JP2005116203A - Organic el display device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL display device in which positive hole excess or electron excess is suppressed by reducing a difference between the positive hole mobility of a positive hole transportation layer and the electron mobility of an electron transportation layer, and in which light emitting efficiency can be improved by nearly equalizing injection balance between a positive hole and an electron. <P>SOLUTION: Because a positive electrode 2, the positive hole transportation layer 3, a light emitting layer 4, the electron transportation layer 5, an electron injection layer 6, and a negative electrode 7 are laminated sequentially on a translucent glass substrate 1, and the positive hole transportation layer 3 and the electron transportation layer 5 joined to both sides of the light emitting layer 4 are formed of organic materials containing IV group elements other than carbon, the difference between the positive hole mobility of the positive hole transportation layer 3 and the electron mobility of the electron transportation layer 5 becomes smaller, and the positive hole mobility and the electron mobility become equal, and because the positive hole excess or the electron excess to the light emitting layer 4 is suppressed, the injection balance between the positive hole and the electron becomes equal, light emitting efficiency is improved, and the electric power consumption of the organic EL display device is reduced. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an organic EL display device using an organic EL material, and more particularly to an organic material that forms a hole transport layer and an electron transport layer that are bonded to both sides of a light emitting layer.

  As a current-controlled light-emitting device used for a display device, a device using electroluminescence (EL) or an injection-type light-emitting diode is known. Among them, a current control type EL (charge injection type EL, hereinafter also referred to as an organic light emitting element or organic EL) using an organic fluorescent material as a light emitting layer has a high luminance, a large area, a low manufacturing cost and a full color display. It is attracting attention as a possible display device.

  FIG. 12 is a cross-sectional view of an essential part for schematically explaining one structural example of the organic EL display device. This organic EL display device includes an anode AD formed of a transparent conductive film (thin film) such as ITO on a substrate SUB which is preferably a glass substrate, and a hole injection layer HIL made of a thin film of an organic material on the anode AD. A hole transport layer HTL, a light emitting layer EML, an electron transport layer ETL, an electron injection layer EIL, and a cathode KD serving as a light emission control electrode are sequentially stacked.

In the organic EL display device configured as described above, holes are transferred from the hole injection layer HIL to the light emitting layer EML via the hole transport layer HTL by applying a voltage between the cathode KD and the anode AD. (H ⁺ ) and electrons (e ⁻ ) injected from the electron injection layer EIL through the electron transport layer ETL into the light emitting layer EML are recombined to cause the light emitting layer EML to emit light, and the emitted light L from the substrate SUB. Is emitted.

  In addition, in this type of stacked organic EL display device, a structure in which an electron injection layer EIL for injecting electrons is not provided between the electron transport layer ETL and the cathode KD is used in order to improve the light emission efficiency.

  Since the organic EL display device configured as described above has energy levels different from each other as shown in FIG. 13 depending on the forming material constituting each organic layer, hole injection suitable for the light emitting layer EML containing the dopant Dop. By selecting the layer HIL, the hole transport layer HTL, the electron injection layer EIL, and the electron transport layer ETL and adjusting their film thicknesses, the injection balance of holes and electrons is controlled to be positive in the light emitting layer EML. The most common method is to efficiently recombine holes and electrons.

    Patent Document 1, Patent Document 2 and Patent Document 3 below use silole for the electron transport layer ETL and the light emitting layer EML as one example of improvement for improving the light emission efficiency for practical use of the organic EL display device. Thus, an organic EL display device that can realize high luminance light emission at a low voltage is disclosed.

  Patent Document 4 listed below discloses an organic EL display device in which luminous efficiency and heat resistance are improved by including an anthracene derivative in the light emitting layer EML.

  Further, Patent Document 5 below discloses an organic EL display device that can realize light emission efficiency and a long lifetime by including a distyrylarylene derivative in the light emitting layer EML.

  Patent Document 6 below discloses an EL display device that can realize a blue emission color by including a-SiC: H (hydrogenated amorphous silicon carbide) in the light emitting layer EML.

Note that these conventional techniques are disclosed in, for example, the following Patent Documents 1 to 6.
Japanese Patent Laid-Open No. 09-087616 JP 09-194487 A Japanese Patent Laid-Open No. 10-017860 International Patent Publication No. WO01 / 072673 JP 2000-273055 A Japanese Patent Laid-Open No. 06-204562

  However, in the organic EL display device configured as described above, the material for forming the hole injection layer HIL and the hole transport layer HTL is different from the material for forming the electron injection layer EIL and the electron transport layer ETL. Therefore, it is difficult to make the injection balance of holes and electrons equal to each other, resulting in an increase in power consumption and a decrease in lifetime due to a decrease in light emission efficiency of the organic EL display device.

In addition, the formation material of the hole injection layer HIL and the hole transport layer HTL has low radical anion stability, and the formation material of the electron transport layer ETL uses a material having low radical cation stability. Since the materials are different, the same element configuration causes an excess of holes (the number of holes> the number of electrons) in which the injection amount of holes h ⁺ is larger than the injection amount of electrons e ⁻ as shown in FIG. , holes h ⁺ of injected electrons than the amount e as shown in FIG. 15 ^- cause the injection amount is large becomes electron rich (electron number> number of holes), holes h ⁺ and electrons e ^- and injection balance of As a result, it is difficult to make them equivalent to each other. As a result, there is a problem in that power consumption increases due to a decrease in light emission efficiency of the organic EL display device, causing a reduction in lifetime.

  Further, a material for forming the hole injection layer HIL and the hole transport layer HTL and a material for forming the electron transport layer ETL for each of the red (R), green (G), and blue (B) colors of the pixel. Since they are different from each other, there is a problem that the cost of the forming material is increased and the manufacturing process is complicated.

  As another improvement example for improving the light emission efficiency, an organic EL display device in which holes and electrons are efficiently recombined by using a silane derivative, a germanium derivative or a tin derivative as the electron transport layer ETL. However, according to such a configuration, since the formation material of the hole transport layer ETL and the formation material of the electron transport layer ETL are different, the injection balance of holes and electrons is not equal, and as a result Similar to the above, there is a problem that the luminous efficiency is lowered.

  Therefore, the present invention has been made to solve the above-described conventional problems, the purpose of which is to reduce the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer, An object of the present invention is to provide an organic EL display device capable of improving luminous efficiency by suppressing excess holes or excess electrons and making the injection balance between holes and electrons substantially equal.

In order to achieve such an object, the organic EL display device according to the present invention is formed by sequentially laminating at least an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode on a translucent substrate. By forming the hole transport layer and the electron transport layer bonded to both sides of the layer with an organic material containing a group IV element other than carbon, the hole mobility of the hole transport layer and the electron mobility of the electron transport layer The hole mobility and the electron mobility become equal, and the hole excess or electron excess into the light emitting layer is suppressed, so that the injection balance of holes and electrons becomes equal, and the problem of the background art is reduced. Can be solved.

［式中、Ｘ及びＹは、それぞれ独立に炭素数１から６までの飽和もしくは不飽和の炭化水素基、アルコキシ基、アルケニルオキシ基、アルキニルオキシ基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロ環又はＸとＹが結合して飽和もしくは不飽和の環を形成した構造であり、Ｒ₁〜Ｒ₄は、それぞれ独立に水素、ハロゲン、置換もしくは無置換の炭素数１から６までのアルキル基、アルコキシ基、アリールオキシ基、パーフルオロアルキル基、パーフルオロアルコキシ基、アミノ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アゾ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニル基、スルフォニル基、スルファニル基、シリル基、カルバモイル基、アリール基、ヘテロ環基、アルケニル基、アルキニル基、ニトロ基、ホルミル基、ニトロソ基、ホルミルオキシ基、イソシアノ基、シアネート基、イソシアネート基、チオシアネート基、イソチオシアネート基、もしくはシアノ基または隣接した場合には置換もしくは無置換の環が縮合した構造である（但し、Ｒ₁及びＲ₄がフェニル基の場合、Ｘ及びＹは、アルキル基及びフェニル基ではなく、Ｒ₁及びＲ₄がチエニル基の場合、Ｘ及びＹは、一価炭化水素基を、Ｒ₂およびＲ₃は、アルキル基、アリール基、アルケニル基又はＲ₂とＲ₃が結合して環を形成する脂肪族基を同時に満たさない構造であり、Ｒ₁およびＲ₄がシリル基の場合、Ｒ₂、Ｒ₃、Ｘ及びＹは、それぞれ独立に炭素数１から６の一価炭化水素基又は水素原子でなく、Ｒ₁及びＲ₂でベンゼン環が縮合した構造の場合、Ｘ及びＹは、アルキル基及びフェニル基ではない）。］ In the above structure, at least one silacyclopentadiene derivative (cyclopentadiene derivative) represented by the following chemical formula 7 having excellent radical anion / cation stability and having the same hole and electron mobility as an organic material containing a group IV element other than carbon Since the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer is reduced by using a compound in which one C (carbon) of the 5-membered ring is replaced by Si (silicon), Hole mobility and electron mobility are equalized, and excess hole or electron excess to the light-emitting layer is suppressed, so that the injection balance of holes and electrons becomes equal, and the problems of the background art can be solved. .

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ]

［式中、Ｘ及びＹは、それぞれ独立に炭素数１から６までの飽和もしくは不飽和の炭化水素基、アルコキシ基、アルケニルオキシ基、アルキニルオキシ基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロ環又はＸとＹが結合して飽和もしくは不飽和の環を形成した構造であり、Ｒ₁〜Ｒ₄は、それぞれ独立に水素、ハロゲン、置換もしくは無置換の炭素数１から６までのアルキル基、アルコキシ基、アリールオキシ基、パーフルオロアルキル基、パーフルオロアルコキシ基、アミノ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アゾ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニル基、スルフォニル基、スルファニル基、シリル基、カルバモイル基、アリール基、ヘテロ環基、アルケニル基、アルキニル基、ニトロ基、ホルミル基、ニトロソ基、ホルミルオキシ基、イソシアノ基、シアネート基、イソシアネート基、チオシアネート基、イソチオシアネート基、もしくはシアノ基または隣接した場合には置換もしくは無置換の環が縮合した構造である（但し、Ｒ₁及びＲ₄がフェニル基の場合、Ｘ及びＹは、アルキル基及びフェニル基ではなく、Ｒ₁及びＲ₄がチエニル基の場合、Ｘ及びＹは、一価炭化水素基を、Ｒ₂およびＲ₃は、アルキル基、アリール基、アルケニル基又はＲ₂とＲ₃が結合して環を形成する脂肪族基を同時に満たさない構造であり、Ｒ₁およびＲ₄がシリル基の場合、Ｒ₂、Ｒ₃、Ｘ及びＹは、それぞれ独立に炭素数１から６の一価炭化水素基又は水素原子でなく、Ｒ₁及びＲ₂でベンゼン環が縮合した構造の場合、Ｘ及びＹは、アルキル基及びフェニル基ではない）。］ Further, in the above structure, at least one type of germanacyclopentadiene derivative represented by the following chemical formula 8 having excellent radical anion / cation stability and having the same hole and electron mobility as an organic material containing a group IV element other than carbon ( By using a compound in which one C (carbon) of a 5-membered ring of cyclopentadiene is replaced with Ge (germanium), the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer is reduced. Therefore, the hole mobility and the electron mobility become equal, and the excess of holes or the excess of electrons to the light emitting layer is suppressed, so that the injection balance of holes and electrons becomes equal and the problems of the background art are solved. Can do.

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ]

［式中、Ｘ及びＹは、それぞれ独立に炭素数１から６までの飽和もしくは不飽和の炭化水素基、アルコキシ基、アルケニルオキシ基、アルキニルオキシ基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロ環又はＸとＹが結合して飽和もしくは不飽和の環を形成した構造であり、Ｒ₁〜Ｒ₄は、それぞれ独立に水素、ハロゲン、置換もしくは無置換の炭素数１から６までのアルキル基、アルコキシ基、アリールオキシ基、パーフルオロアルキル基、パーフルオロアルコキシ基、アミノ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アゾ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニル基、スルフォニル基、スルファニル基、シリル基、カルバモイル基、アリール基、ヘテロ環基、アルケニル基、アルキニル基、ニトロ基、ホルミル基、ニトロソ基、ホルミルオキシ基、イソシアノ基、シアネート基、イソシアネート基、チオシアネート基、イソチオシアネート基、もしくはシアノ基または隣接した場合には置換もしくは無置換の環が縮合した構造である（但し、Ｒ₁及びＲ₄がフェニル基の場合、Ｘ及びＹは、アルキル基及びフェニル基ではなく、Ｒ₁及びＲ₄がチエニル基の場合、Ｘ及びＹは、一価炭化水素基を、Ｒ₂およびＲ₃は、アルキル基、アリール基、アルケニル基又はＲ₂とＲ₃が結合して環を形成する脂肪族基を同時に満たさない構造であり、Ｒ₁およびＲ₄がシリル基の場合、Ｒ₂、Ｒ₃、Ｘ及びＹは、それぞれ独立に炭素数１から６の一価炭化水素基又は水素原子でなく、Ｒ₁及びＲ₂でベンゼン環が縮合した構造の場合、Ｘ及びＹは、アルキル基及びフェニル基ではない）。］ Further, in the above structure, at least one stanacyclopentadiene derivative (cyclohexane) represented by the following chemical formula 9 having excellent radical anion / cation stability and having the same hole and electron mobility as an organic material containing a group IV element other than carbon. By using a compound in which one C (carbon) of pentadiene 5-membered ring is replaced with Sn (tin), the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer is reduced. Since hole mobility and electron mobility become equal, and excessive hole or electron excess to the light emitting layer is suppressed, the injection balance of holes and electrons becomes equal, which can solve the problems of the background art it can.

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ]

［式中、Ｒ１，Ｒ２，Ｒ３は、それぞれ独立に水素、ハロゲン、置換もしくは無置換の炭素数１から６までのアルキル基、アルコキシ基、アリールオキシ基、パーフルオロアルキル基、パーフルオロアルコキシ基、アミノ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アゾ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニル基、スルフォニル基、スルファニル基、シリル基、カルバモイル基、アリール基、ヘテロ環基、アルケニル基、アルキニル基、ニトロ基、ホルミル基、ニトロソ基、ホルミルオキシ基、イソシアノ基、シアネート基、イソシアネート基、チオシアネート基、イソチオシアネート基、もしくはシアノ基または隣接した場合には置換もしくは無置換の環が縮合した構造である。］ Another organic EL display device according to the present invention is formed by sequentially laminating at least an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode on a translucent substrate, and is bonded to both sides of the light emitting layer. By forming the hole transport layer and the electron transport layer with a borane derivative represented by the following chemical formula 10 (a compound in which three functional groups (hydrocarbon molecules represented by R) are bonded to B (boron)), Since the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer is reduced, the hole mobility and the electron mobility become equal, and the excess of holes or the excess of electrons to the light emitting layer is suppressed. The injection balance of holes and electrons becomes equal, and the problems of the background art can be solved.

[Wherein R1, R2 and R3 are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, Amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, Sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, isocyanate group, thiocyanate group Isothiocyanate group or when a cyano group, or adjacent, is a structure that substituted or unsubstituted ring is fused. ]

［式中、Ｘは、それぞれ独立に炭素数１から６までの飽和もしくは不飽和の炭化水素基、アルコキシ基、アルケニルオキシ基、アルキニルオキシ基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロ環を形成した構造であり、Ｒ₁〜Ｒ₄は、それぞれ独立に水素、ハロゲン、置換もしくは無置換の炭素数１から６までのアルキル基、アルコキシ基、アリールオキシ基、パーフルオロアルキル基、パーフルオロアルコキシ基、アミノ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アゾ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニル基、スルフォニル基、スルファニル基、シリル基、カルバモイル基、アリール基、ヘテロ環基、アルケニル基、アルキニル基、ニトロ基、ホルミル基、ニトロソ基、ホルミルオキシ基、イソシアノ基、シアネート基、イソシアネート基、チオシアネート基、イソチオシアネート基、もしくはシアノ基または隣接した場合には置換もしくは無置換の環が縮合した構造である（但し、Ｒ₁及びＲ₄がフェニル基の場合、Ｘは、アルキル基及びフェニル基ではなく、Ｒ₁及びＲ₄がチエニル基の場合、Ｘは、一価炭化水素基を、Ｒ₂およびＲ₃は、アルキル基、アリール基、アルケニル基又はＲ₂とＲ₃が結合して環を形成する脂肪族基を同時に満たさない構造であり、Ｒ₁およびＲ₄がシリル基の場合、Ｒ₂、Ｒ₃、Ｘは、それぞれ独立に炭素数１から６の一価炭化水素基又は水素原子でなく、Ｒ₁及びＲ₂でベンゼン環が縮合した構造の場合、Ｘは、アルキル基及びフェニル基ではない）。］ In the above structure, by using a boracyclopentadiene derivative represented by the following chemical formula 11 as a borane derivative (a compound in which one C (carbon) of a 5-membered ring of cyclopentadiene is replaced with B (boron)), hole transport is performed. Since the difference between the hole mobility of the layer and the electron mobility of the electron transport layer is reduced, the hole mobility and the electron mobility become equal, and the hole excess or the electron excess to the light emitting layer is suppressed. The injection balance of holes and electrons becomes equal, and the problems of the background art can be solved.

[In the formula, each X is independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group. R _{1 to} R ₄ each independently represents hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, Perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl Group, sulfonyl group, sulf Nyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group Or a cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent to each other (provided that R ₁ and R ₄ are phenyl groups, X is not an alkyl group or a phenyl group, but R ₁ and When R ₄ is a thienyl group, X is a monovalent hydrocarbon group, R ₂ and R ₃ are an alkyl group, an aryl group, an alkenyl group, or an aliphatic group in which R ₂ and R ₃ are combined to form a ring the a structure that does not simultaneously satisfy, when R ₁ and R ₄ is a silyl group, R _2, R _3, X are each independently from 1 to 6 carbon atoms monovalent hydrocarbon group or a hydrogen source But, if the structure in which a benzene ring is condensed with R ₁ and R _2, X is not alkyl and phenyl groups). ]

In addition, in the above configuration, by using MAB represented by the following chemical formula 12 as the borane derivative, the difference between the hole mobility of the hole transport layer and the electron mobility of the electron transport layer is reduced. In addition, since the electron mobility becomes equal, and the excess of holes or electrons in the light emitting layer is suppressed, the injection balance of holes and electrons becomes equal, and the problems of the background art can be solved.

  It should be noted that the present invention is not limited to the above-described configurations and the configurations described in the embodiments described later, and it goes without saying that various modifications can be made without departing from the technical idea of the present invention. .

According to the organic EL display device of the present invention, the positive hole transport layer is formed by forming the hole transport layer and the electron transport layer bonded to both sides of the light emitting layer with an organic material containing a group IV element other than carbon. Since the difference between the hole mobility and the electron mobility of the electron transport layer is reduced, the hole mobility and the electron mobility become equal, and the hole excess or electron excess to the light emitting layer is suppressed. The injection balance can be equalized, the luminous efficiency can be improved, and the power consumption of the organic EL display device can be reduced.

  In addition, according to the organic EL display device of the present invention, it is possible to prevent material deterioration caused by excess holes or excess electrons, so that the lifetime of the organic EL display device can be extended.

  Furthermore, according to the organic EL display device of the present invention, since the hole transport layer and the electron transport layer can be formed of the same organic material, the organic material can be made common, thereby reducing the material cost and reducing the organic cost. An extremely excellent effect such as simplification of the manufacturing process of the EL display device can be obtained.

  In addition, according to another organic EL display device according to the present invention, the hole transport layer and the electron transport layer that are bonded to both sides of the light emitting layer are formed of a borane derivative, thereby obtaining exactly the same effect as the above effect. It is done.

  Hereinafter, specific embodiments of the present invention will be described in detail with reference to the drawings of the examples.

  FIG. 1 is an enlarged cross-sectional view of a main part for explaining a configuration according to an embodiment of an organic EL display device according to the present invention based on a manufacturing process. First, as shown in FIG. 1, an ITO (Indium Tin Oxide) film having a thickness of about 150 nm is formed on a translucent non-alkali glass substrate 1 having a thickness of about 1.1 mm by vacuum deposition, and then a photolithography method is used. Then, a part is etched and patterned to form a light-transmitting anode 2 to be a pixel portion.

Subsequently, the alkali-free glass substrate 1 on which the anode 2 is formed is immersed in cleaning water of isopropyl alcohol, acetone, and pure water, respectively, and is subjected to ultrasonic cleaning for about 10 minutes and UV ozone for about 10 minutes. Process. Next, a silacyclopentadiene derivative having excellent radical anion / cation stability as an organic material containing a group IV element other than carbon on the anode 2 serving as a substrate pixel portion, and having the same hole and electron mobility, for example, 1-allyl- 1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) is formed to a thickness of about 70 nm by vacuum deposition to form the hole transport layer 3.

  Next, as the green light emitting material, for example, tris (8-hydroxyquinolino) aluminum (Alq) is formed on the hole transport layer 3 to a thickness of about 60 nm by vacuum deposition to form the light emitting layer 4. Subsequently, 1-allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) similar to the above is formed on the light emitting layer 4 to a thickness of about 70 nm by vacuum evaporation, and electron transport is performed. Layer 5 is formed.

Finally, lithium fluoride (LiF) is deposited on the electron transport layer 5 to a thickness of about 0.7 nm by vacuum deposition to form the electron injection layer 6, and then aluminum (Al) is deposited by vacuum deposition. The cathode 7 is formed by forming a film with a thickness of about 200 nm. These vapor deposition films are formed by a vacuum vapor deposition apparatus configured by connecting a plurality of chambers set to a vacuum degree of about 10 ⁻⁶ torr to a transport mechanism.

By applying a DC voltage of about 6 V between the anode 2 and the cathode 7 in the glove box, green light emission having a luminance of about 800 cd / m ² was obtained. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

In such a configuration, as shown in FIG. 1, it is ideal that the film thickness T _ETL of the electron transport layer 5 and the film thickness T _HTL of the hole transport layer 3 are equal (T _ETL = T _HTL ). _Specifically , T _ETL and T _HTL ≧ 1 nm, and T _ETL and T _HTL ≦ 500 nm are set. Further, the material for forming the hole transport layer 3 and the electron transport layer 5 is shared by using 1-allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS), so that FIG. As shown in FIG. 3, the energy difference between the anode 2 and the hole transport layer 3 and the energy difference between the cathode 7 and the electron transport layer 5 are made equal to each other to optimize the film thickness. The injection balance of holes h ⁺ and electrons e ⁻ can be made equal.

According to this structure, holes h ⁺ or electron e ^- excess injection is suppressed, holes h ⁺ and electrons e ^- Since injection balance between equals, holes h ⁺ and electrons e ^- and is Recombined with high efficiency. In addition, since an organic material excellent in radical anion / cation stability is used, excess holes or excess electrons do not occur, so that the formation materials of the hole transport layer 3 and the electron transport layer 5 are deteriorated due to this. This helps prevent longevity.

  Further, by adding the dopant Dop1 to the hole transport layer 3 and the electron transport layer 5 respectively, carriers may move in two bandwidths as shown in FIG. Therefore, higher efficiency and longer life can be obtained.

1-Allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) used as a material for forming the hole transport layer 3 and the electron transport layer 5 in Example 1 was replaced with 1-hydroxy-1, An organic EL display device was produced in the same manner as described above except that 2,3,4,5-pentaphenylsilacyclopentadiene was used. A green light emission with a luminance of about 700 cd / m ² was obtained by applying a DC voltage of about 6 V between the anode 2 and the cathode 7 to the organic EL display device thus fabricated. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

1-allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) used as a material for forming the hole transport layer 3 and the electron transport layer 5 in Example 1 was replaced with 1,1-dimethyl- An organic EL display device was produced by the same method as described above except that 2,3,4,5-tetraphenylgermacyclopentadiene (TPG) was used. A green light emission with a luminance of about 700 cd / m ² was obtained by applying a DC voltage of about 6 V between the anode 2 and the cathode 7 to the organic EL display device thus fabricated. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

1,1-Dimethyl-2,3,4,5-tetraphenylgermacyclopentadiene (TPG) used as a material for forming the hole transport layer 3 and the electron transport layer 5 in Example 3 is 9,9′-stana. An organic EL display device was produced by the same method as described above except that spirobifluorene was used. A green light emission with a luminance of about 700 cd / m ² was obtained by applying a DC voltage of about 6 V between the anode 2 and the cathode 7 to the organic EL display device thus fabricated. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

1,1-dimethyl-2,3,4,5-tetraphenylgermacyclopentadiene (TPG) used as a material for forming the hole transport layer 3 and the electron transport layer 5 in Example 3 is 9,9′-germa. An organic EL display device was produced by the same method as described above except that spirobifluorene was used. By applying a DC voltage of about 6 V between the anode 2 and the cathode 7 to the organic EL display device thus manufactured, green light emission with a luminance of about 800 cd / m ² was obtained. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

  1-allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) and 1-hydroxy-1,2,3, are formed on the anode 2 serving as the substrate pixel portion used in Example 1 above. 4,5-Pentaphenylsilacyclopentadiene is co-evaporated by a vacuum deposition method to form a film having a thickness of about 70 nm to form the hole transport layer 3.

  Next, tris (8-hydroxyquinolino) aluminum (Alq) is deposited on the hole transport layer 3 to a thickness of about 60 nm as a green light emitting material by a vacuum deposition method to form the light emitting layer 4. Subsequently, the same 1-allyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (APS) and 1-hydroxy-1,2,3,4,5-penta are formed on the light emitting layer 4 as described above. The electron transport layer 5 is formed by co-evaporating phenylsilacyclopentadiene with a vacuum deposition method to a thickness of about 70 nm.

  Next, lithium fluoride (LiF) is deposited to a thickness of about 0.7 nm by vacuum deposition to form the electron injection layer 6, and then aluminum (Al) is subsequently deposited to a thickness of about 200 nm by vacuum deposition. The cathode 7 is formed by forming a film.

The organic EL display device thus formed was applied with a DC voltage of about 6 V between the anode 2 and the cathode 7 in a glove box to obtain green light emission with a luminance of about 800 cd / m ² . The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

  FIG. 5 is an enlarged cross-sectional view of a main part for explaining the configuration of another embodiment of the organic EL display device according to the present invention based on the manufacturing process. First, as shown in FIG. 5, an ITO (Indium Tin Oxide) film having a thickness of about 150 nm is formed on a light-transmitting non-alkali glass substrate 1 having a thickness of about 1.1 mm by vacuum deposition, and then a photolithography method is used. Then, a part is etched and patterned to form a light-transmitting anode 2 to be a pixel portion.

  Subsequently, the alkali-free glass substrate 1 on which the anode 2 is formed is immersed in cleaning water of isopropyl alcohol, acetone, and pure water, respectively, and is subjected to ultrasonic cleaning for about 10 minutes and UV ozone for about 10 minutes. Process. Next, a hole injecting layer 8 is formed by depositing CuPc to a thickness of about 60 nm on the anode 2 serving as the substrate pixel portion by vacuum deposition.

  Next, α-NPD (α-diphenylnaphthyldiamine) and tris (8-hydroxyquinolino) aluminum (Alq) are co-deposited on the hole injection layer 8 by a vacuum evaporation method to a thickness of about 40 nm. The film is formed to form the hole transport layer 3. Thereafter, tris (8-hydroxyquinolino) aluminum (Alq) is deposited on the hole transport layer 3 as a green light emitting material to a thickness of about 60 nm by a vacuum deposition method to form the light emitting layer 4. Subsequently, α-NPD (α-diphenylnaphthyldiamine) and tris (8-hydroxyquinolino) aluminum (Alq) similar to the above are co-deposited on the light emitting layer 4 by a vacuum evaporation method to a thickness of about 40 nm. The electron transport layer 5 is formed by forming a film.

  Finally, after forming an electron injection layer 6 by depositing lithium fluoride (LiF) to a thickness of about 0.7 nm by vacuum vapor deposition under vacuum, aluminum (Al) is subsequently deposited to a thickness of about 200 nm by vacuum vapor deposition. The cathode 7 is formed by forming a film to a thickness.

The organic EL display device thus formed was applied with a DC voltage of about 6 V between the anode 2 and the cathode 7 in a glove box to obtain green light emission with a luminance of about 800 cd / m ² . The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

An organic EL display device was prepared in the same manner as described above except that the borane derivative was replaced with a boracyclopentadiene derivative or MBA instead of the material for forming the hole transport layer 3 and the electron transport layer 5 described in the above-described embodiments. Produced. By applying a DC voltage of about 6 V between the anode 2 and the cathode 7 to the organic EL display device thus manufactured, green light emission with a luminance of about 800 cd / m ² was obtained. The luminance half time of about 100 cd / m ² at room temperature was about 10,000 hours or more.

In such a configuration, by forming the hole transport layer 3 and the electron transport layer 5 using a borane derivative, the above-described silacyclopentadiene derivative having an electron mobility of 1E-3 to 1E-4 cm ² / Vs is used. MAB, which is a borane derivative, has a hole mobility of 1.2E-2 cm ² / Vs and an electron mobility of 1.2E-3 cm ² / Vs, and an extremely high mobility can be obtained. It was.

  As still another embodiment of the organic EL display device according to the present invention, the hole transport layer is formed of the above-described borane derivative, and the electron transport layer is any one of a silacyclopentadiene derivative, a germanacyclopentadiene derivative, and a stanacyclopentadiene derivative. Even if the hole transport layer and the electron transport layer are formed by a combination of a single element of the above-mentioned various derivatives or a combination of composites, the same effect as described above may be formed. It goes without saying that can be obtained.

  FIGS. 6 to 11 are main part sectional views showing configurations according to other examples of the organic EL display device according to the present invention. The same parts as those in the above-mentioned drawings are denoted by the same reference numerals, and the description thereof is omitted. To do. In these figures, the points different from the figures described above are injected from the anode 2 between the light emitting layer 4 and the hole transport layer 3 and the electron transport layer 5 respectively bonded to both sides in FIG. Holes and electrons are provided by providing a hole blocking layer 9 that prevents penetration of holes into the light emitting layer 4 and an electron blocking layer 10 that prevents penetration of electrons injected from the cathode 7 into the light emitting layer 4. It goes without saying that the same effect as described above can be obtained even if it is applied to an organic EL display device configured to control the injection balance.

  Further, in FIG. 7, in the configuration of FIG. 5, a hole blocking layer 9 is provided only between the light emitting layer 4 and the electron transport layer 5, so that holes injected from the anode 2 penetrate the light emitting layer 4. Even when applied to an organic EL display device configured to block and control the injection balance of holes and electrons, the same effect as described above can be obtained.

  In FIG. 8, when the hole transport layer 3 and the electron transport layer 5 are formed of different kinds of organic materials in the configuration of FIG. 7, different materials are mixed and combined to form the hole transport layer 3 ′. Even when applied to an organic EL display device configured to form the electron transport layer 5 ', the same effect as described above can be obtained.

  9, 10, and 11 correspond to the above-described FIGS. 6, 7, and 8, respectively. The difference from these figures is that the electron injection layer 6 and the hole injection layer 8 are provided. Even if the organic material to be formed is applied to an organic EL display device configured by sharing the same organic material, the same effect as described above can be obtained.

It is principal part sectional drawing which shows the structure by one Example of the organic electroluminescent display apparatus by this invention. It is a figure which shows the energy level of the organic electroluminescent display apparatus of FIG. It is a figure which shows the carrier balance of the organic electroluminescent display apparatus of FIG. It is a figure which shows an energy level when a dopant is added to the positive hole transport layer and electron transport layer of the organic electroluminescence display of FIG. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure by the other Example of the organic EL display apparatus by this invention. It is principal part sectional drawing which shows the structure of the conventional organic electroluminescence display. It is a figure which shows the energy level of the organic electroluminescence display of FIG. It is a figure which shows the carrier balance of the organic electroluminescence display of FIG. It is a figure which shows the carrier balance of the organic electroluminescence display of FIG.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 ... Glass substrate, 2 ... Anode, 3 ... Hole transport layer, 3 '... Hole transport layer, 4 ... Light emitting layer, 5 ... Electron transport layer, 5' -Electron transport layer, 6 ... electron injection layer, 7 ... cathode, 8 ... hole injection layer, 9 ... hole block layer, 10 ... electron block layer.

Claims (7)

In an organic EL display device formed by sequentially laminating at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode on a light transmitting substrate,
An organic EL display device, wherein the hole transport layer and the electron transport layer are formed of an organic material containing a group IV element other than carbon. 2. The organic EL display device according to claim 1, wherein at least one type of silacyclopentadiene derivative represented by the following chemical formula 1 is used as the organic material.

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ] 2. The organic EL display device according to claim 1, wherein at least one kind of germanacyclopentadiene derivative represented by the following chemical formula 2 is used as the organic material.

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ] 2. The organic EL display device according to claim 1, wherein at least one stanacyclopentadiene derivative represented by the following chemical formula 3 is used as the organic material.

[Wherein, X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, substituted or unsubstituted It is a substituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R _{1 to} R ₄ are each independently hydrogen, halogen, substituted or unsubstituted carbon atoms of 1 to 6 Alkyl group, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, aryl Carbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyl Xy group, sulfinyl group, sulfonyl group, sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, Isocyanate group, thiocyanate group, isothiocyanate group, or cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent (provided that when R ₁ and R ₄ are phenyl groups, X and Y are When R ₁ and R ₄ are not thienyl groups but alkyl groups and phenyl groups, X and Y are monovalent hydrocarbon groups, R ₂ and R ₃ are alkyl groups, aryl groups, alkenyl groups or R ₂ R ₃ bonded to is a structure that does not satisfy the aliphatic group simultaneously forming a ring, when R ₁ and R ₄ is a silyl group, R _2, R _3, And Y are each independently rather a monovalent hydrocarbon group or a hydrogen atom from 1 to 6 carbon atoms, for structures combined benzene ring is condensed with R ₁ and R _2, X and Y, the alkyl group and a phenyl group Absent). ] In an organic EL display device formed by sequentially laminating at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode on a light transmitting substrate,
An organic EL display device using at least one kind of borane derivative represented by the following chemical formula 4 as an organic material for the hole transport layer and the electron transport layer.

[Wherein R1, R2 and R3 are each independently hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, alkoxy group, aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, Amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, Sulfanyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, isocyanate group, thiocyanate group Isothiocyanate group or when a cyano group, or adjacent, is a structure that substituted or unsubstituted ring is fused. ] 6. The organic EL display device according to claim 5, wherein the borane derivative is a boracyclopentadiene derivative represented by the following chemical formula (5).

[In the formula, each X is independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group. R _{1 to} R ₄ each independently represents hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, Perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl Group, sulfonyl group, sulf Nyl group, silyl group, carbamoyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, nitro group, formyl group, nitroso group, formyloxy group, isocyano group, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group Or a cyano group or a structure in which a substituted or unsubstituted ring is condensed when adjacent to each other (provided that R ₁ and R ₄ are phenyl groups, X is not an alkyl group or a phenyl group, but R ₁ and When R ₄ is a thienyl group, X is a monovalent hydrocarbon group, R ₂ and R ₃ are an alkyl group, an aryl group, an alkenyl group, or an aliphatic group in which R ₂ and R ₃ are combined to form a ring the a structure that does not simultaneously satisfy, when R ₁ and R ₄ is a silyl group, R _2, R _3, X are each independently from 1 to 6 carbon atoms monovalent hydrocarbon group or a hydrogen source But, if the structure in which a benzene ring is condensed with R ₁ and R _2, X is not alkyl and phenyl groups). ] 6. The organic EL display device according to claim 5, wherein the borane derivative is MAB represented by the following chemical formula (6).

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