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Anthanthrene based compound and semiconductor device

a technology of anthanthrene and compound, which is applied in the direction of luminescent compositions, thermoelectric devices, organic chemistry, etc., can solve the problems of difficult to establish the stability of the molecule, the stability of the anthanthrene in the atmosphere is not satisfactory, and the decomposition reaction, etc., to achieve excellent stability in the atmosphere, enhance the mobility of the carrier, and improve the effect of stability

Inactive Publication Date: 2011-02-24
SONY CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

In the anthanthrene based compound according to an embodiment, a repeating unit (monomer unit) is stable in the atmosphere, and the repeating unit (monomer unit) has a wide π-system (having more aromatic rings). That is, each of the carbon atoms at the 6-position and the 12-position of the monomer unit in the anthanthrene based compound, etc. according to the embodiment is substituted with an element belonging to the Group 16, and therefore, the 6-position and the 12-position are not a reaction active site. Thus, the compound hardly causes a decomposition reaction by oxygen, light, water, high temperature or the like and is excellent in stability in the atmosphere. Also, larger overlapping of orbits is formed between adjacent molecules, and carrier mobility can be enhanced. That is, according to the embodiments, it is possible to provide a stable organic semiconductor material having high oxygen resistance, light fastness, heat resistance, water resistance and solvent resistance in the atmosphere and also having high carrier mobility. Therefore, by constituting a channel-forming region from the anthanthrene based compound, etc. according to the embodiment, the semiconductor device (organic transistor) according to the embodiment is able to display high carrier mobility and even after a thermal treatment at a high temperature in the atmosphere, is able to maintain high stability and high carrier mobility. Also, the anthanthrene based compound, etc. according to the embodiment has high stability, and therefore, it is possible to widen a width of a manufacturing process of a semiconductor device

Problems solved by technology

However, the polyacene compound as a constituent unit has reaction active sites within a molecule thereof (specifically, for example, so far as pentacene is concerned, an electron density is high at the 6-position and the 12-position, and the 6-position and the 12-position are a reaction active site) and easily causes a decomposition reaction by oxygen, light, water, high temperature or the like, and its stability in the atmosphere is not satisfactory.
Then, even in an oligo polyacene compound, so far as it has such a polyacene compound, it may be considered that it is difficult to establish stability of the molecule.

Method used

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  • Anthanthrene based compound and semiconductor device
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  • Anthanthrene based compound and semiconductor device

Examples

Experimental program
Comparison scheme
Effect test

example 2 (modification of example 1)

3. Example 2 (Modification of Example 1)

4. Example 3 (Anthanthrene based compound according to the second embodiment)

5. Example 4 (Semiconductor devices according to the first embodiment and second embodiment and others)

In the anthanthrene based compound according to the embodiment, X represents an element belonging to the Group 16. The “element belonging to the Group 16” as referred to herein is a generic name of elements belonging to the Group 16 of the periodic table; and oxygen (O), sulfur (S), selenium (Se), tellurium (Te) and polonium (Po) are classified in this. This element is also called an oxygen group element or a chalcogen. Also, each of the A segment, the B segment and the C segment per se is an organic semiconductor material obtained by substituting a dioxaanthanthrene based compound, specifically 6,12-dioxaanthanthrene (so-called peri-xanthenoxanthene, which is sometimes abbreviated as “PXX”) at from the 1-position to the 5-position and from the 7-position to the 11-p...

example 1

Example 1 is concerned with the anthanthrene based compound according to the first embodiment. The anthanthrene based compound of Example 1 is an anthanthrene based compound represented by the following structural formula (1) (oligo dichalcogeno anthanthrene based compound).

Each of the A segment, the B segment and the C segment per se is an organic semiconductor material obtained by substituting a dioxaanthanthrene based compound, specifically 6,12-dioxaanthanthrene (so-called peri-xanthenoxanthene, “PXX”) at from the 1-position to the 5-position and from the 7-position to the 11-position with any of the foregoing substituents including a hydrogen atom. Here, X represents an element belonging to the Group 16; n represents an integer of from 0 to 20; and m represents an integer of from 1 to 9.

Also, a bonding position in the A segment to the B segment is at least one of from the 1-position to the 5-position and from the 7-position to the 11-position; a bonding position in the B segmen...

example 2

Example 2 is a modification of Example 1. In Example 1, n was set to be 0, whereas in Example 2, n was set to be 1.

Specifically, a bonding position in the A segment to the B segment is one site at the 3-position; and a bonding position in the B segment to the A segment is one site at the 10-position. Also, a bonding position in the B segment to the C segment is one site at the 3-position; and a bonding position in the C segment to the B segment is one site at the 10-position. In the A segment, each of the substituents R1, R2, R4, R5, R7, R8, R10 and R11 is a hydrogen atom; and R9 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an ethylphenyl group. Also, in the B segment, each of the substituents R1, R2, R4, R5, R7, R8, R10 and R11 is a hydrogen atom. Furthermore, in the C segment, each of the substituents R1, R2, R4, R5, R7, R8, R10 and R11 is a hydrogen atom; and R3 is an arylalkyl group, specifically, an ethylaryl group, and more specifically an eth...

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Abstract

An anthanthrene based compound of the structural formula (1) is disclosed:wherein X represents an element of the Group 16; n represents an integer of from 0 to 20; m represents an integer of from 1 to 9; a bonding position in the A segment to the B segment, a bonding position in the B segment to the A segment, a bonding position in the B segment to the C segment, and a bonding position in the C segment to the B segment are at least one of from the 1-position to the 5-position and from the 7-position to the 11-position; and each of substituents R1, R2, R3, R4, R5, R7, R8, R9, R10 and R11 independently represents, for example, a substituent of one member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group and the like.

Description

CROSS REFERENCES TO RELATED APPLICATIONSThe present application claims priority to Japanese Priority Patent Application JP 2009-156459 filed in the Japan Patent Office on Jul. 1, 2009, the entire contents of which is hereby incorporated by reference.BACKGROUNDThe present application relates to an anthanthrene based compound and a semiconductor device including a semiconductor layer composed of such an anthanthrene based compound.In recent years, semiconductor devices including a semiconductor layer composed of an organic semiconductor material have been receiving considerable attention. In such a semiconductor device, a semiconductor layer can be coated and deposited at a low temperature as compared with a configuration including a semiconductor layer composed of an inorganic material. For that reason, such a semiconductor device is advantageous for realizing a large area and can be formed on a flexible substrate which is, however, low in heat resistance, such as plastics. Reduction...

Claims

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Application Information

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IPC IPC(8): H01L51/10C07D493/04
CPCC07D493/06H01L51/006H01L51/0073C09K2211/1088C09K11/06H05B33/10C09K2211/1011H01L51/0558H10K85/633H10K85/6574H10K10/484
Inventor KOBAYASHI, NORIHITO
Owner SONY CORP