CN102557929A - 手性双萘基化合物 - Google Patents
手性双萘基化合物 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000000126 substance Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 53
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000002019 doping agent Substances 0.000 abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- -1 binaphthyl compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- KQIKVAKMKWRTIH-UHFFFAOYSA-N cyclohexylbenzene formic acid Chemical compound C(=O)O.C1(CCCCC1)C1=CC=CC=C1 KQIKVAKMKWRTIH-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07C271/06—Esters of carbamic acids
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- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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Abstract
本发明是涉及一种手性双萘基化合物，具下列化学式(I)结构：
Description
技术领域
本发明是有关于一种旋光化合物，且特别是有关于一种应用于液晶的手性双萘基旋光化合物。
背景技术
现今业界广泛应用的液晶显示器种类繁多，依其内含的液晶分子及显像原理的不同可大致分为向列型(Nematic)液晶的显示元件、扭转90度的扭转向列型(Twisted Nematic，TN)液晶显示元件、扭转180度或180度以上的超扭转向列型(Super Twisted Nematic；STN)液晶显示元件、表面稳定胆甾型结构(Surface-Stabilized Cholesteric Texture；SSCT)液晶显示元件、聚合物稳定胆甾型结构(polymer-stabilized cholesteric texture；PSCT)型液晶板或薄膜晶体管(TFT)型液晶显示元件。
液晶显示元件的显示质量乃是其核心价值，而液晶显示元件的显示质量可由数项重要特性来评估，例如：电压保持率(Voltage Holding Ratio；VHR)及残留直流电数值等。若电压保持率较低，那么在帧时间(frame time)中施加至液晶的电压会下降，结果会导致亮度下降，甚至会阻碍正常的灰阶显示。另一方面，如果残留直流电较大，那么有时会产生所谓的”残影”，即施加电压后无论断电与否，都残留应消失的图像。
发明内容
本发明的目的在于提供一种应用于液晶的手性双萘基旋光化合物，其拥有良好溶解性与相当高的螺旋扭转力(Helical Twisting Power；HTP)。此系列旋光性化合物适用于各类显示器的液晶配方，依不同比例与液晶调配后，提供高电压保持率(VHR)，可帮助降低影像残留并提高画面对比。
本发明提供一种手性双萘基化合物(chiral binaphthyl compounds)，具下列化学式(I)结构：
其中，Y为以-(A1-Z)m-A2-表示的重复单元，A1与A2为环状结构，可分别选自于下列族群：
X与Z为相同或不同的连接基(linking group)，可分别选自于下列族群：-O-，-S-，-CO-，-COO-，-OCO-，-O-COO-，-CO-N(R1)-，-N(R1)-CO-，-OCH2-，-CH2O-，-SCH2-，-CH2S-，-CF2O-，-OCF2-，-CF2S-，-SCF2-，-CH2CH2-，-CF2CH2-，-CH2CF2-，-CF2CF2-，-CH＝CH-，-CF＝CH-，-CH＝CF-，-CF＝CF-，-C≡C-，-CH＝CH-COO-，-CH＝CH-或一单键，
a、b与c分别独立为0、1或2，m为0、1、2或3，R为C1～C30的直链或支链烷基、C1～C30的直链或支链烷基且其中的单一或多个-CH2-是被-O-，-S-，-NH-，-N(CH3)-，-CO-，-CO-O-，-O-CO-，-CH＝CH-或-C≡C-所取代、或前述的烷基选择性具有-F，-Cl，-Br，-NCS，-CN，-OCF3的取代者。
根据本发明的实施方式，本发明所述的手性双萘基化合物可具下列化学式(II)结构，
其中R＝C5H11。
根据本发明的实施方式，本发明所述的手性双萘基化合物可具下列化学式(III)结构，
其中R＝C7H15。
本发明的手性双萘基化合物的优点在于：将该手性双萘基旋光化合物添加到常见液晶组成配方中，可使该掺杂的液晶组合物符合产业需求，其电压维持率(VHR)可保持≥90％，特别可帮助提高其画面对比与降低其影像残留；且本发明的手性双萘基旋光化合物具有较高的HTP值，在达到相同波长条件下使添加量减少，进而降低驱动电压，影响液晶程度较小且成本更低。相较于已知的液晶掺杂物，本案的手性双萘基旋光化合物确实更适合作为液晶掺杂物，应用于不同液晶组成配方。
为让本发明的上述特征和优点能更明显易懂，下文特举实施例，作详细说明如下。
具体实施方式
本发明是涉及一种手性双萘基旋光化合物，拥有良好溶解性与相当高的螺旋扭转力(HTP)。此系列旋光性化合物适用于各类显示器的液晶配方，依不同比例作为液晶掺杂物与液晶调配后，使液晶面板具有高电压维持比(VHR)，可帮助降低影像残留并提高画面对比。
由于液晶分子的光学特性可经由掺杂剂(dopant)的掺入而加以改善或修饰。本发明的手性双萘基旋光化合物可作为液晶组合物的掺杂物。
本发明所谓的“液晶”包括各种常见的液晶面板或液晶屏幕所用的液晶，其范围包括向列型液晶或胆甾型液晶等。上述液晶组成材料的更替调整，应为此领域发明者所能理解，也是本发明所欲保护的范围。
本发明的手性双萘基旋光化合物以下列通式(I)代表之：
其中，Y为以-(A1-Z)m-A2-表示的重复单元，A1与A2为环状结构，可分别选自于下列族群：
X与Z为相同或不同的连接基(linking group)，可分别选自于下列族群：-O-，-S-，-CO-，-COO-，-OCO-，-O-COO-，-CO-N(R1)-，-N(R1)-CO-，-OCH2-，-CH2O-，-SCH2-，-CH2S-，-CF2O-，-OCF2-，-CF2S-，-SCF2-，-CH2CH2-，-CF2CH2-，-CH2CF2-，-CF2CF2-，-CH＝CH-，-CF＝CH-，-CH＝CF-，-CF＝CF-，-C≡C-，-CH＝CH-COO-，-CH＝CH-或一单键，
其中a、b与c分别独立为0、1或2，m为0、1、2或3，R为C1～C30的直链或支链烷基、C1～C30的直链或支链烷基且其中的单一或多个-CH2-是被-O-，-S-，-NH-，-N(CH3)-，-CO-，-CO-O-，-O-CO-，-CH＝CH-或-C≡C-所取代、或前述的烷基选择性具有-F，-Cl，-Br，-NCS，-CN，-OCF3的取代者。
本发明的手性双萘基旋光化合物可通过此领域已知的有机合成制程制备，并视不同取代基，而调整使用合成溶剂、反应条件、温度或添加物等，该些详细步骤或实施条件调整并不限于本说明书的实施例，而为此领域者所理解。
实验
合成反应步骤：如下列化学反应式(1)
将8mmol的反式-4-戊基环己基苯甲酸(4-(trans-4-pentylcyclohexyl)benzoicacid)与20ml无水四氢呋喃(dry THF)置于反应瓶中，待其溶解后加热至回流温度。温度到达后，加入12mmol的1，1-羰基二咪唑(1，1′-Carbonyldiimidazole；CDI)，搅拌反应过夜，反应溶液由透明液体变为黄色液体。将反应冷却至室温，减压浓缩将THF去除，得到黄色固体。以二氯甲烷与水萃取、取有机层，加入无水硫酸镁除水后，减压浓缩得中间产物白色酯类产物(a)2.96g(9.2mmol)。
另外将3.2mmol的(S，S)-1，2-二(1-萘基)-1，2-乙二醇((S，S)-1，2-Di(1-napthyl)-1，2-ethanediol)与无水四氢呋喃(20ml)置于反应瓶中，待其溶解后冰浴至0℃，于冰浴中缓慢加入氢化钠(7.6mmol)，持续搅拌反应10分钟。
随后将先前取得的9.2mmol酯类产物(a)加入，反应温度由冰浴缓慢回复至室温并持续搅拌反应1小时。反应结束后以减压浓缩将THF去除得到黄色液体，使用二氯甲烷与水进行萃取，取有机层，加入无水硫酸镁除水后，减压浓缩得黄色粗产物2.2g。
将黄色粗产物以异丙醚与甲醇作重结晶，静置一晚后以抽气过滤得白色片状结晶产物2.01g(2.4mmol)，产率76.3％。
利用上述反应式(1)可得到具有化学式(II)结构的下列化合物--实验产物1，其中a＝1、b＝0、c＝1、m＝1和Z＝单键，R＝C5H11。
实验产物1：R＝C5H11
产率76.3％，Tm 167℃，
1H NMR(400MHz，CDCl3)确认：σ8.32(s，2H)，7.99(d，J＝8.0Hz，4H)，7.71(d，J＝8.0Hz，2H)，7.63(d，J＝8.1Hz，2H)，7.50(s，2H)，7.45(s，2H)，7.39(q，J＝13.5，6.4Hz，4H)，7.22(q，J＝16.6，7.9Hz，6H)，2.49(t，J＝12.0Hz，2H)，1.86(d，J＝9.3Hz，8H)，1.43(q，J＝23.0，11.6Hz，4H)，1.32(t，J＝6.03Hz，8H)，1.28(d，J＝9.4Hz，8H)，1.25(s，2H)，1.07(q，J＝23.1，12.1Hz，4H)，0.90(t，J＝6.7Hz，6H).
以及以类似的方法，使用反式-4-庚基环己基苯甲酸代替反式-4-戊基环己基苯甲酸，利用上述反应式(1)可得到具有化学式(II)结构的实验产物2，其中a＝1、b＝0、c＝1、m＝1和Z＝单键，R＝C7H15。
实验产物2：R＝C7H15
产率74.5％，Tm 153℃，
1H NMR(400MHz，CDCl3)确认：σ8.31(s，2H)，7.98(d，J＝8.2Hz，4H)，7.70(d，J＝8.3Hz，2H)，7.63(d，J＝8.2Hz，2H)，7.50(s，2H)，7.44(s，2H)，7.39(q，J＝12.9，6.1Hz，4H)，7.22(q，J＝16.4，8.0Hz，6H)，2.49(t，J＝12.0Hz，2H)，1.86(d，J＝9.6Hz，8H)，1.38(q，J＝23.1，12.1Hz，4H)，1.28(s，22H)，1.24(s，4H)，1.04(q，J＝23.0，10.8Hz，4H)，0.89(t，J＝6.1Hz，6H)。
在下列实验中，将比较以本发明的手性双萘基旋光化合物掺杂至主动液晶组成配方，而与含常见掺杂物的液晶组成配方来进行比较。
将实验产物1-2添加到常见主动阵列液晶组成配方中，发现该掺杂的液晶组合物的VHR可保持≥90％，且实验产物1-2具有HTP值≥40μm-1，在相同波长条件下添加量较少(参见表1)。相较于已知的液晶掺杂物(例如，S-811、S-1011或R-1011)，本案的手性双萘基旋光化合物可提供更好的功效，适合应用于不同液晶组成配方。
表1
＊未添加掺杂物前液晶组合物的VHR＝100％，反射波长550nm。主动阵列液晶组成物1&2的分子组成、比例不同，但皆为含氟的液晶配方。
已知的液晶掺杂物S-811、S-1011或R-1011的结构式如下：
本发明的手性双萘基旋光化合物添加到常见液晶组成配方中，使该掺杂的液晶组合物提供符合产业需求、良好的电压维持率(VHR)。可使VHR保持≥90％，对于需要考虑VHR的主动阵列液晶显示元件来说，特别可帮助提高其画面对比与降低其影像残留。且本发明的手性双萘基旋光化合物具有较高的HTP值，在达到相同波长条件下使添加量减少，进而降低驱动电压，影响液晶程度较小且成本更低。相较于已知的液晶掺杂物，本案的手性双萘基旋光化合物确实更适合作为液晶掺杂物，应用于不同液晶组成配方。
将本发明所涵盖一系列化合物的范例化合物列于下表2，但表2所示仅为不同a，b，c或m数值的范例，且或仅包括X、Y、Z、A1、A2或R各取代基的部分例子，而X、Y、Z、A1、A2或R所涵盖的范围如上述通式(I)所定义之。本发明所涵盖一系列手性双萘基旋光化合物并不限于表2所示的这些化合物。
表2
实施例中以液晶组成配方来表示本发明所述手性双萘基化合物的可能应用范围与方式，但实际应用的领域或设计并不限于实施例或实验所述的内容，而可转用至其它相关领域、结构或产品，并为此领域发明者所能理解。
虽然本发明已以实施例揭露如上，然其并非用以限定本发明，任何所属技术领域中具有通常知识者，在不脱离本发明的精神和范围内，当可作些许的更动与润饰，故本发明的保护范围当视后附的权利要求书所界定的范围为准。
Claims (8)
1.一种手性双萘基化合物，具下列化学式(I)结构：
其中，Y为以-(A1-Z)m-A2-表示的重复单元，A1与A2为环状结构，可分别选自于下列族群：
X与Z为相同或不同的连接基，可分别选自于下列族群：-O-，-S-，-CO-，-COO-，-OCO-，-O-COO-，-CO-N(R1)-，-N(R1)-CO-，-OCH2-，-CH2O-，-SCH2-，-CH2S-，-CF2O-，-OCF2-，-CF2S-，-SCF2-，-CH2CH2-，-CF2CH2-，-CH2CF2-，-CF2CF2-，-CH＝CH-，-CF＝CH-，-CH＝CF-，-CF＝CF-，-C≡C-，-CH＝CH-COO-，-CH＝CH-或一单键，
a、b与c分别独立为0、1或2，m为0、1、2或3，R为C1～C30的直链或支链烷基、C1～C30的直链或支链烷基且其中的单一或多个-CH2-是被-O-，-S-，-NH-，-N(CH3)-，-CO-，-CO-O-，-O-CO-，-CH＝CH-或-C≡C-所取代、或前述的烷基选择性具有-F，-Cl，-Br，-NCS，-CN，-OCF3的取代者。
2.如权利要求1所述的手性双萘基化合物，其中当a＝0，b＝1，c＝0时，该手性双萘基化合物为
3.如权利要求1所述的手性双萘基化合物，其中当a＝1，b＝0，c＝1时，该手性双萘基化合物为
4.如权利要求1所述的手性双萘基化合物，其中当a＝1，b＝0，c＝2时，该手性双萘基化合物为
5.如权利要求1所述的手性双萘基化合物，其中当a＝1，b＝1，c＝1时，该手性双萘基化合物为
6.如权利要求1所述的手性双萘基化合物，其中当a＝1，b＝1，c＝1，m＝1时，该手性双萘基化合物为
7.如权利要求1所述的手性双萘基化合物，具下列化学式结构：
其中R＝C5H11。
8.如权利要求1所述的手性双萘基化合物，具下列化学式结构：
其中R＝C7H15。
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| EP0326086B1 (en) * | 1988-01-25 | 1992-07-08 | Canon Kabushiki Kaisha | Liquid crystal composition and liquid crystal device using same |
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| CN1032182A (zh) * | 1987-09-18 | 1989-04-05 | 霍夫曼-拉罗奇有限公司 | 铁电液晶单元 |
| EP0326086B1 (en) * | 1988-01-25 | 1992-07-08 | Canon Kabushiki Kaisha | Liquid crystal composition and liquid crystal device using same |
| EP1375627A1 (en) * | 2002-06-25 | 2004-01-02 | Mitsubishi Gas Chemical Company, Inc. | Optically active compound and liquid crystal composition containing the same |
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