CN109836369B - Spiroindene hole transport small molecule and application thereof in perovskite solar cell - Google Patents
Spiroindene hole transport small molecule and application thereof in perovskite solar cell Download PDFInfo
- Publication number
- CN109836369B CN109836369B CN201711203618.8A CN201711203618A CN109836369B CN 109836369 B CN109836369 B CN 109836369B CN 201711203618 A CN201711203618 A CN 201711203618A CN 109836369 B CN109836369 B CN 109836369B
- Authority
- CN
- China
- Prior art keywords
- hole transport
- spiroindene
- solar cell
- perovskite solar
- small molecule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Photovoltaic Devices (AREA)
Abstract
The invention provides a hole transport small molecule material containing a spiroindene structure. The spiroindene structure is taken as a core, and the spiroindene structure has Spiro atom connection similar to that of a classical material Spiro-OMeTAD and has better solubility; and a carbazole triphenylamine branch unit is introduced, so that better HOMO energy level and hole mobility can be ensured. The compound is used as a hole transport layer in a perovskite solar cell, and the photoelectric conversion efficiency can reach 18.55 percent at most.
Description
Technical Field
The invention relates to the field of perovskite solar cells, in particular to a preparation method of hole-transport small molecules containing a spiroindene structure and application of the hole-transport small molecules in perovskite solar cell devices.
Background
In recent years, the environmental problems caused by the energy crisis and the combustion of fossil energy are more and more emphasized by people, and the development of renewable and environment-friendly new energy is imperative. Among them, solar energy is the most clean and inexhaustible solar energy, and is very important for the sustainable development of human society. The development of new solar cells with low cost and high efficiency has become a research focus in recent years. The perovskite solar cell is developed rapidly, and the device efficiency is 3.8 percent of that in the first 2009[1]Quickly increased to 22.1% in 2016[2]The solar cell has attracted the attention of the world and is one of the research hotspots in the field of the novel solar cell at present.
CH3NH3PbI3(MAPbI3) The perovskite material has a plurality of advantages, such as high extinction coefficient and proper band gap[3]Low exciton confinement energy[4]Long charge diffusion distance[5]Carrier mobilityHigh mobility rate[6]Wide spectrum absorption range[7]And the like, and is very suitable for being used as a light absorption material of a solar cell. The main reason for the rapid improvement of the efficiency of such battery devices is the optimization of the perovskite material composition and the preparation method[8]And development of novel highly efficient charge collecting materials[9]. Charge collection materials, including electron transport materials and Hole Transport Materials (HTM), are an essential part in driving perovskite solar cell devices to achieve higher efficiency and higher stability[10]。
The spirofluorene micromolecule Spiro-OMeTAD is used as a hole transport layer material, combines with an excellent perovskite preparation method, has realized the device efficiency of more than 20 percent, and is the most widely used classical hole transport material at present[11]. However, for synthesizing Spiro-OMeTAD, 2 ', 7, 7 ' -tetrabromo-9, 9 ' -spirofluorene is used as a reaction raw material, and the synthesis process of the raw material needs to maintain low temperature condition of-78 ℃ and the use of chemical reagent (n-butyl lithium or Grignard reagent) which is sensitive to temperature and humidity and liquid bromine (which has extremely strong toxicity and corrosiveness and is volatile). In addition, the synthesized Spiro-OMeTAD needs to be further purified through a sublimation process to obtain higher device performance. These problems raise the synthesis cost of Spiro-OMeTAD[12]Limiting its large-scale application. Therefore, the development of a novel hole transport material with high efficiency and low cost is of great significance.
Disclosure of Invention
The invention provides a hole transport small molecule material containing a spiroindene structure. The hole transport material takes a Spiro indene structure as a core, has Spiro atom connection similar to that of a classical material Spiro-OMeTAD, and has better solubility; the carbazole triphenylamine dendritic unit is introduced, so that better HOMO energy level and hole mobility can be ensured, and the carbazole triphenylamine dendritic unit and the hole mobility are combined to ensure that the material has excellent device performance.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
a micromolecule containing a spiroindene structure is characterized in that the micromolecule has the following chemical structural formula:
the symbols and indices in the formula have the following meanings:
R1is H, -OH, C1-C3-alkoxy or C1-C3-an alkyl group;
a. b is identical or different and is 0,1 or 2;
G1、G2are the same or different and are represented by the following structural formula:
the symbols and coefficients in the formula have the following meanings:
c is the same or different and is 0,1 or 2;
Ar1、Ar2、Ar3are the same or different and are the following structural units
In the formula2Is H, C1-C10-alkyl or C1-C10-an alkoxy group;
Ar1′、Ar2′、Ar3′、Ar4are the same or different and are the following structural units
In the formula3Is H, C1-C4-an alkyl group.
The second object of the present invention is to provide the application of the hole transport material containing spiroindene structure. The hole transport material is applied to the application field of perovskite solar cells, so that the perovskite solar cells have high photoelectric conversion efficiency and good repeatability. Taking the material compound a in example 1 as an example, and taking it as a hole transport layer, the prepared device is subjected to a photoelectric conversion efficiency test, and the conversion rate of the device can reach 18.55% at most.
The technical scheme for solving the technical problems is as follows: the application of the hole transport material containing the spiroindene structure in the perovskite solar cell device is disclosed.
The terms:
"NBS" refers to N-bromosuccimide, N-bromosuccinimide.
"DMF" refers to N, N-Dimethylformamide, N, N-Dimethylformamide.
“Pd2dba3", refers to three (two benzylidene acetonates) dipalladium.
“Pd(dppf)Cl2", refers to 1, 1' -bis (diphenylphosphino) ferrocene dichloropalladium (II).
"S-phos" refers to 2-dicyclohexylphosphine-2 ', 6' -dimethoxybiphenyl.
The invention has the beneficial effects that:
1. according to the hole transport material, the spiroindene structure is used for replacing classical 9, 9' -spirobifluorene, so that on one hand, Spiro atom connection in the classical material Spiro-OMeTAD is reserved, on the other hand, the solubility of the hole transport material is increased, and in addition, the hole transport material is easy to synthesize and purify and has lower synthesis cost; the introduced carbazole dendritic units are used for adjusting energy levels, and the units are introduced into molecules in a dendritic form, so that the molecules have a spatial three-dimensional structure, and material crystallization is avoided; meanwhile, the thermal stability of the material can be greatly improved, and the efficiency of the battery is further improved; in addition, the dendritic space three-dimensional structure can also increase the solubility of the material, improve the film forming property of the material and further reduce the requirement on the preparation of devices.
2. The preparation method of the hole transport material has the advantages of simple synthetic route and mild reaction conditions, and all related reactions are normal-pressure reactions; all reaction temperatures are completed at 0-110 ℃, and industrial production is easy to realize; the required raw materials are easily obtained and are all commercial products.
3. The hole transport material is applied to the application field of perovskite solar cells, so that the perovskite solar cells have high photoelectric conversion efficiency. Taking the material compound A as an example, and taking the material compound A as a hole transport layer, the prepared device is subjected to a photoelectric conversion efficiency test, and the conversion rate of the device can reach 18.55 percent at most.
4. The preparation method of the perovskite solar cell device has simple and easy operation steps, and the required raw materials and equipment are easy to purchase.
5. The spiroindene micromolecules obtained by the method have better film forming property, and when the spiroindene micromolecules are used as a hole transport layer of a perovskite solar cell device, the usage amount of materials is less. Taking material compound a as an example, under the same device optimization conditions, the amount used is 1/4 which is the amount used by the classical material Spiro-OMeTAD. Therefore, the obtained compound is a hole transport material with excellent performance.
Drawings
Fig. 1 is a structural view of a perovskite solar cell device made of the hole transport material of the present invention.
In the drawings, the components represented by the respective reference numerals are listed below:
1. glass substrate, 2, FTO cathode, 3, compact TiO2Layer, 4, perovskite layer, 5, hole transport layer, 6, Au electrode.
Fig. 2 is a current-voltage curve of a perovskite solar cell device made with example 1 as the hole transport material.
FIG. 3 is an ultraviolet absorption spectrum of a tetrahydrofuran solution of example 1 and example 2.
FIG. 4 is a cyclic voltammogram of the dichloromethane solutions of example 1 and example 2.
Detailed Description
The following examples illustrate the present invention in more detail, but are not intended to limit the invention thereto.
The synthesis of the intermediate compounds required in the synthesis examples is as follows:
synthesis of Compound 2:
under an argon atmosphere, 4.6g (15mmol) of Compound 1, 8.3g (30mmol) of potassium carbonate and 50mL of DMF were mixed and stirred at room temperature, and then 2.4mL (19.5mmol) of methyl iodide was added dropwise. After stirring at room temperature for 12 hours, the reaction mixture was poured into 2500mL of water and filtered by suction to obtain 5g of a white product (yield 99%). LC-MS: c23H28O2Calculating the value: 336.21, found: [ M ] A]+＝336.21。1H NMR (400MHz, DMSO) δ 7.14(d, J ═ 8.3Hz,2H),6.79(dd, J ═ 8.3,2.3Hz,2H),6.19(d, J ═ 2.3Hz,2H),3.63(s,6H),2.23(d, J ═ 35.9Hz,4H),1.31(d, J ═ 29.1Hz,12H).
Synthesis of Compound 3:
10g (30mmol) of Compound 2 are dissolved in 100mL of DMF. A DMF solution containing 12g of NBS (84mmol) was added dropwise to the reaction mixture in an ice-water bath, and the mixture was stirred at room temperature for 12 hours. After the reaction, the reaction mixture was poured into 2000mL of water, and the mixture was filtered under suction to obtain 14g of a white product (yield 99%). LC-MS: c23H28Br2O2Calculating the value: 492.03, found: [ M ] A]+＝492.03。1H NMR(400MHz,CDCl3) δ 7.33(s,2H),6.29(s,2H),3.74(s,6H),2.27(d, J ═ 47.0Hz,4H),1.35(d, J ═ 20.5Hz,12H).
Synthesis of Compound 5:
under argon, 1.24g (2.5mmol) of Compound 3, 2.12g (5.75mmol) of Compound 4, and 0.032g (0.035mmol) of Pd2(dba)30.057g (0.14mmol) of phosphine ligand S-phos and 30mL of toluene are mixed and stirred. After the temperature was raised to 90 ℃, 10mL of an aqueous potassium carbonate solution (2M) was added, and the reaction was stirred for 12 hours. After the reaction was completed, toluene was evaporated to dryness, and then dichloromethane and water were added, followed by extraction, liquid separation, drying with anhydrous sodium sulfate, and silica gel column chromatography to obtain 1.02g (yield 50%) of a white solid. LC-MS: c59H50N2O2Calculating the value: 818.39, found: [ M ] A]+＝818.39。1H NMR(400MHz,CDCl3) δ 8.17(d, J ═ 7.7Hz,4H),7.83(d, J ═ 8.4Hz,4H),7.63(d, J ═ 8.4Hz,4H),7.54(d, J ═ 8.2Hz,4H), 7.46-7.40 (m,4H), 7.33-7.26 (m,6H),6.57(s,2H),3.79(s,6H),2.43(dt, J ═ 24.2,12.2Hz,4H),1.45(dd, J ═ 24.9,15.5Hz,12H), the synthetic route is as follows:
synthesis of Compound 6:
3.38g (4.13mmol) of Compound 5 are dissolved in 100mL of dichloromethane. 3.09g (17.346mmol) of NBS was added to the reaction mixture in portions in an ice-water bath, and after the addition, the temperature was naturally returned to room temperature, and the stirring was continued for 10 hours. After the reaction, the reaction mixture was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to obtain 4.60g of a white solid (yield 95%). LC-MS: c59H50Br4N2O2Calculating the value: 1130.03, found: [ M ] A]+＝1130.03。1H NMR(400MHz,CDCl3) δ 8.22(d, J ═ 1.8Hz,4H),7.83(d, J ═ 8.4Hz,4H), 7.57-7.50 (m,8H),7.39(d, J ═ 8.7Hz,4H),7.25(s,2H),6.56(s,2H),3.79(s,6H),2.44(dd, J ═ 38.0,13.0Hz,4H),1.48(d, J ═ 23.4Hz,12H).
Example 1
The synthesis of compound a is achieved by two schemes:
under argon, 1.14g (1mmol) of Compound 6, 1.1g (4.8mmol) of 4, 4' -dimethoxydiphenylamine, 0.036g (0.039mmol) of Pd2(dba)30.032g (0.158mmol) of tri-tert-butylphosphine, 0.77g (8mmol) of sodium tert-butoxide and 20mL of toluene are mixed and stirred, and the temperature is raised to 110 ℃ for reaction for 12 hours. After the reaction is finished, evaporating toluene to dryness, supplementing ethyl acetate and water, extracting, separating liquid, drying with anhydrous sodium sulfate, and using neutral alumina and n-hexaneThe eluent was mixed with ethyl acetate, and the column separation gave 1.00g of a yellow solid (yield 58%). LC-MS: c115H102N6O10Calculating the value: 1726.77, found: [ M ] A]+＝1726.77。1H NMR (400MHz, DMSO) δ 7.78(d, J ═ 8.3Hz,4H),7.73(d, J ═ 1.6Hz,4H),7.63(d, J ═ 8.4Hz,4H),7.36(d, J ═ 8.8Hz,4H),7.30(s,2H),7.11(dd, J ═ 8.9,1.6Hz,4H),6.88(d, J ═ 9.0Hz,16H),6.82(d, J ═ 9.0Hz,16H),6.55(s,2H),3.70(s,30H),2.36(dd, J ═ 32.4,12.8Hz,4H),1.43(d, J ═ 32.9Hz,12H), its absorption in tetrahydrofuran solution and its uv absorption curves in dichloromethane solution and cyclic synthesis are shown in fig. 3, which are as follows:
example 2 synthesis of compound B:
under argon, 1.14g (1mmol) of Compound 6, 0.965g (4.4mmol) of N-phenyl-1-naphthylamine, 0.036g (0.039mmol) of Pd2(dba)30.032g (0.158mmol) of tri-tert-butylphosphine, 0.77g (8mmol) of sodium tert-butoxide and 20mL of toluene are mixed and stirred, and the temperature is raised to 110 ℃ for reaction for 12 hours. After the reaction is finished, the toluene is evaporated to dryness, dichloromethane and water are added, extraction, liquid separation and anhydrous sodium sulfate drying are carried out, neutral alumina is used, a mixed solvent of normal hexane and ethyl acetate is used as an eluent, and column separation is carried out to obtain 0.98g of yellow solid (yield is 58%). LC-MS: c123H94N6O2Calculating the value: 1686.74, found: [ M ] A]+＝1686.74。1H NMR (400MHz, DMSO) δ 8.18(s,4H), 7.94-7.78 (m,14H),7.69(d, J ═ 7.8Hz,4H),7.55(t, J ═ 9.7Hz,8H), 7.46-7.29 (m,26H),7.13(d, J ═ 8.0Hz,6H),7.06(t, J ═ 7.3Hz,4H),7.00(d, J ═ 8.9Hz,4H),6.65(s,2H),3.83(s,6H),2.45(d, J ═ 19.9Hz,4H), 1.59-1.45 (m,12H), its ultraviolet absorption in tetrahydrofuran solution and cyclic voltammogram in dichloromethane solution were synthesized as shown in fig. 3 and fig. 4, as follows:
example 3
The hole transport material containing the spiroindene structure is applied to perovskite solar cell devices.
A perovskite solar cell device is shown in figure 1, and each layer comprises a glass substrate 1, an FTO cathode 2 and compact TiO in sequence2The hole transport layer 5 is prepared from the spirocyclic hole transport micromolecular material (such as the compound A) as described above.
The preparation process of the perovskite solar cell device comprises the following steps:
(1) cleaning: and ultrasonically cleaning the FTO glass substrate by using isopropanol, ethanol and secondary water in sequence to remove pollutants on the surface of the substrate, and drying the cleaned FTO glass substrate by using nitrogen. Treating with ultraviolet-ozone for 20min before use to further remove organic substances on the surface;
(2) compact TiO 22Preparation of the layer: preparing 0.2mol/L titanium tetrachloride aqueous solution, soaking a clean FTO glass substrate into the solution, and reacting for 1h in an oven at 70 ℃. After the reaction is finished, the compact TiO is taken out and deposited2Cleaning the FTO glass substrate with secondary water, and finally blowing the FTO glass substrate with nitrogen to dry, wherein the surface is kept clean and clean;
(3) preparation of perovskite active layer: densifying the deposited TiO2The FTO glass substrate is transferred into a glove box, and a perovskite precursor solution (mixed solvent, the volume ratio of DMF and DMSO is 4:1) with the concentration of 1mol/L is spin-coated to prepare a perovskite active layer with the thickness of 300nm, and the component structure is [ CH (NH)2)2PbI3]0.85(CH3NH3PbBr)0.15And annealing at 150 ℃ for 10min after spin coating.
(4) Preparation of hole transport layer: after the perovskite layer was cooled, a chlorobenzene solution of the spiroindene small molecule material compound A (concentration of 20mg/mL) was spin-coated, and 7.3. mu.L of 4-tert-butylpyridine and 4.4. mu.L of a lithium salt solution (520mg of Li-TFSI in 1mL of acetonitrile) were added.
(5) Preparation of Au anode: and placing the substrate on which the hole transport layer is spin-coated in a vacuum evaporation chamber, and carrying out vacuum evaporation on metal Au with the thickness of about 120nm to complete the preparation of the perovskite solar cell device.
The compound a prepared in example 1 is exemplified as a hole transport layer of the above-described solar cell device (perovskite solar cell) having a structure of: FTO glass substrate/dense TiO2Layer/[ CH (NH)2)2PbI3]0.85(CH3NH3PbBr)0.15(perovskite) layer/hole transport layer/Au electrode. I-V testing of the completed perovskite solar cell was performed, and as shown in FIG. 2, the short circuit current of the device was 24.68mA/cm2The fill factor was 70.9%, the open circuit voltage was 1.06V, and the energy conversion efficiency was 18.55%.
Reference documents:
[1]Kojima,A.；Teshima,K.；Shirai,Y.；Miyasaka,T.J.Am.Chem.Soc.,2009,131,6050–6051.
[2]NREL,Best Research-Cell Efficiencies,http://www.nrel.gov,accessed:November 2016.
[3]Eperon,G.E.；Stranks,S.D.；Menelaou,C.；Johnston,M.B.；Herz,L.M.；Snaith,H.J.Energy Environ.Sci.2014,7,982.
[4]Stranks,S.D.；Eperon,G.E.；Grancini,G.；Menelaou,C.；Alcocer,M.J.P.；Leijtens,T.；Herz,L.M.；Petrozza,A.；Snaith,H.J.Science 2013,342,341.
[5]Dong,Q.F.；Fang,Y.J.；Shao,Y.C.；Mulligan,P.；Qiu,J.；Cao,L.；Huang,J.S.Science 2015,347,967.
[6]Motta,C.；El-Mellouhi,F.；Sanvito,S.Sci.Rep.2015,5,12746.
[7]DeWolf,S.；Holovsky,J.；Moon,S.J.；
P.；Niesen,B.；Ledinsky,M.；Haug,F.J.；Yum,J.H.；Ballif,C.J.Phys.Chem.Lett.2014,5,1035.
[8]Song,T.B.；Chen,Q.；Zhou,H.；Jiang,C.；Wang,H.H.；Yang,Y.；Liu,Y.；You,J.；Yang,Y.J.Mater.Chem.A 2015,3,9032.
[9]Zhang,Y.；Liu,M.；Eperon,G.E.；Leijtens,T.C.；McMeekin,D.；Saliba,M.；Zhang,W.；de Bastiani,M.；Petrozza,A.；Herz,L.M.；Johnston,M.B.；Lin,H.；Snaith,H.J.Mater.Horiz.2015,2,315.
[10]Chen,W.；Wu,Y.；Yue,Y.；Liu,J.；Zhang,W.；Yang,X.；Chen,H.；Bi,E.；Ashraful,I.；
M.；Han,L.Science 2015,350,944.
[11]Yang,W.S.；Noh,J.H.；Jeon,N.J.；Kim,Y.C.；Ryu,S.；Seo J.；Seok,S.I.Science,2015,348,1234–1237.
[12]Malinauskas,T.；Saliba,M.；Matsui,T.；Daskeviciene,M.；Urnikaite,S.；Gratia,P.；Send,R.；Wonneberger,H.；Bruder,I.；Graetzel,M.；Getautis,V.；Nazeeruddin,M.K.,Energy.Environ.Sci.2016,9,1681-1686.
[13]Ma,X.；Swaidan,R.；Belmabkhout,Y.；Zhu,Y.；Litwiller,E.；Jouiad,M.；Pinnau,I.；Han,Y.,Macromolecules 2012,45,3841-3849.
[14]Lv,H.-j.；Ma,R.-f.；Zhang,X.-t.；Li,M.-h.；Wang,Y.-t.；Wang,S.；Xing,G.-w.,Tetrahedron 2016,72,5495-5501.
[15]You,J.；Li,G.；Wang,Z.,Polymer 2012,53,5116-5123.
[16]Xu,B.；Sheibani,E.；Liu,P.；Zhang,J.；Tian,H.；Vlachopoulos,N.；Boschloo,G.；Kloo,L.；Hagfeldt,A.；Sun,L.,Advanced Materials 2014,26,6629-6634.
[17] menghuhu encourage yellow vitamin an organic hole transport material (P) applied to all-solid-state perovskite sensitized solar cells, Chinese patent: CN 104230773A, 2014-12-24.
[18]Hanthorn,J.J.；Valgimigli,L.；Pratt,D.A.,J.Org.Chem.2012,77,6908-6916.
[19]Zhu,L.；Shan,Y.；Wang,R.；Liu,D.；Zhong,C.；Song,Q.；Wu,F.,Chem.Eur.J.2017,23,1-8.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (3)
1. A small molecule containing a spiroindene structure is characterized in that the chemical structural formula (I) is as follows:
The chemical structural formula (II) is as follows:
2. use of a small molecule comprising a spiroindene structure of claim 1 in a perovskite solar cell.
3. The perovskite solar cell as claimed in claim 2, which consists of a glass substrate layer, an FTO cathode layer, a dense TiO layer laminated in this order2The hole transport layer is prepared by taking the spiro hole transport micromolecule material as a hole transport material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711203618.8A CN109836369B (en) | 2017-11-27 | 2017-11-27 | Spiroindene hole transport small molecule and application thereof in perovskite solar cell |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711203618.8A CN109836369B (en) | 2017-11-27 | 2017-11-27 | Spiroindene hole transport small molecule and application thereof in perovskite solar cell |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109836369A CN109836369A (en) | 2019-06-04 |
| CN109836369B true CN109836369B (en) | 2022-06-07 |
Family
ID=66879987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711203618.8A Active CN109836369B (en) | 2017-11-27 | 2017-11-27 | Spiroindene hole transport small molecule and application thereof in perovskite solar cell |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109836369B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111635384B (en) * | 2020-07-03 | 2021-07-06 | 长春海谱润斯科技股份有限公司 | Arylamine organic compound and organic light-emitting device thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1424381A2 (en) * | 2002-11-26 | 2004-06-02 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, and display and illuminator |
| JP2004342391A (en) * | 2003-05-14 | 2004-12-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, lighting equipment and display unit |
| CN1587342A (en) * | 2004-07-09 | 2005-03-02 | 复旦大学 | Organic polymer material containing screw fluorene structure and its use |
| TW201229205A (en) * | 2010-12-20 | 2012-07-16 | Du Pont | Electroactive materials |
| CN102703058A (en) * | 2012-05-22 | 2012-10-03 | 烟台万润精细化工股份有限公司 | Novel electroluminescence material and application thereof |
| CN104091888A (en) * | 2014-07-17 | 2014-10-08 | 湖北大学 | Perovskite solar cell and preparation method thereof |
| CN104681731A (en) * | 2015-02-09 | 2015-06-03 | 南京工业大学 | Perovskite type electroluminescence device and preparation method thereof |
| CN104844464A (en) * | 2015-03-13 | 2015-08-19 | 中节能万润股份有限公司 | Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application |
-
2017
- 2017-11-27 CN CN201711203618.8A patent/CN109836369B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1424381A2 (en) * | 2002-11-26 | 2004-06-02 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, and display and illuminator |
| JP2004342391A (en) * | 2003-05-14 | 2004-12-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, lighting equipment and display unit |
| CN1587342A (en) * | 2004-07-09 | 2005-03-02 | 复旦大学 | Organic polymer material containing screw fluorene structure and its use |
| TW201229205A (en) * | 2010-12-20 | 2012-07-16 | Du Pont | Electroactive materials |
| CN102703058A (en) * | 2012-05-22 | 2012-10-03 | 烟台万润精细化工股份有限公司 | Novel electroluminescence material and application thereof |
| CN104091888A (en) * | 2014-07-17 | 2014-10-08 | 湖北大学 | Perovskite solar cell and preparation method thereof |
| CN104681731A (en) * | 2015-02-09 | 2015-06-03 | 南京工业大学 | Perovskite type electroluminescence device and preparation method thereof |
| CN104844464A (en) * | 2015-03-13 | 2015-08-19 | 中节能万润股份有限公司 | Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| 基于联苯、咔唑三苯胺空穴传输材料在钙钛矿太阳能电池中的应用;邵将洋等;《第四届新型太阳能学术研讨会论文集》;20170527;第248页 * |
| 有机电致发光空穴传输研究进展;马昌期等;《化学进展》;20031231;第15卷(第6期);第495-504页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109836369A (en) | 2019-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101823719B1 (en) | Naphtalene monoimide derivatives and use thereof as photosensitizers in solar cells and photodetectors | |
| CN106977491B (en) | Spiro [ fluorene-9, 9-xanthene ] hole transport material and application thereof | |
| CN109503457B (en) | Dinaphtho heterocyclic small molecule hole transport material, synthesis method and application thereof | |
| CN107021926A (en) | A kind of compound containing azepine spiro fluorene and nitrogenous hexa-member heterocycle and its application on OLED | |
| WO2020232973A1 (en) | DOUBLE D-π-A TYPE PILLAR[5]ARENE DYE, SYNTHESIS METHOD AND APPLICATION THEREOF | |
| CN106748832B (en) | Hole mobile material based on two fluorenes of spiral shell [3,3] heptane -2,6- spiral shells | |
| CN107056783A (en) | A kind of compound containing azepine spiro fluorene and nitrogenous hexa-member heterocycle and its application on organic electroluminescence device | |
| CN106432265B (en) | Thiophenes, its preparation method and application, perovskite solar cell | |
| CN109748909A (en) | The compound of a kind of fluorenes of xanthene containing spiral shell and nitrogenous hexa-member heterocycle, preparation method and its application in organic electroluminescence device | |
| TWI750333B (en) | Sensitizing dye, sensitizing dye composition for photoelectric conversion, photoelectric conversion element using the same, and dye-sensitized solar bettery | |
| CN109517142B (en) | Star-shaped D-A structure conjugated molecule based on tri-indeno five-membered aromatic heterocycle, and preparation method and application thereof | |
| CN104163785A (en) | A series of asymmetric squarine micromolecules containing indoline derivative structure, and application thereof | |
| Kula et al. | 9, 9′-bifluorenylidene derivatives as novel hole-transporting materials for potential photovoltaic applications | |
| CN110194778A (en) | A kind of multi-arm structure organic photovoltaic material and the preparation method and application thereof | |
| CN112266389B (en) | Benzimidazole organic compound and preparation method thereof | |
| CN109836369B (en) | Spiroindene hole transport small molecule and application thereof in perovskite solar cell | |
| CN109053735B (en) | Organic semiconductor material based on pyrrole-nucleus aromatic amines and application thereof | |
| CN114621276A (en) | Benzothiadiazole boron-nitrogen derivative and application thereof | |
| CN114409551A (en) | Fullerene derivative material, preparation method thereof and application thereof in perovskite solar cell | |
| CN111978515B (en) | Hole transport polymer containing benzyl alcohol group and application thereof | |
| CN109096163B (en) | Organic molecular material, synthesis method thereof and application of organic molecular material as hole transport layer | |
| CN107602545B (en) | Conjugated triphenylamine double-anchored pure organic dye linked by fluorene and application thereof in dye-sensitized solar cell | |
| CN111153914A (en) | Asymmetric hole transport material and preparation method and application thereof | |
| WO2015005869A1 (en) | Perylene functionalized porphyrin dyes for dye-sensitized solar cells | |
| CN109265468A (en) | Small molecule containing anti-aromaticity indacene unit and its application in photovoltaic |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |