TWI673346B - 化合物、包含該化合物的液晶介質及其應用 - Google Patents
化合物、包含該化合物的液晶介質及其應用 Download PDFInfo
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Abstract
本發明揭露了一種化合物,其結構式如下式I所示:
Description
本發明有關液晶化合物領域。更具體地,有關一種化合物、包含該化合物的液晶介質及其應用。
自1888年奧地利科學家萊尼茨爾第一次合成出來了液晶以來,液晶產業真正的發展是近30多年的事,由於液晶顯示材料具有明顯的優點,如驅動電壓低、功耗微小、可靠性高、顯示訊息量大、彩色顯示、無閃爍、可以實現平板顯示等,液晶單體和液晶顯示都經歷了巨大的的發展,液晶單體目前已合成了1萬多種液晶材料,其中常用的液晶顯示材料有上千種,按液晶分子的中心橋鍵和環的特徵進行分類,主要有聯苯液晶、苯基環己烷液晶、酯類液晶、炔類、二氟甲氧橋類、乙烷類及雜環類等。液晶顯示也從30年前的黑白小螢幕的TN、STN發展到現在彩色大螢幕的TN-TFT、VA-TFT、IPS-TFT、PDLC等。
新型液晶顯示方式主要有光學補償彎曲模式(OCB)、共面轉變液晶顯示(IPS)、垂直取向模式(VA)、軸對稱微結構液晶顯示(ASM)、多疇扭曲液晶顯示等。
各種顯示方式液晶盒的設計不同、驅動方式不同,液晶分子指向矢和玻璃基板方向不同,光學補償彎曲模式(OCB)、共面轉變液晶顯示(IPS)液晶分子指向矢和玻璃基板方向是平行的,而垂直取向模式(VA)、軸對稱微結構液晶顯示(ASM)在無電場狀態下液晶分子指向矢和玻璃基板方向垂直。
平行排列方式的IPS,液晶的介電各向異性(△ε)既可以是正的,也可以是負的。
垂直取向模式(VA)所有液晶分子在零場時和玻璃基板方向垂直,與垂直入射光線平行。當偏振片正交時,會顯示良好的暗態,所以該類裝置有良好的對比度,用到液晶的介電各向異性(△ε)必須是負的。液晶的光學各向異性(△n)、液晶盒的厚度(d)、入射光的波長(λ)幾乎影響不到對比度。垂直取向模式(VA)的回應時間比扭曲型裝置要短得多,約為一半左右。在外加電壓影響下,VA裝置主要產生的是液晶分子的彎曲形變, ECB產生的是液晶分子的展曲形變,而扭曲顯示產生的是液晶分子的扭曲形變,其響應時間也分別與彎曲、展曲、扭曲彈性常數成反比,由於大部分的液晶在通常的情況下液晶的彎曲彈性常數大於展曲彈性常數,展曲彈性常數又大於扭曲彈性常數,這也是VA裝置回應時間較快的原因。
對於現有的一些結構類似,其中,R1
和R2
分别獨立的選自鏈烷基、鏈烷氧基等的化合物,由于側向二氟及分子内存在剛性結構硫芴限制二苯環之間的偏轉,使得這類化合物具有較高的介電各向異性的絕對值,以及很高的双折射。但也因为剛性硫芴環的存在,此類烷基取代的液晶化合物互溶性較差,低温下易析出。
因此,為了能使顯示裝置的性能更加接近理想化,需要提供新的液晶化合物,使其能更好的應用於顯示裝置。
為解決以上技術問題,本發明的第一個目的在於提供一種化合物。
本發明的第二個目的在於提供一種液晶介質。
本發明的第三個目的在於提供液晶介質在製備液晶混合物、液晶顯示裝置材料或電光學顯示裝置材料中的應用。
為達到上述第一個目的,本發明採用下述技術方案:
一種化合物,化合物的結構式如下式I所示:I; 其中: R表示環丙基、環戊基和2-四氫呋喃基中的一種; Z表示單鍵、-CH2
-、-O-、-CH2
CH2
-、-CH2
O-、-CF2
O-和-COO-中的一種; X表示H、F、碳原子數為1-7的烷基和碳原子數為1-7的烷氧基中的一種,其中,碳原子數為1-7的烷基和碳原子數為1-7的烷氧基中,一個或多個H原子能被F代替。
本發明中,2-四氫呋喃基的結構式為:,其中,與氧相鄰的C上連接的“—”表示單鍵。
較佳地,上述結構式為式I的化合物的結構式具體如下式I1至式I17所示的其中一種:I1;I2;I3;I4;I5;I6;I7;I8;I9;I10;I11;I12;I13;I14;I15;I16;及I17; 其中: R表示環丙基、環戊基和2-四氫呋喃基中的一種; R1
表示碳原子數為1-7的烷基或碳原子數為1-7的烷氧基,其中,一個或多個H原子能被F代替。
較佳地,上述結構式為式I的化合物的結構式具體如下式I1-1至式I17-1所示的其中一種:I1-1;I2-1;I3-1;I3-2;I4-1;I5-1;I6-1;I6-2;I7-1;I8-1;I9-1;I9-2;I10-1;I11-1;I12-1;I12-2;I12-3;I12-4;I13-1;I14-1;I15-1;I15-2;I16-1;及I17-1。
較佳地,本發明中,上述結構式為式I的化合物可包括但不限於採用如下合成路徑合成:
根據上述合成路徑,式II和式III是合成目標化合物也即式I的化合物的關鍵中間體。式II式III
合成式I所示化合物的關鍵中間體式II和式III可通過商業途徑購買而得,也可參考Org. Biomol. Chem.
, 2003,1, 1609-1624和EP2399896中的相似化合物的合成方法製備獲得。此類方法原理、操作過程、常規後處理、過矽膠柱、重結晶提純等手段是本領域合成人員所熟知的,完全可以實現合成過程,得到目標產物。
上述所有方法的所有步驟的反應均在溶劑中進行;
上述溶劑均選自四氫呋喃、N,N-二甲基甲醯胺、乙醇、甲醇、二氯甲烷、丙酮、甲苯和去離子水中的至少一種。
為達到上述第二個目的,本發明提供一種液晶介質,液晶介質包含一種或多種上述結構式為式I的化合物。
較佳地,上述液晶介質還包含一種或多種結構式為式IV的化合物,作為第二組分:IV; 其中: R2
、R3
各自獨立地表示下列①-③所示基團中的任一基團: ①.碳原子數為1-7的直鏈烷基或碳原子數為1-7的直鏈烷氧基; ②.所述①所示任一基團中的一個或多個-CH2
-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基團;及 ③.所述①所示任一基團中的一個或多個H原子被F、Cl、-CH=CH2
或-CH=CH-CH3
代替所形成的基團;、、、各自獨立地表示如下基團中的任一基團:、、、、、、、、、、、、,並且,、、和中至少有一個選自、和中的一種; m、n、o各自獨立地表示0或1;及 Z1
、Z2
、Z3
各自獨立地表示單鍵、-C2
H4
-、-CH=CH-、、-COO-、-OOC-、-CH2
O-、-OCH2
-、-CF2
O-和-OCF2
-中的一種,其中,任意的H原子能被F代替。
較佳地,上述液晶介質還包含一種或多種結構式為式V的化合物:V; 其中: R4
、R5
各自獨立地表示碳原子數為1-10的烷基或碳原子數為2-10的鏈烯基,其中,任意的-CH2
-能被-CH2
O-、-OCH2
-、-C=C-代替,任意的H原子能被F代替;、、、各自獨立地的表示如下基團的任一基團:、、、、、、、、、、、及; p、q、r各自獨立地表示0或1; Z4
、Z5
、Z6
各自獨立地表示單鍵、-C2
H4
-、-CH=CH-、、-COO-、-OOC-、-CH2
O-、-OCH2
-、-CF2
O-或-OCF2
-,其中,任意的H原子能被F代替。
較佳地,上述液晶介質中,結構式為式I的化合物的質量百分含量為1-24%、結構式為式IV的化合物的質量百分含量為35-58%、結構式為式V的化合物的質量百分含量為30-46%。
較佳地,上述結構式為式IV的化合物的結構式具體如下式IV1至式IV15所示的其中一種:IV1;IV2;IV3;IV4;IV5; ;及
其中:R2、R3各自獨立地表示下列-所示基團中的任一基團:.碳原子數為1-7的直鏈烷基或碳原子數為1-7的直鏈烷氧基;.上述所示任一基團中的一個或多個-CH2-被-O-、-COO-、-OOC-
或-CH=CH-代替所形成的基團;及.上述所示任一基團中的一個或多個H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基團;、各自獨立地表示下列基團中的任一基團:
較佳地,上述結構式為式V的化合物的結構式具體如下式V1至式V16所示的其中一種:
V11;V12;V13;V14;V15;及V16; 其中: R4
、R5
各自獨立地表示碳原子數為1-10的烷基或碳原子數為2-10的鏈烯基,其中,任意的-CH2
-能被-CH2
O-、-OCH2
-或-C=C-代替,任意的H原子能被F代替,(F)各自獨立地表示F或H。
上述液晶介質在製備液晶混合物、液晶顯示裝置材料或電光學顯示裝置材料中的應用也在本發明的保護範圍中。
本發明的有益效果如下:
由於分子內剛性結構和側向二氟的存在,硫芴類液晶表現出較大的負性介電常數,但剛性結構的存在也使此類化合物溶解性較差,限制其應用。令人驚奇的是,當在硫芴類液晶分子內引入環丙基、環戊基和2-四氫呋喃基中的一種作為鏈端基時,所得液晶化合物與傳統含柔性烷基鏈的此類液晶化合物表現出更好的互溶性,故利用本發明提供的式I所示化合物可改善液晶化合物的互溶性,改善混晶低溫穩定性,拓展液晶混合物的應用範圍,具有重要的應用價值。
下面結合所附圖式對本發明的具體實施方式作進一步詳細的說明
為了更清楚地說明本發明,下面結合較佳實施例和所附圖式對本發明做進一步的說明。圖式中相似的部件以相同的圖式符號進行表示。本領域技術人員應當理解,下面所具體描述的內容是說明性的而非限制性的,不應以此限制本發明的保護範圍。
本發明中,製備方法如無特殊說明則均為常規方法。所用的原料如無特別說明均可從公開的商業途徑獲得,所述百分比如無特殊說明,均為質量百分比。
本發明中,各符號的具體意義及測試條件如下: GC表示氣相色譜純度,MP表示熔點,CP表示清亮點,MS表示質譜,△ε表示介電各向異性,△n表示光學各向異性。 測定GC、MP、CP 、MS、△ε和△n的方法均為常規方法。
實施例
1
結構式為式I1-1的化合物:I1-1。 其製備路線如下:
步驟1:1L三口瓶中加入36.3g(0.14mol)2-氟-6-溴-3-環戊基苯酚,22.6g(0.14mol)2,3-二氟苯硼酸,43g(0.31mol)碳酸鉀,300ml甲苯和100ml純水攪拌至全溶,氮氣保護下加入0.05g Pd-132,加熱回流反應6h;停止反應,加400ml純水攪拌分液,水層用200ml×2甲苯萃取,合併有機層,用400ml×2飽和食鹽水洗滌,減壓旋乾溶劑,所得液體加80g石油醚攪拌均勻,-20℃重結晶,得白色固體(1-a)33g,GC:98.5%,收率80.6%。
步驟2:1L三口瓶中加入33g(0.11mol)(1-a),21.5g(0.17mol)二甲氨基硫代甲醯氯,22.2g(0.22mol)三乙胺和300ml二氯甲烷室溫攪拌反應6h;停止反應,加400ml純水攪拌分液,水層用200ml×2二氯甲烷萃取,合併有機層,用400ml×2飽和碳酸氫鈉水洗滌,無水硫酸鈉乾燥後減壓旋乾溶劑,所得液體加100g石油醚攪拌均勻,-20℃重結晶,得白色固體(1-b)35g,GC:98.0%,收率83%。
步驟3:1L三口瓶中加入35g(0.092mol)(1-b),300ml甲苯攪拌至全溶,氮氣保護下加入0.94g Pd(PtBu3
)2
,加熱至100℃反應4h;停止反應,加400ml純水攪拌分液,水層用200ml×2甲苯萃取,合併有機層,用400ml×2飽和食鹽水洗滌,減壓旋乾溶劑,所得液體加100g石油醚攪拌均勻,-20℃重結晶,得白色固體(1-c)30g,GC:99.1%,收率86%。
步驟4:在500ml三口瓶中加入30g(0.08mol)(1-c),氮氣保護下加入200ml二甲基亞碸(DMSO),攪拌均勻,加入8.8g(0.22mol)60%氫化鈉礦物油,加熱至100℃攪拌4小時;停止反應,冷卻至室溫,將反應液倒入300g冰水中攪拌,析出大量固體,濾布吸濾得固體,晾乾,加200ml石油醚加熱全溶後過30g熱矽膠柱,用200ml熱石油醚沖柱,旋乾溶液,1倍甲苯和1倍石油醚加熱全溶,0℃重結晶兩次,得白色固體(I1-1)15g,GC:99.92%,收率65%。
實施例
2
結構式為式I6-2的化合物:I6-2。 其製備路線如下:
步驟1: 以2-氟-6-溴-3-環戊基苯酚和2,3-二氟-4-三氟甲氧基苯硼酸為原料,參考實施例1中步驟1,合成下述式2-a的化合物:(2-a);
步驟2: 以化合物2-a為原料,參考實施例1中步驟2合成的方法合成式2-b化合物:(2-b);
步驟3: 以化合物2-b為原料,參考實施例1中步驟3合成式2-c化合物:(2-c);
步驟4: 以化合物2-c為原料,參考實施例1中步驟4合成目標化合物結構式為式I6-2的化合物:。
實施例
3
結構式為式I12-1的化合物:。 其製備路線如下:
步驟1: 以2-氟-6-溴-3-環丙甲氧基苯酚和2,3-二氟-4-乙氧基苯硼酸為原料,參考實施例1中步驟1,合成下述式3-a的化合物:(3-a);
步驟2: 以化合物3-a為原料,參考實施例1中步驟2合成的方法合成式3-b化合物:(3-b);
步驟3: 以化合物3-b為原料,參考實施例1中步驟3合成3-c化合物:(3-c);
步驟4: 以化合物3-c為原料,參考實施例1中步驟4合成目標化合物結構式為式I12-1的化合物:。
實施例
4
結構式為式I12-2的化合物:。 其製備路線如下:
步驟1: 以2-氟-6-溴-3-環戊甲氧基苯酚和2,3-二氟-4-丁氧基苯硼酸為原料,參考實施例1中步驟1,合成下述式4-a的化合物:(4-a);
步驟2: 以化合物4-a為原料,參考實施例1中步驟2合成的方法合成式4-b化合物:(4-b);
步驟3: 以化合物4-b為原料,參考實施例1中步驟3合成4-c化合物:(4-c);
步驟4: 以化合物4-c為原料,參考實施例1中步驟4合成目標化合物結構式為式I12-2的化合物:。 得到的式I12-2的化合物的質譜圖如第1圖所示。
實施例
5
結構式為式I15-2的化合物:。 其製備路線如下:
步驟1: 以2-氟-6-溴-3-(2-四氫呋喃)乙基苯酚和2,3-二氟-4-丁氧基苯硼酸為原料,參考實施例1中步驟1,合成下述式5-a的化合物:(5-a);
步驟2: 以化合物5-a為原料,參考實施例1中步驟2合成的方法合成式5-b化合物:(5-b);
步驟3: 以化合物5-b為原料,參考實施例1中步驟3合成5-c化合物:(5-c);
步驟4: 以化合物5-c為原料,參考實施例1中步驟4合成目標化合物結構式為式I15-2的化合物:。
混合物實施例
實施例
6-13
:
實施例6-13列出了不同液晶介質的製備方法,其中,各實施例具體化合物的單體結構、用量(重量百分含量)、所得的液晶介質的性能參數測試結果分別如下表1-8所示。
各實施例中所涉及的溫度單位為℃,其他符號的具體意義及測試條件如下: S-N表示液晶的晶態到向列相的熔點(℃); c.p.表示液晶的清亮點(℃),測試儀器:Mettler-Toledo-FP System顯微熱分析儀; γ1
為旋轉粘度(mPa·s),測試條件為:25℃、INSTEC:ALCT-IR1、18微米垂直盒; K11
為扭曲彈性常數,K33
為展曲彈性常數,測試條件為:25℃、INSTEC:ALCT-IR1、18微米垂直盒; △ε表示介電各向異性,△ε=ε∥
-ε⊥
,其中,ε∥
為平行于分子軸的介電常數,ε⊥
為垂直于分子軸的介電常數,測試條件:25℃、INSTEC:ALCT-IR1、18微米垂直盒; Δn表示光學各向異性,△n=no
-ne
,其中,no
為尋常光的折射率,ne
為非尋常光的折射率,測試條件:589nm、25±0.2℃。
本發明中,分別按比例稱取通式I、IV和V的化合物,製備得到液晶介質,其中液晶介質的製備所用的設備和儀器為: (1)電子精密天平(精確度0.1mg); (2)不銹鋼燒杯:用於稱量化合物原料; (3)勺子:用於加入原料; (4)磁力轉子:用於攪拌; (5)控溫電磁攪拌器。
液晶介質的製備方法包括以下步驟: (1)將所用原料按順序擺放整齊; (2)把不銹鋼燒杯放置在天平上,用小勺將式I的化合物盛入不銹鋼燒杯中; (3)依次按所需重量添加其他化合物原料; (4)把加好料的不銹鋼燒杯放置在磁力攪拌儀器上加熱融化; (5)待不銹鋼燒杯中混合物大部份融化後,往不銹鋼燒杯中加入一顆磁力轉子,將液晶混合物攪拌均勻,冷卻到室溫後即得液晶介質。 將所得的液晶介質填充於液晶顯示器兩基板間進行性能測試。
表1 實施例6的液晶介質的組分配比及其性能參數
表2 實施例7的液晶介質的組分配比及其性能參數
表3 實施例8的液晶介質的組分配比及其性能參數
表4 實施例9的液晶介質的組分配比及其性能參數
表5 實施例10的液晶介質的組分配比及其性能參數
表6 實施例11的液晶介質的組分配比及其性能參數
表7 實施例12的液晶介質的組分配比及其性能參數
表8 實施例13的液晶介質的組分配比及其性能參數
對比例 1
配方如下表9所示,其組分中不包含結構式為式I的化合物,而包含結構式為式VI的化合物。
對比例 2
配方如下表10所示,其組分中不包含結構式為式I的化合物,而包含結構式為式VII的化合物。
表9 對比例1的液晶介質的組分配比及其性能參數
表10 對比例2的液晶介質的組分配比及其性能參數
由實施例6-13所示的液晶組合物的性能參數可知,本發明的液晶組合物具有很好的互溶性和極大的負性介電常數,而實施例10和對比例1、對比例2對比可知,以環丙基、環戊基和2-四氫呋喃基為端基的硫芴類液晶化合物與傳統以柔軟的烷基鏈為端基的硫芴類液晶相比時表現出很好的互溶性,低溫穩定性也相應提高,故利用本發明提供的式I所示化合物可改善液晶化合物的互溶性,拓展液晶混合物的應用範圍,具有重要的應用價值。
本發明雖然僅僅列舉了上述8個實施例及對比例的具體化合物及其配比用量(重量百分含量),並進行了性能測試,但是本發明的液晶組合物可以在上述實施例的基礎上,利用本發明所涉及的式I、IV、V所代表的液晶化合物、以及式I、IV、V的較佳液晶化合物進行進一步拓展和修改,通過對其配比用量進行適當調整,均能達到本發明的目的。
顯然,本發明的上述實施例僅僅是為清楚地說明本發明所作的舉例,而並非是對本發明的實施方式的限定,對於所屬領域的普通技術人員來說,在上述說明的基礎上還可以做出其它不同形式的變化或變動,這裡無法對所有的實施方式予以窮舉,凡是屬於本發明的技術方案所引伸出的顯而易見的變化或變動仍處於本發明的保護範圍之列。
無
第1圖示出實施例4式I12-2的化合物的質譜圖。
Claims (10)
- 一種液晶介質,其特徵在於,包含一種或多種如請求項1-3中任一項所述的化合物。
- 如請求項4所述的液晶介質,其中該液晶介質還包含一種或多種結構式為式IV的化合物: IV; 其中: R2、R3各自獨立地表示下列①-③所示基團中的任一基團: ①.碳原子數為1-7的直鏈烷基或碳原子數為1-7的直鏈烷氧基; ②.由①所示任一基團中的一個或多個-CH2-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基團;及 ③.由①所示任一基團中的一個或多個H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基團;、、、各自獨立地表示如下基團中的任一基團:、、、、、、、、、、、及,並且,該、、和中至少有一個選自、和中的一種; m、n、o各自獨立地表示0或1;及 Z1、Z2、Z3各自獨立地表示單鍵、-C2H4-、-CH=CH-、、-COO-、-OOC-、-CH2O-、-OCH2-、-CF2O-和-OCF2-中的一種,其中,任意的H原子能被F代替。
- 如請求項6所述的液晶介質,其中該液晶介質中,結構式為該式I的化合物的質量百分含量為1-24%、結構式為該式IV的化合物的質量百分含量為35-58%、結構式為該式V的化合物的質量百分含量為30-46%。
- 如請求項5-7中任一項所述的液晶介質,其中該結構式為該式IV的化合物的結構式如下式IV1至式IV15所示的其中一種:IV1;IV2;IV3;IV4;IV5;IV6;IV7;IV8;IV9;IV10;IV11;IV12;IV13;IV14;及IV15; 其中: R2、R3各自獨立地表示下列①-③所示基團中的任一基團: ①.碳原子數為1-7的直鏈烷基或碳原子數為1-7的直鏈烷氧基;.由所示任一基團中的一個或多個-CH2-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基團;及.由所示任一基團中的一個或多個H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基團;及、各自獨立地表示下列基團中的任一基團:
- 一種請求項4-9中任一項所述的液晶介質,在製備液晶混合物、液晶顯示裝置材料或電光學顯示裝置材料中的應用。
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