JPWO2020095900A5 - - Google Patents

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JPWO2020095900A5
JPWO2020095900A5 JP2020556078A JP2020556078A JPWO2020095900A5 JP WO2020095900 A5 JPWO2020095900 A5 JP WO2020095900A5 JP 2020556078 A JP2020556078 A JP 2020556078A JP 2020556078 A JP2020556078 A JP 2020556078A JP WO2020095900 A5 JPWO2020095900 A5 JP WO2020095900A5
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liquid crystal
formula
crystal aligning
aligning agent
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主鎖中に下記式（１）で表される構造を有するポリイミド前駆体及び該ポリイミド前駆体のイミド化重合体からなる群から選ばれる少なくとも１種の重合体を含有する液晶配向剤。
Figure 2020095900000001
 （式中、Ｒ１及びＲ２は、それぞれ独立して、単結合、－Ｏ－、－Ｓ－、－ＮＲ１２－、エステル結合、アミド結合、チオエステル結合、ウレア結合、カーボネート結合、又はカルバメート結合であり、Ｒ１２は、水素原子又はメチル基である。Ａは炭素数１又は２のアルキレン基である。Ｂ１及びＢ２は、同じ構造を有し、下記構造から選ばれる２価の有機基である。）
Figure 2020095900000002
 （式中、Ｒ４は、炭素数１～５のアルキレン基である。Ｒ５は水素原子、メチル基、ヒドロキシ基又はメトキシ基である。） A liquid crystal aligning agent containing at least one polymer selected from the group consisting of a polyimide precursor having a structure represented by the following formula (1) in the main chain and an imidized polymer of the polyimide precursor.
Figure 2020095900000001
(wherein R 1 and R 2 are each independently a single bond, —O—, —S—, —NR 12 —, an ester bond, an amide bond, a thioester bond, a urea bond, a carbonate bond, or a carbamate bond and R 12 is a hydrogen atom or a methyl group, A is an alkylene group having 1 or 2 carbon atoms, B 1 and B 2 have the same structure and are divalent organic compounds selected from the following structures: base.)
Figure 2020095900000002
 (In the formula, R 4 is an alkylene group having 1 to 5 carbon atoms. R 5 is a hydrogen atom, a methyl group, a hydroxy group or a methoxy group.) 前記式（１）において、Ｒ１及びＲ２は、それぞれ独立して、単結合、－Ｏ－、－Ｓ－、－ＮＲ１２－、エステル結合又はアミド結合であり、Ａは、炭素数２のアルキレン基であり、Ｒ４は、炭素数１～３のアルキレン基であり、Ｒ５は、水素原子又はメチル基である、請求項１に記載の液晶配向剤。 In the above formula (1), R 1 and R 2 are each independently a single bond, —O—, —S—, —NR 12 —, an ester bond or an amide bond, and A is a 2. The liquid crystal aligning agent according to claim 1, which is an alkylene group, R 4 is an alkylene group having 1 to 3 carbon atoms, and R 5 is a hydrogen atom or a methyl group. 前記ポリイミド前駆体が、下記式（２）の構造単位を含有する重合体である請求項１又は２に記載の液晶配向剤。
Figure 2020095900000003
 （式中、Ｘ１は、下記式（Ｘ１－１）及び式（Ｘ１－２）で表される構造からなる群から選ばれる少なくとも１種である。Ｙ１は前記式（１）で表される２価の有機基であり、Ｒ３は水素原子又は炭素数１～５のアルキル基である。Ｚ１及びＺ２は、それぞれ独立して、水素原子、又は置換基を有してもよい、炭素数１～１０のアルキル基、炭素数２～１０のアルケニル基若しくは炭素数２～１０のアルキニル基である。）
Figure 2020095900000004
 The liquid crystal aligning agent according to claim 1 or 2, wherein the polyimide precursor is a polymer containing a structural unit of the following formula (2).
Figure 2020095900000003
 (In the formula, X 1 is at least one selected from the group consisting of structures represented by the following formulas (X1-1) and (X1-2). Y 1 is represented by the above formula (1). R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and Z 1 and Z 2 are each independently a hydrogen atom or may have a substituent , an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms.)
Figure 2020095900000004
 前記ポリイミド前駆体が、ジアミン成分とテトラカルボン酸成分とを重合反応させることにより得られる、請求項１～３のいずれか１項に記載の液晶配向剤。 The liquid crystal aligning agent according to any one of claims 1 to 3, wherein the polyimide precursor is obtained by polymerizing a diamine component and a tetracarboxylic acid component. 前記ポリイミド前駆体が、ジアミン成分とテトラカルボン酸成分とを重合反応させることにより得られる重合体であって、Ｂ１及びＢ２が、同じ構造を有し、下記構造から選ばれる２価の有機基である前記式（１）の構造の両端にアミノ基が結合したジアミンを原料として用いる、請求項４に記載の液晶配向剤。The polyimide precursor is a polymer obtained by polymerizing a diamine component and a tetracarboxylic acid component, wherein B1 and B2 have the same structure and are divalent organic groups selected from the following structures: 5. The liquid crystal aligning agent according to claim 4, wherein a diamine in which amino groups are bonded to both ends of a certain structure of formula (1) is used as a raw material.
Figure 2020095900000005
Figure 2020095900000005
 前記ジアミン成分が、以下から選ばれる少なくとも１種のジアミンを含む、請求項４に記載の液晶配向剤。
Figure 2020095900000006
Figure 2020095900000007
Figure 2020095900000008
 （Ｒ５及びＲ１２は、前記式（１）と同じである。） The liquid crystal aligning agent according to claim 4, wherein the diamine component contains at least one diamine selected from the following.
Figure 2020095900000006
Figure 2020095900000007
Figure 2020095900000008
 (R 5 and R 12 are the same as in formula (1) above.) 前記ジアミン成分が、以下から選ばれる少なくとも１種のジアミンを含む、請求項６に記載の液晶配向剤。The liquid crystal aligning agent according to claim 6, wherein the diamine component contains at least one diamine selected from the following.
Figure 2020095900000009
Figure 2020095900000009
 （Ｒ (R ５5 及びＲand R １２12 は、前記式（１）と同じである。）is the same as the above formula (1). ) 前記ポリイミド前駆体が、前記式（２）で表される構造単位を、全構造単位に対して、２０～１００モル％有する、請求項３～７のいずれか１項に記載の液晶配向剤。 The liquid crystal aligning agent according to any one of claims 3 to 7 , wherein the polyimide precursor has 20 to 100 mol% of the structural units represented by the formula (2) with respect to all structural units. 前記式（２）において、Ｘ１が、下記式（Ｘ１－２）である、請求項３～８のいずれか１項に記載の液晶配向剤。
Figure 2020095900000010
 The liquid crystal aligning agent according to any one of claims 3 to 8, wherein in the formula (2), X 1 is the following formula (X1-2).
Figure 2020095900000010
 前記式（２）において、Ｒ３は、水素原子又はメチル基であり、Ｚ１及びＺ２は、水素原子、又は置換基を有してもよい炭素数１～５のアルキル基である、請求項３～９のいずれか１項に記載の液晶配向剤。 In the formula (2), R 3 is a hydrogen atom or a methyl group, and Z 1 and Z 2 are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent. Item 10. The liquid crystal aligning agent according to any one of Items 3 to 9 . 前記式（１）で表される構造が下記構造である、請求項１～１０のいずれか１項に記載の液晶配向剤。
Figure 2020095900000011
 （式中、Ａ、Ｒ１及びＲ２は、前記と同じ定義である。） The liquid crystal aligning agent according to any one of claims 1 to 10 , wherein the structure represented by formula (1) is the following structure.
Figure 2020095900000011
 (In the formula, A, R 1 and R 2 have the same definitions as above.) 前記ポリイミド前駆体が、下記式（３）の構造単位をさらに含有する、請求項１～１１のいずれか１項に記載の液晶配向剤。
Figure 2020095900000012
 （式中、Ｒ３、Ｚ１及びＺ２の定義は、上記式（２）におけるのと同じである。Ｘ２は、４価の有機基であり、Ｙ２は、２価の有機基である。） The liquid crystal aligning agent according to any one of claims 1 to 11 , wherein the polyimide precursor further contains a structural unit of the following formula (3).
Figure 2020095900000012
 (wherein the definitions of R 3 , Z 1 and Z 2 are the same as in formula (2) above; X 2 is a tetravalent organic group; Y 2 is a divalent organic group; be.) 前記重合体の濃度は、液晶配向剤の全量に対して、１質量％以上１０質量％以下である、請求項１～１２のいずれか１項に記載の液晶配向剤。 The liquid crystal aligning agent according to any one of claims 1 to 12 , wherein the concentration of the polymer is 1% by mass or more and 10% by mass or less with respect to the total amount of the liquid crystal aligning agent. 請求項１～１３のいずれか１項に記載の液晶配向剤を塗布、焼成して得られた膜に、偏光された紫外線を照射して得られる液晶配向膜。 A liquid crystal aligning film obtained by irradiating a film obtained by coating and baking the liquid crystal aligning agent according to any one of claims 1 to 13 with polarized ultraviolet rays. 請求項１４に記載の液晶配向膜を具備する液晶表示素子。 A liquid crystal display device comprising the liquid crystal alignment film according to claim 14 . 下記式で表されるジアミン。
Figure 2020095900000013
 （式中、Ｒ１及びＲ２は、それぞれ独立して、単結合、－Ｏ－、－Ｓ－、－ＮＲ１２－、エステル結合、アミド結合、チオエステル結合、ウレア結合、カーボネート結合、又はカルバメート結合であり、Ｒ１２は、水素原子又はメチル基であり、Ａは炭素数１又は２のアルキレン基である。） A diamine represented by the following formula.
Figure 2020095900000013
 (wherein R 1 and R 2 are each independently a single bond, —O—, —S—, —NR 12 —, an ester bond, an amide bond, a thioester bond, a urea bond, a carbonate bond, or a carbamate bond , R 12 is a hydrogen atom or a methyl group, and A is an alkylene group having 1 or 2 carbon atoms.)
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