CN114524814B - Organic compound, organic light-emitting display panel and application thereof - Google Patents
Organic compound, organic light-emitting display panel and application thereof Download PDFInfo
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- CN114524814B CN114524814B CN202210179396.5A CN202210179396A CN114524814B CN 114524814 B CN114524814 B CN 114524814B CN 202210179396 A CN202210179396 A CN 202210179396A CN 114524814 B CN114524814 B CN 114524814B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000010410 layer Substances 0.000 claims description 33
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052722 tritium Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 30
- 238000000926 separation method Methods 0.000 abstract description 9
- 230000003111 delayed effect Effects 0.000 abstract description 7
- 230000001052 transient effect Effects 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000008569 process Effects 0.000 description 13
- -1 spirobifluorenyl Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 2
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 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 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
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- 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
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- 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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- 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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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- Optics & Photonics (AREA)
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Abstract
The invention provides an organic compound, an organic light-emitting display panel and application thereof. The organic compound provided by the invention has a structure shown in a formula I; in the organic compound provided by the invention, the separation of the charge donor and the charge acceptor of the molecule realizes smaller delta Est, so that the molecule has TADF property; the organic compound provided by the invention is a blue heat-activated delayed luminescent material, has a strong rigid structure, is not easy to twist and rotate, can rapidly generate intersystem crossing and inverse intersystem crossing in a molecule, and has a reduced transient fluorescence life, so that higher efficiency is shown; the organic compound provided by the invention is used as a main material of the light-emitting layer, so that the device has higher efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound, an organic light-emitting display panel and application thereof.
Background
Organic light-emitting diodes (OLEDs) have been widely focused in current academia and industry due to their wide application prospects in fields such as full-color flat panel displays and solid illumination.
Organic electroluminescence can be divided into fluorescence and phosphorescence from the light emitting mechanism, the phosphorescence material can utilize the spin coupling energy of heavy atomic effect and simultaneously utilize singlet state and triplet state excitons to emit light, so that the quantum efficiency in the device can reach 100% theoretically, and the material is the material with the highest organic electroluminescence efficiency at present, but the cost of the phosphorescence material is higher due to the use of noble metals such as iridium, platinum and the like, and huge economic pressure is brought to flat panel display enterprises.
The fluorescent material has low cost because noble metal coordination is not needed, and the chemical property is more stable, so the fluorescent material has more value in the aspect of practical application. However, since triplet excitons of conventional fluorescent materials can release energy back to an excited state only in a non-radiative manner at room temperature, most of the energy of the excited state molecules is lost in a non-radiative manner. Therefore, how to improve the luminous quantum efficiency of the fluorescent material, breaks through the limit that the theoretical internal quantum efficiency is only 25 percent, and has great significance for the fluorescent material.
In recent years, with the progress of technology, in order to overcome the defects of high synthesis cost and short service life of phosphorescent materials and the limit of only 25% of internal quantum efficiency of fluorescent materials, a thermally activated delayed fluorescence (ThermallyActivated Delayed Fluorescence, TADF for short) material is considered as a 'third generation luminescent material' following the traditional fluorescent materials and phosphorescent materials, and is a pure organic molecular compound capable of realizing 100% of internal quantum yield. Meanwhile, the material has high luminous efficiency, stable thermodynamic and electrochemical properties, does not need expensive noble metal, can reduce the production cost of devices, and has wide application prospect in the field of OLEDs.
Organic electroluminescent devices that exhibit luminescence via the TADF mechanism still need further improvements in terms of efficiency, voltage, lifetime and/or roll-off behavior. In general, a method for obtaining a relatively small delta Est by using a TADF material is to separate LUMO from HOMO, the conjugation of molecules is broken, C-C bonds or C-N bonds connected by a doner segment and an acid receptor segment in the molecules are easy to break, the service life of triplet excitons is relatively long, and the molecules are in an excited state for a long time, so that the service life is seriously reduced.
Therefore, how to provide an organic compound that can achieve smaller Δest through separation of the charge donor and the charge acceptor of the molecule is a current problem to be solved.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide an organic compound, an organic light-emitting display panel and application thereof. The organic compound provided by the invention is a blue thermal activation delay luminescent material, and smaller delta Est is realized through separation of a charge donor and a charge acceptor of molecules. In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic compound having a structure according to formula I:
wherein L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene, substituted or unsubstituted C1-C60 alkyl, and substituted or unsubstituted C3-C60 cycloalkyl;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from any of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C1-C60 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy; alternatively, R 1 、R 2 、R 3 、R 4 、R 5 Each independently forming a saturated or unsaturated carbocyclic or heterocyclic ring with an adjacent benzene ring by covalent bonds;
x is selected from O, S, NR N1 、CR C1 R C2 Any one of them;
R N1 、R C1 、R C2 each independently selected from any of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C20 arylsilyl.
In the organic compound provided by the invention, the separation of the charge donor and the charge acceptor of the molecule realizes smaller delta Est, so that the molecule has TADF property; the organic compound provided by the invention is a blue heat-activated delayed luminescent material, has a strong rigid structure, is not easy to twist and rotate, can rapidly generate intersystem crossing and inverse intersystem crossing in a molecule, and has a reduced transient fluorescence life, so that higher efficiency is shown; the organic compound provided by the invention is used as a main material of the light-emitting layer, so that the device has higher efficiency and longer service life.
In the present invention, C6-C60 may each independently be C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, C3-C60 may each independently be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, C1-C60 may each independently be C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, each of C1-C30 may be independently C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.
In the present invention, each of C2 to C20 may be, independently, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.
In the present invention, each of C6-C30 may be, independently, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.
In the present invention, each of C3 to C30 may be, independently, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.
In the present invention, C5-C30 may each independently be C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.
In the present invention, each of C6 to C20 may be, independently, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, or the like.
In a second aspect, the present invention provides an organic light emitting display panel comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a light emitting layer and an electron transporting layer, at least one of the light emitting layer and the electron transporting layer comprising the organic compound of the first aspect.
In the present invention, the organic layer may be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a vacuum evaporation process, or a roll-to-roll process.
The organic light-emitting display panel provided by the invention has better performance, especially in the aspects of efficiency, voltage, service life and roll-off behavior.
In a third aspect, the present invention provides an organic light emitting display device comprising the organic light emitting display panel of the second aspect.
In the present invention, the organic light emitting display device includes any one of an organic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, or an illumination element.
Compared with the prior art, the invention has the following beneficial effects:
(1) In the organic compound provided by the invention, the separation of the charge donor and the charge acceptor of the molecule realizes smaller delta Est, so that the molecule has TADF property;
(2) The organic compound provided by the invention is a blue heat-activated delayed luminescent material, has a strong rigid structure, is not easy to twist and rotate, can rapidly generate intersystem crossing and inverse intersystem crossing in a molecule, and has a reduced transient fluorescence life, so that higher efficiency is shown;
(2) The organic compound provided by the invention is used as a main material of the light-emitting layer, so that the device has higher efficiency and longer service life.
Drawings
FIG. 1 is a schematic diagram of an OLED device according to the present invention;
wherein 110 is a glass substrate, 120 is an anode, 130 is a hole injection layer, 140 is a hole transport layer, 150 is a light emitting layer, 160 is an electron transport layer, and 170 is a cathode.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
It is an object of the present invention to provide an organic compound having a structure represented by the following formula I:
wherein L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene, substituted or unsubstituted C1-C60 alkyl, and substituted or unsubstituted C3-C60 cycloalkyl;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from any of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C1-C60 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy; alternatively, R 1 、R 2 、R 3 、R 4 、R 5 Each independently forming a saturated or unsaturated carbocyclic or heterocyclic ring with an adjacent benzene ring by covalent bonds;
x is selected from O, S, NR N1 、CR C1 R C2 Any one of them;
R N1 、R C1 、R C2 each independently selected from any of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C20 arylsilyl.
In the organic compound provided by the invention, the separation of the charge donor and the charge acceptor of the molecule realizes smaller delta Est, so that the molecule has TADF property; the organic compound provided by the invention is a blue heat-activated delayed luminescent material, has a strong rigid structure, is not easy to twist and rotate, can rapidly generate intersystem crossing and inverse intersystem crossing in a molecule, and has a reduced transient fluorescence life, so that higher efficiency is shown; the organic compound provided by the invention is used as a main material of the light-emitting layer, so that the device has higher efficiency and longer service life.
In the present invention, C6-C60 may each independently be C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, C3-C60 may each independently be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, C1-C60 may each independently be C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.
In the present invention, each of C1-C30 may be independently C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.
In the present invention, each of C2 to C20 may be, independently, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.
In the present invention, each of C6-C30 may be, independently, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.
In the present invention, each of C3 to C30 may be, independently, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.
In the present invention, C5-C30 may each independently be C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.
In the present invention, each of C6 to C20 may be, independently, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, or the like.
In the present invention, substituted arylene, substituted heteroarylene, substituted aryl, substituted heteroaryl, substituted alkyl, substituted alkoxy, substituted alkylthio, substituted silyl, substituted cycloalkyl, substituted alkenyl, substituted alkynyl, substituted aryloxy, substituted heteroalkyl, substituted arylsilane substituents each independently selected from deuterium, tritium, halogen, C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), straight or branched alkyl, C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), alkoxy, C1-C10 (e.g., C1, C2, C3, C4, C5, etc.), straight or branched alkyl, C1-C10 (e.g., C1, C2, C3, C4, C5, C10, C C6, C7, C8, C9, C10, etc.), an alkylthio group, a C1-C10 silyl group (which may be, for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), a C6-C20 (which may be, for example, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.), an aryl group, a C3-C20 (which may be, for example, any of C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.), a heteroaryl group or a C6-C18 (which may be, for example, any of C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C17, C18, etc.), an aryl group, etc.
In the present invention, the aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, or spirobifluorenyl.
In the present invention, the heteroaryl group is selected from any one of carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, dibenzothiophenyl, dibenzofuranyl, naphthazidazolyl, naphthazazolyl, naphthazolyl, phenanthroimidazolyl, phenanthroozolyl, phenanthrothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolopyrazinyl, indenopyrazinyl or indenopyrimidinyl.
In one embodiment, L is selected from a single bond, unsubstituted or R y1 Substituted phenylene, unsubstituted or R y1 Substituted biphenylene, unsubstituted or R y1 Substituted naphthylene, unsubstituted or R y1 Substituted C3-C12 (e.g., can be any of C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, etc.) nitrogen-containing heteroarylene;
R y1 selected from deuterium, tritium, halogen, cyano, C1-C6 (which may be C1, C2, C3, C4, C5, C6, etc.), straight or branched chain alkyl, C1-C6 may be, for example, C1, C2, C3, C4, C5, C6, etc.), alkoxy, C1-C6 (which may be, for example, C1, C2, C3, C4, C5, C6, etc.), alkylthio, C6-C12 (which may be, for example, C6, C7, C8, C9, C10, C11, C12, etc.), aryl, or C3-C12 (which may be, for example, any of C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, etc.), heteroaryl.
In the invention, L is selected from the groups above, and the synthesis method is simpler.
In one embodiment, L is selected from any of a single bond, unsubstituted or C1-C6 (e.g., C1, C2, C3, C4, C5, C6, etc.) alkyl-substituted phenylene, unsubstituted or C1-C6 (e.g., C1, C2, C3, C4, C5, C6, etc.) alkyl-substituted naphthylene, unsubstituted or C1-C6 (e.g., C1, C2, C3, C4, C5, C6, etc.) alkyl-substituted biphenylene.
In the invention, L is selected from the groups, the compound has a strong rigid structure, the molecule is not easy to twist and rotate, intersystem crossing and intersystem crossing can be quickly generated in the molecule, and the transient fluorescence lifetime is reduced, so that higher efficiency is shown.
In one embodiment, the R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, tritium, halogen, cyano, unsubstituted or R y2 Substituted C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), straight or branched alkyl, unsubstituted or R y2 Substituted C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) alkoxy, unsubstituted or R y2 Substituted C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), unsubstituted or R y2 Substituted C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), unsubstituted or R y2 Substituted C6-C20 (e.g., C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) aryl, unsubstituted or R y2 Any of the substituted C3-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) heteroaryl groups; alternatively, R 1 、R 2 、R 3 、R 4 、R 5 Each independently forming a saturated or unsaturated carbocyclic or heterocyclic ring with an adjacent benzene ring by covalent bonds;
R y2 selected from deuterium, tritium, halogen, cyano, C1-C6 (which may be C1, C2, C3, C4, C5, C6, etc.), straight or branched alkyl, C1-C6 (which may be C1, C2, C3, C4, C5, C6, etc.), alkoxy, C1-C6 (which may be C1, C2, C3, C4, C5, C6, etc.), alkylthio, C6-C12 (which may be C6, C7, C8, C9, C10, C11, C12, etc.), aryl or C3-C12 heteroarylAny one of the following.
In the present invention, R 1 、R 2 、R 3 、R 4 、R 5 When selected from the above groups, the separation of the charge donor and charge acceptor of the molecule achieves a smaller deltaest, giving the molecule its TADF properties.
In one embodiment, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of hydrogen, deuterium, tritium, C1-C10 (e.g., can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), unsubstituted or C1-C6 (e.g., can be C1, C2, C3, C4, C5, C6, etc.) alkyl-substituted C6-C20 (e.g., can be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.), unsubstituted or C1-C6 (e.g., can be C1, C2, C3, C4, C5, C6, etc.) alkyl-substituted C3-C20 (e.g., can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C16, C19, C20, etc.), heteroaryl, etc.; alternatively, R 1 、R 2 、R 3 、R 4 、R 5 Each independently forming a saturated or unsaturated carbocyclic or heterocyclic ring with an adjacent benzene ring by covalent bonds.
In the present invention, R 1 、R 2 、R 3 、R 4 、R 5 Selected from the above groups, the synthesis method is simpler.
In one embodiment, X is selected from O, S, NR N2 、CR C3 R C4 Any one of them;
R N2 、R C3 、R C4 each independently selected from any of hydrogen, C1-C10 (e.g., may be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), straight or branched chain alkyl, substituted or unsubstituted C1-C30 (e.g., may be C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.) heteroalkyl, substituted or unsubstituted C6-C30 (e.g., may be C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.) aryl.
In the present invention, when X is selected from the above groups, the resulting device has higher efficiency and longer lifetime.
In one embodiment, the organic compound includes any one of the following M1-M51:
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in the present invention, the separation of the charge donor and acceptor of the molecule in the compounds represented by M1-M51 achieves a smaller ΔEst, giving the molecule its TADF properties.
It is a second object of the present invention to provide an organic light emitting display panel including an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer including a light emitting layer and an electron transporting layer, at least one of the light emitting layer and the electron transporting layer including an organic compound of one of the objects.
In the present invention, the organic layer may be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a vacuum evaporation process, or a roll-to-roll process.
The organic light-emitting display panel provided by the invention has better performance, especially in the aspects of efficiency, voltage, service life and roll-off behavior.
Another object of the present invention is to provide an organic light emitting display device including the second organic light emitting display panel.
In the present invention, the organic light emitting display device includes any one of an organic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, or an illumination element.
Example 1
This example provides an organic compound M3 having the following structural formula:
the preparation method of the organic compound M3 comprises the following steps:
(1) Preparation of Compound c-1
Dissolving a compound a-1 (11.8 g,0.1 mol) and a compound b-1 (34.9 g,0.1 mol) in 500mL of toluene solution, adding potassium carbonate (13.8 g,0.1 mol), 1g of tetraphenylphosphine palladium and 50mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8 hours, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound c-1 (38 g,0.0884 mol) with a yield of 88.4%;
MS[M+H] + calcd for C 28 H 23 N 4 O:431.5,found:.MS＝431.5。
(2) Preparation of Compound d-1
Compound c-1 (21.5 g,50 mmol) was dissolved in 200mL of concentrated H 3 PO 4 Stirring the solution for 12 hours at room temperature; after the reaction was completed, the mixture was poured into water, and the compound d-1 was precipitated, filtered, and purified by ethyl acetate/petroleum ether (V Acetic acid ethyl ester :V Petroleum ether Mixed solution recrystallisation to give intermediate d-1 (16 g,38.83 mmol) in 77.7% yield;
MS[M+H] + calcd for C 28 H 21 N 4 :413.5,found:MS＝413.5。
(3) Preparation of Compound f-3
Dissolving compound d-1 (4.1 g,10 mmol) in 100mL of carbon tetrachloride solution, adding potassium carbonate (1.4 g,10 mol), cooling to 0 ℃, slowly adding NBS (e-1) (1.8 g,10 mmol), preserving heat for 2h, washing the solution with water, drying and concentrating; recrystallization gave compound f-3 (3.8 g,7.7 mmol), yield 77%;
MS[M+H] + calcd for C 28 H 20 BrN 4 :492.4,found:MS＝492.4。
(4) Preparation of Compound M3
Dissolving a compound f-3 (2.5 g,5 mmol) and a compound g-1 (1.1 g,6 mmol) in 50mL of toluene solution, adding potassium carbonate (0.7 g,5 mmol), 0.1g of tetraphenylphosphine and 10mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8h, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound M3 (2.5 g,4.2 mmol) with a yield of 84%;
MS[M+H] + calcd for C 40 H 28 N 5 O:594.7,found:MS＝594.7。
example 2
This example provides an organic compound M4 having the following structural formula:
the preparation method of the organic compound M4 comprises the following steps:
(1) Preparation of Compound c-3
Dissolving a compound a-1 (11.8 g,0.1 mol) and a compound b-3 (37.7 g,0.1 mol) in 500mL of toluene solution, adding potassium carbonate (13.8 g,0.1 mol), 1g of tetraphenylphosphine palladium and 50mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8 hours, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound c-3 (32.4 g,0.075 mol) with a yield of 70.5%;
MS[M+H] + calcd for C 30 H 27 N 4 O:459.6,found:.MS＝459.6。
(2) Preparation of Compound d-3
Compound c-3 (22.9 g,50 mmol) was dissolved in 200mL of concentrated H 3 PO 4 Stirring the solution for 12 hours at room temperature; after the reaction was completed, the mixture was poured into water, and the compound d-3 was precipitated, filtered, and purified by ethyl acetate/petroleum ether (V Acetic acid ethyl ester :V Petroleum ether =1:5) to give intermediate d-3 (17.6 g,39.8 mmol) in 79.6% yield;
MS[M+H] + calcd for C 30 H 25 N 4 :441.6,found:MS＝441.6。
(3) Preparation of Compound f-4
Dissolving compound d-3 (4.4 g,10 mmol) in 100mL of carbon tetrachloride solution, adding potassium carbonate (1.4 g,10 mol), cooling to 0 ℃, slowly adding NBS (e-1) (1.8 g,10 mmol), preserving heat for 2h, washing the solution with water, drying and concentrating; recrystallization gave compound f-4 (3.7 g,7.1 mmol) in 71% yield;
MS[M+H] + calcd for C 30 H 24 BrN 4 :520.5,found:MS＝520.5。
(4) Preparation of Compound M4
Dissolving a compound f-4 (2.6 g,5 mmol) and a compound g-1 (1.1 g,6 mmol) in 50mL of toluene solution, adding potassium carbonate (0.7 g,5 mmol), 0.1g of tetraphenylphosphine and 10mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8h, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound M4 (2.2 g,3.5 mmol) with a yield of 66.7%;
MS[M+H] + calcd for C 42 H 32 N 5 O:622.8,found:MS＝622.8。
example 3
This example provides an organic compound M5 having the following structural formula:
the preparation method of the organic compound M5 comprises the following steps:
(1) Preparation of Compound c-4
Dissolving a compound a-1 (11.8 g,0.1 mol) and a compound b-4 (37.7 g,0.1 mol) in 500mL of toluene solution, adding potassium carbonate (13.8 g,0.1 mol), 1g of tetraphenylphosphine palladium and 50mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8 hours, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound c-4 (22.9 g,0.05 mol) with a yield of 50%;
MS[M+H] + calcd for C 30 H 27 N 4 O:459.6,found:.MS＝459.6。
(2) Preparation of Compound d-4
Compound c-4 (22.9 g,50 mmol) was dissolved in 200mL of concentrated H 3 PO 4 Stirring the solution for 12 hours at room temperature; after the reaction was completed, the mixture was poured into water, and the compound d-4 was precipitated, filtered, and purified by ethyl acetate/petroleum ether (V Acetic acid ethyl ester :V Petroleum ether Mixed solution recrystallisation of =1:5) to give intermediate d-4 (13.5 g,30.6 mmol) in 61.1% yield;
MS[M+H] + calcd for C 30 H 25 N 4 :441.6,found:MS＝441.6。
(3) Preparation of Compound f-5
Dissolving compound d-4 (4.4 g,10 mmol) in 100mL of carbon tetrachloride solution, adding potassium carbonate (1.4 g,10 mol), cooling to 0 ℃, slowly adding NBS (e-1) (1.8 g,10 mmol), preserving heat for 2h, washing the solution with water, drying and concentrating; recrystallization gave compound f-5 (4 g,7.7 mmol), yield 77%;
MS[M+H] + calcd for C 30 H 24 BrN 4 :520.5,found:MS＝520.5。
(4) Preparation of Compound M5
Dissolving a compound f-5 (2.6 g,5 mmol) and a compound g-1 (1.1 g,6 mmol) in 50mL of toluene solution, adding potassium carbonate (0.7 g,5 mmol), 0.1g of tetraphenylphosphine and 10mL of tetraphenylphosphine solution, replacing with nitrogen, then heating to 100 ℃, stirring for 8h, cooling to room temperature after the reaction is completed, pouring into water, filtering, and recrystallizing to obtain a compound M5 (1.5 g,2.4 mmol) with a yield of 48%;
MS[M+H] + calcd for C 42 H 32 N 5 O:622.8,found:MS＝622.8。
application example 1
The present application example provides an OLED device, as shown in fig. 1, the organic light emitting device includes a glass substrate 110, an anode 120, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and a cathode 170;
the OLED device was prepared as follows:
(1) Cutting the glass substrate 110 into 50mm×50mm×0.7mm sizes, respectively sonicating in isopropyl alcohol and deionized water for 30min, and then exposing to ozone for about 10min for cleaning; mounting the resulting glass substrate with the ITO anode 120 onto a vacuum deposition apparatus;
(2) Vacuum evaporating the compound HT and the HATCN with the volume ratio of 97:3 on the ITO anode 120 to obtain a hole injection layer 130, wherein the thickness of the compound HT and the HATCN is 10 nm;
(3) Vacuum evaporating the compound HT on the hole injection layer 130 to a thickness of 120nm as the hole transport layer 140;
(4) Vacuum evaporating a compound MCP having a volume ratio of 30:70 and the organic compound M3 provided in example 1 on the hole transport layer 140 to a thickness of 20nm as the light emitting layer 150;
(5) Vacuum evaporating compounds ET and Liq with the volume ratio of 50:50 on the light-emitting layer 150, wherein the thickness is 30nm, and the compounds ET and Liq are used as an electron transport layer 160;
(6) An aluminum electrode was vacuum-deposited on the electron transport layer 160 to a thickness of 120nm as a cathode 170.
The structures of the above compounds HT, HATCN, MCP, ET and Liq are as follows:
application example 2
The present application example provides an OLED device differing from application example 1 only in that the organic compound M3 in step (4) is replaced with the organic compound M4 provided by the present invention of the same quality; the other preparation steps were identical.
Application example 3
The present application example provides an OLED device differing from application example 1 only in that the organic compound M3 in step (4) is replaced with the organic compound M5 provided by the present invention of the same quality; the other preparation steps were identical.
Comparative application example 1
The present application example provides an OLED device differing from application example 1 only in that the organic compound M3 in step (4) is replaced with a compound a of the same quality; other preparation steps are the same;
the structural formula of the organic compound A is shown as follows:
test example 1
Analog calculation of compounds
The simulation calculation method comprises the following steps: by applying the Density Functional Theory (DFT), the distribution condition and the energy level of the molecular front line orbits HOMC and LUMO are optimized and calculated under the calculation level of B3LYP/6-31G (d) through a Guassian 09 program package (Guassian Inc.), and the specific simulation method of the energy level difference AEst is referred to J.chem.theory Comput, 2013, DO1:10.1021/ct400415r, molecular structure optimization and excitation can be completed by using a TD-DFT method 'B3 LP' and a basic group '6-31 g (d)'; the simulation calculation results are shown in table 1:
TABLE 1
| Compounds of formula (I) | HOMO(eV) | LUMO(eV) | △Est(eV) |
| M3 | -5.74 | -2.63 | 0.05 |
| M4 | -5.33 | -2.42 | 0.07 |
| M5 | -5.62 | -2.66 | 0.17 |
As can be seen from the data in Table 1, the lowest singlet state and the lowest triplet state energy level difference DeltaEst of the compounds M3-M5 are smaller, and the separation of the charge donor and the charge acceptor in the organic compound provided by the invention realizes smaller DeltaEst, so that the molecule has the property of TADF.
Test example 2
Evaluation of the Performance of OLED devices
The testing method comprises the following steps: testing the currents of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain the current densities of the OLED device under different voltages; testing the brightness and radiant energy density and color coordinates of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; obtaining the current density and brightness of the OLED device under different voltages10mA/cm 2 ) Drive voltage V and current efficiency CE (cd/a); lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance 2 Under test conditions
The test results are shown in table 2:
TABLE 2
As can be seen from the data in Table 2, compared with comparative application example 1, the organic compound provided by the invention can be used as a main material of a luminescent layer of an OLED device, so that the OLED device has lower driving voltage, higher luminous efficiency and longer service life, the driving voltage is 3.70-4.02V, the current efficiency CE is 21-42cd/A, and the LT95 is 56-83h.
The organic compound provided by the invention is used as a main material of a luminescent layer of an OLED device, so that the CIE-x range of the OLED device is 0.11-0.16, and the CIE-y range is 0.11-0.13; the invention provides an organic compound which belongs to a blue heat-activated delayed luminescent material.
The applicant states that the process of the invention is illustrated by the above examples, but the invention is not limited to, i.e. does not mean that the invention must be carried out in dependence on the above process steps. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (5)
1. An organic compound, characterized in that the organic compound has a structure represented by the following formula I:
wherein L is selected from any one of single bond, unsubstituted or C1-C6 alkyl substituted phenylene;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from hydrogen, deuterium, tritium, halogen, cyano, unsubstituted or R y2 Substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R y2 Any one of substituted C1-C10 alkoxy groups; the R is y2 Any one of deuterium, tritium, halogen and cyano;
x is selected from O or S.
2. The organic compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from any one of hydrogen, deuterium, tritium, C1-C10 straight or branched alkyl.
3. The organic compound according to claim 1, characterized in that the organic compound comprises any one of the following compounds:
4. an organic light-emitting display panel, characterized in that the organic light-emitting display panel comprises an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a light-emitting layer and an electron transport layer, at least one of the light-emitting layer and the electron transport layer comprising the organic compound according to any one of claims 1 to 3.
5. An organic light-emitting display device, characterized in that the organic light-emitting display device comprises the organic light-emitting display panel according to claim 4.
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