Document a4zoBX5OgZoVRVqdg1G01Z8ea
"19)
9 CE
[I
an EP2811003 A1
(12)
EUROPEAN PATENT APPLICATION
published in accordance with Art. 153(4) EPC
43) DToait2e20pu4bicaBtuiolna:n 201450
(21) Application number: 12867129.4
51) mCao Taz Coo Tota SCOo9rK tse 19130 220625)
Ccoo o fo2mmupm
CO9K 1913422020
2 Dee atiliog SRR
(86) PInotTerunaptaioOna2lnaRppAlDicSa2tion number:
(87) WIntOer2na0t1i3on1a1l4p7u8bl0ic(a0t8i.o0n6n.u2m0b1e3rG:azete 2013132)
(84) LGDeRAsiHTgRnaHBtUEedI5EC0oInGtSrHIacTCtiYLnIgGL2StTaOtLFesU:DLKVMEEGHESKFMITFNRLGNBG||(72)+ YInAhvNeinAtrIorTosa:skhaiyoshi
BPDAeLsNiPgETnaRtOedRESxtSaEnsSoInSSKaiSsM:TR (30) ror: 03022012 0p012021840
(71) ANppGlicCaonrtsp:oration
CRehhAiibnTaaIr2aO9s0h-Ni8o5r5k1ai(JsP)u. + CWhAiEbDaA2T0a.k5e5o1 (UP) chiarsahi
Chiba 290-8551 (JP)
Chiyoda-ku
+ TITooNkkGyypooe11t0r00o0-c08h01e00m45ic(OaJPPl)).Corporation
(74) Representative: Thurston, Joanna et al
LWMiootnhrdeoornsLS&oEnR1doo2gne4r0Rsi(vL6eL8rPs)ide
(54) DLIIQSUPILDACYREYLSETMAELNCTOMPOUND,LIQUID CRYSTAL COMPOASNDILITQUIIDCORYNST,AL
o(6n7)SaAinsat leatusoparnoevbiodf cahfaaruactcerriscioascuocmshpaossi iPhmumamxaimmaprteamtperreahrles nofeamnaemhaats,paassem vos.w CIsooyv.ort, a aageoseppiontearemslasnce,aaiagvhohdoeaecpbilcayyn.to 2UrlitnecyGaaanlcdomanpilhioSnaavwy loossuolsleopaolvrdeen. eedewnin lGeoaress aealaSrarpee nneoagla.e
vfoelaagndehokdfionr.gra, alargeconastat,a ng sens ramhasopthoasne asnad cldoanyatsalpeccnompcoosmopnoutnhadtrhaausnga aspleglotaceomcpiocunad hsaviangkaoosomapraytlclomvpos4necanstoencsdonyda negmponeghntianmd muay ctoenmapneasstpeocri8cromgpouendcakv. pwaabsopy wiaghosocomopetia on. T
<38 =
~ a w
oor -- i iner entra e enn sos euis or
Ee 0CO [0002] Ina liquid SeyEcs1)tL ot soe nnne e 0o es nritsoorness crystal display device, a classification based on an operating mode for liquid crystals includes a 0 nSsE lnTus nn L,ms eaSeosserte siegsofnnspnpnesi(A7caemteftoonnSaeesei0si)ot
[ro [Emam Jommomomsamons .B m SE raam mE eT Ara vrT isa 1ea eorsee hysssaunted oTmTe C rs Eoe iiSrsr Tmmh aerrgSeiryn [0003] The devices include a liquid crystal composition having suitable characteristics. The liquid crystal composition
.[[75os sSCmornmaanomeenns mae v5o | o Cre e s
[ss 1 Large specific resistance
Large voltage holding ratio and large contrast ratio
" iargon cr RGR 0Co ydot ra tpa ss A Bt mas er, [0004] An oplical anisotropy of the composition relates 10 a conlrast ratio in the device. A product (an x d) of the
.
ep 2011 003 A1 A radia taingecrlooky MageAdesA tivaatpgacposI in aodA eNsOioatoA n restos 5 cmeotgmptgostsoiaeotnnaeNoasmioaeatrrsgadsodaesocleoenioeesmiaenm,ha osemoopoatoearnstohaovnsgalitathoBsteoeuassnaDn WtSd0oegesm opemrdeodaa aohvmeepecnormsepaoolsilhoyn htohadtavevipasesvs6eanvansnslhaoornheesdlrotinc1He.a:ksSuoicohehaoHoohfohfsooirrepaarvodlooafdmootpreaeandtsaoGeio,inSraamnye 0 nates yaplo, kdsve ovon and on. Fo10m0ap05om]niaAoncoonmapmorsyiitiaonotshaivovienig ea eposoieE tivuecdGieleucatrailceannsiasrodtkrooppyisis uoesenddfroore ranonAAMsdeSoveivceenahnaivinggttohoeegTsNSmomodte.oeBOnyTt0h0e 15 omordee.s oExarn slohe. ks yl oposton avn 1 PSE di atopy we acne PanHor chao Lst Fanti
[0006] PatentliteratureNo. 1: JP 2007-50348A7.
5
ln. Sgr esp [0007] A desirable
AM
ns
E ovens ov lr asE Tm, aera Sages oa device has characteristics such as a wide temperature range in which a device
can be used,
Sonoeeion
YesaosNaidsaapovtatamaenadnaarb eagomnasmcoemicnth.easorsloagyspechresHanon Ohoi drove
= Summary of monton
ve
= [0ak00n8e]ilmOpnaeltoof tshaenaiammcs okfe.thegrinsvenatioencris aaleiqmuidSaaciry.wstfamlTcmooSmpmossriteicopantsoaetmissstfyaianang ,abttmlelashtieonSet;aaofsbchhabrsoaocematearllisstHlicosrssmulch
TAeivsanrdntgaitmsai.tsocbroaomnopoafasa7h0aasnatgisla,rteApltrotanotaioaymlas.1S0olyddllpdcsomtaicnoscmopoaopsyo,ranhh uSanasycdooampoovs.
BO
A inHS OR
Sotto to Poem
E1008h) TT romentonsonemsalutesasco mprstio ah hase] andea s aiasca nasapond
GSeenmtovoemnhue pnososfccoommpoptaionnions tla )0s soca componet. nd caren Kcr
#
x3
x!
.
R!
Fs
0]
m
4
2
s
oo D2)w n Sm EE E EEEe m r E e independently a single bond, ethylenoer carbonyloxy; X', X2, X and X* are independently hydrogenorfluorine; and m |g E y EE EFmE FC a E E C E C E E E C E EE E C E E Bi T rREEEEeeEE ErE mEE na m m m mmiET E e E h E E E T m-- oe en m e e m m e e p e e e m-- e a eeE E e E E s E E et--r e e a e a eRa ee nE--iae [0010] Anadvantageoftheinventionisaliquidcrystalcompositionsatisfyingatleastoneofcharacteristicssuchas.
cpzon amaat AARONaE LCT a emes ee hes [0014] The invention includes the items described below.
[0015] Item 1. A liquid crystal composition that hasa nematic phase and contains at least one compound selected
x3
x!
R1
Fs
1)
m
x4
x?
Y
R2.
71
R3
n
srEEhEeR l W 2 on Ra smhRoArtu rtets ts re oo,se `wherein, R! is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carobroalknensyl having 2 to 12 carbons, and RZ
On.
on
.
FF
Y
.
. we (O-(pron
i)
F
.
EP 2 811 003 Al
FF
,
wrenCF
5
F
010
F
F
CF
i 155
F
. OO(rom
20
CF
F
=25
FFF
. CF3
30
FF
CF3
35
FF
40
i CF
45
CF3
*
F
50
CF3
55
6
((11--55))
(1-6)
on(1-7)
(1-8) (1-9) (1-10) (1-11) (1-12)
:
FF
F
"
F FF
"
F
F
F
. Rl
Fa
F
(1-16)
LOO F F om
"
FFF
"
F
FF
FF
10017) Item3. Theliquidcrystal composition accortdoiintegm 1,whereinthe first componeisnatt leastonecompound
:
[0019] item 5. The liquid crystal composition according to any one of items 1 lo 4, wherein the second component is.
.
.
R?
3
@7
F
.
:
Ep 2011003 A1
sO R2. OO 3
@12)
F
5 T`[2w0hc2ear0er]ibno,ntsR,o2moafndakRT?ahanrue ivdnideype2sn1dlaen1tc2loymtaplhoksyoiltnhiaovninawgic1ctheot1r2acoasrfbaoannse,o1a,flwkrohxaeyrghaeevihng p1staao cc1oe2ndcacbroybmopfnosun,eianl.tkenylahatviongn2eto Compound Sled rom he grofoampuounpd preset formula 2-1) secorang oem 5 Compound om ha fou 10021] Item 7. The liquid crystal ocofGmpaosmiptiooun NacrcoerpdrisnagTteoditoeymo1, lwher2ei-n3t)he6s5ec0ongd coomepon.ent is at least one. la1e0a0ad2t2n]oneeiccteoommpm8.opuTnhusesslilequliededccry5s1t70amlmc0o3mporusitpoionofaGccocooBrmdoiupngnestno piatresmpa1rr, iweehedsrebiyynothmeaasec(on7(d2)1caocamscprosndrenangntgois0ea fmmo.im xtaoudfraaett
5000i21056027e)3%] bIryHtaawegmmee9.i10,.T3hTa%elboisyquhioadocknrRyhsytas1lt0lc2ao5mo%pWmobpseiyotgswitoofinoahnhccacornkdediasnrgatnoykaantoyaoncnneoyomsofpneioectsooetnfnmfs.smo1s1m0.8o,1 wn(h0ee,rieienntharereraacnotofgritenhoeiofnf5igrs%tacoeomypswonooennhet Compound Slced ome Group of cpu eeSSaIad oy or 38.8 Id Component:
PB R4
x5
Z2
Y1
3)
hTearcoanc,heRreisyaonel. 1ha4vminegn1i10o12nc.toiootn-,1pankoeenyihaavnisng.1J10 1r2 t1o4npsraoyfearlsk,er 5h-a0ving 2110412hcaanrgtoenrs.ng133C's 40 ZoCx3aonaer-r2ss,5o-dniylX, taetnrdah8ydraospyrmadn-o2p,oSd-dainylloyr on en: pyrimidine-2, 5-diyl: ZY21is afsaincgele,baonrdi, ndifluoromet mao: and 1 hyleneoxy, ethylene 1or
C1o6m0p25ouned sml11e. dToomb(dhe fcoyusstlocfocmopmopsioounnaTcieedrinognfo bfyoom r10,lwh(r3s.n0trhe tnh (c3o26m3pan a ast one
r{Ya
@1)
"
=
rR))
(33)
.
(YO OYe
:
F
i .
ROO oC .
(36)
.
F
~O-O%F SF
on
w
OCF;
"
F
"
R
(48)
F
Q
"
F
a "
0
. (OCJ R*
(3-10)
O04 a
en
-
F
F
.
"O-O-Oepzoraust on
wO-O-Cor
13)
g
: wc O-O-Cor
(3-14)
w
F
Fr
= R
F
oF
(3-15)
"
FoF
5
CFs
FoF r
ve
& ce OF ve
"
:
0 R*
F
F
F
(3-20)
xo
x7
F
x5
x10 \e
Y
xe
Y
F
x
x12
x10 \e
Y
xe
wo
mH x1
x8
FF
Xx
ew
x12
10
Y
i"
x8 x8
x? x7
ri 0,
F F x8
0
O
v1
x10
x8
=
xe
(3-24)
LT tors To
}
EP 2811003 A1
`0c0o2m6p)ountdesmele12c.tedThfeomligtuhide gcrystraolfcocoommpuposoiulpnodnsarcecporredsienngtetdo blyefmor1m0u,lwah(e3r-e1i4n) atchceorthciirndgcoomtpeomne1n1.t i at least one
`1c00o2m7p)ountdesmele1c3t.edThfeomliqtuhide gcrryosutpalofcocmopmopsoiuinodnsarcecporredsienngtetdo beymfo1r0m, awh(e3r-e1i5n) atchceortdhirndgctoomtpoene1n1.t i at least one.
5 [0028] Hem 14. The liquid crystal composiion accordingto lem 10, wherein the third component is at least one
`compound selected fom the group of compounds represented by formula (3-17) according to te 11.
`0c0o2m8p)ountdesmele1c5.tedThfeomlithue gcrryosutpalofcocmopmopsoiulnodnsarcecporredsienngtetdo blyefmor1m0u,lwah(e3r-e2i1n) atchceorthdiirndgctoomtpoene1n1.t i at least one
10. c0o0m3p0)ountdosmele1c6.tedThferolm ithue gcrryosutpalofcocmopmopsoiulnodnsarcecporredsienngtetdo blyefmor1m0u,lwah(e3r-e2i2n) atchceorthdiirndgctoomfpeomne1n1.t i at least one
`1c0o0m31p)onentteimsn17.thTehreanlgieqouifd 5cr%ysbtyalweciomgphots0iti6o5n%acbcyowrediignhgttboaasneyd oonneth oftloteamlswe1i0ghttoo1f6t,hewhueiredincraysatatlocoomfpotshiettihoinr.d
o10fa032n)emattiecmp1h8a.sTe his 7li0qu"iCd corryhsitgahlecro,mapnosoipttiiocnalaacnciosrdaitnogpy (a2n5yCo)naetoafwlaevemlse1ng1t0h17o,f5w8he9reniannoammeatexrismuism0.t0e7mpoerrmaotruer.e
#5 a1n0d03a3d]ieletcetmric19.anAisoqluriodpycr(y2s5talC)dialspalafyrdeeqvuiecnecyinoclf1udking Htshe2zqouridmocrrey.stal composiion according to any one of tems 1
oa, 10034)
tom 20. The liquid crystal splay device accorcing oem 19, wherein an operating moidntehe liquid crystal
mdiosdpleayindetvheicleiqiusidacTryNstmaolddei,spaanyEdeCvBicmeodise,ananacOtiCveBmmaadrex,maondeP.S mode, a PSA mode or an FPA mode, and a ving
10035) 10036]
Tehmeti.nveUnsteioonlftuhretlhieqruiidnccrlyusdteasl tchoempfootloiwoinngaclceomrsd:in(g1l)otahneycoonmepcofsitteomns,11fu0rt1h8ericnoanltaiiqnuinigdcarnyospttiacalldldyiisaccptaeiyv.e
`compound; (2) the composilon, uriher containing an additive suchasan antixidant, an ulraviole ight absorber, an
25 a(4n)taidoeaviinceg aignecnltu,dianpgotlhyemecroimzpaobslieiocno,mapnodunhdaanvdaiaTnpNogl,ymEeCrBiz,atOiCoBn,aIlPrS,;FF(3S)aornPASMAdemvoidcee;in5)claudirnagntshmeiscsoimvpeosdietvoirc:e
including the composition: (6) useofthe compositionas a composition having the nemaic phase; and (7) use as an
optical 10037)
aTchteivecocmopmopsoistiitoinonobfytaheddiinnvegnttihoenopwiilcablleyeaxcptliavienceodmnpotuhnedortdoetrhedecsocmrpiobseitdiobne.low.
First,
a
constlutn
of
the
`component compounds i the composilwoinlbe explained. Second, main characterisotfitchsecomponentcompound
anda main efectof the compound on the composition wil beexplained. Thid, a combionfcaomtpoineontns in the
`composition, a preferred raotfthoe component compounds and the basi thereofwil be explained. Fourth, a preferred
`embodimenthtecomponentcompounds wilbe explained. Fifth, specific examples of thecomponentcompounds will
btheeshcoowmnp.onSeixntth,caonmpadoduinidvse twhialtbmoaeyxpbleaimniexde.dwLiatsh,thaecnoampppiocsatiotniwoofintlhbeeecxopmlpaoisnietdo.nSweivlenbteh,exmplaeinedt.fohrsynothedsizisng
25 t[h0e03i8n]ventFiirosnti,sthcelacsosnisftiietdutnitoon cofomthpeosciotmpiooAnneanntdccoommppoousnidtsoninB.theCocmopmopsoistiioonAnwimlabyefeuxtphlearinceodn.taTihneacnoympootsheirtiuoniodf
c(1r)y,stcaolmcpoomupnoudn(d2,)tahnedadcdoitmipvoe,uanndi(m3p)u.ri"tAynoyrotthheirkleiqiunidadcdriysttiaoln cootmhpeoluinqudi"dcrmyesatnalscaomlipqouiudncdryssetlaelccteodmpfrooumncdodmipfoeruenndt
4 fofofmutchoermpaoudndj(1)tu,hceocshmaprtaocutinerdins(t2i)gcas.ndTcheoamdpdoituinvde (i3). nSucchhaelocpotuimcpadolulyneadctiissvemecodmpwoiutnhdt,hethceomapnosiictxioindfartnht,eheutpruarvpiolseet
iignhctluadbessorabecro,mpadoyuen,dtmhiexaendinoaaripnrgocaegsesns,ucthheapsolpyrmeeprairzaatbiloen cofomthpeocuonmdpaonndentthecpoomlpyomeurnidzsa.tiEonveinniailnotrh.eTchaeseimwphueirye
the compound is liquid crystalline, the compound i classified as the impuriy herein
4 (130).03A8l)ermCoemsposseintiiaonl"8mceonasnissttshtestsheenctoamlpyoosfictoiomnpmoaunydcsonstealectthedafdrdoimticvoemapnodutnhdei(1m)p,ucroym,pobuutnddoe(2s)naontdcocnotmaipnouannyd
plioqsutidiocnryAstahlasc.omCopmopuonsditdiiofenrBenitsfpormefetrhreecdotmopcooumnpdoss.itCioomnpoAsiintviioenwBofhacsoastsmreadlulcetrionnu.mbCeormopofsictoimopnanAenistsprtehfaenrrceodmt-o
`composition 8 in view of possibilty of further adjusting physical properties by mixinganyother uid crystal compound.
c1h0a0r4a0c)teriSsetciocnsdo,f tthhee cmoamipnoscihtaironacwtilerbieseotxfpitlchasienecdo.mpTohneenmtaicnomcphoaurnadcstaenrdistohtfeihmcaesincoemffpeoctnsenf!thceomcpoomupndosuanrdoesnsutmh.e
marized in Table 2 on the basis of advantageous effects of the invention. In Table 2, @ symbol L stands for large" or
"high." a symbol M stands for "medium." and a symbol S stands or "smal" or "low The symbols, M andSrepresent
a cassifcation based on a quatative comparison among the component compounds, and 0 (zero) means "a value is
neary zero"
"
:
[Vom|S mrtpCos mpeound_(i2)|| Csormpuounsid (3])
[ [or s|| t W+n|m s || e|s m] wr i |
a re npn on am [0041] Upon mixing the component compounds with the composition, the main effectsof the component compounds
5 perature and decreases the viscosity. Compound (3) increases the maximum temperature and increases the dielectric
[0042] Third, the combinationofcomponents in thecomposition, the preferred ratio of the componentcompounds and
re n ee p rr r er e21 third component. The preferred combination of the components in the composition includes the combination of the first a oem eonrmse cseomees rss, [0043] A preferred ratio ofthe first componentis about 3% by weight or more for increasing the dielectric anisotropy,
[0044] A preferred ratioofthe second component is about 25% byweightor more for increasing the maximum tem
ee or e rearet r o 3 35% byweight to about 75% by weight. bFEeedeie SE Us , Ts 35 [0046] Fourth, the preferred embofo thed compi onem ntcoe mpoun ndst will be explained. R' and R* are independently
EEEe a esNramTeky `having 1to 12 carbons for increasing the stabilittoy ultravioletlightor the stability to heat. Rand R?are independently
[0047] Preferred alkylis methyl, ethyl, propyl, butyl, pentyl, hexyl, hepotroyctyll. Furtherpreferredalkylisethyl, propyl,
[0048] Preferred aliksmoetxhoxyy, ethoxy, ,propoxy, butoxy, pentyloxy, hexyorlheoptyxloxyy. Further preferred alkoxy
10049] Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3 `pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl. Further preferred alkenyl is vinyl, 1-
ee tn ee ne hexenyl, 3-pentenyl, and 3-hexenyl for decreasing the viscosity. Cis is preferred in the alkenyl such as 2-butenyl, 2m TE iB e eetns attmeyL r merlm y e ns teaoy nosoe r ean) [0051] Alkyldoesnot includecyclic alkyl. Alkoxy does not includecyclic alkoxy. Alkenyl does not includecyclic alkenyl.
[0052] RiAnangd ring B are independently 1.4-cyclohexylene, 1.4-phenylene, 2-fluoro-1.4-phenylene, 3-fluoro-1,4-
"
P2811 003 At 1SniennyglnnAogsrBG2sr15, &.cfy4opcrhera-yeonhr1dee,ceTrewaonsionfigaroervaiynscfoisnsgy,Aahnnc &nipsha2oyria3nmaoyrbiencerneatsiiangl fheeorpeantl.anProottye.a R1.3I5N0GxaC1-42-5y.cdnye,txryaahnyeo.p1yraphne2n.y5ie-ndsy2|fuoofrpoy-1i&npeh2a5nd,.3Tcurooof-a1rphieannyinegn,G3.w5hdefnlupciso-2,1 o6srh4nymiaeyneb,s 5 eInncrteaaslinagihfeiraenptc.laPrnesfoerleody1, a0nd131..4c5yc1on4eyisenhfoar nrrsaaysinageannseinsmg ancuiarcaaten,s.14shenyans P[0u05t3]as2121isa sisgilngolebobno,daotryldencoreoarscianrgbtohnyivaancyosTlwyo, oafndarcrarabyo2n1yownheonr incr2eaosrin3gmtahye bmoadxeintmalempfearbeen, 0 i2o2o'nsicaalsoirngierboond., dPrieuloarroemdat2t2y1asn.alceye, abtohnloonr doreecaasribnogxnye.viTswcoosotyf.aarnidraArlyc2omwehtenanpeion2.y foot c4remaasyinbgo ne delete ansotopy
10054] X', X2, X3, X4, X5, XE, X7, XB, X, X19, X'! and X'2 are independently hydroorfgluoerinne. Preferred X', X2,
6 nX[30e,05Xv54i],coXs5tY,yX.i6, fXTu,oXr8i,,XOc,hXi1r9i,nX,1f1uocrrX'o2imseftlhuoorniynoe fforuionrcrcemaseitngy.therdiaelerctericYa'nissoltruonpye, afnorddheycdrreoagseinngfotredevcirceoasstiyn.g e[m0p0e5r6]aturTeh.en, mf 1.2 or 3. Prefered m 1 or decreasing h vio, and 2 or 3 for rsasing te maximum
20 stabi to uravolt ight o heat. [0057] Further, ni1s, 203r. Preferred nis 1 fordecreasing the viscosiatnyd,3forinctr he meaxa imus mtei mpernatug re. [0058] Further, pis 1, 2,3 or 4. Preferredpis 2for increasing the maximum temperature, and 3 for increasing the
b[1e02l0co5w9,]a_RrSFibafotlrho,kaytkhnleoshsnpaevcihinafgvici1ne1gx0a1m1p12lec1sa2rbcofaorntbshoenocsro.amlpRko7ennayenlndhtaRvciaongrmp2no1dup1ne2cwdnaidsrlebbonentsys,hoaawnni.dghRItn citshheanpnrpeaeferlrdreehdnactvoymipao1lu1yndh12adevcsiacgrrbi1obne0sd
or straight-chain alkenyl having 2 to 12 carbons. RY is independently straight-chain alkyl having 1 to 12 carbons.
25 iP[n0rc0ll6u0ad]eesscPrcoeomfmpeproroueundndcd(o12m6)p.o1nu)lnaodntde(1s)cocimnocpmlopuudoneusdncd(o1(m12p-7o11u1.)ndtPoa(1rc-to1i-m1up)aortuyoncdroe(m2fp1eo3.ru1ns)d.c(oF1m-up1-o1eu)n.drFe(u1er)trhneecrdcpcreeosfmerpcrooemdupncoou(mn2p)docu(n1u6de-(1s1.) 5 2pp-ro1e1fu)e,nre2ddc)ocnmocplmoupudoenusdncd(o2(-m35p)-1oc)u,nlcdoe(m2sp1-oc1u)on,mdpP(o2ru-n7od-f(13c5c.o1om)pm.opcuoonmdupn(o2ud-n1(d031i(n)6c-ad1ens)d,ccocomompmpopouounundndd32-311--1-4)-11t,)oc,oPcmaopmropuiontudny(d2p(43o--f11r5,r1)e,Fdurcctoohmem-r
B3-o1u4n1d),(31c6o.m1p).oucnodmp(o3u5-n1d)(,3c21o-m1p)ouanndd (c3o.m2p1o1u)nadnd(3c22o.m1p).ouPnda(r3.c22s1preered compound 3) inca compound
# OreFn
a
F
FF
redyer,
F
v
1
(1-3-1)
P2811 003 41
FF
,
we -(gron
F
"= O-O-FCreF n
"
F
F
. e-em
F
-
FFF
royHom
F
FF
"
redHH)
.
F
red{hom
"
F
wer
(1-5-1)
re
(74)
(1-8-1)
(1-101) (1-111) (1-12-1)
:
EP 2 811 003 Al
CF3
5
FF
10
CF3
F
"15
FF F
CF3
"20
F
FF
25
. CF3
30
oOF F
35 CF
"
FFF
40
CF
45
50
ROO
F
QeF CF
FF
55
6
.17
(1-13-1) (1-14-1)
(1-15-1)
(1-16-1)
em(1-17-1)
(1-18-1)
ee(1-19-1)
(2-1-1)
Ep 2811003 a1
Rw RL) we Ry)coo(yre
PM
(2-2-1) (2-3-1) (2-4-1)
.
CoO
(2-7-1)
F
- RAO
(281)
F
*
R'7.Oreo pLHse
(2-10-1)
R OOOn
@-12-1)
Ep 281100a31 F
O 7 OOO R
rd po
RLOF
RL)
RL {HHYa
F
v
"
Fe F
-
"
FF (OO
--~ ocr,
" 9. OO
F
F
0
v
wo
ey
(3-1-1)
32-1)
(3-3-1)
(34-1)
37-1)
6
Ep200103 141 F
}
woe
F
P
rH)-oFf
v
F
"OO
-
F
FF wO-O-(r
F
u
F
OE F
F
-
F
} OE - OCF
F v
(310-1)
311-1)
(313-1) (3-14-1)
(3-151)
(3-161)
R?:
`
0
i
: Fe F
F
F
F
FF
(3-18-1)
. R
F
F
RS
g F F
F
Oo
F
F Fc
- R
EF
o
F
F
"
=
OOCE: Ai RE >
F Fc A)
.
(3-21-1) (3-21-2) (3-21-3) (3-22-1)
Ep2011 00431
CeO ona F F Fe F
1
7 \ 20
F
h RY
FF Fe F
FF
F
v
(323-1)
I" 2
d
-
F Fe Fo
oF
(3-241)
CC[p0o0im6cp1ao]luynaSdciixatvnhe,d catheopadadmimteirvpeahaothtanaot nmulaiyonbermhiTxahed apwtivtcihalathyevactoeimvperocsoitmtip.oonuwn1idlhbe.miexxapeldiaiinctedah. mhSenuccghoamagnpenaotds.diitipfveerlivnecmlepudreosasatehee Br11r0 rcompohuned (5 A rheftetd oatoisiogoptiacoalkaocneecoBmapoiunnds schootta 5 wATegOaess.pAornvds
Prfaredratars nn 1303 f abou D1. by weight 0 abot 2%by wet.
HHCyC CHa
HC
CH,
"
Q
5
@1
Ceti 0
-
[
o
\oA)oO0pio "482
CHy
HOOOneTM
N
HC
2
ep2om ansar
re
.
CaHy
o.C- eti (4-4)
CH
0
Cott
"
F on 9) CeHis CHs
. Fo[0062] The antioxidant is mixed with peA the composition for the purpose of preventing a decrease in specific resistance
(CHs)s
CHa
OH
(5)
(CHs)s
. [0063] Preferred examples of the antioxidant include compound (5) where ris an integer from 1 to 9. In compound ee FD oee be mt epose t ne oI rh es a vA etoe r oleOOo BaoL nronmai aA Bmommratestaasins [0064] Preferred examples of the ultraviolet ight absorber include a benzophenone derivative, a benzoate derivative ie aro Looe o e so plon t papnt er t savs e ches co toon 1, [0065] A dichroic dye such as an azo dye or an anthraquinodynee is mixed with the composition to be adapted for a
e D rD a e reteeT gno vs At enpaneo maveSeteontAE rSeO eht mons earag,ien SfPoS coonanApitornRoerpe.eAopaynoeentpthtoy esSeoepsuSlpka pc.ei ie aepos nremtepL e s epa StoO 45 device havinag guest host (GH) mode. A preferred ratio of the dye is in the rangeof about 0.01%byweightto about
oor eee rOaDs Ae sR emi Sh Sel (registered trademark; BASF) or Darocure 1173 (registered trademark; BASF), each being the photopolymerization L ee S e amSI e Le e E SA s E)O OE Ne TA CTeooE oerrmt e ecsS oSmA anissEr yim sncSsAine oarrToess s Cr Gaoa enmogS tent snens etm msrnne [0068] Any compounds whose synthetic methods are not described above can be prepared according to the methods. I fi m or mers eStCs)CSnTTn rTeesetorerroE ) sesarOn inrh eoka eySenn rei sSreeopbe [0069] Last,theapploifthceca omptosiitioonwn illbeexplained.Thecompositoiftohne invention mainly hasa minimum PR pa tAotT os ssere Tee ee esgnpoAneTp Ea erSeploAo ensA AbA rsreoenrrosss [0070] The composition can be used for the AM device. The composition can also be used for a PM device. The eOOe T T c0aTT1m)nepTrb hee nscrropsesome aatvcpns eerrireirse sndi dareaascrn coTne ,tga TeoTnhnantever bsaedoenednonh n eeeenaneeniss es rmstesienPooerergmiesceieiynoerni,t)1s1 45 measurement, according lo an extrapolation method: (extrapolated value) = {(measured value of a sample for meas-
urement) - 0. 85 x (measured value of base liquid crystals)/} 0.15. When a smectic phase (or crystals) precipitated at
Tr arate (10% by weight: 90%byweight), (5% by weight: 95% by weight) and (1%by weight: 99%byweight). Values of a L[Nm G ener a Sl iy Essays [0072] Components of the base liquid crystals were as described below. Aratio of each component is expressed in
CoH ~
oN
24%
u
pm p soeoanrOs o nn--eoCnr O-nnrooe nneox [0073] Characteristics were measured according to the methods described below. Moosftthe methods are applied r B E E SEE r e na [0074] Maximum temperature of a nematic phase (NI; C): A sample was placed on a hot plate in a melting point i EI ErneN a e e E [0076] Viscosity (bulk viscosity; n; measured at 20C; mPa-s): A cone-plate (E type) rotational viscometer was. F |E EB B e BB E a E E e Er a E E s E iw E y e e r R T E a vn ----rn [0079] Dielectric anisotropy (As; measured at 25C): A sample was put in a TN device in which a distance (cell gap) E EE ER SEEErEEe EE RE e RE rees [0080] Threshold voltage (Vth; measured at 25C; V): An LCD-5100 luminance meter madebyOtsuka Electronics
i
Ep 2011 003 41 ot1o60m08%1e)annVsoiilmtt,aagaennenao.dAiGtnovgterrcsatehioo(HcvhRoS2;5t) mbaaoangvwsoeelrdaegsdweaoattg205a%s;ubb1a:sasATlteHsade,wvaisceusicomfoorlrmesa.suAreamernet1awaas pptolihcee 5 Gaoyvep,laenddiaonnenededveovanwdis sdoeovnsiwnes chlarwgeed.laAtdeacbayliongavdehgee,vaAspMssevsols(81067TRmTlolsseccaonndss wiShVa) BTisghaspmeeadnvwoimheoeutr,daayx.rAevaotAagesehonldvalool8e uprerardea onsfa1rzaaotAlgoaxisein a105.ni ce vas elemined rea 10 d[6i0om8n2e,]natnViolmha,ngaenndholoddivtnignscrawetaios(VcsHhaRaa.25d:)wmibenoaawsuernneduaovt 6ga0csuru0aTlSA:EdTeehssdewe.avseASupmuisciersofmvoerottemaresga.ssu(Ar0eammerinctreohsveacadoasnpdpuslal1 5he1a) SLeaspapeic o1uhtTeHrdeavrdesaeanAhedevbice waeavsoRcnahgasrgce.uAed3e30c.8ahyoorlnagse1was2muunrycfofa167emllsaesamn.dsAwriena 15. 5a10s0v83a]ndasVhoalotiaongoneuhrtoaldicianaygh.arAtvaoodVteHaviRgc.se3h;womaseladasdauitrtoee3d2wi6p6e:rcrenatavgSeetoafgi1hy6.soAALToN1dtevi5cg.e tussd ovfamteessdubeynmensshd 8 eimsirdaeaatgweinn lth.t farn2d0amcoilngia,pwAasK3tc5o2m2e6rwse.s 4sler gwhaspriesosocrimeorcoutrheydaevpiceUSarHdSh0r0n(emadcsobey Ulsahgienwe)a,samnesssaudrseadntocr b15e7tmweielnssnceonvdscAacnoimphoskghonsoincg waasg2e0 cVHoRn.3eshal.arnegsessuanbiVE0Ri,aveecalyieng 2 A10v0o86nofVEolRp.e h8opledsienrarbaytoG0(V%HmR.o&em,eaasnudretdeatr2p0r-f1ra4nyA, 9T5N%Goefcmeori,o icha sample ws fc as tleadgnhs icnognaan.dIpn meessbtVhAiR6A0Cfdoerc5ay0i0nghuvesa,gandansnmtesaslede0fonr t16wemiessclonlc.yA mceomspsoesnigona = a(00u85)naRroespoVnsRe tihmoa;a amarsssuSredaatb205hoit;.ml AnLCD-5100 inane meter mabydOtsueka Elson Co. Liasn sedfoa wrhmieamsal rdaemTanNtdeAviGche rhcisnwas arhcaslo(gcoenGa4m9p),bA oenepwasoeane5r abs staa1 w5eis szS.AOsae mmiplcs eawass nardcasiinttahndgeadweasw8asGroardeiast.edRwitch That fowmavese(ct0iHoin, p5e,rp0a5riscaacyondo)twherdeov5pe, anodtahneaemvoeun.t Oof Ing 20 vnaensTmitued romuotun Fdnegvhiceowrasspmoanrdaroed0%Thvaamrasxmiimuamn,aoAruteofmgh(cxoeislspeocnodnsst)o 1a00p%ervioadnosfmmiaencneesadnedd fcohacnhgaenfgono1m0%60r%anasnmisamnicasnoc0to 0v%anvsamnisamnitcaencAe.rsApfoanlsiame (1 i3sksuemcoofnd) n3spaearoiiomda15nemeedara 55 f0a0lBliEm)e. Elastic constant (K; measured st 25: ) :HP4294A LCR Meer mde by YokogawaHowlPackrd Geoowaasssussuebosxetesasweasme2Dntm.iAcsoammpeAtwvaroasug.teian hhrzoantloanOlV1e0gn2t0 cswoams wahpapaonlnececo(lsanlags)ebcowoenn 40 C(HVaaynpwdeaorcbeuakineied pqnulJaaepatnvieoskoea)ng(sTw2h9e)rNeaRnmkdaaensuKaeoogrynoN2Se.g0ms1)r.eadnpvLda.a)glea7uonf5detaahsaecisdoofCs1y1al20cDdaeKpv3a3icwHear)neadonbvoaioankep(EpsltoeaDvseobttaaolgnse (1271158of)neNos.amKe2H2awnadybocoka.lAcunlsuaacohnsetaentv3omeadneveonaof hvealnesofcKa1r1 ianndaK3151n. Ga2 aond 25.519 on page S1a60m8p7l)e waSsponciiecde.ssAiDaCnvcooxgem1e0asVuirweadsstap2i5e; ocme:versso3l n1a6a5D1Osucppuedrieh1nel0etcsiooadensr,s1w0esimeernotfea 5 Roaapveoressseotranolc wcaasrecna)cu(edaflomoIchoenfsoilaotwiong ecqua.tor (pec restance) = (otage) (oHEe capacy n[0i05h8 LHuoldcaClhpysail H(a:ndmoaasnts(rEexaodtnoBoevmanfonmpaapraactuer)e.upa mA1h9e,la(l50i8cdhInw2a0s00m,easruurseed sGco.o1r4i).n3gAgaep 50 GvaacsinnalfonoInrgisowaswesdgasrcalel a4nd3a 0psaondra moeormosacmopper(aaudt fnomre2:hrMs,AaJnd hsrno, gNaipn(2Co-rap7e)rabieotnw,eeAn lap (Pia cladacing own ain heh alechageES TESS 35:
B-2x (@- al x tame. ** e7003s839s]5e0Gn,a.sescpAhercocmaiaeetr.oggrAoacpshaiscpahanaoSlyrosils(:u2GmDC.B-.p11o4(t8ainGgnaislh)C3hr0soa.mmabtproleger0ai.h3moa3rd.eaibynmSd3ehidmkeadeezurCsor(2sp15o0r)autweiornGiewmaesstau2s6d0oCr
=
EP 2811003 A1
cJootmapnoeunadsa. sAtfatriotnharycphoasne,wnaasnkoelpatr)atm2a0d0ebyorA2geminnutTeesc,hntohleoogileasnncw.awsahseautseeddtofor28se0paCraattiaonraotfecoofm5poCnepnetr miinnoutth.e sAasmapmlpelerwecaosr.preApraerecdoirndearwcalsoCnRSeAsoClvuotmiaolno(p0a%bcymwaediegbhy,Shainmdahdezun|Cmoripcorroatliloenrtoorefnseeoqounalwas cneieeold. 5 cThoemrpeosuuntdisn.gchromatogram showed arelnton ie ofapeakand pak are corresponding to achofthecomponent c{o00l9u0m1ns mAsay aclhoebenvoeddiuftorinsgeptahrastaimnpglteh,eccohmrpoonnen,thceoxmaponuenadnsd: HPf-o1rt(h mnatyha3s0omb,ebusreed.0.T3hl2ommw,ifnimgicacpilkry 10 0R.e2s5toukmC)ormpaordaetiboyn AangdenBtP-T1e(cehnnlgag3e0sm,Ibn.orRc0.32 memn,giln3i0ck,nebsorse00..322m)mmaidme tbhyiSckGnEesnse0r.n2a5tuonma)lmPay.deLib.y mcaaypiatlsaonbecosluemdnfCoBPt1h-Mp5u0r-po0s2e5olfeanvgihdi5n0gma, boorvee0.r25ofmmpe,afksmoUfitchekncoemspsou0.n25dus.m) cde by Shimadzu Corporation 15 bC1e0al0mo9wa1.)tTohgAerrafmuaoictfoclririryqesuostipadlocncrdyossmtpatlocuaonmadpstoucan(ndsbtcehoendtenatueicmntbeededriunosftihnmegocaloemgp)sosoihftrtioohmnalimoaugyirabpcehyc.salaAclualcatotomedpoobfuytntcehse.pmaeWlthheaorndeaatsshedinecstachrpeiibgleardsy. 3co5l1um(onnse)desAccrciobreddianbgo.vea waetre(u%sbedy, waeciagthe)cotfotnheoequfciceyonfaeaccohmpofouthnedsuiwadsccaylautceodmpfooumndtshemaaytboe rheegaprdked
20 {d10e0s0dc9fr2i]inbtedoTnhbseeloiiwn.vTeanTbthlieeon3cwobiemlllpobowe:uneIdxnspTlaianbilCneeodm3p,ianrdacetotinaifvliegbuEyrxaawtimaopynloeoffs1Ea.xna4dm-pcElyxecasa.mhpelTxehyselnwieenvrieesnatdienossnc.riisAbnepodtreulsniitmnihgteesdsiybzmyebdotlhnesuaEmcxcabomrpdlnieensxg.t c10o.m2posyumnbdo.liAzerdatcoo(meprocunntdagcaet)eosfptohnedsqu tcheynuambecroofmphouendscosmpeoxupnrde.ssAedsyimbtorlms(o)fmweeaingshtapneyrcaennte(3lbayuwceriysgtahl
25 btaesreed,onVtahleuteostoflcwheairgahctoasfhteicqsuoifdireysctomlpcoosmiptoosntwoenr.eTshummuairdizceydsntl caosmtpopsirtion contain an imputy i addon
Table 3 Method for Description of Compounds using Symbols R(Ag-Zy-Zy AR
9 Loftermial Group R-_ Symbol
4) Ring Stucture-A,-_ Symbol
CCotta r
non-
x
Collar 0C,Har ChCh
Vmvon.
i"
CHHaCpeHyCHH=CyH:
owvr
~> B
CollarCHCH-C Hy mV
8)
CFCH
Ver
CFACHC Har
Veen
&
" 2)Right-terminalGroup-R' Symbol 2)
"Car
a
"
OCHane
"on
cHecH,
v
LCCHHEaCHC.HCeHCeH;r Wwnv
-& ah
C
&
srs)
"
Cum CHECHC Hy MVR
check,
vee
a*
aF
CN w
z
ep 2011 003 A1 onium
: ocs,onia 2; siyneod
oe
2
"coo.
&
<3
(5 a
2
pnso -CH=CH-
vTono
. owto
x:
[Seman]
Example 13-BB(F)B(F.F)-CF,3
Example 23-BB(F)B(F F)XB(F.F)-F
x
Los v=tos
Oo { fk r ; F
* Emp 1
[0093]
.
-
.
L000
SesmeERcr [wen[0%|
[vweioeprew aanr||wni|] Eo TED 3-S8oB(RFFrIXBB(EFAFR)-EFAT[|e61s2n|| ha||
EBERT
# comperaianghs [0094] Ni =76.T8c<-3C0;C; An= 0.127; Ac =6.7; Vth = 221 V; n = 8.6 mPa's.
[ [vwia w mesne [|rw|s] joT[0edu0p9s5em]rdeidAtoelyidqauimdpcroaymstaat(l 5co-hmpomsdilteiomsnewatassfhooromrru,lpaCmteoodmtipnwiahriaecchsotmahesdcoocsmtpoonunnndoxrftahenofi.rsht cToermepxocnoepmnptooofsltrhoenniwnevepdnrtoioospnuweeadds
nt
.
[[oaosssep[[aassrrooaa||5orre]]
Ea ET
SERENE |G5| 6)%|
SBBPBEPAEERYE |522|15)% |
SSBB FNBERIF
-- eTyme urs [0096] NI=77Tc. <-21 0C ;AnC =0.; 127;Ac =5.6; Vth = 244V; n = 7.2 mPa's.
2 [0098]
.
seEmFncR [r|s3h%] seamerRcr [e|n| SEBBEBFACR |(H|3r%|
[ [oomsae |[r w5e]] [sveor aan|we]
s
[[sseepalelawnse||nsrwel]
"
E[ E E sea ec en |t5]
[sea[eorn|s5]
SesrreEnT [60
"
SHBBXBEFLF [z|orx|
SHeBGERF |aa|v3y%|
.
S88PBEF NEFFYE|02|23)%|
oRrBE AER | 6221
[0099] NI =80.6C; Tc <-20C; An = 0.108; As = 8.6; Vth = 2.08 V; n = 20.0 mPa-s. Example 3 [0100]
(ssernn J[ooaorns |nion]
:
[oJ swssne|ew |[wm]
.
oE me le Tern [|wm]
C mers TJaE e |
.
J f amesa es s las)) s ||)
m me es n J[easo)ns s ||on)
.
(omesr ss[[moowunsn||on|n
[mssi srn [aowrnns s||or|n
-
( (m me a6e r m0||n r||
[sssmse[noom n|nonr
\. uwemn [[m[ [J ssssrasrs esna ae|[[rm wemsm nmn [|||emoownnnnr]]]] * [0101] NI=82Tc. <-27 0C; AnC =0.; 115;A=z 9.1; Vth = 2.06V; =24.3 mPars.
-
l m ren e ea an s ||e]
C ewR an |on
.
I C-- as Joa |e
.
Emr en fr ora |eon
[[ssssseormf|pcoezamnn||eoornnn]
"
EP2811003A1
[0103] NI= 704C: T<2e 0C: An= 0.100; Ac = 7.7; ih = 191 Vin = 142 mPa.
Exampl5o
5 og
[ssaampaennes Ta[rwo[|ooanr]]
[[T Svamse oa rs [ rrn [|o worr]]
.
[am Tews [or]
SrRERS [e|oonv
sE aaensa Jwon n |5)
SEBERNSERT
sSHeBFeBErRRSERIE |6219|5%|
SSCERBFERBEEFFNNEEEERRIFT|| 6G2a2t1h)|| 5%% ||
[0108] NI=77.5C:Te<-20G; an=0.120: Ac = 105 Vin = 183Vi = 180 mars
examples
fot0g)
=
SsarEeeRsB |[(oamn||o]4h%|
[[ seo mo[paae wne||rw]e]
"
f[ umesmalel||ewnee]]
"
[[assesoess llearso)||wwee]]
[[savsosol[eearroosnn||woszen]|
w
seeBFRFE)RT [13e0) ||ra8n%||
SerrraEnE |ot|son%|
"
[ [ssmw weooiio roo n||noornn||
[swov|oezrn|oen
=
. 88 Te
. Camp [0108]
.
J [[esSsmsaesrwmaraner5 [vzanr||noe]|
013 87.2204 1-500 Soommaarrnreersnn[[oaewrn|| ]| msmearrarnon [faewwn[|m=|]
ow s e[[eei osnr[|m=)]|
[w[ wpesmew fasy |=)
Gwmsee {[ooww |aa))
[ wmmeer[[r oeon an ||a roenn
[[sssssrrmorsrseanrnr [[eeann||e||
.
[Eemaers[aeapnr|nt
. J--
[0110]
.
" -
[sosspmmaeernes[[eenn||o]i] [Swomserrener [[waewn[|oon|]
[ T ms e e w Trw s ||owri]] moarr [Jeer || ooni]] [ [w ae w [l@eesr e ||ooir]] [ewJe es |roi]
=
EP 2811003 A1
(conte)
E Searrernr E |ei|n|
swer[onm |e|
[SpHrBePmBeEenEsERE[|e6a2rn1[|9s5%x)|
SaarRGERT |62|o)n|
Ea CN [owe[e oo e [as]
OMA) NI= Te<-820C1 ;An=20.11 8;4s=C7.2:Vh =227Vin = 15.0 mPa,
Examples
ic]
V2BBBFF
.
[VeamesaPBRCr T|e1 r ||9 o%n]|
[m[ s ya [[wertna [[wmonw]]
Zswoerenr
aon [een |on|
.
E [swo a [Corrm |n0]
swesEnt [60
swemeERT |02|m 6%|
serRrFIErRE |02| 26%|
SBBPBE EERE |02|2 #%|
([09111134]) NTIhe6c6o7mpoCs;iiToon<s-i2n0ExCamapnle=s0.111301 3hcav=e8a5,laVrIgne=p2i23vidil=c2t3ic5 marPiaso.opy in comparison ith the com {puonshietronexaccecloerndtincghatroacCtoemripsatriactsive Example 1. Thereor, he laud crystal composton of the preset nvenlon has Industrial Applicabilly m19a1x1i5]numTehmepienrvaenutrionofcoannceammsicapqhausie.carlyoswamlicnoimmpuomsteomnpselsriantogfutahtrenasetmaolniepohfasceh,aarascmeailsvitsscossiutcyh, assaaibgeh 55 copativcaillalmigshltoapnyd,aaliagrghe sdialcbtii{c anhiesao,loopayu. aiadgestsplecciomrpeosissitoanncheaavianggaescuaasbilcboanlsatnacnetreghairgdhinsgtaatbeaislt wdoeovfithheacvhaairsanhcotgterrse.spoAnsqeuiimecr,ysltaarlgdeivspollaaygcevhiockeinigncrludinagalsauorcgheacocnotrmapsotsattoo,nailsoanpgplsieerdvitcoecHoenatndesoafnorAthM,
n
ep 2011 003 A1 anus cane ue or kd rt rotor, crys lisn a 0 ort,
cams
1.
cAoumpsoutndcrmepsosnieodn tbaytmhalsa nemava. I
fhsatscomapndonceontnaann laesattoanneccomopouunndslleeaddffoom bhee ggroovup
x3
x!
"
RA
CFs
1)
x4 m x2
2
=
ef(w= e n e
@)
herein, isaly having 1112 carbons, aon hing 12 carbons alien ing 2 o 12ctor,xand
5 T Sire pan1icueonnsre 14Shonen, o e u 1 phon non. Site phoions 254
Iuoro-1,4-phenylene; Z'is independentlaysinglebond, ethory carl bane ylon xy;e X', X2, X3 an X*adre independently
55 2. Tomheetgroiupsot ammpposton acpcrorsdainnged0 anrm1 where teorrsmt amp1.o1neti aston compoundsoled hydrogen or fluorine; and m and n are independently 1, 2 or 3.
js
F
rye
2
FF
er zomonan
r
,
RO rom
4
F
0
F
F
wren
(15)
1s
F
FF
.
.
.
*
F
FFF
w
FF
"
FF
>
.
-
i EP 2 811 003 Al
CF3 5
F
10
CF3
15
. CF3 F
20
FFF
25 CF
F
30
Rr
335
F
CFFs
F
40
CF
OOO "45
F FF
CF3
"50
55
.36
(1-12) (1-13) (1-14) (1-15)
((11--1166))
(1-17)
om(1-18)
EP 2 811 003 Al
FF
C F3 (1-19)
5
FF FF
wherein, R1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons.
10
3. The liquid crystal composition according to claim 1, wherein the first component is at least one compound selected from the group of compounds represented by formula (1-6) according to claim 2.
4. The liquid crystal composition according to claim 1, wherein the first component is at least one compound selected
15
from the group of compounds represented by formula (1-17) according to claim 2.
5. The liquid crystal composition according to any one of claims 1 to 4, wherein the second component is at least one compound selected from the group of compounds represented by formula (2-1) to formula (2-13):
20
R2
(2-1)
25
(2-2)
30
R2
35
R2
40
COO
3
(2-3) (2-4) (2-5)
45
(2-6)
50
R2
55
(2-7)
,37
EP 2 811 003 Al
R2
5
1o0
R2A{
> <{
{ ) { R?
(2-8)
(2-9)
15
20
25
OOO R22.
3
30
R2
F
3
(@21-122))
(2-13)
35
wherein, R2 and R3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having
2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine.
6. The liquid crystal composition according to claim 1, wherein the second component is at least one compound selected from the group of compounds represented by formula (2-1) according to claim 5.
40
7. The liquid crystal composition according to claim 1, wherein the second component is at least one compound selected from the group of compounds represented by formula (2-13) according to claim 5.
8. The liquid crystal composition according to claim 1, wherein the second component is a mixture of at least one
45
compound selected from the group of compounds represented by formula (2-1) according to claim 5 and at least
one compound selected from the group of compounds represented by formula (2-7) according to claim 5.
9. The liquid crystal composition according to any one of claims 1 to 8, wherein a ratio of the first component is in the
range of 3% by weight to 25% by weight and a ratio of the second component is in the range of 25% by weight to
50
97% by weight, based on the total weight of the liquid crystal composition.
10. The liquid crystal composition according to any one of claims 1 to 9, further containing at least one compound selected from the group of compounds represented by formula (3) as a third component:
55
.38
P2811 003At
Cee Gre x5
Pp
x6
CwhleareicnyRclioshaelxkyalnhea.v1i.npg 1h1n2 cyarboins,nakeo,hav2ing.0o12rcoraoo.b-oorr1eannlky4eesnnyleh.h3a.ev5inlgnl2ucyo1-2e-capnrbroenesn:n,neg,
5
1e.3loxyanae2n5.s6yo.rlcaXhtayaonrpdybraone-ni,ndy5ep.ie)ndnaonytpyiymiodignea-, Suryine2: Y1 risinngl,e oanrdi,ndefocfrlosmoerlaymeanneoonyy.: andpsnz dork
1. oThemlatuhdGcryousptofccoommppoosutnodnsarcecporredsienngtoedlbyio1m0,awhere1i)nohefoirmdulcao(m2p6o)nents astanecompu selected
F
FF F F
3
ep2001031A1
[FE
.
0 Sook,
OO
F
"
.
.
d
Q
yO-CE
(3-10)
*
EY
vF
#
FF
F
FF
5
.
CFs
FF
r= o .
(317)
5
F
&
a
-
R*
.
F
FP
F
F
F
x x
.
F
Xx
x10
x8
Y x8
.
(3-20)
P2811 003 At
x1
x8
x7
Fe x
s
R*
12 10 xe yt
x8
(3-22)
x1
x8
Fe Xx
i
R*
0
y!
x12
x10
Nd 6
(3-23)
=
R*
xX Fe xX
(3-24)
Xo ye 0
y!
x8
hrs, R i aly having 1012 carbons, akory ving 11 12 carbonas aller having 210 12 carbons; XC,
X8,X7,X8, X9, X10, X11and X 2are indepheydrnogd en e o fn luot rinel;aynd Y isfluorine,chlorineortriluoromethoxy.
35 12. Tfhoemltahuedgrcoyusptofccoommppoosutniodnsarcecporredsienngtoedlbyifor1m0,ulwahe(r3e-i1n)haecciodrdcionmlgopocnleantms11 astanecompund selected
15. fhomehde grcroyusptaolfccoommppoosuionndacrceoprredsienngtteodcbylafno1r0m,awh(a3r-s1n9thccthoiracntgoocamm 11pa. eoas nonsecomnpoutnd select
40 14, fTonmefhiedgrcroyusptaolfccoommppoostuinondarcecporredsinegntoedcbayimfo1r0,mwahe(r3-17)thacchorddincgotomcpaemn1a1. toenscsompetund selected
15. fTohmolhuedgcrroyusptaolfccoommpopsoituinondarcecporredsienngtteodblyanfo1m0i,lwahe(r3e.2i1n)thactchoirdcionmg0pocnaemnt1s1.aaonecompound selected
1. fTohmolhuedgcroupyofctompaounld rcepreosentmedcblypafno1or0,mwahse(r3e.ii22n)tahoctchoinrdcioantmogpoccnaemnct11.aoeasrtondcoimpogundstelecoted
"0 1. Thhaerlaonugedocfry5st%ablycowmepiogshtot0n6a5c%cobrydiwngeiotanbyaasneeoofn tihmisa10w10e16i,owghtehhreeihnuairactryostfalthceomhpdsicoonm.ponents
15. TShheaus ies 7c0yCoafchoemrpo,siaontaacacnkfolooapnryyo(dn25oiCf)cnaatmwgsa1v1e1l7ng,iwhheorfi5n8a nianmomeuterts e0m.07paeomfrorasna,emntadteica Gelactic anisotropy (5G) at aquency of 1 1 20 mor,
15. Alla crystal dpa doi inciuing ie Iaidcystl composion acerding to anyoneof cis 1018.
20. Thu rysaldsply devs accordigtoclan 1, whean orperaetingimande nthe audcrystal laydevs
EP 2811003 A1 is:a TN mode, an ECB mode, an OCB mode, an IPS mode, a PSA mode or an FPA mode, and adiving mode in the liu crystal splay devi i an active malrx mode. 21. Use of the liquid crystal composiion accordingto any oneofclams 110 181 a uid crystal display device.
x "
ep20m 00301
TERNATIONALSEARCHREPORT TIT TIE
ErerESeaT sie
s eons oe Sos seams i SoA ore (CO9K19/42(2006.01)1, CO9K19/12(2006.01)i, C09K19/16(2006.01)i, CO9K19/20
cri nrspe re
BE EEE
a BS), Coon1374,
I
RS TATE as De 0 Hemanis
"
w 3 dopr e ao m Gonr o,
=
a | or 2ommesseses n atnipron sok ant crosses, a
50m 2001 1.2000,
A
a | o2r zEoveI-ommSenxe sreniezne ncomp,
a
-
PER rs
. 2 i REE Tcamer E ETEE
MAI... A oT Ee EpmrmmaomameI ee tt 4 be
07 documentering nce slo, se,exbbion oaber oxaas iSt
oE r T TTTAGLRrtoh meta Fg de er
"A docuof smseptnefty
E TE r oT o 1
Loao on
For PCT/(sIecoS ndshA eet)ZulI y 200 09).
-- ss
"
EP 2 811 003 Al
INTERNATIONAL SEARCH REPORT
International application No.
. oer | memsmees| PCT/JP2012/084032
5
C (Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT
Category*
Citation of document, with indication, where appropriate, of the relevant passages
Relevant to claim No.
A
JP 2004-182884 A (Chisso Corp.),
02 July 2004 (02.07.2004),
entire text
1*0
&& UUSS 22000044//00110088448899 AAll
1-21
15
.20
25
.30
35
.40
45
.50 rebm---- 55
Form P CT/ISA/2 0 (continuation of second sheet) (July 2009)
.45
EP 2811003 A1 REFERENCES CITED IN THE DESCRIPTION This listof roforoncoscitedby the applicant i orth reader's conveniance only. I doos notorm partof tho European `poaxtcelnutdeddocaunmdentthe. EEPvOednistchloauigmhsgraelatlacbalrtoyhiansthbieseongatradk.en in comping the references, ators or omissions cannot be
Patent documents cited in the description ++ UJPpS2050705073408A78[A020[60470]06 [0067] + UP SS9176221 A [0067] + JP S5716532A8 [0067]
++ IIPP HH2I230362265A1A[[100008667]76] + US 3650505 8 [0067]
Non-patent literature cited in the description
+ +
Organic Organic
Syntheses. Reaclons.
John John
Wiey& Wiey &
Sons, Sons,
Inc, nc,
[0068] [0068]
+ CompreOhrgeannicsSynithvesies. PergamonPress
+ 1N0e0w68E)xperimental Chemisty Course. Maruzen Co.
LG, (0068)
+ M.IMAIta. Molecular CrystalsandLiquidCrystals, + L1i9q9u5i,dvCorlys2t5a9l,H3a7nd0b0o7o7k]. Maruzen Co, Lt, 2000,
196 (0088)
"