JP2018145192A - 重合性化合物及び光学異方体 - Google Patents
重合性化合物及び光学異方体 Download PDFInfo
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- JP2018145192A JP2018145192A JP2018052601A JP2018052601A JP2018145192A JP 2018145192 A JP2018145192 A JP 2018145192A JP 2018052601 A JP2018052601 A JP 2018052601A JP 2018052601 A JP2018052601 A JP 2018052601A JP 2018145192 A JP2018145192 A JP 2018145192A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/84—Hydrazones having doubly-bound carbon atoms of hydrazone groups being part of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】下記式(I)で表される、重合性低波長分散性又は重合性逆波長分散性化合物;前記化合物を含有する組成物;前記組成物を重合して得られる重合体;前記重合体を用いた光学異方体。前記組成物は液晶組成物であることが好ましい。
(G1は1,4−ビフェニル基等にN−(2−ベンゾチアゾリル)ヒドラゾン基等が置換した2価基;R1−(A1−Z1)m1−及びR2−(A2−Z2)m2−は各々独立に、R1/R2側末端がアクリロイルオキシ基等で封鎖された2価の連結基であって、該連結基はアルキレン、フェニレン、シクロアルキレン等から選択された1又は2以上の2価の基が、エーテル基、エステル基等を介して連結して構成される。)
【選択図】なし
Description
《位相差の測定》
配向膜用ポリイミド溶液を厚さ0.7mmのガラス基材にスピンコート法を用いて塗布し、100℃で10分乾燥した後、200℃で60分焼成することにより塗膜を得る。得られた塗膜を市販のラビング装置を用いてラビング処理する。
A1及びA2は各々独立して1,4−フェニレン基、1,4−シクロヘキシレン基、ピリジン−2,5−ジイル基、ピリミジン−2,5−ジイル基、ナフタレン−2,6−ジイル基、ナフタレン−1,4−ジイル基、テトラヒドロナフタレン−2,6−ジイル基、デカヒドロナフタレン−2,6−ジイル基又は1,3−ジオキサン−2,5−ジイル基を表すが、これらの基は無置換であるか又は1つ以上の上述の置換基Lによって置換されても良く、
Z1及びZ2は各々独立して−O−、−S−、−OCH2−、−CH2O−、−CH2CH2−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−OCO−NH−、−NH−COO−、−NH−CO−NH−、−NH−O−、−O−NH−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−、−N=CH−、−CH=N−N=CH−、−CF=CF−、−C≡C−、又は単結合、若しくは−CR0−1R0−2O−又は−OCR0−1R0−2−(式中、R0−1及びR0−2は各々独立して式(Z−0)におけるR0−1及びR0−2と同じ意味を表す。)で表される基を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良いが、Z1及びZ2のうち少なくとも1つは−CR0−1R0−2O−又は−OCR0−1R0−2−で表される基を表し、
G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香環を有する2価の基を表すが、G1で表される基中の芳香環に含まれるπ電子の数は12以上であり、G1で表される基は無置換であるか又は1つ以上の置換基LGによって置換されても良く、
LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG−(SpLG−XLG)kLG−で表される基を表しても良く、ここでPLGは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLGはスペーサー基又は単結合を表すが、好ましいスペーサー基は上記Sp0で定義したものと同一のものを表しSpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLG−(SpLG−XLG)kLG−には−O−O−結合を含まない。)、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良く、
m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表す。)で表される化合物であることが好ましい。
W2は水素原子、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、W2は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基LWによって置換されても良く、若しくは、W2はPW−(SpW−XW)kW−で表される基を表しても良く、ここでPWは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpWはスペーサー基又は単結合を表すが、好ましいスペーサー基は上記Sp0で定義したものと同一のものを表し、SpWが複数存在する場合それらは同一であっても異なっていても良く、XWは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PW−(SpW−XW)kW−には−O−O−結合を含まない。)、kWは0から10の整数を表し、
LWはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LWはPLW−(SpLW−XLW)kLW−で表される基を表しても良く、ここでPLWは重合性基を表し、SpLWはスペーサー基又は単結合を表すが、SpLWが複数存在する場合それらは同一であっても異なっていても良く、XLWは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XLWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLW−(SpLW−XLW)kLW−には−O−O−結合を含まない。)、kLWは0から10の整数を表すが、化合物内にLWが複数存在する場合それらは同一であっても異なっていても良く、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはPY−(SpY−XY)kY−で表される基を表しても良く、PYは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpYはスペーサー基又は単結合を表すが、好ましいスペーサー基は上記Sp0で定義したものと同一のものを表し、SpYが複数存在する場合それらは同一であっても異なっていても良く、XYは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XYが複数存在する場合それらは同一であっても異なっていても良く(ただし、PY−(SpY−XY)kY−には−O−O−結合を含まない。)、kYは0から10の整数を表すが、W1及びW2は一緒になって環構造を形成しても良い。)から選ばれる基を表す。)から選ばれる基を表すことがより好ましい。溶媒への溶解性、合成の容易さの観点から、G1は上記の式(M−1)、式(M−3)、式(M−4)、式(M−7)、式(M−8)から選ばれる基を表すことがさらに好ましく、式(M−1)、式(M−7)、式(M−8)から選ばれる基を表すことがさらにより好ましく、式(M−7)、式(M−8)から選ばれる基を表すことが特に好ましい。より具体的には、式(M−1)で表される基としては下記の式(M−1−1)から式(M−1−6)
m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表す。液晶性、合成の容易さの観点から、LGはフッ素原子、塩素原子、ペンタフルオロスルフラニル基、ニトロ基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、又は、任意の水素原子はフッ素原子に置換されても良く、1個の−CH2−又は隣接していない2個以上の−CH2−は各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−O−CO−O−、−CH=CH−、−CF=CF−又は−C≡C−から選択される基によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すことが好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良く、1個の−CH2−又は隣接していない2個以上の−CH2−は各々独立して−O−、−COO−又は−OCO−から選択される基によって置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基を表すことがより好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基若しくはアルコキシ基を表すことがさらに好ましく、フッ素原子、塩素原子、又は、炭素原子数1から8の直鎖アルキル基若しくは直鎖アルコキシ基を表すことが特に好ましい。
(製法1)下記式(S−9)で表される化合物の製造
式(S−1)で表される化合物のカルボキシル基を保護基(PG)によって保護する。保護基(PG)としては、脱保護工程に至るまで安定に保護しうるものであれば特に制限は無いが、例えば、GREENE’S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS((Fourth Edition)、PETER G.M.WUTS、THEODORA W.GREENE共著、John Wiley & Sons,Inc.,Publication)等に挙げられている保護基(PG)が好ましい。保護基の具体例としてはテトラヒドロピラニル基、tert−ブチル基、メトキシメチル基が挙げられる。
(製法2)下記式(S−18)で表される化合物の製造
式(S−4)で表される化合物を塩基存在下、式(S−10)で表される化合物と反応させることによって式(S−11)で表される化合物を得ることができる。塩基としては例えば製法1に記載のものが挙げられる。
(実施例1)式(I−1)で表される化合物の製造
転移温度(昇温速度5℃/分)C 155 N >220 I
1H NMR(CDCl3)δ 1.12(q,2H),1.26(q,2H),1.50(q,2H),1.67(qd,2H),1.91−2.27(m,14H),2.43(t,1H),2.56(tt,2H),3.77(d,2H),3.88(d,2H),4.09(t,4H),4.40(t,4H),5.88(d,2H),6.17(ddd,2H),6.45(d,2H),6.85(d,1H),6.92(m,5H),7.02(d,4H),7.19(t,1H),7.37(t,1H),7.59(m,2H),7.71(d,1H),8.44(s,1H)ppm.
(実施例2)式(I−2)で表される化合物の製造
転移温度(昇温速度5℃/分)C 90−110 N 182−187 I
1H NMR(CDCl3)δ 1.07(q,2H),1.24(q,2H),1.47−1.90(m,24H),2.09(m,4H),2.22(d,2H),2.39(t,1H),2.53(t,1H),3.74(d,2H),3.85(d,2H),3.94(td,4H),4.17(td,4H),5.82(d,2H),6.13(dd,2H),6.40(d,2H),6.80−6.99(m,6H),6.98(d,4H),7.16(t,1H),7.33(t,1H),7.55(m,2H),7.67(d,1H),8.40(s,1H)ppm.
(実施例3)式(I−3)で表される化合物の製造
LCMS:1058[M+1]
(実施例4)式(I−4)で表される化合物の製造
LCMS:1142[M+1]
(実施例5)式(I−5)で表される化合物の製造
転移温度(昇温速度5℃/分)C 119−122 N 144 I
1H NMR(CDCl3)δ 1.25(m,4H),1.48(m,8H),1.63−1.82(m,12H),1.90(m,2H),2.07(dd,4H),2.24(d,4H),2.52(m,2H),3.30(t,1H),3.86(dd,4H),3.94(t,4H),4.08(td,2H),4.17(t,4H),4.50(t,2H),5.82(dd,2H),6.12(dd,2H),6.40(dd,2H),6.88(m,6H),6.97(dd,4H),7.16(t,1H),7.33(t,1H),7.52(d,1H),7.64(d,1H),7.69(d,1H),8.28(s,1H)ppm.
LCMS:1102[M+1]
(実施例6)式(I−6)で表される化合物の製造
LCMS:1084[M+1]
(実施例7)式(I−7)で表される化合物の製造
LCMS:1058[M+1]
(実施例8)式(I−8)で表される化合物の製造
LCMS:902[M+1]
(実施例9)式(I−9)で表される化合物の製造
LCMS:1021[M+1]
(実施例10)式(I−10)で表される化合物の製造
LCMS:1171[M+1]
(実施例11)式(I−11)で表される化合物の製造
LCMS:1159[M+1]
(実施例12)式(I−12)で表される化合物の製造
LCMS:837[M+1]
(実施例13)式(I−13)で表される化合物の製造
LCMS:861[M+1]
(実施例14)式(I−14)で表される化合物の製造
LCMS:944[M+1]
(実施例15)式(I−15)で表される化合物の製造
LCMS:1039[M+1]
(実施例16)式(I−86)で表される化合物の製造
転移温度(昇温速度5℃/分)C 122 N 142 I
1H NMR(CDCl3)δ 1.24(m,4H),1.48(m,8H),1.60−1.83(m,12H),1.93(m,2H),2.08(t,4H),2.23(m,4H),2.54(m,2H),3.86(dd,4H),3.94(t,4H),4.17(t,4H),4.53(t,2H),4.65(t,2H),5.78(dd,1H),5.82(dd,2H),6.08(dd,1H),6.12(dd,2H),6.39(dd,1H),6.40(dd,2H),6.88(m,6H),6.97(dd,4H),7.16(t,1H),7.34(t,1H),7.54(d,1H),7.66(d,1H),7.70(d,1H),8.36(s,1H)ppm.
(実施例17)式(I−89)で表される化合物の製造
転移温度(昇温5℃/分)C 71 N 115 I
1H NMR(CDCl3)δ 1.19−1.29(m,4H),1.41−1.82(m,22H),1.91(m,2H),2.08(m,4H),2.24(m,4H),2.53(m,2H),3.62(m,3H),3.67(m,2H),3.84−3.90(m,5H),3.94(t,4H),4.15−4.19(m,6H),4.53(t,2H),5.76(dd,1H),5.82(dd,2H),6.08(dd,1H),6.12(dd,2H),6.37(dd,1H),6.40(dd,2H),6.84−6.90(m,6H),6.95−6.98(m,4H),7.14(t,1H),7.32(t,1H),7.53(d,1H),7.65(d,1H),7.69(d,1H),8.34(s,1H)ppm.
LCMS:1244[M+1]
(実施例18)式(I−121)で表される化合物の製造
転移温度(昇温5℃/分):C 77 S 90 N 109 I
1H NMR(CDCl3)δ 0.89(t,3H),1.20−1.35(m,10H),1.61−1.69(m,6H),1.78(m,2H),1.90(m,2H),2.07(t,4H),2.23(d,4H),2,50(m,2H),3.69−3.76(m,12H),3.83−3.87(m,8H),4.11(t,4H),4.32(t,6H),5.82(d,2H),6.15(q,2H),6.42(d,2H),6.83−6.98(m,10H),7.13(t,1H),7.32(t,1H),7.53(t,1H),7.66(t,2H),8.13(s,1H)ppm.
(実施例19)式(I−122)で表される化合物の製造
転移温度(昇温5℃/分):C 85 N 128 I
1H NMR(CDCl3)δ 1.22−1.28(m,4H),1.44−1.47(m,8H),1.60−1.82(m,12H),1.90(m,2H),2.07(t,4H),2.24(d,4H),2.53(m,2H),3.30(s,3H),3.50(t,2H),3.66(t,2H),3.85−3.89(m,6H),3.93(t,4H),4.17(t,4H),4.53(t,2H),5.82(d,2H),6.13(q,2H),6.40(d,2H),6.83−6.90(m,6H),6.95−6.98(m,4H),7.14(t,1H),7.32(t,1H),7.52(t,1H),7.67(t,2H),8.33(s,1H)ppm.
(実施例20)式(I−123)で表される化合物の製造
転移温度(昇温5℃/分):C 89−95 N 145 I
1H NMR(CDCl3)δ 1.24(m,4H),1.65(m,4H),1.91(m,2H),2.05−2.25(m,12H),2.55(m,2H),3.30(s,3H),3.51(m,2H),3.67(m,2H),3.84−3.89(m,6H),4.05(t,4H),4.36(t,4H),4.54(t,2H),5.84(dd,2H),6.13(dd,2H),6.41(dd,2H),6.84−6.89(m,6H),6.97−7.00(m,4H),7.14(t,1H),7.33(t,1H),7.52(d,1H),7.67(dd,2H),8.34(s,1H)ppm.
(実施例21)式(I−124)で表される化合物の製造
転移温度(昇温5℃/分、降温5℃/分):C 101−105(N 82)I
1H NMR(CDCl3)δ 0.92(t,3H),1.08−1.91(m,26H),2.06(d,2H),2.24(d,2H),2.51(m,2H),3.30(s,3H),3.51(dd,2H),3.67(dd,2H),3.87(quin,4H),3.94(t,2H),4.17(t,2H),4.54(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.86(m,3H),6.97(m,2H),7.16(m,2H),7.32(t,1H),7.65(d,1H),7.70(d,1H),7.82(d,1H),8.36(s,1H)ppm.
(実施例22)式(I−125)で表される化合物の製造
転移温度(昇温5℃/分):C 67−100 I
1H NMR(CDCl3)δ 1.00(t,3H),1.28(m,2H),1.45−1.81(m,12H),1.97(br,1H),2.13(m,2H),2.26(m,2H),2.57(tt,1H),2.65(t,2H),3.27(s,3H),3.37(m,2H),3.50(m,2H),3.70(t,2H),3.95(q,4H),4.17(t,2H),4.33(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.87(d,2H),6.98(m,3H),7.15(t,1H),7.25(m,5H),7.32(t,1H),7.64(m,2H),7.69(d,1H),7.91(s,1H)ppm.
実施例1から実施例22と同様の方法及び公知の方法を用いて、上述の式(I−16)から式(I−85)、式(I−87)、式(I−88)、式(I−90)から式(I−120)で表される化合物を製造した。
(実施例23〜44、比較例1〜3)
実施例1から実施例22記載の式(I−1)から式(I−15)、式(I−86)、式(I−89)、式(I−121)から式(I−125)で表される化合物及び特許文献1記載の化合物(R−1)、特許文献2記載の化合物(R−2)、特許文献3記載の化合物(R−3)を評価対象の化合物とした。
〈変色〉
フィルムの黄色度(YI)を測定した。サンテスト実施前のYI値と、サンテスト実施後のYI値との差(ΔYI)を算出した。測定にはJASCO UV/VIS Spectrophotometer V−560を使用し、付属のカラー診断プログラムによって黄色度を計算した。計算式は、
YI=100(1.28X−1.06Z)/Y (JIS K7373)
(X、Y、ZはXYZ表色系における3刺激値を表す。)である。ΔYI値が小さい程、変色が少ないことを意味する。
〈配向欠陥〉
フィルムを縦10マス×横10マス、計100マスの領域に区分した。偏光顕微鏡観察によって、配向欠陥の生じたマス目の数をカウントした。値が小さいほど、配向欠陥が少ないことを意味する。
結果を下記表2に示す。
Claims (12)
- 一般式(I)
(式中、R1及びR2は各々独立して水素原子又は炭素原子数1から80の炭化水素基を表すが、当該基は置換基を有していても良く、任意の炭素原子はヘテロ原子に置換されていても良いが、R1及びR2のうち少なくとも1つは下記式(I−0−R)
から選ばれる基を表し、Sp0はスペーサー基又は単結合を表すが、Sp0が複数存在する場合それらは同一であっても異なっていても良く、
X0は−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、X0が複数存在する場合それらは同一であっても異なっていても良く(ただし、P0−(Sp0−X0)k0−には−O−O−結合を含まない。)、
k0は0から10の整数を表す。)で表される基を表し、
A1及びA2は各々独立して1,4−フェニレン基、1,4−シクロヘキシレン基、ピリジン−2,5−ジイル基、ピリミジン−2,5−ジイル基、ナフタレン−2,6−ジイル基、ナフタレン−1,4−ジイル基、テトラヒドロナフタレン−2,6−ジイル基、デカヒドロナフタレン−2,6−ジイル基又は1,3−ジオキサン−2,5−ジイル基を表すが、これらの基は無置換であるか又は1つ以上の置換基Lによって置換されても良く、
Lはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、
LはPL−(SpL−XL)kL−で表される基を表しても良く、ここでPLは重合性基を表し、SpLはスペーサー基又は単結合を表すが、SpLが複数存在する場合それらは同一であっても異なっていても良く、XLは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XLが複数存在する場合それらは同一であっても異なっていても良く(ただし、PL−(SpL−XL)kL−には−O−O−結合を含まない。)、kLは0から10の整数を表すが、化合物内にLが複数存在する場合それらは同一であっても異なっていても良く、
Z1及びZ2は各々独立して−O−、−S−、−OCH2−、−CH2O−、−CH2CH2−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−OCO−NH−、−NH−COO−、−NH−CO−NH−、−NH−O−、−O−NH−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−、−N=CH−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合、若しくは−CR0−1R0−2O−又は−OCR0−1R0−2−(式中、R0−1及びR0−2は各々独立して水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子又は塩素原子に置換されても良い。)で表される基を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良いが、
G 1 に直接結合する−A 1 −Z 1 −が
であるか、及び/又は、G 1 に直接結合する−Z 2 −A 2 −が
であり、
G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香環を有する2価の基を表すが、G1で表される基中の芳香環に含まれるπ電子の数は12以上であって、かつ、下記の式(M−7)から式(M−14)
T 2 は下記の式(T2−1)又は式(T2−2)
W 2 は水素原子、又は、1個の−CH 2 −又は隣接していない2個以上の−CH 2 −が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、
W 2 は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基L W によって置換されても良く
(ここで、L W はフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の−CH 2 −又は隣接していない2個以上の−CH 2 −が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良い。)、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の−CH 2 −又は隣接していない2個以上の−CH 2 −が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはP Y −(Sp Y −X Y ) kY −で表される基を表しても良く、P Y は重合性基を表し、Sp Y はスペーサー基又は単結合を表すが、Sp Y が複数存在する場合それらは同一であっても異なっていても良く、
X Y は−O−、−S−、−OCH 2 −、−CH 2 O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH 2 −、−CH 2 S−、−CF 2 O−、−OCF 2 −、−CF 2 S−、−SCF 2 −、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH 2 CH 2 −、−OCO−CH 2 CH 2 −、−CH 2 CH 2 −COO−、−CH 2 CH 2 −OCO−、−COO−CH 2 −、−OCO−CH 2 −、−CH 2 −COO−、−CH 2 −OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、
X Y が複数存在する場合それらは同一であっても異なっていても良く
(ただし、P Y −(Sp Y −X Y ) kY −には−O−O−結合を含まない。)、
kYは0から10の整数を表し、
W 1 及びW 2 は一緒になって環構造を形成しても良い。)
から選ばれる基を表し、
LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−S−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−CH=CH−、−CF=CF−又は−C≡C−によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG−(SpLG−XLG)kLG−で表される基を表しても良く、ここでPLGは重合性基を表し、SpLGはスペーサー基又は単結合を表すが、SpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは−O−、−S−、−OCH2−、−CH2O−、−CO−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CH=CH−、−N=N−、−CH=N−N=CH−、−CF=CF−、−C≡C−又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLG−(SpLG−XLG)kLG−には−O−O−結合を含まない。)、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良い。)
で表され、
m1及びm2は各々独立して0から6の整数を表すが、m1+m2は1から6の整数を表す。)で表される、重合性低波長分散性又は重合性逆波長分散性化合物。 - 式(I−0−R)において、Sp0が各々独立して、1個の−CH2−又は隣接していない2個以上の−CH2−が各々独立して−O−、−COO−、−OCO−、−OCO−O−、−CO−NH−、−NH−CO−、−CH=CH−又は−C≡C−に置き換えられても良い炭素原子数1から20のアルキレン基を表す、請求項1に記載の化合物。
- 一般式(I)において、R 1 及びR 2 の一方が式(I−0−R)で表される基を表す、請求項1から請求項2のいずれか一項に記載の化合物。
- 一般式(I)において、R1及びR2が式(I−0−R)で表される基を表す、請求項1から請求項2のいずれか一項に記載の化合物。
- 一般式(I)で表される化合物が、一般式(IA)
G 1 は一般式(I)と同じ意味を表し、
A 11 は般式(I)におけるA 1 と、
A 21 及びA 22 は一般式(I)におけるA 2 と同じ意味を表し、
Z 11 は一般式(I)におけるZ 1 と、
Z 21 及びZ 22 は一般式(I)におけるZ 2 と同じ意味を表し、
A 12 は1,4−シクロヘキシレン基を表し、
Z 12 は−CR 0−1 R 0−2 O−を表す。)で表されるものである請求項1から請求項4のいずれか一項に記載の化合物。 - 一般式(I)又は一般式(IA)において、G1が式(M−7)又は式(M−8)で表される、請求項1から請求項6のいずれか一項に記載の化合物。
- 請求項1から請求項7のいずれか一項に記載の化合物を含有する組成物。
- 請求項1から請求項7のいずれか一項に記載の化合物を含有する液晶組成物。
- 請求項8又は請求項9に記載の組成物を重合することにより得られる重合体。
- 請求項10記載の重合体を用いた光学異方体。
- 請求項1から請求項7のいずれか一項に記載の化合物を用いた樹脂、樹脂添加剤、オイル、フィルター、接着剤、粘着剤、油脂、インキ、医薬品、化粧品、洗剤、建築材料、包装材、液晶材料、有機EL材料、有機半導体材料、電子材料、表示素子、電子デバイス、通信機器、自動車部品、航空機部品、機械部品、農薬及び食品並びにそれらを使用した製品。
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