# US 10,374,164 B2 · Organic photosensitive devices comprising a squaraine containing organoheterojunction and methods of making same

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- Number: US 10,374,164 B2
- Document ID: US10374164B2
- Status: Granted
- Kind: B2
- Application number: 14/845,895
- Filed: 2015-09-04
- Published: 2015-12-31
- Granted: 2019-08-06
- Earliest claimed: 2008-09-15
- Applicants: Mark E. Thompson; Siyi Wang; Elizabeth Mayo; Maria Dolores Perez
- Inventors: Mark E. Thompson; Siyi Wang; Elizabeth Mayo; Maria Dolores Perez
- Web page: https://patentgrep.com/patent/US10374164B2

## CPC

- C09B 57/007: {Squaraine dyes}
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- H10K 30/211: {comprising multiple junctions, e.g. double heterojunctions}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 71/164: {using vacuum deposition}
- H10K 85/211: {Fullerenes, e.g. C60}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An organic photosensitive optoelectronic device comprising at least one Donor-Acceptor heterojunction formed from a squaraine compound of formula I: wherein each of Ar1 and Ar2 is independently chosen from an optionally substituted aromatic group. The organic optoelectronic device described herein may also comprise a Donor-Acceptor heterojunction that is formed from at least two different squaraine compounds. A method of making the disclosed device, which may include at least one sublimation step for depositing the squaraine compound, is also disclosed.

## Claims

### Claim 1

An organic photosensitive optoelectronic device comprising:
an anode;
a cathode; and
at least one Donor-Acceptor heterojunction between the cathode and the anode, the heterojunction comprising at least two donor materials and at least one acceptor material, wherein at least one of the donor materials is a squaraine compound or a combination of squaraine compounds of formula I and forms a layer no more than 100 Å thick:
wherein each of Ar1 and Ar2 is independently chosen from an optionally substituted aromatic group.

### Claim 2 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein each of Ar1 and Ar2 is independently chosen from a group of formula II:
wherein each X is independently chosen from H, alkyl, alkoxy, halide, and hydroxy; and
Y is chosen from H or an optionally substituted amino group.

### Claim 3 (depends on 2)

The organic photosensitive optoelectronic device of claim 2, wherein at least one X group of formula II is hydroxy.

### Claim 4 (depends on 2)

The organic photosensitive optoelectronic device of claim 2, wherein each Y group is independently chosen from a group represented by the formula NR1R2, wherein each of R1 and R2 is independently chosen from H or an optionally substituted alkyl or aryl group.

### Claim 5 (depends on 4)

The organic photosensitive optoelectronic device of claim 4, wherein at least one of R1 and R2 is a substituted alkyl group.

### Claim 6 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein the squaraine compound is represented by formula III:
wherein each X is independently chosen from H, alkyl, alkoxy, halide, and hydroxy; and
each of R1 and R2 is independently chosen from an optionally substituted alkyl or aryl group.

### Claim 7 (depends on 6)

The organic photosensitive optoelectronic device of claim 6, wherein at least one X group of the compound of formula III is hydroxy.

### Claim 8 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein each of Ar1 and Ar2 is independently chosen from a group represented by the following formula V:
wherein each of rings A and B are optionally substituted C4-C8 rings, which are fused to form a bicycle saturated on unsaturated ring system comprising 6-14 carbon atoms.

### Claim 9 (depends on 8)

The organic photosensitive optoelectronic device of claim 8, wherein the squaraine compound of formula I is chosen from 2,4-Di-3-guaiazulenyl-1,3-dihydroxycyclobutenediylium dihydroxide and a salt thereof.

### Claim 10 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein the squaraine compound of formula I is chosen from 2,4-Bis [4-(N,N-dipropylamino)-2,6-dihydroxyphenyl; 2,4-Bis[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl; and salts thereof.

### Claim 11 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein each of Ar1 and Ar2 is independently chosen from a group represented by formula VI:
wherein n is chosen from 0, 1, 2, 3, 4, 5, and 6; and Z represents a linking group.

### Claim 12 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein the squaraine compound of formula I is not symmetric.

### Claim 13 (depends on 1)

The organic photosensitive optoelectronic device of claim 1, wherein the squaraine compound of formula I is amorphous.

### Claim 14

A method of forming an organic photosensitive optoelectronic device, said method comprising:
forming at least one Donor-Acceptor heterojunction over a first electrode, the heterojunction comprising at least two donor materials and at least one acceptor material, wherein at least one of the donor materials is formed by depositing a squaraine compound or a combination of squaraine compounds of formula I to a thickness of no more than 100 Å:
wherein each of Ar1 and Are is independently chosen from an optionally substituted aromatic group; and
forming a second electrode over the at least one Donor-Acceptor heterojunction.

### Claim 15 (depends on 14)

The method of claim 14, wherein said squaraine compound or combination of squaraine compounds is deposited by one or more processes chosen from vacuum deposition and solution processing.

### Claim 16 (depends on 14)

The method of claim 14, wherein the deposited squaraine compound or combination of squaraine compounds forms a discontinuous layer.

### Claim 17 (depends on 14)

The method of claim 14, wherein the step of forming at least one Donor-Acceptor heterojunction over a first electrode comprises depositing two or more different squaraine compounds of formula I.

### Claim 18

An organic photosensitive optoelectronic device comprising:
an anode;
a cathode; and
at least one Donor-Acceptor heterojunction between the cathode and the anode, the heterojunction comprising a donor material and an acceptor material, wherein the donor material is a mixture of at least two different squaraines of formula I and forms a layer no more than 100 Å thick:
wherein each of Ar1 and Are is independently chosen from an optionally substituted aromatic group.

### Claim 19 (depends on 18)

The organic photosensitive optoelectronic device of claim 18, wherein the mixture of at least two different squaraines comprises at least one squaraine chosen from 2,4-Bis [4-(N,N-dipropylamino)-2,6-dihydroxyphenyl; 2,4-Di-3-guaiazulenyl-1,3-dihydroxycyclobutenediylium dihydroxide; 2,4-Bis[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl; and salts thereof.