JP6568103B2 - 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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- JP6568103B2 JP6568103B2 JP2016566168A JP2016566168A JP6568103B2 JP 6568103 B2 JP6568103 B2 JP 6568103B2 JP 2016566168 A JP2016566168 A JP 2016566168A JP 2016566168 A JP2016566168 A JP 2016566168A JP 6568103 B2 JP6568103 B2 JP 6568103B2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/18—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms 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
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino 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
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/78—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Description
W1及びW2は各々独立して単結合又は2個から100個のπ電子を有する共役系を含む基を表し、
M1及びM2は各々独立してメソゲン基を含む基を表し、
n1及びn2は各々独立して0又は1を表すが、n1及びn2が0である場合該当する基は水素原子を表し、
n3は1から1000までの整数を表すが、
W1、W2、M1、M2は、各々独立して置換基Lを有していても良く、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−(SL−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、SLはスペーサー基又は単結合を表すが、SL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いが、(ただし、PL−(SL−XL)kL−には−O−O−結合を含まない。)、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、kLは0から10の整数を表し、
M1−W1、W1−M2及び/又はM2−W2は各々独立して共役系を形成していても良い。)で表される化合物を提供し、併せて当該化合物を含有する重合性組成物、当該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、重合性液晶組成物、当該重合性液晶組成物を重合させることにより得られる重合体及び当該重合体を用いた光学異方体を提供する。
<<R1、R2、R3、R4>>
一般式(I)において、R1、R2、R3及びR4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。また、R1、R2、R3及びR4は各々独立して水素原子又は炭素原子数1から20の炭化水素基を表すのが好ましく、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。より具体的には、R1、R2、R3及びR4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、ペンタフルオロスルフラニル基、シアノ基、ニトロ基、イソシアノ基、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−、−C=C−、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し(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。)、若しくは、重合性基を含む基が好ましい。
<<置換基L>>
一般式(I)で表される化合物は、無置換であるか、置換基Lにより置換されていても良い。置換基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−(SL−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、SLはスペーサー基又は単結合を表すが、SL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いが、(ただし、PL−(SL−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、kLは1が好ましく、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い。また、原料の入手容易さ及び合成の容易さの観点から、複数存在する場合は各々同一であっても異なっていても良く、置換基Lはフッ素原子、塩素原子、ニトロ基、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−、−COO−、−OCO−によって置換されても良く、任意の水素原子がフッ素原子に置換されても良い、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、複数存在する場合は各々同一であっても異なっていても良く、フッ素原子、塩素原子、ニトロ基、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−によって置換されても良い、炭素原子数1から12の直鎖状アルキル基を表すことがより好ましく、複数存在する場合は各々同一であっても異なっていても良く、フッ素原子、シアノ基、メチル基又はメトキシ基を表すことが特に好ましい。
<<W1、W2>>
一般式(I)において、W1及びW2は各々独立して単結合又は2個から100個のπ電子を有する共役系を含む基を表す。原料の入手容易さ及び合成の容易さの観点からW1及びW2は、単結合若しくは任意の炭素原子がヘテロ原子に置換されていても良い2個から80個のπ電子を有する炭素基又は炭化水素基と、単結合若しく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、任意の炭素原子がヘテロ原子に置換されていても良い炭素原子数5から80の芳香族及び/又は非芳香族の炭化水素環とを含む基であることが好ましい。
B1、B2及びB3は各々独立して単結合又は置換されていても良い炭素原子数5から80の芳香族及び/又は非芳香族の炭化水素環を表すが、当該炭素環又は炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良く、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いが、B3が単結合を表す場合は水素原子又は置換基Lで表される基が結合し、n4及びn5は、0から10までの整数を表す基がより好ましい。
一般式(I)において、M1及びM2は各々独立して、メソゲン基を含む基を表す。
<<n1、n2、n3>>
n1及びn2は各々独立して0又は1を表すが、n1が0である場合後述するW1に連結する当該基は水素原子を表し、n2が0である場合後述するM2に連結する当該基は水素原子を表す。
n3は1から1000までの整数を表すが、n3は1から10までの整数を表すことが好ましく、n3は1から5までの整数を表すことがより好ましく、n3は1から3までの整数を表すことがさらに好ましく、n3は1又は2を表すことが特に好ましい。
A:<n1及びn2が0を表しn3が1を表す>か、
B:<n1が1を表しn2が0を表しn3が1を表す>か、
C:<n1が0を表しn2及びn3が1を表す>か、
D:<n1及びn2が0を表しn3が2から1000を表す>場合が、逆分散性を良好に示すため特に好ましい。
以下に、特に好ましい形態である上記A:〜D:の形態に分けて、各基について説明する。
<<n1及びn2が0を表しn3が1を表す>>化合物
<W1−A11>
<n1及びn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の表面硬度、紫外線照射後における外観を重視する場合、一般式(I)において、W1が下記の式(I−W11)
<W1−A12>
<n1及びn2が0を表しn3が1を表す>化合物において、重合性組成物の保存安定性、フィルム状の重合物を作製した際の配向ムラ、紫外線照射後における配向欠陥を重視する場合、一般式(I)において、W1が下記の式(I−W12)
<W1−A13>
<n1及びn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の膜厚均一性、密着性を重視する場合、一般式(I)において、W1が下記の式(I−W13)
式(B−3−2)、式(B−4−1)、式(B−8−7)、式(B−12−4)、単結合から選ばれる基がさらに好ましい。
<W1−A14>
<n1及びn2が0を表しn3が1を表す>化合物において、重合性組成物に添加した際の保存安定性、フィルム状の重合物を作製した際のヘイズ値、紫外線照射後における配向欠陥を重視する場合、一般式(I)において、W1が下記の式(I−W14)
<W1−A15>
なお、前記<n1及びn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際のヘイズ値、膜厚均一性を重視する場合、一般式(I)において、W1が下記の式(I−W18)
<M2−A1>
<n1及びn2が0を表しn3が1を表す>化合物において、重合性組成物に添加した際の保存安定性、フィルム状の重合物を作製した際のヘイズ値、膜厚均一性、配向ムラ、表面硬度を重視する場合、一般式(I)において、M2が下記の式(I−M21)
<M2−A2>
<n1及びn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の、紫外線照射後における外観、配向欠陥を重視する場合、一般式(I)において、M2が下記の式(I−M22)
<W1−A2>
<n1及びn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の、紫外線照射後における外観、配向欠陥を重視する場合、一般式(I)において、W1が下記の式(I−W19)
<M2−A3>
<n1及びn2が0を表しn3が1を表す>化合物において、重合性組成物に添加した際の保存安定性、フィルム状の重合物を作製した際の膜厚均一性、紫外線照射後における配向欠陥を重視する場合、一般式(I)において、M2が下記の式(I−M23)
<W1−A3>
<n1及びn2が0を表しn3が1を表す>化合物において、重合性組成物に添加した際の保存安定性、フィルム状の重合物を作製した際の膜厚均一性、紫外線照射後における配向欠陥を重視する場合、一般式(I)において、W1が下記の式(I−W20)
<R3及びR4>
<n1及びn2が0を表しn3が1を表す>化合物においては、上記に示すM2、W1を適宜選択することが好ましく、R3及びR4は、以下の基を用いることが好ましい。
<<n1が1を表しn2が0を表しn3が1を表す>>化合物
<W1−B11>
<n1が1を表しn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の配向ムラ及び表面硬度を重視する場合、一般式(I)において、W1が、下記の式(I−W15)
<W1−B2>
<n1が1を表しn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の表面硬度及び密着性を重視する場合、一般式(I)において、W1が、下記の式(I−W21)
<W1−B3>
<n1が1を表しn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の密着性、紫外線照射後における外観を重視する場合、一般式(I)において、W1が、下記の式(I−W22)
上記式(V−8)、式(V−9)、−COO−、−OCO−を表すことがさらに好ましい。
<M1−B、M2−B>
<n1が1を表しn2が0を表しn3が1を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際の配向ムラ、表面硬度又は密着性が良好であるので、一般式(I)において、M1が下記の式(I−M14)、M2が下記の式(I−M24)
上記式(I−M14)、上記式(I−M24)において、T14及びT24は、各々独立して下記の式(T−1)から式(T−22)
<M1−B11、M2−B11>
フィルム状の重合物を作製した際の配向ムラ及び表面硬度を重視する場合、上記式(I−M14)中T14は上記のものを表し、上記式(I−M24)中T24が下記の式(T2−1)から式(T2−10)
<M1−B2>
また、フィルム状の重合物を作製した際の表面硬度、密着性を重視する場合、上記式(I−M14)中T14は上記<M1−B、M2−B>に記載のものを表し、上記式(I−M24)中T24が下記の式(T2−11)から式(T2−27)
さらに、上記式(I−M24)中T24が下記の式(T2−35)から式(T2−41)
<M1−B3>
さらに、フィルム状の重合物を作製した際の密着性、紫外線照射後における外観を重視する場合、上記式(I−M14)中T14は上記のものを表し、T24が置換されていても良い炭素原子数1から80の非環状基を表すことが好ましく、当該非環状基の任意の炭素原子はヘテロ原子に置換されていても良い。
を表すことが好ましく、下記式(T−22−1)又は式(T−22−2)
<R1、R2、R3、R4>
一方、前記<n1が1を表しn2が0を表しn3が1を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際の配向ムラ、表面硬度又は密着性が良好であるので、一般式(I)において、上記に示すM1、M2、W1を適宜選択することが好ましく、R1〜R4は、以下の基を用いることが好ましい。
また、<n1が1を表しn2が0を表しn3が1を表す>化合物において、フィルム状の重合物を作製した際の配向ムラ、表面硬度を重視する場合、一般式(I)において、R2及びR3が上記式(I−R)で表される基を表し、R1及びR4が上記R5で表される基を表すことが好ましく、この場合、P、S、X、k及びR5は、それぞれ上記<<R1、R2、R3、R4>>の部分に示した好ましい基及び数値が適応される。
<<n1が0を表しn2及びn3が1を表す>>化合物
<M2−C>
さらに、前記<n1が0を表しn2及びn3が1を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際の膜厚均一性、表面硬度及び/又は紫外線照射後における配向欠陥が良好であるので、一般式(I)において、M2が下記の式(I−M2C)
<M2−C11、M2−C12>
フィルム状の重合物を作製した際の膜厚均一性を重視する場合、上記の式(I−M2C)中T2Cは下記の式(T2−C−1)から式(T2−C−12)
<M2−C2>
また、組成物の保存安定性、フィルム状の重合物を作製し紫外線照射後の配向欠陥を重視する場合、上記の式(I−M2C)中T2Cは下記の式(T2−C−13)から式(T2−C−42)
<M2−C3>
また、フィルム状の重合物を作製した際の表面硬度、紫外線照射後の配向欠陥を重視する場合、上記の式(I−M2C)中T2Cは置換されていても良い炭素原子数1から80の非環状基を表すことが好ましく、当該非環状基の任意の炭素原子はヘテロ原子に置換されていても良い。
<W1−M2−W2−C1>
<n1が0を表しn2及びn3が1を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際の膜厚均一性が高く、表面硬度が高く及び/又は紫外線照射後における配向欠陥が生じにくいので、一般式(I)において、M2は、上記<M2−C11、M2−C12>に示された基を用いることが好ましいが、W1−M2−W2で表される基(但し、当該M2は任意の位置においてR3及びR4と連結する。)が下記の式(I−W16−1)又は式(I−W16−2)
<W1−M2−W2−C2>
<n1が0を表しn2及びn3が1を表す>化合物において、組成物の保存安定性、フィルム状の重合物を作製し紫外線照射した際の配向欠陥を重視する場合、W1及びW2で表される基としては、上記<<W1、W2>>に記載の一般式(I−W1)、及び一般式(I−W2)うち、原料の入手容易さ及び合成の容易さの観点から選択される基が好ましい。
<W1−M2−W2−C3>
<n1が0を表しn2及びn3が1を表す>化合物において、フィルム状の重合物を作製した際の表面硬度、紫外線照射した際の配向欠陥を重視する場合、W1及びW2で表される基としては、上記<<W1、W2>>に記載の原料の入手容易さ及び合成の容易さの観点から選択される基が好ましい。
<R3、R4>
<n1が0を表しn2及びn3が1を表す>化合物においては、上記に示すM2、W1、W2を適宜選択することが好ましく、R3〜R4は、それぞれ以下の基を用いることが好ましい。
<<n1及びn2が0を表しn3が2から1000を表す>>化合物
<W1−D1>
<n1及びn2が0を表しn3が2を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際の膜厚均一性又は密着性が良好であるので、一般式(I)において、W1が下記の式(I−W17−1)又は式(I−W17−2)
<W1−D2>
<n1及びn2が0を表しn3が2を表す>化合物において、フィルム状の重合物を作製した際のヘイズ、密着性を重視する場合、W1で表される基としては、上記<<W1、W2>>に記載の一般式(I−W1)のうち、原料の入手容易さ及び合成の容易さの観点から選択される基が好ましい。
<W1−D3>
<n1及びn2が0を表しn3が2を表す>化合物において、フィルム状の重合物を作製した際のヘイズ、表面硬度を重視する場合、W1及びW2で表される基としては、上記<<W1、W2>>に記載の一般式(I−W1)のうち、原料の入手容易さ及び合成の容易さの観点から選択される基が好ましい。
<−(M2)2−>
<n1及びn2が0を表しn3が2を表す>化合物は、化合物の構造上フィルム状の重合物を作製した際のヘイズ値、膜厚均一性又は密着性が良好であるので、一般式(I)において、−(M2)2−が下記の一般式(I−M3)
<−(M2)2−D1>
<n1及びn2が0を表しn3が2を表す>化合物において、組成物の保存安定性、フィルム状の重合物を作製した際の密着性、紫外線照射後の外観を重視する場合若しくはフィルム状の重合物を作製した際の膜厚均一性、配向ムラを重視する場合、上記一般式(I−M3)中、T3及びT4は、各々独立して、式(T2−1)から式(T2−10)
<−(M2)2−D2>
<n1及びn2が0を表しn3が2を表す>化合物において、フィルム状の重合物を作製した際のヘイズ、密着性を重視する場合、上記一般式(I−M3)中、T3は、各々独立して、下記の式(T2−11)から式(T2−27)
上記一般式(I−M3)中、T4は上記式(T2−1)から式(T2−10)又は式(T2−11)から式(T2−34)から選ばれる基を表すことが好ましい。
<−(M2)2−D3>
<n1及びn2が0を表しn3が2を表す>化合物において、フィルム状の重合物を作製した際のヘイズ、表面硬度を重視する場合、T3は置換されていても良い炭素原子数1から80の非環状基を表すことが好ましく、当該非環状基の任意の炭素原子はヘテロ原子に置換されていても良い。
<R3、R4>
<n1及びn2が0を表しn3が2を表す>化合物においては、上記に示すM2、W1を適宜選択することが好ましく、R3〜R4は、それぞれ以下の基を用いることが好ましい。
R3が式(I−R)
Mzは下記の式(M−z−1)から式(M−z−8)
Rz1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、シアノ基、ニトロ基、イソシアノ基、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−、−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。Rz1は液晶性及び合成の容易さの観点から水素原子、フッ素原子、塩素原子、シアノ基、若しくは、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−、−COO−、−OCO−、−O−CO−O−によって置換されても良い炭素原子数1から12の直鎖又は分岐アルキル基を表すことが好ましく、水素原子、フッ素原子、塩素原子、シアノ基、若しくは、炭素原子数1から12の直鎖アルキル基又は直鎖アルコキシ基を表すことがより好ましく、水素原子、炭素原子数1から12の直鎖アルキル基又は直鎖アルコキシ基を表すことがよりさらに好ましく、炭素原子数1から12の直鎖アルキル基又は直鎖アルコキシ基を表すことが特に好ましい。
Gzは下記の式(G−z−1)又は式(G−z−2)
Wz1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の基を表すが、当該基は無置換であるか又は1つ以上のLWzによって置換されても良く、LWz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いが、LWz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、
Wz2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、Wz2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LWzによって置換されても良く、また、Wz1及びWz2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、
kzは0から8の整数を表す。液晶性、原料の入手容易さ及び合成の容易さの観点から0から4の整数を表すことが好ましく、0から2の整数を表すことがより好ましく、0又は1を表すことがさらに好ましく、1を表すことが特に好ましい。mz1及びmz2は各々独立して0から5の整数を表すが、mz1+mz2は1から5の整数を表す。液晶性、合成の容易さ及び保存安定性の観点から、mz1及びmz2は各々独立して1から4の整数を表すことが好ましく、1から3の整数を表すことがより好ましく、1又は2を表すことが特に好ましい。mz1+mz2は1から4の整数を表すことが好ましく、2又は3を表すことが特に好ましい。)で表される化合物であることが好ましく、下記の一般式(I−z1−A)から一般式(I−z1−D)
Wz21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−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、若しくは、−(Xz4−Sz4)kz−Pz4で表される基から選ばれる基を表す。)で表される化合物が好ましい。Wz1の好ましい構造は、前記と同様である。
(実施例1)式(A11−1)で表される化合物の製造
MS(m/z):859[M++1]
(実施例2)式(A11−2)で表される化合物の製造
MS(m/z):794[M++1]
(実施例3)式(A12−1)で表される化合物の製造
MS(m/z):918[M++1]
(実施例4)式(A13−2)で表される化合物の製造
MS(m/z):1192[M++1]
(実施例5)式(A14−1)で表される化合物の製造
MS(m/z):834[M++1]
(実施例6)式(A14−2)で表される化合物の製造
MS(m/z):847[M++1]
(実施例7)式(A141−1)で表される化合物の製造
転移温度(昇温5℃/分):C 105 N 150 I
1H NMR(CDCl3)δ 0.93(t,3H),1.10(q,2H),1.25(m,2H),1.37(m,3H),1.46−1.59(m,6H),1.74(quin,2H),1.81−1.98(m,6H),2.56(m,1H),4.03(t,2H),4.19(t,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.87(d,2H),7.08(t,1H),7.12(d,1H),7.20(t,1H),7.28(dd,1H),7.45(dd,1H),7.58(d,1H),7.84(s,1H),8.06(m,3H)ppm.
MS(m/z):668[M++1]
(実施例8)式(A141−2)で表される化合物の製造
転移温度(昇温5℃/分):C 79 N 137 I
1H NMR(CDCl3)δ 1.01(t,3H),1.48(m,4H),1.69−1.79(m,6H),2.67(t,2H),3.95(m,2H),4.18(t,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.83(m,2H),7.03−7.68(m,10H),7.97−8.30(m,4H)ppm.
MS(m/z):662[M++1]
(実施例9)式(A141−3)で表される化合物の製造
転移温度(昇温5℃/分):C 156 N 173 I
1H NMR(CDCl3)δ 1.02(t,3H),1.40−1.92(m,12H),4.00(br,2H),4.09(t,2H),4.18(t,2H),5.82(dd,1H),6.13(dd,1H),6.41(dd,1H),6.64−6.13(m,14H),8.19(d,2H)ppm.
MS(m/z):736[M++1]
(実施例10)式(A141−4)で表される化合物の製造
転移温度(昇温5℃/分):C 79 N 112 I
1H NMR(CDCl3)δ 0.96(t,3H),1.43−1.78(m,8H),1.87(quin,2H),2.60(t,2H),4.08(t,2H),4.20(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),7.01(d,2H),7.09(t,1H),7.17−7.29(m,7H),7.37(d,1H),7.60(d,1H),7.91(s,2H),8.21(d,2H)ppm.
MS(m/z):662[M++1]
(実施例11)式(A141−5)で表される化合物の製造
転移温度(昇温5℃/分):C 178 N 180 I
1H NMR(CDCl3)δ 1.44−1.60(m,4H),1.74(quin,2H),1.86(quin,2H),3.89(s,3H),4.07(t,2H),4.20(t,2H),5.83(dd,1H),6.14(dd,1H),6.42(dd,1H),6.99(m,3H),7.09(t,1H),7.13(d,1H),7.19(t,1H),7.27(d,2H),7.44(d,1H),7.54(d,1H),7.60(d,1H),8.03(s,1H),8.17(d,4H)ppm.
MS(m/z):694[M++1]
(実施例12)式(A141−6)で表される化合物の製造
転移温度(昇温5℃/分):C 62 N 95 poly
1H NMR(CDCl3)δ 0.89(t,3H),1.33(m,4H),1.43−1.57(m,2H),1.61(quin,2H),1.73(quin,2H),1.85(quin,2H),2.59(t,2H),2.97(m,4H),4.03(t,2H),4.19(m,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.87(d,2H),7.04−7.29(m,8H),7.44(d,1H),7.58(d,1H),7.85(s,1H),8.05(m,3H)ppm.
MS(m/z):718[M++1]
(実施例13)式(A141−7)で表される化合物の製造
転移温度(昇温5℃/分):C 147 N 153 I
1H NMR(CDCl3)δ 0.93(t,3H),1.37(m,4H),1.46−1.59(m,4H),1.63−1.78(m,4H),1.86(quin,2H),2.68(t,2H),4.07(t,2H),4.19(t,2H),5.84(dd,1H),6.14(dd,1H),6.42(dd,1H),7.00(d,2H),7.09(t,1H),7.12(d,1H),7.19(t,1H),7.23−7.33(m,3H),7.45(d,1H),7.61(d,1H),7.80(d,1H),8.07(s,1H),8.14−8.23(m,4H)ppm.
MS(m/z):734[M++1]
(実施例14)式(A141−8)で表される化合物の製造
転移温度(昇温5℃/分):C 169 N 178 I
1H NMR(CDCl3)δ 1.43(t,3H),1.47−1.60(m,4H),1.75(quin,2H),1.87(m,2H),3.99(q,2H),4.08(t,2H),4.20(t,2H),5.83(dd,1H),6.14(dd,1H),6.42(dd,1H),6.85(d,2H),7.01(d,2H),7.08(t,1H),7.14(t,1H),7.20(t,3H),7.25(dd,1H),7.35(d,1H),7.60(d,1H),7.90(d,1H),7.94(s,1H)8.21(d,2H)ppm.
MS(m/z):664[M++1]
(実施例15)式(A141−9)で表される化合物の製造
転移温度(昇温5℃/分):C 98 N 157 I
1H NMR(CDCl3)δ 0.94(t,3H),1.31−1.76(m,12H),2.66(t,2H),3.89(t,2H),4.12(t,2H),5.80(dd,1H),6.13(dd,1H),6.41(dd,1H),6.50−8.20(m,16H)ppm.
MS(m/z):700[M++1]
(実施例16)式(A141−10)で表される化合物の製造
転移温度(昇温5℃/分):C 164 I
1H NMR(DMSO−d6)δ 0.94(t,3H),1.65(q,2H),2.15(t,2H),2.63(t,2H),4.22(t,2H),4.30(t,2H),5.96(d,1H),6.20(q,1H),6.36(d,1H),7.10(t,1H),7.18(d,2H),7.28(t,1H),7.35(d,2H),7.52(d,2H),7.63(d,2H),7.23(t,2H),8.15(t,3H),8.25(s,1H)ppm.
MS(m/z):620[M++1]
(実施例17)式(A141−11)で表される化合物の製造
転移温度(昇温5℃/分):C 155 N 158 I
1H NMR(CDCl3)δ 1.02(t,3H),1.73(q,3H),1.86(m,4H),2.68(t,2H),3.96(m,2H),4.24(m,2H),5.85(d,1H),6.14(dd,1H),6.43(d,1H),6.80(m,2H),7.08−7.33(m,5H),7.44(m,1H),7.59(m,4H),8.01(m,2H),8.23(m,2H)ppm.
MS(m/z):634[M++1]
(実施例18)式(A141−12)で表される化合物の製造
転移温度(昇温5℃/分):C 154 I
1H NMR(CDCl3)δ 0.95(tt,3H),1.63(m,2H),2.24(quin,2H),2.59(m,2H),4.19(t,2H),4.41(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.02(d,2H),7.09−7.28(m,8H),7.37(d,1H),7.60(d,1H),7.91(m,2H),8.22(d,2H)ppm.
MS(m/z):620[M++1]
(実施例19)式(A141−13)で表される化合物の製造
転移温度(昇温5℃/分):C 146 N 149 I
1H NMR(CDCl3)δ 0.95(t,3H),1.63(m,2H),1.93(m,4H),2.58(t,2H),4.12(t,2H),4.28(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.01(d,2H),7.07−7.29(m,8H),7.36(d,1H),7.60(d,1H),7.91(m,2H),8.21(d,2H)ppm.
MS(m/z):634[M++1]
(実施例20)式(A141−14)で表される化合物の製造
転移温度(昇温、降温5℃/分):C 128 (N 80) I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(m,2H),1.20−1.50(m,11H),1.66(quin,2H),1.78(quin,2H),1.89(m,4H),2.51(tt,1H),2.73(t,2H),2.91(t,2H),3.95(t,2H),4.14(t,2H),5.81(dd,1H),6.12(dd,1H),6.39(dd,1H),6.85(d,2H),6.93(d,1H),7.09(d,2H),7.14(t,1H),7.21(dd,1H),7.33(t,1H),7.54(d,1H),7.58(s,1H),7.66(d,1H),7.80(d,1H)ppm.
MS(m/z):696[M++1]
(実施例21)式(A141−15)で表される化合物の製造
MS(m/z):794[M++1]
(実施例22)式(A141−16)で表される化合物の製造
転移温度(昇温5℃/分):C 117 N 220 I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(q,2H),1.24−2.06(m,27H),2.35(m,2H),2.55(t,1H),3.95(t,2H),4.18(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),6.88(d,2H),6.98(m,3H),7.19−7.26(m,2H),7.35(m,1H),7.51(m,1H),7.68(m,1H),7.89(m,1H),8.08(m,1H)ppm.
MS(m/z):794[M++1]
(実施例23)式(A141−17)で表される化合物の製造
転移温度(昇温5℃/分):C 90 S 156 N
1H NMR(CDCl3)δ 0.92(t,3H),1.09(m,2H),1.31(m,13H),1.48(m,6H),1.74(t,3H),1.81(t,3H),1.93(m,6H),2.54(t,1H),2.72(t,1H),3.94(t,2H),4.18(t,2H),5.81(d,1H),6.13(q,1H),6.41(d,1H),6.41(d,1H),6.88(d,2H),6.96(d,2H),7.20(t,1H),7.26(d,1H),7.45(d,1H),7.57(d,1H),7.84(s,1H),8.07(d,3H)ppm.
MS(m/z):822[M++1]
(実施例24)式(A141−18)で表される化合物の製造
転移温度(昇温5℃/分):C 64−77 N >220 I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(q,2H),1.23(m,2H),1.37(m,3H),1.48−1.60(m,6H),1.74(quin,2H),1.83−1.90(m,4H),1.97(d,2H),2.56(tt,1H),4.07(t,2H),4.19(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),7.00(d,2H),7.11(q,1H),7.12(d,1H),7.19−7.31(m,4H),7.46(d,1H),7.61(d,1H),7.85(d,1H),8.09(s,1H),8.17(m,4H)ppm.
MS(m/z):788[M++1]
(実施例25)式(A141−19)で表される化合物の製造
転移温度(昇温5℃/分):C 190 N 260 I
1H NMR(CDCl3)δ 0.89(t,1H),1.05(t,2H),1.31(q,2H),1.50(m,6H),1.74,(m,15H),2.54(t,1H),4.03(t,2H),4.19(t,2H),5.81(d,1H),6.13(q,1H),6.41(d,1H),6.43(d,1H),7.09(d,2H),7.11(d,2H),7.20(t,1H),7.26(d,1H),7.45(d,1H),7.57(d,1H),7.84(s,1H),8.07(d,3H)ppm.
MS(m/z):750[M++1]
(実施例26)式(A141−20)で表される化合物の製造
転移温度(昇温5℃/分):C 75−108 N 180 I
1H NMR(CDCl3)δ 0.94(t,3H),1.10(m,2H),1.25(m,2H),1.29−1.57(m,11H),1.80−2.08(m,6H),2.30(m,2H),2.54(m,1H),3.67−3.78(m,6H),3.85(t,2H),4.11(t,2H),4.32(t,2H),5.84(dd,1H),6.15(dd,1H),6.40(dd,1H),6.82−7.00(m,4H),7.08−7.60(m,4H),7.65−8.10(m,3H)、8.40(s,1H)、11.6(s,1H)ppm.
LCMS:826[M+1]
(実施例27)式(A141−21)で表される化合物の製造
転移温度(昇温5℃/分):C 89−123 I
1H NMR(CDCl3)δ 1.05(t,3H),1.70(m,2H),2.70(t,2H),3.58−3.73(m,6H),3.75(t,2H),4.02(t,2H),4.27(t,2H),5.84(dd,1H),6.12(dd,1H),6.42(dd,1H),6.65(d,2H),7.00(d,2H),7.15−7.45(m,5H),7.51−7.70(m,5H),7.78(dd,1H),8.17(s,1H),11.7(s,1H)ppm.
LCMS:694[M+1]
(実施例28)式(A141−22)で表される化合物の製造
転移温度:C ? N 150 I
1H NMR(CDCl3)δ 1.40−1.82(m,24H),2.04−2.20(m,8H),2.35−2.49(m,4H),3.02(t,2H),3.92(t,2H),3.95(t,2H),4.17(t,2H),4.18(t,2H),4.36(t,2H),5.82(dd,1H),5.82(dd,1H),6.12(dd,1H),6.13(dd,1H),6.40(dd,1H),6.40(dd,1H),6.82−6.90(m,6H),6.97−7.04(m,3H),7.17(m,1H),7.26(m,1H),7.35(t,1H),7.49(d,1H),7.69(d,1H),7.93(s,1H),8.07(s,1H)ppm.
(実施例29)式(A141−23)で表される化合物の製造
転移温度:C 145 N 207 I
1H NMR(CDCl3)δ 1.47−1.87(m,16H),3.17(t,2H),4.05(t,2H),4.06(t,2H),4.18(t,2H),4.19(t,2H),4.62(t,2H),5.82(dd,1H),5.82(dd,1H),6.13(dd,1H),6.13(dd,1H),6.41(dd,1H),6.41(dd,1H),6.96(m,4H),7.09(m,1H),7.19−7.38(m,7H),7.45(d,1H),7.61(d,1H),7.96(m,1H),8.05−8.18(m,7H),8.22(d,2H)ppm.
(実施例30)式(A141−24)で表される化合物の製造
転移温度:S 60 I
1H NMR(CDCl3)δ:1.40−1.60(p,8H),1.6(br,1H),1.65−1.80(p,4H),1.80−1.97(p,4H),3.15(t,2H),4.01(t,2H),4.17(t,2H),4.31(t,2H),4.40(t,2H),4.57(t,2H),5.81−5.85(d+d,2H),6.08−6.18(m,2H),6.37−6.46(d+d,2H),6.87(d,2H),6.96(d,2H),7.12−7.18(m,2H),7.34(d,1H),7.48(d,1H),7.58(d,1H),7.99−8.02(s+d,5H),8.12(d,2H)ppm.
LC−MS:m/z 862.60[M+]
(実施例31)式(A141−25)で表される化合物の製造
転移温度:C 118 I
1H NMR(CDCl3)δ 2.11(quin,2H),2.22(quin,2H),3.15(t,2H),4.01(t,2H),4.14(t,2H),4.31(t,2H),4.40(t,2H),4.57(t,2H),5.83(m,2H),6.13(m,2H),6.41(m,2H),6.88(m,4H),7.09(m,1H),7.16−7.23(m,2H),7.34(m,1H),7.45(m,1H),7.55(m,1H),7.97−8.09(m,6H)ppm.
(実施例32)式(A141−26)で表される化合物の製造
転移温度:C 61−67 (N 40) I
1H NMR(CDCl3)δ 1.42−1.82(m,16H),2.83−3.09(m,8H),3.97(m,4H),4.17(m,4H),5.84(d,2H),6.15(dd,2H),6.43(d,2H),6.86−6.92(m,4H),7.04(m,2H),7.15−7.23(m,5H),7.36(t,1H),7.42(s,1H),7.57(d,1H),7.68(m,2H)ppm.
(実施例33)式(A141−27)で表される化合物の製造
転移温度:C 106 S 196 N 203 I
1H NMR(CDCl3)δ:1.41−1.61(p,8H),1.65−1.80(p,4H),1.7(br,1H),1.80−1.97(p,4H),4.02(t,2H),4.17(t,2H),5.82(d,2H),6.10−6.18(dd,2H),6.39−6.44(s+d,3H),6.93(dd,4H),7.09(t,2H),7.23(s,1H),7.30(d,1H),7.43(d,1H),7.50−7.58(p,4H),7.75−7.89(p,3H),8.10(s,1H)ppm.
LC−MS:m/z 885.61[M+]
(実施例34)式(A141−28)で表される化合物の製造
転移温度:C 141 I
1H NMR(CDCl3)δ 1.41−1.50(m,8H),1.64−1.81(m,8H),3.88(t,2H),3.91(t,2H),4.16(m,6H),4.26−4.35(m,6H),5.81(dd,1H),5.81(dd,1H),6.12(dd,1H),6.12(dd,1H),6.40(dd,1H),6.40(dd,1H),6.79−6.98(m,10H),7.13(t,1H),7.32(t,1H),7.58(m,2H),7.65(d,1H),8.22(s,1H)ppm.
(実施例35)式(A141−29)で表される化合物の製造
相転移温度(昇温過程):C 180 N >220 I
1H NMR (CDCl3):1.42−1.60(m,8H), 1.68−1.91(m,8H),3.95(m,2H),4.07(t,2H),4.16−4.22(m,4H),5.83(dd,2H),6.09−6.18(m,2H),6.42(dd,2H),6.82(br,2H),7.00(d,2H),7.09(br,1H),7.21(br,1H),7.33(m,3H),7.45(br,1H),7.62(m,2H),7.70(d,2H),8.02(br,2H),8.19(d,3H),8.25(br,1H)ppm.
(実施例36)式(A141−30)で表される化合物の製造
相転移温度(昇温過程):C 107 N 217 I
1H NMR (CDCl3):1.52(m,8H),1.74(quin,4H),1.86(quin,4H),4.07(td,4H),4.20(td,4H),5.84(d,2H),6.14(dd,2H),6.42(d,2H),6.99(d,4H),7.11(t,1H),7.21−7.40(m,8H),7.62(d,1H),7.93(m,2H),8.19(dd,4H)ppm.
(実施例37)式(A141−31)で表される化合物の製造
相転移温度(昇温過程):C 60−80 N 206 I
1H NMR (CDCl3):1.44−1.60(m,9H),1.66−1.90(m,13H),2.07(m,2H),2.29(m,2H),2.68(m,1H),4.03(td,4H),4.19(td,4H),5.07(m,1H),5.84(dt,2H),6.13(dd,2H),6.42(dd,2H),6.86(d,2H),6.93(d,2H),7.06−7.22(m,3H),7.30(dd,1H),7.45(d,1H),7.63(d,1H),7.90(s,1H),8.04(m,4H),8.11(s,1H)ppm.
(実施例38)式(A141−32)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39)式(A141−33)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40)式(A142−1)で表される化合物の製造
転移温度(昇温、降温5℃/分):C 128 (N 80) I
1H NMR(CDCl3)δ 1.00(t,3H),1.47−1.60(m,4H),1.73(m,4H),1.87(quin,2H),2.67(t,2H),3.55(s,3H),4.08(t,2H),4.20(t,2H),5.84(dd,1H),6.14(dd,1H),6.42(dd,1H),7.02(d,2H),7.13(t,1H),7.25−7.33(m,6H),7.39(d,1H),7.62(dd,2H),7.69(s,1H),7.93(d,1H),8.22(d,2H)ppm.
MS(m/z):696[M++1]
(実施例41)式(A142−2)で表される化合物の製造
転移温度(昇温5℃/分):C 117−122 N 146 I
1H NMR(CDCl3)δ 0.91(m,6H),1.10(q,2H),1.23−1.56(m,18H),1.68−1.81(m,9H),1.94(t,4H),2.32(m,4H),2.56−2.70(m,3H),3.94(t,2H),4.18(t,2H),4.29(t,2H),5.82(dd,1H),6.13(dd,1H),6.40(dd,1H),6.89(d,2H),6.99(m,3H),7.16(t,1H),7.23(dd,1H),7.34(t,1H),7.66−7.72(m,3H),7.90(d,1H)ppm.
MS(m/z):878[M++1]
(実施例42)式(A142−3)で表される化合物の製造
転移温度(昇温5℃/分):C 147−156 N 173 I
1H NMR(CDCl3)δ 0.92(t,3H),1.11(q,2H),1.25(m,2H),1.37−1.55(m,9H),1.71(m,6H),1.78(m,2H),1.94(m,4H),2.33(m,4H),2.56(m,2H),2.70(m,1H),3.72(s,3H),3.94(t,2H),4.17(t,2H),5.82(dd,1H),6.13(dd,1H),6.40(dd,1H),6.88(d,2H),6.98(m,3H),7.17(t,1H),7.24(dd,1H),7.35(t,1H),7.66−7.72(m,3H),7.88(d,1H)ppm.
MS(m/z):808[M++1]
(実施例43)式(A142−4)で表される化合物の製造
転移温度(昇温5℃/分):C 106 N 125 I
1H NMR(CDCl3)δ 0.92(t,3H),1.05−1.83(m,22H),1.93(t,5H),2.33(m,4H),2.55(m,2H),2.71(m、1H),3.30(s,3H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.48(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.88(d,2H),6.99(m,3H),7.17(t,1H),7.23(dd,1H),7.34(t,1H),7.66(d,1H),7.71(d,1H),7.89(d,1H),8.02(s,1H)ppm.
(実施例44)式(A142−5)で表される化合物の製造
転移温度(昇温5℃/分):C 131 I
1H NMR(CDCl3)δ 0.88−0.94(m,6H),1.10(m,2H),1.22−1.52(m,13H),1.72(m,6H),1.94(t,4H),2.32(m,4H),2.53−2.62(m,3H),3.69−3.77(m,6H),3.86(t,2H),4.12(t,2H),4.27−4.34(m,4H),5.83(dd,1H),6.16(dd,1H),6.43(dd,1H),6.91(d,2H),6.97−7.02(m,3H),7.16(t,1H),7.23(dd,1H),7.33(t,1H),6.66−7.72(m,3H),7.90(d,1H)ppm.
LCMS:910[M+1]
(実施例45)式(A142−6)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46)式(A142−7)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47)式(A142−8)で表される化合物の製造
1H NMR(CDCl3)δ 0.92(t,3H),1.05−1.83(m,32H),1.93(t,5H),2.33(m,4H),2.55(m,2H),2.71(m、1H),3.30(s,3H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.48(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.88(d,2H),6.99(m,3H),7.17(t,1H),7.23(dd,1H),7.34(t,1H),7.66(d,1H),7.71(d,1H),7.89(d,1H),8.02(s,1H)ppm.
LCMS:978[M+1]
(実施例48)式(A142−9)で表される化合物の製造
転移温度(昇温5℃/分):C 90 S 218 N 265 I
1H NMR(CDCl3)δ 0.88(m,6H),1.01−1.19(m,8H),1.32−1.45(m,6H),1.71−1.76(m,6H),1.88−1.99(m,3H),2.17(m,12H),2.31(m,4H),2.53(m,2H),2.67(m,1H),3.70−3.76(m,6H),3.85(t,2H),4.11(t,2H),4.31(m,4H),5.82(d,2H),6.15(q,2H),6.43(d,2H),6.92(m,5H),7.14−7.26(m,2H),7.33(t,1H),7.68(m,3H),7.88(s,1H)ppm.
(実施例49)式(A142−10)で表される化合物の製造
転移温度:C 113−123 (N 113) I
1H NMR(CDCl3)δ 1.40−1.82(m,24H),2.09−2.17(m,4H),2.33(m,5H),2.47(m,1H),2.61(m,1H),2.71(m,1H),3.03(t,2H),3.74(s,3H),3.93(t,2H),3.94(t,2H),4.17(t,2H),4.17(t,2H),4.37(t,2H),5.82(m,2H),6.12(m,2H),6.40(m,2H),6.83−6.90(m,6H),6.98(d,2H),7.04(d,1H),7.16(t,1H),7.25(m,1H),7.34(t,1H),7.66−7.71(m,3H),7.91(d,1H)ppm.
(実施例50)式(A142−11)で表される化合物の製造
転移温度:C 134−139 (N 102) I
1H NMR(CDCl3)δ 0.89(t,3H),1.32−1.56(m,18H),1.70−1.81(m,14H),2.09−2.17(m,4H),2.33(m,5H),2.46(m,1H),2.59(m,1H),2.69(m,1H),3.03(t,2H),3.93(t,2H),3.94(t,2H),4.17(t,2H),4.17(t,2H),4.30(t,2H),4.37(t,2H),5.81(dd,1H),5.82(dd,1H),6.12(dd,1H),6.13(dd,1H),6.40(dd,1H),6.40(dd,1H),6.83−6.89(m,6H),6.98(d,2H),7.05(d,1H),7.15(t,1H),7.24(dd,1H),7.33(t,1H),7.68(dd,2H),7.71(s,1H),7.93(d,1H)ppm.
(実施例51)式(A142−12)で表される化合物の製造
転移温度:C 60−65 I
1H NMR(CDCl3)δ 0.78(t,3H),1.11−1.18(m,6H),1.42−1.59(m,10H),1.68−1.77(m,6H),1.86(quin,2H),3.17(t,2H),3.86(t,2H),4.06(t,2H),4.15−4.21(m,6H),4.58(t,2H),5.82(dd,1H),5.82(dd,1H),6.13(dd,1H),6.13(dd,1H),6.40(dd,1H),6.40(dd,1H),6.84(d,2H),7.00(d,2H),7.14(t,1H),7.18(d,1H),7.29−7.35(m,2H),7.63(m,2H),7.76(s,1H),8.00−8.04(m,3H),8.18(d,2H)ppm.
(実施例52)式(A142−13)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53)式(A142−14)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54)式(A142−15)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55)式(A143−1)で表される化合物の製造
転移温度(昇温速度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56)式(A143−2)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.
LCMS:1156[M+1]
(実施例57)式(A144−1)で表される化合物の製造
相転移温度(昇温過程):C 113 N 171 I
1H NMR (CDCl3):1.48−1.59(m,8H),1.74(m,4H),1.85(m,4H), 4.07(q,4H),4.19(td,4H),5.84(d,2H),6.14(ddd,2H),6.42(dt,2H),7.00(q,4H),7.30(m,4H),7.39−7.46(m,5H),7.51(d,1H),7.61(dd,2H),7.85(d,1H),6.17(d,2H),8.22−8.25(m,3H),8.39(d,1H),8.57(s,1H)ppm.
(実施例58)式(A15−1)で表される化合物の製造
MS(m/z):853[M++1]
(実施例59)式(A2−3)で表される化合物の製造
MS(m/z):908[M++1]
(実施例60)式(A2−5)で表される化合物の製造
MS(m/z):790[M++1]
(実施例61)式(A3−1)で表される化合物の製造
MS(m/z):1097[M++1]
(実施例62)式(B11−1)で表される化合物の製造
MS(m/z):1037[M++1]
(実施例63)式(B11−8)で表される化合物の製造
MS(m/z):1247[M++1]
(実施例64)式(B2−2)で表される化合物の製造
MS(m/z):1543[M++1]
(実施例65)式(B2−6)で表される化合物の製造
MS(m/z):1713[M++1]
(実施例66)式(B2−13)で表される化合物の製造
MS(m/z):1367[M++1]
(実施例67)式(B3−1)で表される化合物の製造
MS(m/z):1541[M++1]
(実施例68)式(C11−2)で表される化合物の製造
MS(m/z):925[M++1]
(実施例69)式(C12−1)で表される化合物の製造
MS(m/z):893[M++1]
(実施例70)式(C2−1)で表される化合物の製造
MS(m/z):1267[M++1]
(実施例71)式(C2−4)で表される化合物の製造
反応容器に式(C2−4−5)で表される化合物、式(C2−4−6)で表される化合物、炭酸セシウム、ジメチルスルホキシドを加え加熱撹拌した。通常の後処理を行った後、カラムクロマトグラフィーにより精製を行い、式(C2−4−7)で表される化合物を得た。
MS(m/z):1163[M++1]
(実施例72)式(C2−16)で表される化合物の製造
MS(m/z):1083[M++1]
(実施例73)式(C3−1)で表される化合物の製造
MS(m/z):1489[M++1]
(実施例74)式(D11−1)で表される化合物の製造
MS(m/z):1113[M++1]
(実施例75)式(D12−1)で表される化合物の製造
MS(m/z):909[M++1]
(実施例76)式(D2−1)で表される化合物の製造
MS(m/z):1253[M++1]
(実施例77)式(D3−1)で表される混合物の製造
MS(m/z):1447[M++1]
(実施例78)式(D4−2)で表される混合物の製造
Mw=271,000、Mn=114,000、Mw/Mn=2.4
上記実施例1から実施例78と同様に、公知の方法を用いて、式(A11−1)から式(D4−4)で表される化合物を製造した。
(実施例79〜345)
本願発明の上記式(A11−1)から式(D4−4)で表される化合物を評価対象の化合物とした。
(実施例346〜612)
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た。得られた塗膜をラビング処理した。ラビング処理は、市販のラビング装置を用いて行った。
〈ヘイズ〉
ヘイズ値は下記式
ヘイズ(%)=Td/Tt×100
(式中、Tdは拡散透過率、Ttは全光線透過率を表す。)で表され、測定にはヘイズ測定装置(日本電色工業株式会社製NHD2000)を用い、作製した10枚の各フィルム上の5カ所において測定を行い、その平均値をとった。
〈膜厚均一性〉
最大膜厚と最小膜厚との差を平均膜厚で除した値(%)を算出した。測定には光干渉膜厚計(大塚電子株式会社製FE−3000)を用い、作製した10枚の各フィルム上の25カ所において測定を行った。
〈配向ムラ〉
偏光顕微鏡観察によって配向ムラの程度を評価した。作製した10枚の各フィルムにおいて観察された配向欠陥の個数を合計した。
〈表面硬度〉
作製した10枚の各フィルム上の5カ所において鉛筆硬度評価(JIS K5400)を行った。
〈密着性〉
作製した10枚の各フィルムについて、碁盤目テープ試験(JIS K5400)による評価を行った。作製した10枚の各フィルムにおいて剥がれの生じた目の数の平均値(%)を評価した。
〈外観〉
作製した10枚の各フィルムにおいて、目視で変色及び剥離がなければA+、変色がわずかに見られるが剥離がなければA−、変色がわずかに見られ、剥離が全体の0.2%以下であればB+、変色がわずかに見られ、剥離が全体の0.3%から1.0%であればB−、変色がわずかに見られ、剥離が全体の1.1%から2.0%であればC+、変色がわずかに見られ、剥離が全体の2.1%以上であればC−、変色がやや強く見られればDとした。
〈配向欠陥〉
作製した10枚の各フィルムにおいて、偏光顕微鏡観察で生じた配向欠陥の数の合計を評価した。
Claims (6)
- 一般式(I)
V2は、それぞれ独立して、下記の式(V−1)から式(V−15)
B1は各々独立して、式(B−1)から式(B−21)
で表されるπ電子が100までの共役系を形成する基を表し、
また、前記R3及びR4は一般式(I−R)
かつ、前記一般式(I)において、
M2が下記の式(I−M21)
T21が下記の式(T2−1)から式(T2−10)
- 請求項1に記載の化合物を含有する組成物。
- 請求項1又は2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3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4記載の重合体を用いた光学異方体。
- 請求項1又は2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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CN108137486B (zh) | 2015-10-23 | 2019-08-13 | Dic株式会社 | 聚合性化合物和光学各向异性体 |
US10919870B2 (en) | 2015-11-09 | 2021-02-16 | Dic Corporation | Polymerizable compound and optically anisotropic body |
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US20170369783A1 (en) | 2017-12-28 |
JP2018109066A (ja) | 2018-07-12 |
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