# US 9,040,744 B2 · Polycyclic organic compound, optically anisotropic film and method of production thereof

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- Number: US 9,040,744 B2
- Document ID: US9040744B2
- Status: Granted
- Kind: B2
- Application number: 12/522,914
- Filed: 2008-01-11
- Published: 2010-08-26
- Granted: 2015-05-26
- Earliest claimed: 2007-01-11
- Assignees: Crysoptix KK
- Applicants: Valery S. Kuzmin; Alexey Nokel
- Inventors: Valery S. Kuzmin; Alexey Nokel
- Web page: https://patentgrep.com/patent/US9040744B2

## CPC

- G02B 5/305: {including organic materials, e.g. polymeric layers}
- C07D 213/34: to which a second hetero atom is attached
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 241/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 271/107: with two aryl or substituted aryl radicals attached in positions 2 and 5
- C07D 333/76: Dibenzothiophenes
- C07D 487/04: Ortho-condensed systems
- C07D 487/14: Ortho-condensed systems
- C07D 498/04: Ortho-condensed systems
- C07D 498/14: Ortho-condensed systems
- C09K 19/3444: {the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine}
- C09K 19/3452: {Pyrazine}
- C09K 19/3455: {Pyridazine}
- C09K 19/3458: {Uncondensed pyrimidines}
- C09K 19/3477: {the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom}
- C09K 19/348: {containing at least two nitrogen atoms}
- C09K 19/3491: {having sulfur as hetero atom}
- G02B 1/14: Protective coatings, e.g. hard coatings
- G02B 5/3083: {Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001)}
- G02F 1/13363: Birefringent elements, e.g. for optical compensation
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- G02F 1/133633: {using mesogenic materials}
- G02F 1/133634: {the refractive index Nz perpendicular to the element surface being different from in-plane refractive indices Nx and Ny, e.g. biaxial or with normal optical axis}
- Y10T 428/2848: Three or more layers
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The polycyclic organic compounds which are substantially transparent for an electromagnetic radiation in the visible spectral range, an anisotropic optical film comprising at least one polycyclic organic compound and a method of producing thereof are disclosed. The polycyclic organic compounds have a general formula (I) wherein A and B are acid groups, n is the number of phenyl rings in the range from 3 to 10; m is 0, 1, 2 or 3; l is 1, 2, or 3, p is 1, 2, 3, 4, 5 or 6, C is a counterion from a list comprising H+, NH+4, Na+, K+, Li+, Cs+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p).

## Claims

### Claim 1

A polycyclic organic compound of structural formula (Ib)
wherein
A and B are acid groups independently selected from the list consisting of sulfonic and carboxylic; m is 0 or 1; and l is 1;
C is a counterion selected from the list consisting of H+, NH+4, Na+, K+, Li+, Cs+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p); and p is 1, 2, 3, 4, 5 or 6;
X is a bivalent group selected independently from the group consisting of —SO2—, —O—, and —NH—;
wherein said organic compound is transparent for electromagnetic radiation in the visible spectral range.

### Claim 2 (depends on 1)

An organic compound according to claim 1, wherein the compound has the structural formula (II):

### Claim 3

A polycyclic organic compound of structural formula (III)
wherein
A and B are acid groups independently selected from the list consisting of sulfonic and carboxylic; m is 0 or 1; and l is 1;
C is a counterion selected from the list consisting of H+, NH+4, Na+, K+, Li+, Cs+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p); and p is 1, 2, 3, 4, 5 or 6;
X1, X2, and X3, each is a bivalent group selected independently from the group consisting of —SO2—, —O—, and —NH—;
wherein said organic compound is transparent for electromagnetic radiation in the visible spectral range.

### Claim 4

A polycyclic organic compound of structural formula (IV)
wherein
A and B are acid groups independently selected from the list consisting of sulfonic and carboxylic; m is 0 or 1; and l is 1;
C is a counterion selected from the list consisting of H+, NH+4, Na+, K+, Li+, Cs+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p); and p is 1, 2, 3, 4, 5 or 6; and
X1, X2, and X3, each is a bivalent group selected independently from the group consisting of —SO2—, —O—, and —NH—;
wherein said organic compound is transparent for electromagnetic radiation in the visible spectral range.

### Claim 5

An anisotropic optical film, which comprises at least one organic layer comprising at least one polycyclic organic compound of a structural formula (I)
wherein
n is the number of phenyl rings from 4 to 6;
A and B are acid groups independently selected from the list consisting of sulfonic and carboxylic; m is 0 or 1; and l is 1;
C is a counterion selected from the list consisting of H+, NH+4, Na+, K+, Li+, Cs+, Ba2+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p); and p is 1, 2, 3, 4, 5 or 6;
wherein the organic compound comprises a bivalent group Xi, that covalently binds to two adjacent phenyl rings as in structural formula (Ia)
wherein X is selected independently from the group consisting of —SO2—, —O—, and —NH—, and i is the number of bivalent groups from 1 to (n−1);
and
wherein said organic layer is transparent for electromagnetic radiation in the visible spectral range.

### Claim 6 (depends on 5)

An anisotropic optical film according to claim 5, wherein said organic compound has the structural formula (II)

### Claim 7 (depends on 5)

An anisotropic optical film according to claim 5, wherein said organic compound comprises structural formula (III)

### Claim 8 (depends on 5)

An anisotropic optical film according to claim 5, wherein said organic compound comprises structural formula (IV):

### Claim 9 (depends on 5)

An anisotropic optical film according to claim 5, wherein said anisotropic film is insoluble in water and/or in water-miscible solvents.

### Claim 10 (depends on 5)

An anisotropic optical film according to claim 5, wherein said organic layer is a biaxial retardation layer possessing one refractive index (nz) in the normal direction to the layer and two refractive indices (nx and ny) corresponding to two mutually perpendicular directions in the plane of the layer.

### Claim 11 (depends on 10)

An anisotropic optical film according to claim 10, wherein the refractive indices nx, ny and nz obey the following condition: ny>nz>nx.

### Claim 12 (depends on 5)

An anisotropic optical film according to claim 5, wherein the organic layer is on a substrate made of a polymer or glass which is transparent for electromagnetic radiation in the visible spectral range.

### Claim 13 (depends on 5)

An anisotropic optical film according to claim 5, further comprising an additional transparent adhesive layer applied on top of the organic layer.

### Claim 14 (depends on 13)

An anisotropic optical film according to claim 13, further comprising a protective coating applied on the adhesive transparent layer.

### Claim 15 (depends on 5)

An anisotropic optical film according to claim 5 comprising two or more said organic layers, wherein the layers comprise different polycyclic organic compounds as defined by claim 5.

### Claim 16

A method of producing an anisotropic optical film on a substrate comprising the steps of
a) preparation of a solution of a polycyclic organic compound of the general structural formula (I) or any combination of such compounds of structural formula (I)
wherein
n is the number of phenyl rings from 4 to 6;
A and B are acid groups independently selected from the list consisting of sulfonic and carboxylic; m is 0 or 1; and l is 1;
C is a counterion selected from the list consisting of H+, NH+4, Na+, K+, Li+, Cs+, Ba2+, Ca2+, Mg2+, Sr2+, La3+, Zn2+, Zr4+, Ce3+, Y3+, Yb3+, Gd3+, and any combination thereof; k is the number of counterions necessary for compensation of the negative electric charge equal to (−p); and p is 1, 2, 3, 4, 5 or 6;
wherein the organic compound comprises a bivalent group Xi, that covalently binds to two adjacent phenyl rings as in structural formula (Ia)
wherein X is selected independently from the group consisting of —SO2—, —O—, and —NH—, and i is the number of bivalent groups from 1 to (n−1); and
wherein said organic compound is transparent for electromagnetic radiation in the visible spectral range,
b) application of a liquid layer of the solution onto the substrate,
c) application of an external alignment action upon the solution simultaneous with or after step b) but prior to step d), and
d) drying with the formation of a solid layer.

### Claim 17 (depends on 16)

A method according to claim 16, wherein said organic compound has the structural formula (II)

### Claim 18 (depends on 16)

A method according to claim 16, wherein said organic compound comprises structural formula (III)

### Claim 19 (depends on 16)

A method according to claim 16, wherein said organic compound comprises structural formula (IV):

### Claim 20 (depends on 16)

A method according to claim 16, wherein said solution is an aqueous solution comprising water and/or water-miscible solvents.

### Claim 21 (depends on 16)

A method according to claim 16, wherein the drying is executed in an airflow at an elevated temperature in the range from approximately 20 to 60 centigrade.

### Claim 22 (depends on 16)

A method according to claim 16, wherein said organic compound comprises sulfonic groups and said formed solid layer and is treated with a metal salt solution.

### Claim 23 (depends on 16)

A method according to claim 16, wherein the metal salt comprises a cation selected from the list consisting of Ba2+, Pb2+, and Sr2+ cations.

### Claim 24 (depends on 16)

A method according to claim 16, wherein said solution is a lyotropic liquid crystal solution.

### Claim 25 (depends on 16)

A method according to claim 16, wherein the sequence of technological operations of the application of the solution, the alignment action and the drying is repeated two or more times and each consequent solid layer is formed using the aqueous solution, this solution being either the same or different from that used in the previous cycle.