CN105907388B - A kind of condensed-nuclei aromatics compound and preparation method and application - Google Patents
A kind of condensed-nuclei aromatics compound and preparation method and application Download PDFInfo
- Publication number
- CN105907388B CN105907388B CN201610309806.8A CN201610309806A CN105907388B CN 105907388 B CN105907388 B CN 105907388B CN 201610309806 A CN201610309806 A CN 201610309806A CN 105907388 B CN105907388 B CN 105907388B
- Authority
- CN
- China
- Prior art keywords
- condensed
- compound
- nuclei aromatics
- reaction
- solvent
- 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.)
- Active
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/88—Growth and elimination reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention proposes a kind of condensed-nuclei aromatics compound and preparation method and application, and more particularly simultaneously indene derivative (TrBr) obtains six aryl three and indene derivative to hexabromo three with 2 aryl boric acids by the Suzuki coupling reactions of microwave radiation technology；Then, what the oxidative dehydrogenation cyclization using ferric trichloride/nitromethane as oxidant obtained that gradually dehydrogenation obtains is a kind of based on three and condensed-nuclei aromatics compound that indenes is core.The compound concrete structure general formula is shown below：Wherein, Ar is selected from one of following group：R is the linear or branched alkyl group of C1 C20, and * represents link site.The compound has the characteristics that be easy to purifying, good dissolubility, easily forms self-assembled structures in the solution, can obtain high chemical purity by easy column chromatography method, can be widely applied in organic electro-optic device.
Description
Technical field
The invention belongs to photoelectric materials and applied technical field, and in particular to a kind of condensed-nuclei aromatics compound and preparation method thereof
With application, relate more specifically to it is a kind of based on three and indene derivative for core condensed-nuclei aromatics compound and preparation method thereof with should
With.
Background technology
The nano-graphene molecule of condensed-nuclei aromatics class, since it has the characteristics that graphene film segment structure, increasingly by people
Extensive concern.Due to its unique characteristic electron and self assembly performance, it is widely used in various electronic devices, such as
Organic field effect tube, organic solar batteries and Organic Light Emitting Diode etc..In recent years, with electronic device constantly to it is low into
This exploitation, flexibility, light-weight direction are developed, and the condensed-nuclei aromatics compound of small-medium size seems the application value for having bigger.
Its high luminescence energy, high carrier mobility and antioxygenic property, along with the confirmability of structure, these all show it
In the wide application prospect in organic photoelectric field.However, with pi-conjugated expansion, the dissolubility of organic condensed-nuclei aromatics compound with
And accumulation is easily formed in the solution as a problem, this problem hinders the practical application of condensed-nuclei aromatics compound.
To solve the above-mentioned problems, we have proposed based on three and indenes it is thick to reduce for the molecular structure of the cloverleaf pattern of core
The aggregation of aromatic compound in a solvent.A kind of method of novel effective structure cloverleaf pattern condensed-nuclei aromatics is developed.
Invention content
Technical problem：The purpose of the present invention is to provide a kind of condensed-nuclei aromatics compound and preparation method thereof with it organic
The application of photoelectric device.It is to pass through microwave radiation technology using hexabromo three and indene derivative and 2- aryl boric acids as starting material
Six aryl three and indene derivative is obtained by the reaction in Suzuki, is aoxidized by ferric trichloride/nitromethane system as oxidant
Dehydrocyclization generates the condensed-nuclei aromatics compound of dehydrocyclization.
Technical solution：Using three, simultaneously indene derivative is nuclear structure to a kind of condensed-nuclei aromatics compound of the present invention, with such as following formula I
Shown general structure：
Wherein, Ar is selected from one of following group：
R is the linear or branched alkyl group of C1-C20, and * represents link site.
The synthetic method of condensed-nuclei aromatics compound of the present invention is：Hexabromo three and indene derivative are added under inert atmosphere
TrBr, tetrabutyl ammonium fluoride, potassium hydroxide, 2- aryl boric acids and tetra-triphenylphosphine palladium are simultaneously dissolved in solvent, in microwave reactor
Gained crude product separating-purifying is obtained six aryl three and indene derivative by 100-180 DEG C of reaction after reaction；Again by gained six
Aryl three and indene derivative are dissolved in solvent under an inert atmosphere, and ferric trichloride/nitromethane oxidation system is added dropwise at -10-10 DEG C,
Nitrogen blistering reaction is passed through, gained crude product is purified by pillar layer separation, obtains the condensed-nuclei aromatics as shown in reaction formula I
Close object.
The preparation method of the condensed-nuclei aromatics compound specifically includes following steps：
Step 1：Hexabromo three and indenes, tetrabutyl ammonium fluoride, potassium hydroxide, 2- aryl boric acids and four are added under an inert atmosphere
Triphenylphosphine palladium is simultaneously dissolved in solvent A, in the reaction of 100-180 DEG C of microwave reactor, through being quenched, washing, extracting, drying, obtains thick
Product separating-purifying；
Step 2：Product obtained by step 1 is dissolved in solvent B, at -10-10 DEG C, ferric trichloride/nitromethane oxygen is added dropwise
Change system is passed through nitrogen blistering reaction；Methanol is quenched, extracts, dry after, filter, obtain crude product, separating-purifying.
The volume ratio of the molal quantity and solvent A of the reactant hexabromo three and indenes is 1mmol：(2~10) mL, hexabromo three is simultaneously
The molar equivalent of indenes and tetra-triphenylphosphine palladium ratio is 1：(5~10) %.
Solvent B in the step 2 is one in dichloromethane DCM, tetrahydrofuran THF, N,N-dimethylformamide DMF
Kind is several.
The molal quantity of 1 product of reaction step is 1mmol with the volume ratio of solvent B：(5~15) mL, 1 product of reaction step with
The molar equivalent ratio of ferric trichloride is 1：(4.0~9.0).
Solvent A in the step 1 is in dichloromethane DCM, tetrahydrofuran THF or N,N-dimethylformamide DMF
It is one or more of.
A kind of condensed-nuclei aromatics compound application in the opto-electronic device of the present invention is：The compound mainly as
The luminescent layer of organic electroluminescence device and the electron transfer layer of organic field effect tube are used to build having for efficient stable
Machine photoelectric device.
Advantageous effect：Condensed-nuclei aromatics compound proposed by the present invention has the characteristics that：(1) cloverleaf pattern of the compound
Structure be conducive to prevent it is intermolecular tightly packed, three and indenes on the substitution of alkyl chain increase its dissolving in common solvent
Degree；(2) the rigid arm configuration after condensed ring has preferable fluorescence quantum efficiency, can enhance the solid state fluorescence transmitting of molecule；(3) should
Compound can be self-assembled into ordered structure in the solution；(4) can photoelectric device be prepared by easy solution processing method.Cause
This, which is a kind of organic photoelectric functional material with important application prospect.
Description of the drawings
Fig. 1 is ultra-violet absorption spectrum and fluorescence emission spectrum of the condensed-nuclei aromatics compound of gained under solution state.
Specific embodiment
The present invention is a kind of condensed-nuclei aromatics compound, which has carries out ring using three and indenes as core, to substituted aryl
The condensed-nuclei aromatics compound that fluidized dehydrogenation is formed, general formula structure is as shown in following formula I：
Wherein, Ar is selected from one of following group：
R is the linear or branched alkyl group of C1-C20, and * represents link site.
Below by way of several embodiments, the present invention will be further described, but embodiment do not limit the present invention cover model
It encloses.
Embodiment 1：
Target compound TrNaC1
【Reaction route】
According to reaction route, compound TrBr and 2- naphthalenylboronic acid occur under conditions of four triphenyl phosphorus palladiums make catalyst
Compound TrNa is made in Suzuki coupling reactions, and the ferric trichloride dissolved with nitromethane is slowly added dropwise under condition of ice bath and obtains
Compound TrNaC1.
Suzuki coupling reactions the specific steps are：Under the conditions of being protected from light, in microwave reaction pipes of the 10mL with magnetic stir bar,
Sequentially add compound TrBr (100mg, 0.075mmol), 2- naphthalenylboronic acids (116.7mg, 0.675mmol), tetrabutyl phosphonium bromide
Ammonium (TBAB) (14.5mg, 0.045mmol) and potassium hydroxide (KOH) (38.2mg, 0.68mmol) are dissolved in 3mL tetrahydrofurans
(THF) in, until completely dissolved, under nitrogen protective condition add in tetra-triphenylphosphine palladium ((Pd (PPh3) 4) (52.5mg,
0.045mmol), 150 DEG C of reaction 30min in microwave reactor, reduce temperature to room temperature.Reaction mixture DCM, water carry out
Organic layer is extracted, is washed with water repeatedly, merges organic layer, dried with anhydrous magnesium sulfate, filter, column layer is carried out after concentrated solvent
Analysis, obtains white solid 54mg, yield 45%.
Oxidative dehydrogenation cyclization the specific steps are：In N2Protect and be protected from light down, by six naphthalenes three and indenes (120mg,
It 0.075mmol) adds in two mouthfuls of reaction bulbs, it is for use to add in 20mL dichloromethane (DCM) bubbling.Prepare ferric trichloride/nitro first
Alkoxide system：By ferric trichloride (FeCl3) (144mg, 0.90mmol) add in the distilled nitromethane solutions of 1mL in, nitrogen
Gas bell 15min is for use.Ferric trichloride/nitromethane of preparation is added dropwise into reaction bulb with syringe.Nitrogen blistering reaction
30min.Reaction is quenched in methanol, and with dichloromethane, water carries out extraction organic phase, after deionization washing two or three times, anhydrous magnesium sulfate
It is dry, it filters, vacuum-concentrcted crude product, column chromatography purifying.Obtain faint yellow solid 85mg, yield 68%.
Embodiment 2：
Target compound TrNaC2
【Reaction route】
According to reaction route, compound TrBr and 2- naphthalenylboronic acid occur under conditions of four triphenyl phosphorus palladiums make catalyst
Compound TrNa is made in Suzuki coupling reactions, and the ferric trichloride dissolved with nitromethane is slowly added dropwise under condition of ice bath and obtains
Compound TrNaC2.
Oxidative dehydrogenation cyclization the specific steps are：In N2Protect and be protected from light down, by six naphthalenes three and indenes (120mg,
It 0.075mmol) adds in two mouthfuls of reaction bulbs, it is for use to add in 20mL dichloromethane (DCM) bubbling.Prepare ferric trichloride/nitro first
Alkoxide system：By ferric trichloride (FeCl3) (192mg, 1.20mmol) add in the distilled nitromethane solutions of 1.3mL in,
Nitrogen bubbling 15min is for use.Ferric trichloride/nitromethane of preparation is added dropwise into reaction bulb with syringe.Nitrogen bubbling is anti-
Answer 30min.Reaction is quenched in methanol, and with dichloromethane, water carries out extraction organic phase, after deionization washing two or three times, anhydrous slufuric acid
Magnesium is dried, and is filtered, vacuum-concentrcted crude product, column chromatography purifying.Obtain faint yellow solid 6mg, yield 5%.
Embodiment 3：
Target compound TrNaC3
【Reaction route】
According to reaction route, compound TrBr and 2- naphthalenylboronic acid occur under conditions of four triphenyl phosphorus palladiums make catalyst
Compound TrNa is made in Suzuki coupling reactions, and the ferric trichloride dissolved with nitromethane is slowly added dropwise under condition of ice bath and obtains
Compound TrNaC3.
Oxidative dehydrogenation cyclization the specific steps are：In N2Protect and be protected from light down, by six naphthalenes three and indenes (120mg,
It 0.075mmol) adds in two mouthfuls of reaction bulbs, it is for use to add in 20mL dichloromethane (DCM) bubbling.Prepare ferric trichloride/nitro first
Alkoxide system：By ferric trichloride (FeCl3) (240mg, 1.50mmol) add in the distilled nitromethane solutions of 1.6mL in,
Nitrogen bubbling 15min is for use.Ferric trichloride/nitromethane of preparation is added dropwise into reaction bulb with syringe.Nitrogen bubbling is anti-
Answer 30min.Reaction is quenched in methanol, and with dichloromethane, water carries out extraction organic phase, after deionization washing two or three times, anhydrous slufuric acid
Magnesium is dried, and is filtered, vacuum-concentrcted crude product, column chromatography purifying.Obtain faint yellow solid 9.6mg, yield 8%.
Embodiment 4：
Target compound TrNaC4
【Reaction route】
According to reaction route, compound TrBr and 2- naphthalenylboronic acid occur under conditions of four triphenyl phosphorus palladiums make catalyst
Compound TrNa is made in Suzuki coupling reactions, and the ferric trichloride dissolved with nitromethane is slowly added dropwise under condition of ice bath and obtains
Compound TrNaC4.
Oxidative dehydrogenation cyclization the specific steps are：In N2Protect and be protected from light down, by six naphthalenes three and indenes (120mg,
It 0.075mmol) adds in two mouthfuls of reaction bulbs, it is for use to add in 20mL dichloromethane (DCM) bubbling.Prepare ferric trichloride/nitro first
Alkoxide system：By ferric trichloride (FeCl3) (288mg, 1.80mmol) add in the distilled nitromethane solutions of 2mL in, nitrogen
Gas bell 15min is for use.Ferric trichloride/nitromethane of preparation is added dropwise into reaction bulb with syringe.Nitrogen blistering reaction
30min.Reaction is quenched in methanol, and with dichloromethane, water carries out extraction organic phase, after deionization washing two or three times, anhydrous magnesium sulfate
It is dry, it filters, vacuum-concentrcted crude product, column chromatography purifying.Obtain faint yellow solid 6.2mg, yield 5%.
Although we combine illustrative embodiment, the present invention is specifically described, those skilled in the art should
Work as understanding, it, can be in form and thin in the case where not departing from the spirit and scope of the present invention that the claims are limited
Various modifications and alterations are made on section.
Claims (8)
1. a kind of condensed-nuclei aromatics compound, which is characterized in that simultaneously indene derivative is nuclear structure to the compound using three, with such as following formula
General structure shown in I：
Wherein, Ar is selected from one of following group：
R is the linear or branched alkyl group of C1-C20, and * represents link site.
2. a kind of synthetic method of condensed-nuclei aromatics compound as described in claim 1, which is characterized in that added under inert atmosphere
Hexabromo three and indene derivative TrBr, tetrabutyl ammonium fluoride, potassium hydroxide, 2- aryl boric acids and tetra-triphenylphosphine palladium are simultaneously dissolved in molten
Gained crude product separating-purifying in 100-180 DEG C of reaction of microwave reactor, is obtained six aryl three after reaction and indenes spreads out by agent
Biology；Six aryl three of gained and indene derivative are dissolved in solvent under an inert atmosphere again, ferric trichloride/nitre is added dropwise at -10-10 DEG C
Methylmethane oxidation system is passed through nitrogen blistering reaction, and gained crude product is purified by pillar layer separation, is obtained such as reaction formula I
Shown condensed-nuclei aromatics compound.
A kind of 3. synthetic method of condensed-nuclei aromatics compound as claimed in claim 2, which is characterized in that the condensed-nuclei aromatics chemical combination
The preparation method of object specifically includes following steps：
Step 1：Hexabromo three and indenes, tetrabutyl ammonium fluoride, potassium hydroxide, 2- aryl boric acids and four triphens are added under an inert atmosphere
Base phosphine palladium is simultaneously dissolved in solvent A, in the reaction of 100-180 DEG C of microwave reactor, through being quenched, washing, extracting, drying, obtains crude product
Separating-purifying；
Step 2：Product obtained by step 1 is dissolved in solvent B, at -10-10 DEG C, ferric trichloride/nitromethane oxysome is added dropwise
System, is passed through nitrogen blistering reaction；Methanol is quenched, extracts, dry after, filter, obtain crude product, separating-purifying.
A kind of 4. synthetic method of condensed-nuclei aromatics compound as claimed in claim 3, which is characterized in that the reactant hexabromo
Three and indenes molal quantity and solvent A volume ratio be 1mmol：Mole of (2~10) mL, hexabromo three and indenes and tetra-triphenylphosphine palladium
Equivalent proportion is 1：(5~10) %.
5. a kind of synthetic method of condensed-nuclei aromatics compound as claimed in claim 3, which is characterized in that in the step 2
Solvent B is one or more of dichloromethane DCM, tetrahydrofuran THF, N,N-dimethylformamide DMF.
6. the synthetic method of a kind of condensed-nuclei aromatics compound as described in claim 3 or 5, which is characterized in that reaction step 1 is produced
The molal quantity of object is 1mmol with the volume ratio of solvent B：The molar equivalent of (5~15) mL, 1 product of reaction step and ferric trichloride
Than being 1：(4.0~9.0).
7. the synthetic method of a kind of condensed-nuclei aromatics compound as described in claim 3 or 4, which is characterized in that in the step 1
Solvent A one or more of for dichloromethane DCM, tetrahydrofuran THF or N,N-dimethylformamide DMF.
A kind of a kind of 8. application of condensed-nuclei aromatics compound in the opto-electronic device as described in claim 1, which is characterized in that institute
The compound stated is used mainly as the luminescent layer of organic electroluminescence device and the electron transfer layer of organic field effect tube
In the organic electro-optic device of structure efficient stable.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610309806.8A CN105907388B (en) | 2016-05-11 | 2016-05-11 | A kind of condensed-nuclei aromatics compound and preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610309806.8A CN105907388B (en) | 2016-05-11 | 2016-05-11 | A kind of condensed-nuclei aromatics compound and preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105907388A CN105907388A (en) | 2016-08-31 |
| CN105907388B true CN105907388B (en) | 2018-06-29 |
Family
ID=56748713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610309806.8A Active CN105907388B (en) | 2016-05-11 | 2016-05-11 | A kind of condensed-nuclei aromatics compound and preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105907388B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110002935A (en) * | 2018-04-10 | 2019-07-12 | 南京大学 | A kind of preparation method of large size condensed-nuclei aromatics |
| CN113638050B (en) * | 2021-06-23 | 2022-08-30 | 南京邮电大学 | Organic semiconductor single crystal and preparation method and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321085A (en) * | 2011-06-09 | 2012-01-18 | 大连理工大学 | Star molecule of truxene-perylene-series derivative and preparation method thereof |
| US9793490B2 (en) * | 2015-02-11 | 2017-10-17 | Feng-wen Yen | Organic optoelectronic material and use thereof |
-
2016
- 2016-05-11 CN CN201610309806.8A patent/CN105907388B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105907388A (en) | 2016-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104293349B (en) | A kind of based on benzene for the luminescent material of phenthazine unit and intermediate thereof and the organic electro-optic device prepared by this luminescent material | |
| CN103833507B (en) | A series of electroluminescent organic materials and preparation method and application | |
| He et al. | Oligomeric Phenylenevinylene with Cross Dipole Arrangement and Amorphous Morphology: Enhanced Solid‐State Luminescence Efficiency and Electroluminescence Performance | |
| CN100548984C (en) | A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material | |
| CN105175691B (en) | Conjugated polymer semi-conducting material, preparation and its high-efficiency polymer solar cell application of the one kind based on thieno (hetero) aryl indole unit | |
| He et al. | Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes | |
| CN106566533A (en) | Condensed ring oxidized thiophene-based organic luminescent material, and preparation method and application thereof | |
| CN103374040A (en) | Alcohol soluble cathode buffer layer molecular material containing triaryl phosphonium oxygen and nitrogen heterocyclic functional groups as well as synthetic method and application thereof | |
| CN108424344A (en) | Monomer and polymer containing luxuriant and rich with fragrance five yuan and ring element and the preparation method and application thereof | |
| CN105907388B (en) | A kind of condensed-nuclei aromatics compound and preparation method and application | |
| EP2530085A1 (en) | Heterocycloquinoid thiophene organic photoelectric material, preparation method and use thereof | |
| CN109761877A (en) | A kind of organic compound and its organic electroluminescence device using the compound | |
| CN102295758A (en) | Conjugated fractured hyperbranched polymer semiconductor photoelectric material, preparation method thereof, and application method thereof | |
| CN104693161A (en) | (S)-/(R)-difurodinaphthalene as well as derivatives thereof and preparation method | |
| CN106967056A (en) | The new solution processable 9 of one class, the preparation of 9- diaryl fluorene small molecule emitter materials and photoelectric device | |
| CN115322215B (en) | Synthesis method of silicon-containing electron transport material | |
| CN108586483B (en) | Oligomeric thiophene derivative taking S, S-dioxo dibenzothiophene as electron-accepting unit and preparation method thereof | |
| CN115260249B (en) | Composition, preparation, organic electroluminescent device and display or lighting device | |
| CN102863391B (en) | Compound containing 4-N-substituted phenyl-benzimidazole and preparation method thereof | |
| CN105949205A (en) | Nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as preparation method and application thereof | |
| CN109734648A (en) | Organic electroluminescence device compound and its organic electroluminescence device for using the compound | |
| CN112876658A (en) | Dithienopyrrole-based polymer and preparation method and application thereof | |
| CN1876753A (en) | An fluorene analogue electroluminescent material and its synthesis method thereof | |
| CN111848328A (en) | Multi-arm monomolecular white light material and preparation method and application thereof | |
| CN104861959B (en) | Aryl Methylidene-malononitrile-* Base class solid luminescent material and method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |