Title of Invention

"AN IMPROVED ORGANIC OPTOELECTRONIC DEVICE"

Abstract This invention relates to an improved organic optoelectronic device comprising of an anode and a cathode with an active layer there between wherein the active layer corresponds to a single or bilayer or blend or tandem structure of one or more imidazolin-5-one molecule(s) or a combination of imidazolin-5-one molecules with other molecules such as C6o and its derivatives, fullerences, PCBM, pentacene, phthalocyanines and its derivatives, thiophenes and its derivatives, or other organic/inorganic semiconductors or conducting/semiconducting nano particles.
Full Text FIELD OF INVENTION
This invention relates to an improved organic optoelectronic device. BACKGROUND OF THE INVENTION/PRIOR ART
Conventionally, solar cells and photodetectors have been fabricated using inorganic materials like silicon and gallium arsenide (GaAs) using processes that require high temperatures. They also produce toxic materials (by products) during fabrication and disposal which can have adverse effects on the environment in the long run. However, in the past few years organic solar cells have gained popularity ever since the development of a two layer organic photovoltaic cell by Tang1. Availability of inexpensive and varied raw materials accompanied by an easy and ecology friendly fabrication procedure and the ability to tune molecular properties has made organic photovoltaic devices an attractive proposition2 4. Moreover, organic solar cells can have a flexible structure and are environment friendly, thus giving them an edge over the conventional inorganic solar cells.
A patent US20060071253 is known in the art related to a photoelectric conversion device comprising of at least two electrodes; and an organic photoelectric conversion film intervening between the said at least two electrodes; the organic photoelectric conversion film comprising a positive hole transporting material containing an arylidene compound having a specific structure, which is stated to be acidic.
Another literature by Lai Bahadur et al 2004 semiconductor science and technology 19531-536 known in the art. This is directed to the photosensitizing behaviour of 2-imidazolin-5-one, which studied earlier at sprayed ZnO thin film electrodes has been reinvestigated at nanocrystalline ZnO thin film electrodes prepared by the sol-gel method. By using semiconductor electrodes in the form of nanocrystalline thin films, all PEC cell parameters such as dye-sensitized photo voltage, photocurrent and IPCE were found to be higher as compared to those obtained with the use of sprayed thin film electrodes. Thus, through this investigation it has clearly been demonstrated that the same dye can perform better on nanocrystalline than sprayed thin film electrodes of the same semiconducting material.
The distinguishing features of the present invention as compared to US20060071253 are as follows:-
1. The present invention deals with the molecules having formula
wherein Rl = R2 = any substituent such as alkyl, aromatic,
heteroaromatic and halides, and R3 = aryl which is not
described by the formulae I and II of the US Patent.
2. The molecule of the present invention contains only double
bond which is different from that of the US document in which
they have shown a molecule defined by the formula III (wherein
R.sup.4,R.sup.5, R.sup.6 and n have the same meanings as in
the general formula (II), and Z.sup.l represents an atomic group
forming a 5- to 7 membered ring).
3. The absorption spectrum of the present invention also falls
outside the range of 50 to 150 nm of the US document.
4. The molecule of the present invention is tuned to be basic and
not acidic as claimed in the US document.
The non patent literature "Improved performance of 2-imidazolin-5-one as sensitizer at nanocrystalline ZnO thin film electrode in acetonitrile solution" differs from the present invention in the following ways-
1. The specific molecule used in this technical paper is 2-
imidazolin-5-one which is different from the present invention
molecule i.e. imidazolin-5-one.
2. The technical paper has shown that the molecule is used as
dye/dopant material showing photovoltaic parameters but the
present invention is not a dye/dopant sensitized photovoltaic
system.
3. The paper claims the use of the molecules as "Photosensitizer
for its application in a photoelectrochemical cell" but in the
present invention the molecule is used as an active layer in
organic solar cells.
4. The specific molecule used in this technical paper is 4-m-
rnethoxy-p-hydroxybenzylidene 2-m-methoxy-p-hydroxy styryl-
1-phenyl 2-imidazolin-5-one, which is different from the
molecule(s) used in the present invention. The specific
molecules that show solar cell effect are, however,
distinct/ different.
OBJECTS OF THE INVENTION
The primary object of the present invention is to provide an improved optoelectronic device which can be an organic solar cell or an organic photodetector or sensor which is environment and user friendly.
Another object of the present invention is to use material that are biodegradable and hence there is no problem of non-degradable waste from used and abandoned solar cells polluting the environment. This is particularly important as we need large area solar cells to meet the growing energy demand of the common man.
Another object of the present invention is to provide an improved organic solar cell which is efficient compared to the present available organic solar cells and is easy to fabricate along with an improved organic photodetector which has high sensitivity.
STATEMENT OF INVENTION
According to this invention there is provided an improved organic solar cell or organic photodetector/sensor comprising of anode and cathode with an active layer there between wherein the active layer corresponds to a single or bilayer or blend or tandem structure of one or more imidazolin-5-one molecules or a combination of imidazolin-5-one molecule$ with other molecules such as C60, fullerences, PCBM, pentacene, CuPC, thiophenes and other organic/inorganic semiconductors.
BRIEF DESCRIPTION OF THE ACCOMPANYING DRAWINGS
Further objects and advantages of this invention will be more apparent from the ensuing description when read in conjunction with the accompanying drawings and wherein:
Fig. l(a) shows the generic chemical structure of the imidazolin-5-one
molecules.
Fig. 1 (b) shows molecular structure of the three molecules mentioned in
the patent for their photovoltaic applications
Fig. 2(a) shows structure of the fabricated device.
Fig. 2(b) shows top view of the fabricated device structure.
Fig. 3 shows photograph of the actual fabricated device.
Fig. 4(a) shows photovoltaic effect in device fabricated using a single
layer of one of the imidazolin-5-one molecules (Molecule A).
Fig. 4(b) shows photovoltaic effect in device fabricated using a single
layer of another of the imidazolin-5-one molecules (Molecule B).
Fig. 4(c) shows photovoltaic effect in a bilayer device made of two
imidazolin-5-one molecules (Molecule B and C).
Fig. 5(a) shows sensor action in a device (during reverse bias) fabricated
using a single layer of imidazolin-5-one molecules (Molecule B).
Fig. 5(b) shows sensor action effect in a bilayer device (during reverse
bias) made of two imidazolin-5-one molecules (Molecule B and C).
DETAIL DESCRIPTION OF THE INVENTION WITH REFERENCE TO ACCOMPANYING DRAWINGS;

Fig. l(a) shows generic chemical structure of the imidazolin-5-one molecules wherein Ri, Ra and Ra can be modified as per requirements and can be any functional or chemical group like alkyl, aromatic, heteroarornatic, halides etc. such that the resulting molecule is basic or neutral in nature. In Fig. l(b) three specific examples of the molecules having the skeleton structure shown in Fig. l(a) are given.
The molecules (Figure l(b)) are as follows:
Molecule A:
(4Z)-4-(4-Methoxybenzylidene)-2-((E)-4-methoxystyryl)-1 -phenyl-1,4-dihydro-5H-imidazolin-5-one.
Molecule B:
(4Z)-4-(4-N,N-Dimethylaminobenzylidene)-l-methyl-2-phenyl-5H-imidazolin-5-one.
The above two molecules with solar cell effect can be used as a single layer in their respective devices. However, the active layer with bilayer or multilayer heterojunctions, as well as, bulk heterojunctions with these molecules and other molecules from the imidazolin-5-one family can also be formed. For example, bulk heterojunction active layer with molecule B above with molecule C shown below has been prepared.
Molecule C:
(4Z)-4-(4-Methoxyben2ylidene)-2-((E)-styryl)-l-phenyl-l,4-dihydro-5H-imidazolin-5-one..
Reference may be made to fig. 2 (a) and (b) for device description. Devices are formed at the intersection of the anode (ITO in this case) and cathode (Ca/Al in this case) layers.
The present invention provides an improved organic solar cell/organic photodetector comprising of an active layer intervening between two electrodes, which can be presented as follows:-
Anode/PEDOT:PSS/Imidazolin-5»one (s) Active layer/Cathode.
Anode represents a transparent/semitransparent conducting electrode such as Indium Tin Oxide (ITO) or a combination of ITO and PEDOT:PSS.
Active layer corresponds to a single or bilayer or blend or tandem structure of one or more imidazolin-5-one molecules or a combination of imidazolin-5-one molecules with other known molecules such as Ceo fullerenes, PCBM, pentacene, CuPC, thiophenes or other organic/inorganic semiconductors. Cathode refers to metals like Al, Au, Al, Ag, Cr, or material combination of material layers such as Ca and Al, Mg and Al, Mn and Al, or LiF and Al or any other conducting/semiconducting material or its combination with the said metals/materials.
Fig. 3 shows a photograph of the actual fabricated device whose characteristics are mentioned below.
The complete device fabrication procedure has been explained in [5] for a typical single layer (active layer of a single imidazolin-5-one molecule) device with ITO/PEDOT:PSS as the anode and Ca/Al as the cathode.
Different molecules belonging to this family were synthesized and tested for their potential application as photovoltaic materials. The molecular structure of some of these molecules is shown in Fig. l(b). Two examples of the obtained current density - voltage relations, depicting the photovoltaic behaviour, for single layer devices using Molecules A and B and one example for a bilayer structure using two of the molecules (Molecules B and C) are shown in Figures 4(a), (b) and (c) respectively. The characteristic in the fourth quadrant resembles generation of power from the device thereby indicating photovoltaic behaviour. Similarly the current density - voltage relations for sensor action are shown in Figures 5(a) and 5(b).
Choices of other molecules to make heterojunction with imidazoline-5-one to form the active layer would be fullerenes such as Ceo or its derivatives or could be carbon nanotube or any other electron transporting material with low mobility of holes. Similarly those imidazolin-5-one molecules which have a high electron mobility will require hole transporting materials with low electron mobility like thiophenes or its derivatives, phthalocyanines or its derivatives etc.
Imidazolin-5-one is the main chromophore which is responsible for the high fluorescence property of green fluorescent proteins (GFPs)6-7. This chromophore 4-(p-hydroxybenzylidene) imidazolin-5-one, is attached to the peptide backbone through 1 and 2 positions of the ring8. It is formed via a post translational internal cyclization of the Ser65-Tyr66-Gly67 tripeptide followed by 1,2-dehydrogenation of tyrosine. The substituents attached to imidazolin-5-one ring can be varied to alter the optical and electrical properties of the molecule that can thus be engineered for absorption in a desired frequency range. This ability to tune imidazolin-5-ones provides the designer with flexibility to alter the molecular properties as per requirement. In addition, the molecules score over other known materials for solar cell requirement because they are biodegradable and thus making them environment and user friendly.
References:
(1) CW Tang, Applied Physics Letters, 48(2), 1986, 183-185
(2) Attila J. Mozer; Niyazi Serdar Sariciftci, C. R. Chimie 9,
2006, 568-577.
(3) P. Peumans; A. Yakimov; S. R. Forrest, J. Appl. Phys.
93(7), 2003, 3693-3723.
(4) Harald Hoppe and Niyazi Serder Sariciftci, J Mater Res
(2004), Vol 19, No 7, 1924-1945.
(5) Vibhor Jain; Gitalee Bhattacharjya; Arun Tej; CK Suman;
R Gurunath; B Mazhari; SSK Iyer, Proceedings Asian
Symposium on Information Display (ASID) 2006, 244-
247.
(6) RY Tsien, Ann. Rev. Biochem., 67,1998, 509-544.

(7) M. Zimmer, chem. Review, 102, 2002, 759-781
(8) Gitalee Bhattacharjya; Arun Tej; SSK Iyer; Gurunath
Ramanathan, Proceedings of International Conference On
Molecules To Materials, 2006, 8-12
It is to be noted that the present invention is susceptible to modifications, adaptations and changes by those skilled in the art. Such variant embodiments employing the concepts and features of this invention are intended to be within the scope of the present invention, which is further set forth under the following claims:-





WE CLAIM:
1. An improved organic optoelectronic device comprising of an
anode and a cathode with an active layer there between wherein
the active layer corresponds to a single or bilayer or blend or
tandem structure of one or more imidazolin-5-one molecule(s)
or a combination of imidazolin-5-one molecules with other
molecules such as Ceo and its derivatives, fullerences, PCBM,
pentacene, phthalocyanines and its derivatives, thiophenes and
its derivatives, or other organic/inorganic semiconductors or
conducting/semiconducting nano particles.
2. The optoelectronic device mentioned in Claim 1 can be a solar
cell.
3. The optoelectronic device mentioned in Claim 1 can be an
photodetector or sensor.
4. An improved organic optoelectronic device as claimed in claim
I, 2 or 3 wherein the anode represents a
transparent/ semitransparent conducting/ semiconducting
electrode like the Indium Tin Oxide (ITO) or a combination of
ITO and PEDOT:PSS or other possible transparent/semi
transparent conducting/semiconducting electrodes.
5. An improved organic optoelectronic device as claimed in claim
1,2 or 3 wherein the cathode refers to metals like Al, Au, Ag, Cr
or combination of material layers such as Ca and Al, Mg and Al, Mn and Al, or LiF and Al or ITO or any other conducting/semiconducting material/metal or its combination with the metals/materials mentioned in this claim.
6. An improved organic optoelectronic device as claimed in any of
the preceding claims wherein the molecules used in the active
layer are having a generic formula as show in Figure l(a)
wherein R1, R2 and R3 can be any functional or chemical group
like alkyl, aromatic, heteroaromatic, halides etc. such that the
molecules are basic or neutral in nature.
7. An improved organic optoelectronic device as claimed in any of
the preceding claims wherein the molecules used in the active
layer are (4Z)-4-(4-Methoxybenzylidene)-2-((E)-4-methoxystyryl)-
l-phenyl-l,4-dihydro-5H-imidazolin-5-one and/or (4Z)-4-(4-
N,N-Dimethylaminobenzylidene)-l-methyl-2-phenyl-5H-
imidazolin-5-one.
8. An improved organic optoelectronic device as claimed in claim 6
and 7 wherein the molecules with solar cell effect or
photodetector action can be used as a single layer in their
respective devices.
9. An improved organic optoelectronic device as claimed in any of
the preceding claims wherein the active layer can be formed
with bilayer or multilayer heterojunctions as well as bulk heterojunctions with these molecules and other molecules from imidazolin-5-one family.
10. An improved organic optoelectronic device as claimed in claim 9
wherein said other molecules from imidazolin-5-one family
comprises (4Z)-4-(4-Methoxybenzylidene)-2-(E)-styryl)- 1-phenyl-
l,4-dihydro-5H-imidazolin-5-one, fullerenes such as Ceo or its
derivative or carbon nanotube or any other electron
transporting material with low mobility of holes.
11. An improved organic optoelectronic device as claimed in claim 9
wherein said other molecules from imidazolin-5-one family have
a high electron mobility and low hole mobility, thiophenes or its
derivatives, phthalocyanines or its derivatives or any other hole
transporting material with low mobility of electrons.
12. An improved organic optoelectronic device substantially as
herein described with reference to the accompanying drawings.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=ckIQ0tgbGnejUp7TVkKJdA==&loc=+mN2fYxnTC4l0fUd8W4CAA==


Patent Number 271903
Indian Patent Application Number 1231/DEL/2007
PG Journal Number 11/2016
Publication Date 11-Mar-2016
Grant Date 09-Mar-2016
Date of Filing 07-Jun-2007
Name of Patentee INDIAN INSTITUTE OF TECHNOLOGY KANPUR
Applicant Address KANPUR-208016, (U.P.)INDIA
Inventors:
# Inventor's Name Inventor's Address
1 RAMANATHAN GURUNATH ASSISTANT PROFESSOR, CHEMISTRY INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
2 S SUNDAR KUMAR IYER ASSISTANT PROFESSOR, ELECTRICAL ENGINEERING INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
3 GITALEE BHATTACHARJYA GRADUATED PHD STUDENT, CHEMISTRY INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
4 BASANTA KUMAR RAJBONGSHI PHD STUDENT, CHEMISTRY INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
5 ARUN TEJ M PHD STUDENT, ELECTRICAL ENGINEERING INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
6 VIBHOR JAIN MTECH DUAL DEGREE STUDENT, ELECTRICAL ENGINEERING INDIAN INSTITUTE OF TECHNOLOGY KANPUR-208016, (U.P.)INDIA
PCT International Classification Number H05B33/04
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA