CN101003516A - Dentritic pattern compound, preparation method and application - Google Patents
Dentritic pattern compound, preparation method and application Download PDFInfo
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- CN101003516A CN101003516A CNA2006100112252A CN200610011225A CN101003516A CN 101003516 A CN101003516 A CN 101003516A CN A2006100112252 A CNA2006100112252 A CN A2006100112252A CN 200610011225 A CN200610011225 A CN 200610011225A CN 101003516 A CN101003516 A CN 101003516A
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Abstract
This invention discloses three kinds of dentritic compounds based on cyano-substituted phenylquinoxaline, methyl-substituted phenylquinoxaline, and cyano-substituted phenylpyrazine. The preparation method comprises: reacting 4, 4'-dibromo dipheny ethanedione with trimethylsilico acetylene, reacting with tetraphenyl cyclopentanone to obtain a precursor, and reacting with 1, 2-diamino-4, 5-dicyanobenzene, 1, 2-diamino-4, 5-dimethylbenzene and 2, 3-diaminobutanedinitrile, respectively, to obtain corresponding dentritic compounds. The dentritic compounds can be used as luminescent and electron-transfer material to prepare OLED with high luminescent brightness and efficiency.
Description
Technical field
The present invention relates to a kind of dendritic compound.
The invention still further relates to the preparation method of above-claimed cpd.
The invention still further relates to the application of above-claimed cpd.
Background technology
Organic Light Emitting Diode (OLEDs) has been obtained significant progress so far since 1987 report (C.W.Tang, S.A.VanSlyke, Appl.Phys.Lett.1987,51,913).Owing to low cost, wide visual angle, the high-level efficiency of OLEDs, can be used for plurality of advantages such as flexible demonstrations, generally believed it is follow-on main flow demonstration and illuminating device.Recent two decades comes, and the electroluminescent material that the researchist has synthesized many novelties improves the luminous efficiency, brightness, stability, purity of color of OLEDs etc.Though great majority have higher fluorescence quantum yield in these materials in solution, and are but not high at the quantum yield of filminess, this is because material molecule forms state of aggregation easily when filminess, thereby has increased the probability of non-radiative energy decay.The second-order transition temperature of most materials is low simultaneously, and the joule heating that prepared OLEDs produces under bigger working current can make material molecule degraded, deformation etc., and then influences the stability of device.Consider that from the angle of molecular structure the nonplanarity that increases molecule can effectively prevent the formation of state of aggregation, improves the luminescent properties of material.Introducing branch type group to intramolecularly is to strengthen nonplanarity to weaken the morphogenetic effective means of gathering (A.Pogantsch, F.P.Wenzl, E.J.W.List, Adv.Mater.2002,14,1061; C.T.Chen, C.L.Chiang, Y.C.Lin, Org.Lett.2003,5,1261; C.Huang, C.G.Zhen, S.P.Su, Org.Lett.2005,7,391.), give molecule good thermostability simultaneously.The many phenyl groups of branch type have very big sterically hindered, thereby can effectively stop intermolecular gathering, but can reduce the transmission performance of current carrier simultaneously.Therefore, how to obtain existing high luminescent properties and high second-order transition temperature, the compound of carrier transmission performance is preferably arranged again, become the difficult problem that the researchist need endeavour to solve.
Summary of the invention
The object of the present invention is to provide a kind of dendritic compound.
Another purpose of the present invention is to provide a kind of method for preparing above-claimed cpd.
For achieving the above object, dendritic compound provided by the invention is the dendritic compound that contains many phenyl substituents of the pyrazine of three quinoxalines that replace based on cyano group respectively, methyl substituted quinoxaline, cyano group replacement; Its structure is suc as formula 1, shown in formula 2 and the formula 3:
Wherein:
Formula 1 is 6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (being designated hereinafter simply as CPQ);
Formula 2 is 6,7-dimethyl-2,3-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (being designated hereinafter simply as MPQ);
Formula 3 is 2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines (being designated hereinafter simply as CPP).
The thermal property and the electrochemical properties of above-claimed cpd see Table 1.
Table 1
| Compound | T g(℃) | T d(℃) | E 1/2(V) | E onset(V) | E HOMO(eV) | E LUMO(eV) |
| CPQ | 204 | 515 | -1.05 | -0.98 | -6.26 | -3.42 |
| MPQ | 197 | 488 | -1.71 | -1.63 | -5.74 | -2.58 |
| CPP | 189 | 450 | -1.11 | -1.05 | -6.30 | -3.35 |
T in the table
g: second-order transition temperature, T
d: decomposition temperature, E
1/2: half-wave potential, E
Onset: play spike potential, E
HOMO: highest occupied molecular orbital energy level, E
LUMO: the lowest unoccupied molecular orbital energy level.
Dendritic compound provided by the invention has high glass-transition temperature and better electron transport ability.
The method that the present invention prepares above-claimed cpd is as follows:
1) raw material 4, and 4 '-dibromo benzil and trimethylsilyl acetylene move into ethynyl through two-step reaction, generate 4,4 '-diacetylene benzil.
2) 4,4 '-diacetylene benzil and tetraphenyl cyclopentanone obtain precursor 4 through the Dields-Alder addition reaction, 4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils.
3) precursor and 1,2-diamino-4, the reaction of 5-dicyanobenzenes obtains target product CPQ.
4) precursor and 1,2-diamino-4, the reaction of 5-dimethyl benzene obtains target product MPQ.
5) precursor and 2, the reaction of 3-diamino succinonitrile obtains target product CPP.
Specifically, its main preparation process is:
The first step is preparation precursor 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzil earlier:
A) 4, the mol ratio of 4 '-dibromo benzil and trimethylsilyl acetylene is 1: 2-3, press the catalyst P d (pph that reactant weight adds 8-10%
3)
2Cl
2With the cocatalyst CuI of 3-5%, in toluene/triethylamine solution, 40-60 ℃ was stirred 8-12 hour down in the nitrogen atmosphere, removed and desolvated; Wherein the mol ratio of toluene and triethylamine is 1: 1;
B) product of step a and K
2CO
3In molar ratio 1: 8-10 stirred 4-6 hour under the room temperature in methylene dichloride, use dichloromethane extraction, and organic phase is removed and desolvated, must solid product;
C) product of step b 2-4 in molar ratio: 1 adds tetraphenylcyclopentadienone, in m-xylene solution, stirs 10-12 hour in 100-120 ℃ under the nitrogen atmosphere, remove and desolvate, 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils.
Second goes on foot with 44 '-two (2,3,4, the 5-tetraphenyl)-and the phenyl benzil prepares 6 respectively, 7-dicyano-2, and 3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (CPQ), 6,7-dimethyl-2,3-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (MPQ) and 2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines (CPP):
● with 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils are 0.3-0.5 in molar ratio: 1 adds 1,2-diamino-4, and the 5-dicyanobenzenes stirred 8-10 hour under the room temperature in the acetic acid solution, and removing desolvates obtains product C PQ;
● with 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils are 0.3-0.5 in molar ratio: 1 adds 1,2-diamino-4, and the 5-dimethyl benzene stirred 8-10 hour under the room temperature in the acetic acid solution, and removing desolvates obtains product MPQ;
● with 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils are 0.3-0.5 in molar ratio: 1 adds 1, and 2-diamino anti-maleic nitrile stirred 8-10 hour under the room temperature in the acetic acid solution, and removing desolvates obtains product C PP.
Described method, wherein the step a in the first step removes by underpressure distillation and desolvates.
Described method, wherein the step a gained solid product silicagel column purifying in the first step.
Described method, wherein step b in the first step and step c remove by rotary evaporation and desolvate.
Described method, wherein the step c in the first step removes the back of desolvating and makes eluant with methylene dichloride/sherwood oil of 1: 2 of mol ratio.
Described method is wherein all removed by rotary evaporation in three preparation processes in second step and is desolvated.
Described method wherein all uses methylene dichloride/sherwood oil of 1: 2 of mol ratio to make eluant except that after desolvating in three steps in second step.
Dendritic compound provided by the invention can prepare OLED as the luminescent material electron transport material of holding concurrently, and higher luminosity and efficient are arranged.
The present invention has following feature:
1) the synthetic compound has many phenyl replacements, forms branch type molecule.
2) contain stronger electron-withdrawing group in the compound molecule, make molecule that lower lowest unoccupied molecular orbital (LUMO) energy level be arranged.
The invention has the advantages that:
1) synthetic route is simple, productive rate height, the product purity height that obtains.
2) this compounds has good thermostability, and its decomposition temperature and second-order transition temperature are all very high.
3) this compounds has stronger electron-withdrawing power, is convenient to the injection and the transmission of electronics.
4) good prospects for application is arranged in OLED.
Description of drawings
Fig. 1: The compounds of this invention is at film and the fluorescence spectrum in chloroform soln.
Fig. 2: The compounds of this invention is at film and the ultra-violet absorption spectrum in chloroform soln.
Fig. 3: the organic LED structure synoptic diagram that The compounds of this invention is constructed.
Fig. 4: based on the electroluminescent spectrum of the OLEDs of The compounds of this invention.
Fig. 5: based on current density-voltage curve curve of the OLEDs of The compounds of this invention.
Fig. 6: based on brightness-voltage curve of the OLEDs of The compounds of this invention.
Embodiment
The present invention is described in detail below in conjunction with accompanying drawing and example.
Embodiment 1
The synthetic route of three compounds involved in the present invention is shown below
Prepare precursor 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzil earlier
Reaction i:
4,4 '-dibromo benzil (3.68g, 0.01mol), trimethylsilyl acetylene (2.36g, 0.024mol), catalyst P d (PPh
3)
2Cl
2(10%) and CuI (5%) toluene/triethylamine (1: 1) 40ml, 60 ℃ were stirred 12 hours under nitrogen atmosphere, and after reaction finished, underpressure distillation removed and desolvates.The solid product that obtains silicagel column purifying is 4,4 '-two-(trimethylsilyl acetylene base)-phenyl benzil except that obtaining yellow solid after desolvating.With 4, and 4 '-two-(trimethylsilyl acetylene base)-phenyl benzil (2.01g, 0.005mol) and K
2CO
3(6.9g, 0.05mol) in the 50mL methylene dichloride stirring at room 6 hours, after reaction was finished, the dichloromethane extraction aqueous solution use in washing, merged organic phase, dry back rotary evaporation is except that desolvating, the yellow solid that obtains is 4,4 '-diacetylene benzil.
Reaction ii:
With 4; 4 '-diacetylene benzil (645mg, 2.5mmol) and tetraphenylcyclopentadienone (460mg 0.65mmol) is dissolved in the 5ml m-xylene; stirred 12 hours for following 120 ℃ in nitrogen protection; cooling back rotary evaporation removes and desolvates, and makes eluant with methylene dichloride/sherwood oil (1: 2), crosses silicagel column and gets precursor 4; 4 '-two (2; 3,4, the 5-tetraphenyl)-the phenyl benzil.
Reaction iii: use precursor preparation CPQ
With 4, and 4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils (150mg 0.155mmol) is dissolved in 10ml acetate, adds 1 then, 2-diamino-4, and (47mg, 0.30mmol), stirring and refluxing 10 hours obtains yellow mercury oxide to the 5-dicyanobenzenes., make eluant with methylene dichloride/sherwood oil (2: 1) and obtain target product CPQ except that desolvating through rotary evaporation through the flash chromatography separation.
Mass spectrum: m/z 1093.8 (M
++ 1); Nucleus magnetic hydrogen spectrum [
1H NMR (CD
2Cl
2, 300MHz)]: δ=8.59 (s, 2H), 7.58 (s, 2H), 7.35 (d, 4H), 7.22 (m, 14H), 6.98-6.87 (m, 30H); Nuclear-magnetism carbon spectrum [
13C NMR (CD
2Cl
2, 75MHz)]: δ=158.3,145.2,143.2,142.9,142.8,142.2,141.5,141.2,141.1,140.5,138.0,136.4,132.8,132.7,132.5,132.2,131.2,131.1,130.6,128.8,128.1,127.8,127.6,127.1,126.9,126.7,116.5,115.2; Ultimate analysis: theoretical value C
82H
52N
4C90.08, H5.12, N4.79; Measured value C89.48, H4.99, N5.02.
Reaction iv: use precursor preparation MPQ
With 4, and 4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils (150mg 0.155mmol) is dissolved in 10ml acetate, adds 1 then, 2-diamino-4, and (47mg, 0.35mmol), stirring and refluxing 10 hours obtains white precipitate to the 5-dimethyl benzene., make eluant with methylene dichloride/sherwood oil (1: 2) and obtain target product MPQ except that desolvating through rotary evaporation through the flash chromatography separation.
Mass spectrum: m/z 1071.5 (M
++ 1); Nucleus magnetic hydrogen spectrum [
1H NMR (CD
2Cl
2, 300MHz)]: δ=7.87 (s, 2H), 7.60 (s, 2H), 7.28 (d, 4H), 7.22 (d, 10H), 7.14 (d, 4H), 7.00-6.86 (m, 30H), 2.55 (s, 6H); Nuclear-magnetism carbon spectrum [
13C NMR (CD
2Cl
2, 75MHz)]: δ=153.1,143.2,143.0,142.1,141.8,141.6,141.4,141.3,141.2,140.5,138.4,132.8,132.7,132.3,131.1,130.8,130.4,129.2,128.8,128.1,128.0,127.7,127.5,126.9,126.8,126.5,21.3; Ultimate analysis (%): theoretical value C
82H
58N
2C91.93, H2.61, N5.46; Measured value: C91.39, H2.60, N5.75.
Reaction v: use precursor preparation CPP
With 4, (150mg 0.155mmol) is dissolved in 10ml acetate to 4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils, adds 2 then, and (32mg, 0.30mmol), stirring and refluxing 10 hours obtains faint yellow precipitation to 3-diamino anti-maleic nitrile., make eluant with methylene dichloride/sherwood oil (2: 1) and obtain target product CPP except that desolvating through rotary evaporation through the flash chromatography separation.
Embodiment 2
The OLEDs preparation of devices:
The first step: the cleaning of tin indium oxide (ITO) glass
Ito glass cleans with washing composition, tap water, deionized water, acetone, dehydrated alcohol successively, places baking oven to dry then.
Second step: evaporation organic semiconductor layer
The ito glass sheet of cleaning is placed in the vacuum chamber, 4 * 10
-4Under the vacuum tightness of Pa, with each organic layer of speed evaporation of 2_/s.The total thickness of organic semiconductor layer is～100nm in the device.
The 3rd step: negative electrode preparation
Evaporating Al negative electrode on the ITO substrate of the intact organic layer of evaporation, thickness is 100nm.
The device architecture of preparation is seen Fig. 3.
The 4th step: the test of device performance
Above-mentioned device is tested under room temperature, atmospheric environment: current-voltage curve is recorded by the HP4140B semi-conductor test instrument; Luminous power is recorded by the NewPort2835C light power meter, can obtain light emission luminance value through conversion.
Listed the calorifics and the electrochemical properties of compound in the table 1, all about 200 ℃, decomposition temperature all is higher than 450 ℃ to its second-order transition temperature, shows that this compounds has excellent thermostability.The lumo energy of CPQ and CPP is all lower, about-3.4eV, shows to help the injection of electronics from negative electrode.
Fig. 1 is the fluorescence spectrum of compound under film and chloroform soln state, CPQ, MPQ, the fluorescence emission peak of CPP in film lays respectively at 493nm, 415nm, the 471nm place has only very little red shift (0～4nm) with respect to its emission peak in solution, show that this dendriform compound can effectively prevent the gathering of molecule under filminess, thereby reduced the fluorescent quenching of aggregation inducing.
Fig. 2 is the ultraviolet-visible absorption spectroscopy of compound under film and chloroform soln state, CPQ, MPQ, the peak position of the absorption maximum value correspondence of CPP in film lays respectively at 408nm, 371nm, the 372nm place also has only very little red shift with respect to its peak position in solution.
For testing the electroluminescent properties of these compounds, made up structure device as shown in Figure 3.Wherein tin indium oxide (ITO) is as anode; 4,4 '-two-(N-naphthyl-N-phenyl amino) biphenyl (NPB) are as hole transmission layer, and structure as shown in Equation 4;
Formula 4
4,4 '-two-(N-carbazyl)-2,2 '-biphenyl (CBP) are also as hole transmission layer, and energy barrier is injected in the hole that is used for reducing between NPB layer and the compound layer, and structure as shown in Equation 5;
Compound layer is represented CPQ respectively, MPQ, and CPP is as the luminescent layer electron transfer layer of holding concurrently; Aluminium is as negative electrode.The electroluminescent spectrum of these devices as shown in Figure 4.Current density-the voltage of device of preparation and brightness-voltage relationship as shown in Figure 5 and Figure 6, wherein the device based on CPP has the highest brightness 2904cd/m
2
Above result shows the second-order transition temperature of this compounds Yin Qigao and electron transport ability and luminous power preferably, so good prospects for application is arranged in OLEDs.
Claims (10)
1. a dendritic compound is the dendritic compound that contains many phenyl substituents of the pyrazine of three quinoxalines that replace based on cyano group respectively, methyl substituted quinoxaline, cyano group replacement; Its structure is suc as formula 1, shown in formula 2 and the formula 3:
Formula 1 formula 2 formulas 3
Wherein:
Formula 1 is 6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline;
Formula 2 is 6,7-dimethyl-2,3-[4-(2,3,4, the 5-tetraphenyl) phenyl]-the phenyl quinoxaline;
Formula 3 is 2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines;
2. dendritic compound as claimed in claim 1 is characterized in that, the thermal property of above-claimed cpd and electrochemical properties are shown in the following table:
T in the table
g: second-order transition temperature, T
d: decomposition temperature, E
1/2: half-wave potential, E
Onset: play spike potential, E
HOMO: highest occupied molecular orbital energy level, E
LUMO: the lowest unoccupied molecular orbital energy level.
3. the method for preparing the described dendritic compound of claim 1, its main preparation process is:
The first step is preparation precursor 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzil earlier:
A) 4, the mol ratio of 4 '-dibromo benzil and trimethylsilyl acetylene is 1: 2-3, press the catalyst P d (pph that reactant weight adds 8-10%
3)
2Cl
2With the cocatalyst CuI of 3-5%, in mol ratio was toluene/triethylamine solution of 1: 1,40-60 ℃ was stirred 8-12 hour down in the nitrogen atmosphere, remove and desolvate, solid product;
B) product of step a and K
2CO
3In molar ratio 1: 8-10 stirred 4-6 hour under the room temperature in methylene dichloride, washing, and the dichloromethane extraction aqueous solution merges organic being divided by to desolvate, must solid product;
C) product of step b 2-4 in molar ratio: 1 adds tetraphenylcyclopentadienone, in m-xylene solution, stirs 10-12 hour in 100-120 ℃ under the nitrogen atmosphere, remove and desolvate, 4,4 '-two (2,3,4, the 5-tetraphenyl)-phenyl benzils.
Second goes on foot with 44 '-two (2,3,4, the 5-tetraphenyl)-and the phenyl benzil prepares 6 respectively, 7-dicyano-2, and 3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline, 6,7-dimethyl-2,3-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline and 2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines:
● with 4,4 '-two (2,3,4,5-tetraphenyl)-and phenyl benzil 0.3-0.5 in molar ratio: 1 adds 1,2-diamino-4, the 5-dicyanobenzenes, stirred 8-10 hour under the room temperature in the acetic acid solution, removing desolvates obtains product 6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-the phenyl quinoxaline;
● with 4,4 '-two (2,3,4,5-tetraphenyl)-and phenyl benzil 0.3-0.5 in molar ratio: 1 adds 1,2-diamino-4, the 5-dimethyl benzene, stirred 8-10 hour under the room temperature in the acetic acid solution, removing desolvates obtains product 6,7-dimethyl-2,3-[4-(2,3,4, the 5-tetraphenyl) phenyl]-the phenyl quinoxaline;
● with 4,4 '-two (2,3,4, the 5-tetraphenyl)-and phenyl benzil 0.3-0.5 in molar ratio: 1 adds 1, and 2-diamino anti-maleic nitrile stirred 8-10 hour under the room temperature in the acetic acid solution, removing desolvates obtains product 2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines.
4. method as claimed in claim 3 is characterized in that, the step a in the first step removes by underpressure distillation and desolvates.
5. method as claimed in claim 3 is characterized in that, the step a gained solid product silicagel column purifying in the first step.
6. method as claimed in claim 3 is characterized in that, step b in the first step and step c remove by rotary evaporation and desolvate.
7. method as claimed in claim 3 is characterized in that, the step c in the first step removes the back of desolvating and makes eluant with methylene dichloride/sherwood oil of 1: 2 of mol ratio.
8. method as claimed in claim 3 is characterized in that, all removes by rotary evaporation in three preparation processes in second step and desolvates.
9. method as claimed in claim 3 is characterized in that, all uses methylene dichloride/sherwood oil of 1: 2 of mol ratio to make eluant except that after desolvating in three steps in second step.
10. the described dendritic compound of claim 1 is in the luminescent material electron transport material Application for Field of holding concurrently.
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