CN109369598A - A kind of luminous organic material and preparation method and the organic luminescent device containing the material - Google Patents
A kind of luminous organic material and preparation method and the organic luminescent device containing the material Download PDFInfo
- Publication number
- CN109369598A CN109369598A CN201811270524.7A CN201811270524A CN109369598A CN 109369598 A CN109369598 A CN 109369598A CN 201811270524 A CN201811270524 A CN 201811270524A CN 109369598 A CN109369598 A CN 109369598A
- Authority
- CN
- China
- Prior art keywords
- compound
- preparation
- alkyl
- layer
- organic material
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- 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
- H10K85/649—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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention relates to luminescent material technical fields, and in particular to a kind of luminous organic material and preparation method and the organic luminescent device containing the material.The present invention provides a kind of luminous organic material of structure novel to solve the problems, such as that above-mentioned routine techniques exists.It realizes with excellent luminous efficiency and the organic luminescent device in significantly improved service life.Luminous organic material provided by the invention, the compound, which has, compared with conventional body material can show excellent Electroluminescence Properties, the device lifetime of length and appropriate chromaticity coordinates.The organic luminescent device of high efficiency provided by the invention and long-life, the device use luminous organic material of the present invention as electroluminescent material.The preparation method of luminous organic material provided by the invention, synthetic method is simple and easy, by the temperature and time of control reaction, can get the target product of high yield.
Description
Technical field
The present invention relates to luminescent material technical fields, and in particular to a kind of luminous organic material and preparation method and contains the material
Organic luminescent device.
Background technique
The characteristics such as organic electroluminescence device has wide viewing angle, the response time is short, driving voltage is low, and can have by three kinds
Electroluminescent material (for red, green and blue) can be used to realize full color OLED display.Important item is to develop
Electroluminescent material with high efficiency and long-life, to improve the overall characteristic of organic electroluminescent (EL) device.Recently, it grinds
The organic EL device of high efficiency processed and long-life become a urgent project.It is high-purity to property needed for material of main part,
Glass transition temperature and thermal decomposition temperature are sufficiently high, to guarantee thermal stability.In addition, material of main part should have high electrification
Stability is learned, to provide the long-life.Amorphous phase film easy to form, and there is high adherence with other adjacent materials, but not
Middle layer migration occurs.
Dinaphthyl anthracene (DNA) is widely applied blue light host compound.But the compound is applied to total colouring
When device, the service life only has thousands of hours, the reason is that excitation purity is reduced with the operating time.In blue coloured electroluminous situation, if
Electroluminescence wavelength slightly moves to more long wavelength, is advantageous in terms of luminous efficiency.But the because blue excitation purity of material
It is not high enough, therefore be difficult for material to be applied to the display of high quality.Moreover, because there are excitation purity, efficiency and thermal stability
Problem and there is an urgent need to research and develop this kind of material.
Summary of the invention
The invention solves in the prior art the technical issues of, provide a kind of luminous organic material and preparation method and containing the material
The organic luminescent device of material.The present invention provides a kind of luminous organic materials of structure novel, should compared with conventional body material
Compound have can show excellent Electroluminescence Properties, the device lifetime of length and appropriate chromaticity coordinates.Use the organic light emission material
Expect the device as electroluminescent material, realizes with excellent luminous efficiency and the organic illuminator in significantly improved service life
Part.
In order to solve the above-mentioned technical problem, technical solution of the present invention is specific as follows:
A kind of luminous organic material, structural formula are as follows:
In formula:
X is oxygen；
R1To R8It each independently represents: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60
Naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyls
Base, adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl
Amino, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；
R9To R12Each independently represent: hydrogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, contains one at halogen
A or multiple heteroatomic 5- members or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 alkyl first silicon selected from N, O and S
Alkyl, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, bis- ring of C7-C60
Alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino,
C6-C60 aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl
Base；
And R9With R10Or R10With R11Or R11With R12It is connected with each other cyclization；
Ar is indicated: C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, containing one or more miscellaneous selected from N, O and S
The 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 of atom
Arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynes
Base, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-
C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl.
In the above-mentioned technical solutions, the luminous organic material is selected from the chemical combination that following formula 2 is indicated to one of 4
Object:
In the above-mentioned technical solutions, the luminous organic material is selected from the chemical combination that following formula 1 is indicated to one of 84
Object:
The present invention also provides a kind of preparation methods of luminous organic material, comprising the following steps:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen
In atmosphere, reactant is flowed back and is stirred to react, extracted again with methylene chloride and distilled water after reaction, then is dry with magnesium sulfite
Dry extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product by silica gel column chromatography, obtains intermediate
2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining compound shown in chemical formula 1；
Its synthetic route is as follows:
In the above-mentioned technical solutions, the time being stirred at room temperature in step 1 be 18-22 hours, be stirred to react in step 2 when
Between be 10-14 hour, the temperature reacted in step 3 is 80-100 DEG C, and the time being stirred to react in step 4 is 18-22 hours, is walked
The temperature reacted in rapid 5 is 80-100 DEG C.
In the above-mentioned technical solutions, the time being stirred at room temperature in step 1 is 20 hours, the time being stirred to react in step 2
It is 12 hours, the temperature reacted in step 3 is 90 DEG C, and the time being stirred to react in step 4 is 20 hours, is reacted in step 5
Temperature is 90 DEG C.
In the above-mentioned technical solutions, toluene/ethanol/water volume ratio described in step 3 and step 5 is 3:1:1.
The present invention also provides a kind of organic luminescent device containing above-mentioned luminous organic material, including first electrode, the second electricity
Pole, and at least one layer of organic layer being inserted between the first electrode and second electrode；Wherein, the organic layer includes electroluminescent hair
Photosphere, the electroluminescence layer include luminous organic material shown in chemical formula 1.
In the above-mentioned technical solutions, the organic layer includes one or more compounds selected from anthracene class.
In the above-mentioned technical solutions, the organic layer further includes electron injecting layer, electron transfer layer, hole blocking layer, electricity
Sub- barrier layer, hole transmission layer, at least one layer in hole injection layer.
The beneficial effects of the present invention are:
The present invention provides a kind of luminous organic material of structure novel to solve the problems, such as that above-mentioned routine techniques exists.It is real
Show with excellent luminous efficiency and the organic luminescent device in significantly improved service life.
Luminous organic material provided by the invention, the compound is excellent electroluminescent with that can show compared with conventional body material
Luminosity, the device lifetime of length and appropriate chromaticity coordinates.
The organic luminescent device of high efficiency provided by the invention and long-life, the device use organic light emission of the present invention
Material is as electroluminescent material.
The preparation method of luminous organic material provided by the invention, synthetic method is simple and easy, by control reaction temperature and
Time can get the target product of high yield.
Specific embodiment
The present invention provides a kind of luminous organic material, and structural formula is as follows:
In formula: X is oxygen；R1To R8Each independently represent: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 are miscellaneous
Aryl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-
C60 arylsilyl groups, adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl ammonia
Base, C6-C60 arylamino, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；R9To R12It is respectively independent
Ground indicates: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, containing one or more miscellaneous selected from N, O and S
The 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 of atom
Arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynes
Base, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-
C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；And R9With R10Or R10With
R11Or R11With R12It is connected with each other cyclization；Ar is indicated: C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, containing one or
It is multiple selected from N, O and S heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups,
Two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl,
C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60
Aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl.
It is preferred that the luminous organic material is selected from the compound that following formula 2 is indicated to one of 4:
The most preferably described luminous organic material is selected from the compound that following formula 1 is indicated to one of 84:
The present invention also provides a kind of preparation methods of luminous organic material, comprising the following steps:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen
In atmosphere, reactant is flowed back and is stirred to react, extracted again with methylene chloride and distilled water after reaction, then is dry with magnesium sulfite
Dry extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product by silica gel column chromatography, obtains intermediate
2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixing is stirred at room temperature
Water is added when the reactions are completed in object thereto, and mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound
It is recrystallized from ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, replaced using nitrogen empty
Three times, four (triphenyl phosphorus) palladiums are added in gas, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；To
After reaction, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；Use diatomite
Catalyst is removed, washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is divided using silica gel funnel
From obtaining compound shown in chemical formula 1；
Its synthetic route is as follows:
The time being stirred at room temperature in preferred steps 1 is 18-22 hours, and the time being stirred to react in step 2 is that 10-14 is small
When, the temperature reacted in step 3 is 80-100 DEG C, and the time being stirred to react in step 4 is 18-22 hours, is reacted in step 5
Temperature is 80-100 DEG C.
The time being most preferably stirred at room temperature in step 1 is 20 hours, and the time being stirred to react in step 2 is 12 hours, step
The temperature reacted in rapid 3 is 90 DEG C, and the time being stirred to react in step 4 is 20 hours, and the temperature reacted in step 5 is 90 DEG C.
Toluene/ethanol/water volume ratio described in preferred steps 3 and step 5 is 3:1:1.
The present invention also provides a kind of organic luminescent device containing above-mentioned luminous organic material, including first electrode, the second electricity
Pole, and at least one layer of organic layer being inserted between the first electrode and second electrode；Wherein, the organic layer includes electroluminescent hair
Photosphere, the electroluminescence layer include luminous organic material shown in chemical formula 1.
It is preferred that the organic layer includes one or more compounds selected from anthracene class.
It is preferred that the organic layer further includes electron injecting layer, electron transfer layer, hole blocking layer, electronic barrier layer, hole
At least one layer in transport layer, hole injection layer.
Luminous organic material and its preparation method in order to further illustrate the present invention and the device manufactured by the luminescent material and
Its luminosity, just representative compound of the invention further describes the present invention, provides following embodiment content and is intended merely to
Illustrate embodiments of the present invention, without constituting limitation of the scope of the invention in any way.
The intermediate that final product is used to prepare involved in following embodiment can refer to following synthetic routes 1 and be made
Synthetic route 1
The final product of following embodiment preparation can refer to following synthetic routes 2 and be made.
Synthetic route 2
The preparation of [preparation example 1] compound 1
The preparation of intermediate A -1-1
Raw material SM-1-1 (71.9mmol), raw material SM-2-1 (71.9mmol), alchlor (107.85mmol) are added
Into methylene chloride.Three times using nitrogen displaced air, the reaction overnight at 50 DEG C, TLC monitoring.To after reaction, in nitrogen
It is cooled to room temperature under gas shielded.It adds water and stirs, carries out liquid separation using separatory funnel, retain organic phase.Concentration, is carried out using ethyl alcohol
Mashing washing obtains intermediate A -1-1 (57.52mmol yield is 80%).
The preparation of compound B-1-1
Reaction is added in compound A-1-1 (57.52mmol), potassium carbonate (172.56mmol) and 2- butanone (300mL) to hold
Device is heated to reflux.When the reactions are completed, it is concentrated under reduced pressure, gained compound recrystallization from ethyl alcohol (200mL) obtains compound
B-1-1 (51.77mmol yield is 90%).
The preparation of compound C-1-1
By compound B-1-1 (51.77mmol), BH3Me2S (77.66mmol) is added in 300mL tetrahydrofuran solvent.
It is heated to 45 DEG C under nitrogen protection.TLC monitoring.To after reaction, be cooled to room temperature under nitrogen protection, add water and DCM,
Liquid separation is carried out using separatory funnel, retains organic phase.Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated using silica gel funnel,
Obtain compound C-1-1 (49.18mmol yield is 95%).
The preparation of compound D-1-1
Compound C-1-1 (49.18mmol), raw material SM-3-1 (63.94mmol), potassium carbonate (147.54mmol) are added
To 300mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Three times using nitrogen displaced air, four (triphens are added
Base phosphorus) palladium (0.49mmol), it uses nitrogen displaced air three times again, is heated to 90 DEG C under nitrogen protection.TLC monitoring.To anti-
After answering, it is cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, retains organic phase.Use diatom earth removal
Catalyst is removed, washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated using silica gel funnel,
Obtain compound D-1-1 (43.28mmol yield is 88%).
The preparation of compound E-1-1
Compound D-1-1 (43.28mmol), N-bromosuccinimide (NBS) (64.92mmol) and methylene chloride is molten
Reaction vessel is added in agent (300mL), the mixture is stirred at room temperature 20 hours.When the reactions are completed, water is added thereto
(100mL), mixture are extracted with methylene chloride (200mL).The lower filtering of extract liquor decompression, gained compound is from ethyl alcohol (200mL)
Middle recrystallization obtains compound E-1-1 (36.79mmol yield is 85%).
The preparation of compound 1
Compound E-1-1 (36.79mmol), phenyl boric acid (44.15mmol), potassium carbonate (110.37mmol) are added to
500mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Three times using nitrogen displaced air, four (triphenyls are added
Phosphorus) palladium (0.37mmol), it uses nitrogen displaced air three times again, is heated to 90 DEG C under nitrogen protection.TLC monitoring.Wait react
After, it is cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, retains organic phase.It is removed using diatomite
Catalyst washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To compound 1 (30.54mmol yield is 83%), mass spectrometry value 484.21.
The preparation of [preparation example 2] compound 5
It, will according to the preparation method of compound 1It replaces withAccording in the synthesis of synthetic route 1
MesosomeIt willIt replaces withIt willIt replaces withIt willIt replaces withCompound 5, matter is prepared
Spectrum is 636.30.
The preparation of [preparation example 3] compound 21
It, will according to the preparation method of compound 5It replaces withIt willIt replaces withPrepare compound 21, mass spectrometry value 966.42.
The preparation of [preparation example 4] compound 29
According to 1 synthetic intermediate of synthetic routeIt, will according to the preparation method of compound 1It replaces withPrepare compound 29, mass spectrometry value 484.20.
The preparation of [preparation example 5] compound 35
According to 1 synthetic intermediate of synthetic routeIt, will according to the preparation method of compound 5It replaces withIt willIt replaces withIt willIt replaces withPrepare compound 35, mass spectrometry value 762.32.
The preparation of [preparation example 6] compound 51
It, will according to the preparation method of compound 35It replaces withIt willIt replaces withPrepare compound 51, mass spectrometry value 874.35.
The preparation of [preparation example 7] compound 57
According to 1 synthetic intermediate of synthetic routeIt, will according to the preparation method of compound 1It replaces withPrepare compound 57, mass spectrometry value 484.21.
The preparation of [preparation example 8] compound 67
According to 1 synthetic intermediate of synthetic routeIt willIt replaces withIt willIt replaces withIt willIt replaces withAccording to the preparation method of compound 35, prepare compound 67, mass spectrometry value 760.31.
The preparation of [preparation example 9] compound 79
It, will according to the preparation method of compound 51It replaces withBy preparationization
Close object 79, mass spectrometry value 874.35.
The preparation of [preparation example 10] compound 20
Starting material SM-3-1 and C-1-1 are changed and make SM-3-2 and SM-4-1, according to compound E-1-1 prepare method,
Obtain compound E-1-2.
By compound E-1-2 (12.6mmol), Pd2(dba)3(0.13mmol 0.26g), connection pinacol borate
(25.2mmol) and potassium acetate (37.8mmol) are dissolved in dry 1,4- dioxane.In nitrogen atmosphere, reactant is returned
It flows and stirs 12 hours, then extracted 3 times with methylene chloride and distilled water.It with the dry extraction product of magnesium sulfite and filters, then
It is concentrated under reduced pressure filtration product.Enriched product is purified by silica gel column chromatography, obtaining compound F-1-1, (10.46mmol yield is
83%)
Compound F-1-1 (10.46mmol), C-1-2 (11.5mmol), potassium carbonate (9.6g 69.54mmol) are added to
300mL toluene/ethanol/water (volume ratio 3:1:1) in the mixed solvent.Three times using nitrogen displaced air, four (triphenyls are added
Phosphorus) palladium (0.11mmol), it uses nitrogen displaced air three times again, is heated to 90 DEG C under nitrogen protection.TLC monitoring.Wait react
After, it is cooled to room temperature under nitrogen protection.Liquid separation is carried out using separatory funnel, retains organic phase.It is removed using diatomite
Catalyst washes diatomite to no product with DCM.Filtrate is concentrated to a small amount of, silica gel mixed sample, is carried out using silica gel funnel isolated
Compound 20 (8.9mmol yield is 85%), mass spectrometry value 944.43.
The preparation of [preparation example 11] compound 43
It, will according to the preparation method of compound 35It replaces withIt willIt replaces withPrepare compound 43, mass spectrometry value 888.36.
The preparation of [preparation example 12] compound 70
It, will according to the preparation method of compound 79It replaces withIt willIt replaces
It is changed toPrepare compound 70, mass spectrometry value 800.33.
Organic luminescent device is manufactured using the compound of the present invention.
[embodiment 1]
It is by Fisher Co., Ltd's coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic wave
Washing 30 minutes, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, distilled water clean after, isopropanol, acetone,
Ultrasonic washing is later dry in order for methanol equal solvent, is transferred in plasma washing machine, and aforesaid substrate is washed 5 points
Clock is sent in evaporator.The 4,4' for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for, 4 "-three [2- naphthalenes
Phenyl amino] triphenylamine (2-TNATA) be used as hole injection layer.On the hole injection layer of formation vacuum evaporation with a thickness of
N'- bis- (1- naphthalene)-N of 30nm, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines (NPB) are used as hole transmission layer.Then
The compound of the present invention 1 that evaporation thickness is 30nm on above-mentioned hole transmission layer is used as material of main part and dopant material 4,4'-
Bis- [4- (di-p-tolyl amino) styryl] biphenyl (DPAVBi).The weight ratio of material of main part and dopant material is 97:3.
Then on above-mentioned luminescent layer vacuum evaporation with a thickness of 10nm bis- (2- methyl -8-hydroxyquinoline-N1,08)-(1,1 '-biphenyl -
4- hydroxyl) aluminium (BAlq) be used as hole blocking layer.On above-mentioned hole blocking layer vacuum evaporation with a thickness of 40nm three (8- hydroxyls
Quinoline) aluminium (III) Alq3 is as electron transfer layer.Vacuum evaporation is on above-mentioned electron transfer layer with a thickness of 0.5nm lithium fluoride
(LiF), as electron injecting layer.The aluminium that last evaporation thickness is 150nm completes organic luminescent device as cathode with this
Preparation.
[embodiment 2]
Other than replacing compound 1 with compound 5, organic luminescent device is prepared with method same as Example 1.
[embodiment 3]
Other than replacing compound 1 with compound 21, organic luminescent device is prepared with method same as Example 1.
[embodiment 4]
Other than replacing compound 1 with compound 29, organic luminescent device is prepared with method same as Example 1.
[embodiment 5]
Other than replacing compound 1 with compound 35, organic luminescent device is prepared with method same as Example 1.
[embodiment 6]
Other than replacing compound 1 with compound 51, organic luminescent device is prepared with method same as Example 1.
[embodiment 7]
Other than replacing compound 1 with compound 57, organic luminescent device is prepared with method same as Example 1.
[embodiment 8]
Other than replacing compound 1 with compound 67, organic luminescent device is prepared with method same as Example 1.
[embodiment 9]
Other than replacing compound 1 with compound 79, organic luminescent device is prepared with method same as Example 1.
[embodiment 10]
Other than replacing compound 1 with compound 20, organic luminescent device is prepared with method same as Example 1.
[embodiment 11]
Other than replacing compound 1 with compound 43, organic luminescent device is prepared with method same as Example 1.
[embodiment 12]
Other than replacing compound 1 with compound 70, organic luminescent device is prepared with method same as Example 1.
[comparative example 1]
In addition to compound 9,10- is bis--(1- naphthalene) anthracene (ADN) replaces other than compound 1, with same as Example 1
Method prepares organic luminescent device.
The Electroluminescence Properties of the organic luminescent device of above-mentioned manufacture
Efficiency (the electricity for each organic electroluminescence device that evaluation is manufactured according to embodiment 1 to embodiment 12 and comparative example 1
Current density: 10mA/cm2) and service life (10mA/cm2T90 under current density).
Therefore, the compound of the present invention may be used as efficient blue electroluminescent material.In addition, applied the present invention
Compound significant improvement is shown in terms of excitation purity as the device of material of main part.At two aspects of service life and luminous efficiency
Improvement confirm the compound of the present invention have excellent property.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of luminous organic material, which is characterized in that its structural formula is as follows:
In formula:
X is oxygen；
R1To R8It each independently represents: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkanes
Base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups,
Adamantyl, C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 aryl ammonia
Base, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
Alternatively, R1To R8In each can be with adjacent substituent group cyclization or monocycle or polycyclic aromatic ring；
R9To R12Each independently represent: hydrogen, halogen, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, containing one or
It is multiple selected from N, O and S heteroatomic 5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups,
Two C1-C60 alkyl C6-C60 arylsilyl groups, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl,
C2-C60 alkenyl, C2-C60 alkynyl, C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60
Aryl C1-C60 alkyl, C6-C60 aryloxy group, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl；
And R9With R10Or R10With R11Or R11With R12It is connected with each other cyclization；
Ar is indicated: C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, the hetero atoms containing one or more selected from N, O and S
5- member or 6- membered heterocycloalkyl, C3-C60 naphthenic base, three C1-C60 aIkylsilyl groups, two C1-C60 alkyl C6-C60 aryl
Silicyl, three C6-C60 arylsilyl groups, adamantyl, C7-C60 bicyclic alkyl, C2-C60 alkenyl, C2-C60 alkynyl,
C1-C60 alkoxy, cyano, C1-C60 alkyl amino, C6-C60 arylamino, C6-C60 aryl C1-C60 alkyl, C6-C60 virtue
Oxygroup, C6-C60 arylthio, C1-C60 alkoxy carbonyl, carboxyl, nitro or hydroxyl.
2. luminous organic material according to claim 1, which is characterized in that it is selected from following formula 2 to one of 4 tables
The compound shown:
3. luminous organic material according to claim 1, which is characterized in that it is selected from following formula 1 to one of 84
The compound of expression:
4. a kind of preparation method of luminous organic material described in claim 1-3 any one, which is characterized in that including following step
It is rapid:
The preparation of step 1, intermediate 1
Reaction vessel is added in compound 1, N-bromosuccinimide and dichloromethane solvent, the mixture is stirred at room temperature,
When the reactions are completed, water is added thereto, mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound from
It is recrystallized in ethyl alcohol, obtains intermediate 1；
The preparation of step 2, intermediate 2
By intermediate 1, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in Isosorbide-5-Nitrae-dioxane, in nitrogen atmosphere,
Reactant is flowed back and is stirred to react, is extracted again with methylene chloride and distilled water after reaction, then is extracted with magnesium sulfite is dry
It takes product and filters, be then concentrated under reduced pressure filtration product, enriched product is purified by silica gel column chromatography, obtains intermediate 2；
The preparation of step 3, intermediate 3
Intermediate 2, compound 2, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, use nitrogen displaced air three
It is secondary, four (triphenyl phosphorus) palladiums are added, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；Wait react
After, it is cooled to room temperature under nitrogen protection, carries out liquid separation using separatory funnel, retain organic phase；It is removed using diatomite
Catalyst washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To intermediate 3；
The preparation of step 4, intermediate 4
Reaction vessel is added in intermediate 3, N-bromosuccinimide and dichloromethane solvent, the mixture is stirred at room temperature,
When the reactions are completed, water is added thereto, mixture is extracted with dichloromethane, the lower filtering of extract liquor decompression, gained compound from
It is recrystallized in ethyl alcohol, obtains intermediate 4；
The preparation of compound shown in step 5, chemical formula 1
Intermediate 4, compound 3, potassium carbonate are added to toluene/ethanol/water in the mixed solvent, use nitrogen displaced air three
It is secondary, four (triphenyl phosphorus) palladiums are added, again three times with nitrogen displaced air, react under nitrogen protection, TLC monitoring；Wait react
After, it is cooled to room temperature under nitrogen protection；Liquid separation is carried out using separatory funnel, retains organic phase；It is removed using diatomite
Catalyst washes diatomite to no product with DCM；Filtrate is concentrated to a small amount of, silica gel mixed sample, is separated, is obtained using silica gel funnel
To compound shown in chemical formula 1；
Its synthetic route is as follows:
5. the preparation method of luminous organic material according to claim 4, which is characterized in that the time being stirred at room temperature in step 1
It is 18-22 hours, the time being stirred to react in step 2 is 10-14 hours, and the temperature reacted in step 3 is 80-100 DEG C, step
The time being stirred to react in 4 is 18-22 hours, and the temperature reacted in step 5 is 80-100 DEG C.
6. the preparation method of luminous organic material according to claim 4, which is characterized in that the time being stirred at room temperature in step 1
It is 20 hours, the time being stirred to react in step 2 is 12 hours, and the temperature reacted in step 3 is 90 DEG C, is stirred in step 4 anti-
The time answered is 20 hours, and the temperature reacted in step 5 is 90 DEG C.
7. the preparation method of luminous organic material according to claim 4, which is characterized in that first described in step 3 and step 5
Benzene/ethanol/water volume ratio is 3:1:1.
8. a kind of organic luminescent device, including first electrode, second electrode, and at least one layer of insertion first electrode and second
Organic layer between electrode；Wherein, the organic layer includes electroluminescence layer, which is characterized in that the electroluminescence layer includes
Luminous organic material shown in chemical formula 1.
9. organic luminescent device according to claim 8, which is characterized in that the organic layer includes one or more is selected from
The compound of anthracene class.
10. organic luminescent device according to claim 8, which is characterized in that the organic layer further include electron injecting layer,
Electron transfer layer, hole blocking layer, electronic barrier layer, hole transmission layer, at least one layer in hole injection layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811270524.7A CN109369598A (en) | 2018-10-29 | 2018-10-29 | A kind of luminous organic material and preparation method and the organic luminescent device containing the material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811270524.7A CN109369598A (en) | 2018-10-29 | 2018-10-29 | A kind of luminous organic material and preparation method and the organic luminescent device containing the material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109369598A true CN109369598A (en) | 2019-02-22 |
Family
ID=65390577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811270524.7A Withdrawn CN109369598A (en) | 2018-10-29 | 2018-10-29 | A kind of luminous organic material and preparation method and the organic luminescent device containing the material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109369598A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110467545A (en) * | 2019-07-22 | 2019-11-19 | 广东工业大学 | A kind of anthracene derivant and its preparation method and application |
| WO2021049656A1 (en) * | 2019-09-13 | 2021-03-18 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008069100A (en) * | 2006-09-13 | 2008-03-27 | Tdk Corp | Compound for organic el element and organic el element |
| CN101560186A (en) * | 2008-03-28 | 2009-10-21 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN102712639A (en) * | 2009-11-12 | 2012-10-03 | 保土谷化学工业株式会社 | Compound having a substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent element |
| CN103214337A (en) * | 2008-04-02 | 2013-07-24 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN107880057A (en) * | 2016-09-30 | 2018-04-06 | 三星显示有限公司 | Fused ring compound and the organic light emitting apparatus for including it |
-
2018
- 2018-10-29 CN CN201811270524.7A patent/CN109369598A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008069100A (en) * | 2006-09-13 | 2008-03-27 | Tdk Corp | Compound for organic el element and organic el element |
| CN101560186A (en) * | 2008-03-28 | 2009-10-21 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103214337A (en) * | 2008-04-02 | 2013-07-24 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN102712639A (en) * | 2009-11-12 | 2012-10-03 | 保土谷化学工业株式会社 | Compound having a substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent element |
| CN107880057A (en) * | 2016-09-30 | 2018-04-06 | 三星显示有限公司 | Fused ring compound and the organic light emitting apparatus for including it |
Non-Patent Citations (1)
| Title |
|---|
| 徐玉良、方浩: "芳基硼酸类化合物合成研究进展", 《有机化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110467545A (en) * | 2019-07-22 | 2019-11-19 | 广东工业大学 | A kind of anthracene derivant and its preparation method and application |
| WO2021049656A1 (en) * | 2019-09-13 | 2021-03-18 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102933531B (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR100955993B1 (en) | Compound for organic electroluminescent device and organic electroluminescent device | |
| CN101410356B (en) | Novel compound and organic light emitting device using the compound | |
| CN103249722A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| CN104498025B (en) | Many phenyl benzene constructs cyano-containing light emitting molecule and its production and use | |
| KR20120032054A (en) | Novel organic luminescent compounds and organic electroluminescent device using the same | |
| CN109369660A (en) | Luminous organic material and its preparation method and organic electroluminescence device containing the material | |
| CN104326980B (en) | Based on 4,4 '-Lian two fluorene structured 9, the material of main part that 9 '-position connects and application thereof | |
| KR20040049038A (en) | Phenyl pyridine - iridium metal complex compounds for organic electroluminescent device, process for preparing them and organic electroluminescent device using them | |
| CN109535131A (en) | It is a kind of using cyanopyridine as the compound of receptor and its application | |
| CN112375071B (en) | Organic light-emitting compound and preparation method and application thereof | |
| CN108602783A (en) | Organic electroluminescent element and electronic device | |
| CN105481672A (en) | Series of fluorescent OLED materials | |
| CN107056807B (en) | It is a kind of using equal benzene as the compound of core and its application in organic electroluminescence device | |
| CN112745342A (en) | Fused heterocyclic compound and organic electroluminescent device thereof | |
| CN102596893A (en) | Triarylamine compounds for electronic applications | |
| CN110804053B (en) | Electronic transmission material of imidazoazacycle and preparation method and application thereof | |
| CN109369598A (en) | A kind of luminous organic material and preparation method and the organic luminescent device containing the material | |
| CN106188141B (en) | A kind of OLED material and its application | |
| CN105566320A (en) | Pyridine-quinoline derivative, preparation method and organic light-emitting device | |
| CN108165264A (en) | A kind of organic luminescent compounds and its preparation method and application | |
| CN105777809A (en) | Organic electroluminescence material and organic electroluminescence device | |
| CN109456297A (en) | A kind of luminous organic material and its preparation method and the organic electroluminescence device containing the material | |
| CN108503630A (en) | A kind of thermal activation delayed fluorescence material and its application | |
| CN108707103A (en) | A kind of hot activation delayed fluorescence material and its light-emitting device |
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 | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190222 |
|
| WW01 | Invention patent application withdrawn after publication |