CN103247759A - Application of organic semiconductor material to organic semiconductor photoelectric device - Google Patents
Application of organic semiconductor material to organic semiconductor photoelectric device Download PDFInfo
- Publication number
- CN103247759A CN103247759A CN2013101796837A CN201310179683A CN103247759A CN 103247759 A CN103247759 A CN 103247759A CN 2013101796837 A CN2013101796837 A CN 2013101796837A CN 201310179683 A CN201310179683 A CN 201310179683A CN 103247759 A CN103247759 A CN 103247759A
- Authority
- CN
- China
- Prior art keywords
- formula
- organic semiconductor
- alkyl
- compound shown
- compound
- 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.)
- Granted
Links
Images
Landscapes
- Thin Film Transistor (AREA)
Abstract
The invention disclosesapplication of an organic semiconductor material to an organic semiconductor photoelectric device. In a formula I, R1, R2 and R a are selected from alkyl, aryl and alkyl-substituted aryl, wherein the alkyl is linear alkyl or branched alkyl with 1 to 16 carbon atoms; and the aryl is phenyl, fluorenyl, thienyl, fluorine-containing phenyl, nitrogen-containing heterocyclic radical or silicon-containing heterocyclic radical. By a substituent group in the compound shown in the formula I, the fluorescence emission wavelength of a material can move towards red light or blue light, and theapplication range is widened; and a new system is provided for an organic semiconductor photoelectric material. The organic semiconductor photoelectric device prepared from the compound has high sensitivity, high accuracy and high repeatability.
Description
Technical field
The present invention relates to the application of a kind of organic semiconducting materials in the photoconductive organic semiconductor device.
Background technology
Organic electronic device is with its easily processing, low-cost, sight that high-adaptability has attracted whole world academia and industrial circle, and as the basic element of electronic circuit, the development of organic field effect tube becomes the focus of current research especially.
Nowadays the performance of part organic semiconducting materials has reached the degree that compares favourably with inorganic semiconductor.For example the mobility of rubrene single crystal device has reached 15～40cm
2V
-1s
-1(Zhang, Y.; Hu, W.J.Mater.Chem.2010,20,7029, the mobility of pentacene (PAN) organic film device has also surpassed 5cm
2V-
1s
-1(Kelley, T.W.; Muyres, D.V.; Baude, P.F.; Smith, T.P.; Jones, T.D.Mater.Res.Soc.Symp.Proc.2003,771,169.).But two kinds of materials are compared with inorganic material on cost and stability and are still had gap, have that technology is simple, cost is lower, material property is stable and the long-life will have very wide application prospect with the organic semiconducting materials that reaches the commercialization purpose so design is synthetic.
Thiophene is organic semiconducting materials design and the popular unit that synthesizes with its good conjugate property always, contains thiophene conjugation organic semiconducting materials and has bigger application potential.Therefore, the synthetic bithiophene class organic semiconducting materials of design is studied himself performance and device performance thereof, has than significant values for theoretical research and industrialization.
Summary of the invention
The purpose of this invention is to provide the application of a kind of organic semiconducting materials in the photoconductive organic semiconductor device.
The invention provides the application of compound shown in the formula I in preparation photoconductive organic semiconductor device;
In the formula I, R
1, R
2And R
aIn the described aromatic radical that all is selected from alkyl, aromatic radical and is replaced by described alkyl any, described alkyl is that carbon number is 1～16 straight or branched alkyl, and described aromatic radical is phenyl, fluorenyl, thienyl, contain fluorophenyl, nitrogen heterocycle or siliceous heterocyclic radical;
X, Y all are selected among O, N, S and the Se any;
N is the natural number between 1～7.
In the above-mentioned application, described thienyl can be benzothienyl or dibenzothiophenes base;
Described nitrogen heterocycle can be pyrroles, carbazole, thiazole, thiadiazoles, pyridine or piperidines;
Described siliceous heterocyclic radical can be that thiophene is coughed up or the benzo thiophene is coughed up.
The present invention also provides a kind of photoconductive organic semiconductor device, and it contains compound shown in the formula I; As organic field effect tube, compound can be used for preparing organic semiconductor layer shown in the formula I.
Compound can be prepared according to following method shown in the formula I among the present invention:
(1) acetylide obtains compound shown in the formula IV through acylation reaction shown in glycine compound shown in the formula II and the formula III;
In formula II and the formula IV, R
aIn the described aromatic radical that is selected from alkyl, aromatic radical and is replaced by described alkyl any, described alkyl is that carbon number is 1～16 straight or branched alkyl, and described aromatic radical is phenyl, fluorenyl, thienyl, contain fluorophenyl, nitrogen heterocycle or siliceous heterocyclic radical;
In formula III and the formula IV, R
1In the described aromatic radical that is selected from alkyl, aromatic radical and is replaced by described alkyl any, described alkyl is that carbon number is 1～16 straight or branched alkyl, and described aromatic radical is phenyl, fluorenyl, thienyl, contain fluorophenyl, nitrogen heterocycle or siliceous heterocyclic radical;
(2) compound and P shown in the formula IV
2X
5React and obtain azole compounds shown in the formula V;
P
2X
5In the formula V, X is selected among O, N, S and the Se any; R
aDefinition cotype II;
(3) acetylide obtains compound shown in the formula VII through acylation reaction shown in azole compounds shown in the formula V and the formula VI;
In the formula, R
1And R
aThe definition IV, R
2In the described aromatic radical that is selected from alkyl, aromatic radical and is replaced by described alkyl any, described alkyl is that carbon number is 1～16 straight or branched alkyl, and described aromatic radical is phenyl, fluorenyl, thienyl, contain fluorophenyl, nitrogen heterocycle or siliceous heterocyclic radical;
(4) compound shown in the formula VII is through deamination reaction, and perhaps repeating step (2) and step (3) behind described deamination reaction namely obtain compound shown in the formula VIII;
R in the formula VII
1, R
2And R
aDefinition cotype VII; N is the natural number between 1～7;
(5) compound and P shown in the formula VIII
2Y
5React and obtain compound shown in the formula I;
P
2Y
5In Y be selected among O, N, S and the Se any.
Among the above-mentioned preparation method, in the step (1), the mol ratio of acetylide can be 1:1～1.5 shown in glycine compound shown in the formula II and the formula III, as 1:1.1;
In the step (3), the mol ratio of acetylide can be 1:1～1.5 shown in azole compounds shown in the formula V and the formula VI, as 1:1.1.
Among the above-mentioned preparation method, in the step (2), compound and P shown in the formula IV
2X
5Mol ratio can be 1:1.5～2.5, as 1:1.5;
In the step (5), compound and P shown in the formula VIII
2Y
5Mol ratio can be 1:1.5～2.5, as 1:1.5.
Among the above-mentioned preparation method, reaction described in step (1), step (2), step (3), step (4) and the step (5) all can be carried out under inert atmosphere, as carrying out in nitrogen atmosphere or argon gas atmosphere.
Among the above-mentioned preparation method, in the step (4), described deamination reaction can carry out under the effect of metachloroperbenzoic acid.
Substituted radical shown in the formula I provided by the invention in the compound can be so that the fluorescent emission wavelength of material moves the expanded application scope to ruddiness or blue light direction; For the photoconductive organic semiconductor material provides a kind of new system.With the photoconductive organic semiconductor device of compound provided by the invention preparation highly sensitive, accuracy good, good reproducibility.
Description of drawings
Fig. 1 prepares 1,2,3,4,5, the equation of 6-hexaphenyl two thiophene acenes among the embodiment 1.
Fig. 2 is the structural representation of the organic effect photoelectric device for preparing in the embodiment of the invention.
Fig. 3 is transfer curve and the curve of output of HPDTP thin film field-effect device among the embodiment 2, and wherein, Fig. 3 (A) is transfer curve, and Fig. 3 (B) is curve of output.
Fig. 4 prepares 1,2,3,4-tetraphenyl-5, the equation of 6-dithienyl two thiophene acenes among the embodiment 3.
Fig. 5 is transfer curve and the curve of output of HTDTP single-crystal field effect device among the embodiment 4, and wherein, Fig. 5 (C) is transfer curve, and Fig. 5 (D) is curve of output.
Embodiment
Employed experimental technique is conventional method if no special instructions among the following embodiment.
Used material, reagent etc. if no special instructions, all can obtain from commercial channels among the following embodiment.
Among the following embodiment, source-drain current curve of output (abbreviation curve of output) refers at certain grid voltage V
GDown, source-drain current I
SDWith source-drain voltage V
SDChange curve;
Source-drain current transfer curve (abbreviation transfer curve) refers at certain source-drain voltage V
SDDown, source-drain current I
SDWith grid voltage V
GChange curve;
Wherein, when the transfer curve of mensuration organic field effect tube and curve of output, the temperature range of mensuration is 293～450K.
Reaction equation as shown in Figure 1.
(1) 1-methyl-2,5-diphenyl-3,4-benzophenone base pyrroles's (formula 1) is synthetic
In two mouthfuls of flasks of 150mL, vacuumize logical argon gas.Add glacial acetic acid 80mLN-methyl-N-benzoyl phenylglycine 2.69g(10mmol then successively), drip 1,2-dibenzoyl acetylene 2.60g(11mmol behind the stirring at normal temperature 30min), being warming up to refluxes stirs 5h, cessation reaction.Water, saturated sodium bicarbonate solution are washed successively, filter sepia product 3.65g(productive rate 82.7%), i.e. compound shown in the formula 1.
(2) N-methyl-2,5-diphenyl-3,4-diphenyl thiophene and pyrroles's (formula 2) is synthetic
In two mouthfuls of flasks of 250mL, vacuumize logical argon gas.Add benzene 120mL1-methyl-2 then successively, 5-diphenyl-3,4-benzophenone base pyrroles 4.41g (10mmol) is warming up to 60 ℃, stirs to add P
2S
58.88g(40mmol), continue to stir 12h, cessation reaction.Benzene is removed in decompression distillation, and water, dilute hydrochloric acid solution are washed successively, and decompression is spin-dried for, and crosses chromatographic column (PE:CH
2C
2=3:1) yellowish-brown product 3.12g(productive rate 70.7%), i.e. compound shown in the formula 2.
(3) 8-methyl isophthalic acid, 3,4,7-tetraphenyl-4,7-epimino-benzothiophene-5,6 benzophenone (formula 3) synthetic
Identical in course of reaction and the step (1), obtain compound shown in the formula 3, productive rate is 61%.
(4) 1,3,4,7-tetraphenyl benzothiophene-5,6-benzophenone (formula 4) synthetic
In the 150mL there-necked flask, vacuumize logical argon gas.Add toluene 100mL then successively, compound 2.45g shown in the formula 3 (4mmol) is warming up to 60 ℃, stirs to add metachloroperbenzoic acid 3.44g(20mmol), continue to stir 12h, cessation reaction.Toluene is removed in decompression distillation, and water, solution of sodium bisulfite are washed successively, and decompression is spin-dried for, and crosses chromatographic column (PE:CH
2C
2=2:1) yellow product 3.12g(productive rate 62%), i.e. compound shown in the formula 4.
(5) compound 1,2,3,4,5,6-hexaphenyl two thiophene acenes (formula I-1) synthetic
Course of reaction is identical with step (2), gets the crocus solid, i.e. compound shown in the formula I-1, productive rate 48%.
The structural confirmation data of this product are as follows:
Mass spectrum: MALDI-TOF:m/z:646.85;
Nucleus magnetic hydrogen spectrum:
1H NMR (400MHz, CDCl
3) δ (ppm): 7.16 (d, 4H), 7.41-7.45 (t, 10H), 7.48-7.51 (t, 8H), 7.68 (d, 8H).
Nuclear-magnetism carbon spectrum:
13C NMR (101MHz, CDCl
3) δ (ppm): 180.23 (s), 141.82 (s), 139.07 (s), 135.64 (m), 129.94 (s), 128.43 – 128.64 (m), 127.9 (s).
By above-mentioned test data as can be known, this compound structure is correct, is compound shown in the formula I-1: 1,2,3,4,5,6-hexaphenyl, two thiophene acenes.
(1) preparation semiconductor device
Silicon chip cleans: the silicon chip that will have the silicon dioxide inorganic insulation layer is cut into the small pieces of suitable size, be put in the beaker, the hydrogen peroxide and the concentrated sulfuric acid mixed solvent that add about 3:7 proportional arrangement, utilize the electric furnace heating to boil about 40 minutes, outwell the solvent acid solution, rinse out the remaining concentrated sulfuric acid and hydrogen peroxide with deionized water, use ultrasonic about 10 minutes of deionized water, isopropyl alcohol then respectively, utilize nitrogen to dry up fast at last.
Device preparation: by the vacuum thermal evaporation method HPDTP is deposited on the silicon chip of band 300nm silicon dioxide and prepares organic semiconductor layer, evaporation rate was 0.4 dust/second, and vacuum degree is 6 * 10 during evaporation
-4Pascal, the thickness of organic semiconductor layer is about 50nm.Source, drain electrode material are Au, and by the preparation of vacuum mask vapour deposition method, thickness is about 20nm, and the device preparation finishes.
The structural representation of this device model as shown in Figure 2.Wherein, 1 for having the gate electrode of inorganic insulation layer, and 2 is the organic semiconductor thin-film layer, and 3 is the source electrode, and 4 is drain electrode.
(2) thin film field-effect device performance test
The semiconductor device that step (1) is obtained is placed on and is equipped with on the Keithley4200 micro operation probe platform, tests transfer curve and curve of output respectively, the result as shown in Figure 3, calculating its hole mobility is 0.73cm
2/ (Vs), on-off ratio 10
5, can learn that thus compound provided by the invention has preferably near the performance of amorphous silicon, has the industry using value.
Reaction equation as shown in Figure 4.
(1) 1-methyl-2,5-diphenyl-3,4-two thiophene ketone base pyrroles' (formula 1 ') is synthetic
In two mouthfuls of flasks of 150mL, vacuumize logical argon gas.Add glacial acetic acid 80mL then successively, the N-methyl, N-benzoyl phenylglycine 2.69g (10mmol) drips 1,2-, two thenoyl acetylene 2.64g(11mmol behind the stirring at normal temperature 30min), being warming up to refluxes stirs 5h, cessation reaction.Water, saturated sodium bicarbonate solution are washed successively, filter sepia product 3.85g(productive rate 84.7%), i.e. compound shown in the formula .1 '.
(2) N-methyl-2,5-diphenyl-3,4-dithienyl Thienopyrroles (formula 2 ') synthetic
In two mouthfuls of flasks of 250mL, vacuumize logical argon gas.Add benzene 120mL then successively, 1-methyl-2,5-diphenyl-3,4-two thiophene ketone base pyrroles 4.51g (10mmol) are warming up to 60 ℃, stir to add P
2S
58.88g(40mmol), continue to stir 12h, cessation reaction.Benzene is removed in decompression distillation, and water, dilute hydrochloric acid solution are washed successively, and decompression is spin-dried for, and crosses chromatographic column (PE:CH
2C
2=3:1) yellowish-brown product 3.42g(productive rate 71.7%), i.e. compound shown in the formula 2 '.
(3) 8-methyl isophthalic acid, 3-dithienyl-4,7-diphenyl-4,7-epimino-benzothiophene-5,6 benzophenone (formula 3 ') synthetic
Course of reaction is identical with step (1), obtains compound shown in the formula 3 ', and productive rate is 60%.
(4) 1,3-dithienyls-4,7-diphenyl benzene bithiophene-5,6-benzophenone (formula 4 ') synthetic
In the 150mL there-necked flask, vacuumize logical argon gas.Add toluene 100mL then successively, the 2.55g of compound shown in the formula 3 ' (4mmol) is warming up to 60 ℃, stirs to add metachloroperbenzoic acid 3.44g(20mmol), continue to stir 12h, cessation reaction.Toluene is removed in decompression distillation, and water, solution of sodium bisulfite are washed successively, and decompression is spin-dried for, and crosses chromatographic column (PE:CH
2C
2=2:1) yellow product 3.22g(productive rate 62%), i.e. compound shown in the formula 4 '.
(5) compound 1,2,3,4-tetraphenyl-5,6-dithienyl two thiophene acenes (formula I-2) synthetic
Course of reaction is identical with step (2), gets the crocus solid, i.e. compound shown in the formula I-2, productive rate 45%.
The structural confirmation data of this product are as follows:
Mass spectrum: MALDI-TOF:m/z:658.92;
Nucleus magnetic hydrogen spectrum:
1H NMR (400MHz, CDCl
3) δ (ppm): 7.16 (d, 6H), 7.34 (d, 4H), 7.41-7.45 (t, 8H), 7.51 (t, 4H), 7.69 (d, 2H), 7.73 (d, 2H).
Nuclear-magnetism carbon spectrum:
13C NMR (101MHz, CDCl
3) δ (ppm): 228.4.23 (s), 147.6 (s), 142.3 (s), 136.9 (s), 135.64 (m), 129.94 (s), 127.8.43 – 128.64 (m), 123.6 (s).
As from the foregoing, this compound structure is correct, is compound shown in the formula I-2: 1,2,3,4-tetraphenyl-5,6-dithienyl two thiophene acenes.
(1) preparation semiconductor device
Silicon chip cleans and adopts with method identical among the embodiment 2.
The device preparation: by the vacuum thermal evaporation method HTDTP is deposited on the silicon chip of band 300nm silicon dioxide, vacuum degree is 6～8 * 10 during evaporation
-4Pascal, the thickness of organic semiconductor layer is about 50nm, wherein evaporation rate be 0.1 dust/second to 10 nanometers, 0.2 dust/second, 0.3 dust/second was to 50 nanometers to 20 nanometers.Source, drain electrode material are Au, and by the preparation of vacuum mask vapour deposition method, thickness is about 20nm, and the device preparation finishes.
(2) thin film field-effect device performance test
The semiconductor device that step (1) is obtained is placed on and is equipped with on the Keithley4200 micro operation probe platform, tests transfer curve and curve of output respectively.The result as shown in Figure 5, calculating its hole mobility is 1.73cm
2/ (Vs), on-off ratio 10
7, can learn that thus compound provided by the invention has the performance that reaches amorphous silicon preferably, have the industry using value.
The description of above-described embodiment is that the person skilled in art can understand and apply the invention for convenience.Those of ordinary skill in the art obviously are easy to these embodiment are made modification, and needn't pass through performing creative labour being applied at the General Principle of this invention and reaction scheme among other embodiment.Therefore, the invention is not restricted to listed examples here, those skilled in the art is according to announcement of the present invention, the improvement that this invention is made and revising all within protection scope of the present invention.
Claims (5)
1. the application of compound shown in the formula I in preparation photoconductive organic semiconductor device;
In the formula I, R
1, R
2And R
aIn the described aromatic radical that all is selected from alkyl, aromatic radical and is replaced by described alkyl any, described alkyl is that carbon number is 1～16 straight or branched alkyl, and described aromatic radical is phenyl, fluorenyl, thienyl, contain fluorophenyl, nitrogen heterocycle or siliceous heterocyclic radical;
X, Y all are selected among O, N, S and the Se any;
N is the natural number between 1～7.
2. application according to claim 1 is characterized in that: described thienyl is benzothienyl or dibenzothiophenes base;
Described nitrogen heterocycle is pyrroles, carbazole, thiazole, thiadiazoles, pyridine or piperidines;
Described siliceous heterocyclic radical is that thiophene is coughed up or the benzo thiophene is coughed up.
3. photoconductive organic semiconductor device, it is characterized in that: it contains compound shown in the formula I.
4. photoelectric device according to claim 3, it is characterized in that: described photoconductive organic semiconductor device is organic field effect tube.
5. photoelectric device according to claim 4, it is characterized in that: the organic semiconductor layer of described organic field effect tube is compound shown in the formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310179683.7A CN103247759B (en) | 2013-05-15 | 2013-05-15 | Organic semiconducting materials application in photoconductive organic semiconductor device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310179683.7A CN103247759B (en) | 2013-05-15 | 2013-05-15 | Organic semiconducting materials application in photoconductive organic semiconductor device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103247759A true CN103247759A (en) | 2013-08-14 |
| CN103247759B CN103247759B (en) | 2016-08-10 |
Family
ID=48927109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310179683.7A Active CN103247759B (en) | 2013-05-15 | 2013-05-15 | Organic semiconducting materials application in photoconductive organic semiconductor device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103247759B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435784A (en) * | 2013-08-16 | 2013-12-11 | 南京友斯贝特光电材料有限公司 | Benzodithiophene-like polymer as well as preparation method and application thereof |
| CN103450462A (en) * | 2013-08-19 | 2013-12-18 | 南京友斯贝特光电材料有限公司 | D-A type polymer semiconductor material, and preparation method and application thereof |
| CN103483557A (en) * | 2013-08-16 | 2014-01-01 | 南京友斯贝特光电材料有限公司 | Dithienobenzene polymers, and preparation method and application thereof |
| CN105845618A (en) * | 2015-01-13 | 2016-08-10 | 中芯国际集成电路制造(上海)有限公司 | Method for preventing copper oxidation diffusion |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60254037A (en) * | 1984-05-30 | 1985-12-14 | Ricoh Co Ltd | Optical information recording medium |
-
2013
- 2013-05-15 CN CN201310179683.7A patent/CN103247759B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60254037A (en) * | 1984-05-30 | 1985-12-14 | Ricoh Co Ltd | Optical information recording medium |
Non-Patent Citations (1)
| Title |
|---|
| JUERGEN FABIAN: "TDDFT-calculations of Vis/NIR absorbing compounds", 《DYES AND PIGMENTS》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435784A (en) * | 2013-08-16 | 2013-12-11 | 南京友斯贝特光电材料有限公司 | Benzodithiophene-like polymer as well as preparation method and application thereof |
| CN103483557A (en) * | 2013-08-16 | 2014-01-01 | 南京友斯贝特光电材料有限公司 | Dithienobenzene polymers, and preparation method and application thereof |
| CN103483557B (en) * | 2013-08-16 | 2017-03-01 | 南京友斯贝特光电材料有限公司 | A kind of dithieno benzene polymer and its preparation method and application |
| CN103450462A (en) * | 2013-08-19 | 2013-12-18 | 南京友斯贝特光电材料有限公司 | D-A type polymer semiconductor material, and preparation method and application thereof |
| CN103450462B (en) * | 2013-08-19 | 2016-03-02 | 南京友斯贝特光电材料有限公司 | D-A type polymer semiconductor material and preparation method thereof and application |
| CN105845618A (en) * | 2015-01-13 | 2016-08-10 | 中芯国际集成电路制造(上海)有限公司 | Method for preventing copper oxidation diffusion |
| CN105845618B (en) * | 2015-01-13 | 2019-07-19 | 中芯国际集成电路制造(上海)有限公司 | A method of preventing copper oxidized diffusion |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103247759B (en) | 2016-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Xiong et al. | Ultrahigh responsivity photodetectors of 2D covalent organic frameworks integrated on graphene | |
| Shang et al. | A solution‐processable star‐shaped molecule for high‐performance organic solar cells | |
| Rudebusch et al. | Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials | |
| Li et al. | Stable solution-processed high-mobility substituted pentacene semiconductors | |
| Tang et al. | High-performance organic semiconductors: asymmetric linear acenes containing sulphur | |
| KR102507357B1 (en) | Strongly Polarized Molecules, and Single Molecule Field Effect Transistors Made Therefrom | |
| Hoang et al. | Unusually High‐Performing Organic Field‐Effect Transistors Based on π‐Extended Semiconducting Porphyrins | |
| Kim et al. | Highly sensitive phototransistor with crystalline microribbons from new π-extended pyrene derivative via solution-phase self-assembly | |
| TW200904821A (en) | Silylethynylated heteroacenes and electronic devices made therewith | |
| Akin et al. | Cyclopentadithiophene-based hole-transporting material for highly stable perovskite solar cells with stabilized efficiencies approaching 21% | |
| CN103247759A (en) | Application of organic semiconductor material to organic semiconductor photoelectric device | |
| Wilbuer et al. | Donor-and acceptor-functionalized dibenzo [a, e] pentalenes: modulation of the electronic band gap | |
| Geib et al. | Core‐Brominated Tetraazaperopyrenes as n‐Channel Semiconductors for Organic Complementary Circuits on Flexible Substrates | |
| Youn et al. | Fused Thiophene Semiconductors: Crystal Structure–Film Microstructure Transistor Performance Correlations | |
| CN105315273A (en) | Polyceptor-structure small molecule compound and preparing method and application thereof | |
| CN103242343B (en) | A kind of Organic micromolecular semiconductor material and preparation method thereof | |
| Gui et al. | A flexible n-type organic semiconductor for optoelectronics | |
| Ren et al. | Dithienoindophenines: p‐Type Semiconductors Designed by Quinoid Stabilization for Solar‐Cell Applications | |
| Liu et al. | The relationship between intermolecular interactions and charge transport properties of trifluoromethylated polycyclic aromatic hydrocarbons | |
| Kwon et al. | Naphtho [2, 3, a] pyrene as an efficient multifunctional organic semiconductor for organic solar cells, organic light-emitting diodes, and organic thin-film transistors | |
| Kwon et al. | 4, 4′, 4 ″-Tris (4-naphthalen-1-yl-phenyl) amine as a multifunctional material for organic light-emitting diodes, organic solar cells, and organic thin-film transistors | |
| Seo et al. | The effect of processing additive on aggregated fullerene derivatives in bulk-heterojunction polymer solar cells | |
| Moggia et al. | Synthesis and thin film electronic properties of two pyrene-substituted oligothiophene derivatives | |
| Liu et al. | Oligothiophene‐Bridged Bis (arylene ethynylene) Small Molecules for Solution‐Processible Organic Solar Cells with High Open‐Circuit Voltage | |
| CN105820316B (en) | Hetero atom replaces naphthalimide polymer semiconductor and the preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20200520 Address after: 1812, block a, building 5, Qidi Xiexin, No. 333, Longfei Avenue, huanggekeng community, Longcheng street, Longgang District, Shenzhen City, Guangdong Province Patentee after: SHENZHEN LEPUTAI TECHNOLOGY Co.,Ltd. Address before: 100872 1207E building, building 59, Zhongguancun street, Haidian District, Beijing Patentee before: BROAD (BEIJING) ORGANIC OPTOELECTRONIC MATERIALS RESEARCH & ENGINEERING Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 518000 room 1812, block a, building 5, edixie Xin, No. 333, Longfei Avenue, huanggekeng community, Longcheng street, Longgang District, Shenzhen City, Guangdong Province Patentee after: Shenzhen Luxiang Technology Co.,Ltd. Address before: 518000 room 1812, block a, building 5, edixie Xin, No. 333, Longfei Avenue, huanggekeng community, Longcheng street, Longgang District, Shenzhen City, Guangdong Province Patentee before: SHENZHEN LEPUTAI TECHNOLOGY Co.,Ltd. |
|
| CP01 | Change in the name or title of a patent holder | ||
| CP03 | Change of name, title or address |
Address after: 518000 1903, Building B, Smart Home, No. 76, Baohe Avenue, Baolong Community, Baolong Street, Longgang District, Shenzhen, Guangdong Province Patentee after: SHENZHEN LEPUTAI TECHNOLOGY Co.,Ltd. Address before: 518000 room 1812, block a, building 5, edixie Xin, No. 333, Longfei Avenue, huanggekeng community, Longcheng street, Longgang District, Shenzhen City, Guangdong Province Patentee before: Shenzhen Luxiang Technology Co.,Ltd. |
|
| CP03 | Change of name, title or address |