JP2020500981A - フラットな光学的分散を有する重合性lc媒体およびポリマーフィルム - Google Patents
フラットな光学的分散を有する重合性lc媒体およびポリマーフィルム Download PDFInfo
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- JP2020500981A JP2020500981A JP2019529484A JP2019529484A JP2020500981A JP 2020500981 A JP2020500981 A JP 2020500981A JP 2019529484 A JP2019529484 A JP 2019529484A JP 2019529484 A JP2019529484 A JP 2019529484A JP 2020500981 A JP2020500981 A JP 2020500981A
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003505 terpenes Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- 150000003536 tetrazoles Chemical class 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
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- 125000006168 tricyclic group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明は、フラットな光学的分散を有する重合性LC媒体、かかる材料から得られたフラットな光学的分散を有するポリマーフィルム、ならびに光学的、電気光学的、電子的、半導体または発光要素またはデバイスにおける重合性LC媒体およびポリマーフィルムの使用に関する。
重合性液晶材料は、異方性ポリマーフィルムの製造に関して従来技術において公知である。これらのフィルムは、通常、重合性液晶混合物の薄層を基板上に塗布し、混合物を均一な配向に整列させ、最後に重合性液晶材料を重合することによって液晶分子の配向を固定することによって製造される。これにより、重合フィルム中の液晶分子の配向は、平面であり得る、すなわち、液晶分子は、層に対して実質的に平行に、ホメオトロピック(層に対して直交または垂直)にまたは傾斜して配向されている。対応する光学フィルムは、例えば、欧州特許第0940707号明細書(EP 0 940 707 B1)、欧州特許第0888565号明細書(EP 0 888 565 B1)および英国特許第2329393号明細書(GB 2 329 393 B1)に記載されている。
i)例えば、欧州特許第0940707号明細書(EP 0 940 707 B1)に記載されているような「通常の」または「正の」光学的分散
ii)例えば、国際公開第2016/020035号(WO 2016/020035 A1)に記載されているような「逆の」または「負の」の光学的分散、および
iii)例えば、国際公開第2009/058396号(WO 2009/058396 A1)に記載されているような「フラットな」光学的分散。
− 基材への良好な接着を示し、
− 可視光に対して非常に透明であり、
− 経時的に黄色の着色(黄変)が減少し、
− 膜厚を薄くするために高い複屈折を示し、
− 良好な高温安定性または耐久性を示し、さらに、
− 均一に配向されたポリマーフィルムは、相溶性のある、一般的に知られている大量生産用の方法により製造されるべきである。
本発明は、20重量%までの1種以上の式A
Pは、互いに独立して、重合性基であり、好ましくは以下のPについて示される意味の1つを有し、より好ましくは、アクリル、メタクリル、オキセタン、3−エチルオキセタン、エポキシ、ビニルオキシまたはスチレン基であり、
Spは、スペーサー基または単結合であり、好ましくは以下のSpについて示される意味の1つを有し、
Laは、同一または異なって複数存在する場合、F、Cl、CN、SCN、SF5、または直鎖状または分枝鎖状の、任意にモノフッ素化またはポリフッ素化されたアルキル、アルコキシ、アルケニル、アルキニル、アルキルカルボニル、アルコキシカルボニル、または1〜12個の炭素原子を有するアルキルカルボニルオキシもしくはアルキルカルボニルオキシ(ここで、アルキルおよびアルコキシとは異なる基は、少なくとも2個の炭素原子を含み、分枝鎖基は、少なくとも3個の炭素原子を含む)であるか、または任意にハロゲン化されたアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、1〜5個の炭素原子を有するアルキルカルボニルオキシまたはアルコキシカルボニルオキシであり、
rは、0、1、2、3または4である]
で示される化合物と、
20重量%までの1種以上の式I
U1およびU2は、互いに独立して、それらの鏡像を含む
Q1およびQ2は、互いに独立してCHまたはSiHであり、
Q3は、CまたはSiであり、
Bは、それぞれ互いに独立して、−C≡C−、−CY1=CY2−または任意に置換された芳香族もしくはヘテロ芳香族基であり、
Y1,2は、互いに独立して、H、F、Cl、CNまたはR0であり、
qは、1〜10の整数、好ましくは1、2、3、4、5、6または7であり、
A1〜A4は、それぞれ互いに独立して、1個以上の基R5により任意に置換される、非芳香族、芳香族またはヘテロ芳香族炭素環式または複素環式基から選択され、ここで、−(A1−Z1)m−U1−(Z2−A2)n−および−(A3−Z3)o−U2−(Z4−A4)p−は、それぞれ、非芳香族基よりも多くの芳香族基を含まず、好ましくは、1個を上回る芳香族基を含まず、
Z1〜Z4は、互いに独立して、それぞれ、−O−、−S−、−CO−、−COO−、−OCO−、−O−COO−、−CO−NR0−、−NR0−CO−、−NR0−CO−NR0−、−OCH2−、−CH2O−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH2CH2−、−(CH2)3−、−(CH2)4−、−CF2CH2−、−CH2CF2−、−CF2CF2−、−CH=CH−、−CY1=CY2−、−CH=N−、−N=CH−、−N=N−、−CH=CR0−、−C≡C−、−CH=CH−COO−、−OCO−CH=CH−、CR0R00または単結合であり、
R0およびR00は、互いに独立して、Hまたは1〜12個の炭素原子を有するアルキルであり、
mおよびnは、互いに独立して0、1、2、3または4であり、
oおよびpは、互いに独立して0、1、2、3または4であり、
R1〜R5は、互いに独立して、H、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X0、−C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、P−Sp−、任意に置換されたシリル、または任意に置換され、かつ任意に1個以上のヘテロ原子を含む1〜40個の炭素原子を有するカルビルもしくはヒドロカルビルから選択される同一または異なる基であるか、あるいはPもしくはP−Sp−を表すか、またはPもしくはP−Sp−により置換され、ここで、化合物は、PもしくはP−Sp−を表すか、またはPもしくはP−Sp−によって置換されている少なくとも1個の基R1〜5を含み、
Pは、重合性基であり、
Spは、スペーサー基または単結合である]
で示される化合物とを含む。
本明細書中で使用される場合、「ポリマー」という用語は、1つ以上の異なる種類の繰り返し単位(分子の最小構成単位)の骨格を包含し、よく知られている「オリゴマー」、「コポリマー」、「ホモポリマー」等の用語を含む分子を意味すると理解されることになる。さらに、ポリマーという用語は、ポリマー自体に加えて、開始剤、触媒、およびかかるポリマーの合成に付随する他の要素からの残留物を含むことが理解されることになり、ここで、かかる残留物は、共有結合的にそれに組み込まれていないと理解されている。さらに、かかる残留物および他の要素は、通常、重合後の精製プロセスで除去されるが、典型的にはポリマーと混合または混入され、それらは概して容器間または溶媒もしくは分散媒間で移動した際にポリマーと共に残る。
Ee=dθ/dA。
He=Ee・t。
ここで、Lは、それぞれ同一または異なって、上記および下記に示される意味の1つを有し、かつ好ましくは、F、Cl、CN、NO2、CH3、C2H5、C(CH3)3、CH(CH3)2、CH2CH(CH3)C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5またはP−Sp−、極めて好ましくはF、Cl、CN、CH3、C2H5、OCH3、COCH3、OCF3またはP−Sp−、最も好ましくは、F、Cl、CH3、OCH3、COCH3またはOCF3である。
ここで、
W1は、H、F、Cl、CN、CF3、1〜5個の炭素原子を有するフェニルまたはアルキル、特にH、F、ClまたはCH3を表し、
W2は、Hまたは1〜5個の炭素原子を有するアルキル、特にH、メチル、エチルまたはn−プロピルを表し、
W3およびW4は、それぞれ、互いに独立して、H、Clまたは1〜5個の炭素原子を有するアルキルを表し、Pheは、1,4−フェニレンを表し、これは、上記で定義したように1つ以上の基Lにより任意に置換されているが、P−Spとは異なっており、好ましくは、好ましい置換基Lは、F、Cl、CN、NO2、CH3、C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5、さらにフェニルであり、
k1、k2およびk3は、それぞれ、互いに独立して、0または1を表し、k3は、好ましくは1を表し、かつk4は、1〜10の整数である。
−X−アルキル−CHPx−CH2−CH2Py I*a
−X−アルキル−C(CH2Px)(CH2Py)−CH2Pz I*b
−X−アルキル−CHPxCHPy−CH2Pz I*c
−X−アルキル−C(CH2Px)(CH2Py)−CaaH2aa+1 I*d
−X−アルキル−CHPx−CH2Py I*e
−X−アルキル−CHPxPy I*f
−X−アルキル−CPxPy−CaaH2aa+1 I*g
−X−アルキル−C(CH2Pv)(CH2Pw)−CH2OCH2−C(CH2Px)(CH2Py)CH2Pz I*h
−X−アルキル−CH((CH2)aaPx)((CH2)bbPy) I*i
−X−アルキル−CHPxCHPy−CaaH2aa+1 I*k
から選択される多反応性重合性基が好ましく、
ここで、
アルキルは、1〜12個の炭素原子を有する単結合または直鎖状または分枝鎖状のアルキレンを表し、ここで、1つ以上の非隣接CH2基は、Oおよび/またはS原子が互いに直接結合しないように、それぞれ、互いに独立して、−C(Rx)=C(Rx)−、−C≡C−、−N(Rx)−、−O−、−S−、−CO−、−CO−O−、−O−CO−、−O−CO−O−によって置き換えられていてよく、ここで、さらに、1個以上のH原子は、F、ClまたはCNによって置き換えられていてよく、ここで、Rxは、上記の意味のうちの1つを有し、
aaおよびbbは、それぞれ、互いに独立して、0、1、2、3、4、5または6を表し、
Xは、X’について示した意味のうちの1つを有し、かつ
Pv〜Pzは、それぞれ、互いに独立して、Pについて上記で示した意味のうちの1つを有する。
Sp’は、1〜20個、好ましくは1〜12個の炭素原子を有するアルキレンを表し、これはF、Cl、Br、IまたはCNにより任意に一置換または多置換されて、ここで、さらに、1つ以上の非隣接CH2基は、Oおよび/またはS原子が互いに直接結合しないように、それぞれ、互いに独立して、−O−、−S−、−NH−、−NRxx−、−SiRxxRyy−、−CO−、−COO−、−OCO−、−OCO−O−、−S−CO−、−CO−S−、−NRxx−CO−O−、−O−CO−NRoxx−、−NRxx−CO−NRyy−、−CH=CH−または−C≡C−により置き換えられていてよく、
X’は、−O−、−S−、−CO−、−COO−、−OCO−、−O−COO−、−CO−NRxx−、−NRxx−CO−、−NRxx−CO−NRyy−、−OCH2−、−CH2O−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CF2CH2−、−CH2CF2−、−CF2CF2−、−CH=N−、−N=CH−、−N=N−、−CH=CRxx−、−CYxx=CYxx−、−C≡C−、−CH=CH−COO−、−OCO−CH=CH−または単結合を表し、
RxxおよびRyyは、それぞれ、互いに独立して、Hまたは1〜12個の炭素原子を有するアルキルを表し、かつ
YxxおよびYyyは、それぞれ、互いに独立して、H、F、ClまたはCNを表す。
R(λ)=Δn(λ)・d
に従ってその波長における複屈折Δn(λ)と層厚d(nm)との積として定義される。
Δn=ne−no
ここで、neは、異常屈折率であり、noは、常光屈折率であり、かつ有効平均屈折率nav.は、次式で示される:
nav.=((2no 2+ne 2)/3)1/2
好ましくは、重合性LC媒体は、1種、2種またはそれ以上の式Aの化合物、より好ましくは1種の式Aの化合物を含む。
ここで、Zは、上記で示されるZ1の意味の1つを有し、Rは、P−Sp−とは異なる上記で示されるR1の意味の1つを有し、かつP、Sp、Lおよびrは、上記で定義された通りであり、かつメソゲン基中のベンゼン環は、上記で定義されるように1個以上の基Lにより任意に置換される。
ここで、
P0は、互いに独立して複数存在する場合、上記のPについて示された意味の1つを有する重合性基であり、かつ好ましくはアクリル、メタクリル、オキセタン、3−エチルオキセタン、エポキシ、ビニルオキシまたはスチレン基であり、
Sp0は、上記のSp’について示された意味の1つを有するスペーサー基であり、
X0は、上記のX’について示された意味の1つを有し、
Sp0−X0は、好ましくは−(CH2)p1−、−(CH2)p1−O−、−(CH2)p1−CO−O−および−(CH2)p1−O−CO−O−から選択され、ここで、p1は、1〜12の整数であり、これらの基が存在する場合、O原子を介して隣接する環に結合されており、
A0およびB0は、互いに独立して複数存在する場合、1個、2個、3個または4個の基Lで任意に置換される1,4−フェニレン、またはトランス−1,4−シクロヘキシレンであり、
Z0は、互いに独立して複数存在する場合、−COO−、−OCO−、−CH2CH2−、−C≡C−、−CH=CH−、−CH=CH−COO−、−OCO−CH=CH−または単結合であり、
R0は、アルキル、アルコキシ、チオアルキル、アルキルカルボニル、アルコキシカルボニル、アルキルカルボニルオキシまたは1〜20個の炭素原子、好ましくは1〜15個の炭素原子を有するアルコキシカルボニルオキシであるか、またはY0またはP−Sp0−X0−を表し、
Y0は、F、Cl、CN、NO2、OCH3、OCN、SCN、SF5、1〜4個の炭素原子を有する任意にフッ素化されたアルキルカルボニル、アルコキシカルボニル、アルキルカルボニルオキシまたはアルコキシカルボニルオキシ、または1〜4個の炭素原子を有するモノフッ素化、オリゴフッ素化またはポリフッ素化されたアルキルまたはアルコキシであり、
X00は、−O−、−S−、−CO−、−COO−、−OCO−、−O−COO−、−CO−NR01−、−NR01−CO−、−NR01−CO−NR01−、−OCH2−、−CH2O−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CF2CH2−、−CH2CF2−、−CF2CF2−、−CH=N−、−N=CH−、−N=N−、−CH=CR01−、−CF=CF−、−C≡C−、−CH=CH−COO−、−OCO−CH=CH−または単結合であり、
R01は、Hまたは1〜12個の炭素原子を有するアルキルであり、
R*は、4個以上、好ましくは4〜12個の炭素原子を有するキラルアルキル基またはアルコキシ基、例えば、2−メチルブチル、2−メチルオクチル、2−メチルブトキシまたは2−メチルオクトキシであり、
CHは、コレステリル、エストラジオール、またはテルペノイド基から選択されるキラル基、例えば、メンチルまたはシトロネリルであり、
Lは、同一または異なって複数存在する場合、F、Cl、CN、SCN、SF5、または直鎖状または分枝鎖状の、任意にモノフッ素化またはポリフッ素化されたアルキル、アルコキシ、アルケニル、アルキニル、アルキルカルボニル、アルコキシカルボニル、または1〜12個の炭素原子を有するアルキルカルボニルオキシもしくはアルコキシカルボニルオキシ(ここで、アルキルおよびアルコキシとは異なる基は、少なくとも2個の炭素原子を含み、分枝鎖基は、少なくとも3個の炭素原子を含む)であるか、または任意にハロゲン化されたアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、1〜5個の炭素原子を有するアルキルカルボニルオキシまたはアルコキシカルボニルオキシであり、
rは、0、1、2、3または4であり、
uは、0または1であり、
vおよびvは、互いに独立して0、1または2であり、
ベンゼン環およびナフタレン環は、さらに、1個以上の同一または異なる基Lで置換され得る。
ここで、P0およびR0は、上記で定義された通りであり、R0は、好ましくは1〜6個の炭素原子を有するアルキル、アルコキシまたはアルキルカルボニルオキシであり、Lは、HまたはCH3であり、
xおよびyは、互いに独立して0または1〜12の同一または異なる整数であり、
zは、互いに独立して0または1であり、隣接するxまたはyが0の場合zは0である。
C1〜C4−アルコール、例えばメタノール、エタノール、n−プロパノール、イソプロパノール、ブタノール、イソブタノール、sec−ブタノール、特にC5〜C12−アルコール、n−ペンタノール、n−ヘキサノール、n−ヘプタノール、n−オクタノール、n−ノナノール、n−デカノール、n−ウンデカノールおよびn−ドデカノール、ならびにその異性体、グリコール、例えば1,2−エチレングリコール、1,2−および1,3−プロピレングリコール、1,2−、2,3−および1,4−ブチレングリコール、ジ−およびトリエチレングリコール、およびジ−およびトリプロピレングリコール、エーテル、例えばメチルtert−ブチルエーテル、1,2−エチレングリコールモノ−およびジメチルエーテル、1,2−エチレングリコールモノ−および−ジエチルエーテル、3−メトキシプロパノール、3−イソプロポキシプロパノール、テトラヒドロフランおよびジオキサン、ケトン、例えばアセトン、メチルエチルケトン、メチルイソブチルケトンおよびジアセトンアルコール(4−ヒドロキシ−4−メチル−2−ペンタノン)、C1〜C5−アルキルエステル、例えば酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチルおよび酢酸アミル、脂肪族および芳香族炭化水素、例えばペンタン、ヘキサン、ヘプタン、オクタン、イソオクタン、石油エーテル、トルエン、キシレン、エチルベンゼン、テトラリン、デカリン、ジメチルナフタレン、ホワイトスピリット、Shellsol(登録商標)およびSolvesso(登録商標)鉱油、例えばガソリン、ケロシン、軽油および加熱油、さらには天然油、例えばオリーブ油、大豆油、菜種油、亜麻仁油およびひまわり油。
アルキル化モノフェノール、例えば、2,6−ジ−tert−ブチル−4−メチルフェノール、2−tert−ブチル−4,6−ジメチルフェノール、2,6−ジ−tert−ブチル−4−エチルフェノール、2,6−ジ−tert−ブチル−4−n−ブチルフェノール、2,6−ジ−tert−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−tert−ブチル−4−メトキシメチルフェノール、直鎖状または分枝鎖状の側鎖を有するノニルフェノール、例えば、2,6−ジノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルトリデカ−1’−イル)フェノールおよびこれらの化合物の混合物、アルキルチオメチルフェノール、例えば、2,4−ジオクチルチオメチル−6−tert−ブチルフェノール、2,4−ジオクチルチオメチル−6−メチルフェノール、2,4−ジオクチルチオメチル−6−エチルフェノールおよび2,6−ジドデシルチオメチル−4−ノニルフェノール、
a)1種以上の二反応性または多反応性の重合性メソゲン化合物、
b)1種以上の光開始剤、
c)任意で、1種以上の単反応性の重合性メソゲン化合物、
d)任意で、1種以上の酸化防止添加剤、
e)任意で、1種以上の接着促進剤、
f)任意で、1種以上の界面活性剤、
g)任意で、1種以上の安定剤、
h)任意で、1種以上の単反応性、二反応性または多反応性の重合性非メソゲン化合物、
i)任意で、光重合を開始するために使用される波長で吸収極大を示す1種以上の色素、
j)任意で、1種以上の連鎖移動剤、
k)任意で、1種以上の安定剤、
l)任意で、1種以上の潤滑剤および流動助剤、および
m)任意で、1種以上の希釈剤
を含む。
a)20重量%までの1種以上の、式Aの化合物、好ましくは式A2またはA6の化合物から選択される化合物、より好ましくは式A2の化合物、
b)20重量%までの1種以上の、式Iの化合物、好ましくは式I−25またはI−26の化合物から選択される化合物、
c)1種以上、好ましくは2種以上の、好ましくは10〜95重量%の量の、非常に好ましくは25〜85重量%の量の、好ましくは式MRM−1および/またはMRM−7の化合物から選択される単反応性重合性メソゲン化合物、
d)1種以上の、好ましくは0.1〜10重量%の量の、光開始剤、
e)任意で、1種以上の、好ましくは2種以上の、好ましくは、存在するとしても10〜90重量%の量の、非常に好ましくは15〜75重量%の量の、好ましくは式DRMa−1の化合物から選択される、二反応性メソゲン化合物、
f)任意で、1種以上の、好ましくは非置換および置換安息香酸のエステル、特にIrganox(登録商標)1076から選択され、存在する場合、好ましくは0.01〜2重量%の量の、非常に好ましくは0.05〜1重量%の量の、1種以上の酸化防止添加剤、
g)任意で、好ましくはBYK(登録商標)310、BYK(登録商標)388、FC4430および/またはFluor N 562から選択され、かつ存在する場合、好ましくは0.1〜5重量%の量の、非常に好ましくは0.2〜3重量%の量の、1種以上の潤滑剤および流動助剤、
h)任意で、1種以上の、好ましくは、存在するとしても0.1〜5重量%の量の、非常に好ましくは0.2〜3重量%の量の、好ましくはn−ドデカノールから選択される、希釈剤、
を含む。
− 上記および下記の重合性LC材料の層を基材上に供給すること、
− 重合性LC材料を光重合により重合すること、および
− 任意で、重合したLC材料を基材から除去することおよび/またはこれを別の基材上に供給すること
によりポリマーフィルムを製造する方法に関する。
δ(λ)=(2πΔn・d)λ (7)
によって示され、
ここで、(Δn)はフィルムの複屈折率、(d)はフィルムの厚さ、λは入射ビームの波長である。
Δn=sinθ/sinΨ (8)
によって定義され、
ここで、sinθは、フィルム内の光軸の入射角または傾斜角であり、sinΨは対応する反射角である。
2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキシド PI 1
2−メチル−4’−(メチルチオ)−2−モルホリノプロピオフェノン PI 2
ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキシド PI 3
2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1
PI 4
まず、トルエン/シクロヘキサン溶液(7:3)中の対応するLC媒体の33.3w/w%溶液を調製する。
R450/R550の値とR650/R550のα値との比較から分かるように、本発明によるポリマーフィルムは、改善されたフラットな分散特性を示す。
R450/R550の値とR650/R550のα値との比較から分かるように、本発明によるポリマーフィルムは、改善されたフラットな分散特性を示す。
耐久性試験の結果の比較から分かるように、本発明によるポリマーフィルム(M−3〜M−6)は、すべて、CM−3と比較して耐久性の顕著な改善を示す。
耐久性試験の結果の比較から分かるように、本発明によるポリマーフィルム(M−3、およびM−7〜M−9)は、すべて、CM−3と比較して耐久性の顕著な改善を示す。
第6.1表に示した結果の比較から分かるように、20%より多い量でC−5を含む比較混合物CM−7およびCM−8は、結晶化試験に合格しなかった。一方で、本発明による混合物M−18およびM−19は、結晶化を示さない。
耐久性試験の結果の比較から分かるように、混合物M−20およびM−21から得られた本発明によるポリマーフィルムは、双方とも、CM−10と比較して耐久性の顕著な改善を示し、依然として550nmで複屈折率Δnについて好ましい値を示す。
Claims (15)
- 20%までの1種以上の式A
Pは、互いに独立して、重合性基であり、
Spは、スペーサー基または単結合であり、
Laは、同一または異なって複数存在する場合、F、Cl、CN、SCN、SF5、または直鎖状または分枝鎖状の、任意にモノフッ素化またはポリフッ素化されたアルキル、アルコキシ、アルケニル、アルキニル、アルキルカルボニル、アルコキシカルボニル、または1〜12個の炭素原子を有するアルキルカルボニルオキシもしくはアルコキシカルボニルオキシであるか、または任意にハロゲン化されたアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、1〜5個の炭素原子を有するアルキルカルボニルオキシまたはアルコキシカルボニルオキシであり、
rは、0、1、2、3または4である]
で示される化合物と、
20%までの1種以上の式I
U1およびU2は、互いに独立して、それらの鏡像を含む
Q1およびQ2は、互いに独立してCHまたはSiHであり、
Q3は、CまたはSiであり、
Bは、それぞれ互いに独立して、−C≡C−、−CY1=CY2−または任意に置換された芳香族もしくはヘテロ芳香族基であり、
Y1およびY2は、互いに独立して、H、F、Cl、CNまたはR0であり、
qは、1〜10の整数であり、
A1〜A4は、それぞれ互いに独立して、1個以上の基R5により任意に置換される、非芳香族、芳香族またはヘテロ芳香族炭素環式または複素環式基から選択され、ここで、−(A1−Z1)m−U1−(Z2−A2)n−および−(A3−Z3)o−U2−(Z4−A4)p−は、それぞれ、非芳香族基よりも多くの芳香族基を含まず、
Z1〜Z4は、互いに独立して、それぞれ、−O−、−S−、−CO−、−COO−、−OCO−、−O−COO−、−CO−NR0−、−NR0−CO−、−NR0−CO−NR0−、−OCH2−、−CH2O−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH2CH2−、−(CH2)3−、−(CH2)4−、−CF2CH2−、−CH2CF2−、−CF2CF2−、−CH=CH−、−CY1=CY2−、−CH=N−、−N=CH−、−N=N−、−CH=CR0−、−C≡C−、−CH=CH−COO−、−OCO−CH=CH−、CR0R00または単結合であり、
R0およびR00は、互いに独立して、Hまたは1〜12個の炭素原子を有するアルキルであり、
mおよびnは、互いに独立して0、1、2、3または4であり、
oおよびpは、互いに独立して0、1、2、3または4であり、
R1〜R5は、互いに独立して、H、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X0、−C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、P−Sp−、任意に置換されたシリル、または任意に置換され、かつ任意に1個以上のヘテロ原子を含む1〜40個の炭素原子を有するカルビルもしくはヒドロカルビルから選択される同一または異なる基であるか、あるいはPもしくはP−Sp−を表すか、またはPもしくはP−Sp−により置換され、ここで、化合物は、PもしくはP−Sp−を表すか、またはPもしくはP−Sp−によって置換されている少なくとも1個の基R1〜5を含み、
Pは、重合性基であり、
Spは、スペーサー基または単結合である]
で示される化合物とを含む、重合性LC媒体。 - 架橋基、または式I中の−(B)q−は、−C≡C−、−C≡C−C≡C−、−C≡C−C≡C−C≡C−、−C≡C−C≡C−C≡C−C≡C−、
ここで、
rは、0、1、2、3または4であり、かつ
Lは、P−Sp−、F、Cl、Br、I、−CN、−NO2、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X、−C(=O)OR0、−C(=O)R0、−NR0R00、−OH、−SF5、任意に置換されたシリル、1〜12個の炭素原子を有するアリール、および1〜12個の炭素原子を有する直鎖状または分枝鎖状のアルキル、アルコキシ、アルキルカルボニル、アルコキシカルボニル、アルキルカルボニルオキシまたはアルコキシカルボニルオキシから選択され、ここで、1個以上のH原子は、FまたはClにより任意に置き換えられ、ここで、R0およびR00は、請求項1において規定されており、かつXは、ハロゲンであることを特徴とする、請求項1または2記載の重合性LC媒体。 - 芳香族基および非芳香族基、または式I中のA1〜4が、請求項3において規定されたように1個以上の基Lで任意に置換される、トランス−1,4−シクロヘキシレンおよび1,4−フェニレンから選択されることを特徴とする、請求項1から4までのいずれか1項記載の重合性LC媒体。
- メソゲン基中の芳香族および非芳香族環式基を連結する連結基、または式IにおけるZ1〜4が、−O−、−S−、−CO−、−COO−、−OCO−、−O−COO−、−CO−NR0−、−NR0−CO−、−NR0−CO−NR0−、−OCH2−、−CH2O−、−SCH2−、−CH2S−、−CF2O−、−OCF2−、−CF2S−、−SCF2−、−CH2CH2−、−(CH2)3−、−(CH2)4−、−CF2CH2−、−CH2CF2−、−CF2CF2−、−CH=CH−、−CY1=CY2−、−CH=N−、−N=CH−、−N=N−、−CH=CR0−、−C≡C−、−CH=CH−COO−、−OCO−CH=CH−、CR0R00または単結合から選択され、ここで、R0、R00、Y1およびY2は、請求項1において示された意味を有することを特徴とする、請求項1から5までのいずれか1項記載の重合性LC媒体。
- 式Iの重合性化合物は、下位式I25またはI26から選択され、ここで、Zは、−COO−を表し、rは、それぞれ0であり、Rは、P−Sp−とは異なる、請求項1に示されたR1の意味の1つを有し、かつP、Spは、請求項1に規定された通りであることを特徴とする、請求項1から8までのいずれか1項記載の重合性LC媒体。
- 1種以上の式Iの化合物、請求項1から9までのいずれか1項に規定された1種以上の式Aの化合物、および任意に重合性および/またはメソゲン性または液晶性である1種以上のさらなる化合物を含む、重合性LC媒体。
- 請求項1から10までのいずれか1項に規定された重合性LC媒体を、そのLC相で配向状態で薄膜の形で重合することによって得られるポリマーフィルム。
- 請求項11記載のポリマーフィルムまたは請求項1から10までのいずれか1項記載の重合性LC媒体の、光学的、電子的または電気光学的デバイス、またはそれらの要素における使用。
- Aプレート、Cプレート、負のCプレートまたはOプレートから選択される光学的一軸フィルム、ねじれ光学的位相差板、ねじれ1/4波長箔(QWF)、光学的二軸フィルム、色消し位相差板、色消しQWFまたは半波長箔(HWF)、コレステリック、スメクチック、ネマチックまたはブルー相を有するフィルム、ホメオトロピック、スプレイ、チルト、平面またはブルー相配向を有するフィルムであり、該フィルムは、均一に配向しているか、または異なる配向のパターンを示すことを特徴とする、光学要素。
- LCDの視野角向上用の光学補償フィルム、輝度向上フィルム中の要素、または反射型もしくは半透過型LCD中の色消し要素であることを特徴とする、請求項13記載の光学要素。
- 請求項11記載のポリマーフィルムまたは請求項1から10までのいずれか1項記載の重合性LC媒体を含む、光学的、電子的または電気光学的デバイス、またはそれらの要素。
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JP2017532387A (ja) * | 2014-08-04 | 2017-11-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 負の光分散を有する重合性lc媒体およびポリマーフィルム |
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WO2021193131A1 (ja) * | 2020-03-23 | 2021-09-30 | 住友化学株式会社 | 重合性液晶化合物、重合性液晶組成物、位相差フィルム、楕円偏光板および有機el表示装置 |
WO2022092063A1 (ja) * | 2020-10-30 | 2022-05-05 | Jnc株式会社 | 低誘電率樹脂形成用組成物、低誘電部材、及びそれを用いた電子機器 |
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TWI741086B (zh) | 2021-10-01 |
CN110023456B (zh) | 2023-02-17 |
KR20190088501A (ko) | 2019-07-26 |
EP3548586A1 (en) | 2019-10-09 |
TW201842167A (zh) | 2018-12-01 |
KR102497292B1 (ko) | 2023-02-07 |
EP3548586B1 (en) | 2020-09-23 |
US11248171B2 (en) | 2022-02-15 |
WO2018099883A1 (en) | 2018-06-07 |
CN110023456A (zh) | 2019-07-16 |
US20200024519A1 (en) | 2020-01-23 |
JP7078623B2 (ja) | 2022-05-31 |
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