JPH02301728A - Nonlinear optical material and production thereof - Google Patents
Nonlinear optical material and production thereofInfo
- Publication number
- JPH02301728A JPH02301728A JP12218689A JP12218689A JPH02301728A JP H02301728 A JPH02301728 A JP H02301728A JP 12218689 A JP12218689 A JP 12218689A JP 12218689 A JP12218689 A JP 12218689A JP H02301728 A JPH02301728 A JP H02301728A
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- shg
- crystal orientation
- cooling
- melting
- 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 28
- 239000000463 material Substances 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000013078 crystal Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 7
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims abstract description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 14
- 230000001747 exhibiting effect Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 230000000638 stimulation Effects 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 239000011521 glass Substances 0.000 abstract description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- -1 nitroaniline compound Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000013307 optical fiber Substances 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical class C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical class C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- QIFZZXZSSXRDOT-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C=CC(=O)C1=CC=C(N)C=C1 QIFZZXZSSXRDOT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- XUGISPSHIFXEHZ-UHFFFAOYSA-N 3beta-acetoxy-cholest-5-ene Natural products C1C=C2CC(OC(C)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XUGISPSHIFXEHZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005148 Cholesterol Benzoate Substances 0.000 description 1
- BSOLAQMZTBVZLA-QMMMGPOBSA-N L-tyrosinyl radical Chemical group OC(=O)[C@@H](N)CC1=CC=C([O])C=C1 BSOLAQMZTBVZLA-QMMMGPOBSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- XUGISPSHIFXEHZ-VEVYEIKRSA-N cholesteryl acetate Chemical compound C1C=C2C[C@@H](OC(C)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XUGISPSHIFXEHZ-VEVYEIKRSA-N 0.000 description 1
- UVZUFUGNHDDLRQ-LLHZKFLPSA-N cholesteryl benzoate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)C1=CC=CC=C1 UVZUFUGNHDDLRQ-LLHZKFLPSA-N 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical group C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 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
- 239000000758 substrate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は非線形光学特性を示す各種光素子への応用が可
能な 結晶配向性の高い非線形光学材料及びその非線形
光学材料の結晶配向を任意に揃えることが可能な製造方
法に関する。[Detailed Description of the Invention] Industrial Field of Application The present invention can be applied to various optical devices exhibiting nonlinear optical characteristics. Nonlinear optical materials with high crystal orientation and the ability to arbitrarily align the crystal orientation of the nonlinear optical material. This invention relates to a manufacturing method that allows for.
従来の技術
将来の光素子に有用な光学材料として、大きな非線形光
学特性を有し 高速応答する材料が求められている。こ
のような材料として（よ 格子振動が関与する無機化合
物結晶より耘 π電子系を有する有機化合物の方が優れ
ているとされ 設計指針としてはπ電子共役系を有する
分子に 強いドナー性置換基とアクセプター性置換基を
導入する方法が一般的であっ九
発明が解決しようとする課題
しかし このような方法では有機分子単一では非常に大
きな超分極率を持つにもかかわら咀 分子内部で誘起さ
れた双極子モーメントが他分子と相互作用を起こし 打
ち消し合うような中心対称性の結晶が形成される。そし
て、このような中心対称性の結晶においては２次の非線
形光学特性であるＳＨＧは現れないという課題があっ池
課題を解決するための手段
２次の非線形光学特性を示す有機化合物と結晶配向方向
を任意に揃えられる有機化合物とを少なくとも２種以上
混合溶融し 冷却固化させた構成とする。Conventional Technology Materials with large nonlinear optical properties and high-speed response are required as optical materials useful for future optical devices. As such materials, organic compounds with a π-electron system are said to be superior to inorganic compound crystals in which lattice vibrations are involved. A common method is to introduce an acceptor substituent, but the problem to be solved by this invention is that although a single organic molecule has a very large hyperpolarizability, hyperpolarizability is induced inside the molecule. A centrosymmetric crystal is formed in which the dipole moment interacts with other molecules and cancels each other out.It is said that SHG, which is a second-order nonlinear optical property, does not appear in such a centrosymmetric crystal. Problems AchievedMeans for Solving the Problems The present invention has a composition in which at least two kinds of organic compounds exhibiting second-order nonlinear optical characteristics and organic compounds whose crystal orientation can be arbitrarily aligned are mixed and melted, cooled, and solidified.
作用
本発明者等は 単独の結晶ではＳ、ＨＧ活性を示さない
化合物でも結晶配向性の高い他の化合物と混合溶融し
冷却固化させることによって高効率のＳＨＧ活性を現わ
すことが可能であることを見いだし九
すなわち、分子の超分極率βは大きい力＼ 中心対称性
の結晶を形成するために 単独ではＳ ＨＧ不活性であ
る化合物でも結晶配向性の高い他の化合物との複合系に
することにより中心対称性の存在しない構造（即ちＳ
ＨＧ活性の構造）に変えることができる。Effect The present inventors have discovered that even compounds that do not exhibit S or HG activity when used alone as crystals can be mixed and melted with other compounds that have high crystal orientation.
We found that it is possible to exhibit highly efficient SHG activity by cooling and solidifying.9 In other words, the hyperpolarizability β of the molecule is a large force, and in order to form a centrosymmetric crystal, SHG alone becomes inactive. Even if a compound has a structure with no central symmetry (i.e., S
structure of HG activity).
また ２次の非線形光学特性を示す有機化合物と結晶配
向性の高い有機化合物とを少なくとも２種以上混合溶融
させ、その混合溶融物を冷却固化させる過程において、
電気向 熱的あるいは機械的刺激を与えることにより任
意の方向に結晶配向を揃えた非線形光学素子の製造が可
能となる。In addition, in the process of mixing and melting at least two organic compounds exhibiting second-order nonlinear optical properties and organic compounds with high crystal orientation, and cooling and solidifying the mixed melt,
By applying electrothermal or mechanical stimulation, it is possible to manufacture nonlinear optical elements with crystal orientation aligned in any direction.
実施例 以下に実施例を用いて本発明の詳細な説明する。Example The present invention will be described in detail below using examples.
実施例１
バラニトロアニリン（ＰＮＡ、関東化学社製）及びジフ
ェニルエチレンジアミン（ＤＰＥＮ、関東化学社製）を
種々のモル比で混合し 溶融させた後、冷却固化させ九
得られた組成物にＮｄ： ＹＡＧレーザ−（１０６
４ｎｍ）を用いてＳＨＧ強度の測定を行なったとこへ
第１図で示すようにＰＮＡのモル比（ＰＮＡ／ＤＰＥＮ
）が０．２〜０．０９の領域で非常に高い効率の（尿素
比４０倍程度）のＳＨＧが観測された 上記の化合物単
独で１ｉｓＨＧが全く観測されないことから、 ２種以
上の有機化合物を混合溶融し冷却固化させることにより
、新たな組成物が形成され この組成物が極めて高いＳ
ＨＧ効率を示す構造を有しているものと考えら・れる。Example 1 Varanitroaniline (PNA, manufactured by Kanto Kagaku Co., Ltd.) and diphenylethylenediamine (DPEN, manufactured by Kanto Kagaku Co., Ltd.) were mixed in various molar ratios, melted, and then cooled and solidified.9 Nd: YAG laser (106
4nm) was used to measure the SHG intensity.
As shown in Figure 1, the molar ratio of PNA (PNA/DPEN
) was observed in the region of 0.2 to 0.09, SHG with very high efficiency (approximately 40 times that of urea) was observed. Since no 1isHG was observed with the above compound alone, it was found that 1isHG was observed with two or more organic compounds. By mixing, melting, cooling and solidifying, a new composition is formed and this composition has an extremely high S
It is thought that it has a structure that exhibits HG efficiency.
この組成物の構造について（よ 現在のところ詳細は不
明である力丈 各々の分子が持っている双極子モーメン
トを打ち消し合わない構成 即ち非中心対称の構造を有
するものと考えられる。また ２種の分子が錯体もしく
は分子化合物を形成し全体として中心対称の無い構造を
とっているとも考えられる。Regarding the structure of this composition (the details are currently unknown), it is thought that it has a structure in which the dipole moments of each molecule do not cancel each other out, that is, it has a non-centrosymmetric structure. It is also thought that the molecules form a complex or a molecular compound, and the structure as a whole lacks central symmetry.
本発明でいうπ電子系共役系有機化合物と（上上記のＰ
ＮＡ等のニトロアニリン系化合物誘導体の他にドナー性
及びアクセプター性の置換基を有する芳香環化合１扱
スチルベン系化合物誘導体やベンザルアセトフェノン誘
導体等の共役オレフィン化合１扱 ベンゾオキサジアゾ
ール誘導体やニトロピリジン誘導体等の複素環化合１扱
ベンジリデンアニリン誘導体等の芳香環を有するシッ
フベース化合物等が本発明に適用可能である。具体的に
（よ１．４置換ナフタレン誘導体 ４−ジメチルアミノ
−４−スチルベン、３−（４−メトキシフェニル）−１
−（４−アミノフェニル）−２−プロペン−１−オン、
カルコン誘導体 ４−ニトロ−７−クロロベンゾオキサ
ジアゾール４′−ニトロベンジリデン−３−アセチルア
ミノ−４−メトキシアニリン、Ｎ−（４−ピリジニルメ
チレン）−４−ジメチルアミノベンゼナミン・ジメチル
スルフェート、Ｎ−［２−（５−ニトロベンジリデン）
］−］４−メトキシベンゼナミン及びこれらの類似化合
物が適用可能である。本発明で言うドナー性置換基とし
て（よ例えば アミ人 モノメチルアミ人 ジメチルア
ミ人 ジエチルアミ人 ｎ−ブチルアミ人 ｔ−ブチル
アミノ等のアミノ暴Ｌ−（２−ヒドロキシメチル）−ピ
ロリジニ／ｋ Ｌ−アラニニノＬ／Ｘ Ｌ−セリ二ノｋ
Ｌ−チロシニル等光学活性アミノ基 ヒドロキシ、メト
キシ、エトキシ、 ｎ−ブトキシ等のアルコキシ展メチ
ル、エチル、 ｎ−プロピ）Ｉｙ、 ｎ−ブチ）Ｉｔ
、 ｎ−ペンデル ｎ−オクタデシル等の鎖状または
分岐状のアルキル展 ハロゲン等が挙げられ 一方、ア
クセプター性の置換基として（よ ニトロ、シア人イソ
シアナト、ホルミ／ｌｚ、 カルボン酸メチル、カル
ボン酸エチル等のアルコキシカルボニ／は スルフォニ
ル、ハロゲン等が挙げられる。ハロゲンはドナー性、ア
クセプター性、両方の性質を持っているたム どちらの
範鴎にも入る。また本発明で言うカルボニル基を有する
溶媒としてζよ アセトン、メヂルエチルケトン、シク
ロヘキザノス ジエチルケトン、２−ブタノン等のケト
ン類及びアセトフェノン、アセトアルデヒド、ポルムア
ルデヒド等のアルデヒド類が挙げられる。The π-electron conjugated organic compound referred to in the present invention (the above P
Aromatic ring compounds having donor and acceptor substituents in addition to nitroaniline compound derivatives such as NA
Conjugated olefin compounds such as stilbene derivatives and benzalacetophenone derivatives (1) Heterocyclic compounds (1) such as benzoxadiazole derivatives and nitropyridine derivatives Schiff base compounds with aromatic rings such as benzylideneaniline derivatives are applicable to the present invention. It is. Specifically (1.4-substituted naphthalene derivatives 4-dimethylamino-4-stilbene, 3-(4-methoxyphenyl)-1
-(4-aminophenyl)-2-propen-1-one,
Chalcone derivatives 4-nitro-7-chlorobenzoxadiazole 4'-nitrobenzylidene-3-acetylamino-4-methoxyaniline, N-(4-pyridinylmethylene)-4-dimethylaminobenzenamine dimethylsulfate , N-[2-(5-nitrobenzylidene)
]-]4-methoxybenzenamine and similar compounds thereof are applicable. In the present invention, the donor substituents (for example, amino groups such as amino group, monomethyl group, dimethyl group, diethyl group, n-butylamino group, t-butylamino group, L-(2-hydroxymethyl)-pyrrolidini/k L-alaninino L/ XL-Selinino k
Optically active amino groups such as L-tyrosinyl, alkoxy groups such as hydroxy, methoxy, ethoxy, n-butoxy, methyl, ethyl, n-propy)Iy, n-buty)It
, n-pendel, n-octadecyl, and other linear or branched alkyl-extended halogens.On the other hand, acceptor substituents include (nitro, cyanide isocyanato, formi/lz, methyl carboxylate, ethyl carboxylate, etc.). Examples of alkoxycarbonyl/ include sulfonyl, halogen, etc. Halogen has both donor and acceptor properties, so it falls into both categories.Also, as a solvent having a carbonyl group in the present invention, Examples include ketones such as acetone, medylethyl ketone, cyclohexanos diethyl ketone, and 2-butanone, and aldehydes such as acetophenone, acetaldehyde, and pormaldehyde.
実施例２
バラニトロアニリン（ＰＮＡ、関東化学社製）及びジフ
ェニルエチレンジアミン（ＤＰＥＮ、関東化学社製）を
モル比（ＰＮＡ／ＤＰＥＮ比）０．１４で混合溶融させ
冷却固化させる際に固化が始まる過程で、結晶配向を揃
えさせたい方向に対し塗膜面内で垂直方向に機械的刺激
を加える。機械的刺激面に対し垂直方向に結晶が配向し
なから固化してゆくために高い配向性を持ったＳ ＨＧ
活性な非線形材料が得られることになる。この特性を活
かした応用例を第２図及び第３図に示も
第２図１ｉｓＨＧ素子としての光フアイバー型光波長変
換素子の概略図である。ＰＮＡとＤＰＥＮの混合溶融さ
せ冷却固化させた組成物からなるコア（１）がガラス等
のＳＨＧ不活性な媒質からなるクラッド（２）で被覆さ
れた構造を有している。混合溶融物をガラスキャピラリ
ー中に毛細管現象を利用して注入し キャピラリ一端に
機械的刺激を与えるとキャピラリーの長さ方向に結晶配
列が起こり高配向された高ＳＨＧ活性なＳＨＧ素子を得
られる。まＬ 第３図はＳＨＧ素子としてのスラブ型
光波長変換素子の概略図である。光フアイバー型同様に
基盤上に溶融させた混合溶融物を注入し 固化が始まる
過程で、素子の末端に機械的刺激を与えることでスラブ
型導波路の導波方向に結晶配列が進行し 高配向された
高ＳＨＧ活性なＳＨＧ素子を得られる。本発明におけへ
結晶配向性の高い物質とはジフェニルエチレンジアミ
ンなどの芳香族ジアミノアルカン類 液晶材料とじて用
いられヘ コレステロールアセテート、コレステロール
ベンゾエートなどのコレステロール系化合Ｉ１． Ｐ
−カルボキシフェニルＮ−アミルカルボネート、Ｐ−カ
ルボキシフェニルエチルカルボネートなどの炭酸エステ
ル類が挙げられる。Example 2 Process in which solidification begins when varanitroaniline (PNA, manufactured by Kanto Kagaku Co., Ltd.) and diphenylethylenediamine (DPEN, manufactured by Kanto Kagaku Co., Ltd.) are mixed and melted at a molar ratio (PNA/DPEN ratio) of 0.14, and solidified by cooling. Then, mechanical stimulation is applied in the direction perpendicular to the direction in which the crystal orientation is desired to be aligned within the surface of the coating film. SHG has high orientation because the crystals are not oriented in the direction perpendicular to the mechanical stimulus surface and solidify.
An active nonlinear material will be obtained. Application examples that take advantage of this characteristic are shown in FIGS. 2 and 3. FIG. 2 is a schematic diagram of an optical fiber type optical wavelength conversion element as an HG element. It has a structure in which a core (1) made of a mixed melted composition of PNA and DPEN, cooled and solidified, is covered with a cladding (2) made of an SHG-inactive medium such as glass. When the mixed melt is injected into a glass capillary using capillary action and mechanical stimulation is applied to one end of the capillary, crystal alignment occurs in the length direction of the capillary, resulting in a highly oriented SHG element with high SHG activity. Figure 3 is a schematic diagram of a slab type optical wavelength conversion element as an SHG element. Similar to the optical fiber type, a molten mixture is injected onto the substrate, and during the process of solidification, mechanical stimulation is applied to the end of the element, which causes the crystal alignment to progress in the waveguide direction of the slab type waveguide, resulting in highly oriented Thus, an SHG element with high SHG activity can be obtained. In the present invention, substances with high crystal orientation include aromatic diaminoalkanes such as diphenylethylenediamine; cholesterol-based compounds such as cholesterol acetate and cholesterol benzoate; P
-Carboxyphenyl N-amyl carbonate, P-carboxyphenylethyl carbonate, and other carbonate esters.
発明の効果
本発明によれば 単独ではＳＨＧ不活性となる結晶構造
をとる物質でも配向性の高い物質との混合結晶化によっ
て高配向性を持った高いＳＨＧを示す物質をえることが
可能となる。また その結晶化の特性から効率の良い光
波長変換素子の製造が可能となる。Effects of the Invention According to the present invention, even if a substance has a crystalline structure that is SHG-inactive when used alone, it is possible to obtain a substance exhibiting high SHG with high orientation through mixed crystallization with a highly oriented substance. . Moreover, its crystallization characteristics make it possible to manufacture highly efficient optical wavelength conversion elements.
第１図は本発明により製造されたＳ ＨＧ活性な組成物
のＳＨＧ強度を示ず阻 第２図は本発明により得られた
ＳＨＧ活性な組成物を用いた光フアイバー型光波長変換
素子を示す斜視図 第３図はスラブ型光波長変換素子を
示す斜視図である。
代理人の氏名 弁理士 粟野重孝 ほか１名第１図
第３図
ズラフ゛製光沢長文秋稟チ
Ｊ躊Ｗｊ九引零。
措（ｌｏｏ） ｐｐｙ＝ＮモＡ／亦学
（％）FIG. 1 shows the SHG intensity of the SHG-active composition produced according to the present invention. FIG. 2 shows an optical fiber type optical wavelength conversion device using the SHG-active composition obtained according to the present invention. Perspective View FIG. 3 is a perspective view showing a slab type optical wavelength conversion element. Name of agent: Patent attorney Shigetaka Awano and one other person. Measure (loo) ppy=NmoA/亦学(%)
Claims (4)
向方向を任意に揃えられる有機化合物とを少なくとも２
種以上混合溶融し、冷却固化させることにより得られた
非線形光学材料。(1) At least two organic compounds exhibiting second-order nonlinear optical properties and an organic compound whose crystal orientation can be arbitrarily aligned.
A nonlinear optical material obtained by mixing and melting two or more species, cooling and solidifying.
与性（ドナー性）及び電子吸引性（アクセプター性）の
置換基を備えたπ電子共役系有機化合物であることを特
徴とする請求項１に記載の非線形光学材料。(2) A claim characterized in that the organic compound exhibiting second-order nonlinear optical properties is a π-electron conjugated organic compound having substituents with electron-donating properties (donor properties) and electron-withdrawing properties (acceptor properties). 1. The nonlinear optical material according to 1.
の１種がジフェニルエチレンジアミンであることを特徴
とする請求項１に記載の非線形光学材料。(3) The nonlinear optical material according to claim 1, wherein one of the organic compounds whose crystal orientation can be arbitrarily aligned is diphenylethylenediamine.
結晶配向を揃えることができる有機化合物とを少なくと
も２種以上混合溶融し、冷却固化させる過程において、
電気的・熱的あるいは機械的刺激を与えることで結晶配
向方向を任意に揃えることを特徴とする請求項１に記載
の非線形光学材料を用いた非線形光学素子の製造方法。(4) In the process of mixing and melting at least two organic compounds exhibiting second-order nonlinear optical properties and an organic compound whose crystal orientation can be arbitrarily aligned, and cooling and solidifying the mixture.
2. A method for manufacturing a nonlinear optical element using the nonlinear optical material according to claim 1, wherein the crystal orientation direction is arbitrarily aligned by applying electrical, thermal, or mechanical stimulation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1122186A JP2650418B2 (en) | 1989-05-16 | 1989-05-16 | Nonlinear optical material and manufacturing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1122186A JP2650418B2 (en) | 1989-05-16 | 1989-05-16 | Nonlinear optical material and manufacturing method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02301728A true JPH02301728A (en) | 1990-12-13 |
| JP2650418B2 JP2650418B2 (en) | 1997-09-03 |
Family
ID=14829705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1122186A Expired - Lifetime JP2650418B2 (en) | 1989-05-16 | 1989-05-16 | Nonlinear optical material and manufacturing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2650418B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62161131A (en) * | 1986-01-10 | 1987-07-17 | Toray Ind Inc | Organic nonlinear optical material and its preparation |
| JPS6413122A (en) * | 1987-07-06 | 1989-01-18 | Sumitomo Electric Industries | Optical wavelength converting element |
-
1989
- 1989-05-16 JP JP1122186A patent/JP2650418B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62161131A (en) * | 1986-01-10 | 1987-07-17 | Toray Ind Inc | Organic nonlinear optical material and its preparation |
| JPS6413122A (en) * | 1987-07-06 | 1989-01-18 | Sumitomo Electric Industries | Optical wavelength converting element |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2650418B2 (en) | 1997-09-03 |
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