CN104817540A - Phenanimidazole derivative and application thereof - Google Patents
Phenanimidazole derivative and application thereof Download PDFInfo
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Abstract
The invention discloses a phenanimidazole derivative which is high in triplet energy, glass transition temperature and electron or hole transmission ability. When the phenanimidazole derivative is used as an electron transmission material, compared with an electron transmission material BCP, serving as as a conventional main material of an electron transmission group, commonly used in the prior art, the phenanimidazole derivative has the advantage that electron transmission ability is improved remarkably; in an organic electroluminescent device, compared with conventional electron transmission materials, and the phenanimidazole derivative has the advantage that glass transition temperature, current efficiency, power efficiency, external quantum efficiency and roll-off are improved remarkably, and is an ideal electron transmission material.
Description
Technical field
The invention belongs to field of photovoltaic materials, more specifically, relate to a kind of phenanthro-imdazole derivatives and application thereof.
Background technology
Organic electroluminescent phenomenon is found in 1963 the earliest, utilizes organic anthracene crystal as luminescent material at that time, and because this device drive voltage is up to 400V, and device efficiency and life-span are far away from inorganic electroluminescence device, do not cause the attention of people at that time.1987, Deng Qingyun (Tang, C.W.et al.Appl.Phys.Lett.1987,52,913) research group proposed the OLED structure of organic multilayer non-crystal thin film first; People (Burroughes, J.H.et al.Nature.1990,347, the 539) reported first such as nineteen ninety Burroughes polymer LED, organic electroluminescent research enters brand-new stage since then.Nearly ten years, Organic Light Emitting Diode is applied to (Journal of the AmericanChemical Society, 2002,124,11576 in high-quality flat-panel screens because having the advantages such as response is fast, brightness is high, operating voltage is low; Journal of Display Technology, 2005,1,90; Molecular Electronics and Bioelectronics.2007,18,25).
Obtain the OLED of excellent performance, first will select the transport material that mobility is enough outstanding, ensure that electron hole can balance in luminescent layer, but electron transport material is very in short supply at present, Alq
3be widely used with its good stability, but due to its lower mobility, be difficult to prepare efficient OLED.
Existing electron transport material electronic mobility still haves much room for improvement, and development high-mobility electron transport material is the efficient OLED of preparation is the focus that we study all the time.
Summary of the invention
For above defect or the Improvement requirement of prior art, the invention provides a kind of phenanthro-imdazole derivatives and application thereof, its object is to the electron transport material providing a kind of electronic mobility high, solve the technical problem that its electronic mobility of OLED electron transport material is still to be improved thus.
For achieving the above object, according to one aspect of the present invention, provide a kind of phenanthro-imdazole derivatives, it has the structure of formula (I):
Wherein, R
1, R
2, R
3and R
4for hydrogen atom or drawing electron group, R
1, R
2, R
3and R
4identical or different.
Preferably, described phenanthro-imdazole derivatives, drawing electron group described in it is selected from following group:
Preferably, described phenanthro-imdazole derivatives, R described in it
3and R
4for hydrogen atom.
According to another aspect of the present invention, provide a kind of application of described phenanthro-imdazole derivatives, it is used as emitting electron transport material.
According to another aspect of the present invention, provide a kind of organic electroluminescence device, comprise multilayer organic materials, wherein transport layer or emitting layer material comprise described phenanthro-imdazole derivatives.
In general, the above technical scheme conceived by the present invention compared with prior art, can obtain following beneficial effect:
The compound with structure shown in general formula (I) provided by the invention is that a class has higher triplet energies, high glass transition temperature, and good electrons transmittability.When it uses as electron transport material, compared with being the convention body material of electron transporting groups with electron transport material BCP conventional in prior art, the transmittability of electronics is significantly improved, in organic electroluminescence device, this compound compared with traditional electron transport material in second-order transition temperature, current efficiency, power efficiency, external quantum efficiency and aspect of roll-offing all increase significantly, and are desirable electron transport materials.
Phenanthro-imidazoles electron transporting groups is used in fluorescent electronic transport material by the present invention first, has synthesized a series of asymmetric electron transport material.Such as, take CNPI-p3Py as the fluorescence Blue-light emitting host material of electron transport material, preparation, its device maximum current efficiency, power efficiency and external quantum efficiency reach 11.12cd/A respectively, 7.23lm/w and 5.66%.The material of synthesis has very high second-order transition temperature, higher triplet energies, and has good hole and electron transport ability, in fluorescent blue optical device, demonstrate superior efficiency.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of phenanthro-imidazoles electron transport material;
Fig. 2 is embodiment 7 to 9 electron transport material fabricate devices structural representation;
Fig. 3 is the luminance-current density vs. voltage performance diagram of embodiment 10 electron transport material;
Fig. 4 is the device current efficiency of embodiment 10 electron transport material and the performance diagram of current density;
Fig. 5 is the electroluminescence characters graphic representation of the device of embodiment 10 electron transport material;
Fig. 6 is that pyridine replaces phenanthro-imidazoles electron transport material electronic migration rate curve.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.In addition, if below in described each embodiment of the present invention involved technical characteristic do not form conflict each other and just can mutually combine.
Phenanthro-imdazole derivatives provided by the invention, it has the structure of formula (I):
Wherein, R
1, R
2, R
3and R
4for hydrogen atom or drawing electron group, R
1, R
2, R
3and R
4identical or different.Described drawing electron group, preferably hales electron group, as pyridine, pyrimidine, triazine, 1,2,4-thiadiazoles, and benzoglyoxaline, oxadiazoles, oxazole, triazole, phenanthroline etc.Described drawing electron group is selected from following group:
Preferably, described its R of phenanthro-imdazole derivatives
3and R
4for hydrogen atom.More preferably, phenanthro-imdazole derivatives R is stated
1be selected from pyridine, pyrimidine, benzoglyoxaline, R
2be selected from pyridine, pyrimidine, benzoglyoxaline, further, there is following structure:
Phenanthro-imdazole derivatives provided by the invention can take phenanthrenequione as raw material, is obtained by ring-closure reaction.Synthetic route is shown in Fig. 1, the synthetic route of phenanthro-imidazoles electron transport material, reaction conditions: i) aniline, bromobenzene formaldehyde, Potassium ethanoate, acetic acid, 120 DEG C, 12 hours; Ii) toluene, ethanol, wet chemical (2M), Pd (PPh
3)
4, 24 hours.
Phenanthro-imdazole derivatives provided by the invention, electronic mobility can reach 10
-3cm
2v
-1s
-1left and right, improves the mobility of electron transport material greatly, as emitting electron transport material, realizes carrier balance, thus the stability of device and efficiency are all significantly promoted.
Invention also provides a kind of electroluminescent device, comprise multilayer organic materials, wherein transport layer or emitting layer material comprise phenanthro-imdazole derivatives provided by the invention.
Be below embodiment:
Embodiment 1
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for pyridine is
r
2for hydrogen atom, R
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 2-(4-(3-pyridine) phenyl)-1-phenyl-1H-[9,10-d] phenanthro-imidazoles, and be called for short CPI-p3Py, structural formula is as follows:
Its preparation method is as follows: under condition of nitrogen gas protection, by compound 2-(4-bromophenyl)-1-phenyl-1H-[9, 10-d] phenanthro-imidazoles (1) (1.76g, 4.0mmol), 3-pyridine borate (0.50g, 4.0mmol), toluene (100ml), dehydrated alcohol (50ml), 2M K
2cO
3(50ml) aqueous solution adds in dry 500ml two mouthfuls of round-bottomed flasks successively, ultrasonic 30 minutes, under the condition of nitrogen, reaction is heated to 80 DEG C, stirring and refluxing 24 hours, question response is cooled to room temperature, add methylene dichloride (60ml) and extract three times, collect organic phase washed with water (50ml) and wash three times, and by organic phase anhydrous magnesium sulfate drying 12 hours, filter, column chromatography (developping agent: ethyl acetate and sherwood oil) obtains white solid 2-(4-(3-pyridine) phenyl)-1-phenyl-1H-[9, 10-d] phenanthro-imidazoles (CPI-p3Py) 1.53g.Productive rate: 86%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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 forC
32H
22N
3:448.17,found,448.12。
Embodiment 2
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for pyridine is
r
2for hydrogen atom, R
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 2-(3-(3-pyridine) phenyl)-1-phenyl-1H-[9,10-d] phenanthro-imidazoles, and be called for short CPI-m3Py, structural formula is as follows:
Building-up process is identical with Compound C PI-p3Py, obtains white solid 2-(3-(3-pyridine) phenyl)-1-phenyl-1H-[9,10-d] phenanthro-imidazoles (CPI-m3Py) 1.50g.Productive rate: 84%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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 C
32H
22N
3:448.17,found,448.09。
Embodiment 3
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for hydrogen atom, R
2for pyridine is
r
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 2-(4-(3-pyridine) phenyl)-1-phenyl-1H-[9,10-d] phenanthro-imidazoles, and be called for short NPI-p3Py, structural formula is as follows:
Building-up process is identical with Compound C PI-p3Py, obtains white solid 2-(4-(3-pyridine) phenyl)-1-phenyl-1H-[9,10-d] phenanthro-imidazoles (NPI-p3Py) 1.46g.Productive rate: 82%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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 C
32H
22N
3:448.17,found,448.16。
Embodiment 4
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for hydrogen atom, R
2for pyridine is
r
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 1-(3-(3-pyridine) phenyl)-2-phenyl-1H-[9,10-d] phenanthro-imidazoles, and be called for short NPI-m3Py, structural formula is as follows:
Building-up process is identical with Compound C PI-p3Py, obtains white solid 1-(3-(3-pyridine) phenyl)-2-phenyl-1H-[9,10-d] phenanthro-imidazoles (NPI-m3Py) 1.44g.Productive rate: 81%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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
+]calcdfor C
32H
22N
3:448.17,found,448.13。
Embodiment 5
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for pyridine is
r
2for pyridine is
r
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 1,2-bis-(4-(3-pyridine) phenyl)-1H-[9,10-d] phenanthro-imidazoles, and be called for short CNPI-p3Py, structural formula is as follows:
Building-up process is identical with Compound C PI-p3Py, obtains white solid 1,2-bis-(4-(3-pyridine) phenyl)-1H-[9,10-d] phenanthro-imidazoles (CNPI-p3Py) 1.69g.Productive rate: 79%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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 C
37H
25N
4:525.61,found,525.47。
Embodiment 6
A kind of phenanthro-imdazole derivatives, it has the structure of formula (I), wherein R
1for pyridine is
r
2for pyridine is
r
3for hydrogen atom, R
4for hydrogen atom; Its chemical name is 1,2-bis-(3-(3-pyridine) phenyl)-1H-[9,10-d] phenanthro-imidazoles, and be called for short CNPI-m3Py, structural formula is as follows:
Building-up process is identical with Compound C PI-p3Py, obtains white solid 1,2-bis-(3-(3-pyridine) phenyl)-1H-[9,10-d] phenanthro-imidazoles (CNPI-m3Py) 1.73g.Productive rate: 83%.
1H-NMR(CDCl
3,400MHz):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(CDCl
3,400MHz):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 C
37H
25N
4:525.61,found,525.58。
Embodiment 7:CPI-p3Py is as electron transport material fabricate devices.
The performance verification of the electroluminescent device that this examples show CPI-p3Py is prepared as electron transport material.The phenanthro-imdazole derivatives of the present embodiment (designates 3 kinds of above-mentioned compounds as shown in Figure 2 as the structure of multilayer organic electroluminescence device in Fig. 2, in device fabrication processes, only choose one wherein), ITO (tin indium oxide) glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes.Then vacuum-drying 2 hours (105 DEG C), again ITO (tin indium oxide) glass is put into the oxygen plasma treatment that plasma reactor carries out 5 minutes, be sent in vacuum chamber and prepare organic membrane and metal electrode, then the hole-injecting material molybdic oxide hole mobile material that then evaporation 80nm is thick of one deck 10nm is prepared by the method for vacuum-evaporation: TAPC, then on this hole transmission layer, continue through the material MADN:2wt%BUBD-1 of the blue light emitting of vacuum evaporation last layer 12nm, the electron transport material of the present invention (CPI-p3Py) of last evaporation one deck 15nm again and LiF (1nm)/Al (100nm).
Embodiment 8:NPI-p3Py is as electron transport material fabricate devices.
The performance verification of the electroluminescent device that this examples show NPI-p3Py is prepared as electron transport material.The phenanthro-imdazole derivatives of the present embodiment (designates 3 kinds of above-mentioned compounds as shown in Figure 2 as the structure of multilayer organic electroluminescence device in Fig. 2, in device fabrication processes, only choose one wherein), ITO (tin indium oxide) glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes.Then vacuum-drying 2 hours (105 DEG C), again ITO (tin indium oxide) glass is put into the oxygen plasma treatment that plasma reactor carries out 5 minutes, be sent in vacuum chamber and prepare organic membrane and metal electrode, then the hole-injecting material molybdic oxide hole mobile material that then evaporation 80nm is thick of one deck 10nm is prepared by the method for vacuum-evaporation: TAPC, then on this hole transmission layer, continue through the material MADN:2wt%BUBD-1 of the blue light emitting of vacuum evaporation last layer 12nm, the electron transport material of the present invention (NPI-p3Py) of last evaporation one deck 15nm again and LiF (1nm)/Al (100nm).
Embodiment 9:CNPI-p3Py is as electron transport material fabricate devices.
The performance verification of the electroluminescent device that this examples show CNPI-p3Py is prepared as electron transport material.The phenanthro-imdazole derivatives of the present embodiment (designates 3 kinds of above-mentioned compounds as shown in Figure 2 as the structure of multilayer organic electroluminescence device in Fig. 2, in device fabrication processes, only choose one wherein), ITO (tin indium oxide) glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes.Then vacuum-drying 2 hours (105 DEG C), again ITO (tin indium oxide) glass is put into the oxygen plasma treatment that plasma reactor carries out 5 minutes, be sent in vacuum chamber and prepare organic membrane and metal electrode, then the hole-injecting material molybdic oxide hole mobile material that then evaporation 80nm is thick of one deck 10nm is prepared by the method for vacuum-evaporation: TAPC, then on this hole transmission layer, continue through the material MADN:2wt%BUBD-1 of the blue light emitting of vacuum evaporation last layer 12nm, the electron transport material of the present invention (CNPI-p3Py) of last evaporation one deck 15nm again and LiF (1nm)/Al (100nm).
Embodiment 10: the performance perameter of the device of six kinds of compounds making of embodiment 1 to 6 is in table 2.
Six kinds of compounds of table 2 embodiment 1 to 6 are as the Electroluminescence Properties of electric transmission body material
Six kinds of compounds of embodiment 1 to 6 are shown in Fig. 3 as the brightness-Current density-voltage performance diagram of electron transport material.
Six kinds of compounds of embodiment 1 to 6 are shown in Fig. 4 as the device efficiency of electron transport material and the performance diagram of current density.
Six kinds of compounds of embodiment 1 to 6 are shown in Fig. 5 as the electroluminescence characters graphic representation of the device of electron transport material.
Six kinds of compound pyridines of embodiment 1 to 6 replace phenanthro-imidazoles electron transport material electronic migration rate curve.
The electronic mobility of described phenanthro-imdazole derivatives is 10
-7-10
-3cm
2about/Vs, the electron transport material by effectively regulating the peripheral drawing electron group of phenanthro-imdazole derivatives can obtain high mobility is described, the electron transport material BPhen used with tradition exceeds two number magnitude.
Those skilled in the art will readily understand; the foregoing is only preferred embodiment of the present invention; not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (5)
1. a phenanthro-imdazole derivatives, is characterized in that, it has the structure of formula (I):
Wherein, R
1, R
2, R
3and R
4for hydrogen atom or drawing electron group, R
1, R
2, R
3and R
4identical or different.
2. phenanthro-imdazole derivatives as claimed in claim 1, it is characterized in that, described drawing electron group is selected from following group:
3. phenanthro-imdazole derivatives as claimed in claim 1, is characterized in that, described R
3and R
4for hydrogen atom.
4. the application of phenanthro-imdazole derivatives as described in claims 1 to 3 any one, is characterized in that, as emitting electron transport material.
5. an organic electroluminescence device, is characterized in that, comprises multilayer organic materials, and wherein transport layer or emitting layer material comprise the phenanthro-imdazole derivatives as described in claims 1 to 3 any one.
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| WO2022105626A1 (en) * | 2020-11-18 | 2022-05-27 | Tcl科技集团股份有限公司 | Quantum dot light emitting diode, display apparatus, and luminescent light source |
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