CN108947927A - A kind of alcohol of side chain heteroaromatic containing high electron mobility/water solubility small organic molecule cathode interface material - Google Patents
A kind of alcohol of side chain heteroaromatic containing high electron mobility/water solubility small organic molecule cathode interface material Download PDFInfo
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- CN108947927A CN108947927A CN201811017055.8A CN201811017055A CN108947927A CN 108947927 A CN108947927 A CN 108947927A CN 201811017055 A CN201811017055 A CN 201811017055A CN 108947927 A CN108947927 A CN 108947927A
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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Abstract
The present invention provides the preparation method of the small organic molecule cathode interface material of a kind of side chain heteroaromatic containing high electron mobility and its is applied in organic solar batteries as cathode interface layer.The present invention on the side chain of small organic molecule by introducing high electron mobility heteroaromatic, improve the electronic transmission performance of small organic molecule boundary material, enhance its thickness insensitivity, to improve the efficiency of organic solar batteries, conducive to the wet process large-scale industrial production of organic solar batteries solar energy.Such material is used as boundary layer can also effectively prevent the device performance as caused by the reasons such as moisture, oxygen and light from declining, to significantly improve the stability of organic solar batteries.Meanwhile this kind of alcohol/water solubility organic small molecule material synthesis step is simple, low in raw material price, has great advantage in commercial applications.Using such boundary material organic solar batteries structure from bottom to top successively are as follows: transparent glass, indium-tin oxide anode, hole transmission layer, active layer, cathode interface layer and metallic aluminium cathode.
Description
Technical field
The present invention relates to organic solar battery material technical fields, and in particular to a kind of side chain is fragrant containing high electron mobility
The alcohol of heterocycle/water solubility small organic molecule cathode interface material preparation method and its application in organic solar batteries.
Technical background
Since the industrial revolution, the increase of geometry rank is presented in the use of the energy, most main for human social development at present
The energy wanted is traditional coal, oil and natural gas resource, but since traditional energy has non-renewable, is seriously threatened
The sustainable development of human society.Meanwhile the use of traditional energy also brings high risks to environment for human survival, affects
The health and existence of the mankind.Solar energy is that human society maintenance can as a kind of inexhaustible, nexhaustible renewable energy
The inevitable choice of sustainable development.Solar battery is as the device for directly converting solar energy into electric energy, in recent years by people
Very big concern.Especially organic solar batteries, due to its light weight, flexibility, can be roll-to-roll large-scale production the advantages that,
It is considered as the Typical Representative of next-generation solar battery.It is organic currently based on single layer under being continually striving to of researcher
The efficiency of solar battery has been over 14%.But due to generally making in the preparation process of traditional organic solar batteries
It uses active metal calcium as negative electrode interlayer, therefore great challenge is proposed to the encapsulation of device.With the development of cathode interface
With the use of alcohol/water-soluble cathode interface layer, the stability and efficiency of organic solar batteries obtain great promotion.
But alcohol used at present/water solubility cathode interface material electric conductivity is poor, therefore during the preparation process to interface thickness
Degree has strict requirements, and general thickness is controlled in 5 rans, and such precision is unfavorable for later large-scale industrial production.
The present invention provides the preparation method of a kind of cathode interface layer material insensitive to film thickness, i.e., has thiadiazoles and oxadiazoles etc.
The heteroaromatic unit of high electron mobility is introduced into the side chain of small organic molecule boundary material, is improved the electric conductivity of material, is changed
It is apt to its embellishing cathode interface ability, provides technical guarantee to prepare the insensitive efficient cathode interface layer of film thickness.
The present invention will contain 2,5- diphenyl -1,3,4- thiadiazoles and 2,5- diphenyl -1,3,4- oxadiazoles flexibility respectively
The monomer of side chain is prepared for a kind of alcohol/water-soluble small organic molecule cathode interface layer material by the method that Suzuki is coupled,
By the introducing of these high electron mobility structural units, the electric conductivity of material is effectively improved, is prepared unwise to film thickness
The cathode interface layer material of sense solves the problems, such as that organic solar batteries are not suitable for large-scale production.
Summary of the invention
Based on the above, it is an object of the invention to propose organic small point of alcohol/water solubility of a kind of high electron mobility
Sub- cathode interface material, and be applied in organic solar batteries as cathode interface layer.It is important that passing through introducing
The excellent functional groups of electronic transmission performances such as thiadiazoles/oxadiazoles, improve its film thickness insensitivity, are conducive to organic in the future
The wet process large-scale industrial production of solar battery.
The technical solution of the present invention is as follows:
The present invention provides the alcohol of a kind of high electron mobility/water-soluble small organic molecule cathode interface material, such
Small organic molecule cathode interface material has following general formula:
Wherein, R is the C that bromination front three ammonium is contained in end1-C12Alkyl；A is selected and is moved shown in formula II containing high electronics
The heteroaromatic functional group of shifting rate, wherein R1For C1-C12Alkyl or alkoxy；X is the hetero atoms such as O, S, Se or Te.
Preferred scheme, R1For C2-C8Alkoxy；X is O or S atom, and A selects group knot shown in formula III and formula IV
Structure:
2. small organic molecule cathode interface material as described in claim 1, it is characterised in that R preferentially selects C2-C8It is straight
Alkyl group or alkoxy.
3. small organic molecule cathode interface material as described in claim 1, it is characterised in that X preferentially selects the miscellaneous original of O and S
Son.
4. small organic molecule cathode interface material as described in claim 1, it is characterised in that A preferentially selects following knot
Structure:
Wherein R1For C2-C8Alkoxy.
Molecular structural formula below is most preferably had based on small organic molecule cathode interface material:
Main advantages of the present invention are:
1. the small organic molecule cathode interface material of invention has good alcohol/water solubility, it is strong that methanol etc. can be dissolved in
Polar solvent, solubility in methylene chloride is limited, therefore fits through orthogonal solvents method and prepare device.
2. the small organic molecule cathode interface material of invention has good cathodic modification ability, can effectively reduce
The work function of metallic cathode improves the Ohmic contact with active layer, reduces contact resistance.
3. the small organic molecule cathode interface material electric conductivity with higher of invention is applied to organic solar batteries
In, when the device film thickness of preparation reaches 50 nanometers, it still can obtain higher energy conversion efficiency.
Detailed description of the invention
Fig. 1 is the uv-visible absorption spectroscopy of small organic molecule cathode interface material of the invention；
Fig. 2 is the photoelectric conversion efficiency figure of small organic molecule cathode interface material of the invention；
Fig. 3 is the J-V curve of small organic molecule cathode interface material O-TFBr of the invention in different film thickness；
Fig. 4 is the J-V curve of small organic molecule cathode interface material S-TFBr of the invention in different film thickness；
Fig. 5 is the structure using the organic solar batteries of such boundary material.
Specific embodiment
To make the objectives, technical solutions, and advantages of the present invention clearer, below in conjunction with specific embodiment, and reference
Attached drawing, the present invention is described in more detail.
Alcohol of the invention/water solubility small organic molecule cathode interface material synthetic route is as follows:
(i) sodium hydroxide (50%), tetrabutylammonium bromide, bromoalkane；(ii) 2-4,4,5,5- tetramethyl-[1,3,2]-two
Oxa- borine -9,9- two (3'- bromopropyl) fluorenes, four triphenyl phosphorus palladiums, Anhydrous potassium carbonate, toluene；(3) tetrahydrofuran, trimethyl
Amine
Embodiment 1
The preparation of compound O-TFBr
Specific step is as follows:
(1) synthesis of compound 1a
The bromo- 9H- fluorenes of 2,7- bis- (0.31 gram, 0.97 mM) and the tetrabutylammonium bromide of catalytic amount are added to degassing
In dimethyl sulfoxide (60 milliliters).Then 4 milliliters of sodium hydroxide solutions (50%) are added.Reaction solution becomes peony at this time.So
Instill dropwise afterwards dissolved with compound 2- (4- 2-bromomethylphenyl) -5- [the own oxygen phenyl of 4-]-[1,3,4] oxadiazoles (1.0 grams, 2.41
MM) dimethyl sulfoxide (40 milliliters) solution.Reaction solution gradually purpling during dropwise addition.Continue stirring 24 after being added dropwise
Hour.After reaction, reaction solution is poured into 400mL water, solid is precipitated.Filtering, dry cake.Then column chromatography purifies.
0.46 gram of product is obtained, yield 48.0%.
The nuclear magnetic spectrum of compound 1a are as follows:1H NMR(400MHz,CDCl3,δ/ppm):7.99-7.94(m,4H,-ArH),
7.70-7.64(m,1H,ArH),7.55-7.47(s,4H,-ArH),7.46-7.42(m,1H,ArH),7.39-7.36(m,2H,-
ArH),7.22-7.19(m,2H,-ArH),7.01-6.74(m,8H,-ArH),4.12-3.99(m,4H,-CH2-),3.49-
3.45(m,4H,-CH2-),1.83-1.75(m,4H,-CH2-),1.50-1.31(m,12H,-CH2-),0.94-0.86(m,6H,-
CH3).13C NMR(100MHz,CDCl3,δ/ppm):164.4,163.9,161.9,149.0,139.7,138.9,131.0,
130.6,128.6,127.6,125.9,122.2,121.5,120.9,116.1,114.9,68.2,57.2,45.3,31.6,
29.1,25.7,22.6,14.0.
(2) synthesis of compound 2a
By bis- (3- bromopropyl the base) -9H- fluorenes -2- boric acid frequencies of compound 1a (0.61 gram, 0.62 mM), 9,9- any ester
(0.83 gram, 1.56 mMs) is dissolved in 15 milliliters of degassed toluenes, and 5 milliliters of degassing unsaturated carbonate potassium solutions, argon gas is then added
Protection is lower to be added four triphenyl phosphorus palladium catalysts.Back flow reaction 24 hours.After reaction, 10 milliliters of water and 20 milliliter two is added
Chloromethanes.Organic layer is separated, organic layer is dry with anhydrous magnesium sulfate.Filtering, filtrate are concentrated to give crude product with rotary evaporator.Slightly
Product pillar layer separation obtains 0.92 gram of faint yellow solid, yield 49%.
The nuclear magnetic spectrum of compound 2a are as follows:1H NMR(400MHz,CDCl3,δ/ppm):7.90-7.59(m,22H,ArH),
7.39-7.36(m,6H,ArH),6.99-6.93(s,8H,ArH),4.04-3.96(s,4H,-CH2-),3.62-3.55(s,
4H,-CH2-),3.19-3.11(m,6H,-CH2-),2.45-2.18(m,6H,-CH2-),1.83-1.75(m,4H,-CH2-),
1.56-1.21(m,20H,-CH2-),0.93-0.86(m,6H,-CH3).13C NMR(100MHz,CDCl3,δ/ppm):164.4,
164.0,161.9,150.3,150.0,149.6,149.4,148.5,140.9,140.5,140.4,140.3,139.9,
139.7,133.8,133.5,131.0,128.6,127.4,127.4,127.3,127.0,126.6,126.4,125.8,
123.8,123.4,123.2,122.2,121.8,120.5,120.4,120.2,120.1,119.9,117.9,68.2,56.8,
54.3,54.2,45.6,43.5,37.2,34.7,31.5,29.1,27.4,25.7,22.6,14.1.
(3) synthesis of compound O-TFBr
Compound 2a (0.62 gram, 0.38 mM) is dissolved in 20 milliliters of tetrahydrofurans at 0 DEG C, at room temperature by three
Methylamine water solution (33%, 5 milliliters) is added drop-wise in reaction system dropwise, then heats to reflux, the reaction was continued 3 hours.Reaction
After, with rotary evaporation concentration of reaction solution to 2 milliliters, then it is added drop-wise to dropwise in 300 milliliters of acetone, a large amount of solids is precipitated,
Filter to obtain crude product.Crude product obtains 0.34 gram of product with pillar layer separation, yield 48.2%.
The nuclear magnetic spectrum of compound O-TFBr are as follows:1H NMR(400MHz,CDCl3,δ/ppm):8.27-8.09(m,4H,
ArH),8.05-7.83(m,10H,ArH),7.65-7.50(m,8H,ArH),7.49-7.40(m,6H,ArH),7.12-6.90
(m,6H,ArH),4.10-3.90(s,8H,-CH2-),3.25-3.11(m,4H,-CH2-),2.92-2.84(s,36H,-CH3-
Br),2.43-2.15(m,8H,-CH2-),1.86-1.65(m,4H,-CH2-),1.56-1.14(m,20H,-CH2-),0.94-
0.86(m,6H,-CH3).13C NMR(100MHz,CDCl3,δ/ppm):164.6,164.2,162.4,149.3,148.5,
142.7,140.8,140.7,140.2,139.2,131.0,128.4,127.8,127.7,126.8,126.5,125.2,
123.4,121.6,120.9,120.5,120.2,114.9,69.2,66.3,58.6,57.5,54.7,54.2,52.0,35.6,
31.4,30.8,29.4,28.8,25.4,22.3,18.0,13.0.
Embodiment 2
The preparation of compound S-TFBr
Specific step is as follows:
(1) synthesis of compound 1b
The tetrabutylammonium bromide of the bromo- 9H- fluorenes (0.31g, 0.97mmol) of 2,7- bis- and catalytic amount is added to the two of degassing
In methyl sulfoxide (60 milliliters).Then 4 milliliters of sodium hydroxide solutions (50%) are added.Reaction solution becomes peony at this time.Then
Instill dropwise dissolved with compound 2- (4- 2-bromomethylphenyl) -5- [the own oxygen phenyl of 4-]-[1,3,4] thiadiazoles (1.0 grams, 2.41 milli
Mole) dimethyl sulfoxide (40 milliliters) solution.Reaction solution gradually purpling during dropwise addition.It is small to continue stirring 24 after being added dropwise
When.After reaction, reaction solution is poured into 400 milliliters of water, solid is precipitated.Filtering, dry cake.Then column chromatography purifies.
0.46 gram of product is obtained, yield 48.0%.
The nuclear magnetic spectrum of compound 1b are as follows:1H NMR(400MHz,CDCl3,δ/ppm):7.98-7.87(m,14H,ArH),
7.84-7.78(m,2H,ArH),7.92-7.89(m,3H,ArH),7.76-7.74(m,3H,ArH),7.50-7.44(m,10H,
ArH),7.02-6.96(m,6H,ArH),4.04-4.00(t,4H,-CH2-),2.06-2.03(s,4H,-CH2-),1.49-1.46
(m,4H,-CH2-),1.37-1.34(m,6H,-CH2-),1.27-1.24(m,6H,-CH2-),0.93-0.91(t,6H,-CH3)13C NMR(100MHz,CDCl3,δ/ppm):167.0,161.6,161.5,149.3,146.5,141.3,139.1,138.9,
138.5,138.3,132.7,131.7,130.9,130.8,129.4,128.8,128.4,127.9,127.8,120.1,
127.6,126.9,122.5,121.6,120.8,115.0,68.2,65.9,57.2,53.5,46.1,45.1,31.6,29.4,
29.1,25.7,22.6,14.1.
(2) synthesis of compound 2b
By bis- (3- bromopropyl the base) -9H- fluorenes -2- boric acid frequencies of compound 1b (0.63 gram, 0.62 mM), 9,9- any ester
(0.83 gram, 1.56 mMs) is dissolved in 15 milliliters of degassed toluenes, and 5 milliliters of degassing unsaturated carbonate potassium solutions, argon gas is then added
Protection is lower to be added four triphenyl phosphorus palladium catalysts.Back flow reaction 24 hours.After reaction, 10 milliliters of water and 20 milliliter two is added
Chloromethanes.Organic layer is separated, organic layer is dry with anhydrous magnesium sulfate.Filtering, filtrate are concentrated to give crude product with rotary evaporator.Slightly
Product pillar layer separation obtains 0.47 gram of faint yellow solid, yield 46.3%.
The nuclear magnetic spectrum of compound 2b are as follows:1H NMR(400MHz,CDCl3,δ/ppm):7.90-7.59(m,22H,ArH),
7.39-7.36(m,6H,ArH),6.97-6.95(s,8H,ArH),4.02-3.99(s,4H,-CH2-),3.62-3.58(s,
4H,-CH2-),3.18-3.11(m,6H,-CH2-),2.45-2.18(m,6H,-CH2-),1.83-1.75(m,4H,-CH2-),
1.55-1.16(m,20H,-CH2-),0.94-0.86(m,6H,-CH3).13C NMR(100MHz,CDCl3,δ/ppm):149.8,
149.4,148.7,140.8,140.5,140.4,140.2,139.9,133.6,131.2,129.4,128.3,127.6,
127.4,126.9,126.8,126.6,123.3,122.6,121.8,121.4,120.5,120.4,120.2,120.1,
117.9,115.0,66.3,56.6,54.3,54.2,45.4,44.9,38.6,34.7,31.5,29.1,27.4,27.2,25.7,
22.6,14.1.
(3) synthesis of compound S-TFBr
Compound 2b (0.47 gram, 0.28 mM) is dissolved in 20 milliliters of tetrahydrofurans at 0 DEG C, at room temperature by three
Methylamine water solution (33%, 5 milliliters) is added drop-wise in reaction system dropwise, then heats to reflux, the reaction was continued 3 hours.Reaction
After, with rotary evaporation concentration of reaction solution to 2 milliliters, then it is added drop-wise to dropwise in 300 milliliters of acetone, a large amount of solids is precipitated,
Filter to obtain crude product.Crude product obtains 0.26 gram of product with pillar layer separation, yield 49.2%.
The nuclear magnetic spectrum of compound S-TFBr are as follows:1H NMR(400MHz,CDCl3,δ/ppm):8.21-8.09(m,4H,
ArH),7.85-7.63(m,14H,ArH),7.55-7.40(m,10H,ArH),7.02-6.90(m,8H,ArH),4.00-3.80
(s,8H,-CH2-),3.35-3.11(m,4H,-CH2-),2.92-2.84(s,36H,-CH3-Br),2.13-2.45(m,8H,-
CH2-),1.65-1.86(m,4H,-CH2-),1.14-1.56(m,20H,-CH2-),0.94-0.86(m,6H,-CH3).13C NMR
(100MHz,CDCl3,δ/ppm):168.2,167.7,161.9,149.4,148.5,141.8,140.8,140.7,140.2,
139.1,131.2,129.1,127.9,127.7,127.4,126.7,126.5,126.2,123.4,121.8,121.5,
120.6,120.2,114.9,68.0,66.3,58.8,57.4,54.3,54.2,52.0,35.6,31.4,29.4,28.9,
25.5,22.3,18.0,13.1.
Embodiment 3
The preparation of organic solar batteries device
Specific step is as follows:
4 milligrams PTBT and 6 milligram of PC71BM mixing is added 0.5 milliliter of chlorobenzene dissolution, obtains active layer solution, spare.
The PEDOT:PSS transparent membrane for preparing one layer about 40 nanometers on indium tin oxide-coated glass by way of spin coating, 140
It anneals 15 minutes at DEG C.Then the electro-conductive glass after annealing is transferred in glove box, the above-mentioned prepared active layer of spin coating is molten
Then liquid is deposited by way of spin coating by the methanol solution of the cathode interface layer of the O-TFBr of configured 0.5 mg/litre
On active layer.The metallic aluminium electricity of one layer of 100 nanometer thickness is deposited on cathode interface layer finally by the mode of vacuum evaporation
Pole.The performance of its solar cell device are as follows: short circuit current is 17.64 milliamps per square centimeter；Open-circuit voltage is 0.78 volt
It is special；Fill factor is 73.4%；Energy conversion efficiency under simulated solar irradiation (100 milliwatts of A.M.1.5/square centimeter) is
10.10%.
Embodiment 4
The preparation of organic solar batteries device
Specific step is as follows:
4 milligrams PTBT and 6 milligram of PC71BM mixing is added 0.5 milliliter of chlorobenzene dissolution, obtains active layer solution, spare.
The PEDOT:PSS transparent membrane for preparing one layer of about 40nm on present indium tin oxide-coated glass by way of spin coating, 140
It anneals 15 minutes at DEG C.Then the electro-conductive glass after annealing is transferred in glove box, then spin coating active layer solution will match
The cathode interface layer material of the S-TFBr for 0.5 mg/litre set is deposited on active layer by way of spin coating.Finally lead to
The metal aluminium electrode of one layer of 100 nanometer thickness is deposited in the mode for crossing vacuum evaporation on cathode interface layer.Its solar cell device
Performance are as follows: short circuit current be 17.22 milliamps per square centimeter；Open-circuit voltage is 0.78 volt；Fill factor is
70.4%；In simulated solar irradiation (AM 1.5；100 milliwatts/square centimeter) under energy conversion efficiency be 9.45%.
Embodiment 5
Compound O-TFBr and S-TFBr performance evaluation is as follows:
(1) spectrum analysis of compound O-TFBr and S-TFBr
Absorption spectrum of the compound O-TFBr and S-TFBr under methanol solution and film-forming state is as shown in Figure 1, compound
There is obvious absorption in 200-400 nanometer range, can't compete absorb with active layer in solar cells.
(2) the photovoltaic performance analysis of compound O-TFBr and S-TFBr
The photovoltaic performance of compound O-TFBr and S-TFBr are as shown in Figure 2.The result shows that based on O-TFBr's and S-TFBr
Device all has good photovoltaic performance.Shorted devices electric current based on compound S-TFBr is 17.22 milliamps per square centimeter；
Open-circuit voltage is 0.78 volt；Fill factor is 70.4%, in simulated solar irradiation (AM 1.5；100 milliwatts/square centimeter) under
Energy conversion efficiency is 9.45%.Shorted devices electric current based on O-TFBr is 17.64 milliamps per square centimeter；Open-circuit voltage is
0.78 volt；Fill factor is 73.4%, in simulated solar irradiation (AM 1.5；100 milliwatts/square centimeter) under energy convert effect
Rate is 10.10%.Detailed data are referring to table 1.
Table 1 is based on PTB7:PC71BM is active layer, device parameters when O-TF or S-TF are boundary layer
O-TFBr and S-TFBr photovoltaic data in the case of different film thickness as shown in figure 3, detailed data referring to table 2.Knot
Fruit shows the functional group that high electron-transporting is introduced by side chain, significantly enhances the electron mobility of device, the effect of device
Rate is insensitive for the thickness of cathode interface material.
2 cathode interface layer of table is based on PTB7:PC under different film thickness71The device parameters of BM active layer
In conclusion the present invention provides alcohol/water solubility small organic molecule yin that a kind of side chain contains high electron mobility
Pole boundary material.This kind of material all has preferable solubility property in methyl alcohol, machine can be had by orthogonal solvents legal system too
Positive energy battery device.Heteroaromatic due to introducing high electronic transmission performance is conjugated side chain, this organic micromolecule boundary material
With preferable electric conductivity, there is film thickness insensitivity, be suitable for the large-scale industry preparation of organic solar batteries.With this hair
When material provided by bright is as cathode interface layer, the device efficiency more than 10% is obtained.
The discussion of any of the above embodiment is merely illustrative, it is not limited to range disclosed by the invention (including right is wanted
It asks).The combination and non-Tongfang between technical characteristic in order to brief and concise, under thinking of the invention, in different embodiments
Other variations in face, there is no provide completely in details.Therefore, all within the spirits and principles of the present invention, that is done appoints
How to omit, modification, on an equal basis replacement, improvement etc., is all included in the scope of protection of the present invention.
Claims (5)
1. a kind of alcohol of side chain heteroaromatic containing high electron mobility/water solubility small organic molecule cathode interface material, feature exist
In with molecular structure shown in formula (I):
Wherein, R is the C that bromination front three ammonium is contained in end1-C12Alkyl；A, which is selected, contains high electron mobility shown in formula II
Heteroaromatic functional group, wherein R1For C1-C12Alkyl or alkoxy；X is O, S, Se or Te hetero atom；
2. small organic molecule cathode interface material as described in claim 1, which is characterized in that R preferentially selects C2-C8Straight chain
Alkyl or alkoxy.
3. small organic molecule cathode interface material as described in claim 1, which is characterized in that X preferentially selects O or S hetero atom.
4. small organic molecule cathode interface material as described in claim 1, which is characterized in that A preferentially selects having structure:
Wherein R1For C1-C12Alkyl or alkoxy.
5. small organic molecule cathode interface material according to claim 4, which is characterized in that R1Preferential selection C2-C8It is straight
Alkyl group or alkoxy.
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| US20090230362A1 (en) * | 2008-01-25 | 2009-09-17 | Bazan Guillermo C | Conjugated oligoelectrolyte electron transporting layers |
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| US20090230362A1 (en) * | 2008-01-25 | 2009-09-17 | Bazan Guillermo C | Conjugated oligoelectrolyte electron transporting layers |
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| RENQIANG YANG等: "Conjugated Oligoelectrolyte Electron Transport/Injection Layers for Organic Optoelectronic Devices", 《J.AM.CHEM.SOC.》 * |
| THU TRANG DO等: "Synthesis and Characterization of Conjugated Oligoelectrolytes Based on Fluorene and Carbazole Derivative and Application of Polymer Solar Cell as a Cathode Buffer Layer", 《MACROMOLECULAR RESEARCH》 * |
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