CN102544370B - Application of compound with bending molecular structure - Google Patents
Application of compound with bending molecular structure Download PDFInfo
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- CN102544370B CN102544370B CN201110425228.1A CN201110425228A CN102544370B CN 102544370 B CN102544370 B CN 102544370B CN 201110425228 A CN201110425228 A CN 201110425228A CN 102544370 B CN102544370 B CN 102544370B
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Abstract
The invention provides an application of a compound with a bending molecular structure. The compound is used as an inductive layer material in a weak epitaxial growth thin film. Organic semiconductor thin film and apparatus with high mobility are prepared by weak epitaxial growth by means of the compound with the bending molecular structure taken as the inductive layer material. The high mobility reaches 2.2-2.3cm<2>/Vs which is equivalent to that of the organic semiconductor thin film prepared by a compound with rod-like linear molecular structure taken as the inductive layer. Compared with the compound with the rod-like linear molecular structure, as the inductive layer material has a bending molecular structure, lower processing temperature that is lower than 180 DEG C and is of better compatibility with flexible substrates such as polymers, the compound with the bending molecular structure can be widely applied in the fields such as flexible display and the like. Electronic elements based on the invention can be easily processed and prepared in a large area.
Description
Technical field
The present invention relates to the compound that a class has a bent portions minor structure and prepare the application in organic semiconductor thin-film and device.
Background technology
In recent years, along with the development of organic semiconductor science and technology, there is high carrier mobility organic semiconducting materials in information displaying, integrated circuit, photovoltaic cell and sensor, demonstrate wide application prospect.(the advanced material magazine such as Wang Haibo, Adv.Mater., 2007,19,2168-2171.) a kind of method-the weak epitaxial growth (WeakEpitaxy Growth) preparing plate-like organic semiconductor polycrystal film on amorphous substrate of reported first, prepared polycrystal film shows the carrier mobility performance of class monocrystalline level.Weak epitaxial growth refers to and utilizes orderly substrate or orderly substrate as inducing layer, rely on the epitaxial relationship of the existence between the crystal lattices of inducing layer material and the material crystals lattice grown on inducing layer, make the molecule of the material grown on inducing layer realize oriented growth; Another feature of weak extension is the molecule of inducing layer material and is weak Van der Waals force at the intermolecular forces of the molecule of inducing layer Epitaxial growth material, and molecule " is stood " and grown on inducing layer.Subsequently, a series of result of study shows, the molecule of inducing layer material and between the molecule of inducing layer Epitaxial growth material crystal lattice parameters matching degree higher, the film quality obtained is better.For regulate inducing layer molecule form the lattice parameter of crystal, Chinese invention patent (CN101955491A) gives a series of bar-shaped linear molecule as inducing layer material; Huang Lizhen etc. (advanced material magazine, Adv.Mater., 2011,23,3455-3459.) report and adopt bar-shaped linear molecule blends to regulate the method for inducing layer cell parameter.But there be limited evidence currently of has compound about bent portions minor structure as the report of inducing layer.Because the processing temperature of linear rodlike molecule compound is higher, usually more than 180 DEG C, its range of application is restricted.Compared to linear rodlike molecule compound, the compound with bent portions minor structure has lower processing temperature, and can have better compatibility with flexible substrate such as polymer, therefore material has more wide application prospect.
Summary of the invention
In order to overcome existing weak epitaxial film inducing layer material Problems existing, the invention provides the application that a class has bent portions substructuring compound, described compound is as the inducing layer material in weak epitaxial growth film; There is the compound of bent portions minor structure as inducing layer material by a class provided by the invention, prepare the organic semiconductor thin-film and device with high mobility with weak epitaxial growth; Described high mobility reaches 2.2-2.3cm
2/ Vs.
A class provided by the invention there is the molecular structural formula of the compound of bent portions minor structure and title as shown in table 1;
Table 1
A class provided by the invention has the preparation method of the compound of bent portions minor structure,
1) technology path of the synthesis of PM4P is as follows:
2) technology path of the synthesis of 2PM3P is as follows:
3) technology path of the synthesis of 3PM3P is as follows:
Wherein, PM4P, 2PM3P and 3PM3P are obtained by Suzuki coupling reaction.Involved reaction intermediate phenyl boric acid, m-dibromobenzene is known product to bromo-iodobenzene and 4-biphenylboronic acid; Compound I, II and IV is prepared according to published technical scheme.Compound I, the synthesis object of reference Physicochemical magazine B of II and IV collects (J.Phys.Chem B., 2001,105,8845-8860), the synthesis of compound III is with reference to biological organic and pharmaceutical chemistry (Bioorganic and medicinal Chemistry, 2008,16,9056-9064).
PPy4P, 2PPy3P and 3PPy3P are obtained by Suzuki coupling reaction equally, are m-dibromobenzene to be replaced with 2,6-dibromo pyridine, the preparation method of remaining same PM4P, 2PM3P and 3PM3P.
PTh4P and 2PTh3P is obtained by Suzuki coupling reaction equally, is dibromobenzene to be replaced with 2,5-dibromo thiophene, the preparation method of remaining same PM4P, 2PM3P.
Phenyl boric acid, with reference to the synthetic method of PM4P, 2PM3P and 3PM3P, only need be replaced with 4-fluorobenzoic boric acid (industrial products) by the synthesis of 2F-PM4P, 2F-2PM3P and 2F-3PM3P; 4-biphenylboronic acid replaces with 4 '-fluorodiphenyl-4-boric acid.Its synthetic method is shown in Chinese patent (CN101955491A).
2F-PPy4P, 2F-2PPy3P and 2F-3PPy3P are obtained by Suzuki coupling reaction, and synthetic method is synthesized with reference to the method for 2F-PM4P, 2F-2PM3P and 2F-3PM3P, only m-dibromobenzene need be replaced with 2,6-dibromo pyridine.
2F-PTh4P and 2F-2PTh3P is obtained by Suzuki coupling reaction equally, and synthetic method is synthesized with reference to the method for 2F-PM4P and 2F-2PM3P, m-dibromobenzene is replaced with 2,5-dibromo thiophene.
Synthesis for 4F-PM4P, 4F-2PM3P and 4F-3PM3P is synthesized with reference to the method for PM4P, 2PM3P and 3PM3P, only phenyl boric acid need be replaced with 3,5-difluoro-benzene boric acid (industrial products); 4-biphenylboronic acid replaces with 3 ', 5 '-two fluorodiphenyl-4-boric acid.Its synthetic method is shown in Chinese patent (CN101955491A).
4F-PPy4P, 4F-2PPy3P and 4F-3PPy3P are obtained by Suzuki coupling reaction, and synthetic method is synthesized according to the method for 4F-PM4P, 4F-2PM3P and 4F-3PM3P, m-dibromobenzene is replaced with 2,6-dibromo pyridine.
4F-PTh4P and 4F-2PTh3P is obtained by Suzuki coupling reaction, and synthetic method is synthesized with reference to the method for 4F-PM4P and 4F-2PM3P, m-dibromobenzene is replaced with 2,5-dibromo thiophene.
Above-mentioned all inducing layer materials can also obtain more sterling through vacuum sublimation.
Beneficial effect: the invention provides the application that a class has bent portions substructuring compound, described compound is as the inducing layer material in weak epitaxial growth film; There is the compound of bent portions minor structure as inducing layer material by a class provided by the invention, prepare the organic semiconductor thin-film and device with high mobility with weak epitaxial growth; Described high mobility reaches 2.2-2.3cm
2/ Vs is suitable with the mobility of the organic semiconductor thin-film adopting the compound of bar-shaped linearity molecular structure to prepare as inducing layer.Compare the compound of bar-shaped linearity molecular structure, because described inducing layer material has bending molecular structure, have lower processing temperature, processing temperature is lower than 180 DEG C, can be compatible better with the flexible substrate such as polymer, therefore have a wide range of applications in fields such as Flexible Displays.Use based on electronic component of the present invention easy large area processing preparation.
Accompanying drawing explanation
Fig. 1 is the device configurations of the first field-effect transistor that the present invention relates to, and wherein 1 is gate electrode, and 2 is insulating barrier, and 3 is inducing layer, and 4 is semiconductor layer, and 5 is source/drain electrode.
Fig. 2 is the device configurations of the second field-effect transistor that the present invention relates to, and wherein 1 is gate electrode, and 2 is insulating barrier, and 3 is inducing layer, and 4 is semiconductor layer, and 5 is source/drain electrode.
Fig. 3 adopts configuration shown in Fig. 1, and using PM4P as inducing layer, underlayer temperature 150 DEG C, VOPc is as the transfer characteristic curve of the field-effect transistor of semiconductor layer, and wherein mobility is 2.3cm
2/ Vs, threshold voltage-5V, on-off ratio 10
7.
Fig. 4 adopts configuration shown in Fig. 2, and using PM4P as inducing layer, underlayer temperature 150 DEG C, VOPc is as the transfer characteristic curve of the field-effect transistor of semiconductor layer, and wherein mobility is 2.2cm
2/ Vs, threshold voltage-5V, on-off ratio 10
7.
Embodiment
The present invention is further described below in conjunction with embodiment.
Embodiment surface heat growth used layer of silicon dioxide (SiO
2) heavily doped silicon chip be commercially produced product, use after cleaning, organic semiconducting materials is commercialization material, uses after buying final vacuum sublimation purification.Organic semiconducting materials used comprises: not containing metal phthalocyanine (H
2pc), containing metal phthalocyanine and derivative thereof, aphthacene, pentacene, rubrene ， perylene and derivative thereof; Containing metal phthalocyanine is: Nickel Phthalocyanine (NiPc), Tin Phthalocyanine (SnPc), CuPc (CuPc), Cobalt Phthalocyanine (CoPc), Phthalocyanine Zinc (ZnPc), phthalocyanine Pb (PbPc), ferrous phthalocyanine (FePc), the derivative of containing metal phthalocyanine is: ranadylic phthalocyanine (VOPc), TiOPc (TiOPc), phthalocyanine dichloro tin (SnCl
2pc), phthalocyanine oxygen tin (SnOPc), perfluoro CuPc (F
16cuPc the derivative Bao Kuo perylene Gan ， perylene acid amides of) ， perylene, Er Jia Ji perylene acid amides, Er Ben Ji perylene acid amides.
Embodiment 1
One deck SiO is grown in heat
2the surface inducing layer material that provides of vacuum moulding machine table 2 and the organic semiconducting materials successively respectively of silicon chip, finally, utilize mask plate plated metal gold (Au) as electrode, finally form field-effect transistor shown in Fig. 1.Wherein, underlayer temperature between 50-180 DEG C, vacuum degree 8 × 10
-4pascal (Pa).Heavily doped silicon as the gate electrode of field-effect transistor, SiO
2as insulating barrier, organic semiconductor is as active layer, and Au electrode is as source/drain electrode.Field-effect transistor is prepared with known technology.Table 2 provides the performance parameter of the field-effect transistor that a series of employing material provided by the invention is prepared as inducing layer.
Table 2
Embodiment 2
One deck SiO is grown in heat
2the surface of silicon chip utilize mask plate vacuum deposited metal gold (Au) respectively, the then inducing layer material that provides of vacuum moulding machine table 3 and organic semiconducting materials successively, finally form field-effect transistor shown in Fig. 2.Wherein, underlayer temperature between 50-180 DEG C, vacuum degree 8 × 10
-4pascal (Pa).Heavily doped silicon as the gate electrode of field-effect transistor, SiO
2as insulating barrier, organic semiconductor is as active layer, and Au electrode is as source/drain electrode.Field-effect transistor is prepared with known technology.Table 3 provides the performance parameter of the field-effect transistor that a series of employing material provided by the invention is prepared as inducing layer.
Table 3
The invention is not restricted to above-described embodiment.In general, the inducing layer material for weak epitaxial growth disclosed in this invention may be used in other organic semiconductor devices, forms the element in the integrated device of two and three dimensions.These integrated devices can be applied in integrated circuit, Active Matrix LCD At, transducer and photovoltaic cell aspect.Use based on electronic component of the present invention easy large area processing preparation.
Claims (8)
1. a class has the application of the compound of warp architecture molecule, it is characterized in that, described compound is used for the inducing layer material in weak epitaxial growth film; Title and the molecular structural formula of described compound are as follows;
(1) 1-(4-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)-3-phenyl benzene, molecular structural formula is
(2) 1-(4-1,1 ': 4 ', 1 "-terphenyl)-3-(4-1,1 '-dibiphenylyl) benzene; Molecular structural formula is
(3) 1,3-bis-(4-1,1 ': 4 ', 1 "-terphenyl) benzene; Molecular structural formula is
(4) 2-(4-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)-6-phenylpyridine; Molecular structural formula is
(5) 2-(4-1,1 ': 4 ', 1 "-terphenyl)-6-(4-1,1 '-dibiphenylyl) pyridine; Molecular structural formula is
(6) 2,6-bis-(4-1,1 ': 4 ', 1 "-terphenyl) pyridine; Molecular structural formula is
(7) 2-(4-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)-5-tolylthiophene; Molecular structural formula is
(8) 2-(4-1,1 ': 4 ', 1 "-terphenyl)-5-(4-1,1 '-dibiphenylyl) thiophene; Molecular structural formula is
(9) 1-[4-(4 " '-fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-3-[4-(1-fluorophenyl)] benzene; Molecular structural formula is
(10) 1-[4-(4 "-fluoro-1,1 ': 4 ', 1 "-terphenyl)]-3-[4-(4 '-fluoro-1,1 '-dibiphenylyl)] benzene; Molecular structural formula is
(11) 1,3-bis-(4-4 "-fluoro-1,1 ': 4 ', 1 "-terphenyl) benzene; Molecular structural formula is
(12) 2-[4-(4 " '-fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-6-[4-(1-fluorophenyl)] pyridine; Molecular structural formula is
(13) 2-[4-(4 "-fluoro-1,1 ': 4 ', 1 "-terphenyl)]-6-[4-(4 '-fluoro-1,1 '-dibiphenylyl)] pyridine; Molecular structural formula is
(14) 2,6-bis-(4-4 "-fluoro-1,1 ': 4 ', 1 "-terphenyl) pyridines; Molecular structural formula is
(15) 1-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-3-[4-(2,6-difluoro-benzene base)] benzene; Molecular structural formula is
(16) 1-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 "-terphenyl)]-3-[4-(3 ', 5 '-two fluoro-1,1 '-dibiphenylyl)] benzene; Molecular structural formula is
(17) 1,3-bis [4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 "-terphenyl)] benzene; Molecular structural formula is
(18) 2-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-6-[4-(2,6-difluoro-benzene base)] pyridine; Molecular structural formula is
(19) 2-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 "-terphenyl)]-6-[4-(3 ', 5 '-two fluoro-1,1 '-dibiphenylyl)] pyridine; Molecular structural formula is
(20) 2-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 "-terphenyl)]-6-[4-(3 ', 5 '-two fluoro-1,1 '-dibiphenylyl)] pyridine; Molecular structural formula is
(21) 2-[4-(4 "-fluoro-1,1 ': 4 ', 1 "-terphenyl)]-5-[4-(4 '-fluoro-1,1 '-dibiphenylyl)] thiophene; Molecular structural formula is
(22) 2-[4-(4 " '-fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-5-[4-(1-fluorophenyl)] thiophene; Molecular structural formula is
(23) 2-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 "-terphenyl)]-5-[4-(3 ', 5 '-two fluoro-1,1 '-dibiphenylyl)] thiophene; Molecular structural formula is
(24) 2-[4-(3 " ', 5 " '-two fluoro-1,1 ': 4 ', 1 ": 4 ", 1 " '-tetrad phenyl)]-5-[4-(2,6-difluoro-benzene base)] thiophene; Molecular structural formula is
2. a class as claimed in claim 1 has the application of the compound of warp architecture molecule, it is characterized in that, the underlayer temperature of compound when forming inducing layer that a described class has warp architecture molecule is not less than 50 DEG C, not higher than 180 DEG C.
3. a class as claimed in claim 1 has the application of the compound of warp architecture molecule, it is characterized in that, has the compound of bent portions minor structure as inducing layer material, prepare organic semiconductor thin-film and device with weak epitaxial growth by a described class.
4. a class as claimed in claim 3 has the application of the compound of warp architecture molecule, it is characterized in that, described organic semiconductor thin-film and device, using any one material described in claim 1 as inducing layer, prepared by employing weak epitaxial growth, the material of described organic semiconductor thin-film is not containing metal phthalocyanine, containing metal phthalocyanine and derivative thereof, aphthacene, pentacene, rubrene Huo perylene and derivative thereof; Described containing metal phthalocyanine is: Nickel Phthalocyanine, Tin Phthalocyanine, CuPc, Cobalt Phthalocyanine, Phthalocyanine Zinc, phthalocyanine Pb or ferrous phthalocyanine; The derivative of containing metal phthalocyanine is: ranadylic phthalocyanine, TiOPc, phthalocyanine dichloro tin, phthalocyanine oxygen tin, the derivative Wei perylene Gan ， perylene acid amides of perfluoro CuPc ， perylene, Er Jia Ji perylene acid amides, Er Ben Ji perylene acid amides.
5. a class as claimed in claim 3 has the application of the compound of warp architecture molecule, it is characterized in that, described organic semiconductor device is organic semiconductor field-effect transistor, described field-effect transistor is by gate electrode, insulating barrier, inducing layer, semiconductor layer and source/drain electrode connect and compose in turn, and wherein semiconductor layer adopts organic semiconductor thin-film according to claim 3.
6. a class as claimed in claim 4 has the application of the compound of warp architecture molecule, it is characterized in that, described organic semiconductor device is organic semiconductor field-effect transistor, described field-effect transistor is by gate electrode, insulating barrier, inducing layer, semiconductor layer and source/drain electrode connect and compose in turn, and wherein semiconductor layer adopts organic semiconductor thin-film according to claim 3.
7. a class as claimed in claim 3 has the application of the compound of warp architecture molecule, it is characterized in that, described organic semiconductor device is organic semiconductor field-effect transistor, described field-effect transistor is by gate electrode, insulating barrier, source/drain electrode, inducing layer and semiconductor layer connect and compose in turn, and wherein semiconductor layer adopts organic semiconductor thin-film according to claim 3.
8. a class as claimed in claim 4 has the application of the compound of warp architecture molecule, it is characterized in that, described organic semiconductor device is organic semiconductor field-effect transistor, described field-effect transistor is by gate electrode, insulating barrier, source/drain electrode, inducing layer and semiconductor layer connect and compose in turn, and wherein semiconductor layer adopts organic semiconductor thin-film according to claim 3.
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| CN101107244A (en) * | 2005-01-25 | 2008-01-16 | 先锋公司 | Organic compound, charge transport material and organic electroluminescent element containing the same |
| CN101562230A (en) * | 2009-05-25 | 2009-10-21 | 中国科学院长春应用化学研究所 | Organic solar cell adopting weak epitaxial growth film as donor |
| CN101955491A (en) * | 2009-12-22 | 2011-01-26 | 上海中科联和显示技术有限公司 | Induced layer material for weak epitaxial growth thin film of non-planar metal phthalocyanin |
| CN102154688A (en) * | 2011-03-25 | 2011-08-17 | 长春圣卓龙电子材料有限公司 | Rubrene weak epitaxial growth thin film and application thereof in organic thin-film transistor |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101107244A (en) * | 2005-01-25 | 2008-01-16 | 先锋公司 | Organic compound, charge transport material and organic electroluminescent element containing the same |
| CN101562230A (en) * | 2009-05-25 | 2009-10-21 | 中国科学院长春应用化学研究所 | Organic solar cell adopting weak epitaxial growth film as donor |
| CN101955491A (en) * | 2009-12-22 | 2011-01-26 | 上海中科联和显示技术有限公司 | Induced layer material for weak epitaxial growth thin film of non-planar metal phthalocyanin |
| CN102154688A (en) * | 2011-03-25 | 2011-08-17 | 长春圣卓龙电子材料有限公司 | Rubrene weak epitaxial growth thin film and application thereof in organic thin-film transistor |
Non-Patent Citations (1)
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| Fluorescence and laser properties of D2-, C2- and D3 symmetry series oligophenylenes;R. Mabbs et al.;《Spectrochimica Acta Part A》;20031231;第59卷;第1329-1339页 * |
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