CN102167971A - Blue-fluorescence luminescent material and application thereof - Google Patents
Blue-fluorescence luminescent material and application thereof Download PDFInfo
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- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 125000005561 phenanthryl group Chemical group 0.000 abstract description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 abstract 1
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- BDRNQFCOAVNMOX-UHFFFAOYSA-N Brc(cc1)cc(C23c4ccccc4C4C=CC=CC24)c1-c(cc1)c3cc1Br Chemical compound Brc(cc1)cc(C23c4ccccc4C4C=CC=CC24)c1-c(cc1)c3cc1Br BDRNQFCOAVNMOX-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a blue-fluorescence luminescent material and application thereof. In the blue-fluorescence luminescent material, spirobifluorene is used as the center to connect two phenanthryl groups so as to form a distorted non-planar structure, thereby avoiding intermolecular aggregation and having high fluorescence quantum efficiency. The blue-fluorescence luminescent material has high thermal stability and favorable electroluminescent characteristic, and blue light emission with very high color purity and efficiency can be obtained when the blue-fluorescence luminescent material is used as a light emitting layer of a blue organic electroluminescent device.
Description
Technical field
The present invention relates to a kind of blue-fluorescence luminescent material, particularly a kind of blue-fluorescence luminescent material that is used for organic electroluminescence device (OLED), and the application of this material in the blue-fluorescence organic electroluminescence device.
Background technology
Organic electroluminescence device is considered to the nova of ultra-thin flat-panel display devices of future generation.Because it has that the material range of choice is wide, response speed is fast, face is luminous, full-color demonstration, driving voltage are low, can realize plurality of advantages such as flexible demonstration, must will become the strong rival of liquid-crystal display, plasma display etc.Though having many research institutions and company to drop into a large amount of energy, the present whole world removes to research and develop organic electroluminescence device, but compare with people's expection, its industrialization level also differs greatly, and wherein, has only small-sized mobile phone display screen that the organic electroluminescent technology is used better.Trace it to its cause,, still have many key issues really not solved in the organic electroluminescent field, as aspects such as purity of color, stability of photoluminescence, the actuation techniques of having chance with and encapsulation technologies, also exist certain problem, make that the life-span of organic electroluminescence device is short, efficient is lower.
In order to promote the performance of organic electroluminescence device, very important to the research of luminescent material.Select luminescent material must satisfy following requirement: 1, the fluorescent characteristic of high-quantum efficiency; 2, good characteristic of semiconductor; 3, good film-forming properties and thermostability; 4, good light stability.In the OLED investigation of materials, the performance of green glow and red light material is very outstanding, can reach commercial requirement at present, and the research of blue light material is then relatively weak, and this is also restricting the development based on the luminous full-color demonstration of OLED of red green blue tricolor.In general, because blue light material has the band gap of broad, be difficult to satisfy simultaneously the requirement of blue light material to high-level efficiency and high color purity.How to carry out the balance of these two aspects, become the key of the outstanding blue light material of exploitation.
Though a lot of OLED blue emitting materials have been arranged at present, and the blue light material with high-level efficiency and high color purity is actually rare.
Summary of the invention
One object of the present invention is to provide a kind of compound that can be used as blue-fluorescence luminescent material, and this compound is used for organic electroluminescence device, can obtain the very high blue emission of purity of color and efficient.
Second purpose of the present invention provides the application of above-mentioned blue-fluorescence luminescent material in organic electroluminescence device.
Blue-fluorescence luminescent material of the present invention is a structural formula suc as formula 1 or formula 2 shown in compound, abbreviate DPSBF as:
Wherein R1～R9 and R
1'～R
9' be hydrogen, and four carbon contain oxyalkyl with interior alkyl.
The preparation method of above-mentioned blue-fluorescence luminescent material comprises the steps:
By 2,7-dibromo spiral shell two fluorenes or 2, the Suzuki reaction of 2 '-dibromo spiral shell, two fluorenes and replacement phenanthryl-9-boric acid makes the compound shown in formula 1 or the formula 2.
Wherein, in above-mentioned steps, 2,7-dibromo spiral shell two fluorenes or 2,2 '-dibromo spiral shell, two fluorenes and replacement phenanthryl-9-boric acid are under the protection of nitrogen or rare gas element, with Pd (PPh
3)
4Or palladium is catalyzer, under 80-100 ℃ condition back flow reaction 12-36 hour.
With R1～R9 and R
1'～R
9' to be hydrogen be example, 2,7-dibromo spiral shell two fluorenes and replacing shown in the reaction process following (a) that phenanthryl-9-boric acid prepares the first blue-fluorescence luminescent material DPSBF1,2,2 '-dibromo spiral shell, two fluorenes and replacing shown in the reaction process following (b) that phenanthryl-9-boric acid prepares the second blue-fluorescence luminescent material DPSBF2:
Reaction process
Improve the purity of color of luminescent material, must suppress the pi-conjugated system of intramolecularly, reduce the conjugation degree.The present invention adopts that non-coplanar spiral shell is fluorene structured to be connected with the less phenanthryl of conjugation degree, has obtained having twist structured blue-fluorescence luminescent material DPSBF.This blue-fluorescence luminescent material has very high fluorescence quantum efficiency and purity of color.
Above-mentioned blue-fluorescence luminescent material provided by the invention can be used for the luminescent layer of blue organic electroluminescent device.Prepared blue organic electroluminescent device generally comprises synergetic successively ITO Conducting Glass (anode), hole transmission layer (NPB), luminescent layer (the independent or use of mixing of DPSBF), electron transfer layer (PBD), electron transfer layer (Alq3), electron injecting layer (LiF) and cathode layer (Al).The all functions layer all can adopt vacuum evaporation or solution film forming technology.The molecular structural formula of more used organic compound is as follows in this device:
Certainly, the functional layer of device of the present invention is not limited to use above-mentioned materials, and these materials can replace with other materials, can be with replacements such as TPD such as hole transmission layer, and electron transfer layer can be used replacements such as BPhen, TPBI.The molecular structural formula of these materials is as follows:
Blue fluorescent material of the present invention is applied in the blue organic electroluminescent device, demonstrates very high purity of color, and the major advantage of this material is:
1) this material employing is the center with spiral shell two fluorenes, connect two phenanthryl, form the distortion nonplanar structure, effectively avoided intermolecular gathering, has higher fluorescence quantum efficiency, with tonka bean camphor C102 is benchmark, and recording the fluorescence quantum efficiency of compound (1) in chloroform solvent is 0.94, and the fluorescence quantum efficiency of compound (2) in chloroform solvent is 0.90.
2) this material has good thermostability, and decomposition temperature is up to 400 ℃.
This material has good electroluminescence characters, is the blue organic electroluminescent device of luminescent material preparation with compound (1), and the emission wavelength of device is 436nm, and the CIE coordinate is (0.15,0.08), very near the standard blueness (0.14,0.08) of NTSC.
Description of drawings
Fig. 1 is uv-visible absorption spectra and the fluorescence emission spectrum of DPSBF1 in chloroformic solution according to embodiment 1 preparation;
Fig. 2 be among the embodiment 3 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, the voltage-to-current density-brightness curve of device;
Fig. 3 be among the embodiment 3 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, the current density-current efficiency of device-luminous efficiency curve;
Fig. 4 be among the embodiment 3 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, device is reaching 100cd/m
2The time electroluminescent spectrum figure;
Fig. 5 be among the embodiment 4 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, the voltage-to-current density-brightness curve of device;
Fig. 6 be among the embodiment 4 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, the current density-current efficiency of device-luminous efficiency curve;
Fig. 7 be among the embodiment 4 with the luminescent layer of DPSBF1 as the blue-fluorescence organic electroluminescence device, device is reaching 100cd/m
2The time electroluminescent spectrum figure;
Fig. 8 be among the embodiment 5 with the luminescent layer of DPSBF2 as the blue-fluorescence organic electroluminescence device, the voltage-to-current density-brightness curve of device;
Fig. 9 be among the embodiment 5 with the luminescent layer of DPSBF2 as the blue-fluorescence organic electroluminescence device, the current density-current efficiency of device-luminous efficiency curve;
Figure 10 be among the embodiment 5 with the luminescent layer of DPSBF2 as the blue-fluorescence organic electroluminescence device, device is reaching 100cd/m
2The time electroluminescent spectrum figure.
Embodiment
Below each embodiment further specify content of the present invention, but should not be construed as limitation of the present invention.
Preparation and the character one of embodiment 1 blue-fluorescence luminescent material DPSBF1 (formula 1)
1) the synthetic first blue-fluorescence luminescent material DPSBF1 (formula 1)
Add 1.314g 2 in there-necked flask, 7-dibromo spiral shell fluorenes (2.773mmol) and 1.353g phenanthrene-9-boric acid (6.097mmol) with mixed solvent dissolving (100mL toluene, 50mL ethanol), adds 50mL Na then
2CO
3The aqueous solution (2M), logical nitrogen stirs 1h to remove the oxygen in the reaction flask.Add Pd (PPh then
3)
40.710g (0.614mmol), the powerful stirring down refluxed, and reaction process is controlled by TLC.Behind the reaction 24h, in reaction solution, add the 50mL deionized water, remove by filter insolubles, water is separated water CH with organic phase
2Cl
2Extraction (20mL is each, 3 times) mixes underpressure distillation later on organic phase and is concentrated to about 5mL, and column chromatography separates, eluent CH
2Cl
2: hexane (1: 4).Obtain the 1.362g white solid.The 280 ℃ of distillations in CVD of thick product are purified, and obtain straight product 0.865g (productive rate is 46.7%).
1H?NMR(CDCl
3，TMS，δ)：8.70(d，2H)，8.65(d，2H)，8.05(d，2H)，7.81(d，4H)，7.75(d，2H)，7.54-7.63(m，10H)，7.44(t，2H)，7.34(t，2H)，7.19(t，2H)，7.00(d，2H)，6.96(s，2H).
2) uv-visible absorption spectra of DPSBF1 and fluorescence spectrum
Uv-visible absorption spectra is as shown in Figure 1 under solution state for prepared DPSBF1.The absorption spectrum of this DPSBF1 in chloroformic solution has a maximum absorption band that is positioned at 254nm, also has two small peaks, the phenanthryl structure in the corresponding molecule at 310nm and 327nm place simultaneously.The fluorescence emission peak of this DPSBF1 is positioned at 383nm, for bluish voilet luminous.
The preparation of embodiment 2 second blue-fluorescence luminescent material DPSBF2 (formula 2)
1) the synthetic second blue-fluorescence luminescent material DPSBF2 (formula 2)
Add 1.015g 2 in there-necked flask, 2 '-dibromo spiral shell fluorenes (2.142mmol) and 1.045g phenanthrene-9-boric acid (4.707mmol) with mixed solvent dissolving (100mL toluene, 50mL ethanol), adds 50mL Na then
2CO
3The aqueous solution (2M), logical nitrogen stirs 1h to remove the oxygen in the reaction flask.Add Pd (PPh then
3)
40.550g (0.474mmol), the powerful stirring down refluxed, and reaction process is controlled by TLC.Behind the reaction 24h, in reaction solution, add the 50mL deionized water, remove by filter insolubles, water is separated water CH with organic phase
2Cl
2Extraction (20mL is each, 3 times) mixes underpressure distillation later on organic phase and is concentrated to about 5mL, and column chromatography separates, eluent CH
2Cl
2: hexane (1: 4).Obtain the 1151g white solid.The 280 ℃ of distillations in CVD of thick product are purified, and obtain straight product 0.635g (productive rate is 44.4%).
1H?NMR(CDCl
3，TMS，δ)：8.73(d，2H)，8.67(d，2H)，7.92(d，4H)，7.73(s，2H)，7.61-7.68(m，12H)，7.47(t，2H)，7.33(d，2H)，7.25(t，2H)，7.08(t，2H)，7.02(t，2H).
The application one of embodiment 3 first blue-fluorescence luminescent material DPSBF1 in organic electroluminescence device
Present embodiment prepares the blue-fluorescence organic electroluminescence device according to following method:
A) clean ITO (tin indium oxide) glass: used deionized water, acetone, ethanol ultrasonic cleaning ito glass respectively respectively 15 minutes, and in the plasma clean device, handled 2 minutes then;
B) vacuum evaporation or solution film forming hole transmission layer NPB on the anode ito glass, thickness is 50nm;
C) on hole transmission layer NPB, vacuum evaporation luminescent layer DPSBF1, thickness are 30nm;
D) on luminescent layer DPSBF1, vacuum evaporation electron transfer layer PBD, thickness are 10nm;
E) on hole blocking layer PBD, vacuum evaporation electron transfer layer Alq
3, thickness 20nm;
F) at electron transfer layer Alq
3On, vacuum evaporation electron injecting layer LiF, thickness 0.5nm;
G) on electron injecting layer LiF, vacuum evaporation negative electrode Al, thickness are 100nm.
The structure of device is ITO/NPB (50nm)/DPSBF (30nm)/PBD (10nm)/Alq
3(20nm)/LiF (0.5nm)/Al (100nm).With the DPSBF1 of embodiment 1 preparation luminescent layer as this device, the voltage-to-current density-brightness curve of this device as shown in Figure 2, current density-the current efficiency curve is as shown in Figure 3.The bright voltage that opens of device is 5.5V, and high-high brightness reaches 1916cd/m
2, maximum current efficient 1.24cd/A.Fig. 4 is that this device is at 100cd/m
2The time electroluminescent spectrum figure, the CIE coordinate is positioned at (0.15,0.08).
The application two of embodiment 4 first blue-fluorescence luminescent material DPSBF1 in organic electroluminescence device
Present embodiment prepares the blue-fluorescence organic electroluminescence device according to following method:
A) clean ITO (tin indium oxide) glass: used deionized water, acetone, ethanol ultrasonic cleaning ito glass respectively respectively 15 minutes, and in the plasma clean device, handled 2 minutes then;
B) vacuum evaporation or solution film forming hole transmission layer NPB on the anode ito glass, thickness is 50nm;
C) on hole transmission layer NPB, vacuum evaporation luminescent layer DPSBF1, thickness are 30nm;
D) on luminescent layer DPSBF1, common evaporation electron transfer layer PBD and Alq
3, the speed ratio of control PBD and Alq3 is 1: 2, thickness is 30nm;
E) at PBD﹠amp; Alq
3On, vacuum evaporation electron injecting layer LiF, thickness are 0.5nm;
F) on electron injecting layer LiF, vacuum evaporation negative electrode Al, thickness are 100nm.
The structure of device is ITO/NPB (50nm)/DPSBF (30nm)/PBD: Alq
3(1: 2,30nm)/LiF (0.5nm)/Al (100nm).With the DPSBF1 of embodiment 1 preparation luminescent layer as this device, the voltage-to-current density-brightness curve of this device as shown in Figure 5, current density-the current efficiency curve is as shown in Figure 6.The bright voltage that opens of device is 5V, and high-high brightness reaches 3794cd/m
2, maximum current efficient is brought up to 1.38cd/A.Fig. 7 is that device is at 100cd/m
2The time electroluminescent spectrum figure, the CIE coordinate is positioned at (0.16,0.12).
The application three of embodiment 5 second blue-fluorescence luminescent material DPSBF2 in organic electroluminescence device
Present embodiment prepares the blue-fluorescence organic electroluminescence device according to following method:
A) clean ITO (tin indium oxide) glass: used deionized water, acetone, ethanol ultrasonic cleaning ito glass respectively respectively 15 minutes, and in the plasma clean device, handled 2 minutes then;
B) vacuum evaporation or solution film forming hole transmission layer NPB on the anode ito glass, thickness is 50nm;
C) on hole transmission layer NPB, common evaporation luminescent layer DPSBF2 and MADN, thickness is 10nm, the doping ratio of MADN is 1%;
D) on doping luminescent layer DPSBF2 and MADN, vacuum evaporation electron transfer layer PBD, thickness are 50nm;
E) on electron transfer layer PBD, vacuum evaporation electron injecting layer LiF, thickness are 0.5nm;
F) on electron injecting layer LiF, vacuum evaporation negative electrode Al, thickness are 100nm.
The structure of device is ITO/NPB (50nm)/DPSBF: 1%wtMADN (10nm)/PBD (50nm)/LiF (0.5nm)/Al (100nm).DPSBF2 with embodiment 2 preparation is a luminescent layer, the voltage-to-current density-brightness curve of this device as shown in Figure 5, current density-the current efficiency curve is as shown in Figure 6.The bright voltage that opens of device is 3V, and high-high brightness reaches 800cd/m
2, maximum current efficient is brought up to 1.97cd/A.Fig. 7 is that device is at 100cd/m
2The time electroluminescent spectrum figure, the CIE coordinate is positioned at (0.15,0.08).
It should be noted that at last the purpose of publicizing and implementing example is to help further to understand the present invention, but it will be appreciated by those skilled in the art that: without departing from the spirit and scope of the invention and the appended claims, various substitutions and modifications all are possible.Therefore, the present invention should not be limited to the disclosed content of embodiment, and the scope of protection of present invention is as the criterion with the scope that claims define.
Claims (4)
1. blue-fluorescence luminescent material, suc as formula 1 or formula 2 shown in:
Formula 1 formula 2
In formula 1 and the formula 2, R1～R9 and R
1'～R
9' be hydrogen, and 1-4 carbon contains oxyalkyl, amido and itrile group with interior alkyl.
2. the described blue-fluorescence luminescent material of claim 1 is as the purposes of electroluminescent organic material.
3. a blue organic electroluminescent device is characterized in that, the material of its luminescent layer is the described blue-fluorescence luminescent material of claim 1.
4. a blue organic electroluminescent device is characterized in that, its luminescent layer mixes and uses blue-fluorescence luminescent material as claimed in claim 1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013498A (en) * | 2012-12-29 | 2013-04-03 | 上海师范大学 | Application of 2,7-di(triphenylamine diamine) spirobifluorene |
| CN112442052A (en) * | 2019-08-29 | 2021-03-05 | 南京高光半导体材料有限公司 | High-efficiency and long-life blue fluorescent doped material, application thereof and organic electroluminescent device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060040131A1 (en) * | 2004-08-19 | 2006-02-23 | Eastman Kodak Company | OLEDs with improved operational lifetime |
| US20060134425A1 (en) * | 2002-08-27 | 2006-06-22 | Canon Kabushiki Kaisha | Spiro compound and organic luminescence device using the same |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060134425A1 (en) * | 2002-08-27 | 2006-06-22 | Canon Kabushiki Kaisha | Spiro compound and organic luminescence device using the same |
| US20060040131A1 (en) * | 2004-08-19 | 2006-02-23 | Eastman Kodak Company | OLEDs with improved operational lifetime |
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| Title |
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| TOBAT P. I. SARAGI等: "Spiro Compounds for Organic Optoelectronics", 《CHEMICAL REVIEWS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013498A (en) * | 2012-12-29 | 2013-04-03 | 上海师范大学 | Application of 2,7-di(triphenylamine diamine) spirobifluorene |
| CN103013498B (en) * | 2012-12-29 | 2015-02-18 | 上海师范大学 | Application of 2,7-di(triphenylamine diamine) spirobifluorene |
| CN112442052A (en) * | 2019-08-29 | 2021-03-05 | 南京高光半导体材料有限公司 | High-efficiency and long-life blue fluorescent doped material, application thereof and organic electroluminescent device |
| CN112442052B (en) * | 2019-08-29 | 2022-08-26 | 南京高光半导体材料有限公司 | High-efficiency and long-life blue fluorescent doped material, application thereof and organic electroluminescent device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102167971B (en) | 2013-11-27 |
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