JP3261881B2 - Hole transport material and its use - Google Patents
Hole transport material and its useInfo
- Publication number
- JP3261881B2 JP3261881B2 JP22141994A JP22141994A JP3261881B2 JP 3261881 B2 JP3261881 B2 JP 3261881B2 JP 22141994 A JP22141994 A JP 22141994A JP 22141994 A JP22141994 A JP 22141994A JP 3261881 B2 JP3261881 B2 JP 3261881B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- layer
- organic
- 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.)
- Expired - Fee Related
Links
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Description
【0001】[0001]
【産業上の利用分野】本発明はトリフェニルアミン構造
を有する正孔輸送材料に関し、該トリフェニルアミン化
合物は、感光材料、有機光導電材料として使用でき、さ
らに具体的には、平面光源や表示に使用される有機エレ
クトロルミネッセンス(EL)素子もしくは電子写真感
光体等の正孔輸送材料として利用できる。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hole transporting material having a triphenylamine structure, and the triphenylamine compound can be used as a photosensitive material or an organic photoconductive material. It can be used as a hole transporting material for an organic electroluminescence (EL) element or an electrophotographic photosensitive member used for the above.
【0002】[0002]
【従来の技術】感光材料や正孔輸送材料として開発され
ている有機光導電材料は、低コスト、加工性が多様であ
り、無公害性などの多くの利点があり、多くの化合物が
提案されている。例えば、オキサジアゾール誘導体(米
国特許第3,189,447号)、オキサゾール誘導体
(米国特許第3,257,203号)、ヒドラゾン誘導
体(米国特許第3,717,462号、特開昭54−5
9,143号、米国特許第4,150,978号)、ト
リアリールピラゾリン誘導体(米国特許第3,820,
989号、特開昭51−93,224号、特開昭55−
108,667号)、アリールアミン誘導体(米国特許
第3,180,730号、米国特許第4,232,10
3号、特開昭55−144,250号、特開昭56−1
19,132号)、スチルベン誘導体(特開昭58−1
90,953号、特開昭59−195,658号)など
の有機光導電性材料が開示されている。2. Description of the Related Art Organic photoconductive materials that have been developed as photosensitive materials and hole transport materials have many advantages such as low cost, various processability, and no pollution, and many compounds have been proposed. ing. For example, oxadiazole derivatives (U.S. Pat. No. 3,189,447), oxazole derivatives (U.S. Pat. No. 3,257,203), hydrazone derivatives (U.S. Pat. 5
9,143, U.S. Pat. No. 4,150,978), triarylpyrazoline derivatives (U.S. Pat.
No. 989, JP-A-51-93,224 and JP-A-55-93.
No. 108,667), arylamine derivatives (US Pat. No. 3,180,730, US Pat. No. 4,232,10).
3, JP-A-55-144250, JP-A-56-1
No. 19,132), stilbene derivatives (JP-A-58-1)
No. 90,953, JP-A-59-195,658) and the like.
【0003】正孔輸送材料を利用した技術の一つとして
は、有機EL素子が挙げられる。有機物質を使用したE
L素子は、固体発光型の安価な大面積フルカラー表示素
子としての用途が有望視され、多くの開発が行われてい
る。一般にEL素子は発光層および該層をはさんだ一対
の対向電極から構成されている。発光は、両電極間に電
界が印加されると、陰極側から電子が注入され、陽極側
から正孔が注入され、この電子が発光層において正孔と
再結合し、エネルギー準位が伝導帯から価電子帯に戻る
際にエネルギーを光として放出する現象である。[0003] One of the techniques using a hole transport material is an organic EL device. E using organic substances
The L element is expected to be used as a solid-state light-emitting inexpensive large-area full-color display element, and many developments have been made. Generally, an EL element is composed of a light emitting layer and a pair of opposed electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side, holes are injected from the anode side , and the electrons recombine with holes in the light emitting layer, and the energy level is changed to the conduction band. This is a phenomenon in which energy is emitted as light when returning to the valence band from.
【0004】従来の有機EL素子は、無機EL素子に比
べて駆動電圧が高く、発光輝度や発光効率も低かった。
また、特性劣化も著しく実用化には至っていなかった。
近年、10V以下の低電圧で発光する高い蛍光量子効率
を持った有機化合物を含有した薄膜を積層した有機EL
素子が報告され、関心を集めている(アプライド・フィ
ジクス・レターズ、51巻、913ページ、1987年
参照)。この方法は、金属キレート錯体を蛍光体層、ア
ミン系化合物を正孔注入層に使用して、高輝度の緑色発
光を得ており、6〜7Vの直流電圧で輝度は100cd
/m2、最大発光効率は1.5lm/Wを達成して、実
用領域に近い性能を持っている。[0004] Conventional organic EL devices have a higher driving voltage and lower luminous luminance and luminous efficiency than inorganic EL devices.
In addition, the characteristic deterioration was remarkable, and it had not been put to practical use.
2. Description of the Related Art In recent years, an organic EL in which thin films containing an organic compound having high fluorescence quantum efficiency and emitting light at a low voltage of 10 V or less are stacked
Devices have been reported and are of interest (see Applied Physics Letters, vol. 51, p. 913, 1987). This method uses a metal chelate complex for a phosphor layer and an amine compound for a hole injection layer to obtain high-luminance green light emission. The luminance is 100 cd at a DC voltage of 6 to 7 V.
/ M 2 , and a maximum luminous efficiency of 1.5 lm / W, which is close to the practical range.
【0005】しかしながら、現在までの有機EL素子
は、発光輝度や繰り返し使用時の発光安定性は未だ充分
ではない。従って、より大きな発光輝度を持ち、繰り返
し使用時での安定性の優れた有機EL素子の開発のため
に、優れた正孔輸送能力を有し、耐久性のある正孔輸送
材料の開発が望まれている。[0005] However, the organic EL devices up to now do not have sufficient light emission luminance and light emission stability when used repeatedly. Therefore, in order to develop an organic EL device having higher emission luminance and excellent stability in repeated use, it is desired to develop a hole transporting material having excellent hole transporting ability and durability. It is rare.
【0006】さらに、正孔輸送材料を利用した技術とし
ては、電子写真感光体が挙げられる。電子写真方式は、
カールソンにより発明された画像形成法の一つである。
この方式は、コロナ放電により感光体を帯電した後、光
像露光して感光体に静電潜像を得、該静電潜像にトナー
を付着させて現像し、得られたトナー像を紙へ転写する
ことからなる。このような電子写真方式における感光体
に要求される基本的な特性としては、暗所において適当
な電位が保持されること、暗所における電荷の放電が少
ないこと、光照射により速やかに電荷を放電することな
どが挙げられる。従来までの電子写真感光体は、セレ
ン、セレン合金、酸化亜鉛、硫化カドミウムおよびテル
ルなどの無機光導電体が使用されてきた。これらの無機
光導電体は、耐久性が高く、耐刷枚数が多いなどの利点
を有しているが、製造コストが高く、加工性が劣り、毒
性を有するなどの問題点が指摘されている。これらの欠
点を克服するために有機感光体の開発が行われている
が、従来までの有機光導電材料を正孔輸送材料として用
いた電子写真感光体は、帯電性、感度および残留電位な
どの電子写真特性が、必ずしも満足されているとは言え
ないのが現状であり、優れた電荷輸送能力を有し、耐久
性のある正孔輸送材料の開発が望まれていた。Further, as a technique using a hole transport material, there is an electrophotographic photosensitive member. The electrophotographic method is
This is one of the image forming methods invented by Carlson.
In this method, a photoconductor is charged by corona discharge, and then exposed to a light image to obtain an electrostatic latent image on the photoconductor, toner is adhered to the electrostatic latent image and developed, and the obtained toner image is printed on paper. Transfer to The basic characteristics required of the photoreceptor in such an electrophotographic system are that an appropriate potential is maintained in a dark place, that the electric charge is less discharged in the dark place, and that the electric charge is quickly discharged by light irradiation. And so on. Conventional electrophotographic photoreceptors have used inorganic photoconductors such as selenium, selenium alloys, zinc oxide, cadmium sulfide, and tellurium. These inorganic photoconductors have advantages such as high durability and a large number of printing presses, but problems such as high production cost, poor workability, and toxicity have been pointed out. . To overcome these drawbacks, organic photoconductors have been developed.However, conventional electrophotographic photoconductors using organic photoconductive materials as hole transport materials are not suitable for charging, sensitivity and residual potential. At present, it cannot be said that the electrophotographic characteristics are always satisfied, and it has been desired to develop a hole transport material having excellent charge transport ability and durability.
【0007】[0007]
【発明が解決しようとする課題】本発明の目的は、優れ
た正孔輸送能力を有し、耐久性のある正孔輸送材料を提
供することにあり、さらにこの正孔輸送材料を繰り返し
て使用した際の安定性の優れた有機EL素子、電子写真
感光体等を提供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a durable hole transporting material having excellent hole transporting ability, and further using this hole transporting material repeatedly. It is an object of the present invention to provide an organic EL device, an electrophotographic photoreceptor, and the like having excellent stability in the above-mentioned case.
【0008】[0008]
【課題を解決するための手段】本発明者らは鋭意検討し
た結果、一般式[1]で示される少なくとも一種の正孔
輸送材料は、正孔輸送能力が大きく、これを用いて作製
した有機EL素子もしくは電子写真感光体等の素子の感
度もしくは繰り返し使用時での安定性が優れていること
を見いだし本発明に至った。 一般式[1]Means for Solving the Problems As a result of intensive studies, the present inventors have found that at least one kind of hole transporting material represented by the general formula [1] has a large hole transporting ability, and an organic material prepared by using the same. The inventors have found that the sensitivity of an element such as an EL element or an electrophotographic photosensitive member or the stability upon repeated use is excellent, and have reached the present invention. General formula [1]
【0009】[0009]
【化2】 Embedded image
【0010】[式中、R1〜R16は、水素原子、ハロゲ
ン原子、置換もしくは未置換のアルキル基、置換もしく
は未置換のアルコキシ基、置換もしくは未置換のチオア
ルコキシ基、シアノ基、アミノ基、モノまたはジ置換ア
ミノ基、水酸基、メルカプト基、置換もしくは未置換の
アリールオキシ基、置換もしくは未置換のアリールチオ
基、置換もしくは未置換の炭素環式芳香族環基、置換も
しくは未置換の複素環式芳香族環基、置換もしくは未置
換の複素環基を表し(隣接した置換基同士で置換もしく
は未置換の脂肪族式環、置換もしくは未置換の炭素環式
芳香族環、置換もしくは未置換の複素環式芳香族環基、
置換もしくは未置換の複素環を形成しても良い。)、X
1、X2は、水素原子、ハロゲン原子、置換もしくは未置
換のアルキル基、置換もしくは未置換のアルコキシ基、
置換もしくは未置換の炭素環式芳香族環基を表す(X1
とX2とで置換もしくは未置換の脂肪族脂環基を形成し
てもよい。)。]Wherein R 1 to R 16 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a cyano group, an amino group , Mono- or di-substituted amino group, hydroxyl group, mercapto group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted carbocyclic aromatic ring group, substituted or unsubstituted heterocyclic ring Represents a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted Heterocyclic aromatic ring group,
A substituted or unsubstituted heterocyclic ring may be formed. ), X
1 and X 2 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group,
(X 1 represents a substituted or unsubstituted carbocyclic aromatic ring group;
And X 2 may form a substituted or unsubstituted aliphatic alicyclic group. ). ]
【0011】更に本発明は、一対の電極間に、一層また
は複数層の有機化合物薄膜よりなる発光層を備えた有機
エレクトロルミネッセンス素子において、少なくとも一
層が一般式[1]で示される化合物を含有する層である
有機エレクトロルミネッセンス素子である。Further, the present invention provides an organic electroluminescent device having a light-emitting layer composed of one or more organic compound thin films between a pair of electrodes, wherein at least one layer contains a compound represented by the general formula [1]. The organic electroluminescent device is a layer.
【0012】[0012]
【0013】本発明における一般式[1]で示される化
合物の、R1〜R16の具体例は、ハロゲン原子としては
弗素、塩素、臭素、ヨウ素がある。置換もしくは未置換
のアルキル基としては、メチル基、エチル基、プロピル
基、ブチル基、sec−ブチル基、tert−ブチル
基、ペンチル基、ヘキシル基、ヘプチル基、オクチル
基、ステアリル基、トリクロロメチル基、トリフロロメ
チル基、シクロプロピル基、シクロヘキシル基、1,3
−シクロヘキサジエニル基、2−シクロペンテン−1−
イル基、2,4−シクロペンタジエン−1−イリデニル
基等がある。置換もしくは未置換のアルコキシ基として
は、メトキシ基、エトキシ基、プロポキシ基、n−ブト
キシ基、sec−ブトキシ基、tert−ブトキシ基、
ペンチルオキシ基、ヘキシルオキシ基、ステアリルオキ
シ基、トリフロロメトキシ基等がある。置換もしくは未
置換のチオアルコキシ基としては、メチルチオ基、エチ
ルチオ基、プロピルチオ基、ブチルチオ基、sec−ブ
チルチオ基、tert−ブチルチオ基、ペンチルチオ
基、ヘキシルチオ基、ヘプチルチオ基、オクチルチオ基
等がある。Specific examples of R 1 to R 16 of the compound represented by the general formula [1] in the present invention include fluorine, chlorine, bromine and iodine as halogen atoms. Examples of the substituted or unsubstituted alkyl group include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, stearyl, and trichloromethyl groups. , Trifluoromethyl group, cyclopropyl group, cyclohexyl group, 1,3
-Cyclohexadienyl group, 2-cyclopentene-1-
Examples include an yl group and a 2,4-cyclopentadiene-1-yridenyl group. Examples of the substituted or unsubstituted alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group,
Examples include a pentyloxy group, a hexyloxy group, a stearyloxy group, and a trifluoromethoxy group. Examples of the substituted or unsubstituted thioalkoxy group include methylthio, ethylthio, propylthio, butylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, heptylthio, octylthio, and the like.
【0014】モノまたはジ置換アミノ基としては、メチ
ルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエ
チルアミノ基、ジプロピルアミノ基、ジブチルアミノ基
等のアルキル基置換アミノ基、ジフェニルアミノ基、ジ
トリルアミノ基等の炭素環式芳香族アミノ基、ビス(ア
セトオキシメチル)アミノ基、ビス(アセトオキシエチ
ル)アミノ基、ビス(アセトオキシプロピル)アミノ
基、ビス(アセトオキシブチル)アミノ基、ジベンジル
アミノ基等がある。置換もしくは未置換のアリールオキ
シ基としては、フェノキシ基、p−tert−ブチルフ
ェニキシ基、3−フルオロフェニキシ基等がある。置換
もしくは未置換のアリールチオ基としては、フェニルチ
オ基、3−フルオロフェニルチオ基等がある。置換もし
くは未置換の炭素環式芳香族環基としては、フェニル
基、ビフェニレニル基、トリフェニレニル基、テトラフ
ェニレニル基、3−ニトロフェニル基、4−メチルチオ
フェニル基、3,5−ジシアノフェニル基、o−,m−
およびp−トリル基、キシリル基、o−,m−およびp
−クメニル基、メシチル基、ペンタレニル基、インデニ
ル基、ナフチル基、アズレニル基、ヘプタレニル基、ア
セナフチレニル基、フェナレニル基、フルオレニル基、
アントリル基、アントラキノニル基、3−メチルアント
リル基、フェナントリル基、トリフェニレニル基、ピレ
ニル基、クリセニル基、2−エチル−1−クリセニル
基、ピセニル基、ペリレニル基、6−クロロペリレニル
基、ペンタフェニル基、ペンタセニル基、テトラフェニ
レニル基、ヘキサフェニル基、ヘキサセニル基、ルビセ
ニル基、コロネニル基、トリナフチレニル基、ヘプタフ
ェニル基、ヘプタセニル基、ピラントレニル基、オバレ
ニル基等がある。Examples of the mono- or di-substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group and other alkyl-substituted amino groups, a diphenylamino group, a ditolylamino group and the like. Carbocyclic aromatic amino group, bis (acetooxymethyl) amino group, bis (acetooxyethyl) amino group, bis (acetooxypropyl) amino group, bis (acetooxybutyl) amino group, dibenzylamino group, etc. There is. Examples of the substituted or unsubstituted aryloxy group include a phenoxy group, a p-tert-butylphenoxy group, and a 3-fluorophenoxy group. Examples of the substituted or unsubstituted arylthio group include a phenylthio group and a 3-fluorophenylthio group. As a substituted or unsubstituted carbocyclic aromatic ring group, a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, a 3-nitrophenyl group, a 4-methylthiophenyl group, a 3,5-dicyanophenyl group, o-, m-
And p-tolyl group, xylyl group, o-, m- and p
-Cumenyl group, mesityl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group,
Anthryl group, anthraquinonyl group, 3-methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, 2-ethyl-1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperylenyl group, pentaphenyl group, pentacenyl Groups, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyrantrenyl group, an ovarenyl group, and the like.
【0015】置換もしくは未置換の複素環式芳香族環基
としては、チオニル基、フリル基、ピロリル基、イミダ
ゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、
ピリミジニル基、ピリダジニル基、インドリル基、キノ
リル基、イソキノリル基、フタラジニル基、キノキサリ
ニル基、キナゾリニル基、カルバゾリル基、アクリジニ
ル基、フェナジニル基、フルフリル基、イソチアゾリル
基、イソキサゾリル基、フラザニル基、フェノキサジニ
ル基、ベンゾチアゾリル基、ベンゾオキサゾリル基、ベ
ンズイミダゾリル基、2−メチルピリジル基、3−シア
ノピリジル基等がある。The substituted or unsubstituted heterocyclic aromatic ring groups include a thionyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group,
Pyrimidinyl group, pyridazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, furazanyl group, phenoxazinyl group, benzothiazolyl group Benzooxazolyl group, benzimidazolyl group, 2-methylpyridyl group, 3-cyanopyridyl group and the like.
【0016】好ましいR1〜R16としては、水素原子
(この場合は無置換体となる。)炭素原子が1〜4の低
級アルキル基もしくは低級アルコキシ基である。また、
隣接した置換基同士で5ないし7員環の酸素原子、窒素
原子、硫黄原子等が含まれてもよい脂肪族、炭素環式芳
香族、複素環式芳香族、複素環を形成してもよく、これ
らの環の任意の位置にさらに置換基を有していてもよ
い。Preferred R 1 to R 16 are a lower alkyl group or a lower alkoxy group having 1 to 4 hydrogen atoms (in this case, unsubstituted). Also,
Adjacent substituents may form an aliphatic, carbocyclic aromatic, heterocyclic aromatic, or heterocyclic ring which may contain a 5- to 7-membered oxygen atom, nitrogen atom, sulfur atom, etc. May have a substituent at any position of these rings.
【0017】本発明における一般式[1]で示される化
合物のX1〜X2 の具体例としては、水素原子の他、上
記R1〜R16で例示したハロゲン原子、置換もしくは未
置換のアルキル基、置換もしくは未置換のアルコキシ
基、置換もしくは未置換の脂肪族脂環基を挙げることが
できる。本発明の一般式[1]で示される化合物は、例
えば以下の方法により製造することができる。Specific examples of X 1 to X 2 of the compound represented by the general formula [1] in the present invention include a hydrogen atom, a halogen atom exemplified for R 1 to R 16 , and a substituted or unsubstituted alkyl. And substituted or unsubstituted alkoxy groups and substituted or unsubstituted aliphatic alicyclic groups. The compound represented by the general formula [1] of the present invention can be produced, for example, by the following method.
【0018】一般式[1]の本発明の化合物は、一般式
[2]の基本骨格のカルボキシ基に、トリフェニルアミ
ン誘導体を、窒素雰囲気下、有機溶媒中で、酸触媒の存
在下で、所定の温度、所定の時間反応させて得ることが
出来る。The compound of the present invention represented by the general formula [1] is prepared by adding a triphenylamine derivative to a carboxy group of the basic skeleton of the general formula [2] in an organic solvent under a nitrogen atmosphere in the presence of an acid catalyst. It can be obtained by reacting at a predetermined temperature for a predetermined time.
【0019】一般式[2]の化合物に、4〜5倍モルの
下記一般式[3]で示される置換基を有するトリフェニ
ルアミン化合物を酢酸溶媒中、メタンスルホン酸等の酸
触媒を用いて脱水反応させることにより、一般式[1]
で示されるトリフェニルアミン誘導体を製造することが
できる。また、本発明で用いられる酸触媒としては、メ
タンスルホン酸の代わりに、トリフルオロ酢酸、p−ト
ルエンスルホン酸の様な有機酸、または、硫酸、塩酸、
ルイス酸等も可能である。また、有機溶剤としては、酢
酸の他に、1,4−ジオキサン、エーテル、石油エーテ
ル等も可能である。 一般式[2]A 4- to 5-fold molar amount of a triphenylamine compound having a substituent represented by the following general formula [3] is added to the compound of the general formula [2] in an acetic acid solvent using an acid catalyst such as methanesulfonic acid. By performing a dehydration reaction, general formula [1]
Can be produced. Further, as the acid catalyst used in the present invention, instead of methanesulfonic acid, trifluoroacetic acid, an organic acid such as p-toluenesulfonic acid, or sulfuric acid, hydrochloric acid,
Lewis acids and the like are also possible. Further, as the organic solvent, in addition to acetic acid, 1,4-dioxane, ether, petroleum ether and the like are also possible. General formula [2]
【0020】[0020]
【化3】 Embedded image
【0021】一般式[3]General formula [3]
【0022】[0022]
【化4】 Embedded image
【0023】以下に、本発明の化合物の代表例を表1に
具体的に例示するが、本発明は以下の代表例に限定され
るものではない。Hereinafter, typical examples of the compounds of the present invention are specifically shown in Table 1, but the present invention is not limited to the following typical examples.
【0024】[0024]
【表1】 [Table 1]
【0025】 [0025]
【0026】 [0026]
【0027】 [0027]
【0028】本発明の正孔輸送材料は、他の正孔もしく
は電子輸送性化合物と混合して使用してもさしつかえな
い。本発明の化合物は正孔輸送性に優れているので、正
孔輸送性材料として極めて有効に使用することができ
る。The hole transporting material of the present invention may be used in a mixture with another hole or electron transporting compound. Since the compound of the present invention has excellent hole transporting properties, it can be used very effectively as a hole transporting material.
【0029】まず、一般式[1]で示される化合物を有
機EL素子の正孔輸送材料として用いる場合について説
明する。図1〜3に、本発明で使用される有機EL素子
の模式図の一例を示した。図中、一般的に電極Aである
2は陽極であり、電極Bである6は陰極である。また、
(電極A/発光層/電子注入層/電極B)の層構成で積
層した有機EL素子もあり、一般式[1]の化合物は、
どの素子構成においても好適に使用することが出来る。
一般式[1]の化合物は、大きな正孔輸送能力をもって
いるので、正孔注入層3もしくは発光層4のいずれの層
においても、正孔輸送材料として使用できる。First, the case where the compound represented by the general formula [1] is used as a hole transport material of an organic EL device will be described. FIGS. 1 to 3 show examples of schematic diagrams of an organic EL device used in the present invention. In the figure, generally, electrode 2, 2 is an anode, and electrode B, 6 is a cathode. Also,
There is also an organic EL device laminated with a layer structure of (electrode A / light-emitting layer / electron injection layer / electrode B), and the compound of general formula [1]
Any device configuration can be suitably used.
Since the compound of the general formula [1] has a large hole transporting ability, it can be used as a hole transporting material in any of the hole injection layer 3 and the light emitting layer 4.
【0030】図1の発光層4には、必要があれば、本発
明の一般式[1]の化合物に加えて、発光物質、発光補
助材料、キャリア輸送を行う正孔輸送材料や電子輸送材
料を使用することもできる。図2の構造は、発光層4と
正孔注入層3を分離している。この構造により、正孔注
入層3から発光層4への正孔注入効率が向上して、発光
輝度や発光効率を増加させることができる。この場合、
発光効率のためには、発光層に使用される発光物質自身
が電子輸送性であること、または発光層中に電子輸送輸
送材料を添加して発光層を電子輸送性にすることが望ま
しい。The light-emitting layer 4 in FIG. 1 may include, if necessary, a light-emitting substance, a light-emitting auxiliary material, a hole-transporting material for transporting carriers, and an electron-transporting material, in addition to the compound of the general formula [1] of the present invention. Can also be used. In the structure of FIG. 2, the light emitting layer 4 and the hole injection layer 3 are separated. With this structure, the hole injection efficiency from the hole injection layer 3 to the light emitting layer 4 is improved, and the light emission luminance and the light emission efficiency can be increased. in this case,
For luminous efficiency, it is desirable that the luminescent substance used in the luminescent layer itself has an electron transporting property, or that the luminescent layer is made to have an electron transporting property by adding an electron transporting material to the luminescent layer.
【0031】図3の構造は、正孔注入層3に加えて電子
注入層5を有し、発光層4での正孔と電子の再結合の効
率を向上させている。このように、有機EL素子を多層
構造にすることにより、クエンチングによる輝度や寿命
の低下を防ぐことができる。図2および図3の素子にお
いても、必要があれば、発光物質、発光補助材料、キャ
リア輸送を行う正孔輸送材料や電子輸送材料を組み合わ
せて使用することが出来る。また、正孔注入層、発光
層、電子注入層は、それぞれ二層以上の層構成により形
成されても良い。The structure shown in FIG. 3 has an electron injection layer 5 in addition to the hole injection layer 3 to improve the efficiency of recombination of holes and electrons in the light emitting layer 4. In this manner, by making the organic EL element have a multilayer structure, it is possible to prevent a decrease in luminance and life due to quenching. 2 and 3, the light-emitting substance, the light-emitting auxiliary material, the hole-transporting material for transporting carriers, and the electron-transporting material can be used in combination, if necessary. Further, each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed in a layer structure of two or more layers.
【0032】有機EL素子の陽極に使用される導電性物
質としては、4eVより大きな仕事関数を持つものが好
適であり、炭素、アルミニウム、バナジウム、鉄、コバ
ルト、ニッケル、タングステン、銀、金、白金、パラジ
ウム等およびそれらの合金、ITO基板、NESA基板
と称される酸化スズ、酸化インジウム等の酸化金属、さ
らにはポリチオフェンやポリピロール等の有機導電性樹
脂が用いられる。陰極に使用される導電性物質として
は、4eVより小さな仕事関数を持つものが好適であ
り、マグネシウム、カルシウム、錫、鉛、チタニウム、
イットリウム、リチウム、ルテニウム、マンガン等およ
びそれらの合金が用いられるが、これらに限定されるも
のではない。陽極および陰極は、必要があれば二層以上
の層構成により形成されていても良い。As the conductive substance used for the anode of the organic EL element, those having a work function of more than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum , Palladium and the like, alloys thereof, metal oxides such as tin oxide and indium oxide called ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the cathode, those having a work function of less than 4 eV are preferable, and magnesium, calcium, tin, lead, titanium,
Yttrium, lithium, ruthenium, manganese, and the like and alloys thereof are used, but are not limited thereto. The anode and the cathode may be formed by two or more layers if necessary.
【0033】有機EL素子では、効率良く発光させるた
めに、2で示される電極Aまたは6で示される電極Bの
うち、少なくとも一方は素子の発光波長領域において充
分透明にすることが望ましい。また、基板1も透明であ
ることが望ましい。透明電極は、上記した導電性物質を
使用して、蒸着やスパッタリング等の方法で所定の透光
性が確保するように設定する。発光面の電極は、光透過
率を10%以上にすることが望ましい。In the organic EL device, in order to efficiently emit light, at least one of the electrode A 2 and the electrode B 6 is desirably sufficiently transparent in the emission wavelength region of the device. Further, it is desirable that the substrate 1 is also transparent. The transparent electrode is set so as to secure a predetermined light transmittance by a method such as vapor deposition or sputtering using the above-described conductive substance. The electrode on the light emitting surface desirably has a light transmittance of 10% or more.
【0034】基板1は、機械的、熱的強度を有し、透明
なものであれば限定されるものではないが、例示する
と、ガラス基板、ポリエチレン板、ポリエーテルサルフ
ォン板、ポリプロピレン板等の透明樹脂があげられる。The substrate 1 is not limited as long as it has mechanical and thermal strengths and is transparent. Examples thereof include a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. Transparent resin.
【0035】本発明に係わる有機EL素子の各層の形成
は、真空蒸着、スパッタリング等の乾式成膜法やスピン
コーティング、ディッピング等の湿式成膜法のいずれの
方法を適用することができる。膜厚は特に限定されるも
のではないが、各層は適切な膜厚に設定する必要があ
る。膜厚が厚すぎると、一定の光出力を得るために大き
な印加電圧が必要になり効率が悪くなる。膜厚が薄すぎ
るとピンホール等が発生して、電界を印加しても充分な
発光輝度が得られない。通常の膜厚は5nmから10μ
mの範囲が好適であるが、10nmから0.2μmの範
囲がさらに好ましい。Each layer of the organic EL device according to the present invention can be formed by any of a dry film forming method such as vacuum evaporation and sputtering and a wet film forming method such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate thickness. If the film thickness is too large, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too small, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. Normal thickness is 5nm to 10μ
The range of m is suitable, but the range of 10 nm to 0.2 μm is more preferable.
【0036】湿式成膜法の場合、各層を形成する材料
を、クロロフォルム、テトラヒドロフラン、ジオキサン
等の適切な溶媒に溶解または分散して薄膜を形成する
が、その溶媒はいずれであっても良い。また、いずれの
薄膜においても、成膜性向上、膜のピンホール防止等の
ため適切な樹脂や添加剤を使用しても良い。このような
樹脂としては、ポリスチレン、ポリカーボネート、ポリ
アリレート、ポリエステル、ポリアミド、ポリウレタ
ン、ポリスルフォン、ポリメチルメタクリレート、ポリ
メチルアクリレート、セルロース等の絶縁性樹脂、ポリ
−N−ビニルカルバゾール、ポリシラン等の光導電性樹
脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙
げることができる。In the case of the wet film forming method, a material for forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any of the thin films, a suitable resin or additive may be used to improve film forming properties, prevent pinholes in the film, and the like. Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and photoconductive materials such as poly-N-vinyl carbazole and polysilane. And conductive resins such as polythiophene and polypyrrole.
【0037】本有機EL素子は、発光層、正孔注入層、
電子注入層において、必要があれば、一般式[1]の化
合物に加えて、公知の発光物質、発光補助材料、正孔輸
送材料、電子輸送材料を使用することもできる。The present organic EL device has a light emitting layer, a hole injection layer,
In the electron injection layer, if necessary, in addition to the compound of the general formula [1], a known light emitting substance, light emission auxiliary material, hole transport material, and electron transport material can also be used.
【0038】公知の発光物質または発光物質の補助材料
としては、アントラセン、ナフタレン、フェナントレ
ン、ピレン、テトラセン、コロネン、クリセン、フルオ
レセイン、ペリレン、フタロペリレン、ナフタロペリレ
ン、ペリノン、フタロペリノン、ナフタロペリノン、ジ
フェニルブタジエン、テトラフェニルブタジエン、クマ
リン、オキサジアゾール、アルダジン、ビスベンゾキサ
ゾリン、ビススチリル、ピラジン、シクロペンタジエ
ン、オキシン、アミノキノリン、イミン、ジフェニルエ
チレン、ビニルアントラセン、ジアミノカルバゾール、
ピラン、チオピラン、ポリメチン、メロシアニン、イミ
ダゾールキレート化オキシノイド化合物、キナクリド
ン、ルブレン等およびそれらの誘導体があるが、これら
に限定されるものではない。Known light-emitting substances or auxiliary materials for light-emitting substances include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene and tetraphenylbutadiene. , Coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, oxine, aminoquinoline, imine, diphenylethylene, vinylanthracene, diaminocarbazole,
Examples include, but are not limited to, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene, and derivatives thereof.
【0039】一般式[1]の正孔輸送材料と併せて使用
できる正孔輸送材料としては、正孔を輸送する能力を持
ち、発光層または発光物質に対して優れた正孔注入効果
を有し、発光層で生成した励起子の電子注入層または電
子輸送材料への移動を防止し、かつ薄膜形成能の優れた
化合物が挙げられる。具体的には、フタロシアニン系化
合物、ナフタロシアニン系化合物、ポルフィリン系化合
物、オキサジアゾール、トリアゾール、イミダゾール、
イミダゾロン、イミダゾールチオン、ピラゾリン、ピラ
ゾロン、テトラヒドロイミダゾール、オキサゾール、オ
キサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリ
アリールアルカン、スチルベン、ブタジエン、ベンジジ
ン型トリフェニルアミン、スチリルアミン型トリフェニ
ルアミン、ジアミン型トリフェニルアミン等と、それら
の誘導体、およびポリビニルカルバゾール、ポリシラ
ン、導電性高分子等の高分子材料等があるが、これらに
限定されるものではない。The hole transporting material that can be used in combination with the hole transporting material of the general formula [1] has the ability to transport holes and has an excellent hole injection effect on the light emitting layer or the light emitting substance. In addition, a compound that prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron transport material and has excellent thin film forming ability can be used. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole,
Imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine triphenylamine, styrylamine triphenylamine, diamine triphenylamine, etc. And derivatives thereof, and high molecular materials such as polyvinyl carbazole, polysilane, and conductive polymers, but are not limited thereto.
【0040】電子輸送材料としては、電子を輸送する能
力を持ち、発光層または発光物質に対して優れた電子注
入効果を有し、発光層で生成した励起子の正孔注入層ま
たは正孔輸送材料への移動を防止し、かつ薄膜形成能の
優れた化合物が挙げられる。例えば、フルオレノン、ア
ントラキノジメタン、ジフェノキノン、チオピランジオ
キシド、オキサジアゾール、ペリレンテトラカルボン
酸、フレオレニリデンメタン、アントラキノジメタン、
アントロン等とそれらの誘導体があるが、これらに限定
されるものではない。また、正孔輸送材料に電子受容物
質を、電子輸送材料に電子供与性物質を添加することに
より増感させることもできる。The electron transporting material has a capability of transporting electrons, has an excellent electron injecting effect on a light emitting layer or a light emitting substance, and has a hole injection layer or a hole transporting function of excitons generated in the light emitting layer. Compounds that prevent transfer to a material and have excellent thin film forming ability are exemplified. For example, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane,
Examples include, but are not limited to, anthrones and derivatives thereof. The sensitization can also be performed by adding an electron accepting substance to the hole transporting material and adding an electron donating substance to the electron transporting material.
【0041】図1,2および3に示される有機EL素子
において、本発明の一般式[1]の化合物は、いずれの
層に使用することができ、一般式[1]の化合物の他
に、発光物質、発光補助材料、正孔輸送材料および電子
輸送材料の少なくとも1種が同一層に含有されてもよ
い。また、本発明により得られた有機EL素子の、温
度、湿度、雰囲気等に対する安定性の向上のために、素
子の表面に保護層を設けたり、シリコンオイル等を封入
して素子全体を保護することも可能である。以上のよう
に、本発明では有機EL素子に一般式[1]の化合物を
用いたため、発光効率と発光輝度を高くできた。また、
この素子は熱や電流に対して非常に安定であり、さらに
は低い駆動電圧で実用的に使用可能の発光輝度が得られ
るため、従来まで大きな問題であった劣化も大幅に低下
させることができた。In the organic EL devices shown in FIGS. 1, 2 and 3, the compound of the general formula [1] of the present invention can be used for any layer, and in addition to the compound of the general formula [1], At least one of a light emitting substance, a light emission auxiliary material, a hole transport material, and an electron transport material may be contained in the same layer. In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or silicon oil or the like is sealed to protect the entire device. It is also possible. As described above, in the present invention, since the compound of the general formula [1] was used for the organic EL device, the luminous efficiency and the luminous brightness could be increased. Also,
This element is extremely stable against heat and current, and furthermore, it can emit light that can be used practically at a low driving voltage, so that the degradation, which was a major problem up to now, can be greatly reduced. Was.
【0042】本発明の有機EL素子は、壁掛けテレビ等
のフラットパネルディスプレイや、平面発光体として、
複写機やプリンター等の光源、液晶ディスプレイや計器
類等の光源、表示板、標識灯等へ応用が考えられ、その
工業的価値は非常に大きい。The organic EL device of the present invention can be used as a flat panel display such as a wall-mounted television, or as a flat luminous body.
It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and sign lamps, and its industrial value is extremely large.
【0043】次に、本発明の一般式[1]で示される化
合物を電子写真感光体として用いる場合について説明す
る。本発明の一般式[1]で示される化合物は、電子写
真感光体の何れの層においても使用できるが、高い正孔
輸送特性を有することから正孔輸送材料として使用する
ことが望ましい。該化合物は正孔輸送材料として作用
し、光を吸収することにより発生した電荷を極めて効率
よく輸送でき、高速応答性の感光体を得ることができ
る。また、該化合物は、耐オゾン性、光安定性に優れて
いるので、耐久性に優れた感光体を得ることができる。Next, the case where the compound represented by the general formula [1] of the present invention is used as an electrophotographic photosensitive member will be described. The compound represented by the general formula [1] of the present invention can be used in any layer of an electrophotographic photoreceptor, but is preferably used as a hole transporting material because of having high hole transporting properties. The compound acts as a hole transporting material, can transport charges generated by absorbing light extremely efficiently, and can provide a photoreceptor with high-speed response. Further, since the compound is excellent in ozone resistance and light stability, a photosensitive member having excellent durability can be obtained.
【0044】電子写真感光体は、導電性基板上に電荷発
生材料と、必要があれば電荷輸送材料を結着樹脂に分散
させてなる感光層を設けた単層型感光体、導電性基板上
に下引き層、電荷発生層、正孔輸送層の順に積層した、
もしくは導電性基板または下引き層上に正孔輸送層、電
荷発生層の順に積層した積層型感光体等がある。ここ
で、下引き層は必要がなければ使用しなくても良い。上
記感光体は、必要があれば活性ガスからの表面保護およ
びトナーによるフィルミング防止等の意味でオーバーコ
ート層を設けることも出来る。The electrophotographic photoreceptor is a single-layer type photoreceptor having a photosensitive layer in which a charge generation material and, if necessary, a charge transport material are dispersed in a binder resin on a conductive substrate. An undercoat layer, a charge generation layer, and a hole transport layer were laminated in this order,
Alternatively, there is a laminated photoconductor in which a hole transport layer and a charge generation layer are laminated on a conductive substrate or an undercoat layer in this order. Here, the undercoat layer may not be used if unnecessary. The photoreceptor may be provided with an overcoat layer, if necessary, for the purpose of protecting the surface from an active gas and preventing filming with a toner.
【0045】電荷発生材料としては、ビスアゾ、キナク
リドン、ジケトピロロピロール、インジゴ、ペリレン、
ペリノン、多環キノン、スクアリリウム塩、アズレニウ
ム塩、フタロシアニン、ナフタロシアニン等の有機化合
物、もしくは、セレン、セレン−テルル合金、硫化カド
ミウム、酸化亜鉛、アモルファスシリコン等の無機物質
が挙げられる。Examples of charge generation materials include bisazo, quinacridone, diketopyrrolopyrrole, indigo, perylene,
Organic compounds such as perinone, polycyclic quinone, squarylium salt, azulhenium salt, phthalocyanine, and naphthalocyanine; and inorganic substances such as selenium, selenium-tellurium alloy, cadmium sulfide, zinc oxide, and amorphous silicon.
【0046】感光体の各層は蒸着もしくは分散塗工方式
により成膜することが出来る。分散塗工は、スピンコー
ター、アプリケーター、スプレーコーター、浸漬コータ
ー、ローラーコーター、カーテンコーターおよびビード
コーター等を用いて行い、乾燥は室温から200℃、1
0分から6時間の範囲で静止または送風条件下で行う。
乾燥後の感光層の膜厚は単層型感光体の場合、5ミクロ
ンから50ミクロン、積層型感光体の場合、電荷発生層
は0.01から5ミクロン、好ましくは0.1から1ミ
クロンであり、正孔輸送層は5から50ミクロン、好ま
しくは10から20ミクロンが好適である。Each layer of the photoreceptor can be formed by vapor deposition or dispersion coating. The dispersion coating is performed using a spin coater, an applicator, a spray coater, a dip coater, a roller coater, a curtain coater, a bead coater, or the like, and drying is performed from room temperature to 200 ° C.
It is carried out in the range of 0 minutes to 6 hours under static or blowing conditions.
The thickness of the photosensitive layer after drying is 5 to 50 μm for a single-layer type photoreceptor, and 0.01 to 5 μm, preferably 0.1 to 1 μm for a multilayer type photoreceptor. Yes, the hole transport layer is suitably 5 to 50 microns, preferably 10 to 20 microns.
【0047】単層型感光体の感光層、積層型感光体の電
荷発生層もしくは正孔輸送層を形成する際に使用する樹
脂は広範な絶縁性樹脂から選択出来る。また、ポリ−N
−ビニルカルバゾール、ポリビニルアントラセンやポリ
シラン類などの有機光導電性ポリマーから選択出来る。
好ましくは、ポリビニルブチラール、ポリアリレート、
ポリカーボネート、ポリエステル、フェノキシ、アクリ
ル、ポリアミド、ウレタン、エポキシ、シリコン、ポリ
スチレン、ポリ塩化ビニル、塩酢ビ共重合体、フェノー
ルおよびメラミン樹脂等の絶縁性樹脂を挙げることが出
来る。電荷発生層もしくは正孔輸送層を形成するために
使用される樹脂は、電荷発生材料もしくは正孔輸送材料
に対して、100重量%以下が好ましいがこの限りでは
ない。樹脂は2種類以上組み合わせて使用しても良い。
また、必要があれば樹脂を使用しなくてもよい。また、
電荷発生層を蒸着、スパッタリング等の物理的成膜法に
より形成させることも出来る。蒸着、スパッタリング法
では、好ましくは10-5Toor以下の真空雰囲気下で
成膜することが望ましい。また、窒素、アルゴン、ヘリ
ウム等の不活性ガス中で成膜することも可能である。The resin used for forming the photosensitive layer of the single layer type photoreceptor or the charge generation layer or the hole transport layer of the laminated type photoreceptor can be selected from a wide range of insulating resins. In addition, poly-N
-Can be selected from organic photoconductive polymers such as vinylcarbazole, polyvinylanthracene and polysilanes;
Preferably, polyvinyl butyral, polyarylate,
Examples thereof include insulating resins such as polycarbonate, polyester, phenoxy, acrylic, polyamide, urethane, epoxy, silicon, polystyrene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, phenol and melamine resin. The resin used for forming the charge generation layer or the hole transport layer is preferably, but not limited to, 100% by weight or less based on the charge generation material or the hole transport material. Two or more resins may be used in combination.
Further, if necessary, the resin may not be used. Also,
The charge generation layer can also be formed by a physical film formation method such as evaporation or sputtering. In the vapor deposition and sputtering methods, it is desirable to form a film in a vacuum atmosphere of preferably 10 -5 Tool or less. It is also possible to form a film in an inert gas such as nitrogen, argon or helium.
【0048】電子写真感光体の各層を形成する際に使用
する溶剤は、下引き層や他の感光層に影響を与えないも
のから選択することが好ましい。具体的には、ベンゼ
ン、キシレン等の芳香族炭化水素、アセトン、メチルエ
チルケトン、シクロヘキサノン等のケトン類、メタノー
ル、エタノール等のアルコール類、酢酸エチル、メチル
セロソルブ等のエステル類、四塩化炭素、クロロホル
ム、ジクロロメタン、ジクロロエタン、トリクロロエチ
レン等の脂肪族ハロゲン化炭化水素類、クロルベンゼ
ン、ジクロルベンゼン等の芳香族ハロゲン化炭化水素
類、テトラヒドロフラン、ジオキサン等のエーテル類等
が用いられるがこれらに限られるものではない。The solvent used for forming each layer of the electrophotographic photosensitive member is preferably selected from those which do not affect the undercoat layer or other photosensitive layers. Specifically, aromatic hydrocarbons such as benzene and xylene, ketones such as acetone, methyl ethyl ketone and cyclohexanone, alcohols such as methanol and ethanol, esters such as ethyl acetate and methyl cellosolve, carbon tetrachloride, chloroform and dichloromethane But aliphatic halogenated hydrocarbons such as dichloroethane and trichloroethylene, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, and ethers such as tetrahydrofuran and dioxane are used, but are not limited thereto.
【0049】正孔輸送層は正孔輸送材料のみ、もしくは
正孔輸送材料を樹脂に溶解させた塗液を塗布することに
より形成される。本感光体に使用される正孔輸送材料
は、一般式[1]の化合物に加えて他の正孔輸送材料を
組み合わせて使用することもできる。一般式[1]の化
合物は、樹脂との相溶性が良く、結晶が析出しにくいの
で、感度、耐久性の向上のために有利である。The hole transport layer is formed by applying only the hole transport material or a coating solution obtained by dissolving the hole transport material in a resin. The hole transporting material used in the present photoreceptor can be used in combination with another hole transporting material in addition to the compound represented by the general formula [1]. The compound represented by the general formula [1] has good compatibility with the resin and is unlikely to precipitate crystals, and thus is advantageous for improving sensitivity and durability.
【0050】電子写真特性、画像特性等の向上のため
に、必要があれば基板と有機層の間に下引き層を設ける
ことができ、下引き層としてはポリアミド類、カゼイ
ン、ポリビニルアルコール、ゼラチン、ポリビニルブチ
ラール等の樹脂類、酸化アルミニウム等の金属酸化物な
どが用いられる。If necessary, an undercoat layer may be provided between the substrate and the organic layer to improve electrophotographic characteristics, image characteristics, and the like. Examples of the undercoat layer include polyamides, casein, polyvinyl alcohol, and gelatin. And resins such as polyvinyl butyral and metal oxides such as aluminum oxide.
【0051】本発明の材料は、有機EL素子もしくは電
子写真感光体等の正孔輸送材料としのみでなく、光電変
換素子、太陽電池、イメージセンサー等有機光導電材料
のいずれの分野においても好適に使用できる。The material of the present invention can be suitably used not only as a hole transport material for an organic EL device or an electrophotographic photosensitive member, but also in any field of an organic photoconductive material such as a photoelectric conversion device, a solar cell, and an image sensor. Can be used.
【0052】[0052]
【実施例】以下、本発明を実施例に基づきさらに詳細に
説明する。化合物(10)の合成方法 酢酸30部中に、2,2−ビス(4−オキソシクロヘキ
シル)プロパン7部、4,4−ジメチルトリフェニルア
ミン23部、およびメタンスルホン酸2部を入れ、10
5℃にて30時間加熱撹拌した。その後、500部の水
で希釈し、希水酸化ナトリウム水溶液で中和した。この
後、酢酸エチルで抽出を行い、濃縮し、シリカゲルを用
いたカラムクロマトグラフィーにより精製して黄色の蛍
光を有する粉末10部を得た。分子量分析、赤外線吸収
スペクトルの結果、化合物(10)であることを確認し
た。以下に生成物の元素分析結果を示す。 元素分析結果 C95H96N4として 計算値(%):C:88.24 H:7.43
N:4.33 実測値(%):C:88.51 H:7.28
N:4.21 この化合物の赤外吸収スペクトル(KBr錠剤法)を図
6に示す。The present invention will be described in more detail with reference to the following examples. Synthesis method of compound (10) In 30 parts of acetic acid, 7 parts of 2,2-bis (4-oxocyclohexyl) propane, 23 parts of 4,4-dimethyltriphenylamine, and 2 parts of methanesulfonic acid were added, and 10 parts of methanesulfonic acid were added.
The mixture was heated and stirred at 5 ° C. for 30 hours. Thereafter, the mixture was diluted with 500 parts of water and neutralized with a dilute aqueous sodium hydroxide solution. After that, extraction was performed with ethyl acetate, concentrated, and purified by column chromatography using silica gel to obtain 10 parts of a powder having a yellow fluorescence. As a result of molecular weight analysis and infrared absorption spectrum, it was confirmed to be Compound (10). The results of elemental analysis of the product are shown below. Calculated elemental analysis C 95 H 96 N 4 (% ): C: 88.24 H: 7.43
N: 4.33 Actual value (%): C: 88.51 H: 7.28
N: 4.21 The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
【0053】実施例1 洗浄したITO電極付きガラス板上に、トリス(8−ヒ
ドロキシキノリン)アルミニウム錯体、化合物(3)、
ポリ−N−ビニルカルバゾールを3:2:5の比率でク
ロロフォルムに溶解分散させ、スピンコーティング法に
より1000オングストロームの膜厚の発光層を得た。
その上に、マグネシウムと銀を10:1で混合した合金
で1500オングストロームの膜厚の電極を形成して図
1に示す有機EL素子を得た。この素子は、直流電圧5
Vで発光輝度110cd/m2、発光効率1.4lm/
Wの発光が得られた。Example 1 Tris (8-hydroxyquinoline) aluminum complex, compound (3),
Poly-N-vinylcarbazole was dissolved and dispersed in chloroform at a ratio of 3: 2: 5, and a light-emitting layer having a thickness of 1000 Å was obtained by spin coating.
An electrode having a thickness of 1500 angstroms was formed thereon using an alloy obtained by mixing magnesium and silver at a ratio of 10: 1 to obtain the organic EL device shown in FIG. This element has a DC voltage of 5
At 110 V, the emission luminance is 110 cd / m 2 , and the luminous efficiency is 1.4 lm /.
Light emission of W was obtained.
【0054】実施例2 洗浄したITO電極付きガラス板上に、N,N'―ジフ
ェニル―N,N'―(3―メチルフェニル)―1,1'―
ビフェニル―4,4'―ジアミンを真空蒸着して、30
0オングストロームの膜厚の正孔注入層を得た。次い
で、真空蒸着法により化合物(4)および[2−(4−
tert−ブチルフェニル)−5−(ビフェニル)−
1,3,4−オキサジアゾール]を1:1の比率で膜厚
500オングストロームの発光層を作成し、その上に、
マグネシウムと銀を10:1で混合した合金で1500
オングストロームの膜厚の電極を形成して図2に示す有
機EL素子を得た。正孔注入層および発光層は10-6T
orrの真空中で、基板温度室温の条件下で蒸着した。
この素子は、直流電圧5Vで発光輝度180cd/
m2、発光効率1.9lm/Wの発光が得られた。Example 2 N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'- was placed on a washed glass plate with an ITO electrode.
Biphenyl-4,4'-diamine is vacuum deposited to form 30
A hole injection layer having a thickness of 0 Å was obtained. Next, the compound (4) and [2- (4-
tert-butylphenyl) -5- (biphenyl)-
[1,3,4-oxadiazole] at a ratio of 1: 1 to form a light-emitting layer having a thickness of 500 angstroms.
1500 alloy with a 10: 1 mixture of magnesium and silver
An electrode having a thickness of Å was formed to obtain an organic EL device shown in FIG. The hole injection layer and the light emitting layer are 10 -6 T
Vapor deposition was performed at a substrate temperature of room temperature in a vacuum of orr.
This element emits light at a luminance of 180 cd /
m 2 , and luminescence with a luminous efficiency of 1.9 lm / W was obtained.
【0055】実施例3 洗浄したITO電極付きガラス板上に、化合物(10)
を真空蒸着して、300オングストロームの膜厚の正孔
注入層を得た。次いで、トリス(8−ヒドロキシキノリ
ン)アルミニウム錯体を真空蒸着して膜厚500オング
ストロームの発光層を作成し、その上に、マグネシウム
と銀を10:1で混合した合金で1500オングストロ
ームの膜厚の電極を形成して図2に示す有機EL素子を
得た。正孔注入層および発光層は10-6Torrの真空
中で、基板温度室温の条件下で蒸着した。この素子は、
直流電圧5Vで発光輝度450cd/m2、発光効率
4.3lm/Wの発光が得られた。Example 3 Compound (10) was placed on a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a thickness of 300 Å. Next, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light-emitting layer having a thickness of 500 angstroms, and an electrode having a thickness of 1500 angstroms made of an alloy obtained by mixing magnesium and silver at a ratio of 10: 1. Was formed to obtain an organic EL device shown in FIG. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 -6 Torr at a substrate temperature of room temperature. This element
Light emission with a luminance of 450 cd / m 2 and a luminous efficiency of 4.3 lm / W was obtained at a DC voltage of 5 V.
【0056】実施例4 洗浄したITO電極付きガラス板上に、化合物(11)
を真空蒸着して、膜厚300オングストロームの正孔注
入層を得た。次いで、真空蒸着法によりトリス(8−ヒ
ドロキシキノリン)アルミニウム錯体の膜厚200オン
グストロームの発光層を作成し、さらに真空蒸着法によ
り[2−(4−tert−ブチルフェニル)−5−(ビ
フェニル)−1,3,4−オキサジアゾール]の膜厚2
00オングストロームの電子注入層を得た。その上に、
マグネシウムと銀を10:1で混合した合金で膜厚15
00オングストロームの電極を形成して図3に示す有機
EL素子を得た。この素子は、直流電圧5Vで発光輝度
490cd/m2、発光効率4.2lm/Wの発光が得
られた。Example 4 Compound (11) was placed on a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a thickness of 300 Å. Next, a 200-Å-thick luminescent layer of a tris (8-hydroxyquinoline) aluminum complex was formed by vacuum evaporation, and [2- (4-tert-butylphenyl) -5- (biphenyl)-was formed by vacuum evaporation. 1,3,4-oxadiazole] film thickness 2
An electron injection layer of 00 Å was obtained. in addition,
An alloy of magnesium and silver mixed at a ratio of 10: 1 with a film thickness of 15
An organic EL device shown in FIG. 3 was obtained by forming a 00 Å electrode. This device emitted light with a luminance of 490 cd / m 2 and a luminous efficiency of 4.2 lm / W at a DC voltage of 5 V.
【0057】実施例5〜13 洗浄したITO電極付きガラス板上に、表2に示した化
合物をクロロホルムに溶解させ、スピンコーティング法
により膜厚50nmの正孔注入層を得た。次いで、トリ
ス(8−ヒドロキシキノリン)アルミニウム錯体を真空
蒸着して膜厚30nmの発光層を作成し、その上に、マ
グネシウムと銀を10:1で混合した合金で膜厚100
nmの電極を形成して図2に示す有機EL素子を得た。
発光層は10-8Torrの真空中で、基板温度室温の条
件下で蒸着した。この素子は、直流電圧5Vで表2に示
した発光性能を示した。Examples 5 to 13 The compounds shown in Table 2 were dissolved in chloroform on a washed glass plate with an ITO electrode, and a hole injection layer having a thickness of 50 nm was obtained by spin coating. Then, a tris (8-hydroxyquinoline) aluminum complex was vacuum-deposited to form a light-emitting layer having a thickness of 30 nm, and an alloy obtained by mixing magnesium and silver at a ratio of 10: 1 to a thickness of 100 nm.
2 nm was formed to obtain an organic EL device shown in FIG.
The light emitting layer was deposited in a vacuum of 10 -8 Torr at a substrate temperature of room temperature. This device exhibited the light emission performance shown in Table 2 at a DC voltage of 5 V.
【0058】[0058]
【表2】 [Table 2]
【0059】本実施例で示された全ての有機EL素子に
ついて、1mA/cm2で連続発光させたところ、10
00時間以上安定な発光を観測することができた。本発
明の有機EL素子は発光効率、発光輝度の向上と長寿命
化を達成するものであり、併せて使用される発光物質、
発光補助材料、正孔輸送材料、電子輸送材料、増感剤、
樹脂、電極材料等および素子作製方法を限定するもので
はない。For all the organic EL devices shown in this example, continuous light emission was performed at 1 mA / cm 2.
Stable light emission could be observed for 00 hours or more. The organic EL device of the present invention achieves luminous efficiency, improved luminous brightness and longer life, and a luminescent material used in combination therewith,
Luminescence auxiliary materials, hole transport materials, electron transport materials, sensitizers,
It does not limit the resin, the electrode material and the like, and the element manufacturing method.
【0060】実施例14 ε型銅フタロシアニン4g、化合物(2)2g、ポリエ
ステル樹脂(バイロン200:東洋防(株)製)14g
をテトラヒドロフラン80gと共にボールミルで5時間
分散した。この分散液をアルミニウム基板上に塗工、乾
燥して、図4に示す膜厚20ミクロンの単層型電子写真
感光体を作製した。Example 14 4 g of ε-type copper phthalocyanine, 2 g of compound (2), and 14 g of a polyester resin (Vylon 200: manufactured by Toyo Defense Co., Ltd.)
Was dispersed in a ball mill for 5 hours together with 80 g of tetrahydrofuran. This dispersion was coated on an aluminum substrate and dried to produce a single-layer electrophotographic photoreceptor having a thickness of 20 μm as shown in FIG.
【0061】実施例15 ジブロモアントアントロン6g、化合物(10)2g、
ポリエステル樹脂(バイロン200:東洋防(株)製)
12gをテトラヒドロフラン80gと共にボールミルで
5時間分散した。この分散液をアルミニウム基板上に塗
工、乾燥して、図4に示す膜厚20ミクロンの単層型電
子写真感光体を作製した。Example 15 6 g of dibromoanthanthrone, 2 g of compound (10)
Polyester resin (Byron 200: manufactured by Toyo Defense Co., Ltd.)
12 g was dispersed in a ball mill for 5 hours together with 80 g of tetrahydrofuran. This dispersion was coated on an aluminum substrate and dried to produce a single-layer electrophotographic photoreceptor having a thickness of 20 μm as shown in FIG.
【0062】実施例16 τ型無金属フタロシアニン2g、ポリビニルブチラール
樹脂(BH−3:積水化学(株)製)2gをテトラヒド
ロフラン96gと共にボールミルで2時間分散した。こ
の分散液をアルミニウム基板上に塗工、乾燥して、膜厚
0.3ミクロンの電荷発生層を作製した。次に化合物
(11)10g、ポリカーボネート樹脂(L−125
0;帝人化成(株)製)10gをジクロロメタン80g
に溶解した。この塗液を電荷発生層上に塗工、乾燥し
て、膜厚20ミクロンの正孔輸送層を形成し、図5に示
す積層型電子写真感光体を作製した。Example 16 2 g of τ-type metal-free phthalocyanine and 2 g of polyvinyl butyral resin (BH-3: manufactured by Sekisui Chemical Co., Ltd.) were dispersed together with 96 g of tetrahydrofuran in a ball mill for 2 hours. This dispersion was coated on an aluminum substrate and dried to form a charge generation layer having a thickness of 0.3 μm. Next, 10 g of compound (11) and a polycarbonate resin (L-125)
0; Teijin Chemicals Ltd.) 10 g with dichloromethane 80 g
Was dissolved. This coating solution was applied on the charge generation layer and dried to form a hole transport layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photosensitive member shown in FIG.
【0063】実施例17 N,N’−ビス(2,6−ジクロロフェニル)−3,
4,9,10−ペリレンジカルボキシイミド2g、ポリ
ビニルブチラール樹脂(BH−3:積水化学(株)製)
2gをテトラヒドロフラン96gと共にボールミルで2
時間分散した。この分散液をアルミニウム基板上に塗
工、乾燥して、膜厚0.3ミクロンの電荷発生層を作製
した。次に化合物(12)10g、ポリカーボネート樹
脂(L−1250;帝人化成(株)製)10gをジクロ
ロメタン80gに溶解した。この塗液を電荷発生層上に
塗工、乾燥して、膜厚20ミクロンの正孔輸送層を形成
し、図5に示す積層型電子写真感光体を作製した。Example 17 N, N'-bis (2,6-dichlorophenyl) -3,
2,9,10-Perylenedicarboximide 2 g, polyvinyl butyral resin (BH-3: manufactured by Sekisui Chemical Co., Ltd.)
2 g together with 96 g of tetrahydrofuran in a ball mill
Time dispersed. This dispersion was coated on an aluminum substrate and dried to form a charge generation layer having a thickness of 0.3 μm. Next, 10 g of the compound (12) and 10 g of a polycarbonate resin (L-1250; manufactured by Teijin Chemicals Ltd.) were dissolved in 80 g of dichloromethane. This coating solution was applied on the charge generation layer and dried to form a hole transport layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photosensitive member shown in FIG.
【0064】実施例18〜29 τ型無金属フタロシアニン2g、ポリビニルブチラール
樹脂(BH−3:積水化学(株)製)2gをテトラヒド
ロフラン96gと共にボールミルで2時間分散した。こ
の分散液をアルミニウム基板上に塗工、乾燥して、膜厚
0.3ミクロンの電荷発生層を作成した。次に表3に示
した化合物10g、ポリカーボネート樹脂(L−125
0;帝人化成(株)製)10gをジクロロメタン80g
に溶解した。この塗液を電荷発生層上に塗工、乾燥し
て、膜厚20ミクロンの電荷輸送層を形成し、図5に示
す積層型電子写真感光体を作製した。Examples 18 to 29 2 g of τ-type metal-free phthalocyanine and 2 g of polyvinyl butyral resin (BH-3: manufactured by Sekisui Chemical Co., Ltd.) were dispersed together with 96 g of tetrahydrofuran in a ball mill for 2 hours. This dispersion was applied on an aluminum substrate and dried to form a charge generating layer having a thickness of 0.3 μm. Next, 10 g of the compound shown in Table 3 and a polycarbonate resin (L-125)
0; Teijin Chemicals Ltd.) 10 g with dichloromethane 80 g
Was dissolved. This coating liquid was applied on the charge generating layer and dried to form a charge transporting layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photosensitive member shown in FIG.
【0065】電子写真感光体の電子写真特性は以下の方
法で測定した。静電複写紙試験装置(EPA−810
0;川口電機製作所(株)製)により、スタティックモ
ード2、コロナ帯電は−5.2(kV)、5(lux)
の白色光を照射して、初期表面電位(V0)、V0と2秒
間暗所に放置した時の表面電位(V2)の比(暗減衰
率:DDR2=V2/V0)、光露光後に帯電量が初期の
1/2まで減少する時間から半減露光量感度(E1/2)
および光露光3秒後の表面電位(VR3)を調べた。実
施例14〜29の電子写真感光体の電子写真特性を表3
に示す。The electrophotographic characteristics of the electrophotographic photosensitive member were measured by the following methods. Electrostatic copying paper tester (EPA-810
0; manufactured by Kawaguchi Electric Works, Ltd.), static mode 2, corona charging is -5.2 (kV), 5 (lux)
Irradiates white light, and the ratio of the initial surface potential (V 0 ), V 0 to the surface potential (V 2 ) when left in a dark place for 2 seconds (dark decay rate: DDR 2 = V 2 / V 0 ) , Half-exposure sensitivity (E 1/2 )
The surface potential (VR 3 ) after 3 seconds of light exposure was examined. Table 3 shows the electrophotographic characteristics of the electrophotographic photosensitive members of Examples 14 to 29.
Shown in
【0066】[0066]
【表3】 [Table 3]
【0067】1万回以上繰り返して電子写真特性を測定
したところ、本実施例で示された全ての電子写真感光体
について、安定な表面電位、感度を得ることができた。The electrophotographic characteristics were measured repeatedly 10,000 times or more. As a result, stable surface potential and sensitivity could be obtained for all the electrophotographic photosensitive members shown in this example.
【0068】[0068]
【発明の効果】本発明により、優れた正孔輸送能力を有
する化合物を得ることができた。本発明が提供した化合
物は、従来に比べて高発光効率、高輝度であり、長寿命
の有機EL素子および感度、正孔輸送特性、初期表面電
位、暗減衰率等の初期電子写真特性に優れ、繰り返し使
用に対する疲労も少ない電子写真感光体を得ることがで
きた。According to the present invention, a compound having an excellent hole transporting ability can be obtained. The compounds provided by the present invention have higher luminous efficiency and higher brightness than conventional ones, and have excellent long-life organic EL devices and excellent initial electrophotographic properties such as sensitivity, hole transport properties, initial surface potential, and dark decay rate. Thus, an electrophotographic photoreceptor having less fatigue due to repeated use could be obtained.
【図1】実施例で使用した有機EL素子の概略構造を表
す断面図FIG. 1 is a cross-sectional view illustrating a schematic structure of an organic EL device used in an example.
【図2】実施例で使用した有機EL素子の概略構造を表
す断面図FIG. 2 is a cross-sectional view illustrating a schematic structure of an organic EL element used in an example.
【図3】実施例で使用した有機EL素子の概略構造を表
す断面図FIG. 3 is a cross-sectional view illustrating a schematic structure of an organic EL element used in an example.
【図4】実施例で使用した電子写真感光体の概略構造を
表す断面図FIG. 4 is a cross-sectional view illustrating a schematic structure of an electrophotographic photosensitive member used in an example.
【図5】実施例で使用した電子写真感光体の概略構造を
表す断面図FIG. 5 is a cross-sectional view illustrating a schematic structure of an electrophotographic photosensitive member used in an example.
【図6】化合物10の赤外吸収スペクトルFIG. 6 is an infrared absorption spectrum of compound 10.
1.基板 2.電極A 3.正孔注入層 4.発光層 5.電子注入層 6.電極B 7.Al基板 8.感光層 9.電荷発生層 10.正孔輸送層 1. Substrate 2. Electrode A3. 3. Hole injection layer Light emitting layer 5. Electron injection layer 6. Electrode B 7. Al substrate 8. Photosensitive layer 9. Charge generation layer 10. Hole transport layer
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平3−94259(JP,A) 特開 平3−94258(JP,A) 特開 平3−5444(JP,A) 特開 平7−301926(JP,A) 特開 平4−279672(JP,A) 特開 平3−73961(JP,A) (58)調査した分野(Int.Cl.7,DB名) G03G 5/00 CA(STN)──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-3-94259 (JP, A) JP-A-3-94258 (JP, A) JP-A-3-5444 (JP, A) JP-A-7- 301926 (JP, A) JP-A-4-279672 (JP, A) JP-A-3-73961 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) G03G 5/00 CA ( STN)
Claims (5)
料。 一般式[1] 【化1】 [式中、R1〜R16は、水素原子、ハロゲン原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のチオアルコキシ基、
シアノ基、アミノ基、モノまたはジ置換アミノ基、水酸
基、メルカプト基、置換もしくは未置換のアリールオキ
シ基、置換もしくは未置換のアリールチオ基、置換もし
くは未置換の炭素環式芳香族環基、置換もしくは未置換
の複素環式芳香族環基、置換もしくは未置換の複素環基
を表し(隣接した置換基同士で置換もしくは未置換の脂
肪族式環、置換もしくは未置換の炭素環式芳香族環、置
換もしくは未置換の複素環式芳香族環基、置換もしくは
未置換の複素環を形成しても良い。)、X1、X2は、水
素原子、ハロゲン原子、置換もしくは未置換のアルキル
基、置換もしくは未置換のアルコキシ基、置換もしくは
未置換の炭素環式芳香族環基を表す(X1とX2とで置換
もしくは未置換の脂肪族脂環基を形成してもよ
い。)。]1. A hole transporting material represented by the following general formula [1]. General formula [1] [Wherein, R 1 to R 16 represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group,
Cyano group, amino group, mono- or di-substituted amino group, hydroxyl group, mercapto group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted carbocyclic aromatic ring group, substituted or Represents an unsubstituted heterocyclic aromatic ring group, a substituted or unsubstituted heterocyclic group (substituted or unsubstituted aliphatic ring, substituted or unsubstituted carbocyclic aromatic ring, A substituted or unsubstituted heterocyclic aromatic ring group or a substituted or unsubstituted heterocyclic ring may be formed.), X 1 and X 2 represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, Represents a substituted or unsubstituted alkoxy group or a substituted or unsubstituted carbocyclic aromatic ring group (X 1 and X 2 may form a substituted or unsubstituted aliphatic alicyclic group). ]
換もしくは未置換の低級アルキル基、置換もしくは未置
換の低級アルコキシ基である請求項1記載の正孔輸送材
料。2. The hole transport material according to claim 1, wherein R 1 to R 16 are a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted lower alkoxy group.
機化合物薄膜よりなる発光層を備えた有機エレクトロル
ミネッセンス素子において、少なくとも一層が請求項1
記載の正孔輸送材料を含有する層であることを特徴とす
る有機エレクトロルミネッセンス素子。3. An organic electroluminescence device comprising a light-emitting layer composed of one or more organic compound thin films between a pair of electrodes, wherein at least one layer is provided.
An organic electroluminescence device, which is a layer containing the hole transport material described in the above.
記載の有機エレクトロルミネッセンス素子。4. The light emitting layer according to claim 3, wherein at least one layer is a light emitting layer.
The organic electroluminescent device according to the above.
項3記載の有機エレクトロルミネッセンス素子。5. The organic electroluminescence device according to claim 3, wherein at least one layer is a hole injection layer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22141994A JP3261881B2 (en) | 1994-09-16 | 1994-09-16 | Hole transport material and its use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22141994A JP3261881B2 (en) | 1994-09-16 | 1994-09-16 | Hole transport material and its use |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0887121A JPH0887121A (en) | 1996-04-02 |
JP3261881B2 true JP3261881B2 (en) | 2002-03-04 |
Family
ID=16766450
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JP22141994A Expired - Fee Related JP3261881B2 (en) | 1994-09-16 | 1994-09-16 | Hole transport material and its use |
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JP (1) | JP3261881B2 (en) |
Families Citing this family (2)
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---|---|---|---|---|
JP3893869B2 (en) * | 2000-10-13 | 2007-03-14 | 富士ゼロックス株式会社 | Organic electroluminescence device |
JP4411258B2 (en) * | 2004-09-10 | 2010-02-10 | キヤノン株式会社 | Electrophotographic photosensitive member, electrophotographic apparatus, and process cartridge |
-
1994
- 1994-09-16 JP JP22141994A patent/JP3261881B2/en not_active Expired - Fee Related
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