TWI755897B - 含有2,3,4-三取代苯的液晶化合物、其組合物及其液晶顯示元件 - Google Patents
含有2,3,4-三取代苯的液晶化合物、其組合物及其液晶顯示元件 Download PDFInfo
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- TWI755897B TWI755897B TW109136208A TW109136208A TWI755897B TW I755897 B TWI755897 B TW I755897B TW 109136208 A TW109136208 A TW 109136208A TW 109136208 A TW109136208 A TW 109136208A TW I755897 B TWI755897 B TW I755897B
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- liquid crystal
- carbon atoms
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- 0 *C(CC1)CCC1C(CC1)CCC1C=C Chemical compound *C(CC1)CCC1C(CC1)CCC1C=C 0.000 description 14
- VDFVNEFVBPFDSB-UHFFFAOYSA-N C1COCOC1 Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 3
- SYPWODYWAUMNMD-UHFFFAOYSA-N CC1COC(C(CC2)CCC2c(ccc(OC(F)(F)F)c2F)c2F)OC1 Chemical compound CC1COC(C(CC2)CCC2c(ccc(OC(F)(F)F)c2F)c2F)OC1 SYPWODYWAUMNMD-UHFFFAOYSA-N 0.000 description 2
- GOYDNIKZWGIXJT-UHFFFAOYSA-N Fc1ccccc1F Chemical compound Fc1ccccc1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- PRENMDQJBWGLKD-UHFFFAOYSA-N CC(CC1)CCC1C(CC1)CC=C1c(ccc(F)c1F)c1F Chemical compound CC(CC1)CCC1C(CC1)CC=C1c(ccc(F)c1F)c1F PRENMDQJBWGLKD-UHFFFAOYSA-N 0.000 description 1
- ROXOIDFLXLKFIH-UHFFFAOYSA-N CC(CC1)CCC1C(CC1)CCC1c(ccc(F)c1F)c1F Chemical compound CC(CC1)CCC1C(CC1)CCC1c(ccc(F)c1F)c1F ROXOIDFLXLKFIH-UHFFFAOYSA-N 0.000 description 1
- NBPRBIYGPIZUBP-UHFFFAOYSA-N CC(CC1)CCC1C1COC(c(ccc(F)c2F)c2F)OC1 Chemical compound CC(CC1)CCC1C1COC(c(ccc(F)c2F)c2F)OC1 NBPRBIYGPIZUBP-UHFFFAOYSA-N 0.000 description 1
- GWATXULGNZYGNH-UHFFFAOYSA-N CC(CC1)CCC1C1COC(c(ccc(OC(F)(F)F)c2F)c2F)OC1 Chemical compound CC(CC1)CCC1C1COC(c(ccc(OC(F)(F)F)c2F)c2F)OC1 GWATXULGNZYGNH-UHFFFAOYSA-N 0.000 description 1
- SSGXNYBVDISVRO-UHFFFAOYSA-N CC(CC1)CCC1c1ccc(-c(ccc(OC(F)(F)F)c2F)c2F)c(F)c1 Chemical compound CC(CC1)CCC1c1ccc(-c(ccc(OC(F)(F)F)c2F)c2F)c(F)c1 SSGXNYBVDISVRO-UHFFFAOYSA-N 0.000 description 1
- SVMWEXXLHLULEL-UHFFFAOYSA-N CCC1COC(C(CC2)CCC2c(ccc(F)c2F)c2F)OC1 Chemical compound CCC1COC(C(CC2)CCC2c(ccc(F)c2F)c2F)OC1 SVMWEXXLHLULEL-UHFFFAOYSA-N 0.000 description 1
- KORMYSCDCHFFMN-UHFFFAOYSA-N CCCC(CC1)CCC1C1CCC(CC)CC1 Chemical compound CCCC(CC1)CCC1C1CCC(CC)CC1 KORMYSCDCHFFMN-UHFFFAOYSA-N 0.000 description 1
- VDXVHNIYCHTFIC-UHFFFAOYSA-N CCCCCCC(C)Oc(c(F)cc(C(CC1)CCC1C1CCC(CCC)CC1)c1)c1F Chemical compound CCCCCCC(C)Oc(c(F)cc(C(CC1)CCC1C1CCC(CCC)CC1)c1)c1F VDXVHNIYCHTFIC-UHFFFAOYSA-N 0.000 description 1
- IZZBFRHHMRXPLG-UHFFFAOYSA-N Cc(cc1)ccc1-c(cc1)ccc1-c(ccc(OC(F)(F)F)c1F)c1F Chemical compound Cc(cc1)ccc1-c(cc1)ccc1-c(ccc(OC(F)(F)F)c1F)c1F IZZBFRHHMRXPLG-UHFFFAOYSA-N 0.000 description 1
- UEMGWPRHOOEKTA-UHFFFAOYSA-N Fc1cc(F)ccc1 Chemical compound Fc1cc(F)ccc1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
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Abstract
本發明提供了一種含有2,3,4-三取代苯的液晶化合物、其液晶組合物及包含該液晶化合物或液晶組合物的液晶顯示元件。該液晶組合物具有較低的黏度,可以實現快速回應,同時具有適中的介電異方性△ε、適中的光學異方性△n、高的對熱和光的穩定性。包含該液晶組合物的液晶顯示元件具有較寬的向列相溫度範圍、合適的雙折射率異方性、非常高的電阻率、良好的抗紫外線性能、高電荷保持率以及低蒸汽壓等性能,尤其是該液晶化合物、液晶組合物具有光穿透率高的優勢。
Description
本發明涉及液晶顯示領域,具體涉及一種含有2,3,4-三取代苯的液晶化合物、其液晶組合物及包含該液晶化合物或液晶組合物的液晶顯示元件。
目前,液晶化合物的應用範圍拓展的越來越廣,其可應用於多種類型的顯示器、電光器件、感測器等中。用於上述顯示領域的液晶化合物的種類繁多,其中向列相液晶應用最為廣泛。向列相液晶已經應用在無源TN、STN矩陣顯示器和具有TFT有源矩陣的系統中。
對於薄膜電晶體技術(TFT-LCD)應用領域,近年來市場雖然已經非常巨大,技術也逐漸成熟,但人們對顯示技術的要求也在不斷的提高,尤其是在實現快速回應,降低驅動電壓以降低功耗等方面。液晶材料作為液晶顯示器重要的光電子材料之一,對改善液晶顯示器的性能發揮重要的作用。
作為液晶材料,需要具有良好的化學和熱穩定性以及對電場和電磁輻射的穩定性。而作為薄膜電晶體技術(TFT-LCD)用液晶材料,不僅需要具有如上穩定性外,還應具有較寬的向列相溫度範圍、合適的雙折射率異方性、非常高的電阻率、良好的抗紫外線性能、高電荷保持率以及低蒸汽壓等性能。
對於動態畫面顯示應用,消除顯示畫面殘影和拖尾,要求液晶具有很快的回應速度,因此要求液晶具有較低的旋轉黏度γ1;另外,對於可擕式設備,為了降低設備能耗,希望液晶的驅動電壓盡可能低;而對於電視等用途的顯示器來說,對於液晶的驅動電壓要求不是那麼的低。
液晶化合物的黏度,尤其是旋轉黏度γ1直接影響液晶加電後的回應時間,不管是上升時間(ton)還是下降時間(toff),都與液晶的旋轉黏度γ1成正比關係,上升時間(ton)由於與液晶盒和驅動電壓有關,可以藉由加大驅動電壓的方法與降低液晶盒盒厚來調節;而下降時間(toff)與驅動電壓無關,主要是與液晶的彈性常數與液晶盒盒厚有關,盒厚的下降會降低下降時間(toff),而不同顯示模式下,液晶分子的運動方式不一樣,TN、IPS、VA三種模式分別與平均彈性常數K、扭曲彈性常數、彎曲彈性常數成反比關係。
依照液晶連續體理論,各種不同的液晶在外力(電場、磁場)作用下發生形變後,會藉由分子間的相互作用,會“回彈”回原來的形狀;同樣的,液晶也是由於分子間的相互作用力形成“黏度”。液晶分子的微小變化,會使液晶的常規參數性能發生明顯的變化,這些變化有的是有一定規律的,有的似乎不易找到規律,對於液晶分子間的相互作用也會產生明顯的影響,這些影響非常微妙,至今也沒有形成很完善的理論解釋。
液晶的黏度與液晶分子結構有關,研究不同液晶分子形成的液晶體系的黏度與液晶分子結構之間的關係是液晶配方工程師的重要任務之一。
液晶面板能耗高的原因是只有大約5%左右的背光才能夠穿透顯示器件,而被人眼捕獲,絕大部分光是被“浪費”了的。如果能夠開發出光穿透率
高的液晶,即能夠降低背光強度,從而實現節省能耗的目的,延長設備的使用時間。
本發明的目的在於提供一種含有2,3,4-三取代苯的液晶化合物、其液晶組合物及包含該液晶化合物或液晶組合物的液晶顯示元件,其中本文中所指的液晶顯示元件可包含液晶顯示器。該液晶組合物具有較低的黏度,可以實現快速回應,同時具有適中的介電異方性△ε、適中的光學異方性△n、高的對熱和光的穩定性。包含該液晶組合物的液晶顯示元件具有較寬的向列相溫度範圍、合適的雙折射率異方性、非常高的電阻率、良好的抗紫外線性能、高電荷保持率以及低蒸汽壓等性能,尤其是該液晶化合物、液晶組合物具有光穿透率高的優勢。
其中,R0、R1、R3各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為
1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R0、R1、R3所示基團中任意一個或多個不相連的CH2可以被環戊基、環丁基、環丙基或-O-替代;Y表示乙基或乙烯基;R2表示F、OCF3、OCHF2、OCH2F;、、、各自獨立地表示、、、、、或任意氟代苯的其中一種;m、n各自獨立地表示1或2。
式I所示化合物,m、n都表示1時,為三環化合物,具有較好的溶解性,在液晶中可以添加較多的份數,比如10%,同時具有較低的黏度;m、n其中一個表示2時,為四環化合物,具有很高的清亮點,對於提升液晶的清亮點非常有幫助,但是溶解性較差,添加量一般較小,比如5%;m、n都表示2時,具有非常高的清亮點,溶解性進一步下降,比如1%。環數量的不同,液晶的性能會表現出一些差異,但是與式II-B搭配使用都具有提升穿透率的性能,同時具有很低的黏度等性能,尤其適用於IPS顯示模式。
所述一種或多種式I所示化合物較佳為式I1-I24所示化合物中的一種或多種化合物;所述式II所示化合物較佳包含式II1至II10化合物的一種或多種
化合物;所述一種或兩種式II-B所示化合物較佳為式II-B-1至II-B-2所示化合物中的一種或兩種化合物,
其中,R11各自獨立地表示碳原子數為1-6的烷基、原子數為2-6的烯基。
所述液晶組合物式I所示化合物質量百分比含量較佳為0.5-50%,式II-B質量百分比含量為較佳為5-65%,一種或多種除II-B之外的式II所示化合物質量百分比含量較佳為0-30%。
其中,R4表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基;且R4中任一個或多個CH2可以被環戊基、環丁基或環丙基替代;、、各自獨立地表示:、、、、、、或中的一種或兩種;m表示1或2;Z1、Z2各自獨立地表示單鍵、-CF2O-、-CH2CH2-或-CH2O-;
Y2表示F、氟取代的碳原子數為1-5的烷基、氟取代的碳原子數為1-5的烷氧基、氟取代的碳原子數為2-5的鏈烯基或氟取代的碳原子數為3-8的鏈烯氧基。
其中,X1、X2各自獨立的表示H或F,但在同一分子式中不能同時為F,也不能同時為H;R4各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈
烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R4所示基團中任一個CH2可以被環戊基、環丁基或環丙基替代;(F)各自獨立地表示H或F;Y2各自獨立地表示F、氟取代的碳原子數為1-5的烷基、氟取代的碳原子數為1-5的烷氧基、氟取代的碳原子數為2-5的鏈烯基、氟取代的碳原子數為3-8的鏈烯氧基。
其中,R5、R6各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R5、R6所示基團中任一個CH2可以被環戊基、環丁基或環丙基替代;Z3、Z4各自獨立地表示單鍵、-CH2CH2-或-CH2O-;、各自獨立地表示、、、、、或中的一種或多種;m表示1或2;n表示0,1或2。
其中,R5、R6各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10
的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R5、R6所示基團中任一個CH2可以被環戊基、環丁基或環丙基替代。
其中,R7、R8各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R7、R8所示基團中任一個CH2可以被環戊基、環丁基或環丙基替代。
其中,R1表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且R1所示基團中任意一個或多個不相連的CH2可以被環戊基、環丁基、環丙基或-O-替代;Y表示乙基或乙烯基;m、n各自獨立的表示1或2;、表示、、、、、、或中的一種或兩種條件是,當m+n=2,表示或且R2表示F時,不能表示。
本發明I-A化合物具有低黏度、較寬的折射率範圍、中等的正的介電異方性、尤其是同時具有較大的垂直方向的折射率,而且對光和熱穩定,是一類通用的提升垂直方向介電異方性的液晶化合物,而不會給平行方向介電異方性給出太大的提高。
其中,R11各自獨立地表示碳原子數為1-6的烷基或原子數為2-6的烯基。
本發明更涉及一種包含上述液晶化合物或液晶組合物的液晶顯示元件,所述液晶顯示元件為有源矩陣顯示元件或無源矩陣顯示元件。
合成方法:
a:甲苯 乙醇 水 Na2CO3 Pd(PPh3)4
本發明液晶化合物具有合成簡便,成本低;介電適中,尤其是具有較大的垂直、平行介電;黏度低;較為廣泛的折射率;可以使用於各類液晶顯示模式。
本發明所提供的液晶化合物、液晶組合物中更可以加入各種功能的摻雜劑,摻雜劑含量較佳為0.01-1%之間,這些摻雜劑主要是抗氧化劑、紫外線吸收劑、手性劑。
該液晶組合物具有較低的黏度,可以實現快速回應,同時具有適中的介電異方性△ε、適中的光學異方性△n、高的對熱和光的穩定性。包含該液晶組合物的液晶顯示元件具有較寬的向列相溫度範圍、合適的雙折射率異方性、非常高的電阻率、良好的抗紫外線性能、高電荷保持率以及低蒸汽壓等性能,尤其是該液晶化合物、液晶組合物具有光穿透率高的優勢。
下面結合具體實施例對本發明作進一步闡述,但本發明並不限於以下實施例。所述方法如無特別說明均為常規方法。所述原材料如無特別說明均能從公開商業途徑而得。
反應過程一般藉由TLC監控反應的進程,反應結束的後處理一般是水洗、萃取、合併有機相後乾燥、減壓下蒸除溶劑,以及重結晶、柱層析,本發明所屬技術領域中具有通常知識者都能夠按照下面的描述來實現本發明。
本說明書中的百分比為質量百分比,溫度為攝氏度(℃),其他符號的具體意義及測試條件如下:Cp表示液晶清亮點(℃),DSC定量法測試;S-N表示液晶的晶態到向列相的熔點(℃);△n表示光學異方性,no為尋常光的折射率,ne為非尋常光的折射率,測試條件為25±2℃,589nm,阿貝折射儀測試;△ε表示介電異方性,△ε=ε∥-ε⊥,其中,ε∥為平行於分子軸的介電常數,ε⊥為垂直於分子軸的介電常數,測試條件為25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1測試;γ1表示旋轉黏度(mPa.s),測試條件為25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1測試;ρ表示電阻率(Ω.cm),測試條件為25±2℃,測試儀器為TOYO SR6517高阻儀和LE-21液體電極。
VHR表示電壓保持率(%),測試條件為20±2℃、電壓為±5V、脈衝寬度為10ms、電壓保持時間16.7ms。測試設備為TOYO Model6254液晶性能綜合測試儀。
τ表示回應時間(ms),的測試儀器為DMS-501,測試條件為25±0.5℃,測試盒為3.3微米IPS測試盒,電極間距和電極寬度均為10微米,摩擦方向與電極夾角為10°。
T(%)表示透過率,T(%)=100%*亮態(Vop)亮度/光源亮度,測試設備DMS501,測試條件為25±0.5℃,測試盒為3.3微米IPS測試盒,電極間距和電極寬度均為10微米,摩擦方向與電極夾角為10°
本發明申請實施例液晶單體結構用代碼表示,液晶環結構、端基、連接基團的代碼表示方法見下表(一)、表(二)
舉例:
C(5)CCV1
3B B(3F)B(3F,5F)CF2OB(3F,4F,5F)
實施例1:
1000ml三口瓶中投入0.2mol丙基聯苯硼酸,0.21mol 2,3,4-三氟溴苯,300ml甲苯,300ml乙醇,200ml水,0.24mol碳酸鈉,1g四三苯基膦鈀,加熱回流反應5小時,常規處理:石油醚溶解過矽膠柱,無水乙醇重結晶得到白色晶體49.4g,收率76%,Gc:99.91%。
△n[589nm,25℃]:0.222
Cp:106℃
△ε[1KHz,25℃]:4.3
△n[589nm,25℃]:0.332
Cp:229℃
△ε[1KHz,25℃]:6.9
△n[589nm,25℃]:0.250
Cp:241℃
△ε[1KHz,25℃]:6.8
△n[589nm,25℃]:0.091
Cp:56℃
△ε[1KHz,25℃]:15
△n[589nm,25℃]:0.340
Cp:110℃
△ε[1KHz,25℃]:9.3
△n[589nm,25℃]:0.242
Cp:119℃
△ε[1KHz,25℃]:7.3
實施例2
實施例3
實施例4
對比例1
將實施例4式I化合物3CBB(2F,3F,4F)替換為常見的3CBB(3F,4F,5F);3BBB(2F,3F,4F)替換為常見的3BBB(3F,4F,5F);3CCB(2F,3F,4F)替換為常見的3CCB(3F,4F,5F),得到對比例1組合物,ε⊥從3.8降低為3.1,測試其透過率:對比例1組合物透過率較實施例4降低8%。
實施例5
實施例6
實施例7
本發明液晶化合物具有較低的黏度,較好的對光和熱的穩定性,適合於調節快速回應的,具有高透過率的液晶化合物。
本發明液晶組合物具有較低的黏度,較好的對光和熱的穩定性,較寬的折射率,較寬的向列相溫度範圍,具有調節快速回應、高透過率的優良特性,尤其是適合用於IPS模式。
Claims (3)
- 一種包含如請求項1或2所述之液晶化合物的液晶顯示元件,其中所述液晶顯示元件為有源矩陣顯示元件或無源矩陣顯示元件。
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CN201610862010.5A CN107880900B (zh) | 2016-09-29 | 2016-09-29 | 含有2,3,4-三取代苯的液晶化合物及其组合物 |
CN201610862010.5 | 2016-09-30 |
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TW202120670A TW202120670A (zh) | 2021-06-01 |
TWI755897B true TWI755897B (zh) | 2022-02-21 |
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TW106124197A TW201829748A (zh) | 2016-09-29 | 2017-07-19 | 含有2,3,4-三取代苯的液晶化合物、其組合物及其液晶顯示元件 |
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US (1) | US10767113B2 (zh) |
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CN108003893B (zh) * | 2016-11-02 | 2021-08-03 | 石家庄诚志永华显示材料有限公司 | 一种高垂直介电液晶化合物、液晶组合物、液晶显示器件 |
US11326102B2 (en) | 2017-09-08 | 2022-05-10 | Merck Patent Gmbh | Liquid-crystalline medium and liquid-crystal display comprising the same |
CN110484279B (zh) * | 2018-05-14 | 2022-08-09 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及液晶显示元件、液晶显示器 |
CN111040776B (zh) * | 2018-10-12 | 2023-04-07 | 石家庄诚志永华显示材料有限公司 | 液晶组合物、液晶显示元件、液晶显示器 |
CN111117663B (zh) * | 2018-10-30 | 2022-02-11 | 江苏和成显示科技有限公司 | 液晶组合物及其液晶显示器件 |
WO2021253624A1 (zh) * | 2020-06-16 | 2021-12-23 | 石家庄诚志永华显示材料有限公司 | 液晶组合物、液晶显示元件或液晶显示器 |
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- 2017-07-19 TW TW106124197A patent/TW201829748A/zh unknown
- 2017-09-25 US US15/714,234 patent/US10767113B2/en active Active
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TW202120670A (zh) | 2021-06-01 |
US20190390113A9 (en) | 2019-12-26 |
TW201829748A (zh) | 2018-08-16 |
CN107880900B (zh) | 2021-01-15 |
US20180094191A1 (en) | 2018-04-05 |
CN107880900A (zh) | 2018-04-06 |
US10767113B2 (en) | 2020-09-08 |
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