CN103242299A - Quinazoline derivative and application thereof in organic electroluminescent device - Google Patents
Quinazoline derivative and application thereof in organic electroluminescent device Download PDFInfo
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- CN103242299A CN103242299A CN2013101817759A CN201310181775A CN103242299A CN 103242299 A CN103242299 A CN 103242299A CN 2013101817759 A CN2013101817759 A CN 2013101817759A CN 201310181775 A CN201310181775 A CN 201310181775A CN 103242299 A CN103242299 A CN 103242299A
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Abstract
The invention relates to a quinazoline derivative and an application thereof in an organic electroluminescent device, belonging to the technical field of white light illumination in organic electroluminescence. By adopting the quinazoline derivative, a white light organic electroluminescent device with better CIE coordinates and better spectrum stability can be obtained by carrying out doping evaporation on the quinazoline derivative and solid acid namely camphorsulfonic acid (CSA) with strong acidity and high stability under a high-vacuum-degree condition. Although the data performance of the current device is not ideal enough, the preparation method and process are first cases, and a new idea for synthesizing a white light material and preparing devices in the future is provided.
Description
Technical field
The invention belongs to white-light illuminating technical field in the organic electroluminescent, be specifically related to 2 kinds of quinazoline derivants simple in structure, reach these two kinds of material application aspect organic electroluminescence device.
Background technology
The organic light emission solid (is seen C.W.Tang because it has caused in organic electroluminescent (OLED) field in the potential application aspect solid state lighting and the plane demonstration that people more and more pay close attention to, S.A.Vanslyke, Appl.Phys.Lett.1987,51,913), and wherein the performance of white-light illuminating is more noticeable.Up to now, there have been several different methods and means can realize the white light emission of organic electroluminescent.Comprising, different luminous object mixing and dopings is gone into same luminescent layer (see B.W.D ' Andrade, R.J.Holmes, S.R.Forrest, Adv.Mater.2004,16,624.), introduce different luminescent materials by multilayered structure and (see Y.Sun, N.C.Giebink, H.Kanno, B.Ma, M.E.Thompson, S.R.Forrest, Nature 2006,440,908.), the luminescent device of cascaded structure (is seen F.Guo, D.Ma, Appl.Phys.Lett.2005,87,173510.), and the modes such as Subjective and Objective doping by fluorescence molecule and phosphorescent molecules realize that white light emission (sees B.C.Krummacher, V.-E.Choong, M.K.Mathai, S.A.Choulis, F.So, F.Jermann, T.Fiedler, M.Zachau, Appl.Phys.Lett.2006,88,113506.).
But in these methods, the material of three kinds of glow colors of red, green, blue (RGB) or the Subjective and Objective material of indigo plant/orange light are the most basic requirements, and this also makes and prepares the device architecture complexity difficulty and increase.Though at present by synthetic white luminous polymkeric substance in conjunction with the luminous fragment of RGB, or use microcavity effect and exciplex to realize that single luminescent material prepares the possibility of WOLEDs, but all need usually to experience complicated synthetic and preparation process, and cost is also bigger.In this sense, how to design a synthetic class material, can prepare WOLEDs by simple and economical process has very huge realistic meaning.
Generally speaking, a kind of organic dye can only produce single glow color, realizes that white light emission needs two or three different luminescent material.Recently, people have entered deep research for how to regulate and control organic dye glow color aspect by the change environmental factors.The result shows, by the specific molecule structure with to the outside stimulus of organic solid, may influence conformation or the packed structures of molecule, thereby change its glow color.These stimuli responsive change in fluorescence comprise that piezallochromy (sees Bi, H., Chen, D., Li, D., Yuan, Y., Xia, D., Zhang, Z., Zhang, H., Wang, Y.Chem.Commun., 2011,47,4135), solvent atmosphere stimulates variable color (to see C.Dou, L.Han, S.Zhao, H.Zhang, Y.Wang, J.Phys.Chem.Lett.2011,2,666.), thermochromism (is seen Y.Zhao, H.Gao, Y.Fan, T.Zhou, Z.Su, Y.Liu, Y.Wang, Adv.Mater.2009,21,3165) and photochromicly (see Z.Zhang, D.Yao, T.Zhou, H.Zhang, Y.Wang, Chem.Commun.2011,47,7782.).
Although the research to intelligent luminescent material in the past decade becomes a hot issue, because preparation technology's restriction makes that its application in the organic electroluminescent field is very limited.
Summary of the invention
The purpose of this invention is to provide a kind of molecule with sour stimuli responsive metachromatism, and it is applied in the organic electroluminescent field, the material that relates to have be easy to prepare, advantage with low cost, and the device for preparing has white luminous CIE coordinate and spectrum stability preferably.
The present invention utilizes the method for vacuum evaporation to stimulate blue light material to produce orange light emission by acid, and the incomplete energy between blue light and orange optical molecule shifts to realize the preparation of white light organic electroluminescent device.
Compound (1), (2) are made with carbazole and diphenylamine reaction respectively by the Ullman reaction by 2-(4-bromobenzene)-4-phenylquinazoline respectively, and synthetic route and molecular structure are as follows:
Compound of the present invention (1) and (2) all can by with the mode of the solid acid-camphorsulfonic acid with strongly-acid and high stability (CSA) doping evaporation under the condition of high vacuum degree condition, obtain to have better CIE coordinate and the better white light organic electroluminescent device of spectrum stability.Although the data of device performance at present is very good not enough, this preparation method and technology still belong to the first, have also opened a new thinking for the synthetic and device preparation of white light material in the future.
Description of drawings
Fig. 1: electroluminescent device structural representation of the present invention;
As shown in Figure 1, each component names is: be attached to ito anode 1, NPB(N on the transparent glass, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-biphenyl-4,4 '-diamines) hole transmission layer 2, TCTA(4,4 ', 4 " 3 (N-phenyl carbazole) triphenylamine) electronic barrier layer 3, compound of the present invention (1) or (2) form luminescent layer 4, TPBI or Bepp as material of main part doping CSA
2 Electron transfer layer 5, LiF electron injecting layer 6, metal A l negative electrode 7.
Fig. 2: the electroluminescent spectrum figure of the embodiment of the invention 5 described devices;
Fig. 3: the electroluminescent spectrum figure of the embodiment of the invention 6 described devices.
Embodiment
Embodiment 1: intermediate synthetic
In the 500mL three-necked bottle, add the 1M tetrahydrofuran solution 100mL (100mmol) of phenyl magnesium bromine compounds, add dry ether 100mL, carry out 45 ℃ oil bath reflux.With 30 minutes, to the dry ether 50mL solution that wherein splashes into 2-benzonitrile ammonia 5.91g (50mmol).After carrying out 1.5 hours backflow again, ice-water bath is cooled to 0 ℃.Be connected on the dry ether 100mL solution that splashes into 4-bromo-benzoyl chloride 13.2g (60mmol), carry out 45 ℃ of oil bath reflux of 2 hours.After reaction finished, ice-water bath was cooled to 0 ℃, added saturated aqueous ammonium chloride.Filter and take out precipitate, small amount of methanol is cleaned the final vacuum drying, obtains intermediate 7.59g(productive rate 42%).
Embodiment 2: compound (1) and (2) synthetic
Under the condition of nitrogen gas, to intermediate 180mg (0.5mmol) is housed, carbazole 100mg (0.6mmol) adds palladium 25mg and tri-butyl phosphine 0.1mL, reflux 4 hours in the two-mouth bottle of potassium tert.-butoxide 168mg (1.5mmol) and toluene 25mL.Behind the stopped reaction, remove solvent, residuals is done the eluent silicagel column with methylene dichloride and is separated, and obtains compound (1).1H?NMR(300MHz;CDCl
3):δ8.93(d,J=8.4Hz,2H),8.27(d,J=8.7Hz,1H),8.18(m,3H),7.91–7.98(m,3H),7.74–7.78(m,2H),7.59–7.66(m,4H),7.54(d,J=8.4Hz,2H),7.41–7.47(m,2H),7.28–7.34(m,2H).
Synthesizing of compound (2) is identical with compound (1), gets final product with the pentanoic substituted carbazole.1H?NMR(300MHz;CDCl
3):δ8.54(d,J=7.8Hz,2H),8.12(d,J=8.7Hz,2H),7.85–7.89(m,3H),7.57–7.60(m,3H),7.50–7.55(m,1H),7.25-7.31（m,4H），7.18(d,J=8.7Hz,6H),7.05–7.10(m,2H).
Embodiment 3: luminescent device [ITO/NPB/TCTA/(1)/TPBI/LiF/Al]
Be coated with on the glass substrate of ito anode evaporation hole transmission layer NPB(40nm successively), electronic barrier layer TCTA(5nm), compound (1) is luminescent layer (15nm), electron transfer layer TPBI(45nm), electron injecting layer LiF(1nm), Al negative electrode (100nm).Keep-up pressure in evaporate process is 5 * 10
-6Pa.This device cut-in voltage that makes is 3.2V, high-high brightness 1945cd m
-2, maximum current efficient 0.93cd A
-1, maximum power efficiency 0.88lm W
-1, luminous peak position is blue emission at 445nm.
Embodiment 4: luminescent device [ITO/NPB/TCTA/(2)/TPBI/LiF/Al]
Be coated with on the glass substrate of ito anode evaporation hole transmission layer NPB(40nm successively), electronic barrier layer TCTA(5nm), compound (2) is luminescent layer (15nm), electron transfer layer TPBI(45nm), electron injecting layer LiF(1nm), Al negative electrode (100nm).Keep-up pressure in evaporate process is 5 * 10
-6Pa.This device cut-in voltage is 3.7V, high-high brightness 7934cd m
-2, maximum current efficient 4.57cd A
-1, maximum power efficiency 2.85lm W
-1, luminous peak position is the blue green light emission at 496nm.
Embodiment 5: luminescent device [ITO/NPB/TCTA/(1): CSA (0.1%)/TPBI/LiF/Al]
Be coated with on the glass substrate of ito anode evaporation hole transmission layer NPB(40nm successively), electronic barrier layer TCTA(5nm), luminescent layer (15nm) is that doping agent, compound (1) are material of main part with CSA, the doping mass concentration is 0.1%, electron transfer layer TPBI(45nm), electron injecting layer LiF(1nm), Al negative electrode (100nm).Keep-up pressure in evaporate process is 5 * 10
-6Pa.This device cut-in voltage is 3.8V, high-high brightness 814cd m
-2, maximum current efficient 0.38cd A
-1, maximum power efficiency 0.27lm W
-1, luminous peak position is white light emission between 400～700nm.And work as brightness from 1000cd m
-2(8V) change to 5000cd m
-2In the time of (10V), the CIE coordinate is changed to (0.36,0.34) by (0.39,0.33), still keeps white light emission.
Embodiment 6: and luminescent device [ITO/NPB/TCTA/(2): CSA (0.1%)/Bepp
2/ LiF/Al]
Be coated with on the glass substrate of ito anode evaporation hole transmission layer NPB(40nm successively), electronic barrier layer TCTA(5nm), luminescent layer (15nm) is that doping agent, compound (2) are material of main part with CSA, and the doping mass concentration is 0.1%, electron transfer layer Bepp
2(45nm), electron injecting layer LiF(1nm), Al negative electrode (100nm).Keep-up pressure in evaporate process is 5 * 10
-6Pa.This device cut-in voltage is 3.0V, high-high brightness 4580cd m
-2, maximum current efficient 1.70cd A
-1, maximum power efficiency 1.72lm W
-1, luminous peak position is the white light color development between 400～750nm.And work as brightness from 1000cd m
-2(6V) change to 4000cd m
-2In the time of (9V), the CIE coordinate is changed to (0.30,0.38) by (0.30,0.37), still keeps white light emission.
Claims (5)
1. quinazoline derivant, its structural formula is as follows:
2. the application of the described quinazoline derivant of claim 1 in organic electroluminescence device.
3. the application of quinazoline derivant as claimed in claim 1 in organic electroluminescence device is characterized in that: compound (1) is for the preparation of the blue-ray organic electroluminescent device.
4. the application of quinazoline derivant as claimed in claim 1 in organic electroluminescence device is characterized in that: compound (2) is for the preparation of the blue green light organic electroluminescence device.
5. the application of quinazoline derivant as claimed in claim 1 in organic electroluminescence device is characterized in that: compound (1) or compound (2) and camphorsulfonic acid doping evaporation are for the preparation of white light organic electroluminescent device.
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| CN2013101817759A CN103242299A (en) | 2013-05-16 | 2013-05-16 | Quinazoline derivative and application thereof in organic electroluminescent device |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103467447A (en) * | 2013-09-04 | 2013-12-25 | 吉林奥来德光电材料股份有限公司 | Novel organic electroluminescent (EL) material and application thereof in devices |
| TWI766230B (en) * | 2019-01-21 | 2022-06-01 | 機光科技股份有限公司 | Organic compound and organic electroluminescence device using the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435003A (en) * | 1980-01-31 | 1984-03-06 | Ciba-Geigy Corporation | Chromogenic quinazolines |
-
2013
- 2013-05-16 CN CN2013101817759A patent/CN103242299A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435003A (en) * | 1980-01-31 | 1984-03-06 | Ciba-Geigy Corporation | Chromogenic quinazolines |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103467447A (en) * | 2013-09-04 | 2013-12-25 | 吉林奥来德光电材料股份有限公司 | Novel organic electroluminescent (EL) material and application thereof in devices |
| CN103467447B (en) * | 2013-09-04 | 2015-10-28 | 吉林奥来德光电材料股份有限公司 | One class electroluminescent organic material and applying in the devices |
| TWI766230B (en) * | 2019-01-21 | 2022-06-01 | 機光科技股份有限公司 | Organic compound and organic electroluminescence device using the same |
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Application publication date: 20130814 |