CN110330472A - A kind of blue light material and its preparation method and application - Google Patents
A kind of blue light material and its preparation method and application Download PDFInfo
- Publication number
- CN110330472A CN110330472A CN201910619453.5A CN201910619453A CN110330472A CN 110330472 A CN110330472 A CN 110330472A CN 201910619453 A CN201910619453 A CN 201910619453A CN 110330472 A CN110330472 A CN 110330472A
- Authority
- CN
- China
- Prior art keywords
- blue light
- light material
- compound
- layer
- substituted
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/626—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
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
-
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a kind of blue light material and its preparation method and application, the structural formula of the blue light material as described in chemical formula 1:The preparation method of blue light material of the invention is the following steps are included: by compound A, compound B-a or compound B-b or compound B-c and K2CO3It is placed in reaction vessel, nitrogen displacement reaction flask；THF and H is added under nitrogen atmosphere2O is uniformly mixed, nitrogen displacement reaction flask；Pd (pph is added under nitrogen atmosphere3)4, nitrogen displacement reaction flask；System is down to room temperature after reaction, solid will be precipitated and filter, THF elutes solid, obtains compound shown in chemical formula 1.Blue light material provided by the invention has the advantages that luminous efficiency is high, good film-forming property, thermal stability is good.Compared with conventional blue material of main part, which has the characteristics that the device light emitting efficiency height of preparation and service life are long.The features such as preparation method of blue light material provided by the invention has synthesis step simple, and condition requirement is not harsh, and target product yield is high.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, and in particular to a kind of blue light material and preparation method thereof and answers
With.
Background technique
Early in the 1960s, people have found that organic electroluminescent phenomenon.1963, New York Univ USA
Pope et al. has found in the Crystal study to organic aromatic series anthracene, when applying hundreds of volt voltages on anthracene crystal, can be observed
Crystal has faint blue emission phenomenon, opens the road to photoelectric material research and development with regard to this.But due to the driving voltage of needs
Excessively high, the very low reason of luminous efficiency, the discovery fails to draw attention.1987, doctor Deng Qingyun reported based on organic
The electroluminescent diode technology of luminescent material is prepared mainly using vacuum evaporation by the way of with transport layer and luminescent layer
Bi-layer devices, quantum efficiency are improved to 1%, can reach 1000cd/m under the operating voltage lower than 10V2Brightness, cause
The extensive concern of World Science fan, the paces for pushing organic electroluminescent technology to stride forward to practical stage.
With the continuous development of organic electroluminescent LED technology, organic electroluminescence device (Organic Light-
Emitting Diodes, abbreviation OLEDs) by self-luminous, shine visual angle is wide, frivolous, driving voltage is low, fast response time, can
The advantages such as bending fold show in information and lighting area are used widely.Luminescent layer is as important composition portion in OLEDs
Point, it is made of three kinds of electroluminescent organic materials of red, green, blue, in these luminescent materials, blue light material is particularly important, because
Blue light needed for it not only can provide illumination, display can also obtain feux rouges and green light by energy transfer.Blue light material
Although the electroluminescent organic material being found earliest, because it has wider energy gap, it is difficult to provide at low voltage higher
Luminous efficiency, so limiting its application.And the various aspects of performance of existing red light material and green light material can meet rule
Modelling production requirement and application.It is led so finding the blue-ray organic electroluminescent material high performance, stability is good as OLEDs
The key points and difficulties of domain acquirement important breakthrough.
Summary of the invention
The object of the present invention is to provide a kind of new structural blue light material and its preparation method and application, indigo plants of the invention
Luminescent material has the advantages that luminous efficiency is high, good film-forming property, thermal stability is good.
To achieve the goals above, technical solution of the present invention is specific as follows:
The present invention provides a kind of blue light material, structural formula as described in chemical formula 1:
Wherein:
R1For C1-C60 alkyl, C6-C60 aryl, C3-C30 naphthenic base or C3-C30 heteroaryl；
Any one of Ar in Ar1~Ar3 in following general formula:
In Ar1~Ar3:
R2~R5Hydrogen is each independently represented, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, is substituted or is unsubstituted
C1-C30 alkyl, the C2-C30 alkenyl for being substituted or being unsubstituted, the C6-C30 aryl for being substituted or being unsubstituted, be substituted or
The C3-C30 heteroaryl that is unsubstituted, the C1-C30 oxyalkyl for being substituted or being unsubstituted, the C3- for being substituted or being unsubstituted
C30 naphthenic base, the C3-C30 cycloalkenyl for being substituted or being unsubstituted or the C3-C30 Heterocyclylalkyl for being substituted or being unsubstituted；
Or it is connect with adjacent substituents and to form monocycle or aliphatic ring or aromatic ring polycyclic, that be specially C3-C30；
A and c respectively independently represents number 0 to 3；
B represents number 0 to 4；
D represents number 0 to 2；
X indicates O or S；
G ring indicates the C6-C60 aryl for being substituted or being unsubstituted or the C6-C60 heteroaryl for being substituted or being unsubstituted.
In the above-mentioned technical solutions, work as R2~R5It connect to form monocycle or polycyclic, specially C3-C30 with adjacent substituents
Aliphatic ring or aromatic ring, carbon atom are replaced by least one nitrogen, oxygen or sulphur atom.
In the above-mentioned technical solutions, R1For phenyl or how base.
In the above-mentioned technical solutions, any one of Ar in such as flowering structure:
In the above-mentioned technical solutions, the blue light material is selected from any one in flowering structure:
The present invention also provides a kind of preparation methods of blue light material, comprising the following steps:
By compound A, compound B-a or compound B-b or compound B-c and K2CO3It is placed in reaction vessel, nitrogen
Gas displacement reaction flask；THF and H is added under nitrogen atmosphere2O is uniformly mixed, nitrogen displacement reaction flask；Add under nitrogen atmosphere
Enter Pd (pph3)4, nitrogen displacement reaction flask；System is down to room temperature after reaction, solid will be precipitated and filter, THF elution is solid
Body obtains compound shown in chemical formula 1；
Synthetic route is as follows:
Or:
Or:
Wherein, Hal represents halogen；E representative-B (OH)2；R1~R5, range represented by a, b, c, d, X and G ring with it is upper
The range for stating the restriction of chemical formula 1 is identical, and which is not described herein again.
The present invention also provides the application of above-mentioned blue light material, the blue light material is used to prepare organic electroluminescence device.
The organic electroluminescence device includes: first electrode, second electrode and the organic matter layer being placed between two electrodes,
Its organic matter layer includes compound described in chemical formula 1；1 compound represented of chemical formula is single form or and other materials
It is mixed in organic matter layer.
The organic matter layer includes hole injection layer, hole transmission layer, hole blocking layer, luminescent layer, electronic barrier layer, electricity
At least one layer in sub- transport layer and electron injecting layer.It is wherein at least one layer of in organic matter layer to include chemical combination shown in chemical formula 1
Object.
Wherein at least one layer of in organic matter layer includes 1 compound represented of chemical formula.
Device of the invention can be used for organic electroluminescence device, organic photovoltaic cell, Electronic Paper, Organophotoreceptor,
Or Organic Thin Film Transistors.
The beneficial effects of the present invention are:
Blue light material provided by the invention has the advantages that luminous efficiency is high, good film-forming property, thermal stability is good.With conventional indigo plant
Color material of main part is compared, which has the characteristics that the device light emitting efficiency height of preparation and service life are long.
The preparation method of blue light material provided by the invention has synthesis step simple, and condition requires not harsh, target production
The features such as object high income.
Specific embodiment
Blue light material of the present invention and preparation method thereof, specific embodiment is as follows:
Embodiment 1: the compound that preparation number is 2
Raw material A -1 (8.48g, 17.4mmol), raw material B-1 (4.07g, 19.2mmol) and carbonic acid are added in the reaction vessel
Tetrahydrofuran (95mL), water (95mL), nitrogen are added under nitrogen atmosphere for potassium (7.23g, 52.3mmol), nitrogen displacement reaction vessel
Gas metathesis reactor, stirs evenly, and tetrakis triphenylphosphine palladium (0.404g, 0.399mmol) is added under nitrogen atmosphere, anti-at 80 DEG C
It should complete, TLC monitoring reaction.Reaction generates solid and carries out decompression suction filtration.Obtained solid residue is using column chromatography method to it
It carries out purifying to obtain compound 2 (7g), yield 70%, Mass Spectrometer Method value is 572.71.
Embodiment 2: the compound that preparation number is 9
Raw material A -2 (7.79g, 16mmol), raw material B-2 (4.63g, 17.6mmol) and potassium carbonate are added in the reaction vessel
Tetrahydrofuran (90mL), water (90mL), nitrogen are added under nitrogen atmosphere for (6.64g, 48.1mmol), nitrogen displacement reaction vessel
Metathesis reactor stirs evenly, and tetrakis triphenylphosphine palladium (0.37g, 0.32mmol) is added under nitrogen atmosphere, has reacted at 80 DEG C
At TLC monitoring reaction.Reaction generates solid and carries out decompression suction filtration.Obtained solid residue carries out it using column chromatography method
Compound 9 (8.2g), yield 82% are purified to obtain, Mass Spectrometer Method value is 622.72.
Embodiment 3: the compound that preparation number is 21
Raw material A -3 (7.79g, 16mmol), raw material B-3 (4.63g, 17.6mmol) and potassium carbonate are added in the reaction vessel
Tetrahydrofuran (90mL), water (90mL), nitrogen are added under nitrogen atmosphere for (6.64g, 48.1mmol), nitrogen displacement reaction vessel
Metathesis reactor stirs evenly, and tetrakis triphenylphosphine palladium (0.37g, 0.32mmol) is added under nitrogen atmosphere, has reacted at 80 DEG C
At TLC monitoring reaction.Reaction generates solid and carries out decompression suction filtration.Obtained solid residue carries out it using column chromatography method
Compound 21 (7.5g), yield 76.5% are purified to obtain, Mass Spectrometer Method value is 622.78.
Embodiment 4: the compound that preparation number is 38
Raw material A -4 (8.48g, 17.4mmol), raw material B-4 (4.07g, 19.2mmol) and carbonic acid are added in the reaction vessel
Tetrahydrofuran (95mL), water (95mL), nitrogen are added under nitrogen atmosphere for potassium (7.23g, 52.3mmol), nitrogen displacement reaction vessel
Gas metathesis reactor, stirs evenly, and tetrakis triphenylphosphine palladium (0.404g, 0.399mmol) is added under nitrogen atmosphere, anti-at 80 DEG C
It should complete, TLC monitoring reaction.Reaction generates solid and carries out decompression suction filtration.Obtained solid residue is using column chromatography method to it
It carries out purifying to obtain compound 38 (7.8g), yield 72%, Mass Spectrometer Method value is 622.73.
Raw material B-1 in above-described embodiment 1 is replaced with respectively It is identical referring to embodiment 1
Method compound 69, compound 70, compound 71, compound 72 can be prepared respectively.
Organic electroluminescence device is manufactured using the compounds of this invention；
Embodiment 5:
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 2 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 electroluminescence as cathode with this
The preparation of part.
Embodiment 6:
Compound 2 is replaced with compound 9, and prepares organic electroluminescence device with method same as Example 5.
Embodiment 7:
Compound 2 is replaced with compound 21, and prepares organic electroluminescence device with method same as Example 5.
Embodiment 8:
Compound 2 is replaced with compound 38, and prepares organic electroluminescence device with method same as Example 5.
Comparative example 1:
With compound 9,10- is bis--(1- naphthalene) anthracene (ADN) replaces compound 2, and with method system same as Example 5
Have organic electroluminescence devices.
The Electroluminescence Properties of above-mentioned organic electroluminescence device:
Efficiency (the stream for each organic electroluminescence device that evaluation is manufactured according to embodiment 5 to embodiment 8 and comparative example 1
Density: 10mA/cm2) and service life (10mA/cm2T90 under current density).
As seen from the above table, the compound of the present invention may be used as efficient blue electroluminescent material.In addition, applied
The compound of the present invention shows significant improvement as the device of material of main part in terms of excitation purity.In service life and luminous efficiency two
The improvement of a aspect confirms that material of the invention has 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 blue light material, which is characterized in that its structural formula as described in chemical formula 1:
Wherein:
R1For C1-C60 alkyl, C6-C60 aryl, C3-C30 naphthenic base or C3-C30 heteroaryl；
Any one of Ar in Ar1~Ar3 in following general formula:
In Ar1~Ar3:
R2~R5Each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, the C1- for being substituted or being unsubstituted
C30 alkyl, the C6-C30 aryl for being substituted or being unsubstituted, is substituted or not the C2-C30 alkenyl for being substituted or being unsubstituted
The C3-C30 heteroaryl that is substituted, the C1-C30 oxyalkyl for being substituted or being unsubstituted, the C3-C30 for being substituted or being unsubstituted
Naphthenic base, the C3-C30 cycloalkenyl for being substituted or being unsubstituted or the C3-C30 Heterocyclylalkyl for being substituted or being unsubstituted；Or with
Adjacent substituents connect to form monocycle or aliphatic ring or aromatic ring polycyclic, that be specially C3-C30；
A and c respectively independently represents number 0 to 3；
B represents number 0 to 4；
D represents number 0 to 2；
X indicates O or S；
G ring indicates the C6-C60 aryl for being substituted or being unsubstituted or the C6-C60 heteroaryl for being substituted or being unsubstituted.
2. blue light material according to claim 1, which is characterized in that work as R2~R5It connect to form monocycle with adjacent substituents
Or aliphatic ring or aromatic ring polycyclic, that be specially C3-C30, carbon atom are replaced by least one nitrogen, oxygen or sulphur atom.
3. blue light material according to claim 1, which is characterized in that R1For phenyl or how base.
4. blue light material according to claim 1, which is characterized in that any one of Ar in such as flowering structure:
5. blue light material according to claim 1, which is characterized in that it is selected from any one in flowering structure:
6. a kind of preparation method of blue light material described in claim 1-5 any one, which is characterized in that including following step
It is rapid:
By compound A, compound B-a or compound B-b or compound B-c and K2CO3It is placed in reaction vessel, nitrogen is set
Change reaction flask；THF and H is added under nitrogen atmosphere2O is uniformly mixed, nitrogen displacement reaction flask；Pd is added under nitrogen atmosphere
(pph3)4, nitrogen displacement reaction flask；System is down to room temperature after reaction, solid will be precipitated and filter, THF elutes solid, obtains
Compound shown in chemical formula 1；
Synthetic route is as follows:
Or:
Or:
Wherein, Hal represents halogen；E representative-B (OH)2。
7. a kind of includes the organic electroluminescence device of blue light material described in claim 1-5 any one.
8. organic electroluminescence device according to claim 7 characterized by comprising first electrode, second electrode and
The organic matter layer being placed between two electrodes, organic matter layer include blue light material described in claim 1-5 any one；Power
Benefit requires blue light material described in 1-5 any one to be single form or be mixed in organic matter layer with other materials.
9. organic electroluminescence device according to claim 7, which is characterized in that the organic matter layer is injected comprising hole
At least one in layer, hole transmission layer, hole blocking layer, luminescent layer, electronic barrier layer, electron transfer layer and electron injecting layer
Layer.Wherein at least one layer of in organic matter layer includes 1 compound represented of chemical formula.
10. organic electroluminescence device according to claim 7, which is characterized in that for organic electroluminescence device, have
Machine solar cell, Electronic Paper, Organophotoreceptor or Organic Thin Film Transistors.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910619453.5A CN110330472B (en) | 2019-07-10 | 2019-07-10 | Blue light material and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910619453.5A CN110330472B (en) | 2019-07-10 | 2019-07-10 | Blue light material and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110330472A true CN110330472A (en) | 2019-10-15 |
| CN110330472B CN110330472B (en) | 2022-02-01 |
Family
ID=68145604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910619453.5A Active CN110330472B (en) | 2019-07-10 | 2019-07-10 | Blue light material and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110330472B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020218515A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescence element, and electronic device |
| WO2020218514A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescent element and electronic device |
| CN113149943A (en) * | 2021-05-10 | 2021-07-23 | 吉林奥来德光电材料股份有限公司 | Fluorescent compound, preparation method thereof and organic electroluminescent device comprising same |
| WO2021230653A1 (en) * | 2020-05-12 | 2021-11-18 | 에스에프씨 주식회사 | Organic light-emitting compound and organic light-emitting device comprising same |
| CN116041297A (en) * | 2022-12-30 | 2023-05-02 | 上海飞凯材料科技股份有限公司 | Host material and organic electroluminescent device |
| WO2024190824A1 (en) * | 2023-03-14 | 2024-09-19 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103554011A (en) * | 2013-10-30 | 2014-02-05 | 吉林奥来德光电材料股份有限公司 | Anthracene containing derivative as well as preparation method and application thereof |
| WO2014061963A1 (en) * | 2012-10-16 | 2014-04-24 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
| CN106206964A (en) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | Organic luminescent device |
| CN107531661A (en) * | 2015-04-23 | 2018-01-02 | Sfc株式会社 | Organic illuminating element compound and the organic illuminating element including the compound |
| KR20180127935A (en) * | 2017-05-22 | 2018-11-30 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising the same |
| CN111656548A (en) * | 2018-05-17 | 2020-09-11 | 株式会社Lg化学 | Organic light emitting device |
-
2019
- 2019-07-10 CN CN201910619453.5A patent/CN110330472B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2014061963A1 (en) * | 2012-10-16 | 2014-04-24 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
| CN103554011A (en) * | 2013-10-30 | 2014-02-05 | 吉林奥来德光电材料股份有限公司 | Anthracene containing derivative as well as preparation method and application thereof |
| CN107531661A (en) * | 2015-04-23 | 2018-01-02 | Sfc株式会社 | Organic illuminating element compound and the organic illuminating element including the compound |
| CN106206964A (en) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | Organic luminescent device |
| KR20180127935A (en) * | 2017-05-22 | 2018-11-30 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising the same |
| CN111656548A (en) * | 2018-05-17 | 2020-09-11 | 株式会社Lg化学 | Organic light emitting device |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020218515A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescence element, and electronic device |
| WO2020218514A1 (en) * | 2019-04-26 | 2020-10-29 | 出光興産株式会社 | Compound, organic electroluminescent element and electronic device |
| WO2021230653A1 (en) * | 2020-05-12 | 2021-11-18 | 에스에프씨 주식회사 | Organic light-emitting compound and organic light-emitting device comprising same |
| CN116057050A (en) * | 2020-05-12 | 2023-05-02 | Sfc株式会社 | Organic light-emitting compound and organic light-emitting device comprising the same |
| CN113149943A (en) * | 2021-05-10 | 2021-07-23 | 吉林奥来德光电材料股份有限公司 | Fluorescent compound, preparation method thereof and organic electroluminescent device comprising same |
| CN113149943B (en) * | 2021-05-10 | 2023-08-22 | 吉林奥来德光电材料股份有限公司 | Fluorescent compound, preparation method thereof and organic electroluminescent device comprising fluorescent compound |
| CN116041297A (en) * | 2022-12-30 | 2023-05-02 | 上海飞凯材料科技股份有限公司 | Host material and organic electroluminescent device |
| WO2024190824A1 (en) * | 2023-03-14 | 2024-09-19 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110330472B (en) | 2022-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112174992B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN110330472A (en) | A kind of blue light material and its preparation method and application | |
| JP5774267B2 (en) | Organic electroluminescent compound and light emitting diode using the same | |
| CN102933531A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| JP2006151866A (en) | Phenanthroline compound and light-emitting element | |
| JP7458483B2 (en) | Metal complexes and their uses | |
| CN108794404B (en) | Anthracene organic luminescent compound, preparation method thereof and organic electroluminescent device | |
| CN112375071B (en) | Organic light-emitting compound and preparation method and application thereof | |
| CN107056807B (en) | It is a kind of using equal benzene as the compound of core and its application in organic electroluminescence device | |
| CN111662190A (en) | Organic compound containing pyrene or aza-pyrene and application thereof | |
| CN107068880A (en) | A kind of organic electroluminescence device containing diaryl ketone compounds and its application | |
| CN106749050B (en) | It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application | |
| CN112079876A (en) | Organic compound and organic electroluminescent device using same | |
| CN107056763A (en) | A kind of electroluminescent organic material and its application using xanthene as core | |
| CN109054810A (en) | Using diphenylsulfide as the thermal excitation delayed fluorescence material of main part of parent and its preparation and application | |
| CN112341460A (en) | Organic compound and organic light-emitting device using same | |
| CN115073307B (en) | Fluorene compound and application thereof in organic electroluminescent device | |
| CN110642666A (en) | Blue fluorescent host compound and preparation method and device thereof | |
| CN116113294A (en) | Organic electroluminescent device and application thereof | |
| CN110105231B (en) | Compound containing azulene ring, application thereof and organic photoelectric device containing compound | |
| TWI488941B (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| CN113248522B (en) | Organic compound and organic light-emitting device using same | |
| CN113480529B (en) | Organic compound and use this organic photoelectric element of compound | |
| CN118221640B (en) | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device | |
| CN115433233B (en) | Aromatic phosphine oxide thermal excitation delayed fluorescence main body material containing spiroacridine group, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |