CN103483382A - Triarylamine triphenylphosphine functional material and preparation method thereof - Google Patents
Triarylamine triphenylphosphine functional material and preparation method thereof Download PDFInfo
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- CN103483382A CN103483382A CN201310394685.8A CN201310394685A CN103483382A CN 103483382 A CN103483382 A CN 103483382A CN 201310394685 A CN201310394685 A CN 201310394685A CN 103483382 A CN103483382 A CN 103483382A
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Abstract
The invention belongs to the field of functional materials, and particularly relates to a triarylamine triphenylphosphine functional material and a preparation method thereof. The structure of the functional material provided by the invention comprises triphenylphosphine and substituted triarylamine and has the advantages that (1) in the presence of P element, redundant lone pair electrons exist in the molecular structure, belonging to an intrinsic semiconductor; (2) the atomic radius of the P element is large, the steric hindrance is low, and a more stable semiconductor material can be obtained. The material provided by the invention is prepared by a two-step process by taking tris(4-hydroxy phenyl)phosphine, phenylamine, iodine, iodo-aromatic compound and potassium carbonate as start raw materials, and the preparation technology is simple.
Description
Technical field
The invention belongs to technical field of function materials, be specifically related to a kind of triarylamine triphenylphosphine functional materials and preparation method thereof.
Background technology
Organic charge transport material is that a class is when having current carrier (electronics or hole) to annotate the people, can realize that under electric field action thereby the oriented and ordered controlled migration of current carrier reaches the organic semiconductor material of transmission charge, comprise hole transport (p-type) and electric transmission (N-shaped) two classes.The organic hole transport material mainly contains poly-phenylene vinylene (ppv) (PPV) class, polythiophene class, polysilanes, triphenylmethane, tri-arylamine group, hydrazone class, pyrazolines, carbazoles, butadiene type etc. at present.Wherein, the tri-arylamine group material has preferably to electronics, lower ionization potential, higher hole migration, solvability and amorphous film-forming, stronger fluorescence property and light stability preferably, become the focus of research, extensively as hole mobile material, be applied to the numerous areas such as optical conductor, organic electroluminescent LED (OLED), organic solar batteries, refraction of light holography, field effect transistor.
The present invention be take the P element as core, with three aromatic amines, is connected, and forms the triphenylphosphine dendrimer, it is a kind of novel semi-conductor functional materials, its advantage is as follows: (1), due to the existence of P element, has unnecessary lone-pair electron in molecular structure, belong to the eigenmode semi-conductor.(2) P element and N element belong to same gang, and character is alike, but the atomic radius of P element is larger, sterically hindered little, can construct more stable semiconductor material.
Summary of the invention
The object of the invention is to propose class triarylamine triphenylphosphine functional materials and preparation method thereof.
The triarylamine triphenylphosphine functional materials that the present invention proposes, structurally contain triphenylphosphine, and replace triarylamine, and its structural formula is as follows:
Wherein R is a kind of of phenyl, 4-aminomethyl phenyl, 4-xenyl, 1-naphthyl.
The following several functional materialss of the special proposition of the present invention:
(1) Chinese: three (4-(N, N-hexichol amido) Phenylphosphines
English name: 4,4', 4''-phosphinetriyltris (N, N-diphenylaniline)
Molecular formula is C
54h
42n
3p, chemical structural formula is as follows:
(A)
(2) Chinese: three (4-(N-phenyl-N-(4-aminomethyl phenyl) amido) Phenylphosphines
English name: 4,4', 4''-phosphinetriyltris (N-phenyl-N-p-tolylaniline)
Molecular formula is C
57h
48n
3p, chemical structural formula is as follows:
(B)
(3) Chinese: three (4-(N-phenyl-N-(4-xenyl) amido) Phenylphosphines
English name: N, N', N''-(4,4', 4''-phosphinetriyltris (benzene-4,1-diyl)) tris (N-phenylbiphenyl-4-amine) molecular formula is C
72h
54n
3p, chemical structural formula is as follows:
(C)
(4) Chinese: three (4-(N-phenyl-N-(1-naphthyl) amido) Phenylphosphines
English name: N, N', N''-(4,4', 4''-phosphinetriyltris (benzene-4,1-diyl)) tris (N-phenylnaphthalen-1-amine)
Molecular formula is C
66h
48n
3p, chemical structural formula is as follows:
(D)
The invention allows for the preparation method of such functional materials, this material is starting raw material by three (4-hydroxy phenyl) phosphine, aniline, iodine, iodo aromatic compound and salt of wormwood, by two-step approach, prepares, and reaction equation is as follows:
Concrete steps are as follows:
Under nitrogen protection, three (4-hydroxy phenyl) phosphine is mixed with aniline, add iodine; be heated to 120 ℃, react 6 hours, add ethanol; filter, the gained solid mixes with iodo aromatic compound, salt of wormwood and n-dodecane, adds copper reduction; be heated to 180 ℃ of reactions 12 hours; cooling, add ethanol, filter; solid is purified by the vacuum-sublimation method, obtains the objective function material.
The accompanying drawing explanation
Fig. 1 is triarylamine triphenylphosphine functional materials structural formula.
Embodiment
The invention is further illustrated by the following examples
Embodiment 1
Under nitrogen protection, in three-necked bottle, 0.01mol tri-(4-hydroxy phenyl) phosphine is mixed with 0.04mol aniline, add 50mg iodine, be heated to 120 ℃, react 6 hours, add ethanol, filter, gained solid and 0.04mol iodobenzene, 0.02mol salt of wormwood and 100mL n-dodecane mix in three-necked bottle, add copper reduction 0.2g, be heated to 180 ℃ of reactions 12 hours, cooling, add ethanol, filter, solid is purified by the vacuum-sublimation method, obtain functional materials three (4-(N, N-hexichol amido) Phenylphosphine (A), yield: 66%, fusing point: > 300 ℃, ultimate analysis: C, 84.94, H, 5.50, N, 5.53, P, 4.03, calculated value C, 84.90, H, 5.54, N, 5.50, P, 4.05, mass spectrometric measurement: m/z:763 (100.0%).
Embodiment 2
Under nitrogen protection, in three-necked bottle, 0.01mol tri-(4-hydroxy phenyl) phosphine is mixed with 0.04mol aniline, add 50mg iodine, be heated to 120 ℃, react 6 hours, add ethanol, filter, gained solid and 0.04mol4-methyl iodobenzene, 0.02mol salt of wormwood and 100mL n-dodecane mix in three-necked bottle, add copper reduction 0.2g, be heated to 180 ℃ of reactions 12 hours, cooling, add ethanol, filter, solid is purified by the vacuum-sublimation method, obtain functional materials three (4-(N-phenyl-N-(4-aminomethyl phenyl) amido) Phenylphosphine (B), yield: 63%, fusing point: > 300 ℃, ultimate analysis: C, 84.90, H, 6.04, N, 5.24, P, 3.82, calculated value C, 84.94, H, 6.00, N, 5.21, P, 3.84, mass spectrometric measurement: m/z:805 (100.0%).
Embodiment 3
Under nitrogen protection, in three-necked bottle, 0.01mol tri-(4-hydroxy phenyl) phosphine is mixed with 0.04mol aniline, add 50mg iodine, be heated to 120 ℃, react 6 hours, add ethanol, filter, gained solid and 0.04mol4-iodine biphenyl, 0.02mol salt of wormwood and 100mL n-dodecane mix in three-necked bottle, add copper reduction 0.2g, be heated to 180 ℃ of reactions 12 hours, cooling, add ethanol, filter, solid is purified by the vacuum-sublimation method, obtain functional materials three (4-(N-phenyl-N-(4-xenyl) amido) Phenylphosphine (C), yield: 73%, fusing point: > 300 ℃, ultimate analysis: C, 87.12, H, 5.48, N, 4.26, P, 3.14, calculated value C, 87.16, H, 5.49, N, 4.24, P, 3.12, mass spectrometric measurement: m/z:991 (100.0%).
Embodiment 4
Under nitrogen protection, in three-necked bottle, 0.01mol tri-(4-hydroxy phenyl) phosphine is mixed with 0.04mol aniline, add 50mg iodine, be heated to 120 ℃, react 6 hours, add ethanol, filter, gained solid and 0.04mol1-naphthalene iodide, 0.02mol salt of wormwood and 100mL n-dodecane mix in three-necked bottle, add copper reduction 0.2g, be heated to 180 ℃ of reactions 12 hours, cooling, add ethanol, filter, solid is purified by the vacuum-sublimation method, obtain functional materials three (4-(N-phenyl-N-(1-naphthyl) amido) Phenylphosphine (D), yield: 39%, fusing point: > 300 ℃, ultimate analysis C, 86.70, H, 5.28, N, 4.64, P, 3.38, calculated value C, 86.72, H, 5.29, N, 4.60, P, 3.39, mass spectrometric measurement: m/z:913 (100.0%).
Claims (6)
1. triarylamine triphenylphosphine functional materials and preparation method thereof, is characterized in that this material structurally contains triphenylphosphine, and replace triarylamine, and its structural formula is as follows:
Wherein R is a kind of of phenyl, 4-aminomethyl phenyl, 4-xenyl, 1-naphthyl.
2. functional materials according to claim 1, is characterized in that R is phenyl, and the molecular formula of material is C
54h
42n
3p, chemical structural formula is as follows:
(A)
The name of this compound is called: three (4-(N, N-hexichol amido) Phenylphosphines
English name is: 4,4', 4''-phosphinetriyltris (N, N-diphenylaniline).
3. functional materials according to claim 1, is characterized in that R is the 4-aminomethyl phenyl, and the molecular formula of material is C
57h
48n
3p, chemical structural formula is as follows:
(B)
The name of this compound is called: three (4-(N-phenyl-N-(4-aminomethyl phenyl) amido) Phenylphosphines
English name is: 4,4', 4''-phosphinetriyltris (N-phenyl-N-p-tolylaniline).
4. functional materials according to claim 1, is characterized in that R is the 4-xenyl, and the molecular formula of material is C
72h
54n
3p, chemical structural formula is as follows:
(C)
The name of this compound is called: three (4-(N-phenyl-N-(4-xenyl) amido) Phenylphosphines
English name is: N, N', N''-(4,4', 4''-phosphinetriyltris (benzene-4,1-diyl)) tris (N-phenylbiphenyl-4-amine).
5. functional materials according to claim 1, is characterized in that R is the 1-naphthyl, and the molecular formula of material is C
66h
48n
3p, chemical structural formula is as follows:
(D)
The name of this compound is called: three (4-(N-phenyl-N-(1-naphthyl) amido) Phenylphosphine English name is: N, N', N''-(4,4', 4''-phosphinetriyltris (benzene-4,1-diyl)) tris (N-phenylnaphthalen-1-amine).
6. the preparation method as the described functional materials of claim 1～5, it is characterized in that this material is starting raw material by three (4-hydroxy phenyl) phosphine, aniline, iodine, iodo aromatic compound and salt of wormwood, by two-step approach, prepare, reaction equation is as follows:
Concrete steps are as follows:
Under nitrogen protection, three (4-hydroxy phenyl) phosphine is mixed with aniline, add iodine; be heated to 120 ℃, react 6 hours, add ethanol; filter, the gained solid mixes with iodo aromatic compound, salt of wormwood and n-dodecane, adds copper reduction; be heated to 180 ℃ of reactions 12 hours; cooling, add ethanol, filter; solid is purified by the vacuum-sublimation method, obtains the objective function material.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003317965A (en) * | 2002-04-25 | 2003-11-07 | Konica Minolta Holdings Inc | Organic electroluminescence element and display device |
| US20040002605A1 (en) * | 2002-06-27 | 2004-01-01 | Lelia Cosimbescu | Synthesis for quinacridone compounds |
| CN102046871A (en) * | 2008-06-02 | 2011-05-04 | 3M创新有限公司 | Electret webs with charge-enhancing additives |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003317965A (en) * | 2002-04-25 | 2003-11-07 | Konica Minolta Holdings Inc | Organic electroluminescence element and display device |
| US20040002605A1 (en) * | 2002-06-27 | 2004-01-01 | Lelia Cosimbescu | Synthesis for quinacridone compounds |
| CN102046871A (en) * | 2008-06-02 | 2011-05-04 | 3M创新有限公司 | Electret webs with charge-enhancing additives |
Non-Patent Citations (1)
| Title |
|---|
| YASUHIKO SHIROTA，ET AL.: "Organic materials for electronic and optoelectronic devices", 《J. MATER. CHEM.》 * |
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Application publication date: 20140101 |