JPH02183231A - Material for organic nonlinear optical element and organic nonlinear optical thin-film formed by using this material - Google Patents
Material for organic nonlinear optical element and organic nonlinear optical thin-film formed by using this materialInfo
- Publication number
- JPH02183231A JPH02183231A JP261089A JP261089A JPH02183231A JP H02183231 A JPH02183231 A JP H02183231A JP 261089 A JP261089 A JP 261089A JP 261089 A JP261089 A JP 261089A JP H02183231 A JPH02183231 A JP H02183231A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- group
- optically active
- nonlinear optical
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 title claims abstract description 22
- 239000010409 thin film Substances 0.000 title description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 4
- 239000002775 capsule Substances 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000005684 electric field Effects 0.000 description 6
- 210000002858 crystal cell Anatomy 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- AXZJHDNQDSVIDR-NSHDSACASA-N 4178-93-2 Chemical compound CC(C)C[C@H](N)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 AXZJHDNQDSVIDR-NSHDSACASA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- -1 merocyanine Chemical class 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- NPZDNLCYFLDJFA-UHFFFAOYSA-N n,n-dimethyl-2-nitroaniline Chemical compound CN(C)C1=CC=CC=C1[N+]([O-])=O NPZDNLCYFLDJFA-UHFFFAOYSA-N 0.000 description 1
- HHHDEYQZODHHKT-UHFFFAOYSA-N n-(2-amino-5-nitrophenyl)acetamide Chemical class CC(=O)NC1=CC([N+]([O-])=O)=CC=C1N HHHDEYQZODHHKT-UHFFFAOYSA-N 0.000 description 1
- FZZMDWLROBNSRG-UHFFFAOYSA-N n-phenyliminonitramide Chemical compound [O-][N+](=O)N=NC1=CC=CC=C1 FZZMDWLROBNSRG-UHFFFAOYSA-N 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は有機非線形光学素子用材料およびこれを用いて
作製した有機非線形光学薄膜に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a material for organic nonlinear optical elements and an organic nonlinear optical thin film produced using the same.
（従来の技術および問題点）
オプトエレクトロニクスの分野では二次の有機非線形光
学材料の開発が盛んに行なわれている。(Prior Art and Problems) In the field of optoelectronics, second-order organic nonlinear optical materials are being actively developed.
これらの材料のうち、例えば、長鎖系のニトロアゾベン
ゼンのようにバルクの結晶状態で中心対称性を有する化
合物は二次の光非線形性（ＳｅｃｏｎｄＨａｒｍｏｎｉ
ｃ Ｇｅｎｅｒａｔｉｏｎ、 、ＳＨＧ ）を示さない
が、配向によって対称構造を崩すことにより光非線形性
を示すようになること（文献例： Ｏ，Ａ、Ａｋｔｓｉ
ｐｅｔｒｏｖ、 Ｎ、Ｎ、Ａｋｈｍｅｄｉｅｖ、 Ｅ、
Ｄ、Ｍｉｓｈｉｎａ、 Ｖ、Ｒ，Ｎｏｖａｋ、 ＪＥＴ
Ｐ Ｌｅｔｔ、、 ３７，２０７−２０９（１９８３）
）が知られている。Among these materials, compounds that have central symmetry in the bulk crystalline state, such as long-chain nitroazobenzene, exhibit second-order optical nonlinearity (Second Harmoni).
c Generation, , SHG ), but by breaking the symmetric structure due to orientation, optical nonlinearity is exhibited (Literature example: O, A, Aktsi
petrov, N.N., Akhmediev, E.
D, Mishina, V, R, Novak, JET
P Lett, 37, 207-209 (1983)
)It has been known.
また、分子配向の秩序度が高いほど３８０強度が大きく
なることも知られている。すなわち、配向薄膜とするこ
とで非線形性の発現が期待できるばかりでなく、より大
きな３８０強度を得ることも可能となる。また、配向薄
膜では分子の不規則性に起因する透過光の散乱を小さく
できるため非線形光導波路とした場合の光損失を低減で
きるという特徴もある。このため、実用的な非線形光学
材料の実現に向けて、高配向薄膜が形成可能な材料の開
発が重要な課題となってきている。従来、光非線形性と
配向性の双方に優れる材料を得るため、すてに配向性に
優れることが知られている液晶材料の光非線形性が検討
されてきた。中でも、分子内にカイラル置換基を有する
強誘電性液晶およびその類似化合物は、中心対称性がな
いため非線形光学材料への展開が期待されている（文献
例：Ｎ。It is also known that the higher the order of molecular orientation, the higher the 380 strength. That is, by forming an oriented thin film, not only can the expression of nonlinearity be expected, but also it is possible to obtain a larger 380 intensity. In addition, since the oriented thin film can reduce the scattering of transmitted light due to molecular irregularity, it also has the characteristic that it can reduce optical loss when used as a nonlinear optical waveguide. Therefore, in order to realize practical nonlinear optical materials, the development of materials that can form highly oriented thin films has become an important issue. Conventionally, in order to obtain materials that are excellent in both optical nonlinearity and orientation, the optical nonlinearity of liquid crystal materials, which are known to have excellent orientation, has been studied. Among them, ferroelectric liquid crystals and their similar compounds that have chiral substituents in their molecules are expected to be developed into nonlinear optical materials because they lack central symmetry (Reference example: N.
Ｍ、５ｈｔｙｋｏｖ、 Ｍ−Ｉ−Ｂａｒｎｉｋ、 Ｌ、
ＡＢｅｒｅｓｎｅｖ、 Ｌ、Ｍ、Ｂ１１ｎｏｖ、 Ｍｏ
１．Ｃｒｙｓｔ、Ｌｉｑ、Ｃｒｙｓｔ、、 １２４．３
７９−３９０（１９８５）） 、これまでに報告されて
いる光非線形性を示す強誘電性液晶材料の主な例を第１
表に示す。しかし、第１表の液晶化合物は粉末法により
測定した結晶状態での光非線形性が測定限界以下であり
（第２表、ＩＡ、ＩＢ）、液晶セル中で電場を印加して
配向させた状態でもカ２′が１０−”ｅｓｕ程度の小さ
な光非線形しか示さず、実用素子作製に供せるものでは
なかった。M, 5htykov, M-I-Barnik, L,
ABeresnev, L, M, B11nov, Mo
1. Cryst, Liq, Cryst,, 124.3
79-390 (1985)), the main examples of ferroelectric liquid crystal materials exhibiting optical nonlinearity that have been reported so far are listed in the first section.
Shown in the table. However, the optical nonlinearity of the liquid crystal compounds shown in Table 1 in the crystal state measured by the powder method is below the measurement limit (Table 2, IA, IB), and the state of alignment by applying an electric field in the liquid crystal cell However, it exhibited only a small optical nonlinearity of about 10-''esu, and could not be used for producing practical devices.
第１表
第２表
（問題点を解決するための手段）
本発明者らは、光非線形と配向性の双方に優れる素子用
材料を見いだすため、液晶性を示す非線形光学材料につ
いての探索を行なった結果、本発明に到達した。Table 1 Table 2 (Means for solving problems) In order to find a material for an element that is excellent in both optical nonlinearity and orientation, the present inventors conducted a search for nonlinear optical materials that exhibit liquid crystallinity. As a result, we have arrived at the present invention.
本発明は、下記一般式（Ｉ）、（ＩＩ）、（ＩＩＩ）お
よび（ｒＶ）
（式中、Ｒはアルキル基またはフッ素を含むアルキル基
、Ｒ′″は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ、Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲＣＯＮＨ基（Ｒ。The present invention relates to the following general formulas (I), (II), (III) and (rV) (wherein, R is an alkyl group or an alkyl group containing fluorine, and R''' is an optically active alkyl group or an ether bond). or an optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or RCONH group (R
はアルキル基）、ｊ、に、ｌは０または１）で示される
化合物を単独で、もしくは他の化合物と混合して用いる
ことを特徴とする有機非線形光学素子用材料およびこれ
らを使用して作製した有機非線形光学薄膜である。is an alkyl group), j, and l is 0 or 1), used alone or in combination with other compounds, and materials for organic nonlinear optical elements, and fabricated using the same. This is an organic nonlinear optical thin film.
本発明の一般式（Ｉ）〜（ＩＶ）で示した、液晶性を示
す非線形光学素子用材料としては、例えば、下記の構造
の化合物を具体例としてあげることができる。Specific examples of the materials for nonlinear optical elements exhibiting liquid crystallinity represented by general formulas (I) to (IV) of the present invention include compounds having the following structures.
（以下余白）
ｎ＝７．８，９，１０，１２． ｐ＝ｏ山２，３，４，
５． ｍ−２，３，６ｎ−１０，ｐ−０，でｍ−２のと
き化合物ＩＣｎ＝７．８，９，１０．１２． ｐ＝ｏ、
Ｉ 、２，３，４，５． ｍ−２，３，６ｎ−７，８，
９，１０，Ｉ２． ｐ＝ｏ、１，２，３，４，５． ｍ
−２，３，６ｎ−８，ｐ−０，ｍ−２のとき化合物ＩＤ
ｎ＝７．８，９，１０，１２． ｐ＝ｏ山２，３，４，
５． ｍｍ２，３．６ｎ＝７．８，９，１０，１２．
ｐ−０山２，３，４，５． ｍ−１，２，３，６ｎ＝７
．８，９，１０．）２． ｐ−０，１，２，３，４，５
，ｍ−２，３，６ｎ＝７．８，９．ｔｏ、１２． ｐ−
０，１，２，３，４，５，ｍ＝２．３．６ｎ＝７．８，
９，１０，１２． ｐ−０，１，２，３，４，５，ｍ−
２，３，６ｎ＝７．８，９，１０，１２． ｐ＝ｏ、Ｉ
、２，３，４，５． ｍ＝２．３．６ｎ＝７．８，９，
１０，１２．ｐ−０，１，２，３，４，５，ｍ−１，２
，３，６ｎｍ７，８，９，１０，１２． ｐｍＯ，１，
２，３，４，５，ｍ−２，３，６ｎｗ７，８，９，１０
，１２． ｐ＝０山２，３，４，５． ｍ−２，３，６
ｎ−７，Ｉｌ！、９ＪＯ，１２，ｐ−０，１，２，３，
４，５，ｍ＝２．３．６ｎｍ４，５，６，７，８，９，
１１． ｐ−０，１，２，３，４，５，ｍ−２，３，６
ｎ−７，８，９，１０，１２，ｐ−０，１，２，３，４
，５，ｍ＝１．２，３．６ｎ＝７．８，９．ＩＱ、！２
． ｐ＝ｏ山２，３，４，５． ｍ−１，２，３，６ｎ
＝７．８，９４０，１２． ｐ−０，１，２，３，４，
５，ｍｍ２，３．６ｎ＝７．８，９，１０，１２．ｐ＝
ｏ山２，３，４，５．ｍ−λ３．６ｎ＝７．８，９，１
０，１２． ｐｍｏ、１，２，３，４，５． ｍ−２，
３，６物ＩＦ
Ｈ
ｎ＝７．８，９，１０，１２． ｐ＝ｏ山２，３，４，
５． ｍ−２，３，６ｎ＝７．８，９，１０，１２．
ｐ−０，１，２，３，４，５，ｍ−２，３，６ｎ”フ、
８，９，１０，１２．ｐ−０，１，２，３，４，５，ｍ
−２，３，６ｎ＝７．８，９，１０，１２． ｐ−０，
１，２，３，４，５，ｍ＝２．３．６ｎｍ７，８，９，
１０，１２． ｐ＝０．１，２，３，４，５． ｍ＝２
．３．６ｎ＝７．８，９，１０．＋２． ｐ＝ｏ山２，
３，４，５． ｍ−２，３，６ｎ＝７．８，９．）０，
１２． ｐ＝ｏ、１２，３，４，５． ｍ−２，３，６
ｎ＝７．８，９，１０，１２． ｐ＝ｏ、Ｉ、２，３，
４，５． ｍ＝２．３．６ｎ＝７．８，９，１０，１２
． ｐ＝ｏ山２，３，４，５． ｍ＝２．３．６ただし
ｎ−１２，ｐ＝１．ｍ−２は化合物１０ｎ＝７．８，９
，１０．＋２． ｐ−０，１，２，３，４，５，ｍ−２
，３，６ｎ−７，８，９，ＩＱ、１２．ｐ＝ｏｊ、２，
３，４，５．ｍ−２，３，６ｎ＝７．８，９，１０，１
２． ｐ＝ｏ山２，３，４，５． ｍ＝２．３．６ｎ−
７，８，９，１０，１２，ｐ＝０．！、２，３，４，５
． ｍ＝２．３．６ｎ＝７．８，９． ＋０．１２．
ｐ＝０山２，３，４，５． ｍ−２，３，６ｎ＝６．７
，８，９．１１． ｐ−０山２，３，４，５． ｍ−２
，３，６ｎ−７，８，９，１０，１２，ｐ＝ｏ山２，３
，４，５． ｍ−１，２，３，６ｎ＝７．８，９４０．
＋２． ｐ＝ｏ、ｌ、２，３，４，５． ｍ＝２．３．
６ｎ＝７．８，９，１０，１２． ｐ−０ＩＩ、２，３
，４，５． ｍ−１，２，３，６ｎ＝７．８，９，１０
，１２． ｐ−０，１，２，３，４，５，ｍｍ２，３．
６ＣＨ３ＣＯＮＨ
ｎ−７，８，９，１０，１２，ｐ＝０．１，２，３，４
，５． ｍ−２，３，６ｎ＝７．８，９，１０，１２．
ｐ＝０．！、２，３，４，５． ｍ−２，３，６ｎ−
７，８，９，１０，＋２． ｐ＝０山２，３，４，５．
ｍ−２，３，６ｎ＝７．８，９，１０，１２． ｐ＝
０山２，３，４，５． ｍ−２，３，６ｎ＝７．８，９
，１０，１２． ｐ＝０．！、２，３，４，５． ｍ＝
２．３．６ｎｘ７，８，９，１０，１２． ｐｘＯ，１
，２，３，４，５，ｍ−２，３，６ただしｎ−８，ｐ−
１，ｍ−２は化合物ＩＨｎｘ６，７，８，９４１． ｐ
−０，１，２，３，４，５，ｍ−２，３，６ｎｍ７．Ｉ
ｌｌ、９，１０．＋２． ｐｍｏ、！、２，３，４，５
． ｍ−１，２，３，６ｎ＝７．８，９，１０，１２．
ｐ＝０．Ｉ、２，３，４，５． ｍ＝１．２，３．６
ｎ＝７．８，９，１０，１２． ｐ−０，１，２，３，
４，５，ｍ＝２．３．６Ｈ２
ｎ＝７．８，９，１０，１２． ｐ＝０．１，２，３，
４，５． ｍ＝２．３．６ｐ＝７．８，９，１０．１２
． ｐ−０，１，２，３，４，５，ｍ−２，３，６ｎ＝
７Ｊ、９，１０，１２． ｐ−０，１，２，３，４，５
，ｍ−２，３，６ｎ＝７．８，９，１０，１２． ｐｍ
ｏ、１，２，３，４，５． ｍ−２，３，６ｎ＝７．８
，９，１０，１２． ｐ−０，１，２，３，４，５，ｍ
−２，３，６ｎ＝７．８，９．ｔＯ，１２，ｐ＝０．１
，２，３，４，５． ｍ４，３．６ｒ
ｎ−６，７，８，９，１１，ｐ−０，１，２，３，４，
５，ｒｎ＝２．３．６ｎ＝７．８，９，１０，１２．
ｐｍｏ、１，２，３，４，５． ｒｎ−２，３，６ｎ＝
７．８，９，１０，１２． ｐ＝ｏ山２，３，４，５．
ｍ−２，３，６ｎ＝７．８，９，１０，１２． ｐ−
Ｏｊ、２，３，４，５． ｍ−２，３，６なお、本発明
の一般式（Ｉ）〜（ＩＶ）式で示される、液晶性を示す
非線形光学素子用材料の光学活性置換基はＲ一体、Ｓ一
体のどちらでもよいことは言うまでもない。(Left below) n=7.8, 9, 10, 12. p=o mountain 2, 3, 4,
5. m-2,3,6n-10,p-0, and when m-2, compound ICn=7.8,9,10.12. p=o,
I, 2, 3, 4, 5. m-2,3,6n-7,8,
9,10,I2. p=o, 1, 2, 3, 4, 5. m
Compound ID when -2,3,6n-8,p-0,m-2
n=7.8, 9, 10, 12. p=o mountain 2, 3, 4,
5. mm2, 3.6n=7.8, 9, 10, 12.
p-0 mountain 2, 3, 4, 5. m-1, 2, 3, 6n=7
．． 8,9,10. )2. p-0, 1, 2, 3, 4, 5
, m-2,3,6n=7.8,9. to, 12. p-
0,1,2,3,4,5,m=2.3.6n=7.8,
9, 10, 12. p-0,1,2,3,4,5,m-
2, 3, 6n=7.8, 9, 10, 12. p=o,I
, 2, 3, 4, 5. m=2.3.6n=7.8,9,
10,12. p-0,1,2,3,4,5,m-1,2
,3,6nm7,8,9,10,12. pmO,1,
2,3,4,5,m-2,3,6nw7,8,9,10
,12. p=0 mountain 2, 3, 4, 5. m-2, 3, 6
n-7, Il! ,9JO,12,p-0,1,2,3,
4,5,m=2.3.6nm4,5,6,7,8,9,
11. p-0,1,2,3,4,5,m-2,3,6
n-7, 8, 9, 10, 12, p-0, 1, 2, 3, 4
,5,m=1.2,3.6n=7.8,9. IQ! 2
．． p=o mountain 2, 3, 4, 5. m-1, 2, 3, 6n
=7.8,940,12. p-0, 1, 2, 3, 4,
5, mm2, 3.6n=7.8, 9, 10, 12. p=
O mountain 2, 3, 4, 5. m-λ3.6n=7.8,9,1
0,12. pmo, 1, 2, 3, 4, 5. m-2,
3,6 IF H n=7.8,9,10,12. p=o mountain 2, 3, 4,
5. m-2, 3, 6n=7.8, 9, 10, 12.
p-0,1,2,3,4,5,m-2,3,6n'',
8, 9, 10, 12. p-0,1,2,3,4,5,m
-2,3,6n=7.8,9,10,12. p-0,
1,2,3,4,5,m=2.3.6nm7,8,9,
10,12. p=0.1, 2, 3, 4, 5. m=2
．． 3.6n=7.8,9,10. +2. p=o mountain 2,
3, 4, 5. m-2,3,6n=7.8,9. )0,
12. p=o, 12, 3, 4, 5. m-2, 3, 6
n=7.8, 9, 10, 12. p=o, I, 2, 3,
4,5. m=2.3.6n=7.8,9,10,12
．． p=o mountain 2, 3, 4, 5. m=2.3.6, but n-12, p=1. m-2 is the compound 10n=7.8,9
,10. +2. p-0,1,2,3,4,5,m-2
,3,6n-7,8,9,IQ,12. p=oj, 2,
3, 4, 5. m-2,3,6n=7.8,9,10,1
2. p=o mountain 2, 3, 4, 5. m=2.3.6n-
7, 8, 9, 10, 12, p=0. ! , 2, 3, 4, 5
．． m=2.3.6n=7.8,9. +0.12.
p=0 mountain 2, 3, 4, 5. m-2,3,6n=6.7
, 8, 9.11. p-0 mountain 2, 3, 4, 5. m-2
, 3, 6n-7, 8, 9, 10, 12, p=o mountain 2, 3
,4,5. m-1,2,3,6n=7.8,940.
+2. p=o, l, 2, 3, 4, 5. m=2.3.
6n=7.8, 9, 10, 12. p-0II, 2,3
,4,5. m-1, 2, 3, 6n=7.8, 9, 10
,12. p-0, 1, 2, 3, 4, 5, mm2, 3.
6CH3CONH n-7,8,9,10,12,p=0.1,2,3,4
,5. m-2, 3, 6n=7.8, 9, 10, 12.
p=0. ! , 2, 3, 4, 5. m-2,3,6n-
7, 8, 9, 10, +2. p=0 mountain 2, 3, 4, 5.
m-2, 3, 6n=7.8, 9, 10, 12. p=
0 mountain 2, 3, 4, 5. m-2,3,6n=7.8,9
, 10, 12. p=0. ! , 2, 3, 4, 5. m=
2.3.6nx7,8,9,10,12. pxO,1
, 2, 3, 4, 5, m-2, 3, 6 but n-8, p-
1,m-2 is the compound IHnx6,7,8,941. p
-0,1,2,3,4,5,m-2,3,6nm7. I
ll, 9, 10. +2. pmo,! , 2, 3, 4, 5
．． m-1, 2, 3, 6n=7.8, 9, 10, 12.
p=0. I, 2, 3, 4, 5. m=1.2, 3.6
n=7.8, 9, 10, 12. p-0,1,2,3,
4,5,m=2.3.6H2 n=7.8,9,10,12. p=0.1, 2, 3,
4,5. m=2.3.6p=7.8,9,10.12
．． p-0,1,2,3,4,5,m-2,3,6n=
7J, 9, 10, 12. p-0, 1, 2, 3, 4, 5
, m-2, 3, 6n=7.8, 9, 10, 12. pm
o, 1, 2, 3, 4, 5. m-2,3,6n=7.8
,9,10,12. p-0,1,2,3,4,5,m
-2,3,6n=7.8,9. tO,12,p=0.1
, 2, 3, 4, 5. m4, 3.6r n-6, 7, 8, 9, 11, p-0, 1, 2, 3, 4,
5,rn=2.3.6n=7.8,9,10,12.
pmo, 1, 2, 3, 4, 5. rn-2,3,6n=
7.8, 9, 10, 12. p=o mountain 2, 3, 4, 5.
m-2, 3, 6n=7.8, 9, 10, 12. p-
Oj, 2, 3, 4, 5. m-2,3,6 Note that the optically active substituent of the material for nonlinear optical elements exhibiting liquid crystallinity, represented by the general formulas (I) to (IV) of the present invention, may be either R-integrated or S-integrated. Needless to say.
（作用）
本発明の（１）〜（ＩＶ）式で示される化合物は液晶と
なる温度範囲を有するため（具体例：第２表）、従来液
晶セルに用いられてきたポリイミドラビング基板などの
上に配向薄膜を作製することが容易であり、化合物の誘
電異方性、自発分極を利用して電場配向させることも容
易である。また、従来検討された強誘電性液晶化合物に
比べて非常に大きなＳＨＧ相対強度を示すことから、本
発明の液晶性を有する非線形光学材料を蒸着や二枚の基
板′間への注入などの方法で薄膜とすることにより、容
易に配向性に優れる非線形光学薄膜を得ることができる
。(Function) Since the compounds represented by formulas (1) to (IV) of the present invention have a temperature range in which they become liquid crystals (specific examples: Table 2), they can be It is easy to produce an oriented thin film, and it is also easy to align the compound in an electric field using the dielectric anisotropy and spontaneous polarization of the compound. In addition, since it exhibits a much larger SHG relative strength than conventionally studied ferroelectric liquid crystal compounds, the nonlinear optical material having liquid crystal properties of the present invention can be applied by methods such as vapor deposition or injection between two substrates. By forming a thin film using this method, a nonlinear optical thin film with excellent orientation can be easily obtained.
本発明の化合物と混合して使用する化合物は必ずしも光
非線形性を示す必要はないが、大きな光非線形性を示す
化合物を混合することによりさらに光非線形性の向上が
期待できる。一般に、大きな光非線形性を示す化合物は
配向薄膜を得ることが困難であるが、本発明の化合物と
混合することにより配向性も向上寄せることができる。Although the compound used in combination with the compound of the present invention does not necessarily have to exhibit optical nonlinearity, further improvement in optical nonlinearity can be expected by mixing a compound that exhibits large optical nonlinearity. Generally, it is difficult to obtain an oriented thin film with a compound exhibiting large optical nonlinearity, but by mixing it with the compound of the present invention, the orientation can be improved.
このような目的で混合する化合物には、例えば、２−メ
チル−４−ニトロアニリン、２−アセチルアミノ−４−
ニトロジメチルアニリン等のニトロアニリン誘導体、Ｎ
、Ｎ ’−ジメチル尿素などの尿素誘導体、メチル−（
２，４−ジニトロフェニル）−アミノプロパネート、ロ
イシン−ｐ−ニトロアニリドなどのアミノ酸誘導体、４
−ジメチルアミノ−４−スチルベンなどのスチルベン誘
導体、メロシアニンなどの複素環化合物とその分子塩な
どが挙げられる。Compounds mixed for this purpose include, for example, 2-methyl-4-nitroaniline, 2-acetylamino-4-
Nitroaniline derivatives such as nitrodimethylaniline, N
, N'-dimethylurea and other urea derivatives, methyl-(
Amino acid derivatives such as 2,4-dinitrophenyl)-aminopropanate, leucine-p-nitroanilide, 4
Examples include stilbene derivatives such as -dimethylamino-4-stilbene, heterocyclic compounds such as merocyanine, and molecular salts thereof.
本発明における薄膜作製方法としては、例えば、スペー
サを介した２枚の基板間に一般式（１）〜（ＩＶ）で示
される化合物を封入し、必要に応じて電界を印加するな
どの後処理を行ない配向薄膜とする従来の液晶セルの作
製方法や、真空蒸着で基板上に一般式（Ｉ）〜（ＩＶ）
で示される化合物を堆積させる方法などがある。この場
合に用いる基板としては、例えば、ガラス表面を一定方
向にラビングした基板、ＩＴＯ，ＳｎＯなどの透明電極
を持つガラスの表面を一定方向にラビングした基板、ポ
リイミド、ポリビニルアルコールなどの高分子膜をコー
ティングしたガラスの表面を一定方向にラビングした基
板、Ｓｉｎ、 ＳｉＯなどを斜蒸着しなガラス基板、Ｋ
Ｂｒ、 ＮａＣ１、サファイアなどの単結晶、およびこ
れらを組み合わせた基板などが使用できる。The method for producing a thin film in the present invention includes, for example, enclosing compounds represented by general formulas (1) to (IV) between two substrates via a spacer, and post-treatment such as applying an electric field as necessary. Conventional methods for manufacturing liquid crystal cells, in which an oriented thin film is formed by applying
There are methods such as depositing a compound shown in . Substrates used in this case include, for example, a substrate whose glass surface is rubbed in a certain direction, a substrate whose surface of glass with a transparent electrode such as ITO or SnO is rubbed in a certain direction, and a polymer film such as polyimide or polyvinyl alcohol. Substrates with coated glass surfaces rubbed in a certain direction, glass substrates with oblique evaporation of Sin, SiO, etc.
Single crystals such as Br, NaCl, and sapphire, and substrates combining these can be used.
以下、本発明を実施例によりさらに詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
（実施例１）
（１）〜（ＩＶ）式で表される化合物のうち代表的なも
のについて、粉末法により測定した二次非線形光学定数
の相対強度を第３表に示す、非線形光学定数測定時の基
準物質として尿素、光源には波長１．０６μｍのＹＡＧ
レーザを用いた。測定温度は室温である。また、第１表
のＤＯＢＡＭＢＣ，ＮＯＢＡＭＢＣの測定結果もあわせ
て第３表に示した。(Example 1) Table 3 shows the relative intensities of the second-order nonlinear optical constants measured by the powder method for typical compounds represented by formulas (1) to (IV). Urea is used as the reference material, and YAG with a wavelength of 1.06 μm is used as the light source.
A laser was used. The measurement temperature is room temperature. Furthermore, the measurement results for DOBAMBC and NOBAMBC in Table 1 are also shown in Table 3.
第３表に示した液晶性化合物は何れも従来の強誘電性液
晶に比べて大きな光非線形性を示し、有機非線形光学素
子用材料として有効であることがわかる。It can be seen that all of the liquid crystal compounds shown in Table 3 exhibit greater optical nonlinearity than conventional ferroelectric liquid crystals, and are effective as materials for organic nonlinear optical elements.
（実施例２）
ＩＴＣ）の透明電極付きガラス基板１の、電界印加用端
子３を有する透明電極２面をラビングし、２枚を１０μ
ｍのスペーサ（ポリイミド膜）４を介して対向させた第
１図に示す構造の液晶セルを作製した。すなわち
これに第２表の化合物ＩＣ〜ＩＨを液晶注入部５に注入
して二次非線形光学定数、偏光度を測定した結果を第４
表に示す、ここで、二次非線形光学定数の測定時には波
長１．０６μｍのＹＡＧレーザを光源として使用し、既
報（Ｎ、Ｍ、５ｈｔｙｋｏｖ、 Ｍ、１．Ｂａｒｎｉｋ
。(Example 2) Two surfaces of the transparent electrode having the electric field application terminal 3 of the glass substrate 1 with a transparent electrode manufactured by ITC were rubbed, and the two sheets were coated with a 10μ
A liquid crystal cell having the structure shown in FIG. 1 in which the liquid crystal cells were opposed to each other with a spacer (polyimide film) 4 of m in size interposed therebetween was fabricated. That is, the results of injecting the compounds IC to IH shown in Table 2 into the liquid crystal injection part 5 and measuring the second-order nonlinear optical constant and degree of polarization are shown in the fourth table.
Here, when measuring the second-order nonlinear optical constants, a YAG laser with a wavelength of 1.06 μm was used as a light source, as shown in the table.
.
Ｌ、Ａ、Ｂｅｒｅｓｎｅｖ、 Ｌ、Ｍ、Ｂ１１ｎｏｖ、
Ｍｏ１．Ｃｒｙｓｔ、Ｌｉｑ、ＣｒｙｓＬ、 １２４
゜３７９−３９０（１９８５））と同様の方法で測定を
行なった。L, A, Beresnev, L, M, B11nov,
Mo1. Cryst, Liq, CrysL, 124
Measurements were carried out in the same manner as in 379-390 (1985)).
また、偏向度Ｐ（ｄｅｇｒｅｅ ｏｆ ｐｏｌａｒｉｚ
ａｔｉｏｎ）の測定は、透過光強度が測定可能な偏光顕
微鏡を使用し、偏光オルソスコープ観察において最も明
るくなる対角位での測光値工 、および最も暗くなる消
光位での婁
測光値（対角位より４５°回転）■ を用いて（１）上
式により計算した。In addition, the degree of deflection P (degree of polariz
ation) is measured using a polarizing microscope that can measure the intensity of transmitted light, and the photometric value at the diagonal position where it is the brightest in polarized orthoscope observation, and the photometric value at the extinction position where it is the darkest (diagonal Calculated using the above formula (1) using
Ｐ＝（Ｉ −Ｉ ）／（Ｉ ＋Ｉ ”）
（１）瀧よ一工
化合物ＩＣ〜ＩＨは共に非線形光学定数が従来の検討例
に比べて非常に大きく、かつ、配向性も良好であること
がわかる。第３表の化合物を用いた場合にも同様の結果
が得られた。P=(I−I)/(I+I”)
(1) It can be seen that both Taki Yoichiko compounds IC to IH have significantly larger nonlinear optical constants than those of conventionally studied examples, and also have good orientation. Similar results were obtained using the compounds in Table 3.
（実施例３）
粉末法により測定した光非線形性が尿素の２２倍である
２−メチル−４−ニトロアニリン、および１１５倍の２
−アセチルアミノ−４−二トロジメチルアニリンと化合
物ＩＣ，ＩＥとを重量比５：９５で混合し、実施例１と
同様の方法で非線形光学定数および偏向度を測定した。(Example 3) 2-Methyl-4-nitroaniline, whose optical nonlinearity measured by the powder method is 22 times that of urea, and 2-methyl-4-nitroaniline, whose optical nonlinearity is 115 times that of urea.
-Acetylamino-4-nitrodimethyaniline and compounds IC and IE were mixed at a weight ratio of 5:95, and the nonlinear optical constants and degree of polarization were measured in the same manner as in Example 1.
結果を第５表に示す。The results are shown in Table 5.
大きな光非線形性を持つ化合物との混合により、光非線
形性がさらに向上したことが明らかである。It is clear that the optical nonlinearity was further improved by mixing with a compound having large optical nonlinearity.
（実施例４〉
ＩＴＯの透明電極付きガラス基板の透明電極面をラビン
グし、真空蒸着用基板とした。ラビングした面に真空蒸
着法で第３表の化合物１ｃ〜ＩＨおよびＩＲを蒸着して
二次非線形光学定数、偏光度を測定した結果を第６表に
示す。(Example 4) The transparent electrode surface of an ITO glass substrate with a transparent electrode was rubbed to obtain a substrate for vacuum deposition. Compounds 1c to IH and IR shown in Table 3 were deposited on the rubbed surface by a vacuum deposition method. Table 6 shows the results of measuring the order nonlinear optical constants and degree of polarization.
化合物ＩＣ〜ＩＨ１］Ｒは真空蒸着法によっても薄膜形
成が可能で、大きな非線形光学定数を有する薄膜が得ら
れることがわかる。第３表の他の化合物を用いた場合に
も同様の結果が得られた。It can be seen that the compounds IC to IH1]R can be formed into thin films by vacuum evaporation, and a thin film having large nonlinear optical constants can be obtained. Similar results were obtained using other compounds in Table 3.
（以下余白）
第３表（続き）
第３表
第３表（続き）
第３表（続き）
第３表（続き）
第３表（続き）
第４表
第６表
第５表
（発明の効果）
以上説明したように、本発明によれば、非線形性と配向
性の双方に優れる非線形光学材料および配向性に優れる
非線形光学薄膜を提供することができるため、オプトエ
レクトロニクス用として好適に使用できる。(Leaving space below) Table 3 (continued) Table 3 Table 3 (continued) Table 3 (continued) Table 3 (continued) Table 3 (continued) Table 4 Table 6 Table 5 (Effects of the invention ) As explained above, according to the present invention, it is possible to provide a nonlinear optical material that is excellent in both nonlinearity and orientation, and a nonlinear optical thin film that is excellent in orientation, so that it can be suitably used for optoelectronics.
第１図は本発明に用いた液晶用セルの構造を示した図で
ある。
１・・・ガラス基板、 ２・・・電界印加用の電極、３
・・・電界印加用端子、 ４・・・表面をラビング処理
したポリイミド膜、 ５・・・液晶注入部。FIG. 1 is a diagram showing the structure of a liquid crystal cell used in the present invention. 1... Glass substrate, 2... Electrode for applying electric field, 3
... Terminal for applying electric field, 4 ... Polyimide film whose surface has been subjected to rubbing treatment, 5 ... Liquid crystal injection part.
Claims (8)
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋ，ｌは０または１）で示される化合物を単独で、も
しくは他の化合物と混合して用いることを特徴とする有
機非線形光学素子用材料。(1) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R is an alkyl group or an alkyl group containing fluorine, and R^* is an optically active alkyl group or an ether bond. or an optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k, l are 0 or 1) is used alone or in combination with other compounds.
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋ，ｌは０または１）で示される化合物を単独で、も
しくは他の化合物と混合して用いることを特徴とする有
機非線形光学素子用材料。(2) The following general formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R is an alkyl group or an alkyl group containing fluorine, and R^* is an optically active alkyl group or an ether bond. or an optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k, l are 0 or 1) is used alone or in combination with other compounds.
基、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結
合を含む光学活性アルキル基、もしくはハロゲン原子を
含む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水
酸基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ
基、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、
ｊ，ｋ，ｌは０または１）で示される化合物を単独で、
もしくは他の化合物と混合して用いることを特徴とする
有機非線形光学素子用材料。(3) General formula (III) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. an alkyl group or an optically active alkyl group containing a halogen atom;
j, k, l are 0 or 1) alone,
Or a material for an organic nonlinear optical element, characterized in that it is used in combination with other compounds.
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋは０または１）で示される化合物を単独で、もしく
は他の化合物と混合して用いることを特徴とする有機非
線形光学素子用材料。(4) General formula (IV) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. Alkyl group or optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k is 0 or 1) is used alone or in combination with other compounds.
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋ，ｌは０または１）で示される化合物もし＜はこの
化合物と他の化合物と混合した組成物を使用したことを
特徴とする有機非線形光学薄膜。(5) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. Alkyl group or optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k, l are 0 or 1), and < is a composition in which this compound is mixed with another compound.
基、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結
合を含む光学活性アルキル基、もしくはハロゲン原子を
含む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水
酸基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ
基、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、
ｊ，ｋ，ｌは０または１）で示される化合物もしくはこ
の化合物と他の化合物と混合した組成物を使用したこと
を特徴とする有機非線形光学蒲膜。(6) General formula (II) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. an alkyl group or an optically active alkyl group containing a halogen atom;
An organic nonlinear optical capsule characterized in that it uses a compound represented by (j, k, l are 0 or 1) or a composition in which this compound is mixed with another compound.
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋ，ｌは０または１）で示される化合物もしくはこの
化合物と他の化合物と混合した組成物を使用したことを
特徴とする有機非線形光学薄膜。(7) General formula (III) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. Alkyl group or optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k, l are 0 or 1) or a composition in which this compound is mixed with another compound.
、Ｒ＾＊は光学活性アルキル基、もしくはエーテル結合
を含む光学活性アルキル基、もしくはハロゲン原子を含
む光学活性アルキル基、Ｘ，Ｙは水素、ハロゲン、水酸
基、シアノ基、ニトロ基、アミノ基、ジメチルアミノ基
、またはＲ＿１ＣＯＮＨ基（Ｒ＿１はアルキル基）、ｊ
，ｋ，ｌは０または１）で示される化合物もしくはこの
化合物と他の化合物と混合した組成物を使用したことを
特徴とする有機非線形光学薄膜。(8) General formula (IV) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R is an alkyl group or an alkyl group containing fluorine, R^* is an optically active alkyl group, or an optically active group containing an ether bond. Alkyl group or optically active alkyl group containing a halogen atom, X and Y are hydrogen, halogen, hydroxyl group, cyano group, nitro group, amino group, dimethylamino group, or R_1CONH group (R_1 is an alkyl group), j
, k, l are 0 or 1) or a composition in which this compound is mixed with another compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1002610A JP2742697B2 (en) | 1989-01-09 | 1989-01-09 | Material for organic nonlinear optical element and organic nonlinear optical thin film using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1002610A JP2742697B2 (en) | 1989-01-09 | 1989-01-09 | Material for organic nonlinear optical element and organic nonlinear optical thin film using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02183231A true JPH02183231A (en) | 1990-07-17 |
| JP2742697B2 JP2742697B2 (en) | 1998-04-22 |
Family
ID=11534167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1002610A Expired - Fee Related JP2742697B2 (en) | 1989-01-09 | 1989-01-09 | Material for organic nonlinear optical element and organic nonlinear optical thin film using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2742697B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020058A2 (en) * | 1991-04-24 | 1992-11-12 | University Research Corporation | Ferroelectric liquid crystals for nonlinear optics applications |
| GB2285810A (en) * | 1994-01-10 | 1995-07-26 | Secr Defence | Smectic liquid crystal materials for electroclinic or nonlinear optic devices |
| US5453218A (en) * | 1988-03-04 | 1995-09-26 | Displaytech, Inc. | Liquid crystal compounds containing chiral 2-halo-2 methyl alkoxy tails |
-
1989
- 1989-01-09 JP JP1002610A patent/JP2742697B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| OPTICS COMMUNICATIONS * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5453218A (en) * | 1988-03-04 | 1995-09-26 | Displaytech, Inc. | Liquid crystal compounds containing chiral 2-halo-2 methyl alkoxy tails |
| WO1992020058A2 (en) * | 1991-04-24 | 1992-11-12 | University Research Corporation | Ferroelectric liquid crystals for nonlinear optics applications |
| WO1992020058A3 (en) * | 1991-04-24 | 1993-03-04 | Univ Research Corp | Ferroelectric liquid crystals for nonlinear optics applications |
| US5637256A (en) * | 1991-04-24 | 1997-06-10 | University Research Corporation | Ferroelectric liquid crystals for nonlinear optics applications |
| US5658493A (en) * | 1991-04-24 | 1997-08-19 | University Research Corporation | Ferroelectric liquid crystals for nonlinear optics applications |
| GB2285810A (en) * | 1994-01-10 | 1995-07-26 | Secr Defence | Smectic liquid crystal materials for electroclinic or nonlinear optic devices |
| US5891358A (en) * | 1994-01-10 | 1999-04-06 | Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian & Northern Ireland Of Defence Evaluation & Research Agency | Liquid crystal mixtures and devices |
| US6242636B1 (en) | 1994-01-10 | 2001-06-05 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland Of Defence Evaluation And Research Agency | Liquid crystal compounds, mixtures and devices |
| US6278028B1 (en) | 1994-01-10 | 2001-08-21 | The Secretary Of State For In Defence In Her Brittanic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compounds, mixtures and devices |
| US6337420B1 (en) | 1994-01-10 | 2002-01-08 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Defence Evaluation Research Agency | Liquid crystal compounds, mixtures and devices |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2742697B2 (en) | 1998-04-22 |
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