JP2010141359A - Organic electroluminescent device and light emitting device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent device which has a high fluorescence yield, and excellent red color purity, high brightness and stable red luminescence using a compound excellent also in heat stability. <P>SOLUTION: In the organic electroluminescent device, on a glass substrate 1, an ITO transparent electrode 2, a hole transport layer 6, an electron transport layer 7, and a metal electrode 3 are laminated in this order, the hole transport layer 6 and/or the electron transport layer 7 consist of an aminostyryl compound expressed with general formula [I], and a hole blocking layer 30 is provided between the hole transport layer 6 and the electron transport layer 7. In the general formula [I] where X<SP>1</SP>is aryl group, such as phenyl group with substituent, such as nitro group, and Y<SP>1</SP>and Y<SP>2</SP>are groups having aminophenyl group, etc. in their skeletons. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element (organic EL element) in which an organic layer having a light emitting region is provided between an anode and a cathode, and a light emitting device such as a display device using the same.

  Lightweight and high-efficiency flat panel displays have been actively researched and developed for display on computers and televisions, for example.

  First, a cathode ray tube (CRT) is currently used most frequently as a display because of its high luminance and good color reproducibility, but it has a problem that it is bulky, heavy, and consumes high power.

  In addition, liquid crystal displays such as active matrix drive have been commercialized as lightweight and highly efficient flat panel displays. However, liquid crystal displays have a narrow viewing angle and are not self-luminous. However, there is a problem that the power consumption of the high-definition video signal is large and that the high-definition high-speed video signal expected to be put into practical use in the future does not have sufficient response performance. In particular, it is difficult to produce a display with a large screen size, and there are problems such as high cost.

  As an alternative to this, there is a possibility of a display using light-emitting diodes, but there are problems such as high manufacturing cost and difficulty in forming a matrix structure of light-emitting diodes on one substrate. As a low-priced display candidate to replace, there is a big problem until practical use.

  Recently, an organic electroluminescent element (organic EL element) using an organic light emitting material has attracted attention as a flat panel display that can solve these problems. That is, by using an organic compound as a light-emitting material, it is expected to realize a flat panel display that is self-luminous, has a high response speed, and has no viewing angle dependency.

  The structure of the organic electroluminescent element is such that an organic thin film containing a light emitting material that emits light by current injection is formed between a light transmitting positive electrode and a metal cathode. CW Tang, SA Van Slyke, et al., In Applied Physics Letters, Vol. 51, No. 12, pp. 913-915 (1987), reported that organic thin films consist of a thin film made of a hole transporting material and a thin film made of an electron transporting material. As a two-layer structure, an element structure was developed that emits light by recombination of holes and electrons injected from each electrode into the organic film (single heterostructure organic EL element).

  In this element structure, either the hole transport material or the electron transport material serves as the light emitting material, and light emission occurs in a wavelength band corresponding to the energy gap between the ground state and the excited state of the light emitting material. By adopting such a two-layer structure, the driving voltage was greatly reduced and the luminous efficiency was improved.

  Then, as described in a research report published in Japanese Journal of Applied Physics Vol. 27, No. 2, pages L269-L271 (1988) by C. Adachi, S. Tokita, T. Tsutsui, S. Saito, etc. A three-layer structure (a double heterostructure organic EL device) of a hole transport material, a light-emitting material, and an electron transport material was developed. Furthermore, Journal of Applied Physics Vol. 65, No. 9, 3610 from CW Tang, SA Van Slyke, CH Chen, etc. As described in a research report published on page 3616 (1989), an element structure in which a light emitting material is included in an electron transport material has been developed. These studies have verified the possibility of light emission at low voltage and high brightness, and research and development have been very active in recent years.

  It can be said that the organic compound used for the light emitting material has an advantage that the emission color can be arbitrarily changed by changing the molecular structure in theory. Therefore, by applying molecular design, aligning the three colors of R (red), G (green), and B (blue) with good color purity required for full-color displays is less than thin film EL devices using inorganic materials. It can be said that it is easy.

However, there are actually problems that need to be solved even in organic electroluminescent devices. Development of a stable, high-brightness red light-emitting element is difficult, and as an electron transport material currently reported, tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) and DCM [4-dicyanomethylene-6- ( p-Dimethylaminostyryl) -2-methyl-4H-pyran] is an example of red light emission (non-patent document 1 described later). However, neither luminance nor reliability is satisfactory as a display material. .

In addition, BSB-BCN reported by T. Tsutsui and DU Kim in Non-Patent Document 2 described later achieves a high luminance of 1000 cd / m ² or more, but has full chromaticity as red corresponding to full color. Not a thing.

  In addition, the realization of a red light-emitting element that has high brightness, is stable, and has high color purity is desired.

  Further, in Patent Document 1 described later, it is proposed to use a specific distyryl compound as an organic electroluminescent material, but the target emission color is blue and not for red.

  An object of the present invention is to provide an organic electroluminescence device having a high fluorescence yield, a compound having excellent thermal stability, good red color purity, high luminance and stable red emission. It is in.

  Another object of the present invention is to promote organic recombination of holes and electrons in a light emitting layer in an organic electroluminescent device containing a compound having an inherently high quantum yield, and to further exhibit high luminance and highly efficient light emission. The object is to provide an electroluminescent device.

  As a result of intensive studies to solve the above-mentioned problems, the present inventor, in particular, an organic electroluminescent device in which a light emitting region is composed of a specific aminostyryl compound and a material capable of efficiently transmitting energy thereto. As a result, it has been found that a red light emitting element with high luminance and high reliability can be provided, and the present invention has been achieved.

  That is, the present invention relates to an organic electroluminescent device in which an organic layer having a light emitting region is provided between an anode and a cathode and includes an organic substance that emits light by current injection as a constituent element. A mixture layer containing at least one aminostyryl compound represented by the following general formula [I] (which may be one, but may be two or more). The present invention relates to an organic electroluminescent element (hereinafter sometimes referred to as a first organic EL element of the present invention).

［但し、前記一般式［Ｉ］において、Ｘ¹は下記一般式（１）〜（７）のいずれかで表される基であり

（但し、前記一般式（１）〜（３）において、Ｒ¹〜Ｒ⁴のうち少なくとも一つ（例えば一つ又は二つ）はハロゲン原子（フッ素原子、塩素原子、臭素原子等：以下、同様）、ニトロ基、シアノ基及びフルオロアルキル基（トリフルオロメチル基等：以下、同様）から選ばれた基であり、その他は水素原子、アルキル基、アリール基、アルコキシ基、ハロゲン原子、ニトロ基、シアノ基及びフルオロアルキル基から選ばれた基であり、それらが同一であっても異なっていてもよく、また前記一般式（４）〜（７）において、Ｒ⁵〜Ｒ¹⁰うち少なくとも一つ（例えば一つ又は二つ）はハロゲン原子、ニトロ基、シアノ基及びフルオロアルキル基から選ばれた基であり、その他は水素原子、アルキル基、アリール基、アルコキシ基、ハロゲン原子、ニトロ基、シアノ基及びフルオロアルキル基から選ばれた基であり、それらが同一であっても異なっていてもよい。）、
また、Ｙ¹は下記一般式（８）、又は（９）で表される基であり、Ｙ²は下記一般式（８）、（９）又は（１０）で表される基である。

（但し、前記一般式（８）〜（１０）において、Ｒ¹¹及びＲ¹²は水素原子、置換基を有してもよいアルキル基及び置換基を有してもよいアリール基から選ばれた基であり、それらが同一であっても異なっていてもよく、またＲ¹³〜Ｒ³⁵は水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいアルコキシ基、ハロゲン原子、ニトロ基、シアノ基及びフルオロアルキル基から選ばれた基であり、それらが同一であっても異なっていてもよい。）］

[However, in the said general formula [I], X < ¹ > is group represented by either of the following general formula (1)-(7).

(However, in the general formulas (1) to (3), at least one (for example, one or two) of R ^{1 to} R ⁴ is a halogen atom (fluorine atom, chlorine atom, bromine atom, etc.). ), A nitro group, a cyano group, and a fluoroalkyl group (trifluoromethyl group and the like: the same applies hereinafter), and the others are a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom, a nitro group, A group selected from a cyano group and a fluoroalkyl group, which may be the same or different, and in the general formulas (4) to (7), at least one of R ^{5 to} R ¹⁰ ( For example, one or two) is a group selected from a halogen atom, a nitro group, a cyano group and a fluoroalkyl group, and the others are a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom. A nitro group, a group selected from cyano group and a fluoroalkyl group, may be different even if they are identical.)
Y ¹ is a group represented by the following general formula (8) or (9), and Y ² is a group represented by the following general formula (8), (9) or (10).

(However, in the general formulas (8) to (10), R ¹¹ and R ¹² are groups selected from a hydrogen atom, an alkyl group which may have a substituent, and an aryl group which may have a substituent. And they may be the same or different, and R ^{13 to} R ³⁵ are each a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. A group selected from an alkoxy group, a halogen atom, a nitro group, a cyano group, and a fluoroalkyl group, which may have the same, or they may be the same or different.

また、Ｙ¹及びＹ²は下記一般式（８）又は（９）で表される基であってよい（以下、同様）。

（但し、前記一般式（８）及び（９）において、Ｒ¹¹及びＲ¹²は前記したものと同じであり、Ｒ¹³〜Ｒ³⁰は前記したものと同じであるが、フルオロアルキル基の場合はトリフルオロメチル基である。） In the general formula [I], X ¹ is a group represented by any one of the following structural formulas (11) to (14),

Y ¹ and Y ² may be a group represented by the following general formula (8) or (9) (hereinafter the same).

(However, in the general formulas (8) and (9), R ¹¹ and R ¹² are the same as those described above, and R ^{13 to} R ³⁰ are the same as those described above. A trifluoromethyl group.)

  According to the organic electroluminescent element of the present invention, in the organic electroluminescent element in which the organic layer having a light emitting region is provided between the anode and the cathode, the general formula [ I]], at least one of the aminostyryl compounds represented by the mixture is contained as a mixture or alone, so that the specific aminostyryl compound and / or a material capable of efficiently transferring energy to the light emitting region Thus, it is possible to provide a red light emitting device having high fluorescence yield, excellent thermal stability, good red purity, high luminance and high reliability.

  In addition, by providing the hole blocking layer, in the organic electroluminescence device containing the aminostyryl compound having a high quantum yield, the recombination of holes and electrons in the light emitting layer is promoted, and the brightness and the brightness are increased. An organic electroluminescent element that exhibits efficient light emission can be provided.

It is a principal part schematic sectional drawing of the organic electroluminescent element based on this invention. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other example of an organic electroluminescent element equally. It is a principal part schematic sectional drawing of the other another example of an organic electroluminescent element equally. It is a block diagram of a full-color flat display using an organic electroluminescent element.

  In the first organic EL element of the present invention, the organic layer has an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic stacked structure includes: The mixture layer may contain at least one aminostyryl compound represented by the general formula [I].

  Further, the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and at least the hole transport layer in the organic laminated structure is represented by the general formula [I]. The mixture layer may contain at least one aminostyryl compound.

  The organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer is at least one aminostyryl compound represented by the general formula [I]. And the electron transport layer may be composed of the mixture layer containing at least one aminostyryl compound represented by the general formula [I].

  Further, the organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is represented by the general formula [I]. The mixture layer may contain at least one aminostyryl compound represented.

In the present invention, materials that can be used to form the mixture layer containing the aminostyryl compound include, in addition to the aminostyryl compound, a hole transport material (for example, aromatic amines), an electron transport material (for example, , Alq ₃ , pyrazolines, etc.), or a series of compounds generally used as dopants for red light emission (DCM and its similar compounds, porphyrins, phthalocyanines, perylene compounds, Nile red, squarylium compounds, etc.) The same).

  In this case, at least one of the aminostyryl compounds in the mixture layer is contained in a proportion of 0.1 to 95% by weight when mixed with other compounds, and the content as a dopant within this range. Can be determined (the same applies hereinafter).

  Here, the “mixture layer” typically means a mixture layer of the aminostyryl compound and other compounds, but in addition to this, two or more kinds included in the aminostyryl compound are included. It may also mean a mixture layer of the above aminostyryl compounds. By setting it as such a mixture layer, red light emission of desired brightness | luminance and chromaticity can be produced by the combination of a some compound.

  The organic electroluminescent element of the present invention is suitable for use in, for example, a light emitting device configured as a display device (hereinafter the same).

In the organic electroluminescent device in which the organic layer having a light emitting region is provided between the anode and the cathode, at least one of the constituent layers of the organic layer has the following structural formula (15)- Aminostyryl represented by 1 to (15) -12, (16) -1 to (16) -12, (17) -1 to (17) -6, and (18) -1 to (18) -6 An organic electroluminescent device (hereinafter referred to as the second embodiment of the present invention) comprising a mixture layer containing at least one kind of compound (which may be one kind, but may be two kinds or more). It may be referred to as an organic EL element.).

  In the second organic EL device of the present invention, the organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic multilayer structure has the above-described structure. The mixture layer may contain at least one aminostyryl compound.

  The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the hole transport layer in the organic multilayer structure includes at least one kind of the aminostyryl compound. It may consist of the mixture layer.

  Further, the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer is composed of the mixture layer containing at least one kind of the aminostyryl compound, And the said electron carrying layer may consist of the said mixture layer containing at least 1 sort (s) of the said amino styryl compound.

  Further, the organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is at least one kind of the aminostyryl compound. It may consist of the said mixture layer containing.

  Further, the at least one of the constituent layers of the organic layer includes at least one kind of the aminostyryl compound and a red light emitting dye having a light emission maximum in a range of 600 nm or more, for example, 600 to 700 nm (hereinafter the same). It may consist of the said mixture layer containing.

  In this case, the organic layer has an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least one of the constituent layers of the organic layer is at least the electron transport layer. Good.

  Further, the organic layer may have an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least one of the constituent layers of the organic layer may be at least the hole transport layer. .

  The organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer has a light emission maximum in a range of 600 nm or more with at least one of the aminostyryl compounds. And the mixture layer containing at least one aminostyryl compound and a red light emitting dye having a light emission maximum in a range of 600 nm or more. May be layered.

  The organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is at least one of the aminostyryl compounds. The mixture layer may include a seed and a red light-emitting dye having a light emission maximum in a range of 600 nm or more.

  The present invention also provides an organic electroluminescent device in which an organic layer having a light emitting region is provided between an anode and a cathode, wherein at least one of the constituent layers of the organic layer is represented by the general formula [I]. A cathode of the light-emitting mixture layer, comprising a light-emitting mixture layer containing at least one aminostyryl compound represented (one type may be two or more). The present invention provides an organic electroluminescence device (hereinafter, sometimes referred to as a third organic EL device of the present invention) characterized in that a hole blocking layer is present on the side (particularly in contact).

  In the third organic EL device of the present invention, the organic layer has an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic stacked structure includes: The luminescent mixture layer may contain at least one aminostyryl compound represented by the general formula [I].

  Further, the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and at least the hole transport layer in the organic laminated structure is represented by the general formula [I]. The luminescent mixture layer may contain at least one aminostyryl compound.

  The organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer is at least one aminostyryl compound represented by the general formula [I]. And the electron transport layer is composed of the luminescent mixture layer containing at least one aminostyryl compound represented by the general formula [I], and the electron transport layer. The hole blocking layer may be present on the cathode side of the transporting light-emitting mixture layer.

  Further, the organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is represented by the general formula [I]. The light-emitting mixture layer may contain at least one aminostyryl compound represented.

  In the third organic EL device of the present invention, the hole blocking layer promotes recombination of holes and electrons in the light emitting layer, and can obtain light emission with high brightness and high efficiency. It is desirable that a material suitable for such a hole blocking layer has the following energy state (the same applies hereinafter). That is, the highest occupied molecular orbital level of the material forming the hole blocking layer is at an energy level lower than the highest occupied molecular orbital level of the material forming the layer in contact with the anode side of the hole blocking layer, and the hole blocking layer is The lowest unoccupied molecular orbital level of the material to be formed is at an energy level higher than the lowest unoccupied molecular orbital level of the material forming the layer that contacts the anode side of the hole blocking layer, and the layer that contacts the cathode side of the hole blocking layer is The energy level is lower than the lowest unoccupied molecular orbital level of the material to be formed.

  Examples of such materials include phenanthroline derivatives disclosed in JP-A-10-79297, JP-A-11-204258, JP-A-11-204264, JP-A-11-204259, and the like. The phenanthroline derivative is not limited as long as the energy level is satisfied. The phenanthroline derivatives that can be used are shown below.

（この一般式中、Ｒ¹〜Ｒ⁸は、水素原子、置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、置換もしくは非置換のアミノ基、ハロゲン原子、ニトロ基、シアノ基又は水酸基を表わす。）

(In this general formula, R ^{1 to} R ⁸ are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group. Represents.)

  According to the present invention, in the organic electroluminescent element in which the organic layer having a light emitting region is provided between the anode and the cathode, at least one of the constituent layers of the organic layer is the structural formula (15)- Aminostyryl represented by 1 to (15) -12, (16) -1 to (16) -12, (17) -1 to (17) -6, and (18) -1 to (18) -6 It consists of a luminescent mixture layer containing at least one kind of compound (which may be one kind, but may be two or more kinds), and hole blocking on the cathode side of the luminescent mixture layer The present invention provides an organic electroluminescent device (hereinafter, sometimes referred to as a fourth organic EL device of the present invention) characterized in that a layer is present.

  In the fourth organic EL element of the present invention, the organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic multilayer structure includes The luminescent mixture layer may contain at least one aminostyryl compound.

  The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the hole transport layer in the organic multilayer structure includes at least one kind of the aminostyryl compound. However, it may consist of the luminescent mixture layer.

  The organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the light-emitting mixture layer contains at least one of the aminostyryl compounds. The electron-transporting layer is composed of the light-emitting mixture layer containing at least one aminostyryl compound, and the hole-blocking layer is present on the cathode side of the electron-transporting light-emitting mixture layer You can do it.

  Further, the organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is at least one kind of the aminostyryl compound. It may consist of the said luminescent mixture layer containing.

In addition, the at least one of the constituent layers of the organic layer includes the luminescent mixture layer containing at least one aminostyryl compound and a red luminescent dye having a luminescence maximum in a range of 600 nm or more. It may be.

  In this case, the organic layer has an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least one of the constituent layers of the organic layer is at least the electron transport layer. Good.

  Further, the organic layer may have an organic stacked structure in which a hole transport layer and an electron transport layer are stacked, and at least one of the constituent layers of the organic layer may be at least the hole transport layer. .

  The organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer has a light emission maximum in a range of 600 nm or more with at least one of the aminostyryl compounds. And the electron transport layer includes at least one aminostyryl compound and a red light-emitting dye having a light emission maximum in a range of 600 nm or more. The hole blocking layer may be formed on the cathode side of the light-emitting mixture layer made of the light-emitting mixture layer.

  The organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is at least one of the aminostyryl compounds. The light-emitting mixture layer may include a seed and a red light-emitting dye having a light emission maximum in a range of 600 nm or more.

  The present invention also provides an organic electroluminescent device in which an organic layer having a light emitting region is provided between an anode and a cathode, wherein at least one of the constituent layers of the organic layer is represented by the general formula [I]. An organic electroluminescent device comprising an aminostyryl compound layer composed of a single aminostyryl compound represented by the present invention and having a hole blocking layer (particularly in contact) on the cathode side of the aminostyryl compound layer , Sometimes referred to as a fifth organic EL element of the present invention).

  In the fifth organic EL element of the present invention, the organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic multilayer structure is the It may consist of an aminostyryl compound layer.

  The organic layer may have an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, and at least the hole transport layer in the organic laminated structure may be composed of the aminostyryl compound layer. .

  Further, the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, the hole transport layer is composed of the aminostyryl compound layer, and the electron transport layer is the aminostyryl compound layer. The hole blocking layer may be present on the cathode side of the electron-transporting aminostyryl compound layer.

  The organic layer has an organic multilayer structure in which a hole transport layer, a light-emitting layer, and an electron transport layer are stacked, and at least the light-emitting layer of the organic multilayer structure includes the aminostyryl compound layer. It's okay.

  The hole blocking layer in the fifth organic EL element of the present invention may be configured in the same manner as the hole blocking layer in the third organic EL element of the present invention.

In the organic electroluminescence device in which an organic layer having a light emitting region is provided between an anode and a cathode, at least one of the constituent layers of the organic layer is the structural formula (15)- Aminostyryl represented by 1 to (15) -12, (16) -1 to (16) -12, (17) -1 to (17) -6, and (18) -1 to (18) -6 An organic electroluminescent element (hereinafter referred to as the sixth organic EL element of the present invention) comprising an aminostyryl compound layer composed of a compound alone and having a hole blocking layer on the cathode side of the aminostyryl compound layer Is also provided).

  In the sixth organic EL element of the present invention, the organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer in the organic multilayer structure is the amino layer. It may consist of a styryl compound layer.

  The organic layer may have an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the hole transport layer in the organic multilayer structure may be composed of the aminostyryl compound layer.

  Further, the organic layer has an organic laminated structure in which a hole transport layer and an electron transport layer are laminated, the hole transport layer is composed of the aminostyryl compound layer, and the electron transport layer is the aminostyryl compound. The hole blocking layer may be present on the cathode side of the electron-transporting aminostyryl compound layer.

  The organic layer has an organic laminated structure in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated, and at least the light emitting layer of the organic laminated structure is composed of the aminostyryl compound layer. Good.

  1 to 9 show examples of organic electroluminescent elements (organic EL elements) according to the present invention.

  FIG. 1 shows a transmissive organic electroluminescent device A in which the emitted light 20 is transmitted through the cathode 3, and the emitted light 20 can be observed from the protective layer 4 side. FIG. 2 shows a reflective organic electroluminescent device B that obtains reflected light at the cathode 3 as emitted light 20.

In the figure, reference numeral 1 denotes a substrate for forming an organic electroluminescent element. Glass, plastic and other suitable materials can be used. Moreover, when using an organic electroluminescent element in combination with another display element, a board | substrate can also be shared. 2 is a transparent electrode, and ITO (Indium tin oxide), SnO ₂ or the like can be used.

  Reference numeral 5 denotes an organic light emitting layer, which contains the above aminostyryl compound as a light emitting material (provided that at least one of the above aminostyryl compounds is mixed with other compounds or plural kinds of aminostyryl compounds). Containing compounds in combination: hereinafter the same). About this light emitting layer, conventionally well-known various structures can be used as a layer structure from which the organic electroluminescence 20 is obtained. As will be described later, for example, when a material constituting either the hole transport layer or the electron transport layer has a light emitting property, a structure in which these thin films are stacked can be used. Furthermore, in order to improve the charge transport performance within a range that satisfies the object of the present invention, either or both of the hole transport layer and the electron transport layer are structured by laminating thin films of plural kinds of materials, or plural kinds of materials. It does not prevent the use of a thin film having a composition mixed with Further, in order to improve the light emitting performance, at least one kind of fluorescent material is used, and the thin film is sandwiched between the hole transport layer and the electron transport layer, and at least one kind of fluorescent material. May be used in the hole transport layer, the electron transport layer, or both. In these cases, in order to improve luminous efficiency, a thin film for controlling the transport of holes or electrons can be included in the layer structure.

  Since the aminostyryl compound represented by the above general formula [I] has both electron transport performance and hole transport performance, it can be used as a mixed light-emitting layer with an electron transport material in the device structure or as a hole transport property. It can also be used as a mixed light emitting layer with a material. In addition, a mixed layer containing the compound can be used as a light-emitting material in a structure in which an electron-transport layer and a hole-transport layer are sandwiched.

  1 and 2, reference numeral 3 denotes a cathode. As an electrode material, an alloy of an active metal such as Li, Mg, or Ca and a metal such as Ag, Al, or In or a laminated structure can be used. In the transmissive organic electroluminescent device, the light transmittance suitable for the application can be obtained by adjusting the thickness of the cathode. Further, in the figure, reference numeral 4 denotes a sealing / protecting layer, and the effect is enhanced by adopting a structure that covers the entire organic electroluminescent element. An appropriate material can be used as long as the airtightness is maintained.

  In the organic electroluminescent device according to the present invention, the organic layer has an organic laminated structure (single heterostructure) in which a hole transport layer and an electron transport layer are laminated, and the hole transport layer or the electron transport. A mixture layer containing the aminostyryl compound may be used as a layer forming material. Alternatively, the organic layer has an organic laminated structure (double heterostructure) in which a hole transport layer, a light emitting layer, and an electron transport layer are sequentially laminated, and a mixture layer containing the styryl compound as a light emitting layer forming material is May be used.

  As an example of an organic electroluminescent device having such an organic laminated structure, FIG. 3 shows that a translucent anode 2, a hole transport layer 6 and an electron transport layer 7 are formed on a translucent substrate 1. This is an organic electroluminescent device C having a single hetero structure, which has a laminated structure in which an organic layer 5 a made of the above and a cathode 3 are sequentially laminated, and this laminated structure is sealed by a protective layer 4.

  In the case of a layer configuration in which the light emitting layer is omitted as shown in FIG. 3, light emission 20 having a predetermined wavelength is generated from the interface between the hole transport layer 6 and the electron transport layer 7. These luminescences are observed from the substrate 1 side.

  FIG. 4 shows a light-transmitting substrate 1, a light-transmitting anode 2, an organic layer 5b composed of a hole-transporting layer 10, a light-emitting layer 11, and an electron-transporting layer 12, and a cathode 3 sequentially. This is an organic electroluminescent element D having a double hetero structure, which has a laminated structure in which the laminated structure is sealed by a protective layer 4.

  In the organic electroluminescence device shown in FIG. 4, by applying a DC voltage between the anode 2 and the cathode 3, holes injected from the anode 2 are injected through the hole transport layer 10 and from the cathode 3. The emitted electrons reach the light emitting layer 11 through the electron transport layer 12. As a result, electron / hole recombination occurs in the light emitting layer 11 to generate singlet excitons, and light emission of a predetermined wavelength is generated from the singlet excitons.

  In each of the organic electroluminescent elements C and D described above, the substrate 1 can be appropriately made of a light transmissive material such as glass or plastic. Further, this substrate may be shared when used in combination with other display elements or when the stacked structure shown in FIGS. 3 and 4 is arranged in a matrix. In addition, the elements C and D can both adopt a transmission type and a reflection type structure.

The anode 2 is a transparent electrode, and ITO, SnO ₂ or the like can be used. A thin film made of an organic material or an organometallic compound may be provided between the anode 2 and the hole transport layer 6 (or the hole transport layer 10) for the purpose of improving the charge injection efficiency. In addition, when the protective layer 4 is formed of a conductive material such as metal, an insulating film may be provided on the side surface of the anode 2.

  Moreover, the organic layer 5a in the organic electroluminescent element C is an organic layer in which the hole transport layer 6 and the electron transport layer 7 are laminated, and a mixture containing the aminostyryl compound described above is contained in either or both of them. Thus, the light-emitting hole transport layer 6 or the electron transport layer 7 may be used. The organic layer 5b in the organic electroluminescent device D is an organic layer in which a hole transport layer 10, a light emitting layer 11 made of a mixture containing the aminostyryl compound described above, and an electron transport layer 12 are laminated. A laminated structure can be adopted. For example, either or both of the hole transport layer and the electron transport layer may emit light.

  In the hole transport layer, a hole transport layer in which a plurality of types of hole transport materials are stacked may be formed in order to improve hole transport performance.

  In the organic electroluminescent device C, the light emitting layer may be the electron transporting light emitting layer 7, but depending on the voltage applied from the power supply 8, light may be emitted from the hole transporting layer 6 or its interface. Similarly, in the organic electroluminescent element D, the light emitting layer may be the electron transport layer 12 or the hole transport layer 10 in addition to the layer 11. In order to improve the light emitting performance, it is preferable that the light emitting layer 11 using at least one fluorescent material is sandwiched between the hole transport layer and the electron transport layer. Or you may comprise the structure which contained this fluorescent material in the positive hole transport layer or the electron carrying layer, or these both layers. In such a case, in order to improve luminous efficiency, a thin film (such as a hole blocking layer or an exciton generation layer) for controlling the transport of holes or electrons can be included in the layer configuration.

  The material used for the cathode 3 may be an alloy of an active metal such as Li, Mg, or Ca and a metal such as Ag, Al, or In, and may have a structure in which these metal layers are laminated. It should be noted that an organic electroluminescent element suitable for the application can be produced by appropriately selecting the thickness and material of the cathode.

  Moreover, the protective layer 4 acts as a sealing film, and can improve the charge injection efficiency and the light emission efficiency by covering the entire organic electroluminescence device. In addition, as long as the airtightness is maintained, a material such as a single metal such as aluminum, gold, or chromium, or an alloy thereof can be appropriately selected.

  The current applied to each of the organic electroluminescent elements is usually a direct current, but a pulse current or an alternating current may be used. The current value and the voltage value are not particularly limited as long as they are within the range that does not destroy the element. However, considering the power consumption and life of the organic electroluminescence element, it is desirable to efficiently emit light with as little electrical energy as possible.

  5 to 9, in the organic EL elements A to D shown in FIGS. 1 to 4, holes are in contact with the light emitting layer 5, the hole transport layer 6, the electron transport layer 7, or the light emitting layer 11 on the cathode 3 side. Examples A ′ to D ′ in which the blocking layer 30 is provided are shown. Here, as described above, the aminostyryl compound may be used in combination with a plurality of aminostyryl compounds in addition to at least one kind being mixed with other compounds. Alternatively, a single aminostyryl compound alone may form a layer.

  Next, FIG. 10 is a configuration example of a flat display using the organic electroluminescent element of the present invention. As shown in the figure, in the case of a full color display, for example, organic layers 5 (5a, 5b) capable of emitting three primary colors of red (R), green (G) and blue (B) are disposed between the cathode 3 and the anode 2. It is arranged in. The cathode 3 and the anode 2 can be provided in stripes crossing each other, and are selected by the luminance signal circuit 14 and the control circuit 15 with a built-in shift register, and a signal voltage is applied to each of them, whereby the selected cathode 3 and the organic layer at the position (pixel) where the anode 2 intersects are configured to emit light.

  That is, FIG. 10 is an 8 × 3 RGB simple matrix, for example, in which a laminate 5 composed of a hole transport layer and at least one of a light emitting layer and an electron transport layer is disposed between the cathode 3 and the anode 2. (See FIG. 3 or FIG. 4). The cathode and the anode are both patterned in stripes, orthogonal to each other in a matrix, and a signal voltage is applied in time series by the control circuit 15 and the luminance signal circuit 14 with a built-in shift register so that light is emitted at the crossing position. It is composed of. The EL element having such a structure can be used not only as a display of characters and symbols but also as an image reproducing device. In addition, a striped pattern of the cathode 3 and the anode 2 can be arranged for each color of red (R), green (G), and blue (B) to constitute a multi-color or full-color all-solid-type flat panel display. It becomes.

  Next, although the Example of this invention is shown, this invention is not limited to this.

[Example 1]
In this example, among the aminostyryl compounds of the above general formula [I], a hole is transported through a mixture layer of an aminostyryl compound of the following structural formula (15) -3 and α-NPD (α-naphthylphenyldiamine). This is an example in which an organic electroluminescent element having a single hetero structure was used as a conductive light emitting layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a vapor deposition mask is disposed close to the substrate, and the above-mentioned structural formula (15) -3 is applied under vacuum of 10 ⁻⁴ Pa or less by a vacuum vapor deposition method. A layer in which an aminostyryl compound and α-NPD that is a hole transporting material were mixed at a weight ratio of 1: 1 was formed as a hole transporting layer (also serving as a light emitting layer) with a thickness of, for example, 50 nm. The deposition rate was 0.1 nm / second.

Further, Alq ₃ (tris (8-quinolinol) aluminum) having the following structural formula was deposited as an electron transport layer material in contact with the hole transport layer. The film thickness of this electron transport layer made of Alq ₃ was also set to 50 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg film) and 150 nm (Ag film). An organic electroluminescent device as shown in FIG.

The organic electroluminescence device of Example 1 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and as a result of spectroscopic measurement, a spectrum having an emission peak near 630 nm was obtained. For the spectroscopic measurement, a spectroscope using a photodiode array manufactured by Otsuka Electronics Co., Ltd. as a detector was used. Further, when the voltage-luminance measurement was performed, a luminance of 2000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 900 hours until the luminance was reduced to half.

[Example 2]
This example uses a mixture layer of the aminostyryl compound represented by the structural formula (15) -3 and the Alq ₃ among the aminostyryl compounds represented by the general formula [I] described above as a single heterostructure. This is an example of fabricating an organic electroluminescent element.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD of the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 50 nm. The deposition rate was 0.1 nm / second.

Furthermore, a layer in which the aminostyryl compound of the structural formula (15) -3 and Alq ₃ which is an electron transporting material were mixed at a weight ratio of 1: 1 was deposited in contact with the hole transporting layer. The film thickness of the electron transport layer (also serving as the light emitting layer) composed of the aminostyryl compound of the structural formula (15) -3 and Alq ₃ was also set to 50 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film), and an organic material as shown in FIG. An electroluminescent element was produced.

The organic electroluminescence device of Example 2 produced in this way was subjected to forward bias DC voltage in a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1200 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 800 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 3]
This example uses a mixture layer of the aminostyryl compound represented by the structural formula (15) -3 and Alq ₃ among the aminostyryl compounds represented by the general formula [I] described above as an electron-transporting light-emitting layer. This is an example of fabricating an organic electroluminescent element.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD having the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.2 nm / second.

Further, the aminostyryl compound of the structural formula (15) -3 and Alq ₃ were deposited as a light emitting material in contact with the hole transport layer at a weight ratio of 1: 1. The film thickness of the light emitting layer composed of a mixture layer of the aminostyryl compound of the structural formula (15) -3 and Alq ₃ was also set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

Further, Alq ₃ having the above structural formula was deposited as an electron transporting material in contact with the light emitting layer. The film thickness of Alq ₃ was set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film). Organic electroluminescent devices as shown were fabricated.

The organic electroluminescence device of Example 3 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak at 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 2500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the current value was constantly supplied at an initial luminance of 200 cd / m ² and the light was continuously emitted to forcibly deteriorate it, it took 1500 hours until the luminance was reduced to half.

[Example 4]
In this example, among the aminostyryl compounds of the above general formula [I], the mixture layer of the aminostyryl compound represented by the structural formula (15) -3 and the aminostyryl compound represented by the following structural formula (15) -1 was emitted. This is an example in which an organic electroluminescent device having a double hetero structure was used as a layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD having the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.2 nm / second.

  Further, the aminostyryl compound represented by the structural formula (15) -3 and the aminostyryl compound represented by the structural formula (15) -1 were co-deposited in contact with the hole transport layer at a weight ratio of 1: 3 as a light emitting material. The film thickness of the light emitting layer composed of a mixture layer of the aminostyryl compound of the structural formula (15) -3 and the aminostyryl compound of the structural formula (15) -1 is also set to 30 nm, for example, and the deposition rate is the structural formula (15). The compound of −3 was 0.1 nm / second, and the compound of the structural formula (15) -1 was 0.3 nm / second.

Further, Alq ₃ having the above structural formula was deposited as an electron transporting material in contact with the light emitting layer. The film thickness of Alq ₃ was set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film). Organic electroluminescent devices as shown were fabricated.

The organic electroluminescence device of Example 4 produced in this way was subjected to forward bias DC voltage in a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak at 640 nm was obtained. When the voltage-luminance measurement was performed, a luminance of 3000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it was 1200 hours until the luminance was reduced to half.

[Example 5]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of the aminostyryl compound of the structural formula (15) -3 and DCM of the following structural formula was used as an electron transporting light emitting layer. It is the example which produced the organic electroluminescent element of a single heterostructure.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD having the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 50 nm. The deposition rate was 0.1 nm / second.

  Further, a layer in which the aminostyryl compound of the structural formula (15) -3 and the DCM were mixed at a weight ratio of 10: 1 was deposited in contact with the hole transport layer. The film thickness of the electron transport layer (also known as the light emitting layer) composed of the aminostyryl compound of the structural formula (15) -3 and the DCM is also 50 nm, for example, and the deposition rate is 0.5 nm for the compound of the structural formula (15) -3. / Sec, DCM was 0.05 nm / sec.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film), and an organic material as shown in FIG. An electroluminescent element was produced.

The organic electroluminescence device of Example 5 produced in this way was subjected to forward bias DC voltage under a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it took 500 hours until the luminance was reduced to half.

[Example 6]
This example uses a mixture layer of an aminostyryl compound represented by the following structural formula (15) -2 and Alq ₃ as the electron transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I], and has a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 6 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 590 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 850 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 7]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (15) -4 and Alq ₃ was used as an electron-transporting light-emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 7 produced in this way was subjected to forward bias DC voltage under a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 610 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, it was 450 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 8]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (15) -6 and Alq ₃ was used as an electron transporting light emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 8 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 585 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to emit light continuously and forcedly deteriorated, it was 200 hours until the luminance was reduced to half.

[Example 9]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (15) -7 and Alq ₃ was used as an electron transporting light emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 9 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 615 nm was obtained. When the voltage-luminance measurement was performed, a luminance of 580 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 300 hours until the luminance was reduced to half.

[Example 10]
This example uses a mixture layer of the aminostyryl compound of the following structural formula (15) -8 and Alq ₃ among the aminostyryl compounds of the general formula [I] described above as a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 10 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 610 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 430 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to emit light continuously and forcibly deteriorated, it took 150 hours until the luminance was reduced to half.

[Example 11]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (15) -9 and Alq ₃ was used as an electron transporting light emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 11 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 640 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, it was 450 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 12]
This example uses a mixture layer of an aminostyryl compound of the following structural formula (15) -11 and Alq ₃ among the aminostyryl compounds of the general formula [I] described above as a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 12 produced in this way was subjected to forward bias DC voltage in a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 580 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 750 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value with an initial luminance of 200 cd / m ² .

[Example 13]
This example uses a mixture layer of an aminostyryl compound represented by the following structural formula (15) -12 and Alq ₃ as the electron transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I], and has a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 13 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 600 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 850 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 14]
This example uses a mixture layer of an aminostyryl compound represented by the following structural formula (17) -1 and Alq ₃ as an electron transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I], and has a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 14 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 620 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 1500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 800 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 15]
This example uses a mixture layer of the aminostyryl compound represented by the following structural formula (17) -2 and Alq ₃ among the aminostyryl compounds represented by the general formula [I] described above as a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 15 produced as described above was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 645 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1200 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 700 hours until the luminance was reduced to half.

[Example 16]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (17) -3 and Alq ₃ was used as an electron-transporting light-emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 16 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 590 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 780 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it took 500 hours until the luminance was reduced to half.

[Example 17]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (17) -4 and Alq ₃ was used as an electron-transporting light-emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 17 produced in this manner was subjected to forward bias DC voltage in a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 620 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1100 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 18]
This example uses a mixture layer of the aminostyryl compound represented by the following structural formula (17) -5 and Alq ₃ as the electron transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] described above, and has a single heterostructure. This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 18 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 650 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 700 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 400 hours until the luminance was reduced to half.

[Example 19]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of an aminostyryl compound of the following structural formula (15) -5 and Alq ₃ was used as an electron transporting light emitting layer, and a single heterostructure This is an example of fabricating an organic electroluminescent element.

  An organic electroluminescent device was produced in accordance with Example 2 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 19 produced in this manner was evaluated for light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 1. As a result, a spectrum having an emission peak near 655 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 1500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 700 hours until the luminance was reduced to half.

[Example 20]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of the aminostyryl compound of the above structural formula (15) -3 and α-NPD was used as a hole transporting light emitting layer. This is an example in which an organic electroluminescent device having a single heterostructure was produced using a mixture layer of the aminostyryl compound represented by the structural formula (15) -3 and Alq ₃ as an electron-transporting light-emitting layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a vapor deposition mask is disposed close to the substrate, and the above-mentioned structural formula (15) -3 is applied under vacuum of 10 ⁻⁴ Pa or less by a vacuum vapor deposition method. A layer in which an aminostyryl compound and α-NPD which is a hole transporting material were mixed at a weight ratio of 1: 1 was formed as a hole transporting layer (also serving as a light emitting layer) with a thickness of, for example, 50 nm. The deposition rate was 0.1 nm / second.

Further, a layer in which the compound of the structural formula (15) -3 and Alq ₃ which is an electron transporting material were mixed at a weight ratio of 1: 1 was deposited in contact with the hole transporting layer (also serving as the light emitting layer). The film thickness of the electron transport layer (also serving as the light emitting layer) composed of the compound of the structural formula (15) -3 and Alq ₃ was also set to 50 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, which is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg film) and 150 nm (Ag film). An organic electroluminescent device as shown in FIG.

The organic electroluminescence device of Example 20 produced in this way was subjected to forward bias DC voltage under a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and as a result of spectroscopic measurement, a spectrum having an emission peak near 635 nm was obtained. For the spectroscopic measurement, a spectroscope using a photodiode array manufactured by Otsuka Electronics Co., Ltd. as a detector was used. Further, when the voltage-luminance measurement was performed, a luminance of 1800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcedly deteriorated, it was 1000 hours until the luminance was reduced to half.

[Example 21]
In this example, among the aminostyryl compounds of the above general formula [I], the hole transport is performed on the mixture layer of the aminostyryl compound of the structural formula (15) -3 and α-NPD (α-naphthylphenyldiamine). It is the example which produced the organic electroluminescent element used as a characteristic light emitting layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a vapor deposition mask is disposed close to the substrate, and the above-mentioned structural formula (15) -3 is applied under vacuum of 10 ⁻⁴ Pa or less by a vacuum vapor deposition method. A layer in which an aminostyryl compound and α-NPD that is a hole transporting material were mixed at a weight ratio of 1: 1 was formed as a hole transporting layer (also serving as a light emitting layer) with a thickness of, for example, 50 nm. The deposition rate was 0.1 nm / second.

  Furthermore, bathocuproine having the following structural formula was deposited as a hole blocking layer material in contact with the hole transport layer (also the light emitting layer). The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ (tris (8-quinolinol) aluminum) having the above structural formula was deposited as an electron transport layer material in contact with the hole blocking layer. The film thickness of this electron transport layer made of Alq ₃ was also set to 50 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg film) and 150 nm (Ag film). An organic electroluminescent device as shown in FIG.

The organic electroluminescence device of Example 21 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and as a result of spectroscopic measurement, a spectrum having an emission peak near 630 nm was obtained. For the spectroscopic measurement, a spectroscope using a photodiode array manufactured by Otsuka Electronics Co., Ltd. as a detector was used. Further, when voltage-luminance measurement was performed, a luminance of 2500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcedly deteriorated, it was 1000 hours until the luminance was reduced to half.

[Example 22]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -3 and Alq ₃ as an electron-transporting light-emitting layer. This is an example in which an element was manufactured.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a deposition mask is disposed close to the substrate, and α-NPD having the following structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.1 nm / second.

Furthermore, a layer in which the compound of the structural formula (15) -3 and Alq ₃ which is an electron transporting material were mixed at a weight ratio of 1: 1 was co-deposited in contact with the hole transport layer. The film thickness of the electron transport layer (also serving as the light emitting layer) composed of the compound of the structural formula (15) -3 and Alq ₃ was also set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the hole transport layer (also serving as the light emitting layer) as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ having the above structural formula was deposited in contact with the hole blocking layer as an electron transport layer material. The film thickness of this electron transport layer made of Alq ₃ was, for example, 30 nm, and the deposition rate was 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second to a thickness of, for example, 50 nm (Mg) and 150 nm (Ag film), as shown in FIG. An electroluminescent element was produced.

The organic electroluminescence device of Example 22 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 630 nm was obtained. When voltage-luminance measurement was performed, a luminance of 3400 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² , the current value was constantly supplied to continuously emit light, and forced degradation, it was 1200 hours until the luminance was reduced to half.

[Example 23]
In this example, among the aminostyryl compounds of the above general formula [I], the mixture layer of the aminostyryl compound of the above structural formula (15) -3 and the aminostyryl compound of the above structural formula (15) -1 was emitted. It is the example which produced the organic electroluminescent element used as a layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD having the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.2 nm / second.

  Further, the compound of the structural formula (15) -3 and the compound of the structural formula (15) -1 were co-deposited in contact with the hole transport layer at a weight ratio of 1: 3 as a light emitting material. The film thickness of the light emitting layer composed of the mixture layer of the compound of the structural formula (15) -3 and the compound of the structural formula (15) -1 is also set to 30 nm, for example, and the deposition rate is the compound of the structural formula (15) -3. Was 0.1 nm / second, and the compound of the structural formula (15) -1 was 0.3 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the light emitting layer as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ having the above structural formula was deposited in contact with the hole blocking layer as an electron transporting material. The film thickness of Alq ₃ was set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film). Organic electroluminescent devices as shown were fabricated.

The organic electroluminescence device of Example 23 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak at 640 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 4000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it was 1600 hours until the luminance was reduced to half.

[Example 24]
In this example, among the aminostyryl compounds of the above general formula [I], a mixture layer of the aminostyryl compound of the above structural formula (15) -3 and the DCM of the above structural formula was used as the electron transporting light emitting layer. It is the example which produced the organic electroluminescent element.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. As a deposition mask, a plurality of metal masks having 2.0 mm × 2.0 mm unit openings are arranged close to the substrate, and α-NPD having the above structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.1 nm / second.

  Further, a layer in which the compound of the structural formula (15) -3 and the DCM were mixed at a weight ratio of 10: 1 was co-deposited in contact with the hole transport layer. The film thickness of the electron transport layer (also serving as the light emitting layer) composed of the compound of the structural formula (15) -3 and the DCM is also set to 30 nm, for example, and the deposition rate is 0.5 nm / day for the compound of the structural formula (15) -3. Second, DCM was 0.05 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the light emitting layer as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ having the above structural formula was deposited in contact with the hole blocking layer as an electron transporting material. The film thickness of Alq ₃ was set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg) and 150 nm (Ag film), as shown in FIG. An electroluminescent element was produced.

The organic electroluminescence device of Example 24 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 25]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (15) -2 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 25 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 590 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1100 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 700 hours until the luminance was reduced to half.

[Example 26]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (15) -4 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 26 produced as described above was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 610 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 550 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 27]
In this example, among the above-mentioned aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -6 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 27 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 585 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 600 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 300 hours until the luminance was reduced to half.

[Example 28]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -7 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 28 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 615 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 650 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 350 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 29]
In this example, among the above-mentioned aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -8 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 29 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 610 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 500 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to emit light continuously and forcedly deteriorated, it was 200 hours until the luminance was reduced to half.

[Example 30]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (15) -9 and Alq ₃ as an electron-transporting light-emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 30 produced in this way was subjected to forward bias DC voltage in a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 640 nm was obtained. The voltage - was subjected to luminance measurement, the luminance of 920 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 480 hours until the luminance was reduced to half.

[Example 31]
In this example, an organic electroluminescent element using a mixture layer of the compound represented by the structural formula (15) -11 and Alq ₃ as the electron-transporting light-emitting layer among the above-described aminostyryl compounds represented by the general formula [I]. This is a manufactured example.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 31 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 580 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1100 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 800 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 32]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -12 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 32 produced in this way was subjected to forward bias DC voltage under a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 600 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 900 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 660 hours until the luminance was reduced to half.

[Example 33]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (17) -1 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 33 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 620 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 1650 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to emit light continuously and forcibly deteriorated, it took 880 hours until the luminance was reduced to half.

[Example 34]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (17) -2 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 34 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 645 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1300 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 800 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 35]
In this example, among the above-described aminostyryl compounds represented by the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound represented by the structural formula (17) -3 and Alq ₃ as an electron-transporting light-emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 35 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 600 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1450 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 700 hours until the luminance was reduced to half.

[Example 36]
In this example, among the above-mentioned aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the structural formula (17) -4 and Alq ₃ as an electron-transporting light-emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 36 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 620 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1200 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, by applying a constant current thereto with an initial luminance 200 cd / m ² continuous emission, when the forced degradation was 650 hours until the luminance is halved.

[Example 37]
In this example, among the above-mentioned aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (17) -5 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 37 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 650 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it took 500 hours until the luminance was reduced to half.

[Example 38]
In this example, among the above-described aminostyryl compounds of the general formula [I], organic electroluminescence using a mixture layer of the aminostyryl compound of the above structural formula (15) -5 and Alq ₃ as an electron transporting light emitting layer. This is an example in which an element was manufactured.

  An organic electroluminescent element was produced in accordance with Example 22 for both the layer structure and the film formation method.

The organic electroluminescence device of Example 38 produced as described above was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 21. As a result, a spectrum having an emission peak near 655 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 1720 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 780 hours until the luminance was reduced to half when it was subjected to continuous light emission with a constant current value at an initial luminance of 200 cd / m ² and forced emission.

[Example 39]
In this example, among the aminostyryl compounds represented by the general formula [I], a mixture layer of the aminostyryl compound represented by the structural formula (15) -3 and α-NPD was used as a hole transporting light emitting layer. This is an example in which an organic electroluminescent element was produced using a mixture layer of the aminostyryl compound of the structural formula (15) -3 and Alq ₃ as an electron transporting light emitting layer.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a vapor deposition mask is disposed close to the substrate, and the above-mentioned structural formula (15) -3 is applied under vacuum of 10 ⁻⁴ Pa or less by a vacuum vapor deposition method. A layer in which the compound and α-NPD as a hole transporting material were mixed at a weight ratio of 1: 1 was formed as a hole transporting layer (also serving as a light emitting layer) with a thickness of, for example, 30 nm. The deposition rate was 0.1 nm / second.

Furthermore, a layer in which the compound of the structural formula (15) -3 and Alq ₃ which is an electron transporting material were mixed at a weight ratio of 1: 1 was co-deposited in contact with the hole transporting layer (also serving as the light emitting layer). The film thickness of the electron transport layer (also known as light emitting layer) composed of the compound of the structural formula (15) -3 and Alq ₃ was also set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the electron transport layer (also serving as the light emitting layer) as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ having the above structural formula was deposited in contact with the hole blocking layer as an electron transporting material. The film thickness of Alq ₃ was set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, which is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg film) and 150 nm (Ag film). An organic electroluminescent device as shown in FIG.

The organic electroluminescence device of Example 39 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and as a result of spectroscopic measurement, a spectrum having an emission peak near 635 nm was obtained. For the spectroscopic measurement, a spectroscope using a photodiode array manufactured by Otsuka Electronics Co., Ltd. as a detector was used. Further, when the voltage-luminance measurement was performed, a luminance of 2900 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 1100 hours until the luminance was reduced to half.

[Example 40]
This example is an example in which an organic electroluminescent device using the aminostyryl compound represented by the structural formula (15) -3 among the aminostyryl compounds represented by the general formula [I] as a hole transporting light emitting layer was prepared. is there.

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a vapor deposition mask is disposed close to the substrate, and the above-mentioned structural formula (15) -3 is applied under vacuum of 10 ⁻⁴ Pa or less by a vacuum vapor deposition method. The aminostyryl compound was formed into a film having a thickness of, for example, 50 nm as a hole transport layer (also serving as a light emitting layer). The deposition rate was 0.1 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the hole transport layer as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ (tris (8-quinolinol) aluminum) having the above structural formula was deposited as an electron transport layer material in contact with the hole blocking layer. The film thickness of this electron transport layer made of Alq ₃ was also set to 50 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second, for example, to a thickness of 50 nm (Mg film) and 150 nm (Ag film). An organic electroluminescent device as shown in FIG.

The organic electroluminescence device of Example 40 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and as a result of spectroscopic measurement, a spectrum having an emission peak near 640 nm was obtained. For the spectroscopic measurement, a spectroscope using a photodiode array manufactured by Otsuka Electronics Co., Ltd. as a detector was used. Further, when voltage-luminance measurement was performed, a luminance of 3000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 1100 hours until the luminance was reduced to half.

[Example 41]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -3 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

First, a 30 mm × 30 mm glass substrate having an anode made of ITO having a thickness of 100 nm formed on one surface was set in a vacuum deposition apparatus. A metal mask having a plurality of 2.0 mm × 2.0 mm unit openings as a deposition mask is disposed close to the substrate, and α-NPD having the following structural formula is obtained, for example, under a vacuum of 10 ⁻⁴ Pa or less by a vacuum deposition method. The film was formed to a thickness of 30 nm. The deposition rate was 0.1 nm / second.

  Further, the compound of the structural formula (15) -3 was deposited in contact with the hole transport layer. The film thickness of the electron transport layer (also serving as the light emitting layer) made of the compound of the structural formula (15) -3 was also set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  Further, bathocuproine having the above structural formula was deposited in contact with the light emitting layer as a hole blocking layer material. The hole blocking layer made of bathocuproine has a thickness of 15 nm, for example, and a deposition rate of 0.1 nm / second.

Further, Alq ₃ having the above structural formula was deposited in contact with the hole blocking layer as an electron transport layer material. The thickness of this electron transport layer made of Alq ₃ was also set to 30 nm, for example, and the deposition rate was set to 0.2 nm / second.

  As the cathode material, a laminated film of Mg and Ag is adopted, and this is also formed by vapor deposition at a deposition rate of 1 nm / second to a thickness of, for example, 50 nm (Mg) and 150 nm (Ag film), as shown in FIG. An electroluminescent element was produced.

The organic electroluminescence device of Example 41 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 640 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 3800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it took 1500 hours until the luminance was reduced to half.

[Example 42]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -2 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 42 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 600 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1200 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 800 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 43]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -4 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 43 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak in the vicinity of 620 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1100 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 44]
This example is an example in which an organic electroluminescent device using the compound represented by the structural formula (15) -6 among the aminostyryl compounds represented by the general formula [I] as an electron transporting light emitting layer was prepared.

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 44 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 595 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 700 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 300 hours until the luminance was reduced to half.

[Example 45]
This example is an example in which an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -7 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 45 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak in the vicinity of 620 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 750 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, it was 450 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value at an initial luminance of 200 cd / m ² and forced degradation.

[Example 46]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -8 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 46 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak in the vicinity of 620 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 520 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it took 250 hours until the luminance was reduced to half.

[Example 47]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -9 among the aminostyryl compounds represented by the general formula [I] described above as an electron-transporting light-emitting layer was produced. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 47 produced in this manner was subjected to forward bias DC voltage application under a nitrogen atmosphere to evaluate the light emission characteristics. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 650 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1000 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized to continuously emit light and forced degradation, it was 600 hours until the luminance was reduced to half.

[Example 48]
This example is an example in which an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -11 among the aminostyryl compounds represented by the general formula [I] as an electron-transporting light-emitting layer was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 48 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was orange, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 590 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1200 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it took 850 hours until the luminance was reduced to half.

[Example 49]
In this example, an organic electroluminescent element using the aminostyryl compound represented by the structural formula (15) -12 among the aminostyryl compounds represented by the general formula [I] as an electron-transporting light-emitting layer was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 49 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 610 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 930 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it was 700 hours until the luminance was reduced to half.

[Example 50]
This example is an example in which an organic electroluminescent element using the aminostyryl compound represented by the structural formula (17) -1 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 50 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1700 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcedly deteriorated, it was 1000 hours until the luminance was reduced to half.

[Example 51]
This example is an example in which an organic electroluminescent element using the compound represented by the structural formula (17) -2 as the electron transporting light emitting layer among the aminostyryl compounds represented by the general formula [I] was manufactured.

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 51 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 655 nm was obtained. Further, when the voltage-luminance measurement was performed, a luminance of 1400 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was constantly supplied to continuously emit light and forcibly deteriorated, it took 850 hours until the luminance was reduced to half.

[Example 52]
This example is an example in which an organic electroluminescent element using the compound of the above structural formula (17) -3 as the electron transporting light emitting layer among the aminostyryl compounds of the above general formula [I] was produced.

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 52 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak in the vicinity of 600 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 900 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² , the current value was constantly supplied to continuously emit light and forced degradation, it was 650 hours until the luminance was reduced to half.

[Example 53]
This example is an example in which an organic electroluminescent element using the compound represented by the structural formula (17) -4 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was manufactured.

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 53 produced in this manner was subjected to evaluation of light emission characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 630 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1300 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. Further, it was 750 hours until the luminance was reduced to half when the device was subjected to continuous light emission by applying a constant current value with an initial luminance of 200 cd / m ² .

[Example 54]
This example is an example in which an organic electroluminescent device using the compound of the above structural formula (17) -5 as the electron transporting light emitting layer among the aminostyryl compounds of the general formula [I] was prepared.

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 54 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 660 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 800 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the current value was constantly supplied at an initial luminance of 200 cd / m ² to continuously emit light and forcibly deteriorated, it took 500 hours until the luminance was reduced to half.

[Example 55]
This example is an example in which an organic electroluminescent device using the aminostyryl compound represented by the structural formula (15) -5 as the electron-transporting light-emitting layer among the aminostyryl compounds represented by the general formula [I] was prepared. .

  An organic electroluminescent element was produced according to Example 41 in both the layer structure and the film formation method.

The organic electroluminescence device of Example 55 produced in this manner was subjected to evaluation of luminescence characteristics by applying a forward bias DC voltage in a nitrogen atmosphere. The emission color was red, and spectroscopic measurement was performed in the same manner as in Example 40. As a result, a spectrum having an emission peak near 660 nm was obtained. Further, when voltage-luminance measurement was performed, a luminance of 1700 cd / m ² was obtained at 8V.

After this organic electroluminescent device was fabricated, it was left in a nitrogen atmosphere for 1 month, but no device degradation was observed. In addition, when the initial luminance was 200 cd / m ² and the current value was energized continuously to continuously emit light and forcibly deteriorated, it was 900 hours until the luminance was reduced to half.

  The present invention is suitable for an organic electroluminescent element (organic EL element) in which an organic layer having a light emitting region is provided between an anode and a cathode, and a light emitting device such as a display device using the same.

DESCRIPTION OF SYMBOLS 1 ... Board | substrate, 2 ... Transparent electrode (anode), 3 ... Cathode, 4 ... Protective film 5, 5a, 5b ... Organic layer,
6 ... hole transport layer, 7 ... electron transport layer, 8 ... power source, 10 ... hole transport layer, 11 ... light emitting layer,
12 ... Electron transport layer, 14 ... Luminance signal circuit, 15 ... Control circuit, 20 ... Light emission,
30 ... hole blocking layer, A, B, C, D, A ', B', C ', D' ... organic electroluminescence device

JP 7-188649 A (Japanese Patent Application No. 6-148798)

Chem. Funct. Dyes, Proc. Int. Symp., 2nd P.536 (1993) T. Tsutsui, D. U. Kim “Inorganic and Organic Electroluminescence Conference” (1996, Berlin)

Claims (15)

In the organic electroluminescence device in which an organic layer having a light emitting region is provided between an anode and a cathode, at least one of the constituent layers of the organic layer is an aminostyryl represented by the following general formula [I] An organic electroluminescent device comprising an aminostyryl compound layer composed of a compound and having a hole blocking layer on the cathode side of the aminostyryl compound layer.

[However, in the said general formula [I], X < ¹ > is group represented by either of the following general formula (1)-(7).

(However, in the general formulas (1) to (3), at least one of R ^{1 to} R ⁴ is a group selected from a halogen atom, a nitro group, a cyano group, and a fluoroalkyl group, and the others are hydrogen atoms. , An alkyl group, an aryl group, an alkoxy group, a halogen atom, a nitro group, a cyano group, and a fluoroalkyl group, which may be the same or different, and the above general formula (4) In (7), at least one of R ^{5 to} R ¹⁰ is a group selected from a halogen atom, a nitro group, a cyano group and a fluoroalkyl group, and the others are a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, A group selected from a halogen atom, a nitro group, a cyano group and a fluoroalkyl group, which may be the same or different).
Moreover, Y ¹ is a group represented by the following general formula (8) or (9), Y ² is the following general formula (8), a group represented by (9) or (10).

(However, in the general formulas (8) to (10), R ¹¹ and R ¹² are groups selected from a hydrogen atom, an alkyl group which may have a substituent, and an aryl group which may have a substituent. And they may be the same or different, and R ^{13 to} R ³⁵ are each a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. A group selected from an alkoxy group, a halogen atom, a nitro group, a cyano group, and a fluoroalkyl group, which may have the same, or they may be the same or different. In the general formula [I], X ¹ is a group represented by any one of the following structural formulas (11) to (14),

Y ¹ and Y ² are groups represented by the following general formula (8) or (9).

(However, in the general formulas (8) and (9), R ¹¹ and R ¹² are the same as those described above, and R ^{13 to} R ³⁰ are the same as those described above. The organic electroluminescent element according to claim 1, which is a trifluoromethyl group.   The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer of the organic multilayer structure includes the aminostyryl compound layer. The described organic electroluminescent device.   The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the hole transport layer of the organic multilayer structure is composed of the aminostyryl compound layer. The described organic electroluminescent device.   The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, the hole transport layer is composed of the aminostyryl compound layer, and the electron transport layer is composed of the aminostyryl compound layer. The organic electroluminescent device according to claim 1, wherein the hole blocking layer is present on the cathode side of the electron transporting aminostyryl compound layer.   The organic layer has an organic multilayer structure in which a hole transport layer, a light-emitting layer, and an electron transport layer are stacked, and at least the light-emitting layer of the organic multilayer structure includes the aminostyryl compound layer. 1. The organic electroluminescent element as described in 1.   The light-emitting device using the organic electroluminescent element as described in any one of Claims 1-6.   The light-emitting device according to claim 7, which is configured as a display device. In the organic electroluminescent device in which the organic layer having the light emitting region is provided between the anode and the cathode, at least one of the constituent layers of the organic layer is represented by the following structural formulas (15) -1 to (15): -12, (16) -1 to (16) -12, (17) -1 to (17) -6, and (18) -1 to (18) -6. An organic electroluminescent device comprising an aminostyryl compound layer composed of an aminostyryl compound, wherein a hole blocking layer is present on the cathode side of the aminostyryl compound layer.

  The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the electron transport layer of the organic multilayer structure is composed of the aminostyryl compound layer. Organic electroluminescent device.   The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, and at least the hole transport layer of the organic multilayer structure is formed of the aminostyryl compound layer. Organic electroluminescent device.   The organic layer has an organic multilayer structure in which a hole transport layer and an electron transport layer are stacked, the hole transport layer is composed of the aminostyryl compound layer, and the electron transport layer is composed of the aminostyryl compound layer. The organic electroluminescent device according to claim 9, wherein the hole blocking layer is present on the cathode side of the electron-transporting aminostyryl compound layer.   The transport layer has an organic multilayer structure in which a hole transport layer, a light-emitting layer, and an electron transport layer are stacked, and at least the light-emitting layer of the organic multilayer structure includes the aminostyryl compound layer. The organic electroluminescent element described in 1.   The light-emitting device using the organic electroluminescent element of any one of Claims 9-13.   The light-emitting device according to claim 14 configured as a display device.

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