Thienothiophene derivatives

Details Thienothiophene derivatives Thienothiophene derivatives

2002-07-09

2004-11-16

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C252S299610, C252S299620, C252S299300, C549S043000, C549S046000, C549S047000, C549S048000

Reexamination Certificate

active

06818260

ABSTRACT:

FIELD OF INVENTION
The invention relates to new thienothiophene derviatives. The invention further relates to their use as semiconductors or charge transport materials, in optical, electrooptical or electronic devices like for example organic field effect transistors (FET or OFET) for thin film transistor liquid crystal displays and integrated circuit devices such as radio frequency identification (RFID) tags, electroluminescent devices in flat panel displays, and in photovoltaic and sensor devices. The invention further relates to a field effect transistor, light emitting device or identification (ID) tag comprising the new thienothiophene derivatives.
BACKGROUND AND PRIOR ART
Organic materials have recently shown promise as the active layer in organic based thin film transistors and organic field effect transistors [see H. E. Katz, Z. Bao and S. L. Gilat,
Acc. Chem. Res.,
2001, 34, 5, 359]. Such devices have potential applications in smart cards, security tags and the switching element in flat panel displays. Organic materials are envisaged to have substantial cost advantages over their silicon analogues if they can be deposited from solution, as this enables a fast, large-area fabrication route.
The performance of the device is principally based upon the charge carrier mobility of the semiconducting material and the current on/off ratio, so the ideal semiconductor should have a low conductivity in the off state, combined with a high charge carrier mobility (>1×10
−3
cm
2
V
−1
s
−1
). In addition, it is important that the semiconducting material is relatively stable to oxidation i.e. it has a high ionisation potential, as oxidation leads to reduced device performance.
Compounds known in prior art for use as semiconductors are the fused dimer of dithienothiophene (DTT) and &agr;,&agr;′-bis(dithieno[3,2-b:2′,3′-d]thiophene (BDT) having the structures shown below.
BDT and DDT are described for example in F. de Jong and M. J. Janssen, J. Org. Chem., 1971,36,12, 1645; S. Inaoka and D. M. Collard, J. Mater. Chem., 1999, 9, 1719; H. Sirringhaus et al, Appl. Phys. Lett. 1997,71 (26), 3871; X-C. Li et al, J. Am. Chem. Soc., 1998,120, 2206, and in the international patent application WO 99/12989.
In particular BDT, which has been extensively studied, has been shown to be an effective p-type semiconductor for organic FETs with a very high charge carrier mobility of 0.02-0.05 cm
2
/V. BDT also has been found in the solid state to have a completely coplanar formation, and to be more planar than oligomers of thiophene.
However, the materials described in prior art have several disadvantages. BDT has a high melting point and is very insoluble, therefore, if used as the active layer in an organic thin film transistor, it cannot be readily solution processed.
As a result, for applications like FETs, prior art materials like BDT are usually deposited as a thin film by vacuum deposition, which is an expensive processing technique that is unsuitable for the fabrication of large-area films.
It was an aim of the present invention to provide new organic materials for use as semiconductors or charge transport materials, which are easy to synthesize, have high charge mobility, and good processibility. The materials should be easily processible to form thin and large-area films for use in semiconductor devices. Other aims of the invention are immediately evident to those skilled in the art from the following description.
It was found that these aims can be achieved by providing thienothiophenes as described below.
U.S. Pat. No. 4,639,328 discloses compounds with a thienothiophene group for use as components of liquid crystalline phases, but does not provide any suggestion to semiconductor materials.
Definition of Terms
The terms ‘liquid crystalline or mesogenic material’ or ‘liquid crystalline or mesogenic compound’ means materials or compounds comprising one or more rod-shaped, lath-shaped or disk-shaped mesogenic groups, i.e. groups with the ability to induce liquid crystal phase behaviour. The compounds or materials comprising mesogenic groups do not necessarily have to exhibit a liquid crystal phase themselves. It is also possible that they show liquid crystal phase behaviour only in mixtures with other compounds.
SUMMARY OF THE INVENTION
One object of the invention is to provide thienothiophene compounds of formula I
R
1
—Z
1
—(A
1
—Z
2
)
m
—(T—Z
3
)
n
—(A
2
—Z
4
)
o
—R
2
  I
wherein
R
1
and R
2
are independently of each other H, halogen, CN, NO
2
, straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which may be unsubstituted, mono- or poly-substituted by F, Cl, Br, I or CN, it being also possible for one or more non-adjacent CH
2
groups to be replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR
0
—, —SiR
0
R
00
—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
R
0
and R
00
are independently of each other H or alkyl with 1 to 12 C-atoms,
A
1
and A
2
are independently of each other an alicyclic or aromatic group that may also comprise one or more hetero atoms and one or more fused rings, and A
1
may also denote T,
Z
1
to Z
4
are independently of each other —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR
0
—, —NR
0
—CO—, —OCH
2
—, —CH
2
O—, —SCH
2
—, —CH
2
S—, —CF
2
O—, —OCF
2
—, —CF
2
S—, —SCF
2
—, —CH
2
CH
2
—, —CF
2
CH
2
—, —CH
2
CF
2
—, —CF
2
CF
2
—, —CH═N—, —N═CH—, —N═N—, —CH═CR
0
—, —CX
1
═CX
2
—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
X
1
and X
2
are independently of each other H, F, Cl or CN,
T is a group consisting of 3, 4, 5 or 6 thiophene rings which may also be mono- or polysubstituted by R
1
, wherein at least 3 of the thiopene rings are fused together,
m and o are independently of each other 0, 1, 2 or 3, and
n is 1, 2 or 3.
Another object of the invention is the use of compounds of formula I as semiconductors or charge transport materials, in particular in optical, electrooptical or electronic devices, like for example components of integrated circuitry, field effect transistors (FET) for example as thin film transistors in flat panel display applications or for Radio Frequency Identification (RFID) tags, or in semiconducting components for organic light emitting diode (OLED) applications such as electroluminescent displays or backlights of flat panel displays, for photovoltaic or sensor devices, as electrode materials in batteries, as photoconductors and for electrophotographic applications.
Another object of the invention is a field effect transistor, for example as a component of integrated circuitry, as a thin film transistor in flat panel display applications, or in an RFID tag, comprising one or more compounds of formula I.
Another object of the invention is a semiconducting component, for example in OLED applications like electroluminescent displays or backlights of flat panel displays, in photovoltaic or sensor devices, as electrode materials in batteries, as photoconductors and for electrophotographic applications, comprising one or more compounds of formula I.
Another object of the invention is a security marking or device comprising an RFID or ID tag or a FET according to the invention.
Upon further study of the specification and appended claims, further objects and advantages of this invention will become apparent to those skilled in the art.


REFERENCES:
patent: 4639328 (1987-01-01), Krause et al.
patent: 6645401 (2003-11-01), Giles et al.
patent: 6676857 (2004-01-01), Heeney et al.
patent: 6695978 (2004-02-01), Worrall et al.
patent: WO 99/12989 (1999-03-01), None
Kossmehl, Gerhard et al., “Über Polyarylenalkenylene und Polyheteroarylenaikenylene, 13a)”, 1297 Makromolekulare Chemie, vol. 183 (1982).
Haristoy, D. et al., “Structure and photoconductive behaviour of a sanidic liquid crystal”, Liquid Crystals, 2000, vol. 27, No. 3, pp. 321-328.
Kieboorns, Rafaël et al., “Synthesis, Electrical,

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