# US 12,110,438 B2 · Liquid crystal composition containing dibenzo derivatives and liquid crystal display device

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- Number: US 12,110,438 B2
- Document ID: US12110438B2
- Status: Granted
- Kind: B2
- Application number: 18/012,683
- Filed: 2021-06-25
- Published: 2023-08-17
- Granted: 2024-10-08
- Earliest claimed: 2020-06-28
- Assignees: Jiangsu Hecheng Display Technology Co., Ltd.
- Applicants: Jiangsu Hecheng Display Technology Co., Ltd.
- Inventors: Di He; Wenquan Ding; Haibin Xu; Shuang Xu; Huijuan Dai; Lifang Yao
- Web page: https://patentgrep.com/patent/US12110438B2

## CPC

- C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings}
- C09K 19/3491: {having sulfur as hetero atom}
- C09K 19/3405: {the heterocyclic ring being a five-membered ring}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene}
- C09K 2019/3408: {Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems}
- G02F 1/134363: {for applying an electric field parallel to the substrate, i.e. in-plane switching [IPS]}
- G02F 1/13712: {the liquid crystal having negative dielectric anisotropy}
- 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

## Abstract

A liquid crystal composition containing dibenzo derivatives for use in a liquid crystal display device includes at least one compound of general formula I and at least one compound of general formula II.

## Claims

### Claim 1

A liquid crystal composition containing a dibenzo derivative, including at least one compound of general formula I and at least one compound of general formula II:
in which,
R represents —H, halogen, —CN, C1-12 linear alkyl, C3-12 branched alkyl,
one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl,
may be respectively and independently replaced by —CH—CH—, —C═C—, —O—, —S—, —CO—, —CO—O— or —O—CO—, one or at least two —H in the aforesaid groups may be respectively and independently substituted by —F or —Cl;
Rx represents —H, C1-12 linear alkyl, C3-12 branched alkyl, one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —CH—CH—, —C═C—, —O—, —S—, —CO—, —CO—O— or —O—CO—, one or at least two —H in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently substituted by —F or —Cl, Rx is attached to an arbitrary carbon atom in ring
R1 and R2 each independently represents C1-12 linear alkyl, C3-12 branched alkyl,
one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —CH—CH—, —C═C—, —O—, —CO—, —CO—O— or —O—CO—;
ring
represents
one or at least two single bond within the ring of the aforesaid groups may be replaced by double bond;
ring
represents
one or at least two —CH2— in
may be replaced by —O—, one or at most two single bond within the ring may be replaced by double bond; one or at least two —H in
may be substituted by —F or —Cl, one or at least two —CH═ within the ring may be replaced by —N═;
ring
represents
one or at least two —CH2— in
may be replaced by —O—, one or at most two single bond within the ring may be replaced by double bond; one or at least two —H in
may be substituted by —F or —Cl, one or at least two —CH═ within the ring may be replaced by —N═;
Z1 represents —(CH2)aO— or —(CH2)aS—, wherein a represents an integer of 0 to 7;
Z2 represents —O—, —S—, —CO—O—, —O—CO—, —CF2O—, —OCF2—, —CH2O—, —CH2S—, —OCH2—, —SCH2—, —CH2—, —CH2CH2—, —(CH2)4—, —CH═CH—CH2O—, —C2F4—, —CH2CF2—, —CF2CH2—, —CF=CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C≡C— or single bond;
Z3 represents single bond, —CO—O—, —O—CO—, —CH2O—, —OCH2—, —CH═CH—, —C≡C—, —CH2CH2—, —(CH2)4—, —CF2O—, —OCF2— or —CF2CF2—;
L1 and L2 each independently represents —F, —Cl, —CF3 or —CHF2;
X represents —CO—, —S— or —O—;
n represents 0, 1 or 2, wherein when n represents 2, ring
is same or different, Z2 is same or different;
m represents 0, 1 or 2, wherein when m represents 2, ring
is same or different, Z3 is same or different; and
at least one group of the following three groups: R1, ring
and Z3, contains at least one of —CH═CH— or —C≡C—.

### Claim 2 (depends on 1)

The liquid crystal composition according to claim 1, wherein n represents 0.

### Claim 3 (depends on 1)

The liquid crystal composition according to claim 1, wherein both L1 and L2 represent —F.

### Claim 4 (depends on 1)

The liquid crystal composition according to claim 1,
wherein X represents —O— or —S—; and
further wherein:
a represents an integer of 0-3; or
R represents C1-12 linear alkyl, C3-12 branched alkyl, or one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —O— or —S—; or
Rx represents —H, C1-12 linear alkyl, C3-12 branched alkyl; or
the liquid crystal composition contains at least one compound of general formula I in which X represents —O—; or
the liquid crystal composition contains at least one compound of general formula I in which X represents —O— and at least one compound of general formula I in which X represents —S—.

### Claim 5 (depends on 1)

The liquid crystal composition according to claim 1, wherein the compound of general formula I comprises 0.1-40% of the total weight of the liquid crystal composition.

### Claim 6 (depends on 1)

The liquid crystal composition according to claim 1,
wherein the compound of general formula II meets at least one of following conditions a), b), or c):
a) R1 represents C2-10 alkenyl or alkenoxy;
b) when m represents 1 or 2, at least one ring
represents
c) when m represents 1 or 2, at least one Z3 represents —CH═CH— or —C≡C—.

### Claim 7 (depends on 1)

The liquid crystal composition according to claim 1, wherein the compound of general formula II comprises 0.1-50% of the total weight of the liquid crystal composition.

### Claim 8 (depends on 1)

The liquid crystal composition according to claim 1,
wherein the liquid crystal composition further includes one or at least two compound of general formula M
in which,
RM1 and RM2 each independently represents C1-12 linear alkyl, C3-12 branched alkyl,
one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—;
ring
ring
and ring
each independently represents
one or at least two —CH2— in
may be replaced by —O—, at most one —H in
may be substituted by halogen;
ZM1 and ZM2 each independently represents single bond, —CO—O—, —O—CO—, —CH2O—, —OCH2—, —CH═CH—, —C≡C—, —CH2CH2—, —(CH2)4—, —CF2O—, —OCF2— or —CF2CF2—;
nM1 represents 0, 1, 2 or 3, wherein when nM1=2 or 3, ring
is same or different, ZM2 is same or different.

### Claim 9 (depends on 1)

The liquid crystal composition according to claim 1, wherein the liquid crystal composition further includes one or at least two compound of general formula N
in which,
RN1 and RN2 each independently represents C1-12 linear alkyl, C3-12 branched alkyl,
one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —O—, —CO—, —CO—O— or —O—CO—, one or at least two —H in the C1-12 linear alkyl, C3-12 branched alkyl,
may be respectively and independently substituted by —F or —Cl;
ring
or ring
each independently represents
one or at least two —CH2— in
may be replaced by —O—; one or at least two —H in
may be substituted by —F or —Cl, one or at least two —CH═ within the ring may be replaced by —N═;
ZN1 and ZN2 each independently represents single bond, —CO—O—, —O—CO—, —CH2O—, —OCH2—, —CH2CH2—, —(CH2)4—, —CF2O—, —OCF2— or —CF2CF2—;
LN1 and LN2 each independently represents —H or methyl;
nN1 represents 0, 1, 2 or 3, nN2 represents 0 or 1, and 0≤nN1+nN2≤3, wherein when nN1=2 or 3, ring
is same or different, ZN1 is same or different.

### Claim 10 (depends on 1)

A liquid crystal display device including the liquid crystal composition of claim 1;
wherein the liquid crystal display device is an IPS mode liquid crystal display device, an FFS mode liquid crystal display device or a VA mode liquid crystal display device.

### Claim 11 (depends on 6)

The liquid crystal composition according to claim 6,
wherein the compound of general formula II is selected from a group consisting of the following compounds:
in which,
Ralkenyl represents C2-7 alkenyl; and
R1 and R2 each independently represents C1-10 linear alkyl or alkoxy, or C2-10 linear alkenyl or alkenoxy.

### Claim 12 (depends on 8)

The liquid crystal composition according to claim 8,
wherein the compound of general formula M is selected from a group consisting of the following compounds:
in which,
RM1 and RM2 each independently represents C1-12 linear alkyl, C3-12 branched alkyl, or one or at least two nonadjacent —CH2— in the C1-12 linear alkyl, C3-12 branched alkyl may be respectively and independently replaced by —CH═CH— or —O—.

### Claim 13 (depends on 12)

The liquid crystal composition according to claim 12,
wherein:
RM1 and RM2 each independently represents C1-10 linear alkyl, C2-10 linear alkenyl or C1-9 linear alkoxy; or
the liquid crystal composition includes one or at least two compound of general formula M1 in which RM1 and/or RM2 is n-propyl.

### Claim 14 (depends on 9)

The liquid crystal composition according to claim 9,
wherein the compound of general formula N is selected from a group consisting of the following compounds:
in which, RN1 represents C1-5 linear alkyl, C3-15 branched alkyl, RN2 represents C1-4 linear alkyl, C3-14 branched alkoxy.