JP2001233872A - Asymmetric liquid crystalline charge transport material having terthiophene skeleton - Google Patents
Asymmetric liquid crystalline charge transport material having terthiophene skeletonInfo
- Publication number
- JP2001233872A JP2001233872A JP2000051876A JP2000051876A JP2001233872A JP 2001233872 A JP2001233872 A JP 2001233872A JP 2000051876 A JP2000051876 A JP 2000051876A JP 2000051876 A JP2000051876 A JP 2000051876A JP 2001233872 A JP2001233872 A JP 2001233872A
- Authority
- JP
- Japan
- Prior art keywords
- group
- charge transport
- liquid crystalline
- material according
- liquid crystal
- 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
- 239000000463 material Substances 0.000 title claims abstract description 80
- 239000007788 liquid Substances 0.000 title claims abstract description 36
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical group C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 239000004973 liquid crystal related substance Substances 0.000 claims description 43
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000002178 crystalline material Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 39
- 239000000126 substance Substances 0.000 description 18
- 239000000758 substrate Substances 0.000 description 15
- 230000005684 electric field Effects 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000001052 transient effect Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- -1 For example Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 210000000208 hepatic perisinusoidal cell Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- WHJKVPBAKQHFPP-UHFFFAOYSA-N 2-dodecoxy-6-(4-octylphenyl)naphthalene Chemical compound C1=CC2=CC(OCCCCCCCCCCCC)=CC=C2C=C1C1=CC=C(CCCCCCCC)C=C1 WHJKVPBAKQHFPP-UHFFFAOYSA-N 0.000 description 1
- RFVVRPOXDSLRNM-UHFFFAOYSA-N 3,4-dioctyl-2-(3-thiophen-2-ylthiophen-2-yl)thiophene Chemical compound C(CCCCCCC)C=1C(=C(SC=1)C=1SC=CC=1C=1SC=CC=1)CCCCCCCC RFVVRPOXDSLRNM-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical class C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、液晶性とともに正
孔および／または電子輸送性を有する液晶性電荷輸送材
料、およびこの液晶性電荷輸送材料を使用した各種素子
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal charge transporting material having a liquid crystallinity and a hole and / or electron transporting property, and various devices using the liquid crystal charge transporting material.
【０００２】[0002]
【従来の技術】従来、電荷輸送材料のうち均一・大面積
適用性を有するものとしては、電荷を輸送するサイトと
なる電荷輸送性分子を、ポリカーボネート樹脂等のマト
リックス材料中に溶解あるいは分散させた材料や、ポリ
ビニルカルバゾール等のようにポリマー主鎖に電荷輸送
性分子構造をペンダントさせた材料が知られている。こ
れらの材料は、複写機やプリンター等の感光体の材料と
して広く使用されている。2. Description of the Related Art Conventionally, as a charge transporting material having uniformity and large area applicability, a charge transporting molecule serving as a site for transporting a charge is dissolved or dispersed in a matrix material such as a polycarbonate resin. Materials and materials in which a charge transporting molecular structure is pendant on a polymer main chain, such as polyvinyl carbazole, are known. These materials are widely used as materials for photoconductors such as copiers and printers.
【０００３】このうち、分散型の電荷輸送材料において
は、電荷輸送性能を向上させるために電荷輸送分子をマ
トリックスであるポリマーに高濃度で溶解させることが
望ましいが、高濃度にすると実際には電荷輸送分子がマ
トリックスにおいて結晶化してしまうため、電荷輸送分
子の濃度は、一般的には２０〜５０重量%の濃度が限界
である。その結果、全体の５０重量%以上が電荷輸送性
のないマトリックスが占めることになり、マトリックス
によって電荷輸送性や応答速度が制限されるという問題
がある。[0003] Among these, in a dispersion type charge transporting material, it is desirable to dissolve charge transporting molecules in a polymer as a matrix at a high concentration in order to improve charge transporting performance. Since the transport molecules are crystallized in the matrix, the concentration of the charge transport molecules is generally limited to a concentration of 20 to 50% by weight. As a result, 50% by weight or more of the entire matrix is occupied by the matrix having no charge transporting property, and there is a problem that the charge transporting property and response speed are limited by the matrix.
【０００４】一方、ペンダント型の電荷輸送性ポリマー
の場合には、電荷輸送性を有するペンダントの占める割
合が高くなるが、成膜した場合の膜の機械的強度、環境
安定性、耐久性、成膜性等の点で実用上の問題が多い。
また、この種の電荷輸送材料は、電荷輸送性ペンダント
が局所的に近接配置をとるために、このような局所近接
部分が電荷をホッピングする際に安定サイトとなり、一
種のトラップとして作用するために、電荷の移動度を低
下させるという問題がある。On the other hand, in the case of the pendant type charge transporting polymer, the proportion of the pendant having the charge transporting property is high, but the mechanical strength, environmental stability, durability, and durability of the formed film are high. There are many practical problems in terms of film properties and the like.
In addition, since this kind of charge transporting material has a locally close arrangement of the charge transporting pendant, such a locally adjacent portion becomes a stable site when hopping charges, and acts as a kind of trap. In addition, there is a problem that the mobility of charges is reduced.
【０００５】また、前記分散型およびペンダント型を含
めアモルファス材料系の電荷輸送材料は、ホッピングサ
イトが空間的にばかりでなく、エネルギー的にも揺らぎ
を有するという問題が存在する。そのために電荷輸送は
電荷輸送サイトの濃度に大きく依存し、またその移動度
は一般に１×１０−６〜１×１０−５ｃｍ２／Ｖｓ程度
であり、分子性結晶の０．１〜１ｃｍ２／Ｖｓに比較し
て著しく小さい点で問題である。さらにアモルファス材
料系の電荷輸送材料には電荷の輸送特性に対して強い温
度依存性や電界強度依存性があるという問題がある。一
方、結晶性の電荷輸送材料はこれらの点においては優れ
ているが、均一・大面積適用性に欠ける問題点がある。In addition, amorphous charge transport materials including the dispersion type and the pendant type have a problem that hopping sites fluctuate not only spatially but also energy. As charge transport in order largely depends on the concentration of the charge transport sites, also its mobility is generally 1 × 10 -6 ~1 × about 10 -5 cm 2 / Vs, 0.1~1cm 2 of molecular crystals This is a problem in that it is significantly smaller than / Vs. Further, there is a problem that the charge transporting material of the amorphous material type has a strong temperature dependence and electric field intensity dependence on the charge transporting property. On the other hand, a crystalline charge transporting material is excellent in these respects, but has a problem that it lacks uniformity and large area applicability.
【０００６】このような、結晶性の電荷輸送材料の特徴
と均一・大面積適用性を兼ね備えるものとして、多結晶
の電荷輸送材料が期待されているが、多結晶材料はミク
ロ的には本質的に不均一な材料であって、例えば、粒子
界面に形成される欠陥を抑制する必要がある等の課題が
あり、実用化には問題がある。A polycrystalline charge transporting material is expected to combine such characteristics of a crystalline charge transporting material with uniform and large area applicability, but polycrystalline materials are essentially microscopic. However, there is a problem that it is necessary to suppress defects formed at the particle interface, and there is a problem in practical use.
【０００７】[0007]
【発明が解決しようとする課題】本発明は上記の課題を
解決しようとするものであって、本発明の目的は、構造
柔軟性と大面積にわたる均一性を有するアモルファス材
料の利点と、優れた電荷輸送特性を有する結晶性材料の
利点を同時に有し、高品位の電荷輸送性、薄層形成性、
各種耐久性等に優れた新規な電荷輸送材料を提供するこ
とである。SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and an object of the present invention is to provide an advantage of an amorphous material having structural flexibility and uniformity over a large area. At the same time, it has the advantages of crystalline materials with charge transport properties, high-quality charge transport properties,
An object of the present invention is to provide a novel charge transporting material having excellent durability and the like.
【０００８】[0008]
【課題を解決するための手段】本発明者らは電荷輸送材
料として液晶性物質に着目したところ、液晶性物質によ
って、バンドライクな輸送特性が実現し、このために従
来の分子分散系材料に比べて大きな移動度が実現でき、
更にその電界依存性がみられないという優れた電荷輸送
特性と、均一・大面積適用性があらわれることを見出し
た。Means for Solving the Problems The inventors of the present invention focused on a liquid crystal material as a charge transporting material, and realized a band-like transport characteristic by the liquid crystal material. Greater mobility can be realized,
Further, they have found that excellent charge transporting properties, in which the electric field dependence is not observed, and applicability to a uniform and large area appear.
【０００９】本発明者らはこのような液晶性電荷輸送材
料につき特許出願を行ったが（特願平１０−７６８２０
号参照）、さらに本発明者らは、ターチオフェン骨格を
有し、そのターチオフェン骨格の左右に炭素数が異なる
基を結合させた非対称液晶性物質が電荷輸送材料として
有用であることを見出し本発明を完成させた。The present inventors have filed a patent application for such a liquid crystalline charge transport material (Japanese Patent Application No. 10-76820).
In addition, the present inventors have found that an asymmetric liquid crystal substance having a terthiophene skeleton and having groups having different carbon numbers bonded to the left and right of the terthiophene skeleton is useful as a charge transport material. Completed the invention.
【００１０】したがって、本発明の液晶性電荷輸送材料
は下記一般式Accordingly, the liquid crystalline charge transporting material of the present invention has the following general formula:
【化３】 （ただし、Ｌ基および／またはＲ基は炭素原子を含む基
であって、Ｌ基の炭素数とＲ基の炭素数が異なる）を有
する非対称液晶性物質を含んでなることを特徴とするも
のである。Embedded image (Wherein the L group and / or the R group is a group containing a carbon atom, and the number of carbons of the L group and the number of carbons of the R group are different). It is.
【００１１】[0011]
【発明の実施の形態】非対称液晶性物質 本発明の液晶性電荷輸送材料は、ターチオフェン骨格の
左右に炭素数が異なる基を結合させた非対称液晶性物質
を含むことを特徴としている。この非対称液晶性物質は
一般式BEST MODE FOR CARRYING OUT THE INVENTION Asymmetric Liquid Crystalline Substance The liquid crystalline charge transporting material of the present invention is characterized in that it contains an asymmetric liquid crystal substance in which groups having different carbon numbers are bonded to the left and right of a terthiophene skeleton. This asymmetric liquid crystalline substance has the general formula
【化４】 （ただし、Ｌ基および／またはＲ基は炭素原子を含む基
であって、Ｌ基の炭素数とＲ基の炭素数が異なる）で表
すことができる。本発明において好ましい非対称液晶性
物質は、Ｌ基およびＲ基にカルボニル基を含まないもの
であり、さらに好ましくは、Ｌ基およびＲ基に酸素原子
を含まないものであり、特に好ましくはＬ基およびＲ基
がアルキル基、例えば直鎖アルキル基であるものであ
る。Embedded image (However, the L group and / or R group is a group containing a carbon atom, and the number of carbon atoms of the L group and the number of carbon atoms of the R group are different). Preferred asymmetric liquid crystalline substances in the present invention do not contain a carbonyl group in the L group and the R group, more preferably do not contain an oxygen atom in the L group and the R group, particularly preferably the L group and the R group. The R group is an alkyl group, for example, a linear alkyl group.
【００１２】本発明の非対称液晶性物質のＬおよびＲの
炭素数は、炭素の少ない基が１〜１７個、多い基が例え
ば２〜１８個、炭素数の差は１以上であることができ
る。The number of carbon atoms of L and R of the asymmetric liquid crystalline substance of the present invention can be 1 to 17 groups having a small number of carbon atoms, for example 2 to 18 groups having a large number of carbon atoms, and the difference in the number of carbon atoms can be 1 or more. .
【００１３】本発明に用いるのに好適な非対称液晶性物
質としては、例えば、以下に示すＬ基とＲ基を有するも
のが挙げられる。The asymmetric liquid crystalline substance suitable for use in the present invention includes, for example, those having the following L and R groups.
【００１４】 Ｌ基 Ｒ基 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ6Ｈ13 Ｃ3Ｈ7 Ｃ12Ｈ25 Ｃ5Ｈ11 Ｃ8Ｈ17 Ｃ5Ｈ11 Ｃ10Ｈ21 Ｃ5Ｈ11 Ｃ14Ｈ29 Ｃ6Ｈ13 Ｃ8Ｈ17 Ｃ6Ｈ13 Ｃ12Ｈ25 Ｃ6Ｈ13 Ｃ15Ｈ31 Ｃ6Ｈ13 Ｃ18Ｈ37 Ｃ8Ｈ15 Ｃ９Ｈ19 Ｃ8Ｈ15 Ｃ16Ｈ33 Ｃ8Ｈ15 Ｃ18Ｈ37 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ18Ｈ37 Ｃ14Ｈ29 Ｃ16Ｈ33 Ｃ14Ｈ29 Ｃ18Ｈ37 Ｃ17Ｈ35 Ｃ18Ｈ37 このような非対称液晶性物質は、通常対称なものと比べ
結晶性が低いために高純度のものを得られるのが困難で
あると考えられているが、本発明の非対称液晶性物質
は、このような問題なく高純度のものを得ることができ
る。 L group R group CH 3 C 2 H 5 C 3 H 7 C 6 H 13 C 3 H 7 C 12 H 25 C 5 H 11 C 8 H 17 C 5 H 11 C 10 H 21 C 5 H 11 C 14 H 29 C 6 H 13 C 8 H 17 C 6 H 13 C 12 H 25 C 6 H 13 C 15 H 31 C 6 H 13 C 18 H 37 C 8 H 15 C 9 H 19 C 8 H 15 C 16 H 33 C 8 H 15 C 18 H 37 C 10 H 21 C 12 H 25 C 10 H 21 C 18 H 37 C 14 H 29 C 16 H 33 C 14 H 29 C 18 H 37 C 17 H 35 C 18 H 37 Such an asymmetric liquid crystal substance is generally considered to be difficult to obtain a high-purity substance because of lower crystallinity than a symmetric substance. A high-purity product can be obtained without such a problem.
【００１５】また、本発明の液晶性物質自体の電荷移動
度としては、電子移動度および正孔移動度ともに、好ま
しくは１×１０−５ｃｍ２／Ｖｓ以上である。電荷移動
度が１×１０−５ｃｍ２／Ｖｓより小さいと、素子にし
た場合応答速度が低下する可能性がある。The charge mobility of the liquid crystalline substance itself of the present invention is preferably not less than 1 × 10 −5 cm 2 / Vs for both electron mobility and hole mobility. When the charge mobility is smaller than 1 × 10 −5 cm 2 / Vs, there is a possibility that the response speed is reduced when the device is used.
【００１６】液晶性電荷輸送材料 本発明の液晶性電荷輸送材料は、非対称液晶性物質単独
でもよいが、非対称液晶性物質の他に、例えばバインダ
ーを含ませて膜形成機能を付与することができる。この
場合、バインダー１００重量部あたり液晶性物質を約１
０〜１００重量部、好ましくは３０〜８０重量部とで
き、液晶性物質の量が少なすぎると目的とする電荷輸送
性を有する高分子膜が得られず、一方、液晶性物質の量
が多すぎると成膜性が低下する。 Liquid Crystalline Charge Transporting Material The liquid crystalline charge transporting material of the present invention may be an asymmetric liquid crystal substance alone, but may be provided with a film-forming function by, for example, including a binder in addition to the asymmetric liquid crystal substance. . In this case, about 1 part by weight of the liquid crystal material per 100 parts by weight of the binder is used.
The amount can be 0 to 100 parts by weight, preferably 30 to 80 parts by weight. If the amount of the liquid crystal substance is too small, a polymer film having the intended charge transporting property cannot be obtained. If it is too much, the film formability will be reduced.
【００１７】また、本発明の液晶性電荷輸送材料は電子
移動度が１×１０−５ｃｍ２／Ｖｓ以上が好ましく、ま
た、正孔移動度は１×１０−５ｃｍ２／Ｖｓ以上が好ま
しい。The liquid crystal charge transporting material of the present invention preferably has an electron mobility of 1 × 10 −5 cm 2 / Vs or more, and a hole mobility of 1 × 10 −5 cm 2 / Vs or more. .
【００１８】素子、装置 本発明の液晶性電荷輸送材料は、例えば光センサー、エ
レクトロルミネッセンス素子、光導電体、空間変調素
子、薄膜トランジスター、温度センサー、画像表示素子
等の種々の用途に有用である。本発明の液晶性電荷輸送
材料は、高速な移動度と構造的なトラップの形成が抑制
されることから、まず第一の応用として、高速応答性の
光センサーが挙げられる。次に電荷輸送性能に優れるこ
とからエレクトロルミネッセンス素子の電荷輸送層とし
て使用でき、この場合、偏光発光性エレクトロルミネッ
センス素子とすることもできる。また、電場配向性と光
導電性とが同時にスイッチングできることから、画像表
示素子に用いることが可能である。更に、本発明の材料
は液晶性を有し、各相が温度によって異なる電荷移動度
を示し、光導電性も異なることから温度と光とで同時に
スイッチングできる、従来とは異なった温度センサーと
して使用できる。 Elements and Apparatus The liquid crystalline charge transporting material of the present invention is useful for various uses such as, for example, optical sensors, electroluminescent elements, photoconductors, spatial modulation elements, thin film transistors, temperature sensors, and image display elements. . Since the liquid crystal charge transporting material of the present invention suppresses the formation of high-speed mobility and structural traps, a first application is a high-speed responsive optical sensor. Next, since it has excellent charge transporting performance, it can be used as a charge transporting layer of an electroluminescent device. In this case, a polarized light emitting electroluminescent device can also be used. Further, since the electric field orientation and the photoconductivity can be switched at the same time, it can be used for an image display device. Furthermore, the material of the present invention has a liquid crystal property, each phase exhibits different charge mobility depending on temperature, and also has different photoconductivity, so that it can be simultaneously switched between temperature and light, and is used as a different temperature sensor from the past. it can.
【００１９】図１は、画像表示素子への応用例を説明す
る図である。画像表示素子においてはガラス等の基板１
５’、ＩＴＯ（インジウムスズオキサイド）等の電極１
３’、露光に応じてキャリアを発生する電荷発生層１
４’、本発明の液晶性電荷輸送層１４、対向電極(金電
極等)１３’を順次積層した素子に、図１の下部から画
像露光(入力画像)とすると、露光に応じて液晶性電荷輸
送材料が配向して対向電極(金電極)にキャリアが流れ
る。この液晶の配向を光学的に読みとることによって入
力画像を再生することができる。上記液晶のスメクティ
ック性が大きければ液晶の配向は長時間保存されて入力
情報が長時間保存されることとなる。FIG. 1 is a diagram for explaining an example of application to an image display device. In an image display device, a substrate 1 such as glass
5 ', electrode 1 of ITO (indium tin oxide) or the like
3 ′, charge generation layer 1 that generates carriers in response to exposure
When an image exposure (input image) is performed from the bottom of FIG. 1 on a device in which a liquid crystal charge transport layer 14 of the present invention and a counter electrode (such as a gold electrode) 13 ′ are sequentially laminated, the liquid crystal charge is changed according to the exposure. The transport material is oriented and carriers flow to the counter electrode (gold electrode). By optically reading the orientation of the liquid crystal, an input image can be reproduced. If the smecticity of the liquid crystal is large, the orientation of the liquid crystal is stored for a long time, and the input information is stored for a long time.
【００２０】図２、３および４は、画像記録装置の電荷
輸送層に本発明の液晶性電荷輸送材料を適用した例を説
明する図である。図２は光センサーの概略断面図であ
り、基板１５’上に電極１３’、電荷発生層１４’液晶
性電荷輸送層１４が順次積層されており、電荷輸送層に
本発明の液晶性電荷輸送材料を使用した例である。図３
においては、図２の液晶性電荷輸送層１４上にさらに保
護層１６が設けられている。使用方法を更に詳しく説明
すると、図４に示すように上下の電極１３’、対向電極
１３’に電圧を印加しつつ、図面上部よりパターン露光
を行なう。電荷発生層１４’においてパターン状にキャ
リアが発生し、液晶性電荷輸送層１４により輸送された
電荷が、スペーサー１８を介して設けた空間１９におい
て放電し、情報記録層１１の表面に達する。なお１５’
は基板である。情報記録層１１は例えばスメクティック
液晶と高分子の複合体からなる液晶高分子複合体層であ
り、蓄積された電荷による電界で液晶がパターン状に配
向し、蓄積され、光学的読み取りを行なうことができ
る。FIGS. 2, 3 and 4 are diagrams illustrating examples in which the liquid crystal charge transport material of the present invention is applied to the charge transport layer of an image recording apparatus. FIG. 2 is a schematic sectional view of an optical sensor, in which an electrode 13 'and a charge generation layer 14' and a liquid crystal charge transport layer 14 are sequentially laminated on a substrate 15 '. This is an example using materials. FIG.
In FIG. 2, a protective layer 16 is further provided on the liquid crystalline charge transport layer 14 of FIG. The method of use will be described in more detail. As shown in FIG. 4, pattern exposure is performed from the upper part of the drawing while applying a voltage to the upper and lower electrodes 13 'and the counter electrode 13'. Carriers are generated in a pattern in the charge generation layer 14 ′, and the charges transported by the liquid crystal charge transport layer 14 are discharged in the space 19 provided via the spacer 18 and reach the surface of the information recording layer 11. 15 '
Is a substrate. The information recording layer 11 is, for example, a liquid crystal polymer composite layer composed of a composite of a smectic liquid crystal and a polymer, and the liquid crystal is oriented in a pattern by an electric field due to the stored electric charges, is stored, and can perform optical reading. it can.
【００２１】図５は、画像記録装置の別の例を示す概略
断面図であり、順次基板１５’、対向電極１３’、情報
記録層１１、誘電体層２０、液晶性電荷輸送層１４、電
荷発生層１４’、電極１３’、基板１５’が積層されて
いる。図４の場合と同様に電圧印加露光を行なうと発生
した電荷(像)は誘電体層２０の上部表面に蓄積され、図
４の場合と同様に蓄積された電荷による電界で液晶がパ
ターン状に配向し、蓄積され、光学的読み取りを行なう
ことができる。FIG. 5 is a schematic cross-sectional view showing another example of the image recording apparatus, in which a substrate 15 ', a counter electrode 13', an information recording layer 11, a dielectric layer 20, a liquid crystal charge transport layer 14, a charge The generation layer 14 ', the electrode 13', and the substrate 15 'are laminated. The charges (images) generated when voltage application exposure is performed in the same manner as in FIG. 4 are accumulated on the upper surface of the dielectric layer 20, and the liquid crystal is patterned in an electric field by the accumulated charges as in FIG. It can be oriented, stored and optically read.
【００２２】図６は空間光変調素子に本発明の液晶性電
荷輸送材料を用いた例であり、光照射５４側から順に、
ガラス板５１、透明電極１３、液晶層５３、ガラス板５
１、偏光フィルム５２、液晶性電荷輸送層１４、電荷発
生層１４’、透明電極１３が積層されている。FIG. 6 shows an example in which the liquid crystal charge transporting material of the present invention is used for a spatial light modulator.
Glass plate 51, transparent electrode 13, liquid crystal layer 53, glass plate 5
1, a polarizing film 52, a liquid crystal charge transport layer 14, a charge generation layer 14 ', and a transparent electrode 13 are laminated.
【００２３】また、本発明の液晶性電荷輸送材料は、薄
膜トランジスターの活性層として用いることも可能であ
る。例えば、図７に示すように、ソース電極６１、ドレ
イン６２、ゲート電極６３の各電極とゲート誘電体層６
５を配置した基板６４に上記液晶材料を配置して用いる
ことができる。Further, the liquid crystalline charge transporting material of the present invention can be used as an active layer of a thin film transistor. For example, as shown in FIG. 7, each electrode of a source electrode 61, a drain 62, and a gate electrode 63 and the gate dielectric layer 6
The liquid crystal material described above can be disposed on the substrate 64 on which the substrate 5 is disposed.
【００２４】図８〜１１はエレクトロルミネッセンス素
子への応用例を説明する図である。エレクトロルミネッ
センス素子の最も簡単な構造は図８に示したように、発
光層７１あるいは液晶性電荷輸送層１４をスペーサー１
８を介して陰極と陽極それぞれ１３’および１３’で挟
み透明基板７１で保持したものである。強い発光を得る
ためには、電子注入の役割を果たす陰極材料は仕事関数
の小さいもの、陽極材料は逆に仕事関数の値が陰極と同
じ値またはより大きなものを選択することが好ましい。FIGS. 8 to 11 are views for explaining an example of application to an electroluminescent element. As shown in FIG. 8, the simplest structure of the electroluminescence element is to form the light emitting layer 71 or the liquid crystal charge transport layer 14 with the spacer 1.
The cathode and anode are sandwiched by 13 ′ and 13 ′, respectively, and are held by a transparent substrate 71 via the transparent substrate 71. In order to obtain strong light emission, it is preferable to select a cathode material that plays a role of electron injection with a small work function, and conversely, an anode material with a work function value equal to or larger than that of the cathode.
【００２５】陽極材料としては、一般的に例えば、ＩＴ
Ｏ、酸化インジウム、酸化錫(アンチモン、砒素、また
はフッ素ドープ)、Ｃｄ２ＳｎＯ４、酸化亜鉛、ヨウ化
銅、または金等の透明または半透明電極材料が挙げら
れ、また、陰極材料としては、例えば、アルカリ金属ま
たはアルカリ土類金属を基本とするナトリウム、カリウ
ム、マグネシウム、リチウム、ナトリウム−カリウム合
金、マグネシウム−インジウム合金、マグネシウム−銀
合金、アルミニウム、金、銀、ガリウム、インジウム、
銅等、更に陽極に使用した材料と同一のものが挙げられ
る。As the anode material, generally, for example, IT
O, indium oxide, tin oxide (antimony, arsenic, or fluorine-doped), Cd 2 SnO 4 , zinc oxide, copper iodide, or a transparent or translucent electrode material such as gold, and as the cathode material, For example, sodium, potassium, magnesium, lithium, sodium-potassium alloy, magnesium-indium alloy, magnesium-silver alloy, aluminum, gold, silver, gallium, indium, based on alkali metals or alkaline earth metals,
The same material as that used for the anode, such as copper, may be used.
【００２６】発光層に用いる材料は、本発明の液晶性電
荷輸送材料と発光材料とからなる。液晶性電荷輸送材料
は、電子及び正孔両輸送性材料または両輸送性材料の混
合物、若しくは電子輸送性材料と正孔輸送性材料の混合
物が好ましいが、電極界面での発光を利用する場合には
一方の輸送性材料だけでもよい。また、液晶自身が蛍光
を持つ場合には、発光材料は特に必要としない。液晶の
コア部分が固体状態で強い蛍光を持つ有機色素類から構
成される場合の多くが上記条件に該当する。The material used for the light emitting layer comprises the liquid crystalline charge transporting material of the present invention and a light emitting material. The liquid crystal charge transporting material is preferably an electron and hole transporting material or a mixture of both transporting materials, or a mixture of an electron transporting material and a hole transporting material. May be only one transportable material. When the liquid crystal itself has fluorescence, no light-emitting material is required. In many cases, the above condition is satisfied when the core portion of the liquid crystal is composed of organic dyes having strong fluorescence in a solid state.
【００２７】発光材料としては、蛍光量子収率の高い色
素材料を利用する。例えば、ジフェニルエチレン誘導
体、トリフェニルアミン誘導体、ジアミノカルバゾール
誘導体、ビススチリル誘導体、ベンゾチアゾール誘導
体、ベンゾオキサゾール誘導体、芳香族ジアミン誘導
体、キナクリドン系化合物、ペリレン系化合物、オキサ
ジアゾール誘導体、クマリン系化合物、アントラキノン
誘導体、またはＤＣＭ−１等のレーザ発振用色素等が挙
げられ、本発明の液晶性電荷輸送材料の液晶性を壊さな
い程度に、好ましくは本発明の液晶性電荷輸送材料に対
して約０．０１〜３０%添加する。また、図１０および
１１に示したような層構成とした場合には、発光層(発
光材料)の厚みは電子または正孔の移動を妨げない程度
とする。発光層の膜厚は、好ましくは０．２〜１５μm
とし、材料中ヘスペーサ粒子の散布、あるいはセルの周
囲に設ける封止剤で膜厚を調整することができる。As the light emitting material, a dye material having a high fluorescence quantum yield is used. For example, diphenylethylene derivatives, triphenylamine derivatives, diaminocarbazole derivatives, bisstyryl derivatives, benzothiazole derivatives, benzoxazole derivatives, aromatic diamine derivatives, quinacridone compounds, perylene compounds, oxadiazole derivatives, coumarin compounds, anthraquinone derivatives Or a dye for laser oscillation such as DCM-1 and the like, and to the extent that the liquid crystallinity of the liquid crystalline charge transporting material of the present invention is not destroyed, preferably about 0.01 to the liquid crystalline charge transporting material of the present invention. Add ~ 30%. In the case of the layer configuration shown in FIGS. 10 and 11, the thickness of the light-emitting layer (light-emitting material) is set to a value that does not hinder the movement of electrons or holes. The thickness of the light emitting layer is preferably 0.2 to 15 μm
The thickness can be adjusted by scattering spacer particles in the material or by using a sealing agent provided around the cell.
【００２８】図１２は、温度センサーヘの応用例を説明
する図である。温度センサーの構成は、電極１３、１
３’の間に本発明の液晶性電荷輸送層１４をスペーサー
１８を介して挟んだ構造が挙げられる。温度センサーと
して利用し得る性質としては、電荷移動度の温度変化、
導伝率の温度変化、光照射時における導伝率の温度変
化、および光透過性の温度変化等が利用できる。但し、
温度センサーとして光照射を併用する場合には、電極材
料および基材は透明性が必要であり、図１２では透明基
板１５を用いている。FIG. 12 is a diagram for explaining an application example to a temperature sensor. The configuration of the temperature sensor is as follows.
A structure in which the liquid crystalline charge transport layer 14 of the present invention is sandwiched between 3 'with a spacer 18 interposed therebetween. Properties that can be used as a temperature sensor include charge mobility temperature change,
A change in conductivity, a change in conductivity during light irradiation, a change in light transmittance, and the like can be used. However,
When light irradiation is also used as a temperature sensor, the electrode material and the base material need to be transparent, and a transparent substrate 15 is used in FIG.
【００２９】図１３および図１４は光センサーヘの応用
例を説明する図である。光センサーの構成は、電極１
３’，１３’の間に本発明の液晶性電荷輸送層１４をス
ペーサー１８を介して挟み、透明基板１５あるいは基板
１５’で保持した構造が挙げられる。光センサーとして
利用し得る性質としては、光照射による電流値の変化が
利用できる。FIGS. 13 and 14 are diagrams for explaining an application example to an optical sensor. The configuration of the optical sensor is electrode 1
A structure in which the liquid crystalline charge transport layer 14 of the present invention is sandwiched between 3 ′ and 13 ′ via a spacer 18 and held by the transparent substrate 15 or the substrate 15 ′. As a property that can be used as an optical sensor, a change in current value due to light irradiation can be used.
【００３０】[0030]
【実施例】以下、本発明の実施例を具体例を挙げて説明
する。The embodiments of the present invention will be described below with reference to specific examples.
【００３１】実施例１ （液晶性物質の調製）本実施例においては、以下の式で
表される２−ヘキシル−５”−ドデシルターチオフェン
を液晶性物質として用いた。 Example 1 (Preparation of liquid crystalline substance) In this example, 2-hexyl-5 "-dodecyl terthiophene represented by the following formula was used as a liquid crystalline substance.
【００３２】[0032]
【化５】 （以下、この液晶性物質を、炭素数６個のアルキルとタ
ーチオフェン骨格と炭素数１２個のアルキルが結合して
いることから、６−ｔｔｐ−１２と記載する）この６−
ｔｔｐ−１２は、例えば以下のような反応経路で合成す
ることができる。Embedded image (Hereinafter, this liquid crystalline substance is referred to as 6-ttp-12 because alkyl having 6 carbon atoms, terthiophene skeleton and alkyl having 12 carbon atoms are bonded.)
ttp-12 can be synthesized, for example, by the following reaction pathway.
【００３３】[0033]
【化６】 （液晶温度範囲）この６−ｔｔｐ−１２は、偏光顕微鏡
による観察によれば等方相から８８℃でＳｍＣ相に転移
し、さらに７２℃で別のスメクティック相（ＳｍＦ相と
思われる）に転移し、５６℃でおそらく結晶相（別の高
次のスメクティック相である可能性もある）に転移す
る。Embedded image (Liquid crystal temperature range) According to observation with a polarizing microscope, this 6-ttp-12 transforms from an isotropic phase to an SmC phase at 88 ° C, and further to another smectic phase (supposed to be an SmF phase) at 72 ° C. At 56 ° C., possibly transforming into a crystalline phase, which may be another higher order smectic phase.
【００３４】（ＨＯＭＯ、ＬＵＭＯ値）また、６−ｔｔ
ｐ−１２のＨＯＭＯ、ＬＵＭＯ値は半経験的分子軌道計
算（ＡＭ１）によると、それぞれ−８．１２ｅＶ、−
０．８８ｅＶと推測され、室温での実測値がそれぞれ−
５．１ｅＶ、−２．１ｅＶと推測された。高いＨＯＭＯ
値、かつ低いＬＵＭＯ値のためキャリア注入が効率的に
進行し、エレクトロルミネッセンス素子の発光効率が高
まると推測される。(HOMO, LUMO values)
According to semi-empirical molecular orbital calculation (AM1), the HOMO and LUMO values of p-12 are -8.12 eV and -12, respectively.
It is estimated to be 0.88 eV, and the measured values at room temperature are-
It was estimated to be 5.1 eV and -2.1 eV. High HOMO
It is presumed that carrier injection proceeds efficiently due to the low value and low LUMO value, and the luminous efficiency of the electroluminescent element increases.
【００３５】（電荷移動度特性）前記液晶性物質の電荷
輸送特性（移動度の測定）をＴｉｍｅ−ｏｆ−Ｆｌｉｇ
ｈｔ（タイムオブフライト：ＴＯＦ）法を用いて測定し
た。この際の測定条件は、７０℃（ＳｍＦ層と思われ
る）、電極材料は陽極陰極のいずれもＩＴＯであり、電
極間距離１５μｍ、電極面積０．１６ｃｍ２ 、照射波
長３３７ｎｍで行った。(Charge Mobility Characteristics) The charge-transport characteristics (measurement of mobility) of the liquid crystalline substance were measured using a Time-of-Frig
ht (Time of Flight: TOF). The measurement conditions were as follows: 70 ° C. (supposed to be an SmF layer); the electrode material was ITO for both the anode and cathode; the distance between the electrodes was 15 μm, the electrode area was 0.16 cm 2 , and the irradiation wavelength was 337 nm.
【００３６】高次のスメクティック相（７０℃における
ＳｍＦ相と推測される相）において正孔および電子両方
の電荷輸送（両極性の電荷輸送）が起こった。また、電
荷移動度は電界強度に依存せず、正孔移動度２．８×１
０−３ｃｍ２／Ｖｓ、電子移動度２．６×１０−３ｃｍ
２／Ｖｓという値が得られた。Both hole and electron charge transport (ambipolar charge transport) occurred in the higher smectic phase (presumed SmF phase at 70 ° C.). In addition, the charge mobility does not depend on the electric field intensity, and the hole mobility is 2.8 × 1
0 −3 cm 2 / Vs, electron mobility 2.6 × 10 −3 cm
A value of 2 / Vs was obtained.
【００３７】図１５にこの正孔移動度特性を測定する際
に得られた正バイアスの過渡光電流波形を、図１６に電
子移動度特性を測定する際に得られた逆バイアスの過渡
光電流波形を示す。FIG. 15 shows the transient photocurrent waveform of the positive bias obtained when measuring the hole mobility characteristics, and FIG. 16 shows the transient photocurrent of the reverse bias obtained when measuring the electron mobility characteristics. The waveform is shown.
【００３８】図１７に、電荷移動度の電界依存性を測定
した際のグラフを示す。このグラフからキャリア移動度
が電界強度に依存しないことが分かる。FIG. 17 shows a graph when the electric field dependence of the charge mobility is measured. From this graph, it can be seen that the carrier mobility does not depend on the electric field intensity.
【００３９】（発光特性）上記の６−ｔｔｐ−１２を用
いて色素を添加せずに電界発光を行った。液晶相におい
て（６５℃）、ＩＴＯ／ＩＴＯセルを用いた場合にも厚
さ２μｍの場合にわずか５０Ｖで目視可能な発光が見ら
れ、８０Ｖで発光強度は６０ｃｄ／ｍ２を超えた。電
流、発光強度は極めて安定しており、長時間安定した輝
度を維持できるものと思われる。また、発光スペクトル
は蛍光スペクトルに一致しており、６−ｔｔｐ−１２分
子上で電荷が再結合して発光していることが推認でき
た。また、Ａｌ／ＩＴＯセルにおいても発光が確認でき
た。(Emission Characteristics) Electroluminescence was performed using the above 6-ttp-12 without adding a dye. In the liquid crystal phase (65 ° C.), even when an ITO / ITO cell was used, visible light emission was observed only at 50 V when the thickness was 2 μm, and at 80 V, the emission intensity exceeded 60 cd / m 2 . The current and emission intensity are extremely stable, and it is considered that stable luminance can be maintained for a long time. In addition, the emission spectrum was consistent with the fluorescence spectrum, and it was confirmed that charges were recombined on the 6-ttp-12 molecule to emit light. Light emission was also confirmed in the Al / ITO cell.
【００４０】図１８に印加電圧に対する発光強度のグラ
フの一例を、図１９に波長毎の発光強度のグラフの一例
を、図２０に本実施例での印加電圧に対する発光強度の
グラフを示す。FIG. 18 shows an example of a graph of the luminous intensity with respect to the applied voltage, FIG. 19 shows an example of a graph of the luminous intensity for each wavelength, and FIG. 20 shows a graph of the luminous intensity with respect to the applied voltage in this embodiment.
【００４１】比較例１ ２−フェニルナフタレン誘導体（２−（４−オクチルフ
ェニル）−６−ドデシルオキシナフタレン）を用いて発
光特性を測定したところ、実施例１の場合と比べキャリ
ア注入のために高い電界（１５０Ｖ以上）が必要であ
り、また発光強度（２５０Ｖで０．７ｃｄ／ｍ２）も弱
かった。そのためこの材料を用いた場合は、実施例のも
のと比較して絶縁破壊を生じる確率が高いと思われる。COMPARATIVE EXAMPLE 1 The emission characteristics were measured using a 2-phenylnaphthalene derivative (2- (4-octylphenyl) -6-dodecyloxynaphthalene). An electric field (150 V or higher) was required, and the emission intensity (0.7 cd / m 2 at 250 V) was weak. Therefore, when this material is used, it is considered that the probability of causing dielectric breakdown is higher than that of the example.
【００４２】（ＨＯＭＯ、ＬＵＭＯ値）また、２−フェ
ニルナフタレン誘導体のＨＯＭＯ、ＬＵＭＯ値は半経験
的分子軌道計算（ＡＭ１）によると、それぞれ−８．３
８ｅＶ、−０．６０ｅＶと推測され、室温での実測値が
それぞれ−５．７ｅＶ、−１．８ｅＶと推測された。こ
れらは、実施例１と比較してエレクトロルミネッセンス
素子の発光効率が低くなることが推測される値であっ
た。(HOMO and LUMO values) The HOMO and LUMO values of the 2-phenylnaphthalene derivative were -8.3 each according to semiempirical molecular orbital calculation (AM1).
8 eV and -0.60 eV were estimated, and the measured values at room temperature were estimated to be -5.7 eV and -1.8 eV, respectively. These values were estimated to be lower in luminous efficiency of the electroluminescent device than in Example 1.
【００４３】比較例２ ジオクチルターチオフェン（８−ｔｔｐ−８）を用い８
０℃（ＳｍＦ相）で実施例１と同様に移動度を測定した
ところ、正孔移動度２．０×１０−３ｃｍ２／Ｖｓ、電
子移動度１．９×１０−３ｃｍ２／Ｖｓという実施例１
よりやや低い値が得られた。 Comparative Example 2 Using dioctyl terthiophene (8-ttp-8)
When the mobility was measured at 0 ° C. (SmF phase) in the same manner as in Example 1, the hole mobility was 2.0 × 10 −3 cm 2 / Vs, and the electron mobility was 1.9 × 10 −3 cm 2 / Vs. Example 1
Slightly lower values were obtained.
【００４４】[0044]
【発明の効果】本発明によって、構造柔軟性と大面積に
わたる均一性を有するアモルファス材料の利点と、優れ
た電荷輸送特性等を有する結晶性材料の利点を同時に有
し、高品位の電荷輸送性、薄層形成性、各種耐久性等に
優れた新規な電荷輸送材料を提供することができる。According to the present invention, the advantages of an amorphous material having structural flexibility and uniformity over a large area and the advantages of a crystalline material having excellent charge transport properties are simultaneously obtained, and high-quality charge transport properties are obtained. And a novel charge transporting material having excellent thin layer forming properties and various durability.
【００４５】また、本発明の材料においては、分子配向
による電荷移動度の異方性が期待でき、構造柔軟性であ
ることから外部刺激によってその配向を制御することも
可能である。Further, in the material of the present invention, anisotropy of charge mobility due to molecular orientation can be expected, and since the material is structurally flexible, its orientation can be controlled by an external stimulus.
【図１】画像表示素子の概略断面図である。FIG. 1 is a schematic sectional view of an image display device.
【図２】画像記録装置の概略断面図である。FIG. 2 is a schematic sectional view of the image recording apparatus.
【図３】画像記録装置の概略断面図である。FIG. 3 is a schematic sectional view of the image recording apparatus.
【図４】画像記録装置の概略断面図である。FIG. 4 is a schematic sectional view of the image recording apparatus.
【図５】画像記録装置の概略断面図である。FIG. 5 is a schematic sectional view of the image recording apparatus.
【図６】空間光変調素子の概略断面図である。FIG. 6 is a schematic sectional view of a spatial light modulator.
【図７】薄膜トランジスターの概略断面図である。FIG. 7 is a schematic sectional view of a thin film transistor.
【図８】エレクトロルミネッセンス素子の概略断面図で
ある。FIG. 8 is a schematic sectional view of an electroluminescent element.
【図９】エレクトロルミネッセンス素子の概略断面図で
ある。FIG. 9 is a schematic sectional view of an electroluminescent element.
【図１０】エレクトロルミネッセンス素子の概略断面図
である。FIG. 10 is a schematic sectional view of an electroluminescence element.
【図１１】エレクトロルミネッセンス素子の概略断面図
である。FIG. 11 is a schematic sectional view of an electroluminescent element.
【図１２】温度センサーの概略断面図である。FIG. 12 is a schematic sectional view of a temperature sensor.
【図１３】エレクトロルミネッセンス素子の概略断面図
である。FIG. 13 is a schematic sectional view of an electroluminescent element.
【図１４】光センサーの概略断面図である。FIG. 14 is a schematic sectional view of an optical sensor.
【図１５】正バイアスの過渡光電流波形を示すグラフで
ある。FIG. 15 is a graph showing a positive bias transient photocurrent waveform.
【図１６】逆バイアスの過渡光電流波形を示すグラフで
ある。FIG. 16 is a graph showing a reverse bias transient photocurrent waveform.
【図１７】電荷移動度の電界依存性を測定した際のグラ
フである。FIG. 17 is a graph when the electric field dependence of the charge mobility is measured.
【図１８】印加電圧に対する発光強度のグラフである。FIG. 18 is a graph of light emission intensity versus applied voltage.
【図１９】波長毎の発光強度のグラフである。FIG. 19 is a graph of emission intensity for each wavelength.
【図２０】印加電圧に対する発光強度のグラフである。FIG. 20 is a graph of light emission intensity versus applied voltage.
１１ 情報記録層 １３ 透明電極 １３’ 電極 １４ 液晶性電荷輸送層 １４’ 電荷発生層 １５ 透明基板 １５’ 基板 １６ 保護層 １８ スペーサー １９ 空間 ２０ 誘電体層 ５１ ガラス板 ５２ 偏光フィルム ５３ 液晶層 ５４ 光照射 ６１ ソース電極 ６２ ドレイン ６３ ゲート電極 ６４ 基板 ６５ ゲート誘電体層 ７１ 発光層 DESCRIPTION OF SYMBOLS 11 Information recording layer 13 Transparent electrode 13 'Electrode 14 Liquid crystal charge transport layer 14' Charge generation layer 15 Transparent substrate 15 'Substrate 16 Protective layer 18 Spacer 19 Space 20 Dielectric layer 51 Glass plate 52 Polarizing film 53 Liquid crystal layer 54 Light irradiation 61 Source electrode 62 Drain 63 Gate electrode 64 Substrate 65 Gate dielectric layer 71 Light emitting layer
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 3K007 AB05 AB11 AB18 CA01 CB01 DA05 EA04 EB00 4H027 BE06 DJ01 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 3K007 AB05 AB11 AB18 CA01 CB01 DA05 EA04 EB00 4H027 BE06 DJ01
Claims (15)
であって、Ｌ基の炭素数とＲ基の炭素数が異なる）を有
する非対称液晶性物質を含んでなることを特徴とする、
液晶性電荷輸送材料。(1) The following general formula: Wherein the L group and / or R group is a group containing a carbon atom, wherein the number of carbon atoms of the L group and the number of carbon atoms of the R group are different from each other.
Liquid crystalline charge transport material.
ルボニル基を含まないものである、請求項１に記載の液
晶性電荷輸送材料。2. The liquid crystalline charge transport material according to claim 1, wherein in the general formula, the L group and the R group do not contain a carbonyl group.
素原子を含まないものである、請求項１に記載の液晶性
電荷輸送材料。3. The liquid crystalline charge transport material according to claim 1, wherein in the general formula, the L group and the R group do not contain an oxygen atom.
ルキル基である、請求項１に記載の液晶性電荷輸送材
料。4. The liquid crystalline charge transport material according to claim 1, wherein in the general formula, the L group and the R group are alkyl groups.
上である、請求項１に記載の液晶性電荷輸送材料。5. The liquid crystal charge transport material according to claim 1, wherein the hole mobility is 1 × 10 −5 cm 2 / Vs or more.
上である、請求項１に記載の液晶性電荷輸送材料。6. The liquid crystalline charge transport material according to claim 1, wherein the electron mobility is 1 × 10 −5 cm 2 / Vs or more.
晶性電荷輸送材料。7. The liquid crystalline charge transport material according to claim 1, which is an EL device material.
動経路に有する、光センサー。8. An optical sensor having the liquid crystal charge transporting material according to claim 1 in a driving path.
動経路に有する、エレクトロルミネッセンス素子。9. An electroluminescent device having the liquid crystal charge transporting material according to claim 1 in a driving path.
駆動経路に有する、光導電体。10. A photoconductor having the liquid crystalline charge transporting material according to claim 1 in a driving path.
駆動経路に有する、空間光変調素子。11. A spatial light modulation device having the liquid crystal charge transporting material according to claim 1 in a driving path.
駆動経路に有する、薄膜トランジスター。12. A thin film transistor having the liquid crystal charge transporting material according to claim 1 in a driving path.
駆動経路に有する、温度センサー。13. A temperature sensor having the liquid crystal charge transporting material according to claim 1 in a driving path.
駆動経路に有する、画像表示素子。14. An image display device comprising the liquid crystalline charge transport material according to claim 1 in a drive path.
であって、Ｌ基の炭素数とＲ基の炭素数が異なる）を有
する非対称液晶性物質。15. The following general formula: (However, the L group and / or R group is a group containing a carbon atom, and the number of carbon atoms of the L group and the number of carbon atoms of the R group are different).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000051876A JP2001233872A (en) | 2000-02-28 | 2000-02-28 | Asymmetric liquid crystalline charge transport material having terthiophene skeleton |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000051876A JP2001233872A (en) | 2000-02-28 | 2000-02-28 | Asymmetric liquid crystalline charge transport material having terthiophene skeleton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001233872A true JP2001233872A (en) | 2001-08-28 |
Family
ID=18573471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000051876A Pending JP2001233872A (en) | 2000-02-28 | 2000-02-28 | Asymmetric liquid crystalline charge transport material having terthiophene skeleton |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001233872A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004273678A (en) * | 2003-03-07 | 2004-09-30 | Konica Minolta Holdings Inc | Organic thin film transistor |
| JP2006234738A (en) * | 2005-02-28 | 2006-09-07 | Dainippon Printing Co Ltd | Substrate, device and method for measuring carrier mobility of semiconductor thin film |
| WO2007142228A1 (en) * | 2006-06-08 | 2007-12-13 | National Institute Of Advanced Industrial Science And Technology | Smectic liquid crystal compound |
| JP2008513544A (en) * | 2004-09-14 | 2008-05-01 | ノースウェスタン ユニバーシティ | Carbonyl-functionalized thiophene compounds and related device structures |
| JP2009114074A (en) * | 2007-11-01 | 2009-05-28 | Sumitomo Seika Chem Co Ltd | (thiophene/phenylene) co-oligomer |
| JP2009231407A (en) * | 2008-03-21 | 2009-10-08 | National Institute Of Advanced Industrial & Technology | Organic semiconductor thin-film and organic thin-film transistor using same |
-
2000
- 2000-02-28 JP JP2000051876A patent/JP2001233872A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004273678A (en) * | 2003-03-07 | 2004-09-30 | Konica Minolta Holdings Inc | Organic thin film transistor |
| JP2008513544A (en) * | 2004-09-14 | 2008-05-01 | ノースウェスタン ユニバーシティ | Carbonyl-functionalized thiophene compounds and related device structures |
| JP2006234738A (en) * | 2005-02-28 | 2006-09-07 | Dainippon Printing Co Ltd | Substrate, device and method for measuring carrier mobility of semiconductor thin film |
| JP4680630B2 (en) * | 2005-02-28 | 2011-05-11 | 大日本印刷株式会社 | Substrate for measuring carrier mobility of semiconductor thin film, measuring apparatus and measuring method |
| WO2007142228A1 (en) * | 2006-06-08 | 2007-12-13 | National Institute Of Advanced Industrial Science And Technology | Smectic liquid crystal compound |
| JP2008013539A (en) * | 2006-06-08 | 2008-01-24 | National Institute Of Advanced Industrial & Technology | Smectic liquid crystal compound |
| US7915609B2 (en) | 2006-06-08 | 2011-03-29 | National Institute Of Advanced Industrial Science And Technology | Smectic liquid crystal compound |
| JP2009114074A (en) * | 2007-11-01 | 2009-05-28 | Sumitomo Seika Chem Co Ltd | (thiophene/phenylene) co-oligomer |
| JP2009231407A (en) * | 2008-03-21 | 2009-10-08 | National Institute Of Advanced Industrial & Technology | Organic semiconductor thin-film and organic thin-film transistor using same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4598282B2 (en) | Amine compound and organic electroluminescent device containing the compound | |
| US7883788B2 (en) | Light emitting element, light emitting device, and electronic device | |
| JP2013520410A (en) | Compound for organic photoelectric device and organic photoelectric device including the same | |
| JP2009246139A (en) | Light-emitting element | |
| JPH08245955A (en) | Organic electroluminescent element | |
| JP2007073500A (en) | Light emitting element, light emitting device and electronic device | |
| WO2004066315A2 (en) | Benzoxazinone and quinazolinone derivatives | |
| WO2007004729A1 (en) | Light-emitting element, light-emitting device, and electronic device | |
| KR20090131958A (en) | Novel compound for organic photoelectric device and organic photoelectric device comprising same | |
| JP2006273792A (en) | Organic charge-transporting compound and method for producing the same, and organic electronic device | |
| Ogawa et al. | Tri (p-terphenyl-4-yl) amine as a novel blue-emitting material for organic electroluminescent devices | |
| TW200539749A (en) | Organic electroluminescent device, method for manufacturing same and organic solution | |
| JP2001233872A (en) | Asymmetric liquid crystalline charge transport material having terthiophene skeleton | |
| JP2006506824A (en) | Azulene group compounds in organic light emitting device elements | |
| JP3779625B2 (en) | Light emitting element | |
| JPH10312711A (en) | Liquid crystalline electron charge transporting material | |
| JPH0790255A (en) | Organic electroluminescent device | |
| JPH11251068A (en) | Organic electroluminescence element | |
| KR980013534A (en) | Electroluminescent element | |
| JPH09316442A (en) | Liquid crystal charge-transporting material | |
| JP2005317440A (en) | Organic electroluminescent element, its manufacturing method and electronic apparatus | |
| JP3555271B2 (en) | Blue light emitting element | |
| KR100672301B1 (en) | High Efficient Organic Electroluminescent Display Device | |
| JP4180682B2 (en) | Liquid crystalline charge transport material | |
| JPH11241069A (en) | Liquid crystalline charge transport material |