JPH0469624A - Nonlinear optical material - Google Patents
Nonlinear optical materialInfo
- Publication number
- JPH0469624A JPH0469624A JP18363790A JP18363790A JPH0469624A JP H0469624 A JPH0469624 A JP H0469624A JP 18363790 A JP18363790 A JP 18363790A JP 18363790 A JP18363790 A JP 18363790A JP H0469624 A JPH0469624 A JP H0469624A
- Authority
- JP
- Japan
- Prior art keywords
- group
- nonlinear optical
- optical material
- chemical formula
- butyl group
- 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.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 47
- 239000000463 material Substances 0.000 title claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 2
- -1 nitrophenylcarbamate ester Chemical class 0.000 claims description 7
- 239000013078 crystal Substances 0.000 abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 abstract description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229910052805 deuterium Inorganic materials 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- FRQWVAWXEBTURS-UHFFFAOYSA-N (2-nitrophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC=C1[N+]([O-])=O FRQWVAWXEBTURS-UHFFFAOYSA-N 0.000 abstract 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- QDACQOOLIVCDNP-UHFFFAOYSA-N 2-nitro-1-oxidopyridin-1-ium Chemical class [O-][N+](=O)C1=CC=CC=[N+]1[O-] QDACQOOLIVCDNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000005274 electronic transitions Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- DAWCBJXIGOELKF-UHFFFAOYSA-N methyl n-(4-nitrophenyl)carbamate Chemical compound COC(=O)NC1=CC=C([N+]([O-])=O)C=C1 DAWCBJXIGOELKF-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- UYLYBEXRJGPQSH-UHFFFAOYSA-N sodium;oxido(dioxo)niobium Chemical compound [Na+].[O-][Nb](=O)=O UYLYBEXRJGPQSH-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer 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、可視域における透明性がよく、二次の非線形
光学効果の大きい反転対称中心のない結晶を形成するこ
とができる有機質の非線形光学化合物に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an organic nonlinear optical system that can form a crystal without a center of inversion symmetry that has good transparency in the visible range and a large second-order nonlinear optical effect. Regarding compounds.
非線形光学効果とは、非常に強い光が物体を透過すると
き、光の電場によって物質が分極し、この誘起分極によ
る光高調波の発生や、入射した光自身が変化する現象を
いう。A nonlinear optical effect is a phenomenon in which when extremely strong light passes through an object, the material is polarized by the electric field of the light, and this induced polarization generates optical harmonics and changes the incident light itself.
この現象は、レーザーの発明以前から知られていたもの
であるが、多くはレーザー光の出現によっ′ζ注目され
るようになった。特に最近、光機能素子への応用が注目
されている光高調波発生、光パラメトリツク発振・増幅
、光位相共役、光双安定などの現象解明はレーザーの発
明に負・）とごろが大きい。これらの非線形光学効果は
、赤外光の可視光、紫外光−４の変換、光増幅、光スィ
ッチ、光変調、光信号などの無歪伝送など・＼の応用が
可能である。非線形光学効果素子は、今後ますまず需要
が増大する光情報処理１．光通信の分野で鍵を握る機能
材料として位置づけされ°Ｃいる。Although this phenomenon was known before the invention of lasers, it has received much attention since the advent of laser light. In particular, the elucidation of phenomena such as optical harmonic generation, optical parametric oscillation and amplification, optical phase conjugation, and optical bistability, which have recently been attracting attention for application to optical functional devices, has had a negative impact on the invention of the laser. These nonlinear optical effects can be applied to the conversion of infrared light to visible light and ultraviolet light, optical amplification, optical switches, optical modulation, distortion-free transmission of optical signals, etc. Nonlinear optical effect elements are used in optical information processing, for which demand will increase rapidly in the future.1. It is positioned as a key functional material in the field of optical communications.
従来、非線形光学効果を示す−物質としζ、例えば、リ
ン酸２水素カリウム（ＫＤＰ）、ニオブ酸すチウＪ、（
ＬｉＮｂ０３）、β−ホウ酸バリウム（ＢＢＯ）などが
研究され、一部は素子材料として実用化されている。し
かし、非線形光学効果を示す物質は無機誘電体化合物に
限られるものでなく、有機化合物の中にも見い出されて
いる。しかも有機化合物の非線形光学作用は、分子内に
非局在化しているπ電子の移動によって生じるため、原
ｒ核に強く束縛され格子振動に制約がある無機誘電体の
σ電子に比べて、誘起分極は描かに速く大きい。実際、
２−メヂル−４−ニトロアニリン（ＭＮＡ）は、ニオブ
酸リチウムの２０００倍以十、の性能指数を示ｔ （Ｂ
、Ｆ、１．ＥＶＩＮＥ ｅｔ ａｔ、Ｊ、Δｐｐｔｙ、
ｐｈｙｓ、、Ｖｏ１．５０．２５２３（１９７９） ）
。Conventionally, materials exhibiting nonlinear optical effects have been considered as ζ, such as potassium dihydrogen phosphate (KDP), sodium niobate, (
LiNb03), β-barium borate (BBO), etc. have been studied, and some of them have been put into practical use as element materials. However, substances exhibiting nonlinear optical effects are not limited to inorganic dielectric compounds, but are also found among organic compounds. Moreover, the nonlinear optical action of organic compounds is caused by the movement of π electrons, which are delocalized within the molecule. The polarization is surprisingly fast and large. actual,
2-Medyl-4-nitroaniline (MNA) exhibits a figure of merit more than 2000 times that of lithium niobate.
,F,1. EVINE et at, J, Δppty,
phys,, Vo1.50.2523 (1979))
.
このようなことから、非線形光学効果の中でも光機能素
子としての応用が最も早く期待されているニー次の非線
形光学効果、特に光第二高調波発生（Ｓ ＨＧ ）の実
用化研究が有機化合物を対象に精力的に進められており
、例えば、ＭＮＡ （特開昭５５−５００９６０号公報
）、ニトロピリジン−１−オキシド誘導体（特開昭５６
−９２８７０号公報、同５６−９４３３３号公報）等の
物質が非線形光学化合物として既に提案されている。For this reason, practical research on the second-order nonlinear optical effect, especially optical second harmonic generation (SHG), which is expected to be the earliest to be applied as an optical functional element among nonlinear optical effects, is focusing on organic compounds. For example, MNA (JP-A-55-500960), nitropyridine-1-oxide derivatives (JP-A-56-500960),
Substances such as JP-A-92870 and JP-A-56-94333 have already been proposed as nonlinear optical compounds.
有機化合物において、二次の非線形光学効果を高めるに
は分子の双極子モーメントを大きくすればよく、そのた
めには分子内に電子供与性基と電子吸引性基を導入する
ことが有効であることば良く知られている。In organic compounds, in order to enhance the second-order nonlinear optical effect, it is sufficient to increase the dipole moment of the molecule, and for this purpose, it is effective to introduce an electron-donating group and an electron-withdrawing group into the molecule. Are known.
しかし、この点には重要な未解決の課題が残されている
。即し、反転対称中心のない結晶でなければならないこ
とである。ところが分子内に大きな双極子モーメントを
持つ有機化合物は、結晶化する場合に互いの双極子モー
メントを打ち消し合うよ・）に配置する結果、分子とし
ては大きな二次の超分子分極率βをもちながら結晶ある
いは分子集合体としては反転対称中心があるため二次の
非線形光学効果を示さないことがある。また、大きな分
子内電荷移動のため近紫外から可視域に電子遷移吸収が
存在し、光学材ネ：１として重要な透明性をＩｊＪなう
ことにもつながる。実際にこのような有機化合物は非常
に多い。However, important unresolved issues remain in this regard. In other words, it must be a crystal without a center of inversion symmetry. However, when organic compounds with large dipole moments in their molecules cancel out each other's dipole moments when they crystallize, as a result of their arrangement, the molecules have a large second-order supramolecular polarizability β. As a crystal or molecular aggregate, it may not exhibit second-order nonlinear optical effects because it has a center of inversion symmetry. Further, due to large intramolecular charge transfer, electronic transition absorption exists in the near-ultraviolet to visible range, which leads to IjJ, which is important for transparency as an optical material. In fact, there are a large number of such organic compounds.
従って、二次の非線形光学効果を主眼とする有機非線形
光学化合物を開発するに当たっては、透明性をＩ員なわ
ずに、分子として充分大きな超分子分極率βを持ち、反
転対称中心のない良質な結晶が容易乙こ得られるような
化合物を合成することが重要な課題である。Therefore, when developing an organic nonlinear optical compound that focuses on second-order nonlinear optical effects, it is necessary to create a high-quality compound that has a sufficiently large supramolecular polarizability β and has no center of inversion symmetry, without requiring transparency. An important challenge is to synthesize compounds from which crystals can be easily obtained.
’＋Ｌ 了吸引性ｕ ？＝ ｊ３ 了ｍ ｌｉｌ！［ｈ
ｓ ２ 配すル芳香族化合物の二次の超分子分極率βと
透明性との関係、対称性の改質について鋭意検討した結
果、ある種のニトロフェニルカルバミン酸エステル誘導
体は大きな二次の超分子分極率βを持ち、結晶や分子集
合体を形成した際に反転対称中心を持たないこと、さら
に近紫外から可視域に於ける透明性を著しく改良しうろ
ことを確認し゛ζ本発明の開発に至ったものである。'＋L Attractive u? = j3 completed lil! [h
As a result of intensive studies on the relationship between the second-order supramolecular polarizability β and transparency of aromatic compounds arranged in s2, and the modification of symmetry, we found that certain nitrophenyl carbamate ester derivatives have large second-order supramolecular polarizability β and transparency. Development of the present invention was confirmed by confirming that it has a molecular polarizability β, does not have a center of inversion symmetry when formed into a crystal or molecular aggregate, and has significantly improved transparency in the near-ultraviolet to visible range. This is what led to this.
本発明の目的とするところは、可視域におｉする透明性
がよく、二次の非線形光学効果の大きい反転対称中心の
ない結晶を形成することができる１１機質の非線形光学
材料を提供するところにある。An object of the present invention is to provide a nonlinear optical material of 11 properties that has good transparency in the visible range and can form a crystal without a center of inversion symmetry that has a large second-order nonlinear optical effect. It's there.
上記の目的を達成するための本発明による非線形光学材
料は、下記の化学式で表されるニトロフェニルカルバミ
ン酸エステル誘導体からなることを構成−ヒの特徴とす
る。The nonlinear optical material according to the present invention for achieving the above object is characterized in that it is composed of a nitrophenyl carbamate ester derivative represented by the following chemical formula.
上記化学式のニトロフェニルカルバミン酸エステル誘導
体は、例えばニトロフェニルイソシアナートを、酸［Ｂ
Ｆ３ ・Ｅｔ、０、ＨＣｌ、、ＡｌＣｌ３、Ｒ，Ｓｎ
（ＯＡｃ）ｚなど）あるいは塩基（Ｅｊ３Ｎ、ピリジン
、Ａｃ０Ｎａなど）を触媒として、Ｒに相当するアルコ
ール溶媒中で反応させることによって得られる。The nitrophenyl carbamate ester derivative of the above chemical formula can be used, for example, to convert nitrophenyl isocyanate into an acid [B
F3 ・Et, 0, HCl, , AlCl3, R, Sn
(OAc)z, etc.) or a base (Ej3N, pyridine, Ac0Na, etc.) as a catalyst in an alcohol solvent corresponding to R.
得られたニトロフェニルカルバミン酸エステル誘導体は
、粉末状態でＮｄ：ＹＡＧレーザ−（λ−１０６４ｒ＋
ｍ）を照射すると、著しく強い緑色の第二高調波を発生
する。更に単結晶状態では、広範囲に及んで位相整合可
能であり、粉末を遥かに越える強度の第二高調波を発生
するものも存在する。The obtained nitrophenylcarbamate ester derivative was heated in powder form with a Nd:YAG laser (λ-1064r+
When irradiated with m), a significantly strong green second harmonic is generated. Furthermore, in the single crystal state, phase matching is possible over a wide range, and some materials generate second harmonics with an intensity far exceeding that of powder.
一般に、結晶中の基本波と高調波の伝搬定数は一致しな
いため結晶状態での高調波発生は難しい、これが一致す
ることを位相整合といい、この位相整合がとれないと高
調波の発生を観測することばできない。Generally, it is difficult to generate harmonics in a crystal state because the propagation constants of the fundamental wave and harmonics in a crystal do not match.This matching is called phase matching, and if this phase matching cannot be achieved, harmonic generation will be observed. I can't say what to do.
また、粉末状態で白色または乳白色、単結晶状態で無色
透明であり、カットオフ波長は大幅に短波長シフトして
いる。In addition, it is white or milky white in powder form and colorless and transparent in single crystal form, and its cutoff wavelength has been significantly shifted to shorter wavelengths.
基本波が１〜１．２μｍの赤外光の場合、Ｃ−Ｈの伸縮
振動の倍音吸収と重なって基本波が吸収され、熱振動に
転化することがある。従って、基本波の強度が強いとき
は結晶の温度が上がり位相整合条件が変わったり、出射
光の角度が変わってしまう。When the fundamental wave is infrared light with a wavelength of 1 to 1.2 μm, the fundamental wave may be absorbed overlapping with overtone absorption of the C-H stretching vibration and converted into thermal vibration. Therefore, when the intensity of the fundamental wave is strong, the temperature of the crystal rises and the phase matching conditions change or the angle of the emitted light changes.
本発明において特に倍音吸収が大きいアルキル基の水素
を重水素で置換した化合物形態を採ると、吸収の領域が
長波長側にずれてこの現象を有効に防止することができ
る。In the present invention, if a compound form is adopted in which the hydrogen of an alkyl group with particularly large overtone absorption is replaced with deuterium, the absorption region shifts to the longer wavelength side, and this phenomenon can be effectively prevented.
本発明によれば、大きな双極子モーメントのため反転対
称中心の結晶を形成する傾向の強い有機化合物にカルバ
ミン酸エステル基を導入することによって対称性を低下
させ、広波長域において一次の非線形光学効果に対して
活性な材質に転化させた新規物性の非線形光学材料が提
供される。According to the present invention, by introducing a carbamate ester group into an organic compound that has a strong tendency to form a crystal with a center of inversion symmetry due to a large dipole moment, the symmetry is reduced and a first-order nonlinear optical effect is produced in a wide wavelength range. Provided is a nonlinear optical material with novel physical properties that has been converted into a material that is active against.
以下、本発明を実施例に基づいて説明する。 Hereinafter, the present invention will be explained based on examples.
実施例１
４−ニトロフェニルイソシアナート８．０ｇ（６０ｍｍ
ｏｆ）、触媒量のジラウリル酸ｎ−ブチルずず（２ｍｍ
ｏｊ２＞をメタノール、テトラハイドロフラン１：１混
合溶媒に溶解し水浴中５０°Ｃに保ち、約４時間攪拌反
応させた。反応終了後、濃縮析出した反応物を水、ヘキ
サンにて洗浄後、減圧下５０°Ｃで乾燥して４−ニトロ
フェニルカルバミン酸メチルエステルを得た。Example 1 4-nitrophenyl isocyanate 8.0g (60mm
of), a catalytic amount of n-butyl dilaurate (2 mm
oj2> was dissolved in a 1:1 mixed solvent of methanol and tetrahydrofuran, kept at 50°C in a water bath, and reacted with stirring for about 4 hours. After the reaction was completed, the concentrated and precipitated reaction product was washed with water and hexane, and then dried at 50°C under reduced pressure to obtain 4-nitrophenylcarbamic acid methyl ester.
実施例２〜８
上記の製法に従い、Ｒが異なる各種の４−ニトロフェニ
ルカルバミン酸エステル誘導体を合成した。Examples 2 to 8 Various 4-nitrophenylcarbamate ester derivatives having different R were synthesized according to the above production method.
上記の各非線形光学化合物を粒径６０〜１００μｍに調
製した試料をスライドガラスに挟み、これにＱスイ・ン
チイ寸きＮｄ：ＹＡＧレーザーによる１ｏｎｓｅｃのパ
ルスを照射し、試料より発生した第二高調波の強度を測
定した。ＳＨＧ強度は、尿素を１とした相対強度比で表
した。その結果を第１表に示す。A sample of each of the above nonlinear optical compounds prepared with a particle size of 60 to 100 μm was sandwiched between slide glasses, and a 1-on-second pulse was irradiated with a Q-swim-sized Nd:YAG laser to generate second harmonics from the sample. The strength was measured. The SHG intensity was expressed as a relative intensity ratio with urea as 1. The results are shown in Table 1.
以上のとおり、ニトロフェニルカルバミン酸エステル誘
導体は、カットオフ波長が短波長域に存在するにもかか
わらず、非常に大きな二次の超分子分極率βを有し、ま
たその結晶は反転対称中心がなく、その中で分子が互い
の双極子モーメントを打ち消し合わず有効に活かせるよ
うなよい配向を示すため、尿素に比べ高いＳＨＧ効率を
示す。As mentioned above, nitrophenylcarbamate ester derivatives have a very large second-order supramolecular polarizability β, even though their cutoff wavelength is in the short wavelength range, and their crystals have a center of inversion symmetry. It exhibits a good SHG efficiency compared to urea because the molecules exhibit a good orientation in which their dipole moments are effectively utilized without canceling each other out.
従って、波長変換素子、光制御素子などの非線形光学効
果及び電気光学効果を利用した各種の光機能素子材料と
して様々な用途が広波長域で期待できる。Therefore, various uses can be expected in a wide wavelength range as materials for various optical functional devices that utilize nonlinear optical effects and electro-optic effects, such as wavelength conversion devices and light control devices.
出願人 宮 １）清 蔵（外２名） 代理人 弁理士 高 畑 正 也Applicant: Miya 1) Kiyoshi (2 others) Agent: Patent Attorney Masaya Takahata
Claims (1)
酸エステル誘導体からなることを特徴とする非線形光学
材料。 ▲数式、化学式、表等があります▼ 但し、上式において、Ｒはアルキル基または重水素置換
されたアルキル基からなる群より選ばれた基を指すもの
とする。 ２、化学式中の基Ｒが、メチル基、ｎ−プロピル基、ｓ
ｅｃ−ブチル基またはｔｅｒｔ−ブチル基である請求項
１記載の非線形光学材料。 ３、化学式中の基Ｒが、エチル基である請求項１記載の
非線形光学材料。 ４、化学式中の基Ｒが、ｉｓｏ−プロピル基である請求
項１記載の非線形光学材料。 ５、化学式中の基Ｒが、ｎ−ブチル基である請求項１記
載の非線形光学材料。 ６、化学式中の基Ｒがｉｓｏ−ブチル基である請求項１
記載の非線形光学材料。[Claims] 1. A nonlinear optical material comprising a nitrophenylcarbamate ester derivative represented by the following chemical formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ However, in the above formula, R refers to a group selected from the group consisting of an alkyl group or a deuterium-substituted alkyl group. 2. The group R in the chemical formula is a methyl group, n-propyl group, s
The nonlinear optical material according to claim 1, which is an ec-butyl group or a tert-butyl group. 3. The nonlinear optical material according to claim 1, wherein the group R in the chemical formula is an ethyl group. 4. The nonlinear optical material according to claim 1, wherein the group R in the chemical formula is an iso-propyl group. 5. The nonlinear optical material according to claim 1, wherein the group R in the chemical formula is an n-butyl group. 6.Claim 1, wherein the group R in the chemical formula is an iso-butyl group.
Nonlinear optical materials described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18363790A JPH0469624A (en) | 1990-07-10 | 1990-07-10 | Nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18363790A JPH0469624A (en) | 1990-07-10 | 1990-07-10 | Nonlinear optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0469624A true JPH0469624A (en) | 1992-03-04 |
Family
ID=16139269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18363790A Pending JPH0469624A (en) | 1990-07-10 | 1990-07-10 | Nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0469624A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743373B1 (en) * | 1999-04-21 | 2004-06-01 | Solvay (Societe Anonyme) | Process for the separation of enantiomers and enantiopure reagent |
| US7138538B2 (en) | 2000-04-14 | 2006-11-21 | Solvay (Societe Anonyme) | Process for the separation of enantiomers and enantiopure reagent |
-
1990
- 1990-07-10 JP JP18363790A patent/JPH0469624A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743373B1 (en) * | 1999-04-21 | 2004-06-01 | Solvay (Societe Anonyme) | Process for the separation of enantiomers and enantiopure reagent |
| US7138538B2 (en) | 2000-04-14 | 2006-11-21 | Solvay (Societe Anonyme) | Process for the separation of enantiomers and enantiopure reagent |
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