Liquid-crystalline medium
Liquid-crystalline (LC) media having positive dielectric anisotropy and liquid-crystal displays (LCDs) containing these media, especially displays addressed by an active matrix and in particular to LC displays of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB-FFS, SA-XB-FFS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA type.
1 . A liquid-crystalline medium, comprising
one or more compounds of formula I,
and
one or more compounds of the formula XXXa,
or
one or more compounds of the formula XXXIVa,
and having a positive dielectric anisotropy,
wherein
R 0 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
one of Y 1 and Y 2 is H, F or Cl, and the other one of Y 1 and Y 2 being different from H is F or Cl,
Y 5 is H or CH 3 , and
alkyl denotes a straight-chain alkyl radical having 1-6 C atoms.
2 . The liquid-crystalline medium according to claim 1 , wherein the one or more compounds of formula I are selected from compounds of the following formulae
wherein Y 5 is H or CH 3 .
3 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
wherein “alkyl” is C 1-6 -alkyl.
4 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
5 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
is
is
is
R 1 , R 2 are a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
R 3 has one of the meanings given for R 1 or X 1 ,
X 1 fluorinated alkyl or alkoxy with 1, 2 or 3 C atoms,
Z x , Z y are —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,
Z z is CH 2 O or a single bond,
Y 1 is O or S,
L 1-4 are H, F or Cl,
x, y are 0, 1 or 2, with x+y≤3, and
z is 0or 1,
wherein
in formula B the
group is optionally substituted by a methyl or methoxy group, and
wherein the compounds of formula Y contain at least one substituent L 1-4 that is F or Cl.
6 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compound of the following formulae
wherein
R 1 , R 2 are, each independently, a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
Z x , Z y are, each
independently, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,
L 1-2 are, each independently, H, F or Cl,
x, y are, each independently, 0, 1 or 2, with x+y≤3,
a denotes 1 or 2,
b denotes 0 or 1,
denotes
L 3 , L 4 denote, each independently, F or Cl.
7 . The liquid-crystalline medium according claim 1 , further comprising one or more compounds selected from compounds of the following formulae
wherein
R 1 , R 2 are, each independently, a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
L 1-2 are, each independently, H, F or Cl,
each, independently of one another, denote
in which
L 5 denotes F or Cl, and
L 6 denotes F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 .
8 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from the compounds of the following formulae
wherein
R 1 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
R 3 has one of the meanings given for R 1 or X 1 ,
X 1 fluorinated alkyl or alkoxy with 1, 2 or 3 C atoms,
Y 1 is O or S,
L 1-2 are, each independently, H, F or Cl.
9 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
wherein
R 1 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X 1 fluorinated alkyl or alkoxy with 1, 2 or 3 C atoms,
alkyl denotes a straight-chain alkyl radical having 1-6 C atoms, and
(O) denotes an oxygen atom or a single bond.
10 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
wherein
R 0 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X 0 is F, Cl, CN, SF 5 , SCN, NCS, or a halogenated alkyl radical or a halogenated alkoxy radical having 1 to 6 C atoms, or a halogenated alkenyl radical or a halogenated alkenyloxy radical having 2 to 6 C atoms,
Y 1-6 are, each independently, H or F, and
Y 0 is H or CH 3 .
11 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 0 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
Y 1-4 are each independently H, F or Cl, wherein at least one of Y 1 and Y 2 is F or Cl,
Y 5 is H or CH 3 ,
Z 0 denotes —C 2 H 4 —, —(CH 2 ) 4 —, —CH═CH—, —CF═CF—, —C 2 F 4 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCF 2 —,
and in formulae V and VI also a single bond,
and in formulae V and VIII also —CF 2 O—,
r denotes 0 or 1, and
s denotes 0 or 1.
12 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 0 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another.
13 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
X 0 is F, Cl, CN, SF 5 , SCN, NCS, or a halogenated alkyl radical or a halogenated alkoxy radical having 1 to 6 C atoms, or a halogenated alkenyl radical or a halogenated alkenyloxy radical having 2 to 6 C atoms,
L denotes H or F,
alkyl denotes C 1-6 -alkyl,
R′ denotes methyl, C 4-6 -alkyl or C 1-6 -alkoxy, wherein, if R′ is methyl or C 4-6 -alkyl, then alkyl in formula IX is not ethyl or propyl,
R″ denotes C 1-6 -alkyl, C 1-6 -alkoxy or C 2-6 -alkenyl, and
alkenyl and alkenyl* each, independently of one another, denote C 2-6 -alkenyl, and in formula X alkenyl denotes C 3-6 alkenyl.
14 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds of formula XIV
in which
R 1 and R 2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl or fluoroalkyl, each having 1 to 6 C atoms, or alkenyl having 2 to 6 C atoms.
15 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds of formula XVI
in which
R 1 , R 2 are a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and
L denotes H or F.
16 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 1 , R 2 are a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and
L denotes H or F.
17 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 0 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X 0 is F, Cl, CN, SF 5 , SCN, NCS, or a halogenated alkyl radical or a halogenated alkoxy radical having 1 to 6 C atoms, or a halogenated alkenyl radical or a halogenated alkenyloxy radical having 2 to 6 C atoms, and
Y 1-5 are, each independently, H or F.
18 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 1 is a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and
X 0 is F, Cl, CN, SF 5 , SCN, NCS, or a halogenated alkyl radical or a halogenated alkoxy radical having 1 to 6 C atoms, or a halogenated alkenyl radical or a halogenated alkenyloxy radical having 2 to 6 C atoms.
19 . The liquid-crystalline medium according to claim 1 , further comprising one or more compounds selected from compounds of the following formulae
in which
R 1 , R 2 are, each independently, a straight chain alkyl or alkoxy radical that is unsubstituted or halogenated and has 1 to 15 C atoms or a branched or cyclic alkyl or alkoxy radical that is unsubstituted or halogenated and has 3 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by
—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and
L denotes H or F.
20 . The liquid-crystalline medium according to claim 1 , further comprising one or more polymerizable compounds.
21 . The liquid-crystalline medium according to claim 1 , further comprising one or more polymerizable compounds, which are of formula M
R
a
-
B
1
-
(
Z
b
-
B
2
)
m
-
R
b
M
in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
R a and R b are P, P—Sp—, H, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, SF 5 or a straight-chain alkyl having 1 to 25 C atoms or a branched alkyl having 3 to 25 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 00 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which one or more H atoms may be replaced by F, Cl, Br, I, CN, P or P—Sp—,
where, if B 1 and/or B 2 contain a saturated C atom, R a and/or R b may also denote a radical which is spiro-linked to this saturated C atom,
wherein at least one of the radicals Ra and R b denotes or contains a group P or P—Sp—,
P is a polymerisable group,
Sp is a spacer group or a single bond,
B 1 and B 2 are an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may contain fused rings, and which is unsubstituted or mono- or polysubstituted by L,
Z b is —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S-, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 )n 1 —, —CH═CH—, —CF═CF—, —C═C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,
R 0 and R 00 denote H or alkyl having 1 to 12 C atoms,
m denotes 0, 1, 2, 3 or 4,
n1 denotes 1, 2, 3 or 4,
L is P, P—Sp—, OH, CH 2 OH, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or a straight-chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, or a branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which one or more H atoms may be replaced by F, Cl, P or P—Sp—,
Y 1 denotes halogen,
R x denotes P, P—Sp—, H, halogen, or a straight-chain alkyl having 1 to 25 C atoms, or a branched or cyclic alkyl having 3 to 25 C atoms, in which one or more non-adjacent CH 2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, or -O—CO-O- in such a way that O and/or S atoms are not linked directly to one another, and in which one or more H atoms may be replaced by F, Cl, P or P—Sp—, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.
22 . The liquid-crystalline medium according to claim 1 , further comprising one or more polymerizable compounds, wherein the polymerizable compounds are polymerized.
23 . A process for preparing the liquid-crystalline medium according to claim 1 , comprising mixing together one or more compounds of formula I and one or more compounds of the formula XXXa or
one or more compounds of the formula XXXIVa, and optionally one or more polymerizable compounds.
24 . A shutter glass, LC window or 3D application, comprising a liquid-crystalline medium according to claim 1 .
25 . An electro-optical liquid-crystal display containing the liquid-crystalline medium according to claim 1 .
26 . An electro-optical liquid-crystal display containing the liquid-crystalline medium according to claim 1 , wherein the display is a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA display.