# US 11,309,499 B2 · Electronic devices using organic small molecule semiconducting compounds

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- Number: US 11,309,499 B2
- Document ID: US11309499B2
- Status: Granted
- Kind: B2
- Application number: 14/378,829
- Filed: 2013-02-13
- Published: 2016-01-21
- Granted: 2022-04-19
- Earliest claimed: 2012-02-14
- Assignees: Next Energy Technologies, Inc.
- Applicants: Next Energy Technologies, Inc.
- Inventors: Arnold B. Tamayo; Bruno J. A. Caputo; Corey V. Hoven
- Web page: https://patentgrep.com/patent/US11309499B2

## CPC

- C07F 7/0816: {said ring comprising Si as a ring atom}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 30/353: {comprising blocking layers, e.g. exciton blocking layers}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 71/40: Thermal treatment, e.g. annealing in the presence of a solvent vapour
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- H10K 85/215: {comprising substituents, e.g. PCBM}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Small organic molecule semi-conducting chromophores containing a halogen-substituted core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

## Claims

### Claim 1

An electronic or optoelectronic device comprising a small molecule compound of Formula B:
wherein M is selected from sulfur (S), oxygen (O), selenium (Se), tellurium (Te), —N(R1)—, —C(R2)2—C(R3)2—, —CR2═CR3
wherein H2 is
wherein J1 is a nonentity;
wherein Q is a bivalent, trivalent, or tetravalent aryl or heteroaryl group;
wherein p is 1, 2, or 3;
wherein each X1, X2, Y1, and Y2 is halogen;
wherein each H1 and L1 are independently selected from -A1-B2,
wherein each B2 is independently selected from H and
wherein n is an integer between 0 and 5, inclusive, and m is an integer between 0 and 5, inclusive, and 1<m+n≤5 for each structure where m and n occur together;
wherein A1 is independently selected from substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group except thiophene,
where A2 is independently a substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group;
wherein B1 is a substituted or unsubstituted thiophene; and
wherein R1, R2, R3, R4, and R5 are each independently H or a substituent.

### Claim 2 (depends on 1)

An electronic or optoelectronic device according to claim 1, wherein said device is a solar cell.

### Claim 3 (depends on 1)

An electronic or optoelectronic device according to claim 1, wherein M is selected from sulfur (S), oxygen (O), and —N(R1).

### Claim 4 (depends on 1)

An electronic or optoelectronic device according to claim 1, wherein R1 is H, alkyl, or haloalkyl.

### Claim 5 (depends on 1)

An electronic or optoelectronic device according to claim 1 comprising a first electrode, a second electrode and an active layer between the first and second electrode, where the active layer comprises the small molecule compound of formula B.

### Claim 6 (depends on 5)

An electronic or optoelectronic device according to claim 5, where one electrode is transparent.

### Claim 7 (depends on 5)

An electronic or optoelectronic device according to claim 5, further comprising an electron-blocking, exciton-blocking, or hole-transporting layer.

### Claim 8 (depends on 5)

An electronic or optoelectronic device according to claim 5, further comprising a hole-blocking, exciton-blocking, or electron-transporting layer.

### Claim 9 (depends on 5)

An electronic or optoelectronic device according to claim 5, where the active layer further comprises an electron acceptor.

### Claim 10 (depends on 9)

An electronic or optoelectronic device according to claim 9, where the electron acceptor is a fullerene.

### Claim 11 (depends on 5)

An electronic or optoelectronic device according to claim 5, further comprising a dielectric layer.

### Claim 12 (depends on 5)

An electronic or optoelectronic device according to claim 5, further comprising a third electrode.

### Claim 13 (depends on 1)

An electronic or optoelectronic device according to claim 1, comprising a small molecule compound having Formula II:

### Claim 14 (depends on 13)

An electronic or optoelectronic device according to claim 13, wherein B1 is a substituted thiophene.

### Claim 15 (depends on 13)

An electronic or optoelectronic device according to claim 13, wherein Q is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phosphole, benzodithiophene, spirofluorene, spirothiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole, carbazole, 9,9-RR′-9H-fluorene
where R and R′═C1-C30 alkyl or C6-C30 aryl.

### Claim 16 (depends on 13)

An electronic or optoelectronic device according to claim 13, wherein B1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole.

### Claim 17 (depends on 13)

An electronic or optoelectronic device according to claim 13, where Q is 3,3′-RR′silylene-2,2′-bithiophene and R and R′ are both C1-C30 alkyl.

### Claim 18 (depends on 17)

An electronic or optoelectronic device according to claim 17, wherein Q is

### Claim 19 (depends on 18)

An electronic or optoelectronic device according to claim 18, wherein n+m=1.

### Claim 20 (depends on 19)

An electronic or optoelectronic device according to claim 19, wherein B1 is substituted thiophene.

### Claim 21 (depends on 20)

An electronic or optoelectronic device according to claim 20, wherein B1 is alkyl substituted thiophene.

### Claim 22 (depends on 13)

An electronic or optoelectronic device according to claim 13, wherein the small molecule compound of Formula II is

### Claim 23 (depends on 1)

The electronic or optoelectronic device of claim 1 comprising:
a first electrode;
a second electrode spaced apart from said first electrode; and
an active layer between said first electrode and said second electrode, wherein said active layer comprises a small molecule compound of Formula B.

### Claim 24 (depends on 23)

An electronic or optoelectronic device according to claim 23, further comprising a hole transporting layer between said first electrode and said active layer.