CN103102877B - Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material - Google Patents
Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material Download PDFInfo
- Publication number
- CN103102877B CN103102877B CN201210457333.8A CN201210457333A CN103102877B CN 103102877 B CN103102877 B CN 103102877B CN 201210457333 A CN201210457333 A CN 201210457333A CN 103102877 B CN103102877 B CN 103102877B
- Authority
- CN
- China
- Prior art keywords
- preparation
- organic material
- siliceous
- luminous organic
- bromophenyl
- 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
Abstract
The invention provides a silicon-containing organic luminescent material as well as a preparation method and an application of the organic luminescent material. The problem that the luminescent efficiency of the blue-light emitting material in the prior art is low. Di(4-bromophenyl)biphenyl silane and A substituent-containing anthracene boric acid are used as the raw materials of the material provided by the invention. The silicon-containing organic luminescent material obtained through reaction has high luminescent efficiency and is a novel electroluminescent material with high performance. The preparation method is simple in synthesis step, low in cost and is suitable for large industrialization requirement. The silicon-containing organic luminescent material provided by the invention can be used as a luminescent material, a luminescent main material or a transmission material due to the high luminescent efficiency, can be applied to an electroluminescent device, and is an organic electroluminescent material with a bright prospect.
Description
Technical field
The invention belongs to organic photoelectrical material field, particularly a kind of siliceous luminous organic material and its preparation method and application.
Background technology
Organic electroluminescence device (OLED) as a kind of flat panel display, have such as luminous, high brightness, wide viewing angle, ultra-thin, less energy-consumption, fast response time, rollable, can the many merits such as Full color be realized.Therefore, at nearest Two decades years, this device achieves the development of advancing by leaps and bounds, and the process of its industrialization is also in continuous forward impelling.But first and last, still have a lot of critical technical barrier not solve.Single angle from material, the red, green, blue luminescent material of excellent property is the most important condition realizing total colouring.But the research of just current electroluminescent organic material, except the better performances of green light material, the performance of Red and blue light material still can not meet commercialization requirement at present, particularly the luminous efficiency of blue light material is lower, the problem that film forming properties is bad, makes current blue light material also only can meet the application of certain fields.Current blue light material mainly comprises fragrant blue light material, arylamine class blue light material, the organic boron class blue light material of carbon containing and hydrogen, silicone based blue light material etc.Wherein, organosilicon blue light material obtains very large development in electroluminescent device.But in the evolution of OLED, organosilicon blue light material is low due to luminous efficiency, its application in electroluminescent device is subject to certain restrictions again.Further, the preparation method of organosilicon blue light material is complicated, and cost is high, and productive rate and purity are not high yet.Therefore, existing organosilicon blue light material also cannot meet the demand of industrialization.
Summary of the invention
The present invention solves the problem that prior art blue light material cannot meet the demand of industrialization, and provides and a kind ofly have high siliceous luminous organic material of higher photoluminescence efficiency, low cost, productive rate and purity and its preparation method and application.
Siliceous luminous organic material, the general structure of this luminous organic material as the formula (1):
Formula (1)
Wherein, A is C
9-C
18fused ring aryl, C
8-C
18aromatic heterocyclic radical or triarylamine.
Preferred siliceous luminous organic material of the present invention, wherein A is 2-naphthyl, 9,9-dimethyl-2-fluorenyls, 5-benzofuryl, 3-perylene base, N-phenyl-3-carbazyl, 2-indenyl or 2-pyrenyl.
Siliceous luminous organic material, it is any one in following chemical structural formula:
Be exactly concrete structure formation more above, but this series compound does not limit to and these listed chemical structures.Every based on formula (1), A group for it before definition all scopes in the compound of simple transformation of group all should be included.
The preparation method of siliceous luminous organic material, concrete steps and the condition of this preparation method are as follows:
Take two (4-bromophenyl) diphenyl silane for 1:0.7 ~ 1.5 in molar ratio and contain A substituent anthracene class boric acid;
Add four (triphenyl phosphorus) palladium, sodium carbonate and solvent, four (triphenyl phosphorus) palladium is 1:20 ~ 1000 with the mol ratio of two (4-bromophenyl) diphenyl silane, and sodium carbonate is 1 ~ 4:1 with the mol ratio of two (4-bromophenyl) diphenyl silane;
Degassed to reaction system;
The temperature of reaction system is risen to 70 ~ 100 DEG C, back flow reaction 24 ~ 30 hours;
Cooling, after suction filtration, washing, drying, obtains described siliceous luminous organic material.
In above-mentioned preparation method, the solvent added is tetrahydrofuran (THF).
In above-mentioned preparation method, after degassed, the temperature of reaction system is risen to 80 ~ 90 DEG C.
In above-mentioned preparation method, reflux time is 26 ~ 28 hours.
The invention has the beneficial effects as follows:
1, siliceous luminous organic material of the present invention is, four aryl silicon have connected different substituted radicals by anthracene, the introducing of these substituted radicals can change lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy level of this compounds, namely changes transition of electron energy level.So the emmission spectrum of this compounds has controllability, by regulating emmission spectrum that this material can be enable to launch blue light, luminous efficiency also significantly improves.Further, because we are that this material also has better film forming properties based on four aryl silicon; Therefore, luminous organic material of the present invention is the novel high performance electroluminescent material of a class.
Particularly when substituted radical is 3-naphthyl, 9, when 9-dimethyl-2-fluorenyl, 5-benzofuryl, triarylamine, 3-perylene base, N-phenyl-3-carbazyl, 2-indenyl or 2-pyrenyl, the luminous efficiency of such luminous organic material prepared in dilute solution can reach 96.7%, and luminous efficiency in the film can reach 58.1%.
2, the preparation method of siliceous luminous organic material provided by the invention is by strictly controlling temperature of reaction, and the conditions such as reaction times prepare the luminous organic material with higher photoluminescence efficiency; This preparation method has productive rate high (productive rate can reach 90%), purity high (HPLC purity is greater than 98%), and synthesis step is simple, and cost is lower, can adapt to the advantage of extensive industrialization needs.
Particularly, when the temperature of reaction of reaction system controls at 80 ~ 90 DEG C, reflux time is 26 ~ 28 hours, the luminous organic material prepared, and the luminous efficiency in dilute solution can reach 97%, and luminous efficiency in the film can reach 65.5%.
3, siliceous luminous organic material of the present invention is owing to having higher luminous efficiency, can be used as luminescent material, light emitting host material or transport material, is applied on electroluminescent device, is a very promising class electroluminescent organic material.
Embodiment
Siliceous luminous organic material provided by the invention is with two (4-bromophenyl) diphenyl silane and contain A substituent anthracene class boric acid for raw material, and be obtained by reacting, its synthetic route is as follows:
Embodiment 1
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(2-naphthyl)-9-anthryl) boric acid 15.67g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 70 DEG C, back flow reaction 24 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-naphthyl)-9-anthryl) phenyl) diphenyl silane 38.89g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 941.24; Test value is 941.26.Ultimate analysis: calculated value is C:91.88%; H:5.14%; Si:2.98%; Test value is C:91.86%; H:5.12%; Si:3.04%.
Concrete synthetic route is shown below:
Embodiment 2
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(9,9-dimethyl-2-fluorenyl) 9-anthryl) boric acid 28.91g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 100 DEG C, back flow reaction 30 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake is after water, ethanol and washed with diethylether, oven dry obtains two (4-(10-(2-fluorenyl)-9-anthryl) phenyl) diphenyl silane 45.08g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1073.44; Test value is 1073.42.Ultimate analysis: calculated value is C:91.75%; H:5.63%; Si:2.62%; Test value is C:91.76%; H:5.62%; Si:2.60%.
Concrete synthetic route is shown below:
Embodiment 3
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(5-benzofuryl) 9-anthryl) boric acid 23.59g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 85 DEG C, back flow reaction 27 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-benzofuryl)-9-anthryl) phenyl) diphenyl silane 38.69g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 921.16; Test value is 921.18.Ultimate analysis: calculated value is C:88.66%; H:4.81%; O:3.47%; Si:3.05%; Test value is C:88.64%; H:4.82%; O:3.48%; Si:3.05%.
Concrete synthetic route is shown below:
Embodiment 4
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(1-triarylamine)-9-anthryl) boric acid 32.47g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 80 DEG C, back flow reaction 26 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-triarylamine)-9-anthryl) phenyl) diphenyl silane 49.37g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1175.53; Test value is 1175.50.Ultimate analysis: calculated value is C:89.91%; H:5.32%; N:2.38%; Si:2.39%; Test value is C:89.90%; H:5.32%; N:2.36%; Si:2.37%.
Concrete synthetic route is shown below:
Embodiment 5
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(3-perylene base)-9-anthryl) boric acid 30.10g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 90 DEG C, back flow reaction 28 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-perylene base)-9-anthryl) phenyl) diphenyl silane 50.04g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1191.53; Test value is 1191.51.Ultimate analysis: calculated value is C:92.74%; H:4.91%; Si:2.36%; Test value is C:92.72%; H:4.90%; Si:2.38%.
Concrete synthetic route is shown below:
Embodiment 6
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(N-phenyl-3-carbazyl)-9-anthryl) boric acid 32.33g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 80 DEG C, back flow reaction 24 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-N-phenyl carbazole base)-9-anthryl) phenyl) diphenyl silane 49.20g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1171.50; Test value is 1171.48.Ultimate analysis: calculated value is C:90.22%; H:4.99%; N:2.39%; Si:2.40%; Test value is C:90.21%; H:4.98%; N:2.40%; Si:2.41%.
Concrete synthetic route is shown below:
Embodiment 7
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(2-indenyl)-9-anthryl) boric acid 23.46g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 100 DEG C, back flow reaction 24 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-indenyl)-9-anthryl) phenyl) diphenyl silane 38.52g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 917.22; Test value is 917.20.Ultimate analysis: calculated value is C:91.66%; H:5.27%; Si:3.06%; Test value is: C:91.68%; H:5.29%; N:3.04%.
Concrete synthetic route is shown below:
Embodiment 8
By two (4-bromophenyl) diphenyl silane 34.49g, (10-(2-pyrenyl)-9-anthryl) boric acid 29.46g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml adds there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 80 DEG C, back flow reaction 24 hours, is cooled to room temperature, after separating out solid, suction filtration, filter cake, after water, ethanol and washed with diethylether, is dried and is obtained two (4-(10-(2-pyrenyl)-9-anthryl) phenyl) diphenyl silane 45.75g, productive rate more than 90%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1089.40; Test value is 1089.42.Ultimate analysis: calculated value is C:92.61%; H:4.81%; Si:2.58%; Test value is: C:92.62%; H:4.80%; Si:2.57%.
Concrete synthetic route is shown below:
Application example 1
It is formed with the ito glass substrate of 1000 thickness above, is placed on the ultrasonic middle cleaning 30 minutes of washings, then uses distilled water ultrasonic cleaning 10 minutes twice.After distilled water wash, use Virahol respectively, toluene, acetone, ethanol difference ultrasonic cleaning 30 minutes, then dry.Finally put into plasma washing machine, with oxygen plasma cleaning base plate 5 minutes, send into vacuum evaporation equipment and process.
By NPB, sample prepared by embodiment 1 ~ 8, AlQ, LiF, Al respectively evaporation, on device, make object construction device: [sample (30nm)/AlQ (20nm)/LiF (5nm)/Al (10nm) prepared by ITO/NPB (20nm)/embodiment 1 ~ 8], organism velocity of evaporation is 1/s, the velocity of evaporation of LiF is the velocity of evaporation of 0.5/s, Al is 2/s, and vacuum tightness remains 10
-5the vacuum tightness of below pa.
The test result of the device 001 that embodiment 1 sample is made is cut-in voltage 4v, and high-high brightness is 3600cd/m
2, observing efficiency under 10v voltage is 27Lm/w, and chromaticity coordinates (CIE) value is x:0.18; Y:0.19, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 002 that embodiment 2 sample is made is cut-in voltage 4v, and high-high brightness is 3600cd/m
2, observing efficiency under 10v voltage is 25Lm/w, and chromaticity coordinates (CIE) value is x:0.16; Y:0.15, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 003 that embodiment 3 sample is made is cut-in voltage 3v, and high-high brightness is 3800cd/m
2, observing efficiency under 10v voltage is 26Lm/w, and chromaticity coordinates (CIE) value is x:0.18; Y:0.19, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 004 that embodiment 4 sample is made is cut-in voltage 5v, and high-high brightness is 3700cd/m
2, observing efficiency under 10v voltage is 29Lm/w, and chromaticity coordinates (CIE) value is x:0.18; Y:0.17, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 005 that embodiment 5 sample is made is cut-in voltage 3v, and high-high brightness is 3600cd/m
2, observing efficiency under 10v voltage is 27Lm/w, and chromaticity coordinates (CIE) value is x:0.16; Y:0.18, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 006 that embodiment 6 sample is made is cut-in voltage 4v, and high-high brightness is 3800cd/m
2, observing efficiency under 10v voltage is 26Lm/w, and chromaticity coordinates (CIE) value is x:0.18; Y:0.17, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 007 that embodiment 7 sample is made is cut-in voltage 5v, and high-high brightness is 3600cd/m
2, observing efficiency under 10v voltage is 28Lm/w, and chromaticity coordinates (CIE) value is x:0.16; Y:0.17, obtains a blue device, and life-span transformation period of device is 20000 hours.
The test result of the device 008 that embodiment 8 sample is made is cut-in voltage 3v, and high-high brightness is 3500cd/m
2, observing efficiency under 10v voltage is 27Lm/w, and chromaticity coordinates (CIE) value is x:0.16; Y:0.18, obtains a blue device, and life-span transformation period of device is 20000 hours.
Table 1: the luminous efficiency of sample compound prepared by embodiment 1 ~ 8
| Sample | Luminous efficiency in dilute solution | Luminous efficiency in film |
| Embodiment 1 | 95% | 56% |
| Embodiment 2 | 96% | 56% |
| Embodiment 3 | 97% | 57% |
| Embodiment 4 | 96% | 66% |
| Embodiment 5 | 98% | 65% |
| Embodiment 6 | 97% | 55% |
| Embodiment 7 | 97% | 56% |
| Embodiment 8 | 98% | 54% |
As can be seen from the data of table 1, the luminous efficiency of the siliceous luminous organic material that embodiment 1 ~ 8 prepares in dilute solution is 96.7%, luminous efficiency is in the film 58.1%, show that such silicon-containing compound has high luminous efficiency, can be used as luminescent material or light emitting host material and transport material, be applied in electroluminescent device.Simultaneously according to application example 1, sample compound prepared by embodiment 1 ~ 8 is applied in organic electroluminescence device by we, by data test with compare, we find that this compounds is the electroluminescent organic material of excellent property, particularly, as the good light emitting host material of Performance Ratio and transport material, it is a very promising class electroluminescent organic material.
Obviously, above-described embodiment is only for clearly example being described, and the restriction not to embodiment.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here exhaustive without the need to also giving all embodiments.And thus the apparent change of extending out or variation be still among the protection domain of the invention.
Claims (4)
1. the preparation method of siliceous luminous organic material, is characterized in that, concrete steps and the condition of this preparation method are as follows:
Take two (4-bromophenyl) diphenyl silane for 1:0.7 ~ 1.5 in molar ratio and contain A substituent anthracene class boric acid;
Add four (triphenyl phosphorus) palladium, sodium carbonate and solvent, four (triphenyl phosphorus) palladium is 1:20 ~ 1000 with the mol ratio of two (4-bromophenyl) diphenyl silane, and sodium carbonate is 1 ~ 4:1 with the mol ratio of two (4-bromophenyl) diphenyl silane;
Degassed to reaction system;
The temperature of reaction system is risen to 70 ~ 100 DEG C, back flow reaction 24 ~ 30 hours;
Cooling, after suction filtration, washing, drying, obtain described siliceous luminous organic material, its general structure is such as formula shown in (1):
In formula, A substituting group is C
9-C
18fused ring aryl, 5-benzofuryl or triarylamine.
2. the preparation method of luminous organic material siliceous as claimed in claim 1, is characterized in that, the solvent added is tetrahydrofuran (THF).
3. the preparation method of luminous organic material siliceous as claimed in claim 1, is characterized in that, after degassed, the temperature of reaction system is risen to 80 ~ 90 DEG C.
4. the preparation method of luminous organic material siliceous as claimed in claim 3, is characterized in that, reflux time is 26 ~ 28 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210457333.8A CN103102877B (en) | 2012-11-14 | 2012-11-14 | Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210457333.8A CN103102877B (en) | 2012-11-14 | 2012-11-14 | Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103102877A CN103102877A (en) | 2013-05-15 |
| CN103102877B true CN103102877B (en) | 2015-04-15 |
Family
ID=48311084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210457333.8A Active CN103102877B (en) | 2012-11-14 | 2012-11-14 | Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103102877B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102100371B1 (en) * | 2013-08-22 | 2020-04-16 | 삼성디스플레이 주식회사 | Anthracene-based compounds and Organic light emitting device comprising the same |
| KR102083986B1 (en) | 2013-08-22 | 2020-03-05 | 삼성디스플레이 주식회사 | Anthracene-based compounds and Organic light-emitting device comprising the same |
| CN109593081B (en) * | 2018-11-07 | 2020-10-27 | 北京绿人科技有限责任公司 | Compound for organic photoelectric device and organic photoelectric device comprising same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101730731A (en) * | 2007-05-21 | 2010-06-09 | 葛来西雅帝史派有限公司 | Organic electroluminescent compounds and organic light emitting diode using the same |
| CN102031104A (en) * | 2010-11-16 | 2011-04-27 | 西安瑞联近代电子材料有限责任公司 | Bipolar phosphorescent main material containing anthracene derivatives of tetraphenyl silicane and carbazole and organic electroluminescent device |
| US8043726B2 (en) * | 2008-02-18 | 2011-10-25 | Samsung Mobile Display Co., Ltd. | Silanylamine-based compound and organic light emitting diode |
-
2012
- 2012-11-14 CN CN201210457333.8A patent/CN103102877B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101730731A (en) * | 2007-05-21 | 2010-06-09 | 葛来西雅帝史派有限公司 | Organic electroluminescent compounds and organic light emitting diode using the same |
| US8043726B2 (en) * | 2008-02-18 | 2011-10-25 | Samsung Mobile Display Co., Ltd. | Silanylamine-based compound and organic light emitting diode |
| CN102031104A (en) * | 2010-11-16 | 2011-04-27 | 西安瑞联近代电子材料有限责任公司 | Bipolar phosphorescent main material containing anthracene derivatives of tetraphenyl silicane and carbazole and organic electroluminescent device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103102877A (en) | 2013-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101784635B (en) | Material for organic photoelectric device, and organic photoelectric device including the same | |
| CN103805165B (en) | A kind of Benzanthracenes electroluminescent organic material and its preparation method and application | |
| CN103113289B (en) | Organic electroluminescent material containing benzanthracene derivative and preparation method of organic electroluminescent material | |
| CN103468246A (en) | Organic luminescent material containing 1,2,4-tolyltriazole as well as preparation method and electroluminescent appliance of organic luminescent material containing 1,2,4-tolyltriazole | |
| CN103805166B (en) | Benzanthracenes luminous organic material and its preparation method and application | |
| CN103102877B (en) | Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material | |
| CN103805169B (en) | Siliceous Benzanthracenes electroluminescent organic material and its preparation method and application | |
| CN105131939A (en) | Organic electroluminescence material with spiral structure and application thereof | |
| CN103805164A (en) | Benzanthracene organic luminescent material, and preparation method and application thereof | |
| CN103805167B (en) | Organic blue luminescent material and its preparation method and application | |
| CN103834381B (en) | Siliceous Benzanthracenes luminous organic material and its preparation method and application | |
| CN108373455A (en) | A kind of organic photoelectrical material and its application | |
| CN110845421A (en) | Electron transport compound, synthesis method thereof and organic electroluminescent device | |
| CN103102299B (en) | A kind of benzanthrene derivative, its preparation method and the electroluminescent organic material be made up of it | |
| CN103805168B (en) | Benzanthracenes electroluminescent organic material and its preparation method and application | |
| CN106549103B (en) | Only electronics organic semiconductor diodes device | |
| CN106008264A (en) | Organic electroluminescent material, application and device thereof | |
| CN103242358B (en) | Siliceous dianthranide derivative and its preparation method and application and organic electroluminescence device | |
| CN106543172B (en) | Organic Electron Transport Material | |
| CN103804408A (en) | Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof | |
| CN104650118B (en) | Preparation method and application of derivative by taking dibenzofuran as skeleton core | |
| CN108218860A (en) | A kind of miscellaneous anthracene derivant and preparation method thereof and organic luminescent device | |
| CN109912609A (en) | Compound taking nitrogen-containing five-membered heterocycle as mother nucleus and application of compound in organic electroluminescent device | |
| CN106543157A (en) | A kind of electroluminescent organic material and its organic electroluminescence device | |
| CN106495975B (en) | 9, 9' -bianthracene blue light multifunctional material 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 | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |