CN103420910A - Electron-transport blue luminescent material and use thereof - Google Patents
Electron-transport blue luminescent material and use thereof Download PDFInfo
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- CN103420910A CN103420910A CN2012102614333A CN201210261433A CN103420910A CN 103420910 A CN103420910 A CN 103420910A CN 2012102614333 A CN2012102614333 A CN 2012102614333A CN 201210261433 A CN201210261433 A CN 201210261433A CN 103420910 A CN103420910 A CN 103420910A
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- electron
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- acridine
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Abstract
The invention relates to the technical of organic electroluminescence and especially relates to an electron-transport blue luminescent material and its use in the field of organic electroluminescence. According to the electron-transport blue luminescent material, an aromatic compound or an aromatic heterocycle is connected to a 9th site of acridine, and because of high steric hindrance, the aromatic rings distortion-interact with each other so that the whole molecule has a non-planar structure and thus intermolecular aggregation and interaction are avoided and a wide band gap is formed; and the acridine group has a unique nitrogen-containing three-ring structure so that high fluorescence quantum efficiency and electron transmission performances are obtained. An experiment result shows that the electron-transport blue luminescent material has good heat stability and electroluminescent characteristics, can be used as a luminescent layer of a blue organic electroluminescent device and can efficiently emit blue light having high color purity.
Description
Technical field
The present invention relates to the organic electroluminescent field, be particularly related to a kind of for organic electroluminescence device (OLED, be Organic Light-Emitting Diode) the electron-transporting blue emitting material, and the application of this material in the organic electroluminescent field.
Background technology
The organic electroluminescent phenomenon is found existing three times more than ten years, and before 1987, the great drawback (cut-in voltage>200V) due to organic electroluminescence device, limited its application.Due to the continuous breakthrough of material devices technique, organic electroluminescent has been reached or approach practical stage nearly ten years.
Due to all circles' input and effort for many years, the development of OLED on basic science had greatly development, the emerging technology that but organic electroluminescence device is recent two decades to grow up, still there are many key issues really not solved, mainly that aspects such as optimization, colorize technology, high resolution technique of display, active actuation techniques and encapsulation technology at luminescent material still exist great underlying issue, make the life-span of organic electroluminescence device short, efficiency is lower.
Material for organic electroluminescence device mainly comprises electrode materials, carrier transmission material, luminescent material.Electrode materials is divided into cathode material and anode material, and carrier transmission material comprises electron transport material and hole mobile material, and wherein luminescent material is most important material in OLED.Realize the colored three kinds of colour light emittings of red, green, blue that need high-level efficiency and high color purity that show.With redgreenblue luminescence display material in, red and green luminescent material stable performance, long service life, met practical needs; And known a lot of blue material can meet the requirement that Full-color OLED shows on purity of color, but the life-span of its device need to improve, still do not possess practical condition.
In order to promote the performance of organic electroluminescence device, very important to the research of luminescent material.Select luminescent material must meet 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; 5, good carrier mobility.In general, because blue light material has wider band gap, be difficult to meet the requirement of blue light material to high-level efficiency and high color purity simultaneously.The balance of these two aspects of how to do well, become the key of developing outstanding blue light material.The compound that contains acridyl, be typical electron deficiency system, has the good electronic capability of accepting, and has good electronic transport property.Therefore the acridyl of introducing electron deficiency on the aromatic compound basis is connected, and is hopeful to obtain high efficiency blue emitting material.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of for organic electroluminescence device, can meet the requirement that Full-color OLED shows, can obtain purity of color is high and efficiency is high electron-transporting blue emitting material and application thereof.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of electron-transporting blue emitting material, structural formula as shown in Equation 1:
R wherein
1～R
8Be selected from hydrogen base or (C
1～C
30) any one in alkyl;
One of group that Ar is structure shown in formula 2:
Wherein, R is selected from any one in following group:
The alkyl of hydrogen, random length; Perhaps,
The group of the aromatic compound of benzene, biphenyl, naphthalene, anthracene, phenanthrene or pyrene; Perhaps,
Derived from aromatic heterocyclic group.
Further, preferably, R represents hydrogen, C
1～C
30The group of alkyl, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles or carbazole in any one.
The invention has the beneficial effects as follows:
1. this material is to connect aromatic compound or heteroaromatic at 9 of acridine, and higher steric hindrance makes between aromatic ring aligned twisted mutually, and whole molecule becomes nonplanar structure, avoids intermolecular gathering and interaction, and has wider band gap.In addition, the acridine group is owing to having unique nitrogenous tricyclic structure, it is had very high fluorescence quantum efficiency and electronic transmission performance.
2. this material has good thermostability, and second-order transition temperature and decomposition temperature are all very high.
3. this material has good electroluminescence characters, and the luminescent layer as blue organic electroluminescent device, can obtain the blue emission that purity of color and efficiency are very high.
5. this material can, as the doped body material of blue emitting material, have potentiality red and green application simultaneously.
The preparation method of electron-transporting blue emitting material of the present invention, comprise the steps:
By 3 of 2,7-dibromo spiral shell fluorenes, replacement, 2 of 6-dibromo carbazole and replacement, 7-dibromo fluorenes reacts and makes the compound shown in above-mentioned formula 1 with the 9-acridine boric acid generation Suzuki of replacement.
Wherein, in above-mentioned steps, the Suzuki reaction is under the protection of nitrogen or other rare gas elementes, with Pd (PPh
3)
4Or palladium is catalyzer, under the condition of 80～100 ℃, back flow reaction is 12～36 hours.
The present invention preferentially chooses compound 1～9 for representative materials, and their structural formula is as follows:
The present invention has synthesized a series of new compounds based on the acridine group, the acridine group is owing to having unique nitrogenous tricyclic structure, it the is had performance of some fluorescence dye, the spiral shell fluorenes, carbazole or the fluorene group that have larger conjugated structure by introducing enlarge its molecular conjugation degree, improve second-order transition temperature, increase molecular heat stability, in addition, the acridine group is typical electron deficiency system, have the good electronic capability of accepting, therefore electron-transporting blue emitting material provided by the invention has good photoelectric property.
It is example that compound 1 and 9 is take in the present invention, and the present invention also provides the application example of above-mentioned electron-transporting blue emitting material for the organic electroluminescent field.Prepared blue organic electroluminescent device generally comprises ITO Conducting Glass (anode), the hole transmission layer [N of stack successively, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines (NPB)], luminescent layer is [separately or with 9,9'-(1, the 3-phenyl) two-9H-carbazole (MCP) doping is used], electron transfer layer [1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) benzene (TPBI)], electron injecting layer (LiF) and cathode layer (Al).The all functions layer all can adopt vacuum evaporation or solution film forming technique.In this device, the molecular structural formula of organic compound more used is as follows:
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, such as hole transmission layer can be used N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4, the replacements such as 4'-diamines (TPD), electron transfer layer can be with 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) benzene (TPBI), three (oxine) aluminium (Alq3), 4,7-phenylbenzene-1, the replacements such as 10-phenanthroline (BPhen).The molecular structural formula of above material is as follows:
The accompanying drawing explanation
Fig. 1 is usingd compound 1 as the luminescent layer of blue organic electroluminescent device, the voltage-to-current density-brightness curve of device;
Fig. 2 is usingd compound 1 as the luminescent layer of blue organic electroluminescent device, the current density-power efficiency of device-luminous efficiency curve;
Fig. 3 is usingd compound 1 as the luminescent layer of blue organic electroluminescent device, and device is reaching 100cd/m
2The time electroluminescent spectrum figure;
Fig. 4 is usingd compound 9 as the luminescent layer of blue organic electroluminescent device, the voltage-to-current density-brightness curve of device;
Fig. 5 is usingd compound 9 as the luminescent layer of blue organic electroluminescent device, the current density-power efficiency of device-luminous efficiency curve;
Fig. 6 is usingd compound 9 as the luminescent layer of blue organic electroluminescent device, and device is reaching 100cd/m
2The time electroluminescent spectrum figure;
Embodiment
Below in conjunction with accompanying drawing, principle of the present invention and feature are described, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Embodiment prepared by compound sample:
Add 1.19g 2 in there-necked flask, 7-dibromo spiral shell fluorenes (2.5mmo l) and 1.77g9-acridine boric acid (7.5mmol), dissolve (70mL toluene, 35mL ethanol) with mixed solvent, then adds 50mL Na
2CO
3The aqueous solution (2M), logical nitrogen gas stirring 1 hour, to remove the oxygen in reaction flask.Then add Pd (PPh
3)
40.183g(0.16mmol), under strong stirring, refluxing, reaction process is controlled by thin-layer chromatography.After reaction 24h, add the 50mL deionized water in reaction solution, remove by filter insolubles, water is separated with organic phase, dichloromethane extraction for water (20mL * 3), after organic phase is mixed, underpressure distillation is concentrated to about 5mL, and column chromatography is separated, eluent methylene dichloride: normal hexane=1:5(volume ratio), obtain 1.45g yellow solid (for target product).Thick product is purified through distillation, and obtaining straight product 0.96g(productive rate is 57%).
MS(m/z):670.3。Ultimate analysis (C
51H
30N
2): theoretical value C:91.32, H:4.51, N:4.18, measured value C:91.55, H:4.30, N:4.05.
Embodiment 22,7-bis-(1,2,3,4,5,6,7,8-prestox acridyl) spiral shell fluorenes (compound 2)
With 2,7-dibromo spiral shell fluorenes and 1,2,3,4,5,6,7,8-prestox-9-acridine boric acid, be the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):894.6。Ultimate analysis (C
67H
62N
2): theoretical value C:89.89, H:6.98, N:3.13, measured value C:89.65, H:3.21, N:3.08.
Embodiment 33,6-bis-acridyl carbazoles (compound 3)
With 3,6-dibromo carbazole and 9-acridine boric acid, be the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):521.8。Ultimate analysis (C
38H
23N
3): theoretical value C:87.50, H:4.44, N:8.06, measured value C:87.56, H:4.31, N:8.12.
Embodiment 4 N-methyl-3,6-bis-acridyl carbazoles (compound 4)
With N-methyl-3,6-dibromo carbazole and 9-acridine boric acid are the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):535.7。Ultimate analysis (C
39H
25N
3): theoretical value C:87.45, H:4.70, N:7.84, measured value C:87.66, H:4.84, N:7.72.
Embodiment 5 N-phenyl-3,6-bis-acridyl carbazoles (compound 5)
With N-phenyl-3,6-dibromo carbazole and 9-acridine boric acid are the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):597.3。Ultimate analysis (C
44H
27N
3): theoretical value C:88.42, H:4.55, N:7.03, measured value C:88.38, H:4.47, N:7.12.
Embodiment 72,7-bis-acridyl fluorenes (compound 7)
With 2,7-dibromo fluorenes and 9-acridine boric acid, be the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):520.6。Ultimate analysis (C
39H
24N
2): theoretical value C:89.97, H:4.65, N:5.38, measured value C:89.78, H:4.67, N:5.43.
Embodiment 82,7-bis-acridyls-9,9-dimethyl fluorene (compound 8)
Bromo-9 with 2,7-bis-, 9-dimethyl fluorene and 9-acridine boric acid are the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):548.9。Ultimate analysis (C
41H
28N
2): theoretical value C:89.75, H:5.14, N:5.11, measured value C:89.80, H:5.05, N:5.07.
Embodiment 92,7-bis-acridyls-9,9-diphenylfluorene (compound 9)
Bromo-9 with 2,7-bis-, 9-diphenylfluorene and 9-acridine boric acid are the synthetic method preparation of starting raw material by compound 1 in embodiment 1.
MS(m/z):672.8。Ultimate analysis (C
51H
32N
2): theoretical value C:91.04, H:4.79, N:4.16, measured value C:91.00, H:4.84, N:4.08.
Organic electroluminescence device embodiment:
The application in organic electroluminescence device as luminescent layer of device embodiment 1 compound 1
The present embodiment prepares the electron-transporting blue organic electroluminescent device by the following method:
A) clean the ITO(tin indium oxide) glass: use respectively deionized water, acetone, ethanol ultrasonic cleaning ito glass respectively 15 minutes, then process 2 minutes in the plasma clean device;
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 compound 1, thickness is 30nm;
D) on luminescent layer, vacuum evaporation electron transfer layer TPBI, thickness is 30nm;
E) on electron transfer layer TPBI, vacuum evaporation electron injecting layer LiF, thickness 1nm;
F) on electron injecting layer LiF, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device is ITO/NPB (50nm)/compound 1 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm).Compound 1 prepared by the embodiment 1 of usining is as the luminescent layer of this device, and as shown in Figure 1, current density-power efficiency-the luminous efficiency curve as shown in Figure 2 for the voltage-to-current density-brightness curve of this device.The bright voltage that opens of device is 5.5V, and high-high brightness reaches 3136cd/m
2, maximum current efficiency reaches 0.44cd/A.Fig. 3 is that device is at 100cd/m
2The time electroluminescent spectrum figure, the CIE coordinate is positioned at (0.18,0.14).
The application in organic electroluminescence device as luminescent layer of device embodiment 2 compounds 9
The present embodiment prepares the electron-transporting blue organic electroluminescent device by the following method:
A) clean the ITO(tin indium oxide) glass: use respectively deionized water, acetone, ethanol ultrasonic cleaning ito glass respectively 15 minutes, then process 2 minutes in the plasma clean device;
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 compound 9, thickness is 30nm;
D) on luminescent layer, vacuum evaporation electron transfer layer TPBI, thickness is 30nm;
E) on electron transfer layer TPBI, vacuum evaporation electron injecting layer LiF, thickness 1nm;
F) on electron injecting layer LiF, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device is ITO/NPB (50nm)/compound 9 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm).Using compound 9 as the luminescent layer of this device, and as shown in Figure 4, current density-power efficiency-the luminous efficiency curve as shown in Figure 5 for the voltage-to-current density-brightness curve of this device.The bright voltage that opens of device is 4.5V, and high-high brightness reaches 6860cd/m
2, maximum current efficiency is brought up to 0.951cd/A.Fig. 6 is that this device is at 100cd/m
2The time electroluminescent spectrum figure, the CIE coordinate is positioned at (0.15,0.12).
The foregoing is only preferred embodiment of the present invention, in order to limit the present invention, within the spirit and principles in the present invention not all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (3)
1. an electron-transporting blue emitting material, is characterized in that, its structural formula is as follows:
R wherein
1～R
8Be selected from respectively hydrogen or (C
1～C
30) any one in alkyl;
One of group that Ar is following structure:
Wherein, R is selected from any one in following group:
The alkyl of hydrogen, random length; Perhaps,
The group of the aromatic compound of benzene, biphenyl, naphthalene, anthracene, phenanthrene or pyrene; Perhaps,
Derived from aromatic heterocyclic group.
2. electron-transporting blue emitting material according to claim 1, is characterized in that, R is preferably from hydrogen, C
1～C
30The group of alkyl, benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles or carbazole in any one.
3. the purposes using the arbitrary described electron-transporting blue emitting material of claim 1 to 2 as electroluminescent organic material.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104109532A (en) * | 2014-04-03 | 2014-10-22 | 烟台万润精细化工股份有限公司 | Electron transfer material and its application |
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
| CN109912433A (en) * | 2019-03-07 | 2019-06-21 | 北京诚志永华显示科技有限公司 | New compound, electroluminescent organic material, organic electroluminescence device, electronic device |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104109532A (en) * | 2014-04-03 | 2014-10-22 | 烟台万润精细化工股份有限公司 | Electron transfer material and its application |
| CN104109532B (en) * | 2014-04-03 | 2016-01-06 | 中节能万润股份有限公司 | A kind of electron transport material and application thereof |
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
| CN109912433A (en) * | 2019-03-07 | 2019-06-21 | 北京诚志永华显示科技有限公司 | New compound, electroluminescent organic material, organic electroluminescence device, electronic device |
| CN109912433B (en) * | 2019-03-07 | 2022-04-08 | 石家庄诚志永华显示材料有限公司 | Compound, organic electroluminescent material, organic electroluminescent device, and electronic device |
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