CN101497624A - Bridged triphenyl amine compound, and use in electrophosphorescent device - Google Patents
Bridged triphenyl amine compound, and use in electrophosphorescent device Download PDFInfo
- Publication number
- CN101497624A CN101497624A CNA2009100611714A CN200910061171A CN101497624A CN 101497624 A CN101497624 A CN 101497624A CN A2009100611714 A CNA2009100611714 A CN A2009100611714A CN 200910061171 A CN200910061171 A CN 200910061171A CN 101497624 A CN101497624 A CN 101497624A
- Authority
- CN
- China
- Prior art keywords
- layer
- electro
- ppy
- phosphorescent device
- firpic
- 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
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses bridged triphenylamine compounds and an electrophosphorescent device taking the bridged triphenylamine compounds as a main body material. A general structural formula of the compounds is shown at the right, wherein Ar2s are triphenylsilyls or 9-phenylflourenyls which are the same as each other when Ar1s are phenyls; and the Ar2s are the triphenylsilyls or 9-p-tolyl flourenyls which are the same as each other when the Ar1s are p-tolyls. The electrophosphorescent device produced by taking the compounds as the main body material has high-efficiency and high-brightness electroluminescent property, and can be widely applied in the field of organic electroluminescence.
Description
Technical field
The present invention relates to a class bridged triphenyl amine compound and the application in electro phosphorescent device thereof, belong to field of organic electroluminescent materials.
Background technology
From people's reported first such as the C.W.Tang of Kodak in 1987 prepare by vacuum deposition method with Alq3 be the bi-layer devices structure of luminescent material since, organic electroluminescent has just obtained people's very big concern.
Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent.According to spin quantum statistical theory, the formation probability proportion of singlet state exciton and triplet exciton is 1:3, promptly the singlet state exciton only account for " electron-hole pair " 25%.Therefore, the fluorescence that comes from the radiative transition of singlet state exciton just only accounts for 25% of total input energy, and the electroluminescent of phosphor material just can utilize the energy of whole excitons, thereby has bigger superiority.
Adopt the Subjective and Objective structure in the present phosphorescence electroluminescent device mostly, soon the phosphorescent emissions material in main substance, to avoid burying in oblivion of concentration quenching and triplet state-triplet state, improves phosphorescent emissions efficient with certain doped in concentrations profiled.
Forrest in 1999 and Thompson etc. [M A Baldo, S Lamansky, P.E.Burroes, M EThompson, S.R.Forrest.Appl Phys Let, 1999,75,4.] with green phosphorescent material Ir (ppy)
3With the doped in concentrations profiled of 6wt% 4,4 '-N is in the material of main part of N '-two carbazoles-biphenyl (CBP), and introduced hole barrier layer material 2,9-dimethyl 4,7-phenylbenzene-1,10-phenanthroline (BCP), the maximum external quantum efficiency of the green glow OLED that obtains reaches 8%, power efficiency reaches 31lm/W, all substantially exceeds the electroluminescent fluorescent luminescent device, has caused the extensive concern of people to the heavy metal complex luminescent material immediately.
(Adachi, Chihaya.Baldo, Marc A.Forrest, Stephen R.Thompson, Mark E., Appl Phys Let, 2000,77,904) such as Forrest were with Ir (ppy) in 2000
3(1 '-Nai Ji)-5-phenyl-1,2 in the 4-triazole (TAZ), obtains the device maximum power efficiency and reaches 40 ± 21m/W to be entrained in the main body 3-phenyl-4-of electron-transporting type.
Forrest (Holmes, R.J.Forrest, S.R.Tung in 2003, Y.-J.Kwong, R.C.and Brown, J.J.Garon, S.Thompson, M.E., Appl Phys Let, 2003,82,2422) realized blue light complex of iridium FIrpic again, it has been entrained in main body N, the device maximum current efficient and the power efficiency of preparation are respectively 7.5 ± 0.8cd/A and 8.9 ± 0.9lm/W in N '-two carbazyl-3,5-substituted benzene (mCP).
In recent years, the material of main part about triphenylamine also has report.Shu etc. (Shih, Ping-I.Chien, Chen-Han.Wu, Fang-Iy.Shu, Ching-Fong., Adv.Funct.Mater.2007,17,3514) are with Ir (ppy)
3With FIrpic with the doped in concentrations profiled of 21wt% in material of main part three (4-(9-phenyl fluorenyl)-phenyl) amine (TFTPA), the power efficiency of device can reach 15.6lm/W and 12.2lm/W respectively.
But the triphenyl amine compound as material of main part of report because its rigidity is strong inadequately, causes its thermostability not high enough at present, and is in addition, that its luminous efficiency as the electro phosphorescent device of material of main part preparation is also not high enough.
Summary of the invention
The objective of the invention is to remedy the deficiencies in the prior art, provide a class bridged triphenyl amine compound and the organic electro phosphorescent device with high efficiency electroluminous performance of this compounds as material of main part.
Bridged triphenyl amine compound of the present invention, its general structure is:
In the formula (1), work as Ar
1During for phenyl, Ar
2Silica-based or 9-phenyl fluorenyl is worked as Ar for mutually the same triphen
1During for p-methylphenyl, Ar
2Silica-based or 9-p-methylphenyl fluorenyl is also promptly worked as Ar for mutually the same triphen
1For
The time, Ar
2For mutually the same
Or
, work as Ar
1For
The time, Ar
2For mutually the same
Or
Bridged triphenyl amine compound of the present invention is as electro-phosphorescent main body material.
Electro phosphorescent device of the present invention, comprise glass, attached to Conducting Glass layer on glass, the hole injection layer that closes with the Conducting Glass laminating, hole transmission layer with the hole injection layer applying, luminescent layer with the hole transmission layer applying, hole blocking layer with the luminescent layer applying, electron transfer layer with the hole blocking layer applying, cathode layer with the electron transfer layer applying, wherein luminescent layer is made up of material of main part and dopant material, the material of main part of luminescent layer is the described compound of formula (1), and dopant material is the common complex of iridium with cyclic metal complexes, as the FIrpic of blue light-emitting or the Ir of green light (ppy)
3Usually the doping content of FIrpic is 4～8wt%, is preferably 6wt%; Ir (ppy)
3Doping content be 6～12wt%, be preferably 9wt%.
To have the triphenylamine units bridging of hole transport performance among the present invention, and increase molecular rigidity, and connect fluorenes or triphenyl silicon group in unconjugated mode then, molecular system increases but still keeps a high triplet, simultaneously second-order transition temperature (T
g) raise, thereby the triphenyl amine compound that obtains has high thermostability, with they material of main parts as the electro phosphorescent device luminescent layer, the stability of device improved, and obtains electroluminescent properties efficiently simultaneously.The present invention is based on them, with Ir (ppy)
3For the high-high brightness of the prepared green device of object reaches 24029cd/m
2, maximum luminous efficiency can reach 71cd/A, and maximum power efficiency is one of most effective value of present single-shot photosphere device current up to 64lm/W, and device performance is higher than the device based on the most frequently used material C BP far away; The blue-light device maximum luminous efficiency that based on them, with FIrpic is the object preparation can reach 44cd/A, and maximum power efficiency reaches 35lm/W, also is one of best device of performance so far.
Description of drawings
One of Fig. 1 material of main part of the present invention 3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9, the uv-visible absorption spectra figure of 9-tetraphenyl-13b-azepine naphthanthracene solution;
One of Fig. 2 material of main part of the present invention 3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9, the photoluminescence figure of 9-tetraphenyl-13b-azepine naphthanthracene solution;
Fig. 3 electroluminescent device structural representation of the present invention;
The emmission spectrum of Fig. 4 electroluminescent device of the present invention, wherein, solid line is the emmission spectrum of device 1, dotted line is the emmission spectrum of device 2.
Embodiment
The present invention is further illustrated below by specific embodiment, and its purpose is to help better to understand content of the present invention, but the protection domain that these specific embodiments do not limit the present invention in any way.
The used raw material of the present embodiment is a known compound, can buy on market, or available methods known in the art is synthetic.
Embodiment 1
3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9, the preparation of 9-tetraphenyl-13b-azepine naphthanthracene (being abbreviated as Host1)
1.4g bromobenzene (8.8mmol) is dissolved in 10ml THF in Shiran gram bottle (Schlenk bottle).3.4ml (2.6M 8.8mmol) splashes in the Schlenk bottle under-78 ℃ of conditions n-BuLi, drips off the back and reacts 1h down at-78 ℃.0.83g2-(diphenylamino)-5-tertiary butyl-1,3-dimethyl isophthalate splash in the Schlenk bottle after being dissolved in 10ml THF, reaction 3h.Reaction finishes the back and carries out cancellation with distilled water.Extracted with diethyl ether is told organic phase, washes anhydrous Na with water three times
2SO
4Dry.Be spin-dried for organic solvent and get the light green solid.This thick product is dissolved in the 30ml glacial acetic acid, 110 ℃ of reflux, the careful dense HCl of 3ml that splashes into, reaction 3h.Reaction finishes back solution and pours in the 200ml frozen water.The 20ml chloroform extracts respectively three times, gets red solution.Thick product sherwood oil: methylene dichloride=2:1 (volume ratio) crosses the post separation after being spin-dried for chloroform, gets the white solid 7-tertiary butyl-5,5,9,9-tetraphenyl bridged triphenyl amine 0.8g, productive rate 83%.
1H?NMR(300MHz，CDCl
3，δ)：7.29-7.26(m，6H)，7.12-7.03(m，14H)，6.91-6.83(m，8H)，6.76(d，J＝7.8Hz，2H)，1.08(s，9H)；
13C?NMR(300MHz，CDCl
3，δ)：145.92，143.64，139.08，135.14，131.56，129.99，129.00，127.60，127.37，126.46，126.07，124.59，121.80，116.93，57.343，34.28，31.34.Anal.Calcd.forC
48H
39N(％)：C，91.53；H，6.24；N，2.22.Found：C，91.50；H，6.63；N，2.15.MS(EI)m/z?629.7[M
+]。
0.49g (0.78mmol) the 7-tertiary butyl-5,5,9,9-tetraphenyl bridged triphenyl amine is dissolved in the 20ml chloroform in the 50ml round-bottomed flask, adds 0.31g NBS (1.7mmol), stirring at room reaction 2d.Reaction washes organic phase with water three times, anhydrous Na after finishing
2SO
4Dry.Use sherwood oil: methylene dichloride=3:1 (volume ratio) crosses post and separates, and gets white solid 0.54g, productive rate 88%.Through phenetic analysis, confirm that this white solid is 3, the 11-two bromo-7-tertiary butyls-5,5,9,9-tetraphenyl bridged triphenyl amine.
1H?NMR(300MHz，CDCl
3，δ)：7.33-7.26(m，6H)，7.14-7.08(m，8H)，7.01-6.77(m，14H)；
13C?NMR(300MHz，CDCl
3，δ)：145.32，144.76，138.18，137.88，134.25，132.69，132.65，131.72，131.64，130.00，129.08，128.04，127.94，127.28，126.69，125.02，118.54，115.03，57.64，34.60，31.53.Anal.Calcd.forC
48H
37Br
2N(％)：C，73.20；H，4.73；N，1.78.Found：C，71.11；H，4.23；N，1.61.MS(EI)m/z?785.4[M
+]。
0.46g 3, the 11-two bromo-7-tertiary butyls-5,5,9,9-tetraphenyl bridged triphenyl amine (0.59mmol) is dissolved in the absolute anhydrous THF of 10ml in the Schlenk bottle.Careful splash into 0.71ml n-BuLi (18mmol, 2.5M).-78 ℃ of following stirring reaction 1.5h.0.53g tri-phenyl chloride (18mmol) is dissolved in careful adding behind the absolute anhydrous THF of 5ml.Drip off back low temperature and continue reaction 1h, room temperature reaction 1h uses rare NH more then
4Cl solution carries out cancellation, CHCl
3Extraction.Use sherwood oil: methylene dichloride=3:1 crosses post and separates, and gets white solid.With this white solid with suitable ethyl acetate drip washing.Receive the finished product 0.31g, productive rate 43% through phenetic analysis, confirms that this product is Host1.
1H?NMR(300MHz，CDCl3)：δ?7.09-7.42(m，48H)，6.86-6.94(d，b，10H)，1.06(s，9H)。
1H NMR (300MHz, CDCl
3, δ): 7.34 (d, J=7.2Hz, 12H), 7.29 (d, J=6.6Hz, 6H), 7.20 (t, J=7.2Hz, 12H), 7.14-7.01 (m, 18H), 6.86-6.79 (m, 10H), 0.99 (s, 9H);
13C NMR (300MHz, CDCl
3, δ): 146.29,146.00,140.10,138.98,136.41,134.70,131.67,131.54,129.54,129.30,127.94,127.51,126.68,126.63,126.31,125.25,116.91,57.49,34.52,31.54.Anal.Calcd.for C
84H
67NSi
2(%): C, 87.99; H, 5.89; N, 1.22.Found:C, 88.14; H, 6.27; N, 0.91.MS (MALDI-TOF) m/z 1146.4[M
+] .3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9, the uv-visible absorption spectra figure of 9-tetraphenyl-13b-azepine naphthanthracene solution and photoluminescence figure are respectively as depicted in figs. 1 and 2.
3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9, the preparation of 9-four (p-methylphenyl)-13b-azepine naphthanthracene (being abbreviated as Host2)
Adopt way similar to Example 1, difference is that so that the methyl bromobenzene is replaced bromobenzene be starting raw material, can make 3,11-two (triphen the is silica-based)-7-tertiary butyl-5,5,9,9-four (p-methylphenyl)-13b-azepine naphthanthracene, productive rate 47%.
1H?NMR(300MHz，CDCl
3，δ)：7.42-7.34(m，18H)，7.30-7.25(m，16H)，7.01-6.90(m，12H)，6.80-6.73(m，8H)，2.31(s，6H)，2.25(s，6H)，1.08(s，9H)；
13CNMR(300MHz，CDCl
3，δ)：144.04，143.56，143.30，140.15，139.12，136.43，135.65，135.54，134.79，134.39，131.39，129.44，129.13，128.61，128.15，127.89，126.38，125.06，116.96，99.83，56.83，34.55，31.60，21.29，21.12.Anal.Calcd.for?C
88H
75NSi
2(％)：C，87.88；H，6.29；N，1.16.Found：C，88.36；H，5.96；N，0.85.MS(MALDI-TOF)m/z1201.9[M
+].
3,11-two (9-phenyl the fluorenyl)-7-tertiary butyl-5,5,9, the preparation of 9-tetraphenyl-13b-azepine naphthanthracene (being abbreviated as Host3)
0.31g the 7-tertiary butyl-5,5,9,9-tetraphenyl bridged triphenyl amine (0.5mmol), 0.258g 9-phenyl-9-fluorenol (1mmol) is put into the 50ml round-bottomed flask respectively.Add the 10ml methylene dichloride.Careful adding 0.15ml BF
3Et
2O (1.1mmol, 7.73M).Room temperature reaction 2h.Reaction adds methyl alcohol earlier after finishing, and adds water again and carries out cancellation, tells organic phase.Use sherwood oil: methylene dichloride=2:1 (volume ratio) crosses post and separates, and gets white solid 0.47g, productive rate 86%.Confirm that through phenetic analysis this white solid is Host3.
1H?NMR(300MHz，CDCl
3，δ)：7.67(d，J＝7.2Hz，4H)，7.27-7.25(m，6H)，7.19-7.02(m，24H)，6.99-6.81(m，16H)，6.74-6.62(m，4H)，1.04(s，9H)；
13C?NMR(300MHz，CDCl
3，δ)：151.66，151.46，146.86，146.22，146.06，140.32，140.11，138.92，137.51，134.92，131.87，131.54，131.16，129.31，128.11，127.87，127.71，127.64，127.42，126.45，126.23，125.53，125.35，120.26，120.11，116.51，65.04，57.64，34.48，31.54.Anal.Calcd.for?C
86H
63N(％)：C，93.02；H，5.72；N，1.26.Found：C，93.00；H，5.92；N，1.15.MS(MALDI-TOF)m/z?1109.8[M
+].
3,11-two (9-phenyl the fluorenyl)-7-tertiary butyl-5,5,9, the preparation of 9-four (p-methylphenyl)-13b-azepine naphthanthracene (being abbreviated as Host4)
Adopt way similar to Example 3, difference is that with the 7-tertiary butyl-5,5,9 that makes among the embodiment 2 9-four p-methylphenyl bridged triphenyl amines are starting raw material, can obtain white solid 0.40g, productive rate 67%.Confirm that through phenetic analysis this white solid is Host4.
1H?NMR(300MHz，CDCl
3，δ)：7.66(d，J＝6.6Hz，4H)，7.29-7.24(m，6H)，7.14-7.04(m，8H)，6.94-6.83(m，18H)，6.77-6.66(m，12H)，2.32(s，6H)，2.24(s，6H)，2.23(s，6H)，1.07(s，9H)；
13C?NMR(300MHz，CDCl
3，δ)：152.00，151.79，144.25，143.38，143.17，140.29，140.01，138.61，137.45，135.82，135.60，135.43，135.00，131.83，131.42，129.18，128.86，128.59，128.01，127.72，127.61，127.28，127.32，126.47，126.18，125.43，125.13，120.24，120.07，116.58，64.71，56.93，34.54，31.67，21.31，21.22.Anal.Calcd.for?C
92H
75N(％)：C，92.50；H，6.33；N，1.17.Found：C，92.02；H，6.40；N，0.81.MS(MALDI-TOF)m/z?1193.9[M
+].
The preparation of electro phosphorescent device
As shown in Figure 3, the triphenylamine material of bridged ring rigid structure of the present invention comprises glass and conductive glass (ITO) substrate layer 1, hole injection layer 2 (molybdic oxide MoO as the electro phosphorescent device of luminescent layer main body
3), hole transmission layer 3 (4,4 '-two (N-phenyl-N-naphthyl)-biphenyl NPB) and 4 (N, N '-two carbazyl-3,5-substituted benzene mCP), (luminescent layer is for being doped with 4～8wt% Firpic or 6～12wt% Ir (ppy) for luminescent layer 5
3Host1 or Host2 or Host3 or Host4), electron transfer layer 6 (3-phenyl-4-(1 '-naphthyl)-5-phenyl-1,2,4-triazole TAZ), cathode layer 7 (lithium fluoride/aluminium).D1～D8 totally 8 kinds of devices have been prepared in the present embodiment.
Electroluminescent device can be made by means known in the art, as presses reference (Adv.Mater.2003,15,277.) disclosed method and make.Concrete grammar is: under high vacuum condition, and the MoO of evaporation 10nm successively on through conductive glass (ITO) substrate that cleans
3, the NPB of 80nm, the mCP of 5nm, the luminescent layer of 20nm, the TAZ of 40nm, the LiF of 1nm and the Al of 120nm.Make as shown in Figure 3 device with this method, the structure of various devices is as follows:
Device 1 (D1):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host1：FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 2 (D2):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host1：Ir(ppy)
3(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 3 (D3):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host2：FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 4 (D4):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host2：Ir(ppy)
3(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 5 (D5):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host3：FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 6 (D6):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host3：Ir(ppy)
3(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 7 (D7):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host4：FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Device 8 (D8):
ITO/MoO
3(10nm)/NPB(80nm)/mCP(5nm)/Host4：Ir(ppy)
3(20nm)/TAZ(40nm)/LiF(1nm)/Al(120nm)
Electric current-the brightness of device-voltage characteristic is to be finished by the Keithley source measuring system that has corrected silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter), electroluminescent spectrum is by the French JY SPEX CCD3000 of company spectrometer measurement, and all measurements are all finished in atmosphere at room temperature.
The performance data of device sees the following form:
Claims (8)
1. a class bridged triphenyl amine compound is characterized in that such structural general formula is:
Wherein, work as Ar
1During for phenyl, Ar
2Silica-based or 9-phenyl fluorenyl is worked as Ar for mutually the same triphen
1During for p-methylphenyl, Ar
2Silica-based or the 9-p-methylphenyl fluorenyl for mutually the same triphen.
2. bridged triphenyl amine compound as claimed in claim 1 is as the application of electro-phosphorescent main body material.
3. electro phosphorescent device, comprise glass, attached to Conducting Glass layer on glass, the hole injection layer that closes with the Conducting Glass laminating, hole transmission layer with the hole injection layer applying, luminescent layer with the hole transmission layer applying, hole blocking layer with the luminescent layer applying, electron transfer layer with the hole blocking layer applying, cathode layer with the electron transfer layer applying, it is characterized in that: luminescent layer is made up of material of main part and dopant material, and the material of main part of luminescent layer is a compound as claimed in claim 1.
4. electro phosphorescent device according to claim 4 is characterized in that: dopant material is the FIrpic of blue light-emitting or the Ir of green light (ppy)
3
5. electro phosphorescent device according to claim 5 is characterized in that: the doping content of FIrpic is 4～8wt%.
6. electro phosphorescent device according to claim 5 is characterized in that: Ir (ppy)
3Doping content be 6～12wt%.
7. electro phosphorescent device according to claim 6 is characterized in that: the doping content of FIrpic is 6wt%.
8. electro phosphorescent device according to claim 7 is characterized in that: Ir (ppy)
3Doping content be 9wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100611714A CN101497624B (en) | 2009-03-19 | 2009-03-19 | Bridged triphenyl amine compound, and use in electrophosphorescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100611714A CN101497624B (en) | 2009-03-19 | 2009-03-19 | Bridged triphenyl amine compound, and use in electrophosphorescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101497624A true CN101497624A (en) | 2009-08-05 |
| CN101497624B CN101497624B (en) | 2011-04-20 |
Family
ID=40944912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009100611714A Active CN101497624B (en) | 2009-03-19 | 2009-03-19 | Bridged triphenyl amine compound, and use in electrophosphorescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101497624B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103227285A (en) * | 2013-03-29 | 2013-07-31 | 武汉大学 | Bridged triphenylamine-based polymer solar battery |
| CN109810106A (en) * | 2018-12-30 | 2019-05-28 | 瑞声科技（南京）有限公司 | A kind of light emitting composition and luminescent layer and electroluminescent device comprising the light emitting composition |
| CN110407710A (en) * | 2018-04-28 | 2019-11-05 | 香港科技大学深圳研究院 | A kind of pure organic room temperature phosphorimetry material of triphenylamine derivative class and preparation method thereof |
| CN114874175A (en) * | 2022-05-18 | 2022-08-09 | 武汉尚赛光电科技有限公司 | Heteroanthracene derivative and application and device thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19808088A1 (en) * | 1998-02-20 | 1999-08-26 | Syntec Ges Fuer Chemie Und Tec | New tris(hydroxynaphthylazo) bridged triphenylamine pigments for electrophotographic charge generating layer |
-
2009
- 2009-03-19 CN CN2009100611714A patent/CN101497624B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103227285A (en) * | 2013-03-29 | 2013-07-31 | 武汉大学 | Bridged triphenylamine-based polymer solar battery |
| CN110407710A (en) * | 2018-04-28 | 2019-11-05 | 香港科技大学深圳研究院 | A kind of pure organic room temperature phosphorimetry material of triphenylamine derivative class and preparation method thereof |
| CN110407710B (en) * | 2018-04-28 | 2022-05-06 | 香港科技大学深圳研究院 | Triphenylamine derivative pure organic room temperature phosphorescent material and preparation method thereof |
| CN109810106A (en) * | 2018-12-30 | 2019-05-28 | 瑞声科技（南京）有限公司 | A kind of light emitting composition and luminescent layer and electroluminescent device comprising the light emitting composition |
| CN114874175A (en) * | 2022-05-18 | 2022-08-09 | 武汉尚赛光电科技有限公司 | Heteroanthracene derivative and application and device thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101497624B (en) | 2011-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101333438B (en) | Material with bipolar carrier transmission performance and uses thereof | |
| Liang et al. | High‐Efficiency Red Phosphorescent Iridium Dendrimers with Charge‐Transporting Dendrons: Synthesis and Electroluminescent Properties | |
| Yoo et al. | A new electron transporting material for effective hole-blocking and improved charge balance in highly efficient phosphorescent organic light emitting diodes | |
| Tang et al. | Novel yellow phosphorescent iridium complexes containing a carbazole–oxadiazole unit used in polymeric light-emitting diodes | |
| CN110066297A (en) | Stable emitter | |
| CN103694277A (en) | Red-phosphorescence organic light emitting diode (LED) | |
| CN101863914B (en) | Phosphorescent light body material and application | |
| CN102911145A (en) | Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device | |
| CN104529870A (en) | Adamantane derivatives and application thereof as organic electrophosphorescence main body material | |
| CN109678844A (en) | A kind of orange light hot activation delayed fluorescence material and organic electroluminescence device | |
| CN101225298B (en) | Hole-transporting type blue luminescent material as well as preparation and uses thereof | |
| CN101698672B (en) | Tricarbonal rhenium (I) complexes containing carrier-transporting groups (oxadiazole or carbazole), preparation method and application thereof | |
| CN101497624B (en) | Bridged triphenyl amine compound, and use in electrophosphorescent device | |
| CN101274916B (en) | Multifunctional bipolar carrier transmission material and application thereof | |
| CN103289675A (en) | Fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application | |
| Liang et al. | Bipolar iridium dendrimers containing carbazolyl dendron and 1, 2, 4-triazole unit for solution-processed saturated red electrophosphorescence | |
| CN102391301B (en) | Phosphorescent main body material | |
| CN102391308B (en) | Dendritic iridium coordination compound with double-carrier transport property, application and prepared organic electrophosphorescent device | |
| CN103525399A (en) | Bipolar phosphorescent host compound, preparation method, application and electroluminescent device | |
| Hao et al. | Synthesis and optoelectronic properties of dinuclear iridium (III) complexes containing deep blue fluorescence chromophore in the single-emissive-layer WPLEDs | |
| CN101747289B (en) | Electrophosphorescence devices | |
| CN100361983C (en) | Halogen atom-containing bidentate ligand, its iridium complex and electrogenerated phosphorescence device | |
| CN105131940A (en) | Organic luminescent material containing spirobifluorene and dibenzothiophene and luminescent device | |
| CN103571454A (en) | Iridium containing organic electroluminescent material, preparation method thereof and organic electroluminescent device | |
| Wang et al. | Homoleptic iridium complexes based on furo [3, 2-c] pyridine ligand for efficient phosphorescent OLEDs |
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 | ||
| ASS | Succession or assignment of patent right |
Owner name: CHANGSHU ZIJIN INTELLECTUAL PROPERTY SERVICE CO., Free format text: FORMER OWNER: WUHAN UNIVERSITY Effective date: 20121220 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 430072 WUHAN, HUBEI PROVINCE TO: 215500 SUZHOU, JIANGSU PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20121220 Address after: 215500 Changshou City South East Economic Development Zone, Jiangsu, Jin Road, No. 8 Patentee after: Changshu Zijin Intellectual Property Service Co., Ltd. Address before: 430072 Hubei city of Wuhan province Wuchang Luojiashan Patentee before: Wuhan University |