CN101172963A - Compound for organic luminescent material and method for producing the same - Google Patents
Compound for organic luminescent material and method for producing the same Download PDFInfo
- Publication number
- CN101172963A CN101172963A CNA2006101179832A CN200610117983A CN101172963A CN 101172963 A CN101172963 A CN 101172963A CN A2006101179832 A CNA2006101179832 A CN A2006101179832A CN 200610117983 A CN200610117983 A CN 200610117983A CN 101172963 A CN101172963 A CN 101172963A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- carbazole
- compound
- substituted
- phenyl
- 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.)
- Pending
Links
Landscapes
- Indole Compounds (AREA)
Abstract
The invention relates to a compound for organic luminous material, and comprises a structure of carbazole derivative substituted by arylamines. The compound has quite high glass transition temperature, and Tg ranges from 120 to 200 DEG C; and the thermal decomposition temperature is also quite high, and Td is higher than 450 DEG C. The invention has good carrier transport performance, and the luminous wavelength changes from green light to blue light, ranging from 400 to 560nm.
Description
Technical field
The invention belongs to technical field of organic luminescence materials, relate to electroluminescent organic material that contains the substituted carbazole base and preparation method thereof.
Background technology
Organic light emitting display (be Organic Light Emitting Display, be called for short OLED), it belongs to the kind of new emergence on mobile phone screen, MP3, MP4 screen, be described as " dreamlike indicating meter ".The OLED technique of display is different with traditional LCD display mode, need not backlight, adopts extremely thin coating of organic material and glass substrate, when electric current passed through, these organic materialss will be luminous, so the OLED screen can be done lighter and thinnerly, visible angle is bigger, and can significantly save electric energy.
The OLED material has the following disadvantages at present:
1. second-order transition temperature is low;
2. heat decomposition temperature is low;
3. the carrier transmission performance difference causes luminescent properties to reduce;
Generally the ideal amorphous membrance needs high second-order transition temperature Tg, thereby the easy crystallization of material of low Tg causes the device luminescent lifetime to reduce.And in material, introduced second-order transition temperature and the thermostability that carbazole compound can improve organic compound greatly, and many aromatic amine compounds also are class luminescent material and hole mobile materials preferably, therefore, can have the carbazole compound of thermally-stabilised and form stable as core material by utilization, it is linked to each other with many aromatic amine compounds, and these materials have dual-use function: have higher second-order transition temperature and carrier transmission performance preferably simultaneously.
Summary of the invention
Problem at present OLED material existence, low such as second-order transition temperature, decomposition temperature is low or the like, the object of the present invention is to provide a kind of very high second-order transition temperature (Tg that has, 120-200 ℃), very high heat decomposition temperature (Td＞450 ℃), carrier transmission performance preferably, the carbazole derivative that the aryl amine that the scope of emission wavelength changes from the green glow to the blue light replaces, it can be used as the luminescent material of electroluminescent device, can also be as hole mobile material.
1, a kind of carbazole derivative of arylamine replacement can be as luminescent material or the hole mobile material of OLED, the following expression of its general structure:
Wherein R is selected from: C
1-C
14Alkyl, phenyl, C
1-C
14Alkyl-substituted phenyl, C
1-C
14Alkoxy substituted phenyl, benzene cyano group, C
1-C
14Alkyl substituted benzene cyano group; Wherein preferable methyl, ethyl, phenyl, tolyl, p-methoxy-phenyl, benzene cyano group; Ar is selected from: alkyl-substituted naphthaline base, naphthyl, alkyl substituted carbazole, carbazole, alkyl replace fluorenyl, fluorenyl, alkyl replacement pyrenyl, pyrenyl; Wherein preferred naphthyl, pyrenyl, 9,9 '-diethyl fluorenyl.
2, the preparation process of the carbazole derivative of above-mentioned aryl amine replacement as shown in Figure 1: (ratio of reagents is represented with molfraction)
(1) preparation of N-substituted carbazole derivative:
With carbazole (1mol part), sodium tert-butoxide (1-3mol part), tertiary butyl phosphine (0.02-0.04mol part), organic bromo-derivative (1mol part), palladium catalyst (0.005-0.01mol part) adds exsiccant and is full of in the nitrogen reaction system, add dimethylbenzene (10mol part), be heated to 100-120 ℃, fully stirring reaction 2-3 hour; Be cooled to room temperature, add an amount of dimethylbenzene (10-30mol part) dilution, water thorough washing organic layer, layering, anhydrous magnesium sulfate drying filters, and concentrating under reduced pressure gets product;
(2) N-replaces-3, the preparation of 6-dibromo carbazole derivative:
N-bromo-succinimide NBS (2.2mol part), N ' dinethylformamide (10-30mol part), N-substituted carbazole derivative (1mol part) are added in the reactor, and logical nitrogen protection was stirred room temperature reaction three hours; Aftertreatment: the sodium chloride solution washing reaction liquid with 5%, separatory, anhydrous magnesium sulfate drying filters, and concentrating under reduced pressure gets product;
(3) preparation of diaryl-amine substituted carbazole derivative:
Corresponding N-replacement-3,6-dibromo carbazole derivative (1mol part), secondary amine (2mol part), two (dibenzalacetone acid) palladium (Pd (dba)
2) (0.005-0.01mol part), tertiary butyl phosphine (0.02-0.04mol part), sodium tert-butoxide (1-3mol part), toluene (10mol part) mixes and be heated to 80 ℃, logical nitrogen protective reaction 4-6 hour; The cancellation of reaction water, standing demix, organic layer adds ether (20mol part), washes anhydrous magnesium sulfate drying with 5% sodium chloride solution; Underpressure distillation removes to desolvate and obtains yellow solid; As eluent, silica gel separates the product of purification with column chromatography as absorption with methylene dichloride/normal hexane.
Organic bromo-derivative described in the step 1 comprises bromo alkane, bromobenzene, substituted phenyl-bromide, preferred monobromethane, bromobenzene, cyano group bromobenzene, toluene bromide, methoxyl group bromobenzene.
Palladium catalyst described in the step 1 comprises Palladous chloride, palladium.
The general formula of the secondary amine described in the step 3 is Ph-NH-Ar, and wherein Ar is selected from C
1-C
14Alkyl, phenyl, C
1-C
14Alkyl-substituted phenyl, C
1-C
14Alkoxy substituted phenyl, benzene cyano group, C
1-C
14Alkyl substituted benzene cyano group; Preferred naphthyl, pyrenyl, 9,9 '-diethyl fluorenyl.
3, the invention has the advantages that: prepared carbazole compound has very high second-order transition temperature (Tg, 120-200 ℃); Very high heat decomposition temperature (Td＞450 ℃), carrier transmission performance preferably, the scope of emission wavelength changes (400-560nm) from the green glow to the blue light.
Description of drawings
Fig. 1 is a chemical reaction process synoptic diagram of the present invention
Embodiment
Unless particular case, all reactions all need nitrogen protection, toluene must distill with sodium Metal 99.5, and methylene dichloride must distill in the presence of hydrolith and nitrogen.The way of all chromatographic separation must be separated purification with 60 purpose silica gel.
Product performance test event and testing tool: Tg is recorded by the CRY-lP differential thermal analyzer, and absorption spectrum is measured by Hitachi 330 ultraviolet-visible absorption spectroscopy instrument; Fluorescence spectrum and fluorescence quantum yield are by HitachiF-4500 type fluorescent spectrophotometer assay.
Embodiment 1
(1) preparation of N-substituted carbazole:
With carbazole (1mmol, 0.167g), sodium tert-butoxide (1mmol, 0.96g), tertiary butyl phosphine (0.02mmol, 0.0011g), monobromethane (1mmol, 0.11g), Pd (dba)
2, (0.005mmol 0.0028g) adds exsiccant and is full of in the middle of the nitrogen reaction system, adds 30ml dimethylbenzene, is heated to 100-120 ℃, fully stirring reaction 2-3 hour.Be cooled to room temperature, add an amount of dimethylbenzene dilution, water thorough washing organic layer, layering, anhydrous magnesium sulfate drying filters, and concentrating under reduced pressure gets product.
(2) preparation of N-replacement-3.6-dibromo carbazole:
(2mmol, 0.356g), (10mmol, 0.73g), (1mmol 0.195g) adds in the reactor room temperature reaction three hours to the N-substituted carbazole to N ' dinethylformamide with NBS.Aftertreatment: with salt solution washing reaction liquid, separatory, anhydrous magnesium sulfate drying filters, and concentrating under reduced pressure gets product.
(3) preparation of carbazole diamines:
Corresponding N-replacement-3,6-dibromo carbazole (1.0mmol, 0.353g), phenyl naphthyl amines (2.0mmol, 0.44g), Pd (dba) 2 (0.022g, 0.04mmol), tertiary butyl phosphine (0.008g, 0.04mmol), (0.288g 3.0mmol), toluene (20ml) mixes and be heated to 80 ℃, reacted 4-6 hour sodium tert-butoxide.Reaction is gone out with the 30ml shrend, and organic layer adds the 100ml ether, with salt washing, anhydrous magnesium sulfate drying.Underpressure distillation removes to desolvate and obtains yellow solid.As eluent, silica gel separates purification as absorption with column chromatography with methylene dichloride/normal hexane.Obtain compound 1, structural formula and physico-chemical parameter are as follows:
9-ethyl-N, N '-dinaphthyl-N, N '-phenylbenzene-3,6-two amido carbazoles (1):
Second-order transition temperature: 120 ℃; Absorption spectrum λ max=351nm;
Fluorescence spectrum λ max=497nm; Solution fluorescence quantum yield Φ=0.05;
Embodiment 2
Other operation as embodiment 1 is constant, and the monobromethane that uses in the step (1) replaces with bromobenzene, during 70 ℃ of temperature of reaction, obtains compound (2), and its structural formula and physico-chemical parameter are as follows:
9-phenyl-N, N '-dinaphthyl-N, N '-phenylbenzene-3,6-two amido carbazoles (2)
Second-order transition temperature: 123 ℃; Absorption spectrum λ max=351nm;
Fluorescence spectrum λ max=487nm; Solution fluorescence quantum yield Φ=0.07
Embodiment 3
Other operation as embodiment 1 is constant, the phenyl naphthyl amines of using in the step (3) replace with the pyrenyl phenyl amine (0.586g, 2.0mmol), temperature of reaction obtains compound (3) for 90 ℃, structural formula and physico-chemical parameter are as follows:
9-ethyl-N, N '-two pyrenyls-N, N '-phenylbenzene-3,6-two amido carbazoles (3)
Second-order transition temperature: 174 ℃; Absorption spectrum λ max=408nm;
Fluorescence spectrum λ max=548nm; Solution fluorescence quantum yield Φ=0.03
Embodiment 4
Other operation as embodiment 1 is constant, the monobromethane that uses in the step (1) replaces with bromobenzene, the phenyl naphthyl amines that step (3) is used replace with the pyrenyl phenyl amine (2.0mmol, 0.59g), temperature of reaction obtains compound (4) for 90 ℃, and structural formula and physico-chemical parameter are as follows:
9-phenyl-N, N '-two pyrenyls-N, N '-phenylbenzene-3,6-two amido carbazoles (4)
Wherein the significant parameter of (4) is as follows:
Second-order transition temperature: 180 ℃; Absorption spectrum λ max=408nm;
Fluorescence spectrum λ max=539nm; Solution fluorescence quantum yield Φ=0.12
Embodiment 5
Other operation as embodiment 1 is constant, the monobromethane that uses in the step (1) replaces with 4-cyano group bromobenzene, the phenyl naphthyl amines that step (3) is used replace with the pyrenyl phenyl amine (2.0mmol, 0.59g), temperature of reaction obtains compound (5) for 90 ℃, and structural formula and physico-chemical parameter are as follows:
9-is to benzonitrile base-N, N '-two pyrenyls-N, N '-phenylbenzene-3,6-two amido carbazoles (5)
Second-order transition temperature: 194 ℃; Absorption spectrum λ max=385nm;
Fluorescence spectrum λ max=515nm; Solution fluorescence quantum yield Φ=0.18
Embodiment 6
Other operation as embodiment 1 is constant, the monobromethane that uses in the step (1) replaces with 4-cyano group bromobenzene, the naphthyl phenyl secondary amine that step (3) is used replaces with 9,9 '-diethyl fluorenyl phenyl secondary amine (2.0mmol, 0.63g), temperature of reaction obtains compound (6) for 90 ℃, and structural formula and physico-chemical parameter are as follows:
9-phenyl-N, N '-two (9,9 ' diethyl fluorenyl)-N, N '-phenylbenzene-3,6-two amido carbazoles (6)
Second-order transition temperature: 132 ℃; Absorption spectrum λ max=352nm;
Fluorescence spectrum λ max=439nm; Solution fluorescence quantum yield Φ=0.08
Embodiment 7
Other operation as embodiment 1 is constant, the monobromethane that uses in the step (1) replaces with 4-methyl bromobenzene, the phenyl naphthyl amines that step (3) is used replace with as the pyrenyl phenyl amine (2.0mmol, 0.59g), temperature of reaction obtains compound (7) for 90 ℃, and structural formula and physico-chemical parameter are as follows:
9-p-methylphenyl-N, N '-two pyrenyls-N, N '-phenylbenzene-3,6-two amido carbazoles (7)
Second-order transition temperature: 184 ℃; Absorption spectrum λ max=420nm;
Fluorescence spectrum λ max=543nm; Solution fluorescence quantum yield Φ=0.11
Embodiment 8
Other operation as embodiment 1 is constant, the monobromethane that uses in the step (1) replaces with 4-methoxyl group bromobenzene, the phenyl naphthyl amines that step (3) is used replace with as the pyrenyl phenyl amine (2.0mmol, 0.59g), temperature of reaction obtains compound (7) for 90 ℃, and structural formula and physico-chemical parameter are as follows:
9-p-methoxyphenyl-N, N '-two pyrenyls-N, N '-phenylbenzene-3,6-two amido carbazoles (8)
Second-order transition temperature: 183 ℃; Absorption spectrum λ max=424nm;
Fluorescence spectrum λ max=546nm; Solution fluorescence quantum yield Φ=0.13
The above-mentioned description to embodiment is can understand and apply the invention for ease of those skilled in the art.The person skilled in the art obviously can easily make various modifications to these embodiment, and needn't pass through performing creative labour being applied in the General Principle of this explanation among other embodiment.Therefore, the invention is not restricted to the embodiment here, those skilled in the art should be within protection scope of the present invention for improvement and modification that the present invention makes according to announcement of the present invention.
Claims (10)
1. a class is used for the compound of luminous organic material, it is characterized in that containing the carbazole derivant structure that arylamine replaces, and general structure is expressed as follows:
Wherein R is selected from: C
1-C
14Alkyl, phenyl, C
1-C
14Alkyl-substituted phenyl, C
1-C
14Alkoxy substituted phenyl, benzene cyano group, C
1-C
14Alkyl substituted benzene cyano group; Ar is selected from: alkyl-substituted naphthaline base, naphthyl, alkyl substituted carbazole, carbazole, alkyl replace fluorenyl, fluorenyl, alkyl replacement pyrenyl, pyrenyl.
2. compound as claimed in claim 1 is characterized in that wherein the R group is selected from methyl, ethyl, phenyl, tolyl, p-methoxy-phenyl, benzene cyano group; The Ar group is selected from naphthyl, pyrenyl, 9,9 '-diethyl fluorenyl.
3. compound as claimed in claim 1 is characterized in that molecular structure has symmetry.
4. compound as claimed in claim 1 is characterized in that second-order transition temperature is between 120-200 ℃; Heat decomposition temperature is greater than 450 ℃.
5. compound as claimed in claim 1 is characterized in that the emission wavelength scope is between 400-560nm.
6. the preparation process of the described compound of claim 1-5, the molfraction of concrete steps and reagent is as follows:
(1) preparation of N-substituted carbazole derivative:
With 1 part of carbazole, 1-3 part sodium tert-butoxide, 0.020-0.04 part tertiary butyl phosphine, 1 part of organic bromo-derivative, 0.005-0.01 adding exsiccant, part palladium catalyst is full of in the nitrogen reaction system, add 10 parts of dimethylbenzene, be heated to 100-120 ℃, fully stirring reaction 2-3 hour; Be cooled to room temperature, add the dilution of 10-30 part dimethylbenzene, water thorough washing organic layer, layering, drying is filtered, and concentrating under reduced pressure gets product;
(2) N-replaces-3, the preparation of 6-dibromo carbazole derivative:
2.2 parts of N-bromo-succinimides, 10-30 part N ' dinethylformamide, 1 part of N-substituted carbazole derivative are added in the reactor, and logical nitrogen protection was stirred room temperature reaction three hours; Sodium chloride solution washing reaction liquid with 5%, separatory, drying is filtered, and concentrating under reduced pressure gets product;
(3) preparation of diaryl-amine substituted carbazole derivative:
Corresponding 1 part of N-replaces-3,6-dibromo carbazole derivative, 2 parts of secondary amine, two (dibenzalacetone acid) the palladium Pd (dba) of 0.005-0.01 part
2, 0.02-0.04 part tertiary butyl phosphine, 1-3 part sodium tert-butoxide, 10 parts of toluene mixes and be heated to 80 ℃, logical nitrogen protective reaction 4-6 hour; The cancellation of reaction water, standing demix, organic layer adds 20 parts of ether, washes drying with 5% sodium chloride solution; Removing desolvates obtains yellow solid.
7. preparation method as claimed in claim 6 is characterized in that the organic bromo-derivative described in the step 1 comprises bromo alkane, bromobenzene, substituted phenyl-bromide, preferred monobromethane, bromobenzene, cyano group bromobenzene, toluene bromide, methoxyl group bromobenzene.
8. preparation method as claimed in claim 6 is characterized in that the palladium catalyst described in the step 1 comprises Palladous chloride, palladium.
9. preparation method as claimed in claim 6, the general formula that it is characterized in that the secondary amine described in the step 3 is Ph-NH-Ar, and wherein Ar is selected from alkyl-substituted naphthaline base, naphthyl, alkyl substituted carbazole, carbazole, alkyl replacement fluorenyl, fluorenyl, alkyl replacement pyrenyl, pyrenyl; Preferred naphthyl, pyrenyl, 9,9 '-diethyl fluorenyl.
10. organic electroluminescent or hole mobile material wherein contain described compound of 50wt% claim 1-4 and derivative thereof at least.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101179832A CN101172963A (en) | 2006-11-03 | 2006-11-03 | Compound for organic luminescent material and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101179832A CN101172963A (en) | 2006-11-03 | 2006-11-03 | Compound for organic luminescent material and method for producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101172963A true CN101172963A (en) | 2008-05-07 |
Family
ID=39421741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006101179832A Pending CN101172963A (en) | 2006-11-03 | 2006-11-03 | Compound for organic luminescent material and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101172963A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011176259A (en) * | 2009-06-03 | 2011-09-08 | Fujifilm Corp | Photoelectric conversion device and imaging device |
| CN102875447A (en) * | 2012-03-06 | 2013-01-16 | 河南省科学院化学研究所有限公司 | Method for preparing 2,7-dibromocarbazole |
| CN103183638A (en) * | 2011-12-31 | 2013-07-03 | 昆山维信诺显示技术有限公司 | Compounds, preparation methods thereof and organic electroluminescent device comprising same |
| CN103570620A (en) * | 2011-12-29 | 2014-02-12 | 昆山维信诺显示技术有限公司 | 1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound |
| CN103956436A (en) * | 2014-05-09 | 2014-07-30 | 江西冠能光电材料有限公司 | Organic semiconductor hole transport material |
| CN104650067A (en) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | Green material, preparation method and application thereof |
| CN109734607A (en) * | 2018-11-29 | 2019-05-10 | 宇瑞(上海)化学有限公司 | A kind of organic compound and its organic electroluminescence device and organic luminescent device |
| CN110041209A (en) * | 2019-05-08 | 2019-07-23 | 北京诚志永华显示科技有限公司 | A kind of aromatic amine compounds, material and organic electroluminescence device comprising the aromatic amine compounds |
-
2006
- 2006-11-03 CN CNA2006101179832A patent/CN101172963A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011176259A (en) * | 2009-06-03 | 2011-09-08 | Fujifilm Corp | Photoelectric conversion device and imaging device |
| CN103570620A (en) * | 2011-12-29 | 2014-02-12 | 昆山维信诺显示技术有限公司 | 1,12-iminobenzo[c]phenanthrene compound, intermediate, preparation method and application of compound |
| CN103570620B (en) * | 2011-12-29 | 2016-06-15 | 昆山维信诺显示技术有限公司 | The luxuriant and rich with fragrance compounds of a kind of 1,12-imino group benzo [c], intermediate and preparation method and application |
| CN103183638A (en) * | 2011-12-31 | 2013-07-03 | 昆山维信诺显示技术有限公司 | Compounds, preparation methods thereof and organic electroluminescent device comprising same |
| CN103183638B (en) * | 2011-12-31 | 2015-09-02 | 昆山维信诺显示技术有限公司 | One compounds, its method for making and the organic electroluminescence device containing it |
| CN102875447A (en) * | 2012-03-06 | 2013-01-16 | 河南省科学院化学研究所有限公司 | Method for preparing 2,7-dibromocarbazole |
| CN102875447B (en) * | 2012-03-06 | 2014-03-26 | 河南省科学院化学研究所有限公司 | Method for preparing 2,7-dibromocarbazole |
| CN103956436A (en) * | 2014-05-09 | 2014-07-30 | 江西冠能光电材料有限公司 | Organic semiconductor hole transport material |
| CN104650067A (en) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | Green material, preparation method and application thereof |
| CN104650067B (en) * | 2014-08-05 | 2017-11-21 | 吉林奥来德光电材料股份有限公司 | A kind of green light material and its preparation method and application |
| CN109734607A (en) * | 2018-11-29 | 2019-05-10 | 宇瑞(上海)化学有限公司 | A kind of organic compound and its organic electroluminescence device and organic luminescent device |
| CN110041209A (en) * | 2019-05-08 | 2019-07-23 | 北京诚志永华显示科技有限公司 | A kind of aromatic amine compounds, material and organic electroluminescence device comprising the aromatic amine compounds |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101172963A (en) | Compound for organic luminescent material and method for producing the same | |
| CN104498025B (en) | Many phenyl benzene constructs cyano-containing light emitting molecule and its production and use | |
| CN101410356B (en) | Novel compound and organic light emitting device using the compound | |
| He et al. | Visible-light excitable europium (III) complexes with 2, 7-positional substituted carbazole group-containing ligands | |
| CN103193733B (en) | 2,7-di-(N-phenothiazinyl)fluorenone and preparation method thereof | |
| CN102428159A (en) | Chrysene Compounds For Luminescent Applications | |
| CN108865117A (en) | Aggregation-induced emission organic fluorescence small molecule material and its application in DNT and TNT gas fluorescence detection | |
| CN103242298A (en) | 1,2,4-triazole derivative, preparation method and application thereof and organic electroluminescent device | |
| Vaz et al. | Aggregation-induced emission enhancement in halochalcones | |
| Feng et al. | Imine organic cages derived from tetraphenylethylene dialdehydes exhibiting aggregation-induced emission and explosives detection | |
| CN109369660A (en) | Luminous organic material and its preparation method and organic electroluminescence device containing the material | |
| Lao et al. | Palladium‐Catalyzed Cascade Reaction in Water to Imidazo [1, 2‐a] pyridazines as Switchable DSEgens, AIEgens, and ACQgens | |
| CN102295743A (en) | Fluorescent conjugated polymer containing polyhedral oligomeric silsesquioxane (POSS), its preparation method and application | |
| Gayathri et al. | Naphthylacetonitrile isomerism and donor conformational flexibility controlled molecular self-assembly and solid-state fluorescence properties | |
| CN103242358B (en) | Siliceous dianthranide derivative and its preparation method and application and organic electroluminescence device | |
| CN107868038A (en) | One kind contains organic compound and its application of the fluorenes of 9,9 ' spiral shell two | |
| CN111808097B (en) | Solvent yellow 184 derivative and preparation method and application thereof | |
| CN111039930A (en) | bis-N-phenyl-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device | |
| CN110330532A (en) | A kind of novel phosphorescent iridium complex and the preparation method and application thereof | |
| CN106749076A (en) | O-hydroxy-phenyl azole derivative as organic blue light material application | |
| CN109369598A (en) | A kind of luminous organic material and preparation method and the organic luminescent device containing the material | |
| CN110872303B (en) | Compound containing spiro acridine structure and application thereof | |
| CN110862420B (en) | Energy transfer luminescent material based on triplet donor material and acceptor material and application thereof | |
| CN107163071A (en) | Boron N doping guan class compounds and preparation method thereof | |
| CN113201022A (en) | Small conjugated phosphorescent metal iridium (III) complex with isomer and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20090220 Address after: 6, Da Long Road, Shigu village, Nancheng District, Guangdong City, Dongguan Province, China: 523081 Applicant after: Dongguan Hongwei Digital Machinery Co., Ltd. Address before: Room nine, building 100, Shanghai Normal University, No. 319, Shanghai, Guilin Road, China: 200234 Applicant before: Tuoyin Digit Technology Co., Ltd., Shanghai |
|
| ASS | Succession or assignment of patent right |
Owner name: DONGGUAN HONGWEI DIGITAL MACHINE CO., LTD. Free format text: FORMER OWNER: SHANGHAI TUOYIN DIGITAL TECHNOLOGY CO., LTD. Effective date: 20090220 |
|
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Open date: 20080507 |