CN104817540B - A kind of phenanthro- imdazole derivatives and its application - Google Patents
A kind of phenanthro- imdazole derivatives and its application Download PDFInfo
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- 0 c(cc1)ccc1-c1nc(c(cccc2)c2c2*3cccc2)c3[n]1-c(cc1)ccc1-c1cnccc1 Chemical compound c(cc1)ccc1-c1nc(c(cccc2)c2c2*3cccc2)c3[n]1-c(cc1)ccc1-c1cnccc1 0.000 description 1
- UTJPZAKETHLLEK-UHFFFAOYSA-N c(cc1)ccc1-c1nc(c(cccc2)c2c2ccccc22)c2[n]1-c1cc(-c2cccnc2)ccc1 Chemical compound c(cc1)ccc1-c1nc(c(cccc2)c2c2ccccc22)c2[n]1-c1cc(-c2cccnc2)ccc1 UTJPZAKETHLLEK-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a kind of phenanthro- imdazole derivatives, with higher triplet energies, high glass transition temperature, and good electrons transmittability.When it is used as electron transport material, compared with the convention body material that electron transport material BCP commonly used in the prior art is electron transporting groups, the transmittability of electronics is significantly improved, in organic electroluminescence device, the compound is compared with traditional electron transport material in glass transition temperature, current efficiency, power efficiency, external quantum efficiency and aspect of roll-offing all increase significantly, and are preferable electron transport materials.
Description
Technical field
The invention belongs to field of photovoltaic materials, more particularly, to a kind of phenanthro- imdazole derivatives and its application.
Background technology
Organic electroluminescent phenomenon is found in 1963 earliest, at that time by the use of organic anthracene crystal as luminescent material, due to
The device drive voltage is up to 400V, and device efficiency and life-span are far away from inorganic electroluminescence device, and people is not caused at that time
Attention.1987, research group was first by Deng Qingyun (Tang, C.W.et al.Appl.Phys.Lett.1987,52,913)
Propose the OLED structure of organic multilayer non-crystal thin film；Nineteen ninety Burroughes et al. (Burroughes, J.H.et
Al.Nature.1990,347,539) polymer LED is reported first, organic electroluminescent research is entered since then
One brand-new stage.Nearly ten years, Organic Light Emitting Diode because with response is fast, brightness is high, the low advantage of operating voltage and
Be applied in high-quality flat-panel screens (Journal of the American Chemical Society, 2002,124,
11576；Journal of Display Technology,2005,1,90；Molecular Electronics and
Bioelectronics.2007,18,25)。
The OLED of excellent performance is obtained, first has to select mobility outstanding transmission material enough, it is ensured that sending out
Electron hole can be balanced in photosphere, but electron transport material is current very in short supply, Alq3With its preferable stability quilt
Extensive use, but be due to its relatively low mobility, it is difficult to prepare efficient OLED.
Existing electron transport material electron mobility still has much room for improvement, and development high-mobility electron transmission material is preparation
Efficient OLED is the focus that we study all the time.
The content of the invention
For the disadvantages described above or Improvement requirement of prior art, the invention provides a kind of phenanthro- imdazole derivatives and its should
With, its object is to provide the electron transport material that a kind of electron mobility is high, thus solve OLED electron transport material
Its electron mobility still technical problem to be improved.
To achieve the above object, according to one aspect of the present invention there is provided a kind of phenanthro- imdazole derivatives, it has formula
(I) structure：
Wherein, R1、R2、R3And R4For hydrogen atom or drawing electron group, R1、R2、R3And R4It is identical or different.
Preferably, described phenanthro- imdazole derivatives, its described drawing electron group is selected from following group：
Preferably, described phenanthro- imdazole derivatives, its described R3And R4For hydrogen atom.
It is another aspect of this invention to provide that there is provided a kind of application of the phenanthro- imdazole derivatives, it is used as luminous electricity
Sub- transmission material.
It is another aspect of this invention to provide that there is provided a kind of organic electroluminescence device, including multilayer organic material, wherein
Transport layer or emitting layer material include the phenanthro- imdazole derivatives.
In general, by the contemplated above technical scheme of the present invention compared with prior art, it can obtain down and show
Beneficial effect：
The compound with structure shown in logical formula (I) that the present invention is provided is that a class has higher triplet energies, high
Glass transition temperature, and good electrons transmittability.When its as electron transport material in use, and prior art
In the electron transport material BCP that commonly uses compared for the convention body materials of electron transporting groups, the transmittability of electronics has bright
Aobvious to improve, in organic electroluminescence device, the compound is compared with traditional electron transport material in glass transition temperature, electric current
Efficiency, power efficiency, external quantum efficiency and aspect of roll-offing all increase significantly, and are preferable electron transport materials.
Phenanthro- imidazoles electron transporting groups are used in fluorescent electronic transmission material by the present invention first, have synthesized a series of
Asymmetric electron transport material.For example, using CNPI-p3Py as electron transport material, the fluorescence Blue-light emitting host material of preparation, its
Device maximum current efficiency, power efficiency and external quantum efficiency have respectively reached 11.12cd/A, 7.23lm/w and 5.66%.
The material of synthesis has very high glass transition temperature, higher triplet energies, and has preferable hole and electric transmission energy
Power, shows superior efficiency in fluorescence blue-light device.
Brief description of the drawings
Fig. 1 is the synthetic route chart of phenanthro- imidazoles electron transport material；
Fig. 2 is that the electron transport material of embodiment 7 to 9 prepares device structural representation；
Fig. 3 is the luminance-current density vs. voltage performance diagram of the electron transport material of embodiment 10；
Fig. 4 is the device current efficiency of the electron transport material of embodiment 10 and the performance diagram of current density；
Fig. 5 is the electroluminescence characters curve map of the device of the electron transport material of embodiment 10；
Fig. 6 is pyridine substitution phenanthro- imidazoles electron transport material electron mobility curve.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, it is right below in conjunction with drawings and Examples
The present invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, and
It is not used in the restriction present invention.As long as in addition, technical characteristic involved in each embodiment of invention described below
Not constituting conflict each other can just be mutually combined.
The phenanthro- imdazole derivatives that the present invention is provided, it has formula (I) structure：
Wherein, R1、R2、R3And R4For hydrogen atom or drawing electron group, R1、R2、R3And R4It is identical or different.The drawing electronics
Group, preferably hales electron group, such as pyridine, pyrimidine, triazine, 1,2,4- thiadiazoles, benzimidazole, oxadiazoles, oxazole, three
Azoles, ferrosin etc..The drawing electron group is selected from following group：
Preferably, described its R of phenanthro- imdazole derivatives3And R4For hydrogen atom.It is highly preferred that stating phenanthro- imdazole derivatives R1
Selected from pyridine, pyrimidine, benzimidazole, R2Selected from pyridine, pyrimidine, benzimidazole, further, with following structure：
The phenanthro- imdazole derivatives that the present invention is provided can be made using phenanthrenequione as raw material by ring-closure reaction.Synthetic route
See Fig. 1, the synthetic route of phenanthro- imidazoles electron transport material, reaction condition：I) aniline, bromo benzaldehyde, potassium acetate, second
Acid, 120 DEG C, 12 hours；Ii) toluene, ethanol, wet chemical (2M), Pd (PPh3)4, 24 hours.
The phenanthro- imdazole derivatives that the present invention is provided, electron mobility can reach 10-3cm2V-1s-1Left and right, is greatly carried
The mobility of high electron transport material, as luminous electron transmission material, realizes carrier balance, so that the stabilization of device
Property and efficiency are all remarkably enhanced.
Invention also provides a kind of electroluminescent device, including multilayer organic material, wherein transport layer or luminescent layer
Material includes the phenanthro- imdazole derivatives that the present invention is provided.
It is embodiment below：
Embodiment 1
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1It is for pyridineR2It is former for hydrogen
Son, R3For hydrogen atom, R4For hydrogen atom；Its chemical name is 2- (4- (3- pyridines) phenyl) -1- phenyl -1H- [9,10-d] phenanthro-
Imidazoles, abbreviation CPI-p3Py, structural formula is as follows：
Its preparation method is as follows：Under condition of nitrogen gas protection, by compound 2- (4- bromophenyls) -1- phenyl -1H- [9,10-
D] phenanthro- imidazoles (1) (1.76g, 4.0mmol), 3- pyridine borates (0.50g, 4.0mmol), toluene (100ml), absolute ethyl alcohol
(50ml), 2M K2CO3(50ml) aqueous solution is sequentially added in two mouthfuls of round-bottomed flasks of dry 500ml, ultrasound 30 minutes, in nitrogen
Under conditions of, reaction is heated to 80 DEG C, is stirred at reflux 24 hours, question response is cooled to room temperature, dichloromethane (60ml) is added
Extraction three times, collects organic phase and is washed three times with water (50ml), and organic phase is dried 12 hours with anhydrous magnesium sulfate, filtering,
Column chromatography (solvent：Ethyl acetate and petroleum ether) obtain white solid 2- (4- (3- pyridines) phenyl) -1- phenyl -1H- [9,
10-d] phenanthro- imidazoles (CPI-p3Py) 1.53g.Yield：86%.1H-NMR(CDCl3,400MHz):δ (ppm) 8.937~8.918
(d, 1H), 8.854~8.849 (d, 1H), 8.798~8.777 (d, 1H), 8.738~8.717 (d, 1H), 8.619~8.604
(d, 1H), 7.875~7.855 (d, 1H), 7.800~8.653 (m, 7H), 7.587~7.514 (m, 5H), 7.382~7.350
(m, 1H), 7.289~7.270 (t, 1H), 7.215~7.195 (d, 1H).13C-NMR(CDCl3,400MHz):δ(ppm)
150.09,148.48,148.11,138.72,137.91,137.49,135.77,134.29,130.31,129.98,129.94,
129.35,129.12,128.35,128.33,127.35,127.14,126.85,126.33,125.74,125.02,124.14,
123.59,123.15,122.98,122.78,120.88。MS(APCI)(m/z):[M+H+]calcd for C32H22N3:
448.17,found,448.12。
Embodiment 2
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1It is for pyridineR2It is former for hydrogen
Son, R3For hydrogen atom, R4For hydrogen atom；Its chemical name is 2- (3- (3- pyridines) phenyl) -1- phenyl -1H- [9,10-d] phenanthro-
Imidazoles, abbreviation CPI-m3Py, structural formula is as follows：
Building-up process is identical with compound CPI-p3Py, obtain white solid 2- (3- (3- pyridines) phenyl) -1- phenyl -
1H- [9,10-d] phenanthro- imidazoles (CPI-m3Py) 1.50g.Yield：84%.1H-NMR(CDCl3,400MHz):δ(ppm)8.933
~8.913 (d, 1H), 8.799~8.778 (d, 1H), 8.738~8.717 (d, 1H), 8.628~8.611 (d, 2H), 7.777
~7.660 (m, 8H), 7.599~8.534 (m, 4H), 7.463~7.434 (t, 1H), 7.296~7.235 (m, 3H).13C-NMR
(CDCl3,400MHz):δ(ppm)150.19,148.61,148.18,138.82,137.64,137.44,134.37,131.29,
130.36,129.98,129.37,129.20,129.13,128.33,128.27,128.04,127.43,127.36,127.16,
126.35,125.74,125.05,124.16,123.57,123.16,122.97,122.76,120.91。MS(APCI)(m/z):
[M+H+]calcd for C32H22N3:448.17,found,448.09。
Embodiment 3
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1For hydrogen atom, R2It is for pyridineR3For hydrogen atom, R4For hydrogen atom；Its chemical name be 2- (4- (3- pyridines) phenyl) -1- phenyl -1H- [9,
10-d] phenanthro- imidazoles, abbreviation NPI-p3Py, structural formula is as follows：
Building-up process is identical with compound CPI-p3Py, obtain white solid 2- (4- (3- pyridines) phenyl) -1- phenyl -
1H- [9,10-d] phenanthro- imidazoles (NPI-p3Py) 1.46g.Yield：82%.1H-NMR(CDCl3,400MHz):δ(ppm)9.031
~9.025 (d, 1H), 8.939~8.920 (d, 1H), 8.813~8.792 (d, 1H), 8.746~8.704 (t, 2H), 8.045
~8.025 (d, 1H), 7.838~7.761 (m, 3H), 7.689~7.619 (m, 5H), 7.557~7.531 (m, 1H), 7.489
~7.458 (m, 1H), 7.360~7.284 (m, 5H).13C-NMR(CDCl3,400MHz):δ(ppm)151.03,149.28,
148.31,139.10,138.56,137.42,135.04,134.51,130.31,129.83,129.54,129.34,129.01,
128.58,128.34,128.31,128.02,127.38,127.11,126.37,126.37,125.76,125.02,124.22,
123.78。MS(APCI):calcd for C32H22N3:448.17,found,448.16。
Embodiment 4
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1For hydrogen atom, R2It is for pyridineR3For hydrogen atom, R4For hydrogen atom；Its chemical name is 1- (3- (3- pyridines) phenyl) -2- phenyl -1H- [9,10-
D] phenanthro- imidazoles, abbreviation NPI-m3Py, structural formula is as follows：
Building-up process is identical with compound CPI-p3Py, obtain white solid 1- (3- (3- pyridines) phenyl) -2- phenyl -
1H- [9,10-d] phenanthro- imidazoles (NPI-m3Py) 1.44g.Yield：81%.1H-NMR(CDCl3,400MHz):δ(ppm)8.945
~8.925 (d, 1H), 8.847~8.801 (t, 2H), 8.751~8.730 (d, 1H), 8.648~8.638 (d, 1H), 7.879
~7.693 (m, 6H), 7.641~7.535 (m, 4H), 7.399~7.284 (m, 6H).13C-NMR(CDCl3,400MHz):δ
(ppm)150.95,149.28,148.17,139.92,139.43,137.35,134.94,134.48,130.82,130.21,
129.56,129.38,129.10,128.59,128.34,127.86,127.58,127.40,127.04,126.39,125.79,
125.06,124.27,123.75,123.13,122.89,120.77。MS(APCI)(m/z):[M+H+]calcd for
C32H22N3:448.17,found,448.13。
Embodiment 5
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1It is for pyridineR2It is for pyridineR3For hydrogen atom, R4For hydrogen atom；Its chemical name is 1,2- bis- (4- (3- pyridines) phenyl) -1H- [9,10-d]
Phenanthro- imidazoles, abbreviation CNPI-p3Py, structural formula is as follows：
Building-up process is identical with compound CPI-p3Py, obtains white solid 1,2- bis- (4- (3- pyridines) phenyl) -1H-
[9,10-d] phenanthro- imidazoles (CNPI-p3Py) 1.69g.Yield：79%.1H-NMR(CDCl3,400MHz):δ (ppm) 9.053~
9.049 (d, 1H), 8.919~8.715 (m, 5H), 8.616~8.605 (d, 1H), 8.072~8.052 (d, 1H), 7.891~
7.871 (d, 3H), 7.789~7.676 (m, 6H), 7.564~7.544 (d, 3H), 7.501~7.469 (m, 1H), 7.488~
7.284(m,3H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.20,149.39,148.68,148.34,148.05,
139.33,138.58,138.05,137.65,135.73,134.61,134.49,134.34,132.11,132.05,130.20,
130.03,129.84,129.34,129.22,128.87,128.63,128.51,128.36,128.29,127.42,127.10,
126.50,126.43,125.85,125.14,124.25,123.80,123.17,122.91,122.82,120.81。MS
(APCI):calcd for C37H25N4:525.61,found,525.47。
Embodiment 6
A kind of phenanthro- imdazole derivatives, it has formula (I) structure, wherein R1It is for pyridineR2It is for pyridineR3For hydrogen atom, R4For hydrogen atom；Its chemical name is 1,2- bis- (3- (3- pyridines) phenyl) -1H- [9,10-d]
Phenanthro- imidazoles, abbreviation CNPI-m3Py, structural formula is as follows：
Building-up process is identical with compound CPI-p3Py, obtains white solid 1,2- bis- (3- (3- pyridines) phenyl) -1H-
[9,10-d] phenanthro- imidazoles (CNPI-m3Py) 1.73g.Yield：83%.1H-NMR(CDCl3,400MHz):δ (ppm) 8.920~
8.900 (d, 1H), 8.857~8.852 (d, 1H), 8.799~8.778 (d, 1H), 8.729~8.708 (d, 1H), 8.632~
8.625 (d, 2H), 8.593~8.584 (d, 1H), 7.930~7.910 (d, 2H), 7.859~7.839 (d, 1H), 7.807~
7.631 (m, 8H), 7.552~7.529 (m, 2H), 7.457~7.438 (t, 1H), 7.372~7.311 (m, 4H).13C-NMR
(CDCl3,400MHz):δ(ppm)150.23,149.46,148.71,148.25,148.14,140.31,139.63,137.74,
137.61,135.94,134.84,134.45,134.28,131.18,131.06,129.44,129.21,129.10,128.66,
128.52,128.36,128.16,128.11,127.72,127.55,127.42,127.13,126.45,125.85,125.16,
124.29,123.77,123.54,123.18,122.88,122.80,120.80。MS(APCI):calcd for C37H25N4:
525.61,found,525.58。
Embodiment 7：CPI-p3Py prepares device as electron transport material.
This example illustrates the performance verification for the electroluminescent device that CPI-p3Py is prepared as electron transport material.
The phenanthro- imdazole derivatives of the present embodiment as multilayer organic electroluminescence device structure as shown in Figure 2 (on being designated in Fig. 2
The 3 kinds of compounds stated, only choose one kind therein in device fabrication processes), ITO (tin indium oxide) glass is in succession in cleaning agent
With in deionized water with ultrasonic wave clean 30 minutes.Then 2 hours (105 DEG C) are dried in vacuo, then by ITO (tin indium oxide) glass
The oxygen plasma treatment carried out in plasma reactor 5 minutes is put into, is sent in vacuum chamber and prepares organic film and metal electrode,
Then the thick holes of 80nm are then deposited in the hole-injecting material molybdenum trioxide for preparing one layer of 10nm by the method for vacuum evaporation
Transmission material:TAPC, then continues through the material of vacuum evaporation last layer 12nm blue light emitting on this hole transmission layer
MADN:2wt%BUBD-1, is finally deposited one layer of 15nm electron transport material (CPI-p3Py) and LiF of the invention again
(1nm)/Al(100nm)。
Embodiment 8：NPI-p3Py prepares device as electron transport material.
This example illustrates the performance verification for the electroluminescent device that NPI-p3Py is prepared as electron transport material.
The phenanthro- imdazole derivatives of the present embodiment as multilayer organic electroluminescence device structure as shown in Figure 2 (on being designated in Fig. 2
The 3 kinds of compounds stated, only choose one kind therein in device fabrication processes), ITO (tin indium oxide) glass is in succession in cleaning agent
With in deionized water with ultrasonic wave clean 30 minutes.Then 2 hours (105 DEG C) are dried in vacuo, then by ITO (tin indium oxide) glass
The oxygen plasma treatment carried out in plasma reactor 5 minutes is put into, is sent in vacuum chamber and prepares organic film and metal electrode,
Then the thick holes of 80nm are then deposited in the hole-injecting material molybdenum trioxide for preparing one layer of 10nm by the method for vacuum evaporation
Transmission material:TAPC, then continues through the material of vacuum evaporation last layer 12nm blue light emitting on this hole transmission layer
MADN:2wt%BUBD-1, is finally deposited one layer of 15nm electron transport material (NPI-p3Py) and LiF of the invention again
(1nm)/Al(100nm)。
Embodiment 9：CNPI-p3Py prepares device as electron transport material.
The performance that this example illustrates the electroluminescent device that CNPI-p3Py is prepared as electron transport material is tested
Card.The phenanthro- imdazole derivatives of the present embodiment (are indicated in Fig. 2 as shown in Figure 2 as the structure of multilayer organic electroluminescence device
3 kinds of above-mentioned compounds, only choose one kind therein in device fabrication processes), ITO (tin indium oxide) glass is in succession clear
Cleaned 30 minutes with ultrasonic wave in lotion and deionized water.Then 2 hours (105 DEG C) are dried in vacuo, then by ITO (tin indium oxide)
Glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, is sent in vacuum chamber and prepares organic film and metal
80nm thickness is then deposited in electrode, the hole-injecting material molybdenum trioxide for then preparing one layer of 10nm by the method for vacuum evaporation
Hole mobile material:TAPC, then continues through vacuum evaporation last layer 12nm blue light emitting on this hole transmission layer
Material MADN:2wt%BUBD-1, is finally deposited one layer of 15nm electron transport material (CNPI-p3Py) and LiF of the invention again
(1nm)/Al(100nm)。
Embodiment 10：The performance parameter for the device that six kinds of compounds of embodiment 1 to 6 make is shown in Table 2.
Six kinds of compounds of the embodiment 1 to 6 of table 2 as electric transmission body material Electroluminescence Properties
Six kinds of compounds of embodiment 1 to 6 as electron transport material brightness-Current density-voltage performance diagram
See Fig. 3.
Six kinds of compounds of embodiment 1 to 6 are used as the device efficiency of electron transport material and the characteristic curve of current density
Figure is shown in Fig. 4.
Six kinds of compounds of embodiment 1 to 6 are shown in figure as the electroluminescence characters curve map of the device of electron transport material
5。
Six kinds of compound pyridines substitution phenanthro- imidazoles electron transport material electron mobility curve of embodiment 1 to 6.
The electron mobility of the phenanthro- imdazole derivatives is 10-7-10-3cm2/ Vs or so, illustrates by effectively adjusting
The peripheral drawing electron group of phenanthro- imdazole derivatives can obtain the electron transport material of high mobility, the electronics used with tradition
Transmission material BPhen is higher by two number magnitudes.
As it will be easily appreciated by one skilled in the art that the foregoing is merely illustrative of the preferred embodiments of the present invention, it is not used to
The limitation present invention, any modifications, equivalent substitutions and improvements made within the spirit and principles of the invention etc., it all should include
Within protection scope of the present invention.
Claims (3)
1. a kind of phenanthro- imdazole derivatives, it is characterised in that it has such as compound one, compound two, compound three, compound
4th, compound five, the structure shown in any one of compound six：
The electron mobility of the phenanthro- imdazole derivatives is 10-7-10-3cm2/Vs。
2. a kind of application of phenanthro- imdazole derivatives as claimed in claim 1, it is characterised in that transmit material as luminous electron
Material.
3. a kind of organic electroluminescence device, it is characterised in that including multilayer organic material, wherein transport layer or emitting layer material
Including phenanthro- imdazole derivatives as claimed in claim 1.
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