KR20230017306A - A liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof - Google Patents

Abstract

I

NThe present application relates to a liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof. The liquid crystal composition includes at least one compound of formula I and at least one compound of formula N.

I

N

Description

A liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof

This application belongs to the field of liquid crystal technology, and relates to a liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof.

The liquid crystal material is a mixture of rod-shaped organic small molecule compounds having not only liquid fluidity at a constant temperature but also crystal anisotropy. The liquid crystal display device operates by using the optical anisotropy and dielectric anisotropy of the liquid crystal material itself, and is currently widely used. The liquid crystal display device has phase change (PC), twist nematic (TN), super twisted nematic (STN), and dynamic scattering (DS) depending on the operating mode of the liquid crystal molecules. , ferroelectric liquid crystal (FLC), guest-host (GH), electrically controlled birefringence (ECB), optically compensated bend (OCB), plane-aligned switching (IPS, in-plane switching), vertical alignment (VA), fringe field switching (FFS), and field-induced photo-reactive alignment (FPA).

In liquid crystal display applications, the effect of contrast on the visual effect is key. Generally, the higher the contrast, the clearer and more prominent the image, the brighter and more colorful the color, and the lower the contrast, the duller the overall image. High contrast is of great help to the sharpness of images, expression of detail and expression of gray levels. High contrast products have advantages in terms of both black and white contrast, sharpness and integrity. Contrast also has a great effect on the display effect of dynamic images. Since contrast is relatively fast in dynamic images, the higher the contrast, the easier it is to distinguish this conversion process with the naked eye.

According to research, the most important factor affecting the contrast of a liquid crystal display device is the light leakage of the liquid crystal material, and the main factor affecting the light leakage is light scattering (LC _Scattering ). The relational expression is:

,LC Scattering ∝

,

Here, d represents the spacing of the liquid crystal cell, n _e represents the refractive index of extraordinary light, and n _o represents the refractive index of normal light. As shown in the above relationship, LC scattering and K _ave are inversely proportional, and when K _ave becomes large, light leakage of the liquid crystal material can be reduced.

In addition, the relational expression between contrast (CR) and luminance (L) is as follows:

CR = L ₂₅₅ /L ₀ × 100%;

Here, L ₂₅₅ is the on-state luminance, and L ₀ is the off-state luminance. It can be seen that the change in L ₀ significantly affects CR. In the off state, L ₀ is independent of the dielectric of the liquid crystal molecule and related to the LC Scattering of the liquid crystal material itself; The smaller the LC scattering, the smaller L ₀ , and the CR is significantly improved accordingly.

Patent application CN107973766A discloses a liquid crystal compound of an oxyfluorene derivative containing a cycloalkyl group, the structure of which is as follows:

,

,

Here, H represents one of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a 2-tetrahydrofuryl group; Z represents one of a single bond, -CH ₂ -, -O-, -CH ₂ CH ₂ - or -CH ₂ O-; X represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 7 carbon atoms, or an alkoxy group having 1 to 7 carbon atoms.

The liquid crystal compound of the above-described oxyfluorene derivative having a cycloalkyl group has excellent miscibility with other liquid crystal compounds, and thus, low-temperature stability is improved. However, the transmittance of liquid crystal compositions containing these compounds needs to be further improved.

Therefore, it is expected that a liquid crystal composition having higher transmittance and higher contrast will be developed based on the prior art, to meet the demand for ever-improving visual effects for liquid crystal display devices.

The present application provides a relatively large absolute value of dielectric anisotropy, a relatively large normal permittivity, a relatively large ratio of normal permittivity to absolute permittivity, a relatively large K _ave value, a relatively good transmittance and a relatively long cold storage while maintaining an appropriate clearing point and appropriate optical anisotropy. It is an object of the present invention to provide a liquid crystal composition having time.

To this end, the present application adopts the following technical measures:

As a first aspect, the present application provides a liquid crystal composition containing a dibenzo derivative, the liquid crystal composition comprising:

At least one compound of formula I

I; 및

I; and

Including one or more compounds of the general formula N,

N,

N,

here,

,

또는

을 나타내며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기,

,

또는

중의 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- 또는 -O-CO-로 대체될 수 있으며, 상술한 라디칼 중 하나 또는 둘 이상의 -H는 각각 독립적으로 -F 또는 -Cl에 의해 치환될 수 있으며; R_x는 -H, 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기를 나타내며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기 중의 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- 또는 -O-CO-로 대체될 수 있으며, 하나 또는 둘 이상의 -H는 각각 독립적으로 -F 또는 -Cl에 의해 치환될 수 있으며, 상기 R_x는 고리

중의 임의의 탄소 원자와 연결되며; R_N1 및 R_N2는 각각 독립적으로 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기,

,

또는

을 나타내며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기 중의 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- 또는 -O-CO-로 대체될 수 있으며; 고리

및 고리

는 각각 독립적으로

,

,

또는

을 나타내며, 여기서,

,

및

중의 하나 또는 둘 이상의 -CH₂-는 -O-로 대체될 수 있으며, 하나 또는 둘 이상의 고리 중의 단일결합은 이중결합으로 대체될 수 있으며, 여기서,

및

중의 하나 또는 둘 이상의 -H는 -F, -Cl, -CN, -CH₃ 또는 -OCH₃에 의해 치환될 수 있으며, 하나 또는 둘 이상의 고리 중 -CH= 는 -N=으로 대체될 수 있으며; “하나 또는 둘 이상의 고리 중 -CH=는 -N=으로 대체될 수 있으며” 중 “하나 또는 둘 이상”은 -N=에 의해 대체되는 -CH=의 수를 의미하며, 본 출원에서 동일한 표현 방식은 모두 동일한 의미를 가지며; 고리

는

을 나타내고, 여기서, X₂는 -O- 또는-S-를 나타내고, 상술한 라디칼 중 하나 또는 둘 이상의 고리에서 단일결합은 이중결합으로 대체될 수 있으며; 고리

및 고리

는 각각 독립적으로

또는

을 나타내며, 여기서,

중의 하나 또는 둘 이상의 -CH₂-는 -O-로 대체될 수 있으며, 하나 또는 둘 이상의 고리 중의 단일결합은 이중결합으로 대체될 수 있으며, 여기서,

중의 하나 또는 둘 이상의 -H는 -F, -Cl 또는 -CN에 의해 치환될 수 있으며, 하나 또는 둘 이상의 고리 중 -CH=는 -N=으로 대체될 수 있으며;R ₁ is -H, halogen, a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, the linear or branched alkyl group containing 1 to 12 carbon atoms,

,

or

-CH ₌ CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO -, and one or more -H of the aforementioned radicals may each independently be substituted by -F or -Cl; R _x represents -H, a straight-chain or branched alkyl group containing 1 to 12 carbon atoms, and one of the straight-chain or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - may each independently be replaced by -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO-, one or two Each of the above -H may be independently substituted with -F or -Cl, wherein R _x is a ring

connected to any carbon atom in; R _N1 and R _N2 are each independently a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, one of the linear or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO-; ring

and rings

are each independently

,

,

or

represents, where,

,

and

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

and

one or more -H of may be substituted by -F, -Cl, -CN, -CH ₃ or -OCH ₃ , and -CH= of one or more rings may be replaced by -N=; "One or two or more of the rings -CH= can be replaced by -N=" means the number of -CH= replaced by -N=, the same expression in this application all have the same meaning; ring

Is

, wherein X ₂ represents -O- or -S-, and a single bond in one or more rings of the aforementioned radicals may be replaced by a double bond; ring

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

one or more -H of may be substituted by -F, -Cl or -CN, and -CH= of one or more rings may be replaced by -N=;

X ₁ is -O-. represents -S-, -CO-, -CF ₂ -, -NH- or -NF-;

Y ₁ and Y ₂ each independently represent -H, halogen, a halogenated alkyl group or non-halogenated alkyl group containing 1 to 3 carbon atoms, a halogenated alkoxy group or non-halogenated alkoxy group containing 1 to 3 carbon atoms. ;

Z represents -(CH ₂ ) _a O- or -(CH ₂ ) _a S-, where a is an integer from 0 to 7 such as 1, 2, 3, 4, 5, etc.;

Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -CH=CH-, - C≡C-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -(CH ₂ ) ₄ -, -CF ₂ O- or -OCF ₂ -;

Z _N1 and Z _N2 are each independently a single bond, -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -(CH ₂ ) ₄ -, -CF ₂ O- or -OCF ₂ -;

L _N1 and L _N2 each independently represent -H, an alkyl group containing 1 to 3 carbon atoms, or halogen;

는 동일하거나 상이하고, Z₁은 동일하거나 상이하며, n₂=2일 경우, 고리

는 동일하거나 상이하고, Z₂는 동일하거나 상이하며; 또한n ₁ and n ₂ each independently represent 0, 1 or 2, and when n ₁ =2, a ring

are the same or different, Z ₁ are the same or different, and when n ₂ =2, a ring

are the same or different, Z ₂ are the same or different; also

는 동일하거나 상이하고, Z_N1은 동일하거나 상이하다.n _N1 represents 0, 1, 2 or 3, n _N2 represents 0 or 1, and 0 ≤ n _N1 + n _N2 ≤ 3, when n _N1 =2 or 3, a ring

are the same or different, and Z _N1 are the same or different.

두 개가 존재하며, 이 두 개의

은 동일한 구조 또는 상이한 구조를 가질 수 있으며, 예시적으로, 하나는

이고, 다른 하나는

일 수 있으며; 본 출원에서 “동일하거나 상이하다”는 표현은 모두 동일한 의미를 가지며;For n ₁ =2, the compound

There are two, and these two

may have the same structure or a different structure, illustratively, one

and the other is

can be; In this application, the expressions “the same or different” all have the same meaning;

In this application, "each independently may be substituted for..." means that it may or may not be substituted, that is, it may or may not be substituted, all of which in this application It is included in the protection scope of, and “can be independently substituted by ...” is the same, and the positions to be “replaced” and “substituted” may be arbitrary.

우측의 짧은 직선,

양측의 짧은 직선과 같이, 메틸기를 나타내지 않고 액세스 결합을 나타낸다.In this application, a short straight line on one side or both sides of the radical structure is for example

a short straight line on the right,

As with the short straight lines on both sides, it shows an access bond without showing a methyl group.

In the present application, the number of carbon atoms of a straight-chain or branched alkyl group containing 1 to 12 carbon atoms includes, but is not limited to, 2, 4, 6, 8, 10, and the like.

In this application, halogen includes, but is not limited to, fluorine, chlorine, bromine or iodine, and the like.

This application provides a new type of liquid crystal composition, by introducing a negative liquid crystal compound represented by formula I and blending with a compound of formula N, maintaining a suitable clearing point and suitable optical anisotropy, while maintaining a relatively large absolute value of dielectric anisotropy, a relatively large vertical Permittivity, a relatively large ratio of vertical permittivity to absolute permittivity, a relatively large K _ave value, a relatively good transmittance, and a relatively long low-temperature storage time, and furthermore, a liquid crystal display including the same has a relatively low threshold voltage, a relatively good contrast, and a relatively short response time, relatively good transmittance and relatively good low-temperature stability.

는 산소 원자를 포함하는 5원 헤테로고리 또는 황 원자를 포함하는 5원 헤테로고리 구조이며, 탄소 원자를 포함하는 5원 고리 구조와 비교할 경우, 일반식 I의 화합물을 액정 조성물에 첨가할 경우, 적절한 투명점과 적절한 광학 이방성을 유지하면서 비교적 큰 유전 이방성의 절대값, 비교적 큰 수직 유전율, 비교적 큰 수직 유전율과 절대 유전율의 비율, 비교적 큰 K_ave값, 비교적 우수한 투과율 및 비교적 긴 저온 저장 시간을 구비하는 데에 더 유리하다.In the compound of general formula I of the present application,

Is a 5-membered heterocyclic structure containing an oxygen atom or a 5-membered heterocyclic structure containing a sulfur atom, and when compared with a 5-membered ring structure containing a carbon atom, when the compound of formula I is added to the liquid crystal composition, an appropriate Having a relatively large absolute value of dielectric anisotropy, a relatively large normal permittivity, a relatively large ratio of normal permittivity to absolute permittivity, a relatively large K _ave value, a relatively good transmittance and a relatively long cold storage time while maintaining a clearing point and appropriate optical anisotropy. more favorable for

In the present application, when Z is an alkyleneoxy group or an alkylenethio group structure in the compound of formula I, the overall conjugation effect of the compound of formula I is stronger than the technical solution in which Z represents a straight-chain alkyl group, and the intramolecular After the radicals play a synergistic role, the absolute value of dielectric anisotropy, normal permittivity, ratio of normal permittivity to absolute permittivity, K _ave value, transmittance, cold storage time, etc. all have a clear improvement effect, and in this application, the threshold voltage is low, It was surprisingly found that high contrast, short response time, high transmittance, and low-temperature storage stability are more beneficial for realizing excellent effects.

및 고리

는 각각 독립적으로

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

또는

을 나타낸다.In some embodiments of this application, a ring

and rings

are each independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

indicates

는

,

,

,

,

,

,

또는

을 나타낸다. 본 출원의 일부 구현예에서, X₁은 -O-, -S- 또는 -CO-를 나타내며; 선택적으로 X₁은 -O- 또는 -S-를 나타낸다. 본 출원의 일부 구현예에서, Y₁ 및 Y₂는 각각 독립적으로 -H, -F, -Cl, -CN, -CH₃, -OCH₃, -CF₃ 또는 -OCF₃을 나타내며; 선택적으로, Y₁ 및 Y₂는 각각 독립적으로 -H, -F 또는 -Cl을 나타내며; 선택적으로, Y₁ 및 Y₂는 모두 -F를 나타낸다. 본 출원은 선택적으로 디벤조 유도체의 벤젠 고리에서 -F를 치환할 수 있으며, 다른 치환기와 비교할 경우, 액정 조성물의 유전 이방성의 절대값, 수직 유전율, 수직 유전율과 절대 유전율의 비율, K_ave값, 투과율, 저온 저장 시간을 개선하는 데에 더 도움이 된다. 본 출원의 일부 구현예에서, X₁은 -O-, -S- 또는 -CO-를 나타내고, Y₁ 및 Y₂는 모두 -F를 나타낸다. 본 출원의 일부 구현예에서, a는 0 내지 3의 정수를 나타내고; 선택적으로, a는 1 또는 2를 나타낸다. 본 출원의 일부 구현예에서, Z₁ 및 Z₂는 각각 독립적으로 단일 결합, -O-, -S-, -CH₂O-, -OCH₂-, -CH=CH-, -C≡C-, -CH₂CH₂-, -CF₂O- 또는 -OCF₂-를 나타낸다. 본 출원의 일부 구현예에서, n₁ 및 n₂는 각각 독립적으로 0 또는 1을 나타내고; 선택적으로, n₁은 0을 나타내며; n₂는 0 또는 1을 나타내며; 선택적으로, n₁ 및 n₂는 각각 독립적으로 0을 나타낸다.In some embodiments of this application, a ring

Is

,

,

,

,

,

,

or

indicates In some embodiments of this application, X ₁ represents -O-, -S- or -CO-; Optionally X ₁ represents -O- or -S-. In some embodiments of this application, Y ₁ and Y ₂ each independently represent -H, -F, -Cl, -CN, -CH ₃ , -OCH ₃ , -CF ₃ or -OCF ₃ ; Optionally, Y ₁ and Y ₂ each independently represent -H, -F or -Cl; Optionally, Y ₁ and Y ₂ both represent -F. The present application may optionally substitute -F in the benzene ring of the dibenzo derivative, and when compared with other substituents, the absolute value of the dielectric anisotropy of the liquid crystal composition, the perpendicular permittivity, the ratio of the normal permittivity to the absolute permittivity, K _ave value, It is more conducive to improving transmittance and cold storage time. In some embodiments of this application, X ₁ represents -O-, -S- or -CO-, and Y ₁ and Y ₂ both represent -F. In some embodiments of this application, a represents an integer from 0 to 3; Optionally, a represents 1 or 2. In some embodiments of this application, Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CH ₂ O-, -OCH ₂ -, -CH=CH-, -C≡C- , -CH ₂ CH ₂ -, -CF ₂ O- or -OCF ₂ -. In some embodiments of this application, n ₁ and n ₂ each independently represent 0 or 1; Optionally, n ₁ represents 0; n ₂ represents 0 or 1; Optionally, n ₁ and n ₂ each independently represents 0.

In some embodiments of the present application, the liquid crystal composition includes two or more compounds of Formula I.

In some embodiments of the present application, the liquid crystal composition includes at least one compound of Formula I in which X ₂ is -O- and/or one compound of Formula I in which X ₂ is -S-; Optionally, the liquid crystal composition includes two or more compounds of the general formula I, wherein X ₂ is -O-. The present application selectively combines two or more compounds of the general formula I in which X ₂ is -O-, absolute value of dielectric anisotropy, perpendicular permittivity, ratio of normal permittivity and absolute permittivity, K _ave value, transmittance, It further improves the cold storage time. In some embodiments of this application, when X ₂ is -O-, then X ₁ is -O- or -S-; Optionally, when X ₂ is -O-, then X ₁ is -O-. In some embodiments of this application, when X ₂ is -S-, then X ₁ is -O- or -S-; Optionally, when X ₂ is -S-, then X ₁ is -S-.

In some embodiments of this application, R ₁ is optionally a straight or branched chain alkyl group containing 1 to 10 carbon atoms, a straight or branched chain alkoxy group containing 1 to 9 carbon atoms, 1 carbon atom a straight-chain or branched alkylthio group containing 2 to 9 carbon atoms or a straight-chain or branched alkenyl group containing 2 to 10 carbon atoms; R ₁ is further optionally a straight-chain or branched alkyl group containing 1 to 8 carbon atoms, a straight-chain or branched alkoxy group containing 1 to 7 carbon atoms, or a straight-chain containing 1 to 7 carbon atoms. or a branched alkylthio group, or a straight-chain or branched alkenyl group containing 2 to 8 carbon atoms; R ₁ is further optionally a straight-chain or branched alkyl group containing 1 to 5 carbon atoms, a straight-chain or branched alkoxy group containing 1 to 4 carbon atoms, or a straight-chain or branched alkoxy group containing 1 to 4 carbon atoms. A straight-chain or branched alkylthio group, or a straight-chain or branched alkenyl group containing 2 to 5 carbon atoms.

In some embodiments of this application, R _x represents -H or a straight chain alkyl group containing 1 to 6 carbon atoms.

In some embodiments of the present application, the compound of formula I comprises 0.1% to 40% by weight of the liquid crystal composition, such as 0.1%, 1%, 2%, 4%, 6%, 8%, 10% , 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, etc.; Optionally, the compound of formula I comprises 0.1% to 30% by weight of the liquid crystal composition; Optionally, the compound of formula I accounts for 0.5% to 30% by weight of the liquid crystal composition.

및 고리

는 각각 독립적으로

,

,

,

,

,

,

,

,

,

또는

을 나타낸다.In some embodiments of this application, a ring

and rings

are each independently

,

,

,

,

,

,

,

,

,

or

indicates

In some embodiments of this application, Formula N is selected from any one or combination of two or more of the following compounds:

N-1;

N-1;

N-2;

N-2;

N-3;

N-3;

N-4;

N-4;

N-5;

N-5;

N-6;

N-6;

N-7;

N-7;

N-8;

N-8;

N-9;

N-9;

N-10;

N-10;

N-11;

N-11;

N-12;

N-12;

N-13;

N-13;

N-14;

N-14;

N-15;

N-15;

N-16;

N-16;

N-17;

N-17;

N-18;

N-18;

N-19;

N-19;

N-20;

N-20;

N-21; 및

N-21; and

N-22.

N-22.

및 고리

는 각각 독립적으로

또는

을 나타내며, 여기서,

중의 하나 또는 둘 이상의 -CH₂-는 -O-로 대체될 수 있으며, 여기서,

중의 하나 또는 둘 이상의 -H는 -F, -Cl 또는 -CN에 의해 치환될 수 있으며, 하나 또는 둘 이상의 고리 중 -CH=는 -N=으로 대체될 수 있다. 본 출원의 일부 구현예에서, Z_N1 및 Z_N2는 각각 독립적으로 단일 결합, -CH₂O-, -OCH₂-, -CH=CH-, -CH₂CH₂-, -CF₂CF₂-, -CF₂O- 또는 -OCF₂-를 나타낸다. 본 출원의 일부 구현예에서, 0＜n_N1+n_N2≤3이다. 본 출원의 일부 구현예에서, n_N1=1이고 n_N2=0일 경우, 고리

는 방향족이 아니며; n_N1=2이고 고리

가

을 나타낼 경우, R_N1은 알케닐기가 아니다.In some embodiments of this application, a ring

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, wherein

One or more -H of may be substituted by -F, -Cl or -CN, and -CH= of one or more rings may be replaced by -N=. In some embodiments of this application, Z _N1 and Z _N2 are each independently a single bond, -CH ₂ O-, -OCH ₂ -, -CH=CH-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ - , -CF ₂ O- or -OCF ₂ -. In some implementations of the present application, 0<n _N1 +n _N2 ≤3. In some embodiments of this application, when n _N1 =1 and n _N2 =0, a ring

is not aromatic; n _N1 =2 and a ring

go

When representing, R _N1 is not an alkenyl group.

In some embodiments of this application, the compound of Formula N is Formula N-1, Formula N-2, Formula N-3, Formula N-4, Formula N-5, Formula N-6 , general formula N-8, general formula N-9, general formula N-10, general formula N-11, general formula N-12, general formula N-13, general formula N-17, general formula N-18, general formula any one or a combination of two or more of the compounds of Formulas N-19 and Formulas N-21; Optionally, the compound of formula N is of formula N-2, formula N-3, formula N-5, formula N-6, formula N-11, formula N-12 and formula N- Any one or a combination of two or more of the 13 compounds is included.

The present application can select a compound of formula N having a specific structure described above, and when these compounds are used in combination with a compound of formula I, the absolute value of dielectric anisotropy, perpendicular permittivity, perpendicular permittivity and absolute permittivity of the liquid crystal composition Further improvements in ratio, K _ave value, permeability, and cold storage time can be achieved.

In some embodiments of the present application, the compound of formula N includes at least one compound of formula N-3 and/or formula N-6. In some embodiments of the present application, the compound of formula N includes at least one compound of formula N-12, formula N-13, or formula N-17. In some embodiments of the present application, the compound of formula N includes at least one compound of formula N-3 and/or formula N-6, wherein formula N-12 and/or formula N- At least 1 sort(s) of 13 compounds is included. In some embodiments of the present application, the compound of formula N includes at least one compound of formula N-10 and/or formula N-11.

In some embodiments of the present application, R _N1 and R _N2 are optionally each independently a straight-chain or branched alkyl group containing 1 to 10 carbon atoms, or a straight-chain or branched-chain alkoxy group containing 1 to 9 carbon atoms. group, or a straight-chain or branched alkenyl group containing 2 to 10 carbon atoms; R _N1 and R _N2 are further optionally each independently a straight-chain or branched alkyl group containing 1 to 8 carbon atoms, a straight-chain or branched alkoxy group containing 1 to 7 carbon atoms, or 2 carbon atoms It is a linear or branched alkenyl group containing 8 to 8; R _N1 and R _N2 are optionally each independently a straight-chain or branched alkyl group containing 1 to 5 carbon atoms, a straight-chain or branched chain alkoxy group containing 1 to 4 carbon atoms, or 2 to 5 carbon atoms. It is a linear or branched alkenyl group containing 5 members.

In some embodiments of the present application, the compound of formula N comprises 0.1% to 60% by weight of the liquid crystal composition, such as 0.1%, 1%, 2%, 4%, 6%, 8%, 10% , 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44 %, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, etc.; Optionally, the compound of formula N comprises 0.1% to 50% by weight of the liquid crystal composition; Optionally, the compound of formula N accounts for 5% to 50% by weight of the liquid crystal composition.

In some embodiments of the present application, the liquid crystal composition includes one or more compounds of general formula M:

M,

M,

here,

,

또는

을 나타내며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기 중의 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- 또는 -O-CO-로 대체될 수 있으며;R _M1 and R _M2 are each independently a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, one of the linear or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO-;

, 고리

및 고리

는 각각 독립적으로

또는

을 나타내며, 여기서,

중의 하나 또는 둘 이상의 -CH₂-는 -O-로 대체될 수 있으며, 하나 또는 둘 이상의 고리 중의 단일결합은 이중결합으로 대체될 수 있으며, 여기서,

중의 하나 또는 둘 이상의 -H는 할로겐에 의해 대체될 수 있으며;ring

, ring

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

one or more -H of may be replaced by halogen;

Z _M1 and Z _M2 are each independently a single bond -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -C≡C-, -CH=CH-, -CH ₂ CH ₂ - or -(CH ₂ ) ₄ -; also

는 동일하거나 상이하고, Z_M2는 동일하거나 상이하다.n _M represents 0, 1 or 2, when n _M =2, a ring

are the same or different, and Z _M2 are the same or different.

In the present application, the alkenyl group is optionally selected from a radical represented by any one of formulas (V1) to formula (V9), particularly optionally formula (V1), formula (V2), formula (V8), or formula (V9) is selected from The radicals represented by formulas (V1) to (V9) are represented as follows:

,

,

Here, * represents a carbon atom in the bonded ring structure.

In the present application, the alkenyloxy group is optionally selected from a radical represented by any one of formulas (OV1) to (OV9), particularly optionally formulas (OV1), (OV2), (OV8), or (OV9). ) is selected from The radicals represented by formulas (OV1) to (OV9) are represented as follows:

,

,

Here, * represents a carbon atom in the bonded ring structure.

In some embodiments of this application, the compound of formula M is selected from any one or combination of two or more of the following compounds:

M-1;

M-1;

M-2;

M-2;

M-3;

M-3;

M-4;

M-4;

M-5;

M-5;

M-6;

M-6;

M-7;

M-7;

M-8;

M-8;

M-9;

M-9;

M-10;

M-10;

M-11;

M-11;

M-12;

M-12;

M-13;

M-13;

M-14;

M-14;

M-15;

M-15;

M-16;

M-16;

M-17;

M-17;

M-18;

M-18;

M-19;

M-19;

M-20;

M-20;

M-21;

M-21;

M-22;

M-22;

M-23;

M-23;

M-24;

M-24;

M-25;

M-25;

M-26;

M-26;

M-27;

M-27;

M-28;

M-28;

M-29; 및

M-29; and

M-30.

M-30.

In some embodiments of the present application, the content of the compound of formula M is appropriately adjusted according to necessary properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process suitability, drip marks, burn-in, and dielectric anisotropy. It should be.

In some embodiments of the present application, R _M1 and R _M2 are optionally each independently a straight-chain alkyl group containing 1 to 10 carbon atoms, a straight-chain alkoxy group containing 1 to 9 carbon atoms, or a carbon atom. A straight-chain alkenyl group containing 2 to 10 atoms; R _M1 and R _M2 further optionally each independently represent a straight-chain alkyl group containing 1 to 8 carbon atoms, a straight-chain alkoxy group containing 1 to 7 carbon atoms, or 2 to 8 carbon atoms. A straight-chain alkenyl group containing; R _M1 and R _M2 are further optionally each independently a straight-chain alkyl group containing 1 to 5 carbon atoms, a straight-chain alkoxy group containing 1 to 4 carbon atoms, or a straight-chain alkoxy group containing 2 to 5 carbon atoms. It is a straight-chain alkenyl group containing

In some embodiments of this application, R _M1 and R _M2 are optionally each independently a straight-chain alkenyl group containing 2 to 8 carbon atoms; optionally each independently a straight-chain alkenyl group containing 2 to 5 carbon atoms.

In some embodiments of this application, any one of R _M1 and R _M2 is a straight chain alkenyl group containing 2 to 5 carbon atoms, and the other is a straight chain alkyl group containing 1 to 5 carbon atoms. .

In some embodiments of the present application, R _M1 and R _M2 are optionally each independently a straight-chain alkyl group containing 1 to 8 carbon atoms or a straight-chain alkoxy group containing 1 to 7 carbon atoms; optionally each independently a straight-chain alkyl group containing 1 to 5 carbon atoms or a straight-chain alkoxy group containing 1 to 4 carbon atoms.

In some embodiments of this application, either of R _M1 and R _M2 is a straight chain alkyl group containing 1 to 5 carbon atoms; the other is a straight-chain alkyl group containing 1 to 5 carbon atoms or a straight-chain alkoxy group containing 1 to 4 carbon atoms; Optionally, both R _M1 and R _M2 are each independently a straight-chain alkyl group containing 1 to 5 carbon atoms.

In some embodiments of this application, where reliability is of importance, optionally both R _M1 and R _M2 are alkyl groups; When reducing the volatility of the compound is of interest, optionally both R _M1 and R _M2 are alkoxy groups; Optionally, at least one of R _M1 and R _M2 is an alkenyl group when reducing the viscosity is important.

In some embodiments of the present application, the compound of Formula M is Formula M-1, Formula M-2, Formula M-4, Formula M-6, Formula M-9, Formula M-11 , general formula M-12, general formula M-13, general formula M-14. general formula M-15, general formula M-16, general formula M-19, general formula M-21, general formula M-26, general formula and any one or combination of two or more of the compounds of formula M-28, formula M-29 and formula M-30.

In some embodiments of the present application, the compound of formula M includes at least one compound of formula M-12 and/or formula M-16, wherein formula M-12 and/or formula M- In 16, at least one of R _M1 and R _M2 is an alkenyl group.

In some embodiments of the present application, the compound of formula M comprises from 0.1% to 80% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12% , 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46 %, 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 70%, 72%, 74%, 76%, 78%, etc. occupies; Optionally, the compound of formula M comprises 1% to 60% by weight of the liquid crystal composition; Optionally, the compound of formula M accounts for 5% to 60% by weight of the liquid crystal composition.

Regarding the content of the compound of formula M, if it is necessary to keep the viscosity of the liquid crystal composition of the present application low and to shorten the response time, the lower limit value may optionally be relatively large and the upper limit value may also be relatively large; Furthermore, when the clearing point of the liquid crystal composition of the present application is to be maintained relatively high and the temperature stability is to be maintained well, the lower limit value may optionally be relatively large and the upper limit value may also be relatively large; In order to keep the driving voltage low and increase the absolute value of the dielectric anisotropy, the lower limit value may be lowered and the upper limit value may be lowered selectively.

In some embodiments of the present application, the liquid crystal composition includes any one or a combination of two or more of one or more compounds of formula A-1 and/or compounds of formula A-2,

A-1; 및

A-1; and

A-2,

A-2,

,

또는

을 나타내며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기 중의 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- 또는 -O-CO-로 대체될 수 있으며, 상기 탄소 원자 1개 내지 12개를 포함하는 직쇄 또는 측쇄의 알킬기,

,

또는

중의 하나 또는 둘 이상의 -H는 각각 독립적으로 -F 또는 -Cl에 의해 치환될 수 있으며;Here, R _A1 and R _A2 are each independently a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, one of the linear or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO- may be substituted, and a linear or branched alkyl group containing 1 to 12 carbon atoms,

,

or

one or two or more -H of may each independently be substituted by -F or -Cl;

, 고리

, 고리

및 고리

는 각각 독립적으로,

,

,

또는

을 나타내며, 여기서,

,

및

중의 하나 또는 둘 이상의 -CH₂-는 -O-로 대체될 수 있으며, 하나 또는 둘 이상의 고리 중의 단일결합은 이중결합으로 대체될 수 있으며, 여기서,

및

중의 하나 또는 둘 이상의 -H는 -F, -Cl, -CN, -CH₃ 또는 -OCH₃에 의해 치환될 수 있으며, 하나 또는 둘 이상의 고리 중 -CH= 는 -N=으로 대체될 수 있으며;ring

, ring

, ring

and rings

are each independently,

,

,

or

represents, where,

,

and

One or more of -CH ₂ - may be replaced with -O-, and a single bond in one or more rings may be replaced with a double bond, wherein:

and

one or more -H of may be substituted by -F, -Cl, -CN, -CH ₃ or -OCH ₃ , and -CH= of one or more rings may be replaced by -N=;

Z _A11 , Z _A21 and Z _A22 are each independently a single bond, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -CO-O-, -O-CO-, -O-CO-O-, - CH=CH-, -CF=CF-, -CH ₂ O- or -OCH ₂ -;

L _A11 , L _A12 , L _A13 , L _A21 and L _A22 each independently represent -H, an alkyl group containing 1 to 3 carbon atoms, or halogen;

X _A1 and X _A2 each independently represent a halogen, a halogenated alkyl group or an allogenated alkoxy group containing 1 to 5 carbon atoms, a halogenated alkenyl group or a halogenated alkenyloxy group containing 2 to 5 carbon atoms;

은 동일하거나 상이하고, Z_A11은 동일하거나 상이하며;n _A11 represents 0, 1, 2 or 3, when n _A11 =2 or 3, a ring

are the same or different, Z _A11 are the same or different;

는 동일하거나 상이하며; 또한n _A12 represents 1 or 2, and when n _A12 =2, a ring

are the same or different; also

은 동일하거나 상이하고, Z_A21은 동일하거나 상이하다.n _A2 represents 0, 1, 2 or 3, where n _A2 =2 or 3, a ring

are the same or different, and Z _A21 are the same or different.

In some embodiments of this application, the compound of Formula A-1 is selected from any one or combination of two or more of the following compounds:

A-1-1;

A-1-1;

A-1-2;

A-1-2;

A-1-3;

A-1-3;

A-1-4;

A-1-4;

A-1-5;

A-1-5;

A-1-6;

A-1-6;

A-1-7;

A-1-7;

A-1-8;

A-1-8;

A-1-9;

A-1-9;

A-1-10;

A-1-10;

A-1-11;

A-1-11;

A-1-12;

A-1-12;

A-1-13;

A-1-13;

A-1-14;

A-1-14;

A-1-15;

A-1-15;

A-1-16;

A-1-16;

A-1-17; 및

A-1-17; and

A-1-18,

A-1-18;

,

또는

를 나타내고, 상기 탄소 원자 1개 내지 8개를 포함하는 직쇄 또는 측쇄의 알킬기 중 하나 또는 인접하지 않은 둘 이상의 -CH₂-는 각각 독립적으로 -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- 또는 -O-CO-에 의해 대체될 수 있으며, 상기 탄소 원자 1개 내지 8개를 포함하는 직쇄 또는 측쇄의 알킬기 중 하나 또는 둘 이상의 -H는 각각 독립적으로 -F 또는 -Cl에 의해 치환될 수 있으며; R_v 및 R_w는 각각 독립적으로 -CH₂- 또는 -O-를 나타내며; L_A11, L_A12, L_A11’, L_A12’, L_A14, L_A15 및 L_A16은 각각 독립적으로 -H 또는 -F를 나타내며; L_A13 및 L_A13 ’은 각각 독립적으로 -H 또는 -CH₃을 나타내며; X_A1은 -F, -CF₃ 또는 -OCF₃을 나타내고; v 및 w는 각각 독립적으로 0 또는 1을 나타낸다.Here, R _A1 is a linear or branched alkyl group containing 1 to 8 carbon atoms,

,

or

, wherein one of the linear or branched alkyl groups containing 1 to 8 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO-, and one or two or more -H of the linear or branched alkyl group containing 1 to 8 carbon atoms are independently may be substituted by -F or -Cl; R _v and R _w each independently represent -CH ₂ - or -O-; L _A11 , L _A12 , L _A11 ', L _A12 ', L _A14 , L _A15 and L _A16 each independently represent -H or -F; L _A13 and L _A13 ′ each independently represent -H or -CH ₃ ; X _A1 represents -F, -CF ₃ or -OCF ₃ ; v and w represent 0 or 1 each independently.

In some embodiments of the present application, the compound of formula A-1 accounts for 0.1% to 50% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44% , 46%, 48%, etc.

In some embodiments of this application, the compound of Formula A-2 is selected from any one or combination of two or more of the following compounds,

A-2-1;

A-2-1;

A-2-2;

A-2-2;

A-2-3;

A-2-3;

A-2-4;

A-2-4;

A-2-5;

A-2-5;

A-2-6;

A-2-6;

A-2-7;

A-2-7;

A-2-8;

A-2-8;

A-2-9;

A-2-9;

A-2-10;

A-2-10;

A-2-11;

A-2-11;

A-2-12;

A-2-12;

A-2-13;

A-2-13;

A-2-14;

A-2-14;

A-2-15;

A-2-15;

A-2-16; 및

A-2-16; and

A-2-17,

A-2-17;

Here, R _A2 represents a straight-chain or branched alkyl group containing 1 to 8 carbon atoms, and one of the straight-chain or branched alkyl groups containing 1 to 8 carbon atoms or two or more non-adjacent -CH ₂ - can each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or two or more of the aforementioned radicals -H may each independently be substituted by -F or -Cl; L _A21 , L _A22 , L _A23 , L _A24 and L _A25 each independently represent -H, -F or -Cl; X _A2 represents -F, -CF ₃ , -OCF ₃ or -CH ₂ CH ₂ CH=CF ₂ .

In some embodiments of the present application, the compound of formula A-2 accounts for 0.1% to 50% by weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44% , 46%, 48%, etc.

The liquid crystal composition of the present application may include conventional nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers, or light stabilizers in addition to the above compounds.

Possible dopants that can be selectively added to the liquid crystal composition according to the present application are shown below.

C 15;

C 15;

CB 15;

CB 15;

CM 21;

CM 21;

R/S-811;

R/S-811;

CM 44;

CM 44;

CM 45;

CM 45;

CM 47;

CM 47;

CN;

CN;

R/S-1011;

R/S-1011;

R/S-2011;

R/S-2011;

R/S-3011;

R/S-3011;

R/S-4011; 및

R/S-4011; and

R/S-5011.

R/S-5011.

where * indicates the position of a chiral carbon atom.

In some embodiments of the present application, the dopant comprises 0% to 5% by weight of the liquid crystal composition, and optionally the dopant comprises 0.01% to 1% by weight of the liquid crystal composition.

In addition, additives such as antioxidants and light stabilizers used in the liquid crystal composition of the present application may be selected from the following materials:

Here, n represents a positive integer from 1 to 12, such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, etc. Optionally, the light stabilizer is selected from the light stabilizers indicated below:

,

또는

.

,

or

.

In some embodiments of the present application, the light stabilizer comprises 0% to 5% by weight of the liquid crystal composition, optionally the light stabilizer comprises 0.01% to 1% by weight of the liquid crystal composition; Optionally, the light stabilizer accounts for 0.01% to 0.1% by weight of the liquid crystal composition. As a second aspect, the present application provides a liquid crystal display device comprising the liquid crystal composition of the first aspect.

The present application has the following beneficial effects compared to the prior art: The liquid crystal composition of the present application has a relatively large absolute value of dielectric anisotropy, a relatively large perpendicular permittivity, a relatively large perpendicular permittivity and It has a ratio of absolute permittivity, a relatively large K _ave value, a relatively good transmittance and a relatively long low temperature storage time, so that a liquid crystal display including the same has a relatively low threshold voltage, a relatively good contrast, a relatively short response time, a relatively good transmittance and a relatively long storage time. It has excellent low-temperature stability and has high application value in liquid crystal displays of IPS mode, FFS mode, and VA mode.

Hereinafter, the present application will be described in combination with specific embodiments. It should be noted that the following examples are only examples of the present application, and are used only to explain the present application and not to limit the present application. Other combinations and various improvements may be made within the scope of the present application without departing from the spirit or scope of the present application.

For convenience of expression, in the following examples, the radical structure of the liquid crystal composition is represented by the code shown in Table 1:

[Table 1] Radical structure codes of liquid crystal compounds radical unit structure code radical designation

C 1, 4-cyclohexylidene group

A 2-Oxohexacyclo

D 1,3-dioxane-2,5-diyl group

P 1,4-phenylene group

G 2-fluoro-1,4-phenylene group

U 2,6-difluoro-1,4-phenylene group

W 2,3-difluoro-1,4-phenylene group

B(O) 4,6-difluoro-dibenzo[b,d]furan-3,7-diyl group

B(S) 4,6-difluoro-dibenzo[b,d]thiophene-3,7-diyl group

C(5) cyclopentyl group

THF(2,5) Tetrahydrofuran-2,5-diyl group

THF tetrahydrofuran-2-group

DHF(1) 4,5-dihydrofuran-2-group

DHF(2) 2,5-dihydrofuran-2-group

DHF(2.5) 2,5-dihydrofuran-2,5-diyl group

THT tetrahydrothiophene-2-group

DHT(3) 2,3-dihydrothiophene-2-group

DHT(1) 4,5-dihydrothiophene-2-group -COO- E ester group -CH ₂ CH ₂ - 2 ethyl bridging group -CH ₂ CH ₂ CH ₂ - 3 profile bridge -O- O oxygen substituent -CH=CH- or -CH=CH ₂ V vinyl group -C _n H _2n+1 or -C _n H _2n - N (n represents a positive integer from 1 to 12) A straight-chain alkyl group or a straight-chain alkylene group

For example, a compound of the following structural formula:

, 상기 구조식을 표 1의 코드로 나타낼 경우, nCCGF로 나타낼 수 있으며, 코드에서 n은 좌측 알킬기의 C 원자 수를 나타내며, 예컨대 n이 “3”일 경우, 해당 알킬기는 -C₃H₇임을 나타내고; 코드에서 C는 시클로헥실기를 나타내며, G는 2-플루오로-1,4-페닐렌기를 나타내고, F는 불소를 나타낸다.

, When the structural formula is represented by the code of Table 1, it can be represented by nCCGF, where n in the code represents the number of C atoms in the left alkyl group, for example, when n is “3”, the corresponding alkyl group represents -C ₃ H ₇ ; In the code, C represents a cyclohexyl group, G represents a 2-fluoro-1,4-phenylene group, and F represents fluorine.

The abbreviations of the test items in the following examples are as follows:

Cp Clearing point (nematic-isotropic phase transformation temperature, °C)

Δn Optical anisotropy (589 nm, 25°C)

Δε Dielectric anisotropy (1KHz, 25℃)

ε_⊥ perpendicular permittivity

ε _⊥ /|Δε| Ratio of Perpendicular Permittivity and Absolute Permittivity

K _ave mean modulus of elasticity

t_-30℃ Cold storage time (h, -30℃)

T _r Transmittance (%)

here,

Cp: Obtained by testing with a melting point measuring device. Δn: Test at 25° C. and sodium lamp (589 nm) light source using an Abbe refractometer. Δε=ε _l -ε _⊥ , where ε _l is the dielectric constant parallel to the molecular axis, ε _⊥ is the dielectric constant perpendicular to the molecular axis, the test conditions are: 25°C, 1 KHz, and the test case is type VA (case thickness 6 μm).

(K₁₁ + K₂₂ + K₃₃)이다.K ₁₁ , K ₂₂ , K ₃₃ are values obtained by calculating the CV curve of the liquid crystal material using an LCR tester and a VA test case, and the test conditions are: 6μm VA test case, V = 0.1-20V; K _ave =

(K ₁₁ + K ₂₂ + K ₃₃ ).

t _-30°C : Put the nematic liquid crystal medium in a glass bottle, store at -30°C, and record the time at which crystal precipitation is observed.

T _r uses a DMS 505 photoelectric comprehensive tester to test the VT curve of the dimming device, and the maximum transmittance of the VT curve is taken as the transmittance of the liquid crystal. The test case is of VA type and the case thickness is 3.5 μm.

Each component used in the following examples can be synthesized through a known method or obtained through a commercial route. This synthesis technique is common, and it was confirmed that each obtained liquid crystal compound conformed to the standards of electronic compounds by testing.

The liquid crystal composition was prepared according to the mixing ratio of the liquid crystal composition defined in the following examples. The preparation of the liquid crystal composition is prepared according to a conventional method in the field, and is prepared by mixing according to a prescribed ratio in a method such as heating, ultrasonication, suspension, and the like.

Liquid crystal compositions provided in the following examples were prepared and studied. Hereinafter, test results of the composition and performance parameters of each liquid crystal composition are shown.

Comparative Example 1

The liquid crystal composition of Comparative Example 1 was prepared according to each of the compounds listed in Table 2 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 2] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 13 N-3 Cp 85 2CC1OWO2 2 N-6 Δn 0.106 3CC1OWO2 10 N-6 Δε -3.9 3CPWO4 6 N-11 _ε⊥ 5.9 3CCV 38 M-1 K _ave 12.8 VCCP1 8 M-12 T _r 13.2 3PPWO4 2 N-12 t _-30℃ <240 3PPWO2 2 N-12 ε _⊥ /|Δε| 1.51 3CPP2V 2 M-16 3CPP2V1 2 M-16 3CPWO2 6 N-11 5OWO3 3 N-1 THF2B(O)O3 3 ―― THF2B(O)O4 3 ―― Sum 100

Example 1

The liquid crystal composition of Example 1 was prepared according to each of the compounds listed in Table 3 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 3] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 13 N-3 Cp 85 2CC1OWO2 2 N-6 Δn 0.106 3CC1OWO2 10 N-6 Δε -4.3 3CPWO4 6 N-11 _ε⊥ 6.8 3CCV 38 M-1 K _ave 13.3 VCCP1 8 M-12 T _r 13.6 3PPWO4 2 N-12 t _-30℃ >300 3PPWO2 2 N-12 ε _⊥ /|Δε| 1.58 3CPP2V 2 M-16 3CPP2V1 2 M-16 3CPWO2 6 N-11 5OWO3 3 N-1 THF1OB(O)O3 3 I THF1OB(O)O4 3 I Sum 100

Comparative Example 2

The liquid crystal composition of Comparative Example 2 was prepared according to each of the compounds listed in Table 4 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 4] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 12 N-3 Cp 90 2CC1OWO2 2 N-6 Δn 0.107 3CC1OWO2 9 N-6 Δε -4 3PWP2 4 N-13 _ε⊥ 6.1 5PP1 2 M-6 K _ave 12.6 3CCV 35 M-1 T _r 13.4 2C1OWO2 2 N-3 t _-30℃ <240 3CCWO2 4 N-5 ε _⊥ /|Δε| 1.53 4CCWO3 4 N-5 3CWO2 5 N-2 3CPP2V 4 M-16 3CPP2V1 3 M-16 3CPWO2 6 N-11 C(5)1OB(O)O3 4 ―― C(5)1OB(O)O5 4 ―― Sum 100

Example 2

The liquid crystal composition of Example 2 was prepared according to each of the compounds listed in Table 5 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 5] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 12 N-3 Cp 90 2CC1OWO2 2 N-6 Δn 0.107 3CC1OWO2 9 N-6 Δε -4.2 3PWP2 4 N-13 _ε⊥ 6.7 5PP1 2 M-6 K _ave 13.3 3CCV 35 M-1 T _r 13.8 2C1OWO2 2 N-3 t _-30℃ >300 3CCWO2 4 N-5 ε _⊥ /|Δε| 1.59 4CCWO3 4 N-5 3CWO2 5 N-2 3CPP2V 4 M-16 3CPP2V1 3 M-16 3CPWO2 6 N-11 THF2OB(O)O3 4 I THF2OB(O)O4 4 I Sum 100

Comparative Example 3

The liquid crystal composition of Comparative Example 3 was prepared according to each of the compounds listed in Table 6 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 6] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 13 N-3 Cp 86 3CC1OWO2 13 N-6 Δn 0.105 VCCP1 9 M-12 Δε -4.1 3CCV 38 M-1 _ε⊥ 5.8 2C1OWO2 3 N-3 K _ave 12.4 3PPWO4 2 N-12 T _r 12.3 5PPWO2O2 2 N-12 t _-30℃ <240 4PPWO2O3 2 N-12 ε _⊥ /|Δε| 1.41 3CPP3 2 M-16 3CCP1 3 M-12 3CPWO2 10 N-11 2CPWO2 3 N-11 Sum 100

Example 3

The liquid crystal composition of Example 3 was prepared according to each of the compounds listed in Table 7 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 7] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 13 N-3 Cp 86 3CC1OWO2 13 N-6 Δn 0.105 VCCP1 9 M-12 Δε -4.3 3CCV 38 M-1 _ε⊥ 6.8 2C1OWO2 3 N-3 K _ave 13.4 3PPWO4 2 N-12 T _r 13.9 5PPWO2O2 2 N-12 t _-30℃ >300 4PPWO2O3 2 N-12 ε _⊥ /|Δε| 1.58 3CPP3 2 M-16 3CCP1 3 M-12 3CPWO2 4 N-11 2CPWO2 3 N-11 THF2OB(S)O3 3 I THF2OB(S)O4 3 I Sum 100

Example 4

The liquid crystal composition of Example 4 was prepared according to each of the compounds listed in Table 8 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 8] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3CCV 34 M-1 Cp 91 3CCV1 6 M-1 Δn 0.107 3CPP3 5 M-16 Δε -4.3 3CCP1 5 M-12 _ε⊥ 7.3 3PPWO4 3 N-12 K _ave 13.2 3CPWO2 6 N-11 T _r 13.8 2CPWO2 6 N-11 t _-30℃ >300 3PWO2 8 N-10 ε _⊥ /|Δε| 1.70 3C1OWO2 13 N-3 3CC1OWO2 8 N-6 THT2OB(S)O3 3 I DHT(3)2OB(S)O4 3 I Sum 100

Example 5

The liquid crystal composition of Example 5 was prepared according to each of the compounds listed in Table 9 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 9] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 8 N-3 Cp 87 2CC1OWO2 10 N-6 Δn 0.105 3CC1OWO2 10 N-6 Δε -4.2 3PWP2 8 N-13 _ε⊥ 7.2 3PPWO4 3 N-12 K _ave 13.3 3PPWO2 3 N-12 T _r 14.2 5PP1 8 M-6 t _-30℃ >300 3CCV 32 M-1 ε _⊥ /|Δε| 1.71 3CPP2V 6 M-16 3CPP2V1 6 M-16 DHF(1)2OB(O)O3 3 I DHT(1)2OB(O)O3 3 I Sum 100

Example 6

The liquid crystal composition of Example 6 was prepared according to each of the compounds listed in Table 10 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 10] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3CWO2 8 N-2 Cp 90 2CCWO2 7 N-5 Δn 0.107 3CCWO2 11 N-5 Δε -4.3 3CPWO2 7 N-11 _ε⊥ 6.9 3CPWO4 7 N-11 K _ave 13.2 3PWO2 8 N-10 T _r 13.8 3CPP2 6 M-16 t _-30℃ >300 VCPP1 8 M-16 ε _⊥ /|Δε| 1.60 V2CCP1 8 M-12 2THF(2,5)2OB(O)O3 5 I THF2OB(O)O4 5 I 3CC2 15 M-1 4CC3 5 M-1 Sum 100

Example 7

The liquid crystal composition of Example 7 was prepared according to the respective compounds listed in Table 11 and their weight %, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 11] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 12 N-3 Cp 91 3CC1OWO2 9 N-6 Δn 0.108 3CCWO2 10 N-5 Δε -4.2 3CPWO2 6 N-11 _ε⊥ 7.2 3CPWO4 6 N-11 K _ave 13.3 3PWO2 10 N-10 T _r 14.2 3CPP2 6 M-16 t _-30℃ >300 VCPP1 6 M-16 ε _⊥ /|Δε| 1.71 3CPO2 5 M-2 DHF(2)3OB(O)O3 5 I 2DHF(2,5)2OB(O)O4 5 I 3CCV 15 M-1 5PP1 5 M-6 Sum 100

Example 8

The liquid crystal composition of Example 8 was prepared according to the respective compounds listed in Table 12 and their weight%, and the liquid crystal composition was filled between two substrates of a liquid crystal display device to test performance.

[Table 12] Preparation of liquid crystal compositions and test results of performance parameters Ingredient code weight(%) rescue code Performance parameter test results 3C1OWO2 10 N-3 Cp 87 3CC1OWO2 8 N-6 Δn 0.109 3CCWO2 10 N-5 Δε -4.2 3CPWO2 6 N-11 _ε⊥ 7.3 3PPWO3O4 3 N-12 K _ave 13.5 5PPWO4O5 3 N-12 T _r 14.3 3PGW2 5 N-17 t _-30℃ >300 3PWP4 5 N-13 ε _⊥ /|Δε| 1.74 3CPP2 6 M-16 VCPP1 6 M-16 3CPO2 5 M-2 THF2OB(S)O4 3 I THF3OB(S)O3 3 I THF2OB(O)O4 3 I 3CC2 18 M-1 5PP1 6 M-6 Sum 100

, Z와 같은 라디칼을 최적화하여 상기 효과를 구현함을 알 수 있으며, 이들 중 임의의 하나를 변경하더라도 효과는 열화된다.Comparing Example 1 and Comparative Example 1, compared to the case where a conventional straight-chain alkyl group is applied as a compound of a linking radical (Comparative Example 1), a compound of formula I containing an alkyleneoxy group or an alkylenethio group linking radical When applied to a liquid crystal composition, the absolute value of dielectric anisotropy, perpendicular permittivity, ratio of normal permittivity to absolute permittivity, K _ave value, transmittance and low temperature storage time of the liquid crystal composition can be improved while maintaining appropriate clearing point and appropriate optical anisotropy. Comparing Example 2 with Comparative Example 2, when compared with the prior art 5-membered ring structure containing carbon atoms (Comparative Example 2), a 5-membered heterocycle containing an oxygen atom or a sulfur atom containing The compound of the general formula I of the present application (Example 2) including a 5-membered heterocyclic structure maintains an appropriate clearing point and an appropriate optical anisotropy, while maintaining the absolute value of the dielectric anisotropy, the perpendicular permittivity, the perpendicular permittivity and the absolute permittivity of the liquid crystal composition. Ratio, K _ave value, permeability and cold storage time can be improved. From the above comparative results, the present application provides the compound of formula I

It can be seen that the above effect is implemented by optimizing the radicals such as , Z, and even if any one of them is changed, the effect is deteriorated.

Comparing Example 3 and Comparative Example 3, when the compound of Formula I is introduced into the liquid crystal composition (Example 3) compared to the case where the compound of Formula I is not introduced into the liquid crystal composition (Comparative Example 3), the appropriate clearing point and Absolute value of dielectric anisotropy, perpendicular permittivity, ratio of normal permittivity to absolute permittivity, K _ave value, transmittance, and low temperature storage time of the liquid crystal composition may be improved while maintaining proper optical anisotropy.

In summary of the above, the liquid crystal composition of the present application has a relatively large absolute value of dielectric anisotropy, a relatively large perpendicular permittivity, a relatively large ratio of normal permittivity to absolute permittivity, and a relatively large Kave value while maintaining an appropriate clearing point and appropriate optical anisotropy. , relatively good transmittance and relatively long low temperature storage time, so that the liquid crystal display including the same has a relatively low threshold voltage, relatively good contrast, relatively short response time, relatively good transmittance and relatively good low temperature stability, IPS mode , has high application value in liquid crystal displays in FFS mode and VA mode.

The above embodiments are intended to explain the technical spirit and features of the present application, and are intended to help those skilled in the art to understand and implement the contents of the present application, and are not intended to limit the scope of the present invention.

Claims (10)

In the liquid crystal composition containing the dibenzo derivative,
at least one compound of formula I;

I; and
comprising at least one compound of the general formula N,

N,
here,
R ₁ is -H, halogen, a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, the linear or branched alkyl group containing 1 to 12 carbon atoms,

,

or

-CH ₌ CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO -, and one or more -H of the aforementioned radicals may each independently be substituted by -F or -Cl;
R _x represents -H, a straight-chain or branched alkyl group containing 1 to 12 carbon atoms, and one of the straight-chain or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - may each independently be replaced by -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO-, one or two Each of the above -H may be independently substituted with -F or -Cl, wherein R _x is a ring

connected to any carbon atom in;
R _N1 and R _N2 are each independently a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, one of the linear or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO-;
ring

and rings

are each independently

,

,

or

represents, where,

,

and

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

and

one or more -H of may be substituted by -F, -Cl, -CN, -CH ₃ or -OCH ₃ , and -CH= of one or more rings may be replaced by -N=;
ring

Is

, wherein X ₂ represents -O- or -S-, and single bonds may be replaced by double bonds in one or more rings of the aforementioned radicals;
ring

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

one or more -H of may be substituted by -F, -Cl or -CN, and -CH= of one or more rings may be replaced by -N=;
X ₁ is -O-. represents -S-, -CO-, -CF ₂ -, -NH- or -NF-;
Y ₁ and Y ₂ each independently represent -H, halogen, a halogenated alkyl group or non-halogenated alkyl group containing 1 to 3 carbon atoms, a halogenated alkoxy group or non-halogenated alkoxy group containing 1 to 3 carbon atoms. ;
Z represents -(CH ₂ ) _a O- or -(CH ₂ ) _a S-, where a represents an integer from 0 to 7;
Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -CH=CH-, - C≡C-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -(CH ₂ ) ₄ -, -CF ₂ O- or -OCF ₂ -;
Z _N1 and Z _N2 are each independently a single bond, -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -(CH ₂ ) ₄ -, -CF ₂ O- or -OCF ₂ -;
L _N1 and L _N2 each independently represent -H, an alkyl group containing 1 to 3 carbon atoms, or halogen;
n ₁ and n ₂ each independently represent 0, 1 or 2, and when n ₁ =2, a ring

are the same or different, Z ₁ is the same or different, and when n ₂ =2, a ring

are the same or different, Z ₂ are the same or different, and
n _N1 represents 0, 1, 2 or 3, n _N2 represents 0 or 1, and 0 ≤ n _N1 + n _N2 ≤ 3, when n _N1 =2 or 3, a ring

are the same or different, and Z _N1 are the same or different liquid crystal composition.
The liquid crystal composition according to claim 1, wherein X ₁ represents -O-, -S- or -CO-, and Y ₁ and Y ₂ both represent -F.
The liquid crystal composition according to claim 1 or 2, wherein n ₁ represents 0 and n ₂ represents 0 or 1.
The liquid crystal composition according to any one of claims 1 to 3, wherein the compound of formula I accounts for 0.1% to 40% by weight of the liquid crystal composition.
The liquid crystal composition according to any one of claims 1 to 4, wherein the liquid crystal composition includes two or more compounds of Formula I.
The liquid crystal composition according to any one of claims 1 to 5, wherein the liquid crystal composition comprises at least one compound of formula I in which X ₂ is -O- and/or one compound of formula I in which X ₂ is -S-. includes; Optionally, the liquid crystal composition includes two or more compounds of the general formula I, wherein X ₂ is -O-.
The liquid crystal composition according to any one of claims 1 to 6, wherein the compound of formula N is selected from any one or a combination of two or more of the following compounds.

N-1;

N-2;

N-3;

N-4;

N-5;

N-6;

N-7;

N-8;

N-9;

N-10;

N-11;

N-12;

N-13;

N-14;

N-15;

N-16;

N-17;

N-18;

N-19;

N-20;

N-21; and

N-22;
Optionally, the compound of formula N comprises 0.1% to 60% by weight of the liquid crystal composition;
Optionally, the compound of formula N is of formula N-1, formula N-2, formula N-3, formula N-4, formula N-5, formula N-6, formula N-8 , general formula N-9, general formula N-10, general formula N-11, general formula N-12, general formula N-13, general formula N-17, general formula N-18, general formula N-19 and general formula any one or combination of two or more of the compounds of Formula N-21;
Optionally, the compound of formula N comprises one or more of the compounds of formula N-3 and/or formula N-6;
Optionally, the compound of formula N comprises one or more of the compounds of formula N-12, formula N-13, formula N-17;
Optionally, the compound of formula N is one or more of the compounds of formula N-3 and/or N-6, and one or more of the compounds of formula N-12 and/or N-13. includes;
Optionally, the compound of formula N includes at least one compound of formula N-10 and/or formula N-11.
8. The ring according to any one of claims 1 to 7

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, wherein

one or more -H of may be substituted by -F, -Cl or -CN, and -CH= of one or more rings may be replaced by -N=;
Optionally, Z _N1 and Z _N2 are each independently a single bond, -CH ₂ O-, -OCH ₂ -, -CH=CH-, -CH ₂ CH ₂ -, -CF ₂ CF ₂ -, -CF ₂ O represents - or -OCF ₂ -;
Optionally, 0<n _N1 +n _N2 ≤3;
Optionally, when n _N1 =1 and n _N2 =0, a ring

is not an aromatic ring; also
n _N1 =2 and a ring

go

When representing, R _N1 is not an alkenyl group liquid crystal composition.
9. The liquid crystal composition according to any one of claims 1 to 8, comprising at least one compound of formula M:

M,
here,
R _M1 and R _M2 are each independently a straight-chain or branched alkyl group containing 1 to 12 carbon atoms;

,

or

Representing, one of the linear or branched alkyl groups containing 1 to 12 carbon atoms or two or more non-adjacent -CH ₂ - are each independently -CH=CH-, -C≡C-, -O- , -CO-, -CO-O- or -O-CO-;
ring

, ring

and rings

are each independently

or

represents, where,

One or more of -CH ₂ - may be replaced with -O-, and single bonds in one or more rings may be replaced with double bonds, wherein:

one or more -H of may be replaced by halogen;
Z _M1 and Z _M2 are each independently a single bond -CO-O-, -O-CO-, -CH ₂ O-, -OCH ₂ -, -C≡C-, -CH=CH-, -CH ₂ CH ₂ - or (CH ₂ ) ₄ -; also
n _M represents 0, 1 or 2, when n _M =2, a ring

are the same or different, Z _M2 are the same or different;
Optionally, the compound of formula M is selected from any one or combination of two or more of the following compounds:

M-1;

M-2;

M-3;

M-4;

M-5;

M-6;

M-7;

M-8;

M-9;

M-10;

M-11;

M-12;

M-13;

M-14;

M-15;

M-16;

M-17;

M-18;

M-19;

M-20;

M-21;

M-22;

M-23;

M-24;

M-25;

M-26;

M-27;

M-28;

M-29; and

M-30,
Optionally, the compound of formula M comprises from 0.1% to 80% by weight of the liquid crystal composition.
A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 9.