CN115572303B - Organic light-emitting compound and application thereof - Google Patents
Organic light-emitting compound and application thereof Download PDFInfo
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- CN115572303B CN115572303B CN202211154996.2A CN202211154996A CN115572303B CN 115572303 B CN115572303 B CN 115572303B CN 202211154996 A CN202211154996 A CN 202211154996A CN 115572303 B CN115572303 B CN 115572303B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 31
- 239000010410 layer Substances 0.000 claims description 36
- 230000000903 blocking effect Effects 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 4
- 125000005259 triarylamine group Chemical group 0.000 abstract description 3
- 230000008020 evaporation Effects 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 17
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002391 heterocyclic compounds Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000001808 coupling effect Effects 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
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic electroluminescent compound, the structure of which is shown as a formula (I) or a formula (II); wherein X is selected from O or S; a 1-A2 is independently selected from substituted or unsubstituted aryl of C 6-C60 or substituted or unsubstituted heteroaryl of C 3-C60; ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C 6-C60 aryl or substituted or unsubstituted C 3-C60 heteroaryl. The organic electroluminescent compounds of the present invention are benzo-heterocyclic pyrazine derivatives, such as benzofuran/thiophene pyrazine structures, which have good electron withdrawing ability, and form a structure having electron donating-electron withdrawing groups by combining with triarylamine structures having electron donating ability. In addition, the organic electroluminescent compound contains a stable multi-ring structure, so that the stability of the material is greatly improved, and the larger molecular weight improves the glass transition temperature of the material, thereby ensuring that the material is not decomposed after long-time evaporation.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic light-emitting compound and application thereof.
Background
Researchers have synthesized a large number of organic luminescent materials and have been widely used in Organic Light Emitting Diodes (OLEDs), organic lasers, chemical sensors, biological detectors; however, in practical applications, OLED has unique characteristics in terms of full-color flat panel display, solid state lighting, and light source saving, and is considered as the most competitive research hotspot of the new generation. The OLED based on the fluorescent material has the characteristic of high stability, but is limited by the law of quantum statistics, and under the action of electric activation, the ratio of the generated singlet excitons to the triplet excitons is 1:3, so that the maximum internal quantum efficiency of the electroluminescent material is only 25%. The phosphorescent material has the spin orbit coupling effect of heavy atoms, can comprehensively utilize singlet excitons and triplet excitons, has the theoretical internal quantum efficiency of 100 percent, but has obvious efficiency roll-off effect based on the phosphorescence, and has certain obstruction in high-brightness application. Phosphorescent materials can comprehensively utilize singlet excitons and triplet excitons to realize 100% internal quantum efficiency. However, the triplet-triplet (T1-T1) is quenched in the actual operation of the device due to the relatively long exciton lifetime of the excited state of the transition metal complex. To overcome this problem, researchers often dope phosphorescent materials into organic host materials. Therefore, for high-efficiency organic light emitting diodes, it is important to develop high-performance host materials as well as guest materials.
At present, the main material widely applied to phosphorescent devices is CBP (4, 4' -di (9-carbazolyl) biphenyl), but the main material is required to have higher driving voltage and low glass transition temperature (Tg) (62 ℃) and is easy to crystallize.
Aiming at the problems of higher driving voltage and the like required by the existing main body material, the invention provides an organic light-emitting compound and application thereof.
Disclosure of Invention
The invention aims at overcoming the defects in the prior art and provides an organic light-emitting compound and application thereof.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
A first aspect of the present invention provides an organic light-emitting compound having a structure represented by formula (I) or formula (II):
Wherein R 1-R4 is each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl of C 6-C27, or substituted or unsubstituted heteroaryl of C 12-C20.
Preferably, the organic light-emitting compound is selected from:
a second aspect of the present invention provides an organic light emitting material comprising: an organic light-emitting compound as described above.
A third aspect of the present invention provides a light emitting layer comprising: an organic light emitting material as described above.
A fourth aspect of the present invention is to provide an organic electroluminescent device comprising: a light emitting layer as described above.
Preferably, the method further comprises: an anode layer, a cathode layer, and an organic functional layer disposed between the anode layer and the cathode layer, the organic functional layer including the light emitting layer.
More preferably, the organic functional layer further includes: at least one of an electron transport layer, an electron blocking layer, an electron injection layer, a hole blocking layer, or a hole transport layer.
Compared with the prior art, the invention has the following technical effects:
The invention provides an organic light-emitting compound containing an S/N heterocyclic compound and a triarylamine structure, which can be used as a green host material in an electroluminescent device; the organic luminescent compound can form a stable heterocyclic organic aromatic system, has proper HOMO and LUMO energy levels, can adjust the band gap and polarity of the system, has rich photoelectric properties, and can enable the device to have the characteristics of higher luminous efficiency, lower voltage and the like.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
It should be noted that, without conflict, the embodiments of the present invention and features of the embodiments may be combined with each other.
The invention will be further illustrated, but is not limited, by the following examples.
Example 1
To a 200mL two-necked flask containing a mixture of raw material A (5.0 mmol), raw material B (5.0 mmol), potassium carbonate (10.0 mmol) and tetraphenylpalladium phosphate (0.25 mmol) under nitrogen protection were added dry toluene (70 mL) and water (35 mL); refluxing the mixture at 100-120 deg.c for 12-24 hr; after cooling to room temperature, the mixture was extracted with DCM/water; the combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo; the residue was purified by silica gel column chromatography, followed by recrystallization from toluene to give a solid compound, which was purified by silica gel column chromatography to give intermediate 1 in a yield of 70%.
Intermediate 1 was dissolved in 40mL of triethyl phosphite and stirred for 3h at 160 ℃ under nitrogen protection, after the reaction was completed, cooled to room temperature, and after removal of the triethyl phosphite by petroleum ether flushing with a silica gel funnel, intermediate 2 was obtained in 70% yield by continuing to pass through the silica gel funnel.
Intermediate 2 (5.0 mmol), starting material R 3 -Br (5.0 mmol), sodium t-butoxide, di-palladium tris (dibenzylidene) acetonate and tri-t-butylphosphine were dissolved in 60mL of toluene and stirred at 90℃for 3 hours under nitrogen protection; after the reaction was completed, the reaction mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase anhydrous magnesium sulfate was evaporated to dryness and subjected to column chromatography to obtain intermediate 3 in 75% yield.
Raw material C (5.0 mmol), raw material D (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetone dipalladium and tri-tert-butylphosphine are dissolved in 60mL of toluene and stirred for 3 hours at 90 ℃ under the protection of nitrogen; after the reaction was completed, the mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase anhydrous magnesium sulfate was evaporated to dryness and subjected to column chromatography to give intermediate 4 in 75% yield.
Intermediate 4 (5.0 mmol), intermediate 3 (5.0 mmol), sodium t-butoxide, dipalladium tris (dibenzylidene) acetonate and tri-t-butylphosphine were dissolved in 60mL of toluene and stirred at 90 ℃ for 3 hours under nitrogen protection; after the reaction, cooling to room temperature, extracting with dichloromethane and water twice, evaporating the anhydrous magnesium sulfate in the organic phase, and performing column chromatography to obtain the target structure with the yield of 75%.
Example 2
To a 200mL two-necked flask containing a mixture of raw material A1 (5.0 mmol), raw material A2 (5.0 mmol), potassium carbonate (10.0 mmol) and tetraphenylpalladium phosphate (0.25 mmol) under nitrogen protection were added dry toluene (70 mL) and water (35 mL); refluxing the mixture at 100-120deg.C for 12-24 hr; after cooling to room temperature, the mixture was extracted with DCM/water; the combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo; the residue was purified by silica gel column chromatography, followed by recrystallization from toluene to give a solid compound, which was purified by silica gel column chromatography to give intermediate B1 in a yield of 70%.
Intermediate B1 is dissolved in 40mL of triethyl phosphite, and is stirred for 3h at 160 ℃ under the protection of nitrogen, after the reaction is finished, the reaction is cooled to room temperature, and after the triethyl phosphite is removed by using petroleum ether to wash a silica gel funnel, the intermediate B2 is obtained by continuing to pass through the silica gel funnel, and the yield is 70%.
Intermediate B2 (5.0 mmol), raw bromobenzene (5.0 mmol), sodium t-butoxide, dipalladium tris (dibenzylidene) acetonate and tri-t-butylphosphine were dissolved in 60mL of toluene and stirred at 90℃for 3 hours under nitrogen protection; after the reaction was completed, the reaction mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase anhydrous magnesium sulfate was evaporated to dryness and subjected to column chromatography to obtain intermediate B3 (yield 75%, molecular weight 453).
Raw material A4 (5.0 mmol), raw material A5 (5.0 mmol), sodium tert-butoxide, di-palladium tris (dibenzylidene) acetonate and tri-tert-butylphosphine are dissolved in 60mL of toluene and stirred for 3 hours at 90 ℃ under the protection of nitrogen; after the reaction was completed, the reaction mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase anhydrous magnesium sulfate was evaporated to dryness and subjected to column chromatography to obtain intermediate B4 (yield 75%, molecular weight 321).
Intermediate B4 (5.0 mmol), intermediate 3 (5.0 mmol), sodium t-butoxide, dipalladium tris (dibenzylidene) acetonate, and tri-t-butylphosphine were dissolved in 60mL of toluene and stirred at 90 ℃ for 3 hours under nitrogen protection; after the reaction was completed, the mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase was evaporated to dryness over anhydrous magnesium sulfate and subjected to column chromatography to give Compound 1 (yield: 75%, molecular weight: 694).
In a similar manner, compounds 2-10 were prepared, with the main reactants/intermediates involved as shown in the following table:
TABLE 1
The compounds have higher HOMO energy level and can be used as luminescent layer materials; the compound also has high thermal stability, and ensures the thermal stability of the material in the evaporation process.
Application examples
And cleaning an ITO anode layer on the transparent substrate layer, respectively ultrasonically cleaning the ITO anode layer for 15 minutes by deionized water, acetone and ethanol, then treating the ITO anode layer in a plasma cleaner for 2 minutes, and evaporating the following layer structure by adopting a vacuum evaporation mode: HAT-CN material with the thickness of 10nm is used as a hole injection layer; an NPB material with the thickness of 70nm is used as a hole transport layer; NPB material with the thickness of 20nm is used as an electron blocking layer; the organic light-emitting compound (host material) of the present invention having a thickness of 30nm and Ir (ppy) 3 (dopant material) as a light-emitting layer; TPBI material with the thickness of 40nm is used as a hole blocking/electron transport layer; a LiF material with the thickness of 1nm is used as an electron injection layer; al with a thickness of 100nm was used as a cathode.
The structure of the related formula is as follows:
TABLE 2
The OLED was characterized in a standard manner, and the electroluminescence spectrum, power efficiency (measured in cd/a) and voltage (measured at 1000cd/m 2 in V) were determined from the current-voltage-luminance characteristics (JUL characteristics). For selected experiments, lifetime was measured. The lifetime is defined as the time after which the brightness has fallen from a certain initial brightness to a certain proportion. The number T95 refers to the time at which the specified lifetime is when the luminance has fallen to 95% of the initial luminance, i.e. from 1000cd/m 2 to 950cd/m 2, for example. Different initial brightnesses are selected according to the emission color. The lifetime value may be converted to other values of the starting luminance by means of conversion formulas known to the person skilled in the art. In this context, a lifetime of 1000cd/m 2 of initial brightness is a standard value. As can be seen from table 2, when the compound provided by the invention is used as a green light-emitting host material of an organic electroluminescent device, the device has higher device efficiency, lower operating voltage and longer service life.
The invention provides an organic light-emitting compound containing an S/N heterocyclic compound and a triarylamine structure, which can be used as a green host material in an electroluminescent device; the organic luminescent compound can form a stable heterocyclic organic aromatic system, has proper HOMO and LUMO energy levels, can adjust the band gap and polarity of the system, has rich photoelectric properties, and can enable the device to have the characteristics of higher luminous efficiency, lower voltage and the like.
The foregoing description is only illustrative of the preferred embodiments of the present invention and is not to be construed as limiting the scope of the invention, and it will be appreciated by those skilled in the art that equivalent substitutions and obvious variations may be made using the teachings of the present invention, which are intended to be included within the scope of the invention.
Claims (6)
1. An organic light-emitting compound, characterized in that the organic light-emitting compound is selected from the group consisting of:
2. an organic light-emitting material, comprising: the organic light-emitting compound according to claim 1.
3. A light-emitting layer, comprising: the organic light-emitting material according to claim 2.
4. An organic electroluminescent device, comprising: a light emitting layer according to claim 3.
5. The organic electroluminescent device of claim 4, further comprising: an anode layer, a cathode layer, and an organic functional layer disposed between the anode layer and the cathode layer, the organic functional layer including the light emitting layer.
6. The organic electroluminescent device of claim 5, wherein the organic functional layer further comprises: at least one of an electron transport layer, an electron blocking layer, an electron injection layer, a hole blocking layer, or a hole transport layer.
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| CN114436942A (en) * | 2022-02-18 | 2022-05-06 | 长春海谱润斯科技股份有限公司 | Arylamine compound containing carbazole group and organic electroluminescent device thereof |
| CN114539270A (en) * | 2021-12-09 | 2022-05-27 | 上海钥熠电子科技有限公司 | Compound containing carbazole derivative and application thereof in organic electroluminescent device |
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| CN114539270A (en) * | 2021-12-09 | 2022-05-27 | 上海钥熠电子科技有限公司 | Compound containing carbazole derivative and application thereof in organic electroluminescent device |
| CN114436942A (en) * | 2022-02-18 | 2022-05-06 | 长春海谱润斯科技股份有限公司 | Arylamine compound containing carbazole group and organic electroluminescent device thereof |
Non-Patent Citations (1)
| Title |
|---|
| Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors;Isabel C. F. R. Ferreira;《Tetrahedron Letters》;第44卷;4327-4329 * |
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