were prepared in the same manner as in device example 1, except that: EB-1, EB-2, EB-3, and EB-4 were used as electron blocking layer organic materials of organic electroluminescent devices.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, the light emission spectrum, and the lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 5; the results of the performance test of each device are shown in table 6.
TABLE 5
TABLE 6
Note: voltage, current efficiency and color coordinates were measured using an IVL (Current-Voltage-Brightness) test System (Fushda scientific instruments, Suzhou) at a current density of 10mA/cm2(ii) a The life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95% at a particular luminance (blue: 1000 nits); index is current efficiency/CIEy and is only applied to blue devices, and the efficiency of blue devices is generally not referenced to current efficiency, but to Index (an industry standard).
From the device data results, it can be seen that compared with the comparative device example, the organic light emitting device of the present invention has a greater increase in efficiency and lifetime compared with the OLED device of the known material, and the voltage is reduced, which means that the organic light emitting device of the present invention has lower power consumption.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An aromatic dibenzofuran derivative is characterized in that the structure of the derivative is shown as a general formula (1):
in the general formula (1), R2、R3、R4Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, an adamantyl group, a phenyl group or a structure represented by the general formula (2)2May also be represented by the structure of the general formula (3), and R2、R3、R4At least one of them is represented by the general formula (2); r1、R7、R8Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, an adamantyl group, a phenyl group or a structure represented by the general formula (3), and R1、R2、R7、R8At least one of them is represented by the general formula (3); r5、R6Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group or an adamantyl group;
in the general formula (2), R9、R10、R11、R12、R13、R14、R15、R16Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, C1-10Alkyl of (C)1-10Alkenyl group of (C)3-10And substituents at adjacent positions may be bonded to form a ring;
in the general formula (3), L represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
in the general formula (3), Ar1、Ar2Each independently represents a substituted or unsubstituted 6-to 60-membered aryl group, a substituted or unsubstituted 5-to 60-membered heteroaryl group containing one or more heteroatoms;
the substituent of the substituted 6-60-membered aryl and the substituted 5-60-membered heteroaryl is selected from one or more of protium atom, deuterium atom, tritium atom, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl or carbazolyl;
the heteroatom in the heteroaryl group is selected from nitrogen, oxygen or sulfur.
2. The aromatic dibenzofuran derivative of claim 1, wherein the structure is represented by general formula (4), general formula (5) or general formula (6):
3. the aromatic dibenzofuran derivative of claim 1, wherein Ar is Ar1、Ar2Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group;
the substituent of the substitutable group is one or more selected from deuterium, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, cyclohexane, adamantyl, phenyl, naphthyl and biphenyl.
4. The aromatic dibenzofuran derivative of claim 1, wherein R is3Represented by the structure shown in the general formula (2), R1Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
5. The aromatic dibenzofuran derivative of claim 1, wherein R is3Represented by the structure shown in the general formula (2), R8Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
6. The aromatic dibenzofuran derivative of claim 1, wherein R is4Represented by the structure shown in the general formula (2), R8Is represented by the general formula (3), and L is a single bond, phenylene or biphenylene.
7. The aromatic dibenzofuran derivative of claim 1, wherein the derivative has the following specific structure:
8. An organic electroluminescent element, characterized in that at least one functional layer of the organic electroluminescent element comprises the aromatic dibenzofuran derivative according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, comprising an electron blocking layer, wherein the electron blocking layer contains the aromatic dibenzofuran derivative according to any one of claims 1 to 7.
10. A lighting or display element comprising the organic electroluminescent device according to claim 8 or 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010053542.0A CN113135903A (en) | 2020-01-17 | 2020-01-17 | Aromatic dibenzofuran derivative and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010053542.0A CN113135903A (en) | 2020-01-17 | 2020-01-17 | Aromatic dibenzofuran derivative and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113135903A true CN113135903A (en) | 2021-07-20 |
Family
ID=76808305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010053542.0A Pending CN113135903A (en) | 2020-01-17 | 2020-01-17 | Aromatic dibenzofuran derivative and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113135903A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113896720A (en) * | 2021-09-27 | 2022-01-07 | 陕西莱特迈思光电材料有限公司 | Organic compound, electronic element, and electronic device |
| WO2023234603A1 (en) * | 2022-05-30 | 2023-12-07 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
| WO2023237073A1 (en) * | 2022-06-10 | 2023-12-14 | 浙江光昊光电科技有限公司 | Aromatic amine organic compound and use thereof in organic electronic device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014129764A1 (en) * | 2013-02-19 | 2014-08-28 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| CN110277500A (en) * | 2018-03-13 | 2019-09-24 | 三星显示有限公司 | Organic light emitting apparatus |
| CN114730844A (en) * | 2019-12-27 | 2022-07-08 | Lt素材株式会社 | Organic light emitting element and composition of organic material layer for organic light emitting element |
-
2020
- 2020-01-17 CN CN202010053542.0A patent/CN113135903A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014129764A1 (en) * | 2013-02-19 | 2014-08-28 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| CN110277500A (en) * | 2018-03-13 | 2019-09-24 | 三星显示有限公司 | Organic light emitting apparatus |
| CN114730844A (en) * | 2019-12-27 | 2022-07-08 | Lt素材株式会社 | Organic light emitting element and composition of organic material layer for organic light emitting element |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113896720A (en) * | 2021-09-27 | 2022-01-07 | 陕西莱特迈思光电材料有限公司 | Organic compound, electronic element, and electronic device |
| CN113896720B (en) * | 2021-09-27 | 2023-06-09 | 陕西莱特迈思光电材料有限公司 | Organic compound, electronic component, and electronic device |
| WO2023234603A1 (en) * | 2022-05-30 | 2023-12-07 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
| WO2023237073A1 (en) * | 2022-06-10 | 2023-12-14 | 浙江光昊光电科技有限公司 | Aromatic amine organic compound and use thereof in organic electronic device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113004259B (en) | Compound with anthrone skeleton as core and application thereof | |
| CN110964021A (en) | Compound with fluorene as core, preparation method and application thereof | |
| CN111662258A (en) | Organic compound containing pyrene and application thereof in OLED | |
| CN111662259A (en) | Organic compound containing pyrene and application thereof in organic electroluminescent device | |
| CN111662187A (en) | Amino-containing organic compound and application thereof | |
| CN110835318B (en) | Organic compound with azafluorene as core and preparation method and application thereof | |
| CN113135903A (en) | Aromatic dibenzofuran derivative and application thereof | |
| CN110577488A (en) | Compound with carbazole as core and application thereof in organic electroluminescent device | |
| CN110835304A (en) | Compound with spirofluorene structure as core, preparation method and application thereof | |
| CN110642732B (en) | Organic compound containing spirofluorene anthrone structure and application thereof | |
| CN110577523B (en) | Compound containing triarylamine structure and organic electroluminescent device prepared from compound | |
| CN112479978A (en) | Organic compound with carbazole derivative as core and application thereof | |
| CN110963904A (en) | Compound with ketone and fluorene as cores, preparation method and application thereof | |
| CN110835305A (en) | Organic compound containing dibenzosuberene, preparation method and application thereof | |
| CN111362955A (en) | Organic compound and application thereof to OLED device | |
| CN111233844A (en) | Organic compound with carbazole as core, preparation method and application thereof | |
| CN114057660B (en) | Compound containing bis-triazine structure and application thereof | |
| CN113461592B (en) | Biphenyl carbazole bis-triarylamine organic compound and application thereof | |
| CN112552225B (en) | Triarylamine organic compound with carbazole as core and application thereof | |
| CN113004298B (en) | Anthracene ketone five-membered ring organic compound and application thereof | |
| CN111233675B (en) | Organic compound containing benzoanthracene and application thereof | |
| CN112479905B (en) | Organic compound containing benzoanthracene fluorene and diarylamine and application thereof in organic electroluminescent device | |
| CN113461593A (en) | Biphenylamine derivative and application thereof | |
| CN110343049B (en) | Organic compound with spiro dibenzosuberene fluorene as skeleton and application thereof | |
| CN114276253A (en) | Triarylamine organic compound containing pyrene structure and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Country or region after: China Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214000 Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province Applicant before: Jiangsu March Technology Co.,Ltd. Country or region before: China |
|
| CB02 | Change of applicant information |