CN100465178C - Quadribasic phthalocyanine copper film with controllably doped tetrachlorobenzoquinone/triphenyl phosphorus and its prepn process - Google Patents
Quadribasic phthalocyanine copper film with controllably doped tetrachlorobenzoquinone/triphenyl phosphorus and its prepn process Download PDFInfo
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- CN100465178C CN100465178C CNB2004100845752A CN200410084575A CN100465178C CN 100465178 C CN100465178 C CN 100465178C CN B2004100845752 A CNB2004100845752 A CN B2004100845752A CN 200410084575 A CN200410084575 A CN 200410084575A CN 100465178 C CN100465178 C CN 100465178C
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Abstract
The present invention belongs to the field of organic semiconductor material technology, and is especially quadribasic phthalocyanine copper film with controllably doped tetrachlorobenzoquinone/triphenyl phosphorus and its preparation process. The film is prepared through electrochemical deposition process with doped quadribasic phthalocyanine copper solution, which is compounded via homogeneously dispersing tetrachlorobenzene ester and/or triphenyl phosphide, quadribasic phthalocyanine and electrolyte in certain proportion in organic solvent. The doping degree of the film may be controlled through regulating dopant type, dopant concentration, voltage of power supply and current. The present invention has simple technological process, high efficiency, low cost, good filming performance and high heat stability, and may be used in the preparation of various photoelectronic materials.
Description
Technical field
The invention belongs to the organic semiconductor material technical field, be specifically related to controllable doped four substituted phthalocyanine copper films of a kind of tetrachlorobenzoquinone and/or triphenyl phosphorus and preparation method thereof.
Background technology
Since the eighties, phthalocyanine-like compound is as the novel organic photoelectrical material of a class, because of its excellent photoelectric property, to the stability of light and heat and the controllability of molecular structure, be subjected to domestic and international researchist's very big concern, be widely used in photoelectric device research fields such as light regulation and control device, optical storage, infrared eye, transmitter, Laser Printing and barrier-layer cell.But this class material purifying difficulty, film forming properties is poor, and the photoelectric transformation efficiency of phthalocyanine material is lower, has limited its further application in photoelectric device.
Doping is a kind of effective means of the efficient and practicability of phthalocyanines organic semiconductor material and device thereof, as AppliedPhysics Letters, and V73 (6), p729,1998 employing F
4-TCNQ doping the ranadylic phthalocyanine that distils altogether as the organic light-emitting device charge transport layer, finds that the organic light-emitting device specific conductivity significantly increases, and along with the increase of doping level, the organic light-emitting device luminous efficiency enlarges markedly.Solar Engineering Materials and Solar Cells, V63, p83,2000 adopt the F4-TCNQ doping Phthalocyanine Zinc layer that distils altogether in PN type heterojunction photovolatic cell, found that the series resistance of device can reduce by two orders of magnitude after the illumination, and the photronic built-in voltage of doping type raises, the performance of doping device improves significantly, comparatively speaking, the PN junction photocell that do not mix almost be can't see the retardance behavior, and solar conversion efficiency is lower.But the dopant species of report is less at present, and generally adopts adulterating methods such as thermal evaporation, vacuum-sublimation, sputter, plasma method and molecular beam epitaxial growth, and this has relatively high expectations to doping techniques, technology and cost.
Summary of the invention
The purpose of this invention is to provide a kind of phthalocyanines organic semiconductor doping film material and preparation method thereof with excellent conductive performance and film forming properties.
The phthalocyanines organic semiconductor doping film material that the present invention proposes is the controllable doped four substituted phthalocyanine copper films of a kind of tetrachlorobenzoquinone and/or triphenyl phosphorus, and it mainly is made up of four substituted phthalocyanine copper, tetrachlorobenzoquinone and/or triphenyl phosphorus, wherein:
The chemical structural formula of (1) four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus is respectively:
Four substituted phthalocyanine copper tetrachlorobenzoquinone triphenyl phosphorus
(2) its composition weight share is counted:
1 part of tetrachlorobenzoquinone and/or triphenyl phosphorus (weight)
50-200 parts of four substituted phthalocyanine copper (weight)
Among the present invention, the mix degree of four substituted phthalocyanine copper films of tetrachlorobenzoquinone and/or triphenyl phosphorus can be controlled by the voltage and current size of regulating dopant species, doped solution concentration, regulated supply.
Tetrachlorobenzoquinone and/or the controllable doped four substituted phthalocyanine copper films of triphenyl phosphorus that the present invention proposes, its preparation process is:
(1) tetrachlorobenzoquinone and/or triphenyl phosphorus, four substituted phthalocyanine copper and the ionogen part by weight with 1:50～200:1～6 is dispersed in the organic solvent, be made into four substituted phthalocyanine copper doped solution, the solid content of solution is 0.001%～0.1% by weight;
(2) electrically-conductive backing plate is immersed in the above-mentioned four substituted phthalocyanine copper doped solution, voltage is 0～20V, electric current 0～10mA, with External Electrical Field 5～60 minutes, on electrically-conductive backing plate, obtain the controllable doped four substituted phthalocyanine copper films of tetrachlorobenzoquinone and/or triphenyl phosphorus, remove solvent, obtain the controllable doped phthalocyanine copper film of exsiccant tetrachlorobenzoquinone and/or triphenyl phosphorus, its bake out temperature is 50-70 ℃, and drying time is 3-5 hour, and the exsiccant film thickness is 10nm～1 μ m.
The present invention has obtained a kind of phthalocyanines organic semiconductor doping film material with excellent conductive performance and film forming properties by the strong donor molecule of electrochemical deposition method doping tetrachlorobenzoquinone and/or triphenyl phosphorus etc. in this metal phthalocyanine compound.The controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone and/or triphenyl phosphorus, advantage is: 1. by adjusting kind, proportioning and the consumption of doping agent, can obtain the controllable doped thin-film material of four substituted phthalocyanine copper classes of excellent conduction and optical absorptive character; 2. the electric conductivity of doping film significantly increases along with the increase of the rising of temperature or concentration of dopant; 3. at ambient temperature, the electric conductivity of the codope four substituted phthalocyanine copper films of triphenyl phosphorus and tetrachlorobenzoquinone can increase by 2～4 orders of magnitude; 4. the present invention has important use value to electro-conductive material, organic solar battery material, electroluminescent material, photoconductive material and photoelectric conversion material field.
Utilize electrochemical deposition method to prepare tetrachlorobenzoquinone and/or the controllable doped four substituted phthalocyanine copper films of triphenyl phosphorus, have that technology is simple, efficient is high, cost is low, doping level can adjusting, good film-forming property and thermal stability height, and its specific conductivity will improve 2～4 orders of magnitude than four substituted phthalocyanine copper films, can be applicable to field of photovoltaic materials such as conduction, sensing, photocell and electroluminescent.
Description of drawings
Fig. 1 is an electrochemical deposition method doper synoptic diagram (anode: ito glass, negative electrode: ito glass, electric depositing solution: four substituted phthalocyanine copper).
Fig. 2 is the mix electric conductivity of four substituted phthalocyanine copper films and the relation of doping content of tetrachlorobenzoquinone.
Fig. 3 is the tetrachlorobenzoquinone/triphenyl phosphorus codope four substituted phthalocyanines copper/electric conductivity of tetrachlorobenzoquinone film and relation of doping content, and wherein, the ratio of tetrachlorobenzoquinone/triphenyl phosphorus is 1/1 (by wt.).
Number in the figure: 1 is voltage stabilized source, and 2 is reometer, and 3 is electrode.
Embodiment
The controllable doped four substituted phthalocyanine copper films of above-mentioned tetrachlorobenzoquinone and/or triphenyl phosphorus, its preparation method is at normal temperatures tetrachlorobenzoquinone and/or triphenyl phosphorus, four substituted phthalocyanine copper and the ionogen ratio with 1:100～200:1～6 (weight) to be dispersed in the organic solvent, be made into four substituted phthalocyanine copper doped solution of various concentration, the solid content of solution is 0.001%～0.1% (weight).Used external electric field, voltage are 0～20V, electric current 0～10mA, 5～60 minutes time.Used solvent, be methylene dichloride, trichloromethane, toluene, dimethylbenzene, butanone, pimelinketone, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, methyl-sulphoxide, N, the mixed solvent of dinethylformamide, N,N-dimethylacetamide and above-mentioned any two kinds of solvent compositions.Used ionogen is trimethylphenyl ammonium iodide, trimethylammonium propyl ammonium chloride, tetrabutylammonium perchlorate, tetramethyl ammonium chloride, 4 bromide, Tetramethylammonium iodide, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, tetraethylammonium bromide, tetrabutylammonium chloride, tetra-n-butyl ammonium bromide, tetrabutylammonium iodide.Used electrically-conductive backing plate, be conduction tinsel, ito glass and above scribble the polyester chips of conducting medium.Adopt electrochemical deposition method, electrically-conductive backing plate is immersed in the above-mentioned four substituted phthalocyanine copper doped solution, with External Electrical Field 5～60 minutes, on electrically-conductive backing plate, obtain the controllable doped four substituted phthalocyanine copper films of tetrachlorobenzoquinone/triphenyl phosphorus, remove solvent, obtain the controllable doped phthalocyanine copper film of exsiccant tetrachlorobenzoquinone/triphenyl phosphorus.Bake out temperature is 50-70 ℃, and drying time is 3-5 hour, and the controllable doped phthalocyanine copper film thickness of exsiccant tetrachlorobenzoquinone/triphenyl phosphorus is 10nm～1 μ m.
The present invention will be described in detail below in conjunction with embodiment.Unless stated otherwise, given conductivity data all obtains on ZC-36 type superelevation resistance tester.
Embodiment 1
Chemical structural formula is respectively:
Four substituted phthalocyanine copper and tetrachlorobenzoquinones, with the mixed of 150:1 (by wt.), additional proportion is the tetrabutylammonium perchlorate of 2 (by wt.) again, uniform dissolution is made into solid content and is 0.01% four substituted phthalocyanine copper doped solution in trichloromethane.Adopt electrochemical deposition method galvanic deposit on the ITO conductive glass to obtain above-mentioned CuPc doped solution, the external electric field that it is used, voltage is 6V, electric current 4mA, 15 minutes time, bake out temperature is 60 ℃, and drying time is 4 hours, the phthalocyanine copper film that the exsiccant tetrachlorobenzoquinone is controllable doped, its thickness are 20nm.
The specific conductivity of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone as shown in Figure 2.
Embodiment 2
Identical with embodiment 1, but the ratio of four substituted phthalocyanine copper and tetrachlorobenzoquinone becomes 80:1 (weight ratio).
The specific conductivity of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone as shown in Figure 2.
Embodiment 3
Identical with embodiment 1, but the ratio of four substituted phthalocyanine copper and tetrachlorobenzoquinone becomes 50:1 (weight ratio).
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone as shown in Figure 2.
Embodiment 4
Identical with embodiment 1, but voltage becomes 4V, electric current becomes 1mA, and the time becomes 5 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone is as shown in table 1.
Embodiment 5
Identical with embodiment 1, but voltage becomes 1V, electric current becomes 0.5mA, and the time becomes 3 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone is as shown in table 1.
Identical with embodiment 1, but voltage becomes 10V, electric current becomes 8mA, and the time becomes 10 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone is as shown in table 1.
Identical with embodiment 1, but voltage becomes 15V, electric current becomes 8mA, and the time becomes 20 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone is as shown in table 1.
Chemical structural formula is respectively:
Four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus, mixed with 300:1:1 (by wt.), additional proportion is the tetrabutylammonium perchlorate of 5 (by wt.) again, and uniform dissolution is made into solid content and is 0.008% four substituted phthalocyanine copper doped solution in trichloromethane.Adopt electrochemical deposition method galvanic deposit on the ITO conductive glass to obtain above-mentioned CuPc doped solution, the external electric field that it is used, voltage is 6V, electric current 4mA, 15 minutes time, bake out temperature is 60 ℃, and drying time is 4 hours, the phthalocyanine copper film that exsiccant tetrachlorobenzoquinone/triphenyl phosphorus is controllable doped, its thickness are 20nm.
The specific conductivity of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus as shown in Figure 3.
Embodiment 9
Identical with embodiment 8, but the ratio of four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus becomes 160:1:1 (weight ratio).
The specific conductivity of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus as shown in Figure 3.
Embodiment 10
Identical with embodiment 8, but the ratio of four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus becomes 100:1:1 (weight ratio).
The specific conductivity of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus as shown in Figure 3.
Embodiment 11
Identical with embodiment 8, but voltage becomes 4V, electric current becomes 1mA, and the time becomes 5 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus is as shown in table 1.
Embodiment 12
Identical with embodiment 8, but voltage becomes 1V, electric current becomes 0.5mA, and the time becomes 3 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus is as shown in table 1.
Embodiment 13
Identical with embodiment 8, but voltage becomes 10V, electric current becomes 8mA, and the time becomes 10 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus is as shown in table 1.
Embodiment 14
Identical with embodiment 8, but voltage becomes 15V, electric current becomes 8mA, and the time becomes 20 minutes.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of this tetrachlorobenzoquinone/triphenyl phosphorus is as shown in table 1.
Comparing embodiment 1
With chemical structural formula be:
Four substituted phthalocyanine copper and tetrabutylammonium perchlorates, be that 150:2 (by wt.) mixes with the ratio, uniform dissolution is made into solid content and is 0.01% four substituted phthalocyanine copper solutionss in trichloromethane.Adopt electrochemical deposition method galvanic deposit on the ITO conductive glass to obtain above-mentioned CuPc solution, the external electric field that it is used, voltage is 6V, electric current 4mA, 15 minutes time, bake out temperature is 60 ℃, drying time is 4 hours, exsiccant four substituted phthalocyanine copper films, and its thickness is 20nm.
The conductivity data of this four substituted phthalocyanines copper film is as shown in table 1.
Comparing embodiment 2
With chemical structural formula be:
Tetrachlorobenzoquinone and tetrabutylammonium perchlorate, be that 1:2 (by wt.) mixes with the ratio, uniform dissolution is made into solid content and is 0.01% tetrachlorobenzoquinone solution in trichloromethane.Adopt electrochemical deposition method galvanic deposit on the ITO conductive glass to obtain above-mentioned tetrachlorobenzoquinone solution, the external electric field that it is used, voltage is 6V, electric current 4mA, 15 minutes time, bake out temperature is 60 ℃, drying time is 4 hours, and exsiccant tetrachlorobenzoquinone film, its thickness are 20nm.
The conductivity data of this tetrachlorobenzoquinone film is as shown in table 1.
Comparing embodiment 3
With chemical structural formula be:
Triphenyl phosphorus and tetrabutylammonium perchlorate, be that 1:2 (by wt.) mixes with the ratio, uniform dissolution is made into solid content and is 0.01% triphenyl phosphorus solution in trichloromethane.Adopt electrochemical deposition method galvanic deposit on the ITO conductive glass to obtain above-mentioned triphenyl phosphorus solution, the external electric field that it is used, voltage is 6V, electric current 4mA, 15 minutes time, bake out temperature is 60 ℃, drying time is 4 hours, and exsiccant triphenyl phosphorus film, its thickness are 20nm.
The conductivity data of this triphenyl phosphorus film is as shown in table 1.
The conductivity data of the controllable doped four substituted phthalocyanine copper films of table 1 tetrachlorobenzoquinone and/or triphenyl phosphorus
Claims (5)
1, the controllable doped four substituted phthalocyanine copper films of a kind of tetrachlorobenzoquinone and triphenyl phosphorus is characterized in that mainly being made up of four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus, wherein:
The chemical structural formula of (1) four substituted phthalocyanine copper, tetrachlorobenzoquinone and triphenyl phosphorus is respectively:
(a) four substituted phthalocyanine copper (b) tetrachlorobenzoquinone (c) triphenyl phosphorus
(2) its composition weight share is counted:
1 part of tetrachlorobenzoquinone and triphenyl phosphorus
50-200 parts of four substituted phthalocyanine copper.
2, the preparation method of the controllable doped four substituted phthalocyanine copper films of a kind of tetrachlorobenzoquinone as claimed in claim 1 and triphen phosphorus is characterized in that its concrete steps are:
(1) tetrachlorobenzoquinone and triphenyl phosphorus, four substituted phthalocyanine copper and the ionogen part by weight with 1:50～200:1～6 is dispersed in the organic solvent, is made into four substituted phthalocyanine copper doped solution, the solid content of solution is 0.001%～0.1% by weight;
(2) electrically-conductive backing plate is immersed in the above-mentioned four substituted phthalocyanine copper doped solution, voltage is 0～20V, electric current 0～10mA, with External Electrical Field 5～60 minutes, on electrically-conductive backing plate, obtain the controllable doped four substituted phthalocyanine copper films of tetrachlorobenzoquinone and triphenyl phosphorus, remove solvent, obtain the controllable doped phthalocyanine copper film of exsiccant tetrachlorobenzoquinone and triphenyl phosphorus; Its bake out temperature is 50-70 ℃, and drying time is 3-5 hour, and the exsiccant film thickness is 10nm～1 μ m.
3, a kind of preparation method of film according to claim 2, it is characterized in that said organic solvent is methylene dichloride, trichloromethane, toluene, dimethylbenzene, butanone, pimelinketone, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, methyl-sulphoxide, N, dinethylformamide, N, a kind of in the N-N,N-DIMETHYLACETAMIDE, or wherein any two kinds.
4, the preparation method of film according to claim 2, it is characterized in that said ionogen, is trimethylphenyl ammonium iodide, trimethylammonium propyl ammonium chloride, tetrabutylammonium perchlorate, tetramethyl ammonium chloride, 4 bromide, Tetramethylammonium iodide, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, tetraethylammonium bromide, tetrabutylammonium chloride, tetra-n-butyl ammonium bromide or tetrabutylammonium iodide.
5, the preparation method of film according to claim 2 is characterized in that said electrically-conductive backing plate, be conduction tinsel, ito glass or above scribble the polyester chips of conducting medium.
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| CNB2004100845752A CN100465178C (en) | 2004-11-25 | 2004-11-25 | Quadribasic phthalocyanine copper film with controllably doped tetrachlorobenzoquinone/triphenyl phosphorus and its prepn process |
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| CNB2004100845752A CN100465178C (en) | 2004-11-25 | 2004-11-25 | Quadribasic phthalocyanine copper film with controllably doped tetrachlorobenzoquinone/triphenyl phosphorus and its prepn process |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0511469A (en) * | 1991-07-03 | 1993-01-22 | Konica Corp | Electrophotographic sensitive body |
| CN1199069A (en) * | 1997-05-12 | 1998-11-18 | 东洋油墨制造株式会社 | Process for production of copper phthalocyanine |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0511469A (en) * | 1991-07-03 | 1993-01-22 | Konica Corp | Electrophotographic sensitive body |
| CN1199069A (en) * | 1997-05-12 | 1998-11-18 | 东洋油墨制造株式会社 | Process for production of copper phthalocyanine |
Non-Patent Citations (2)
| Title |
|---|
| "酞菁类光电导材料研究进展". 戴霞等.化工时刊，第18卷第8期. 2004 * |
| 共升华可控掺杂有机半导体薄膜材料的研究进展. 杨正龙等.功能材料，第35卷第3期. 2004 * |
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