Organic compounds containing squaric acid or croconic acid moieties for application in electronic devices

Abstract

A compound containing a squaric acid or a croconic acid group as an anchoring group. The compound containing a squaric acid or a croconic acid group has formula 1: ##STR00001##
where n is 1 or 2, and D is selected from an alkyl, aryl, aralkyl, heteroalkyl, heteroaryl or heteroaralkyl substituent, and each substituent is substituted or unsubstituted.

Claims

1. A compound, comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2): ##STR00066## wherein, in formula (2), n is 1 or 2, wherein A.sub.1 is selected from the following moieties ##STR00067## ##STR00068## ##STR00069## wherein, at each occurrence and independently: G is a cyclic or acyclic substituted, or straight or branched alkyl; f=1 or 2; K is O, S, or N; g=0 or 1, wherein the alkyl, alkoxy, amine, thiole group of (K).sub.g-(G).sub.f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

2. The compound of claim 1, wherein A.sub.1 is selected from the following moieties ##STR00070## ##STR00071## ##STR00072##

3. The compound of claim 1, wherein A.sub.1 is selected from the following moieties ##STR00073## ##STR00074##

4. The compound of claim 1, which is represented by any one of ##STR00075##

5. The compound of claim 1, which is any one of ##STR00076## ##STR00077##

6. The compound of claim 1, wherein the compound is ##STR00078##

7. The compound of claim 1, which is represented by ##STR00079##

8. A light-emitting device, a Schottky barrier diode, a rectifier, a field effect transistor, a photovoltaic device, a photochemical device, a memory device, a sensing device, a display, or a photo-catalytical water splitting device that comprises: a compound comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2): ##STR00080## wherein, in formula (2), n is 1 or 2, wherein A.sub.1 is selected from the following moieties ##STR00081## ##STR00082## ##STR00083## wherein, at each occurrence and independently: G is a cyclic or acyclic substituted, or straight or branched alkyl; f=1 or 2; K is O, S, or N; g=0 or 1, wherein the alkyl, alkoxy, amine, thiole group of (K).sub.g-(G).sub.f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

9. An assembly for use in an electronic device, said assembly comprising: a) a conducting substrate, a semiconducting substrate, or an insulating organic or inorganic substrate, said substrate having a surface, b) a layer of a compound present on said surface, wherein said layer is covalently attached to said surface via the squaric acid or croconic acid group of said compound, and c) an organic layer, an inorganic layer, or an electrolyte layer deposited on said layer, wherein said said compound is a compound comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2): ##STR00084## wherein, in formula (2), n is 1 or 2, wherein A.sub.1 is selected from the following moieties ##STR00085## ##STR00086## ##STR00087## wherein, at each occurrence and independently: G is a cyclic or acyclic substituted, or straight or branched alkyl; f=1 or 2; K is O, S, or N; g=0 or 1, wherein the alkyl, alkoxy, amine, thiole group of (K).sub.g-(G).sub.f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) In the following, reference is made to the figures, wherein

(2) FIG. 1 shows exemplary synthesis routes for exemplary compounds of the disclosure.

(3) FIG. 2 shows how the work function of a component is shifted by a compound of the disclosure anchored to its surface due to dipole moment of the compound of the disclosure.

(4) FIG. 3 shows an energy scheme of a DSSC with main components of a semiconductor to which an sensitizer dye is attached and electrolyte (conventional electrolyte being I3-/I-redox pair).

(5) Depending of dipole moment of the adsorbent (sensitizer dye or co-adsorbent) the work function (conduction band edge CB) of semiconductor is shifted. Voc is determined by the difference in the quasi-Fermi level of TiO.sub.2 and redox of the electrolyte DSSC; the shift in work function of semiconductor has a direct influence on Voc and efficiency of the DSSC.

(6) FIG. 4 shows the work function shift of a TiO.sub.2 substrate on which an exemplary compound according to the disclosure is anchored.

(7) FIG. 5 shows the light absorption capability of a TiO.sub.2 substrate on which an exemplary compound according to the disclosure is anchored.

(8) FIG. 6 shows exemplary assemblies comprising a first and a second substrate and a first and a second layer of compound(s) of the present disclosure which are anchored to the respective substrate.

(9) For example, by such a device a junction between two substrates is formed.

DETAILED DESCRIPTION OF THE EMBODIMENTS

(10) The invention will now be further described by reference to the following examples which are given to illustrate, not to limit the present disclosure.

EXAMPLES

Example 1

(11) FIGS. 1 A to E show examples of synthesis routes showing the structural design and functionalization of exemplary compounds of the disclosure.

Example 2

(12) Results for tests of compound 1, an exemplary compound of the disclosure, are presented in FIGS. 4 and 5. As can be seen compound 1 modifies the work function as well as the light absorption capability of a TiO.sub.2 substrate.

(13) FIG. 4 shows the work function shift (0.3 eV) of TiO.sub.2 component when compound 1 is attached to its surface. The work function were determined by Kelvin Probe method by measuring 2 samples, respectively.

(14) The work function shift is due to the dipole moment vector of compound 1 directed away from surface which was calculated to be 8.16 D.

(15) FIG. 5 shows the improvement of light absorption capability of a TiO.sub.2 substrate by anchoring compound 1 on its surface. Depicted are the transmission spectrum of TiO.sub.2 substrate alone (left graph) and for comparison the transmission spectrum of TiO.sub.2 modified by compound 1 (right graph). While TiO.sub.2 alone is capable of adsorbing light only up to 350 nm, when compound 1 is attached light up to about 500 nm is adsorbed.

Example 3

(16) Given is an example of a mixture of two compounds of the disclosure to improve light absorption capability of the semiconductor (3) and at the same time increase tunneling barrier (4) from TiO.sub.2 to the electrolyte so as to suppress recombination which is concurrent process in a DSSC.

(17) ##STR00064##

(18) Given is an example of a mixture of two compounds of the disclosure to improve light absorption capability of the semiconductor (5) and at the same time shifting work function to higher values away from vacuum level (6).

(19) ##STR00065##

(20) The features of the present disclosure disclosed in the specification, the claims and/or in the accompanying drawings may, both separately and in any combination thereof, be material for realizing the disclosure in various forms thereof.

(21) The present application claims priority to European Patent Application 12 167 017.8, filed in the European Patent Office on May 7, 2012, the entire contents of which being incorporated herein by reference.