CN109053680A - It is the small organic molecule photoelectric functional material and its preparation method and application of receptor unit based on 3- benzoyl pyridine - Google Patents
It is the small organic molecule photoelectric functional material and its preparation method and application of receptor unit based on 3- benzoyl pyridine Download PDFInfo
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Abstract
The invention discloses the small organic molecule photoelectric functional materials for based on 3- benzoyl pyridine being receptor unit; mainly depend on the hydrogen bond action of nitrogen in benzoyl pyridine; it can effectively avoid the deficiency of the reduction of rate of irradiation caused by big torsion angle; to molecularly oriented of improving the standard, the simplification of device architecture and the raising of device performance and service life are realized.Meanwhile type and size by regulating and controlling donor connection unit, it can effectively adjust the inherent characteristics such as molecular weight, conjugate length, the electric charge transfer of material.The invention also discloses the preparation method and application of above-mentioned material.The present invention is based on 3- benzoyl pyridine be receptor unit organic micromolecular photoelectric material; have many advantages, such as high rate of irradiation constant, high-quantum efficiency, high carrier transport performance, the luminescent layer as organic electroluminescence device presents adjustable coloration, efficient stable and long-life.
Description
Technical field
The present invention relates to the field of material technology of organic electro-optic device, in particular to are receptor based on 3- benzoyl pyridine
Small organic molecule photoelectric functional material of unit and its preparation method and application.
Background technique
Organic electroluminescent (OLED) device has huge application prospect in FPD and solid light source field.In order to
Improve efficiency and the service life of organic electro-optic device, small organic molecule has preparation simple, tie compared to polymer luminescent material
Structure is stablized, and purifying is facilitated, thus can obtain higher device efficiency, so that close to commercial applications.Currently, based on small
Molecule, which is developed, can get redgreenblue luminescent material and simultaneously prepares layer flexible device, thus the concern that causes people strong and
Achieve huge progress.
In recent years, hot activation delay mechanism fluorescent material is widely used in OLED device, and this kind of material can effectively be put
The intramolecular spin coupling effect of de- conventional fluorescent material, while the singlet exciton and 75% for being 25% using generating probability
Triplet excitons, therefore greatly improve luminous efficiency.Currently, small as the organic light emission of receptor core using 3- benzoyl pyridine
Molecular material is rarely reported.Therefore, it is luminescent material that the present invention, which devises a series of derivatives of benzoyl pyridine,.Its receptor
The nitrogen active site of core effectively can form hydrogen bond by coupling with corresponding aromatic amine, improve molecular level orientation, help to mention
The efficiency and stability of high material and device.
Though disclosing benzophenone radical derivative [H.Zhao, Z.Wang, X.Cai, S.-J.Su, Highly before this
Efficient Thermally Activated Delayed Fluorescence Materials with Reduced
Efficiency Roll-Off and Low On-Set Voltage[J].Materials Chemistry Frontiers
2017,1,2039-2046；S.Oh,K.H.Lee,J.H.Seo, S.S.Yoon,Highly Efficient Blue Light-
Emitting Materials Based on Arylamine Substituted DPVBiDerivatives[J].Journal
of Nanoscience and Nanotechnology,2011,11,7250-7253；A. Kapturkiewicz,
J.Nowacki,Properties of the Intramolecular Excited Charge-Transfer States of
Carbazol-9-yl Derivatives of Aromatic Ketones[J].Journal of Physical
Chemistry A, 1999,103,8145-8155] and 4 '-benzoyl pyridine derivatives [P.Rajamalli,
N.Senthilkumar,P.-Y.Huang,C.-H.Cheng, A Method for Reducing the Singlet-
Triplet Energy Gaps of TADF Materials for Improving the Blue OLED Efficiency
[J].ACS Applied Materials&Interfaces,2016,8,27026-27034.].However material reported above
It is conventional benzophenone or nitrogen position distal end coupled receptors aromatic amine, weak to acceptor interaction, no intramolecular hydrogen bond divides
Son horizontal alignment is low, seriously affects and passes through rate and luminescent material stability between anti-system.For this purpose, the 3- benzene that the present invention designs
Formylpyridine derivative can overcome many disadvantages of appeal well, and nitrogen position proximal end connects to receptor and raw with hydrogen bond
At showing superior luminous efficiency and more stable device lifetime.Meanwhile 3- benzoyl pyridine coupling of the invention
Multidigit point, mostly for grade extensible donor series derivates, can meticulously explore to the push-and-pull characteristic electron between receptor, it is real
The improved efficiency of existing material and photochromic adjustable.
Summary of the invention
In order to overcome the disadvantages mentioned above and deficiency of the prior art, the purpose of the present invention is to provide one kind to be based on 3- benzoyl
Yl pyridines are the small organic molecule photoelectric functional material of receptor unit, have high-quantum efficiency, high carrier transport performance special
Point.
Another object of the present invention is to provide be above set forth in the small organic molecule light that 3- benzoyl pyridine is receptor unit
The preparation method of sulfate ferroelectric functional material.
A further object of the present invention is to provide be above set forth in the small organic molecule light that 3- benzoyl pyridine is receptor unit
The application of sulfate ferroelectric functional material.
The purpose of the present invention is achieved through the following technical solutions:
It is the small organic molecule photoelectric functional material of receptor unit based on 3- benzoyl pyridine, has the following structure logical
Formula:
Wherein:
R is selected from aromatic amine unit shown in (1)-(35):
Of the invention is the small organic molecule photoelectric functional material of receptor unit based on 3- benzoyl pyridine, is mainly depended on
The hydrogen bond action of nitrogen in benzoyl pyridine can effectively avoid the reduction of rate of irradiation caused by big torsion angle, to improve water
Flat molecularly oriented realizes the simplification of device architecture and the raising of device performance and service life.Meanwhile it is single by regulation donor connection
The type and size of member, can effectively adjust the material properties such as molecular weight, conjugate length, the electric charge transfer of material, of the invention
The bipolarity photoelectric material linked to-receptor efficiently avoids the unbalanced problem of unipolarity organic photoelectrical material carrier,
Hydrogen bond action can be cooperateed with to improve stability of material and dissolubility simultaneously.The preparation method is that with conventional bromobenzene and to bromine
Aldehyde radical pyridine then obtains target compound, material of the invention by a series of simple reactions as initial reaction raw materials
Expect that structure is single, molecular weight is clear；With very high thermal degradation temperature and sublimation temperature appropriate, it is easy sublimation purification.It is such
The advantages that material of invention presents adjustable coloration, efficient stable and long-life as the luminescent layer of organic electroluminescence device.
Compared with prior art, the present invention has the following advantages and beneficial effects:
(1) simple, the molecule of the invention using 3- benzoyl pyridine as the organic small molecule material structure of receptor nuclear unit
Amount determines, is easy to purify, electrochemically stable good, and its easily studied structure-activity relationship.
(2) of the invention that there is biggish molecule by the organic small molecule material of receptor nuclear unit of 3- benzoyl pyridine
Horizontal alignment, high fluorescent quantum yield can realize lower efficiency rolling while the property of hot activation delayed fluorescence is presented
Drop.
(3) of the invention to be coupled donor aromatic amine by receptor nuclear unit of 3- benzoyl pyridine, pass through nitrogen action site
Hydrogen bond action, can further develop the stabilized illumination mechanism of material, optimize material property, improve device lifetime.
(4) present invention is more importantly advantage also resides in, now to be confirmed by the same compound as donor with 3- benzene first
Acyl pyridine is that the organic small molecule material of receptor nuclear unit compared to the benzophenone of nitrogen-free action site is receptor core small molecule
Material (shows lower bright voltage, higher current density, superior external quantum efficiency and more stable device
Service life.
(5) of the invention using 3- benzoyl pyridine as receptor nuclear unit, it can be by changing the donor monomer being coupled
Type and size, number of loci and for number of stages (such as carbazole) effectively regulates and controls the photochromic and efficiency realization of material, and
Meet the needs of organic electro-optic device.
Detailed description of the invention
Fig. 1 is Absorption and emission spectra of the compound P16 in toluene solution；
Fig. 2 is the electrochemical stability of compound P16, and repeated oxidation reduction scans 100 times；
Fig. 3 is the Current density-voltage-being applied in organic light emitting diode device for compound P16 in embodiment 16
Brightness relationship curve figure；
Fig. 4 is the current efficiency-brightness-being applied in organic light emitting diode device for compound P16 in embodiment 16
External quantum efficiency graph of relation；
Fig. 5 is the electroluminescent spectrum of compound P16 in embodiment 16.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, embodiments of the present invention are not limited thereto.
Embodiment 1
The reaction equation of compound P1 is as follows:
Specific reaction step is as follows:
By (6- bromopyridine -3- base) (phenyl) ketone (1.5mmol, 390mg), carbazole (1.6mmol, 270mg), iodate
Cuprous (0.075mmol, 18mg), 1,10- phenanthroline (0.075mmol, 11mg) and natrium carbonicum calcinatum (3mmol, 415mg) according to
In secondary addition reaction flask.After substituting nitrogen 3 times, paraxylene 10mL is added by syringe.The lower 150 DEG C of reflux of condition of nitrogen gas
Reaction 24 hours.After reaction, restore room temperature to system, with methylene chloride and saturated salt solution extracting and washing.It recycles organic
Mutually and dry with anhydrous magnesium sulfate, vacuum distillation removes solvent.Then crude product is by column chromatographic isolation and purification, eluant, eluent
Petroleum ether/methylene chloride 3:1 finally obtains compound P1 product, yield 78%.Product formula: C24H16N2O；Molecular weight
m/z:348.13；Elemental analysis result are as follows: C, 72.74；H,4.63；N,8.04；O,4.59.
Embodiment 2
The reaction equation of compound P2 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the diphenylamines of equivalent, other raw materials and step are same
In embodiment 1, compound P2 product, yield 75% are finally obtained.Product formula: C24H18N2O；Molecular weight m/z:
350.16；Elemental analysis result are as follows: C, 82.26；H,5.18；N,7.99；O,4.57.
Embodiment 3
The reaction equation of compound P3 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the phenoxazine of equivalent, other raw materials and step are same
In embodiment 1, compound P3 product, yield 73% are finally obtained.Product formula: C24H16N2O2；Molecular weight m/z:
365.16；Elemental analysis result are as follows: C, 79.11；H,4.43；N,7.69；O,8.78.
Embodiment 4
The reaction equation of chemicals P4 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the phenthazine of equivalent, other raw materials and step are same
In embodiment 1, compound P3 product, yield 67% are finally obtained.Product formula: C24H16N2OS；Molecular weight m/z:
381.10；Elemental analysis result are as follows: C, 75.77；H,4.24；N,7.36；O,4.21；S,8.43.
Embodiment 5
The reaction equation of compound P5 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H- phenthazine 5 of equivalent, 5- dioxide,
His raw material and step are same as embodiment 1, finally obtain compound P5 product, yield 76%.Product formula:
C24H16N2O3S；Molecular weight m/z:412.09；Elemental analysis result are as follows: C, 69.89；H,3.91；N,6.79；O,11.64；S,
7.77。
Embodiment 6
The reaction equation of compound P6 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 9,9- dimethyl -9,10- acridan of equivalent,
Other raw materials and step are same as embodiment 1, finally obtain compound P6 product, yield 86%.Product formula:
C27H22N2O；Molecular weight m/z:390.17；Elemental analysis result are as follows: C, 83.05；H,5.68；N,7.17；O,4.10.
Embodiment 7
The reaction equation of compound P7 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 10,10-dimethyl-5,10- of equivalent
Dihydrodibenzo [b, e] [Isosorbide-5-Nitrae] azasiline, other raw materials and step are same as embodiment 1, finally obtain compound
P7 product, yield 83%.Product formula: C26H22N2OSi；Molecular weight m/z:406.15；Elemental analysis result are as follows: C,
76.81；H,5.45；N,6.89；O,3.94；Si,6.91.
Embodiment 8
The reaction equation of compound P8 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the acridine -9-10H- ketone of equivalent, other raw materials and
Step is same as embodiment 1, finally obtains compound P8 product, yield 76%.Product formula: C25H16N2O2；Molecule
Measure m/z:376.12；Elemental analysis result are as follows: C, 79.77；H,4.28；N,7.44；O,8.50.
Embodiment 9
The reaction equation of compound P9 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 3, the 6- di-t-butyl carbazole of equivalent, other raw materials
It is same as embodiment 1 with step, finally obtains compound P9 product, yield 73%.Product formula: C32H32N2O；Point
Son amount m/z:461.25；Elemental analysis result are as follows: C, 83.44；H,7.00；N,6.08；O,3.47.
Embodiment 10
The reaction equation of compound P10 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into bis- (4- tert-butyl-phenyl) amine of equivalent, other are former
Material and step are same as embodiment 1, finally obtain compound P10 product, yield 63%.Product formula: C34H34N2O；
Molecular weight m/z:463.27；Elemental analysis result are as follows: C, 83.08；H,7.41；N,6.06；O,3.46.
Embodiment 11
The reaction equation of compound P11 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 3, the 6- dimethoxy -9H- carbazole of equivalent, other
Raw material and step are same as embodiment 1, finally obtain compound P11 product, yield 73%.Product formula:
C26H20N2O3；Molecular weight m/z:409.15；Elemental analysis result are as follows: C, 76.46；H,4.94；N,6.86；O,11.75.
Embodiment 12
The reaction equation of compound P12 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 5- phenyl -5,10- dihydro of equivalent, other raw materials
It is same as embodiment 1 with step, finally obtains compound P12 product, yield 71%.Product formula: C30H21N3O；Point
Son amount m/z:439.17；Elemental analysis result are as follows: C, 81.98；H,4.82；N,9.56；O,3.64.
Embodiment 13
The reaction equation of compound P13 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H- spiral shell [acridine -9,9'- fluorenes] of equivalent, other
Raw material and step are same as embodiment 1, finally obtain compound P13 product, yield 77%.Product formula:
C37H24N2O；Molecular weight m/z:513.19；Elemental analysis result are as follows: C, 86.69；H,4.72；N,5.46；O,3.12.
Embodiment 14
The reaction equation of compound P14 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 9,9- diphenyl -9,10- acridan of equivalent,
Other raw materials and step are same as embodiment 1, finally obtain compound P14 product, yield 68%.Product formula:
C37H26N2O；Molecular weight m/z:514.21；Elemental analysis result are as follows: C, 86.35；H,5.09；N,5.44；O,3.11.
Embodiment 15
The reaction equation of compound P15 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H- spiral shell [acridine -9,9'- xanthene] of equivalent,
His raw material and step are same as embodiment 1, finally obtain compound P15 product, yield 73%.Product formula:
C37H24N2O2；Molecular weight m/z:528.17；Elemental analysis result are as follows: C, 84.07；H,4.58；N,5.30；O,6.05.
Embodiment 16
The reaction equation of compound P16 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H- spiral shell [acridine -9,9'- thioxanthene] of equivalent,
His raw material and step are same as embodiment 1, finally obtain compound P16 product, yield 76%.Product formula:
C37H24N2OS；Molecular weight m/z:544.16；Elemental analysis result are as follows: C, 81.59；H,4.44；N,5.14；O,2.94；S,
5.89。
Absorption and emission spectra of the compound P16 in toluene solution is as shown in Figure 1, as seen from the figure, compound P16 exists
Stronger vertical transition absorption peak is just being derived to the forceful electric power lotus transferance in acceptor molecule at 375nm, and is in 515nm
Existing single emission peak.
Test results are shown in figure 2 for the electrochemical stability of compound P16, and available compound P16 has appropriate
HOMO energy level, and after scan round 120 times, current -voltage curve discloses compound P16 and has very without significant change
Strong electrochemical stability.
Compound P16 is applied to Current density-voltage-brightness relationship curve figure in organic light emitting diode device as schemed
Shown in 3, electroluminescent device (example 33), which has good hole injection and transmittability, maximum brightness, can realize 12139 banks
De La/square metre.
Compound P16 is applied to current efficiency-brightness-external quantum efficiency relation curve in organic light emitting diode device
For figure as shown in Fig. 4, the maximum current efficiency of electroluminescent device (example 33) is 67.5 candelas/peace, maximum external quantum efficiency
It is 24.3%.
The electroluminescent spectrum of compound P16 in electroluminescent spectrum as shown in figure 5, be not observed secondary emission
Peak illustrates that luminescent device (example 33) realizes the abundant transfer of Subjective and Objective energy.
Embodiment 17
The reaction equation of compound P17 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H- spiral shell [acridine -9,9'- thioxanthene] of equivalent
10', 10'- dioxide, other raw materials and step are same as embodiment 1, finally obtain compound P17 product, and yield is
77%.Product formula: C37H24N2O3S；Molecular weight m/z:576.16；Elemental analysis result are as follows: C, 77.06；H,4.20；
N,4.86；O,8.32； S,5.56.
Embodiment 18
The reaction equation of compound P18 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10' of equivalent, 10'- dimethyl 10H, 10'H- spiral shell
[acridine -9,9'- anthracene], other raw materials and step are same as embodiment 1, finally obtain compound P18 product, yield 64%.
Product formula: C40H30N2O；Molecular weight m/z:554.25；Elemental analysis result are as follows: C, 86.61；H,5.45；N,5.05；
O,2.88。
Embodiment 19
The reaction equation of compound P19 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 5' of equivalent, 5'-dimethyl-5'H, 10H-
Spiro [acridine-9,10'-dibenzo [b, e] siline], other raw materials and step are same as embodiment 1, final to obtain
To compound P19 product, yield 79%.Product formula: C39H30N2OSi；Molecular weight m/z:570.22；Elemental analysis
As a result are as follows: C, 82.07；H,5.30；N,4.91；O,2.80；Si,4.92.
Embodiment 20
The reaction equation of compound P20 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 10H of equivalent, 10'H- spiral shell [acridine -9,9'-
Anthracene] -10' ketone, other raw materials and step are same as embodiment 1, finally obtain compound P20 product, yield 85%.Product
Molecular formula: C38H24N2O2；Molecular weight m/z:540.18；Elemental analysis result are as follows: C, 84.42；H,4.47；N,5.18；O,
5.92。
Embodiment 21
The reaction equation of compound P21 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 9H-3, the 9'-bicarbazole of equivalent, other
Raw material and step are same as embodiment 1, finally obtain compound P21 product, yield 73%.Product formula:
C36H23N3O；Molecular weight m/z:513.18；Elemental analysis result are as follows: C, 84.19；H,4.51；N,8.18；O,3.12.
Embodiment 22
The reaction equation of compound P22 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N of equivalent, N- diphenyl -9H- carbazole -3- amine,
Other raw materials and step are same as embodiment 1, finally obtain compound P22 product, yield 75%.Product formula:
C36H25N3O；Molecular weight m/z:515.27；Elemental analysis result are as follows: C, 83.86；H,4.89；N,8.15；O,3.10.
Embodiment 23
The reaction equation of compound P23 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 3', the 6'-di-tert-butyl-9H-3 of equivalent,
9'-bicarbazole, other raw materials and step are same as embodiment 1, finally obtain compound P23 product, yield 63%.
Product formula: C44H39N3O；Molecular weight m/z:625.31；Elemental analysis result are as follows: C, 84.45；H,6.28；N,6.71；
O,2.56。
Embodiment 24
The reaction equation of compound P24 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N of equivalent, bis- (4- tert-butyl) phenyl -9H- of N-
Carbazole -3- amine, other raw materials and step are same as embodiment 1, finally obtain compound P24 product, yield 63%.Product
Molecular formula: C44H41N3O；Molecular weight m/z:627.83；Elemental analysis result are as follows: C, 84.18；H,6.58；N,6.69；O,
2.55。
Embodiment 25
The reaction equation of compound P25 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 3' of equivalent, 6'-dimethoxy-9H-3,9'-
Bicarbazole, other raw materials and step are same as embodiment 1, finally obtain compound P25 product, yield 67%.It produces
Object molecular formula: C38H27N3O3；Molecular weight m/z:573.23；Elemental analysis result are as follows: C, 79.56；H,4.74；N,7.33；O,
8.37。
Embodiment 26
The reaction equation of compound P26 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the 9H-3,9':3', 9 "-of equivalent
Tercarbazole, other raw materials and step are same as embodiment 1, finally obtain compound P26 product, yield 62%.It produces
Object molecular formula: C48H30N4O；Molecular weight m/z:678.25；Elemental analysis result are as follows: C, 84.93；H,4.45；N,8.25；O,
2.36。
Embodiment 27
The reaction equation of compound P27 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N of equivalent, N-diphenyl-9H- [3,9'-
Bicarbazol] -3'-amine, other raw materials and step are same as embodiment 1, finally obtain compound P27 product, yield
It is 67%.Product formula: C48H32N4O；Molecular weight m/z:680.26；Elemental analysis result are as follows: C, 84.68；H,4.74；
N,8.23；O,2.35.
Embodiment 28
The reaction equation of compound P28 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that changing carbazole the 3 " of equivalent into, 6 "-dimethoxy-9-
Methyl-4 " a, the 9 "-tercarbazole of a-dihydro-9H-3,9':3', 9 ", other raw materials and step are same as embodiment
1, finally obtain compound P28 product, yield 63%.Product formula: C56H46N4O；Molecular weight m/z:790.37；Member
Element analysis result are as follows: C, 85.03；H,5.86；N,7.08；O,2.02.
Embodiment 29
The reaction equation of compound P29 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N of equivalent, N-bis (4- (tert-butyl)
Phenyl) -9H- [3,9'-bicarbazol] -3'-amine, other raw materials and step are same as embodiment 1, finally obtaining
Close object P29 product, yield 63%.Product formula: C56H48N4O；Molecular weight m/z:792.38；Elemental analysis result are as follows:
C,84.82；H,6.10；N,7.07；O,2.02.
Embodiment 30
The reaction equation of compound P30 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that changing carbazole the 3 " of equivalent into, 6 "-dimethoxy-9-
Methyl-4 " a, the 9 "-tercarbazole of a-dihydro-9H-3,9':3', 9 ", other raw materials and step are same as embodiment
1, finally obtain compound P30 product, yield 63%.Product formula: C50H36N4O3；Molecular weight m/z:740.28；Member
Element analysis result are as follows: C, 81.06；H,4.90；N,7.56；O,6.48.
Embodiment 31
The reaction equation of compound P31 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into-three carbazole of 9'H-9,3':6', 9 " of equivalent,
His raw material and step are same as embodiment 1, finally obtain compound P31 product, yield 71%.Product formula:
C48H30N4O；Molecular weight m/z:679.25；Elemental analysis result are as follows: C, 84.93；H,4.45；N,8.25；O,2.36.
Embodiment 32
The reaction equation of compound P32 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N3 of equivalent, N3, N6, N6- tetraphenyl -9H- click
Azoles -3,6- diamines, other raw materials and step are same as embodiment 1, finally obtain compound P32 product, yield 62%.It produces
Object molecular formula: C48H34N4O；Molecular weight m/z:682.83；Elemental analysis result are as follows: C, 84.43；H,5.02；N,8.21；O,
2.34。
Embodiment 33
The reaction equation of compound P33 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into 9'H-9,3':6', 9 "-the tri-tert click of equivalent
Azoles, other raw materials and step are same as embodiment 1, finally obtain compound P33 product, yield 77%.Product formula:
C64H62N4O；Molecular weight m/z:902.51；Elemental analysis result are as follows: C, 85.11；H,6.92；N,6.20；O,1.77.
Embodiment 34
The reaction equation of compound P34 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that carbazole to be changed into the N3 of equivalent, N3, N6, (the 4- (tert-butyl) of N6- tetra-
Phenyl) -9H- carbazole -3,6- diamines, other raw materials and step are same as embodiment 1, finally obtain compound P34 product, yield
It is 68%.Product formula: C64H66N4O；Molecular weight m/z:906.53；Elemental analysis result are as follows: C, 84.73；H,7.33；
N,6.18；O,1.76.
Embodiment 35
The reaction equation of compound P35 is as follows:
Specific reaction step is as follows:
Compared with Example 1, the difference is that changing carbazole into the 3 of equivalent, 3 ", 6,6 "-tetramethoxy-
- the tercarbazole of 9'H-9,3':6', 9 ", other raw materials and step are same as embodiment 1, finally obtain compound P35 production
Object, yield 56%.Product formula: C52H38N4O5；Molecular weight m/z:798.28；Elemental analysis result are as follows: C, 78.18；
H,4.79；N,7.01；O,10.01.
It is commercial goods that the compound that embodiment described above is used in the present invention, which is not specified,.Wherein above-mentioned aromatic amination
Object (1)~(12) are closed to purchase in public affairs such as Beijing J&K, Beijing Innochem, Shanghai TCI, Shanghai Chemhere, Hangzhou MolCore
Department.The preparation method of intermediate involved by aromatic amine compound 13~35 will further describe in following case study on implementation, but
The embodiment of intermediate of the present invention is without being limited thereto.
The preparation of midbody compound 13:
The present embodiment prepares intermediate aromatic amine compound 13, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Under the conditions of -78 DEG C of low temperature, 2- bromine diphenylamines 10mmol is dissolved in 30mL tetrahydrofuran, is then slowly added
Enter 4mL n-BuLi (2.5M) to stir 1 hour, it is rear that 9-Fluorenone 10mmol is added, continue stirring 30 minutes.Restore room temperature to remove
After solvent, it is scattered in acetic acid and continues stirring 5 hours for 70 DEG C.After reaction, restore room temperature to system, respectively with acetic acid and
Ethyl alcohol extracting and washing, then recrystallization purifying, finally obtains intermediate aromatic amine compound 13.
The preparation of midbody compound 14:
The present embodiment prepares intermediate aromatic amine compound 14, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone to be changed into the benzophenone of equivalent, other are former
Material and step are same as midbody compound 13, finally obtain intermediate aromatic amine compound 14.
The preparation of midbody compound 15:
The present embodiment prepares intermediate aromatic amine compound 15, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone is changed into the xanthone of equivalent, other raw materials
It is same as midbody compound 13 with step, finally obtains intermediate aromatic amine compound 15.
The preparation of midbody compound 16:
The present embodiment prepares intermediate aromatic amine compound 16, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone is changed into the thioxanthones of equivalent, other raw materials
It is same as midbody compound 13 with step, finally obtains intermediate aromatic amine compound 16.
The preparation of midbody compound 17:
The present embodiment prepares intermediate aromatic amine compound 17, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone to be changed into the thioxanthones 10 of equivalent, 10- dioxy
Compound, other raw materials and step are same as midbody compound 13, finally obtain intermediate aromatic amine compound 17.
The preparation of midbody compound 18:
The present embodiment prepares intermediate aromatic amine compound 18, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone to be changed into 10, the 10- dimethylanthracene of equivalent
Ketone, other raw materials and step are same as midbody compound 13, finally obtain intermediate aromatic amine compound 18.
The preparation of midbody compound 19:
The present embodiment prepares intermediate aromatic amine compound 19, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that changing 9-Fluorenone the 9,9-Dimethyl-9- of equivalent into
Silaanthracen-10 (9H)-one, other raw materials and step are same as midbody compound 13, finally obtain intermediate virtue
Fragrant amine compounds 19.
The preparation of midbody compound 20:
The present embodiment prepares intermediate aromatic amine compound 20, and compound P formula and synthetic route are as follows:
Specific reaction step is as follows:
Compared with midbody compound 13, the difference is that 9-Fluorenone to be changed into 9, the 10- anthraquinone of equivalent, other are former
Material and step are same as midbody compound 13, finally obtain intermediate aromatic amine compound 20.
In the present invention preparation method of compound P21~P35 intermediate therefor aromatic amine compound without limitation, it is typical but
Non-limiting synthetic route and the preparation method is as follows:
Wherein, X is F or Br or I；R can be with are as follows: 9H- carbazole；Diphenylamines；The bis- 4- tert-butyl carbazoles of 9H-；Double 4- tert-butyls
Diphenylamines；The bis- 4- methoxyl carbazoles of 9H-；3,9'- joins carbazole；Bis- (the phenyl) -9H- carbazole -3- amine of N, N-；3', 6'- di-t-butyl
- 9H-3,9'- carbazole；Bis- (4- tert-butyl) phenyl -9H- carbazole -3- amine of N, N-；3', 6'- dimethoxy -9H-3,9'- carbazole.
And if only if only one X in raw material single compound be F or Br or I；When another is H, i.e. starting material click
It is reaction condition replaced halogen at azoles 3 and 6 only one are as follows: raw material compound M (1.0eq.) and 4- Methyl benzenesulfonyl
Protection reaction occurs in anhydrous DMF for chlorine (1.0eq.)；Then (R is followed successively by 9H- carbazole with compound R (1.0eq)；Hexichol
Amine；The bis- 4- tert-butyl carbazoles of 9H-；Double 4- tert-butyl diphenylamines；The bis- 4- methoxyl carbazoles of 9H-；3,9'- joins carbazole；N, N- are bis-
(phenyl) -9H- carbazole -3- amine；3', 6'- di-t-butyl -9H-3,9'- carbazole；Bis- (4- tert-butyl) phenyl -9H- carbazoles-of N, N-
3- amine；3', 6'- dimethoxy -9H-3,9'- carbazole) under the alkaline condition existing for K2CO3 (2.0eq) and CuI (0.1eq)
Ullman reaction occurs；It is finally deprotected under basic conditions, and obtain aromatic amine compound (foundation by recrystallizing purification
The difference of compound R successively obtains compound 21~30).Compound 26~30 can use respectively compound 21~25 as chemical combination
Object R participates in above-mentioned preparation method and obtains.
When two X are simultaneously F or Br or I in raw material single compound, i.e. starting material carbazole 3 and 6 while quilt
Replaced halogen atom, reaction condition are as follows: raw material compound M (1.0eq.) is with 4- toluene sulfonyl chloride (1.0eq.) anhydrous
Protection reaction occurs in DMF；Then (R is followed successively by 9H- carbazole with compound R (2.0eq)；Diphenylamines；The bis- 4- tert-butyl clicks of 9H-
Azoles；Double 4- tert-butyl diphenylamines；The bis- 4- methoxyl carbazoles of 9H-) the alkalinity item existing for K2CO3 (4.0eq) and CuI (0.2eq)
Ullman reaction occurs under part；It is finally deprotected under basic conditions, and obtain aromatic amine compound by recrystallizing purification
(difference according to compound R successively obtains compound 31~35).
Below it is Application Example of the compounds of this invention in Organic Light Emitting Diode (OLED) device:
The stepped construction of organic electroluminescence device used in the present embodiment can be following structure:
1. anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/hole blocking layer/electron transfer layer/
Electron injecting layer/cathode
2. anode/hole injection layer/electronic barrier layer/luminescent layer/hole blocking layer/electron transfer layer/electron injecting layer/
Cathode
3. anode/hole injection layer/electronic barrier layer/luminescent layer/electron transfer layer/electron injecting layer/cathode
4. anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/cathode
5. anode/hole transmission layer/electronic barrier layer/luminescent layer/hole blocking layer/electron transfer layer/cathode
6. anode/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/cathode
7. anode/hole transmission layer/luminescent layer // electron transfer layer/cathode
8. anode/hole transmission layer/electronic barrier layer/luminescent layer/cathode
9. anode/hole transmission layer/luminescent layer/cathode
10. anode/electronic barrier layer/luminescent layer/cathode
In above structure, preferred structure 3.However the structure of organic electroluminescence device is not limited to example described above.
Wherein obtained by stepped construction 3 based on the organic of the electroluminescent material that 3- benzoyl pyridine is receptor unit
Electroluminescent device, specific stepped construction are as follows:
Glass substrate/ITO/TAPC/mCP/ compound light-emitting layer/TmPyPB/LiF/Al.ITO is anode, and TAPC is as empty
Cave implanted layer, mCP are electronic barrier layer, TmPyPB as electron transfer layer, LiF as electron injecting layer, Al as cathode,
Wherein compound light-emitting layer also selects that DPEPO, mCBP, CBP, CP, mCP etc. are luminescent material doping master other than undoped
Body.
The preparation step of stepped construction luminescent device is as follows:
Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol is successively used to surpass transparent electro-conductive glass
Sound is cleared up 15 minutes, to remove the dirt of substrate surface.It is stand-by to be then put into 80 degrees Celsius of drying in insulating box.After drying
ITO substrate is handled 3 minutes with oxygen plasma build-up of luminance equipment, further removes organic attachment on surface.It is above-mentioned to have anode
The glass of ITO is placed in vacuum chamber, under vacuum condition 1 × 10-5~9 × 10-3Pa, withDeposition rate in anode film
Upper vapor deposition organic material layer leads to wherein DPEPO and luminescent material are individually positioned in two evaporation sources in vapor deposition luminescent layer
Certain deposition rate is crossed to control the mixed proportion of the two.Later again withDeposition rate be deposited LiF, with's
Deposition rate evaporating Al electrode, obtains the organic light emitting diode device of the present embodiment.
Organic electroluminescence device CIE chromaticity coordinates value made by the compound P16 of this implementation of an application example be (0.25,
0.51), maximum brightness 11400cd/m2, external quantum efficiency is 23.2% and power efficiency is 57.9lm/W.Basic characterization number
According to as shown in table 1.The present invention is more importantly advantage also resides in, now to be by the same compound (compound 15 and 33)
Donor confirmation nitrogen-free compared with the organic small molecule material of receptor nuclear unit (compound P15 is with P33) using 3- benzoyl pyridine
The benzophenone of action site is that receptor core small molecule material (compound BP-15 and BP-33) shows lower bright electricity
Pressure, higher current density, superior external quantum efficiency and more stable device lifetime, performance comparison data are listed in table
1。
Contrast material BP-16 and BP-33 structure used in application example of the invention is as follows.
The some materials that stepped construction described in application example of the invention is used carry out structure example explanation, but and unlimited
In the material ranges.
Table 1 indicates the test result of made OLED device performance
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by the embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (8)
1. being the small organic molecule photoelectric functional material of receptor unit based on 3- benzoyl pyridine, which is characterized in that have such as
Flowering structure general formula:
Wherein:
R is selected from aromatic amine unit shown in (1)-(35):
2. with according to it is described in claim 1 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional material
Preparation method, which is characterized in that receptor core presoma passes through under copper catalyst and alkaline condition with aromatic amine intermediate
The small organic molecule photoelectric functional material based on 3- benzoyl pyridine for receptor unit is prepared in Ullmann coupling reaction；
The receptor core presoma has a structure that
3. it is according to claim 1 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional material
Preparation method, which comprises the following steps:
By (6- bromopyridine -3- base) (phenyl) ketone, intermediate, cuprous iodide, 1,10- phenanthroline and natrium carbonicum calcinatum successively add
Enter in reaction flask, substitute nitrogen it is multiple after, paraxylene is added, back flow reaction under condition of nitrogen gas is after reaction, extensive to system
Multiple room temperature, with methylene chloride and saturated salt solution extracting and washing, recycling organic phase is simultaneously dry with anhydrous magnesium sulfate, and vacuum distillation removes
Solvent is removed, then crude product is by column chromatographic isolation and purification, obtains final product；
The intermediate is one of following compound:
Carbazole, diphenylamines, phenoxazine, phenthazine, 10H- phenthazine 5,5- dioxide, 9,9- dimethyl -9,10- dihydro a word used for translation
Pyridine, 10,10- dimethyl -5,10- dihydro-dibenzo aza-silicon ring, acridine -9-10H- ketone, 3,6- di-t-butyl carbazole, bis- (4-
Tert-butyl-phenyl) amine, 3,6- dimethoxy -9H- carbazole, 5- phenyl -5,10- dihydro, 10H- spiral shell [acridine -9,9'- fluorenes], 9,9-
Diphenyl-acridan, 10H- spiral shell [acridine -9,9'- xanthene], 10H- spiral shell [acridine -9,9'- thioxanthene], 10H- spiral shell [a word used for translation
Pyridine -9,9'- thioxanthene] 10', 10'- dioxide, 10', 10'- dimethyl 10H, 5', 5'- dimethyl 5'H, 10H- spiral shell [acridine]
9,10' dibenzo silicon ring, 10H, 10'H- spiral shell [acridine -9,9'- anthracene] -10' ketone, bis- carbazole of 9H-3,9'-, N, N- diphenyl -9H-
Carbazole -3- amine, 3', two carbazole of 6'- di-t-butyl -9H-3,9'-, N, bis- (4- tert-butyl) phenyl -9H- carbazole -3- amine of N-, 3',
Two carbazole of 6'- dimethoxy -9H-3,9'-, 9H-3,9':3', 9 "-carbazole, N, N- diphenyl -9H- [bis- carbazole of 3,9'-] -3'-
Amine, 3 ", 6 "-dimethoxy -9- methyl -4 " a, 9 " a dihydro -9H-3,9-':3', 9 "-three carbazoles, N, the bis- (4- (tert-butyl) of N-
Phenyl) -9H- [3,9'-bicarbazol] -3'- amine, 3', 6 "-dimethoxy -9- methyl -4 ", 9 "-dihydro -9H-3,9', 3',
9 "-three carbazoles, 9'H-9,3':6', 9 "-three carbazoles, N3, N3, N6, N6- tetraphenyl -9H- carbazole -3,6- diamines, 9'H-9,3':
6', 9 "-tri-tert carbazoles, N3, N3, N6, N6- tetra- (4- (tert-butyl) phenyl) -9H- carbazole -3,6- diamines, 3,3 ", 6,6 " -
Tetramethoxy -9'H-9,3':6', 9 "-three carbazoles.
4. it is according to claim 3 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional material
Preparation method, which is characterized in that the refluxed under nitrogen, specifically:
150~180 DEG C back flow reaction 20~24 hours under condition of nitrogen gas.
5. answering based on the small organic molecule photoelectric functional material that 3- benzoyl pyridine is receptor unit described in claim 1
With, which is characterized in that it is applied to organic electro-optic device as luminescent material.
6. it is according to claim 5 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional material
Application, which is characterized in that the organic electro-optic device include 3- benzoyl pyridine be receptor unit small organic molecule
Photoelectric functional material participates in the organic sensitized luminescence device for the sharp base composite luminescence layer to be formed.
7. according to claim 5 and 6 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional
The application of material, which is characterized in that the organic electro-optic device includes transparent substrate, and the anode layer being formed on substrate,
At least one layer of organic thin film layer and cathode layer, the organic thin film layer are that 3- benzoyl pyridine is based on described in claim 1
For the small organic molecule photoelectric functional material of receptor unit any one or at least two combination.
8. it is according to claim 7 based on 3- benzoyl pyridine be receptor unit small organic molecule photoelectric functional material
Application, which is characterized in that the organic thin film layer further includes hole injection layer, hole transmission layer, electronic barrier layer, hole resistance
In barrier, electron transfer layer and electron injecting layer any one or at least two combination.
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| CN110079305A (en) * | 2019-05-24 | 2019-08-02 | 武汉华星光电半导体显示技术有限公司 | Navy blue thermal activation delayed fluorescence material and its production method, electroluminescent device |
| CN113278018A (en) * | 2020-02-20 | 2021-08-20 | 苏州大学 | Pyridine-based thermally activated delayed fluorescent material and application thereof |
| CN112898964A (en) * | 2021-02-05 | 2021-06-04 | 华南理工大学 | Sky blue light organic electroluminescent material and preparation method thereof |
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