CN113583507A - Organic semiconductor ink, preparation method and application - Google Patents
Organic semiconductor ink, preparation method and application Download PDFInfo
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- CN113583507A CN113583507A CN202110724926.5A CN202110724926A CN113583507A CN 113583507 A CN113583507 A CN 113583507A CN 202110724926 A CN202110724926 A CN 202110724926A CN 113583507 A CN113583507 A CN 113583507A
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 36
- 230000000996 additive effect Effects 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000007641 inkjet printing Methods 0.000 claims abstract description 5
- -1 2-octyldodecyl Chemical group 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- 125000005605 benzo group Chemical group 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 claims description 5
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- KZDTZHQLABJVLE-UHFFFAOYSA-N 1,8-diiodooctane Chemical compound ICCCCCCCCI KZDTZHQLABJVLE-UHFFFAOYSA-N 0.000 claims description 3
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000007645 offset printing Methods 0.000 claims description 2
- 238000007650 screen-printing Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 238000010023 transfer printing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 8
- 238000007639 printing Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 230000002411 adverse Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 239000010408 film Substances 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005297 material degradation process Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Thin Film Transistor (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to the technical field of organic semiconductor ink, in particular to organic semiconductor ink, a preparation method and application thereof. Compared with the prior art, the semiconductor organic ink provided by the invention has a wide application range, so that an organic semiconductor electronic product has a wider application range, the molecular additive can replace water to fill gaps of a film structure, and adverse effects of water are reduced, so that the stability and uniformity of an organic film are improved, the appearance of a disordered organic semiconductor film can be adjusted through a solution additive, the film structure can be densified, the size of the gaps of the structure is reduced, the stability of a device is improved, the normal printing requirement of an ink-jet printer is met, and the semiconductor organic ink is suitable for high-precision ink-jet printing required by printing electronics; the method has simple process, saves additional post-treatment process, and obtains the organic semiconductor film with excellent environmental tolerance.
Description
Technical Field
The invention relates to the technical field of organic semiconductor ink, in particular to organic semiconductor ink, a preparation method and application.
Background
The advent of digital printing technology has led to the rapid development of inkjet printing in non-impact printing, and its application fields are expanding. Meanwhile, the development of printed electronic materials and technologies also provides opportunities for the combination of printed circuit board preparation, flexible display electrodes, electromagnetic shielding materials and printing technologies.
As part of an emerging and developing electronics industry, organic semiconductor circuits are typically studied through the process of: firstly, the newly synthesized organic semiconductor material is applied to a functional device, a thin film deposition process and a liquid phase process are continuously optimized, a device structure and a process method which are optimal for the material are found, the material characteristics are checked through the device performance, and the material performance is improved by one step. Early improvements in device performance focused on the mobility of organic semiconductor materials, and since 2002, important effects of other factors on device performance were gradually recognized, and more attention was paid to high mobility and performance stability.
The disordered organic semiconductor film prepared by the solution treatment method has performance reduction in the atmospheric environment, wherein trace water permeating in gaps of a film structure can provide stabilizing effect of electrons and hole polarons to cause reduction of mobility, and the combination of oxygen and water can cause degradation of organic materials. Research has shown that water incorporation in nanoscale voids within polymer microstructures is a critical factor in charge trapping and device degradation, and that experimentally, molecular configuration in small voids is difficult to detect because of the low relative concentrations of water involved, while water is ubiquitous in most experiments. Therefore, finding an organic semiconductor ink with higher stability and lifetime has great scientific impact and practical significance.
Disclosure of Invention
In view of the above-mentioned drawbacks of the background art, the present invention provides an organic semiconductor ink, a method for preparing the same, and applications of the same.
The technical scheme adopted by the invention is as follows: the key point of the semiconductor organic ink is that the semiconductor organic ink comprises the following components in parts by mass: 5-15 parts of organic semiconductor material, 80-90 parts of organic solvent, 0.5-15 parts of molecular additive and 0.5-12 parts of solvent additive;
the semiconductor material is poly { N, N ' -bis (2-octyldodecyl) benzo LMN3,8 o-phenanthroline-1, 3,6,8(2H,7H) -tetrone-4, 9-diyl) (2,2 ' dithienyl-5, 5 ' -diyl) }, indedithiophene-copolybenzothiadiazole, poly (3-hexylthiophene-2, 5-diyl), poly [2, 3-bis (3-octyloxyphenyl) -5, 8-quinoxalinediyl ] -2, 5-thiophenediyl ], poly [2,6- (4, 4-bis- (2-ethylhexyl) -4H-cyclopentadiene [2, 1-b; 3,4-b '] dithiophene) -alt-4,7(2,1, 3-benzothiadiazole) ], poly ({4, 8-bis [ (2-ethylhexyl) oxy ] benzo [1,2-b:4,5-b' ] dithiophene-2, 6-diyl } { 3-fluoro-2- [ (2-ethylhexyl) carbonyl ] thieno [3,4-b ] thiophenediyl }).
Preferably, the organic semiconductor material has a weight average molecular weight Mw < 10000.
Preferably, the number average molecular weight Mn of the organic semiconductor material is < 50000.
Preferably, the molecular additive is 7,7,8, 8-tetracyanoquinolinemethane.
Preferably, the solution additive is one or more of 1, 8-octanedithiol, 1, 8-diiodooctane, 1-chloronaphthalene and diphenyl ether.
Preferably, the mass ratio of the molecular additive to the organic semiconductor material is 5-15: 100.
preferably, the volume ratio of the solution additive to the organic solvent is 1-10: 100.
the preparation method of the semiconductor organic ink is characterized in that: dissolving an organic semiconductor material in an organic solvent under an inert atmosphere, adding a molecular additive, heating and stirring for 8-12h, then cooling to room temperature, adding the solvent additive, and stirring for 2-5h to obtain the semiconductor organic ink.
The application of the semiconductor organic ink is characterized in that: for the preparation of organic semiconductor layers.
The application of the semiconductor organic ink is characterized in that: for slot coating, spin coating, ink jet printing, transfer printing, offset printing or screen printing.
Has the advantages that: compared with the prior art, the semiconductor organic ink provided by the invention has a wide application range, so that organic semiconductor electronic products have a wider application range, and comprises an OLED display, a photoelectric sensor and an FET sensor which is sensitive to analytes only and is not sensitive to solution change, water can be replaced by a molecular additive to fill gaps of a film structure, and adverse effects of the water are reduced, so that the stability and uniformity of the organic film are improved, the appearance of the disordered organic semiconductor film can be adjusted by the solution additive, the film structure is favorably densified, so that the size of the gaps of the structure is reduced, the stability of devices is improved, the normal printing requirement of an ink-jet printer is met, and the semiconductor organic ink is suitable for high-precision ink-jet printing required by printing electronics; the method has simple process, saves additional post-treatment process, and obtains the organic semiconductor film with excellent environmental tolerance.
Drawings
FIG. 1 is a TEM image of a film formed by the organic semiconductor ink of the present invention;
FIG. 2 is a graph of hole mobility of a thin film as a function of time.
Detailed Description
In order to make the technical solutions of the present invention better understood, the present invention will be described in detail below with reference to the accompanying drawings and specific embodiments. The experimental procedures described in the following examples are conventional unless otherwise specified, and the reagents and materials, if not specified, are commercially available.
Example 1
Under inert atmosphere, 10 parts of N-type organic semiconductor { N, N ' -bis (2-octyldodecyl) benzo LMN3, 8-phenanthroline-1, 3,6,8(2H,7H) -tetraone-4, 9-diyl) (2,2 ' dithienyl-5, 5 ' -diyl) } with the average molecular weight of 50000 are dissolved in 100 parts of anhydrous chlorobenzene, 5 parts of molecular additive 7,7,8, 8-tetracyanoquinolinemethane is added, 1 part of solution additive 1, 8-octanedithiol is added after stirring at a constant temperature of 50 ℃ for 10 hours at 500rpm, and the organic semiconductor ink is obtained after stirring at a constant temperature of 25 ℃ for 3 hours at 500 rpm.
Example 2
Under an inert atmosphere, 8 parts of p-type organic semiconductor poly ({4, 8-bis [ (2-ethylhexyl) oxy ] benzo [1,2-b:4,5-b' ] dithiophene-2, 6-diyl } { 3-fluoro-2- [ (2-ethylhexyl) carbonyl ] thieno [3,4-b ] thiophenediyl }) with the average molecular weight of 50000 are dissolved in 100 parts of anhydrous chlorobenzene, 5 parts of molecular additive 7,7,8, 8-tetracyanoquinolinemethane is added, 1 part of solution additive 1, 8-diiodooctane is added after stirring at a constant temperature of 50 ℃ for 10 hours at 500rpm, and the organic semiconductor ink is obtained after stirring at a constant temperature of 25 ℃ for 3 hours at 500 rpm.
Example 3
Under inert atmosphere, 1 part of indene dithiophene-copolybenzothiadiazole with the average molecular weight of 40000 and poly (3-hexylthiophene-2, 5-diyl) are dissolved in 80 parts of anhydrous chlorobenzene, 0.1 part of molecular additive 7,7,8, 8-tetracyanoquinoline methane is added, 2 parts of solution additive 1-chloronaphthalene is added after stirring for 8 hours at the constant temperature of 50 ℃ and the rotating speed of 500rpm, and stirring for 2 hours at the constant temperature of 25 ℃ and the rotating speed of 500rpm to obtain the organic semiconductor ink.
Example 4
Under inert atmosphere, 20 parts of poly [2,6- (4, 4-bis- (2-ethylhexyl) -4H-cyclopentadiene [2, 1-b; 3,4-b' ] dithiophene) -alt-4,7(2,1, 3-benzothiadiazole) ] with the average molecular weight of 30000 are dissolved in 90 parts of anhydrous chlorobenzene, 20 parts of molecular additive 7,7,8, 8-tetracyanoquinoline methane is added, stirring is carried out at constant temperature of 50 ℃ for 12 hours by 500rpm, 12 parts of solution additive diphenyl ether is added, and stirring is carried out at constant temperature of 25 ℃ for 5 hours by 500rpm, thus obtaining the organic semiconductor ink.
Example 5
Under inert atmosphere, 18 parts of poly [2, 3-bis (3-octyloxyphenyl) -5, 8-quinoxalinediyl ] -2, 5-thiophenediyl ] with the average molecular weight of 50000 are dissolved in 100 parts of anhydrous chlorobenzene, 15 parts of molecular additive 7,7,8, 8-tetracyanoquinolinemethane are added, after stirring is carried out at constant temperature of 50 ℃ for 12 hours at 500rpm, 8 parts of solution additive 1, 8-octanedithiol are added, and stirring is carried out at constant temperature of 25 ℃ for 5 hours at 500rpm, thus obtaining the organic semiconductor ink.
Example 6
Under inert atmosphere, 6 parts of poly [2, 3-bis (3-octyloxyphenyl) -5, 8-quinoxalindinyl ] -2, 5-thiophenediyl ] with the average molecular weight of 40000 are dissolved in 100 parts of anhydrous chlorobenzene, 8 parts of molecular additive 7,7,8, 8-tetracyanoquinolinemethane is added, after stirring is carried out at constant temperature of 50 ℃ for 12 hours by 500rpm, 5 parts of solution additive 1-chloronaphthalene is added, and stirring is carried out at constant temperature of 25 ℃ for 5 hours by 500rpm, thus obtaining the organic semiconductor ink.
Example 7
Under inert atmosphere, 3 parts of indene dithiophene-copolybenzothiadiazole with the average molecular weight of 30000 are dissolved in 100 parts of anhydrous chlorobenzene, 4 parts of molecular additive 7,7,8, 8-tetracyanoquinoline methane are added, after stirring is carried out at constant temperature of 50 ℃ for 12 hours at 500rpm, 4 parts of solution additive 1-chloronaphthalene is added, and stirring is carried out at constant temperature of 25 ℃ for 5 hours at 500rpm, thus obtaining the organic semiconductor ink.
Example 8
Under inert atmosphere, 14 parts of indene bithiophene-copolymerization benzothiadiazole with the average molecular weight of 40000 are dissolved in 100 parts of anhydrous chlorobenzene, 10 parts of molecular additive 7,7,8, 8-tetracyanoquinoline methane is added, after stirring is carried out at constant temperature of 50 ℃ for 12 hours at 500rpm, 10 parts of solution additive 1, 8-octanedithiol is added, and stirring is carried out at constant temperature of 25 ℃ for 5 hours at 500rpm, so that the organic semiconductor ink can be obtained.
Taking example 1 as an example, the invention was tested for performance:
and (3) testing by a scanning electron microscope: a small amount of the organic semiconductor ink was applied to form a thin film, which was observed using a Transmission Electron Microscope (TEM), as shown in fig. 1; the uniform distribution of the polymer in the organic semiconducting ink can be seen in fig. 1.
And (3) testing electrical properties: the organic semiconductor ink was printed as a pre-fabricated device on paper by an inkjet printer and tested for mobility for different periods of exposure to atmospheric conditions using a keithley 2400 digital source meter, as shown in fig. 2; the mobility reduction of one order of magnitude after a duration of about 17 hours is shown in fig. 2, indicating that the device made with the ink of the present invention has greater stability against material degradation from the effects of water and oxygen in a scenario of complete exposure to air.
Finally, it should be noted that the above-mentioned description is only a preferred embodiment of the present invention, and those skilled in the art can make various similar representations without departing from the spirit and scope of the present invention.
Claims (10)
1. The semiconductor organic ink is characterized by comprising the following components in parts by mass: 1-20 parts of organic semiconductor material, 80-100 parts of organic solvent, 0.1-20 parts of molecular additive and 0.5-12 parts of solvent additive;
the semiconductor material is poly { N, N ' -bis (2-octyldodecyl) benzo LMN3,8 o-phenanthroline-1, 3,6,8(2H,7H) -tetrone-4, 9-diyl) (2,2 ' dithienyl-5, 5 ' -diyl) }, indedithiophene-copolybenzothiadiazole, poly (3-hexylthiophene-2, 5-diyl), poly [2, 3-bis (3-octyloxyphenyl) -5, 8-quinoxalinediyl ] -2, 5-thiophenediyl ], poly [2,6- (4, 4-bis- (2-ethylhexyl) -4H-cyclopentadiene [2, 1-b; 3,4-b '] dithiophene) -alt-4,7(2,1, 3-benzothiadiazole) ], poly ({4, 8-bis [ (2-ethylhexyl) oxy ] benzo [1,2-b:4,5-b' ] dithiophene-2, 6-diyl } { 3-fluoro-2- [ (2-ethylhexyl) carbonyl ] thieno [3,4-b ] thiophenediyl }).
2. A semiconducting organic ink according to claim 1, wherein: the weight average molecular weight Mw of the organic semiconductor material is less than 10000.
3. A semiconducting organic ink according to claim 1, wherein: the number average molecular weight Mn of the organic semiconductor material is less than or equal to 50000.
4. A semiconducting organic ink according to claim 1, wherein: the molecular additive is 7,7,8, 8-tetracyanoquinoline methane.
5. A semiconducting organic ink according to claim 1, wherein: the solution additive is one or more of 1, 8-octanedithiol, 1, 8-diiodooctane, 1-chloronaphthalene and diphenyl ether.
6. A semiconducting organic ink according to claim 1, wherein: the mass ratio of the molecular additive to the organic semiconductor material is 5-15: 100.
7. a semiconducting organic ink according to claim 1, wherein: the volume ratio of the solution additive to the organic solvent is 1-10: 100.
8. a method of preparing a semiconducting organic ink according to any of claims 1 to 7, wherein: dissolving an organic semiconductor material in an organic solvent under an inert atmosphere, adding a molecular additive, heating and stirring for 8-12h, then cooling to room temperature, adding the solvent additive, and stirring for 2-5h to obtain the semiconductor organic ink.
9. Use of a semiconducting organic ink according to claim 1, wherein: for the preparation of organic semiconductor layers.
10. Use of a semiconducting organic ink according to claim 1, wherein: for slot coating, spin coating, ink jet printing, transfer printing, offset printing or screen printing.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101195720A (en) * | 2006-12-08 | 2008-06-11 | 有机光电公司 | Organic electroluminescent materials, apparatus, systems, and methods |
| CN102164926A (en) * | 2008-09-29 | 2011-08-24 | 加利福尼亚大学董事会 | Active materials for photoelectric devices |
| CN102668151A (en) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | Compositions comprising organic semiconducting compounds |
| CN106463408A (en) * | 2014-05-09 | 2017-02-22 | 日本曹达株式会社 | Organic semiconductor element |
| CN112876382A (en) * | 2019-11-29 | 2021-06-01 | 广州华睿光电材料有限公司 | Organic compounds, mixtures, compositions and uses thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101195720A (en) * | 2006-12-08 | 2008-06-11 | 有机光电公司 | Organic electroluminescent materials, apparatus, systems, and methods |
| CN102164926A (en) * | 2008-09-29 | 2011-08-24 | 加利福尼亚大学董事会 | Active materials for photoelectric devices |
| CN102668151A (en) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | Compositions comprising organic semiconducting compounds |
| CN106463408A (en) * | 2014-05-09 | 2017-02-22 | 日本曹达株式会社 | Organic semiconductor element |
| CN112876382A (en) * | 2019-11-29 | 2021-06-01 | 广州华睿光电材料有限公司 | Organic compounds, mixtures, compositions and uses thereof |
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