CN116982407A - Organic EL display device and method for manufacturing the same - Google Patents
Organic EL display device and method for manufacturing the same Download PDFInfo
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- CN116982407A CN116982407A CN202280021295.3A CN202280021295A CN116982407A CN 116982407 A CN116982407 A CN 116982407A CN 202280021295 A CN202280021295 A CN 202280021295A CN 116982407 A CN116982407 A CN 116982407A
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- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
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- G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED
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Abstract
The present invention provides an organic EL display device and a method for manufacturing the same, wherein the organic EL display device including a pixel dividing layer and a spacer is manufactured by a simple method, and the organic EL display device has high reliability as a flexible display device and can inhibit external light reflection. An organic EL display device comprising a substrate, an organic EL layer, and a second electrode, wherein the substrate comprises a first electrode, a pixel dividing layer, and a spacer on a base material, and when the maximum value of the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is Ramax, ramax is 1.0nm to 50 nm.
Description
Technical Field
The present invention relates to an organic EL display device having a plurality of display pixels formed in a matrix shape and a method for manufacturing the same.
Background
The organic EL display device is attracting attention as a next-generation flat panel display. The organic EL means electroluminescence of an organic EL layer formed of an organic compound provided between 2 electrodes. The display device using the organic EL light-emitting element is an organic EL display device. Since a self-luminous organic EL display device can display an image with a wide viewing angle, a high-speed response, and a high contrast, and can be made thin, light-weight, and flexible by using a substrate such as thin glass or plastic resin, research and development have been advanced in recent years. Flexible organic EL display devices are expected to be used in various fields such as flexible that can be bent without being divided, rollable that can be rolled up, foldable that can be folded, and the like.
However, such a flexible organic EL display device may be peeled off from the substrate and the organic EL layer by a manufacturing process or a use method such as bending or folding, and as a result, the reliability of the organic EL display device may be lowered (for example, see patent literature 1).
On the other hand, when a mobile device is manufactured, as a display device, it is necessary to maintain display quality in various environments both indoors and outdoors, and in particular, in the case of suppressing external light reflection, a combination with a circularly polarizing plate, blackening of a substrate, and the like have been proposed (for example, see patent literature 2).
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2020-87935
Patent document 2: japanese patent application laid-open No. 2004-281365
Disclosure of Invention
Problems to be solved by the invention
However, in the organic EL display device described in patent document 1 in which the inverted cone-shaped spacers are provided on the pixel dividing layers in order to suppress peeling due to flexibility, it is difficult to set materials and manufacturing conditions due to the characteristics of the shape of the spacers, and there are problems such as failure to perform the simultaneous processing of the pixel dividing layers and the spacers, and a reduction in yield of the panel and a significant increase in cost.
In addition, although some suppression of external light reflection can be expected by coloring in the organic EL display device described in patent document 2 in which the first electrode and the pixel dividing layer are blackened for the purpose of suppressing external light reflection, suppression of external light reflection is insufficient due to the smoothness of the reflecting surface.
Accordingly, an object of the present invention is to provide an organic EL display device and a method for manufacturing the same, which are capable of suppressing external light reflection while improving reliability as a flexible display device by manufacturing the organic EL display device including the formation of a pixel dividing layer and a spacer by a simple method.
Means for solving the problems
An organic EL display device of the present invention is an organic EL display device having a substrate, which has a first electrode, a pixel dividing layer, and a spacer on a base material, and an organic EL layer and a second electrode, wherein when the maximum value of the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is Ramax, ramax is 1.0nm to 50 nm.
The method for manufacturing an organic EL display device according to the present invention is a method for manufacturing an organic EL display device having a substrate, which has a first electrode, a pixel dividing layer, and a spacer on a base material, and an organic EL layer and a second electrode, and includes a step of processing the pixel dividing layer and the spacer together, wherein the photomask used for the processing together is a halftone photomask having a light transmitting portion, a light shielding portion, and a semi-transmitting portion.
ADVANTAGEOUS EFFECTS OF INVENTION
In the organic EL display device of the present invention, the organic EL display device including the formation of the pixel dividing layer and the spacers can be manufactured by a simple method, and the peeling of the organic EL layer is not performed, and the reflection of external light can be suppressed by increasing the diffuse reflection light of the substrate.
Drawings
Fig. 1 is a schematic cross-sectional view of an organic EL display device according to the present invention.
FIG. 2 is a schematic cross-sectional view of a substrate as an example of the present invention.
FIG. 3 is a schematic cross-sectional view of Ra1 and Ra2 in the present invention.
Fig. 4 is a schematic view of the taper angle of the pixel division layer in the present invention.
Fig. 5 is a schematic cross-sectional view of a typical organic EL display device.
Fig. 6 is a schematic view of a first electrode and a halftone photomask according to an embodiment of the present invention.
FIG. 7 is a schematic view of a bending test according to an embodiment of the present invention.
Fig. 8 is a schematic view of an organic EL display device according to an embodiment of the present invention.
Fig. 9 is a schematic view of a light-emitting element in the embodiment of the invention.
Detailed Description
Hereinafter, embodiments (hereinafter, referred to as "embodiments") for carrying out the present invention will be described in detail. The present invention should not be limited to the embodiments described below.
< organic EL display device >)
The organic EL display device of the present invention is an organic EL display device having a plurality of display pixels formed in a matrix. The organic EL layer is classified into top emission and bottom emission according to the direction in which light emission is extracted, but is not particularly limited. The driving method is also broadly classified into a passive driving type in which electrodes are divided into columns and rows and only display pixels interposed between the electrodes emit light, and an active driving type in which a plurality of TFTs are provided in each display pixel and are switched, and is not particularly limited.
An organic EL display device of the present invention is an organic EL display device having a substrate, which has a first electrode, a pixel dividing layer, and a spacer on a base material, and an organic EL layer and a second electrode, wherein when the maximum value of the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is Ramax, ramax is 1.0nm to 50 nm.
Fig. 1 is a schematic cross-sectional view of an organic EL display device according to an example of the present invention. In the organic EL display device, a first electrode 2 is provided on a substrate 1. The substrate 1 has a pixel dividing layer 3 in a region where the first electrode 2 is not present (hereinafter, the region where the first electrode 2 is not present on the substrate 1 may be referred to as a gap of the first electrode), and a spacer 4 on the pixel dividing layer. In the organic EL display device, a cell having the first electrode, the pixel dividing layer, and the spacer on the base material is referred to as a substrate. Further, the organic EL layer 5 and the second electrode 6 are provided on the substrate, thereby forming an organic EL display device.
< substrate >
In the organic EL display device of the present invention, the substrate includes, as minimum units, only members including the base material 1, the first electrode 2, the pixel dividing layer 3, and the spacers 4, which will be described later. If the minimum unit is provided, the substrate may have a configuration (for example, the configuration of fig. 2) including a wiring, a TFT7, a pattern antenna, a planarizing layer 8, and the like. In the present invention, the wiring, TFT7, sensors, pattern antenna, etc., and the planarizing layer 8, etc., which are the base of the first electrode 2, are considered as a part of the substrate 1.
The wiring is often connected to an external device through an FPC (Flexible Printed Circuit ) for driving. In addition, in addition to the TFT7, a camera, an ID, a sensor such as fingerprint reading and illuminance, a pattern antenna for communication and power supply, and the like may be provided. In the substrate 1 thus integrated with various functions, it is preferable to provide the planarizing layer 8. By providing the planarizing layer 8, the substrate 1 can be planarized by covering the irregularities such as the wiring and the TFT7 before forming the first electrode 2. By planarizing the substrate 1, defects in the first electrode 2, the pixel dividing layer 3, and the spacer 4 provided on the substrate can be prevented, and a high-quality substrate can be obtained. Fig. 2 is a schematic cross-sectional view of a substrate as an example of the present invention.
< substrate >
As the base (base) 1a of the substrate 1 in fig. 1 and the substrate 1 in fig. 2, which is a substrate lower than the TFT7, a substrate which is preferable for supporting the display device and carrying in subsequent steps, such as a metal, glass, or a resin film, can be appropriately selected. Particularly in the case where flexibility is required, a resin film is preferable.
As the glass, soda lime glass, alkali-free glass, or the like can be used. The thickness of the glass may be any thickness sufficient to ensure mechanical strength. Since the material of the glass is preferably such that the amount of eluted ions from the glass is smaller, alkali-free glass is preferable, and SiO-implemented glass can be used 2 Etc. soda lime glass of barrier coatings.
As a material of the resin film, a resin material selected from the group consisting of a polybenzoxazole resin, a polyamideimide resin, a polyimide resin, a polyamide resin, and a poly (p-xylene) resin is preferable in view of excellent light transmittance. The base material may contain these resin materials alone or in combination of plural kinds.
For example, in the case of forming a substrate from a polyimide resin, the substrate may be formed by applying a solution containing a polyamic acid (containing a partially imidized polyamic acid) or a soluble polyimide resin, which is a polyimide resin precursor, to a support substrate and firing the solution.
In addition, since the light-emitting element is known to have low resistance to oxygen and moisture, an appropriate gas barrier layer may be provided as a base material. In particular, in the case of a resin film, an inorganic thin film is laminated and used, whereby a highly reliable display device can be obtained. Further, the substrate may be provided with wirings, TFTs 7, a planarizing layer 8, and the like.
< first electrode >)
The first electrode 2 in the present invention needs to be a light-transmissive electrode in the case of the bottom emission type, and needs to be a light-reflective electrode in the case of the top emission type.
In the case of the bottom emission type, for example, transparent conductive metal oxides such as tin oxide, indium oxide, and Indium Tin Oxide (ITO), metals such as gold, silver, and chromium, inorganic conductive materials such as copper iodide, and copper sulfide, conductive polymers such as polythiophene, polypyrrole, and polyaniline, and the like can be used, and the type is not particularly limited.
In the case of the top emission type, a material which exhibits high reflectance to visible light and low resistance at a certain thickness or more is preferable. Further, the material selection is also required in view of wet etching, cleaning, storage, and weather resistance under the use environment as the subsequent steps. Particularly, ag or an Ag alloy film containing Ag as a main body is useful because it has high reflectance. As the Ag alloy film, agPdCu, agTiCu and the like containing Ag as a main component can be used, and lamination of these Ag alloy films with an oxide conductive film such as an ITO film or an IZO film is preferable because low contact resistance with the organic EL layer can be achieved. In addition, al or an Al alloy film containing Al as a main body is also preferable as the top emission type first electrode. An al—ni alloy film containing 0.1 to 2 atomic% of Ni is preferable because it has a high reflectance equivalent to that of pure Al. Further, a reflective metal film such as molybdenum (Mo) or tungsten (W) may be used.
The resistance of the first electrode is not limited as long as a sufficient current can be supplied to light emission of the light-emitting element, but is desirably low in terms of power consumption of the light-emitting element. For example, when ITO is 300 Ω/≡or less, it is currently desirable to use a low-resistance product because ITO of about 10Ω/≡can be supplied as an element electrode. The thickness of the first electrode may be arbitrarily selected according to characteristics such as transmittance and resistance, and may be generally in the range of 100 to 300 nm.
The method for forming the first electrode may use a known method. For example, patterning may be performed by etching using a photoresist after film formation by a vacuum film formation method such as sputtering.
< Pixel splitting layer >)
In the organic EL display device of the present invention, the pixel dividing layer 3 is formed in the space of the first electrode 2. The display pixels can be divided by forming the pixel dividing layer in the gaps of the first electrode. That is, by patterning the pixel dividing layer in the space of the first electrode, the exposed portion of the first electrode is defined, and only the opening portion of the pixel separating layer functions as a display pixel. In addition, the pixel dividing layer covers the periphery of the linear or island-shaped first electrode, thereby preventing short circuit at the edge of the first electrode and disconnection of the second electrode, and improving the reliability of the display device. In the organic EL display device of the present invention, the pixel dividing layer is also formed at a portion other than the space of the first electrode as needed.
In the present invention, when the maximum value of the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is Ramax, ramax is 1.0nm to 50 nm. Further, it is more preferable that the surface roughness (Ra 1) of the pixel division layer is Ramax. In addition, both the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer may be Ramax.
In the present invention, an Atomic Force Microscope (AFM) used for measuring surface roughness is generally used to measure a substrate of an organic EL display device placed on a horizontal plane from above vertically, and the ranges of Ra1 and Ra2 are shown in fig. 3. Accordingly, in the present invention, the "surface roughness of the pixel division layer" refers to the surface of the pixel division layer that can be measured by AFM, that is, the surface substantially parallel to the substrate, out of the surfaces of the pixel division layer that are in contact with the organic EL layer.
Further, since the spacers are formed on the pixel dividing layer, the portions without the spacers become interfaces with the organic EL layer. Conventionally, since adhesion between the pixel dividing layer and the organic EL layer is poor, peeling is likely to occur, and particularly, a problem is large in flexible products. In the present invention, the anchoring effect can be obtained by setting the surface roughness (Ra 1) of the pixel dividing layer to 1.0nm or more, and the adhesion to the organic EL layer can be improved by setting the surface roughness to 5.0nm or more, more preferably 20nm or more.
In addition, although the anchoring effect can be obtained when the surface roughness (Ra 1) of the pixel dividing layer is 1.0nm or more, it is preferable to set the surface roughness to 50nm or less for the purpose of suppressing pinholes in the second electrode and defects in a sealing process described later. In the case where the adhesion is improved by a large Ra1, it is effective to ensure that the interface between the pixel-divided layer and the organic EL layer is as large as possible, and in the case where Ra1 is larger than the surface roughness Ra2 of the spacer described later, that is, ra1 is Ramax, the area of the interface between the substrate and the organic EL layer is preferably 50% or more of the area of the interface between the pixel-divided layer and the organic EL layer. This means that the pixel dividing layer is 50% or more of the surface area of the substrate.
Further, the edge of the pixel dividing layer is preferably gently tapered because it causes the second electrode to be broken. Here, the positive taper means: an angle formed by a tangent line at an interface between the first electrode and the pixel dividing layer and a tangent line at a position of 50% of a film thickness of a maximum thickness of the pixel dividing layer in a surface of a tapered portion of the pixel dividing layer (hereinafter, this angle may be referred to as a taper angle of the pixel dividing layer) is less than 90 degrees. In the present invention, in order to obtain a highly reliable display device in which disconnection of the second electrode is suppressed, the taper angle of the pixel dividing layer is preferably less than 60 degrees, more preferably less than 50 degrees.
The taper angle of the pixel division layer will be specifically described with reference to fig. 4. In fig. 4, a first electrode 2 is provided on a substrate 1. The first electrode 2 has a pixel division layer 3 in a space, and further has a spacer 4 on the pixel division layer. An angle (B) formed by a tangent line at the interface of the first electrode and the pixel division layer and a tangent line at a position (point a) of 50% film thickness of the maximum thickness of the pixel division layer in the surface of the tapered portion of the pixel division layer is defined as a taper angle of the pixel division layer.
The pixel-dividing layer is not limited to any one of known organic or inorganic substances, and preferably includes a cured film of a photosensitive resin composition containing an alkali-soluble resin, in view of easy adjustment of surface roughness. The pixel dividing layer may be a single layer or a plurality of layers, and for example, when the pixel dividing layer is a plurality of layers, a surface substantially parallel to the substrate, which is a measurement target of the surface roughness, is preferably a cured film of a photosensitive resin composition containing an alkali-soluble resin.
The photosensitive resin composition preferably contains (a) an alkali-soluble resin, (B) a photosensitive agent, and (C) an organic solvent, and may further contain (D) a coloring material, and (E) a lyophobic material. As the photosensitive resin composition, a pattern processing using photosensitivity can be realized by combining (a) an alkali-soluble resin and (B) a photosensitiser. In addition, by containing the organic solvent (C), a state of varnish can be formed, and coatability may be improved. Further, by containing the coloring material (D) in the photosensitive resin composition, the pixel dividing layer can be blackened. In addition, by containing the lyophobic material (E), lyophobicity can be imparted to the pixel dividing layer. The difference between the (D) coloring material, (E) lyophobic material, and the (a) alkali-soluble resin in the exposure sensitivity and dissolution rate is that the surface roughness of the pixel dividing layer and the spacer is increased and the surface roughness of the pixel dividing laminated spacer can be adjusted by using a halftone mask described later. The photosensitive resin composition may further contain other components.
The pixel division layer may be formed by a known method. Among them, the wet coating method is preferable in that a thin film can be uniformly formed on a large substrate. Examples of the wet coating method include spin coating, slit coating, dip coating, spray coating, and printing.
The thickness of the pixel dividing layer is usually 0.3 μm to 10 μm, and is not particularly limited as long as it is sufficient to cover the irregularities of the first electrode. In addition, the pixel division layer must be patterned, and the residue in the removed portion may cause defects such as short circuit and black dot. In addition, in order to support the structure covering the second electrode and to secure the strength of the display device in the subsequent steps, it is necessary to fabricate spacers on the pixel dividing layer.
Alkali-soluble resin (A)
The alkali solubility in the present invention means: a solution obtained by dissolving a resin in gamma-butyrolactone (GBL) is applied to a silicon wafer, prebaked at 120 ℃ for 4 minutes to form a prebaked film having a film thickness of 10 [ mu ] m + -0.5 [ mu ] m, immersed in a 2.38 mass% aqueous solution of tetramethylammonium hydroxide at 23 ℃ + -1 ℃ for 1 minute, rinsed with pure water, and the dissolution rate obtained from the film thickness reduction at this time is 50 nm/min or more.
From the viewpoint of improving heat resistance, (a) the alkali-soluble resin preferably has an aromatic carboxylic acid structure. In the present invention, the aromatic carboxylic acid structure means a carboxylic acid structure directly covalently bonded to an aromatic ring.
The alkali-soluble resin (a) preferably contains 1 or more resins selected from the group consisting of acrylic resins, phenolic resins, polysiloxane resins, cardo resins, polyimide precursor resins, polybenzoxazole resins, and polybenzoxazole precursor resins.
Among these resins, (a) the alkali-soluble resin preferably contains a polyimide resin, a polyimide precursor resin, a polybenzoxazole resin, and/or a polybenzoxazole precursor resin, from the viewpoint of achieving both heat resistance and chemical resistance. If the chemical resistance is high, film damage in processing the pixel division layer by wet etching is preferably reduced. In addition, polyimide precursor resins are particularly preferred in view of the low outgassing under high temperature conditions. Further, from the viewpoint of improving the alkali solubility, a polyimide precursor resin having an amic acid structure is more preferable.
Silicon dioxide particle in pixel dividing layer
The pixel-dividing layer in the organic EL display device of the present invention preferably contains (a) silica particles having a primary particle diameter of 5 to 30nm (hereinafter, sometimes referred to as component (a)). The pixel-dividing layer further preferably contains a (D) coloring material described later in addition to the component (a), and in this case, further preferably contains a (D1) organic pigment described later as the (D) coloring material, and further preferably contains a (b) organic pigment described later as the (D1) organic pigment. The component (a) preferably has a primary particle diameter of 5 to 30nm and an aspect ratio (major diameter/minor diameter) of 1.0 to 1.5. By containing the component (a), the uniformity of the opening width of the opening is improved, and the effect of reducing the luminance unevenness is exhibited. The primary particle diameter herein means the long diameter of the particles, and silica particles having a primary particle diameter of 5 to 30nm mean particles having a primary particle diameter in the range of 5 to 30 nm. The term "aspect ratio (long diameter/short diameter)" as used herein refers to a value obtained by rounding the second bit after dividing the long diameter by the decimal point of the value obtained by dividing the short diameter in the primary particle diameter of the silica particles.
The silica particles referred to herein mean SiO in the weight after water removal 2 Particles having a content of 90 wt% or more, particles made of silica (silicic anhydride), particles made of silica hydrate (hydrous silicic acid), and particles made of quartz glass. The form of the aqueous silicic acid is not particularly limited, and particles formed from orthosilicic acid, metasilicic acid and/or metadisilicic acid are also referred to herein as silica particles. The weight after water removal means the weight obtained by subtracting the weight of the water in the particles from the weight of the particles.
However, in the core-shell type composite particles, siO is not contained 2 The surface treatment agent and the coating layer applied as a shell on at least a part of the surface of the core particle, for example, the particle formed of an organic polymer, the organic pigment or the inorganic pigment, even if SiO is contained 2 No matter SiO 2 The content of (2) is defined as the content of silica particles alone. On the other hand, for the core containing SiO 2 And SiO in the weight after water removal 2 The core-shell composite particles having a content of 90 wt% or more are defined as silica particles. That is, the component (a) is filled in a form of being dispersed as particles in the pixel dividing layer. (a) The particle structure of the component is not particularly limited, and may have internal voids.
Examples of silica particles other than the silica particles, the silica hydrate particles and the silica particles, include SiO in weight after water removal 2 Silica particles comprising a composite oxide of silicon and a metal, the silica particles having a content of 90 wt.% or more. Examples of the metal referred to herein include zirconium, titanium, and cerium. The term "silica particles containing hafnium atoms" is defined as a mixture of silica particles and hafnium atoms (hereinafter, may be referred to as "component (c)").
In view of further reducing the luminance unevenness of the organic EL display device, the component (a) more preferably contains silica particles having a primary particle diameter of 5 to 20nm, and still more preferably contains silica particles having a primary particle diameter of 5 to 15 nm. The primary particle diameter referred to herein means the long diameter of silica particles. More preferably, the silica particles have an aspect ratio of 1.0 to 1.3, and still more preferably, the silica particles have an aspect ratio of 1.0 to 1.2. When the aspect ratio is 1.0, the silica particles may be regarded as spherical silica particles.
(a) The component (a) and the silica particles other than the component (a) can be discriminated and determined from the element mapping information by: the product obtained by cutting the pixel division layer and the spacer layer thinly is used as an observation sample, and the smoothness of the cross section is improved by polishing preferably by a pretreatment by ion milling, more preferably by a pretreatment by Focused Ion Beam (FIB) processing, and the cross section with improved smoothness is analyzed by transmission electron microscopy-energy dispersive X-ray spectrometry (TEM-EDX) for a portion of the pixel division layer or the spacer layer lying in the range of 0.2 to 0.8 μm in the film depth direction from the outermost layer. In addition, transmission electron microscopy-electron energy loss spectroscopy (TEM-EELS) or scanning transmission electron microscopy-energy dispersive X-ray spectroscopy (STEM-EDX) can also be used for the analysis.
Specifically, by measuring a captured image obtained by observing a sample at a magnification of 50000 times by a transmission electron microscope-energy dispersive X-ray spectrometry (TEM-EDX) using an image analyzer "Mac-View" (manufactured by MOUNTECH corporation), it is possible to distinguish silica particles belonging to the component (a) from silica particles not belonging to the component (a). That is, 30 silica particles in the TEM image are randomly selected from the cross section of the pixel division layer, and the long diameter, the short diameter, and the aspect ratio in the TEM image are measured, respectively, and silica particles having a long diameter (nm) of 5 to 30nm and an aspect ratio in the range of 1.0 to 1.5 are defined as the component (a). In the case where the short diameter and the long diameter of 1 silica particle in the TEM image are equal to each other, that is, in the case of a perfect circle, the diameters thereof are regarded as long diameters.As representative values showing characteristics of the silica particles belonging to the component (a), an average value of primary particle diameters, that is, an average value of long diameters is calculated, and a value obtained by rounding off the first decimal place and an average value of aspect ratios, that is, an average value of aspect ratios of the respective silica particles belonging to the component (a) are calculated, and a value obtained by rounding off the second decimal place is used. Here, siO having a contact with the surface of particles made of a polymer, organic pigment, inorganic pigment, or the like 2 Analysis was performed excluding. The length and length to width ratio of the silica particles contained in the spacer layer can be measured by the same method.
The pixel-dividing layer included in the organic EL display device of the present invention may further contain silica particles not belonging to the component (a), that is, silica particles having a primary particle diameter of less than 5nm or more than 30nm, and silica particles having an aspect ratio (long diameter/short diameter) of more than 1.5. Examples of silica particles not belonging to the component (a) include "Admafine" (registered trademark) SO-E2, SO-E4 (all of which are manufactured by Admatechs Co., ltd.), KE-P10, and KE-S10 (all of which are manufactured by Japanese catalyst Co., ltd.).
The pixel-dividing layer provided in the organic EL display device of the present invention may further contain SiO in a proportion of less than 90% by weight based on the weight of the organic EL display device after water removal 2 And not particles of silica particles in the present specification. Examples of the particles not belonging to the silica particles include silica disclosed in Japanese patent application laid-open No. 2018-97251: polymer ratio = weight ratio 70:30, "ATLAS" (registered trademark) 100 (manufactured by CABOT corporation) as organic-inorganic composite particles.
The average primary particle diameter of the silica particles contained in the pixel-dividing layer of the organic EL display device of the present invention is preferably 5 to 30nm, more preferably 5 to 25 μm, from the viewpoint of suppressing luminance unevenness. The average aspect ratio (long diameter/short diameter) is preferably 1.0 to 1.3, more preferably 1.0 to 1.2. That is, even when the pixel-dividing layer included in the organic EL display device of the present invention contains silica particles not belonging to the component (a), the average primary particle diameter of all the silica particles contained is preferably 5 to 30nm. In the same manner, the average aspect ratio (long diameter/short diameter) is preferably 1.0 to 1.3. The silica particles referred to herein include both silica particles not belonging to the component (a) and the component (a). The average primary particle diameter referred to herein means: for the above-mentioned captured image obtained by observing a cross section of the pixel division layer from the outermost layer thereof in the range of 0.2 to 0.8 μm in the film depth direction at a magnification of 50000 times by a transmission electron microscope-energy dispersive X-ray spectrometry (TEM-EDX), 30 silica particles were randomly obtained by using an image analyzer (Mac-View, manufactured by MOUNTECH corporation), and the first digit was rounded after the decimal point of the average value of the long diameters of all the silica particles. The term "average aspect ratio (long/short)" as used herein means: the average value of the long diameter divided by the short diameter among the 30 primary particles of all the silica particles randomly acquired in the image is obtained by rounding the second bit after the decimal point of the average value. Silica particles having an average primary particle diameter of 5 to 30nm mean particles having an average primary particle diameter of 5 to 30nm, and silica particles having an average aspect ratio of 1.0 to 1.3 mean particles having an average aspect ratio of 1.0 to 1.3.
The specific surface area of the component (a) corresponding to the primary particle diameter is preferably 50 to 500m 2 Preferably 200 to 400m 2 And/g. The specific surface area referred to herein is a specific surface area measured by the BET method using nitrogen as the adsorption gas. (a) The surface of the component may be porous or nonporous, and may have an internal surface area.
Examples of the functional group of the component (a) on the surface thereof include a reactive residue of a surface modifying group containing an ethylenically unsaturated double bond group, a silanol group, an alkoxysilyl group, a trialkylsilyl group, and a diphenylsilyl group. Among them, a reaction residue having a surface modifying group containing an ethylenically unsaturated double bond group is preferable from the viewpoint of further reducing the luminance unevenness. The term "reaction residue" as used herein, which includes a surface modifying group comprising an ethylenically unsaturated double bond group, refers to: and a radical residue after the radical polymerization of the ethylenically unsaturated double bond group containing the surface-modifying group of the ethylenically unsaturated double bond group by light and/or heat. More preferably, the component (a) contains silica particles having a reaction residue of a surface modification group containing an ethylenically unsaturated double bond group on the particle surface, and the reaction residue of the surface modification group containing an ethylenically unsaturated double bond group has a structure represented by formula (3) and/or a structure represented by formula (4). The reaction residue of the surface modifying group containing an ethylenically unsaturated double bond group is more preferably a residue produced by radical polymerization reaction with a compound having 2 or more radical polymerizable groups in the molecule, which will be described later.
[ chemical formula 1]
In the formula (3), R 17 16 Represents a hydrogen atom or a methyl group. R is R 18 17 A divalent hydrocarbon group having 1 to 7 carbon atoms. j and k are integers, each independently representing 0 or 1. Where j is 1, k is 1. 'Qingzhi' for treating coronary heart disease 1 Represents a bond site with a carbon atom.
* 2 The bonding site of the silicon dioxide particles to the silicon atom is represented by the bonding site of the silicon dioxide particles to the silicon atom. R is R 19 18 Represents an alkyl group having 1 to 3 carbon atoms. m and n are integers, m represents 1-3, and n represents 0-2. Where m+n=3 is satisfied.
[ chemical formula 2]
In the formula (4), R 20 19 Represents a hydrogen atom or a methyl group. R is R 21 20 Represents an oxyalkylene group having 1 to 3 carbon atoms. r is an integer of 1 to 4. 'Qingzhi' for treating coronary heart disease 3 Represents a bond site with a carbon atom.
* 4 The bonding site of the silicon dioxide particles to the silicon atom is represented by the bonding site of the silicon dioxide particles to the silicon atom.
The component (a) having the structure represented by formula (3) can be obtained by: a surface modifying group derived from an organoalkoxysilane compound having an ethylenically unsaturated double bond group is introduced by dehydration condensation reaction with silanol groups on the surface of silica particles, and the ethylenically unsaturated double bond group contained in the surface modifying group is subjected to radical polymerization by light and/or heat.
Examples of the organoalkoxysilane compound having an ethylenically unsaturated double bond group include vinyltrimethoxysilane, vinyltriethoxysilane, p-styryltrimethoxysilane, p-styryltriethoxysilane, 3-methacryloxypropyl methyldimethoxysilane, 3-methacryloxypropyl methyldiethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-methacryloxypropyl triethoxysilane, 3-acryloxypropyl methyldimethoxysilane, 3-acryloxypropyl methyldiethoxysilane, 3-acryloxypropyl trimethoxysilane, 3-acryloxypropyl triethoxysilane, allyl trimethoxysilane, and allyl triethoxysilane.
The component (a) having the structure represented by the formula (4) as the reaction residue can be obtained by: a surface modification group derived from an isocyanate compound having an ethylenically unsaturated double bond group is introduced by urethanization reaction with a silanol group on the surface of silica particles, and the ethylenically unsaturated double bond group contained in the surface modification group is subjected to radical polymerization reaction by light and/or heat. Examples of the isocyanate compound having an ethylenically unsaturated double bond group include 2-methacryloyloxyethyl isocyanate, 2-acryloyloxyethyl isocyanate, and 2- (2-methacryloyloxyethyl) ethyl isocyanate.
Further, by sequentially modifying the surface modifying group derived from an organoalkoxysilane compound having an ethylenically unsaturated double bond group and the surface modifying group derived from an isocyanate compound having an ethylenically unsaturated double bond group on the surface of silica particles, it is possible to obtain component (a) having a structure represented by formula (3) and a structure represented by formula (4) in the reaction residue.
For example, in order to improve the dispersion stability of the component (a) in the negative photosensitive composition, the component (a) preferably has a trialkylsilyl group, and more preferably has a trimethylsilyl group. The trimethylsilyl group can be introduced into the component (a) by converting a hydrogen atom in a silanol group on the surface of the silica particles into a trimethylsilyl group using a trimethylsilylating agent. Examples of the trimethylsilylating agent include hexamethyldisilazane and trimethylalkoxysilane, which can be introduced by deamination and dehydration condensation, respectively. By improving the dispersion stability of the component (a), the luminance unevenness can be reduced more stably in some cases.
In view of further reducing the uneven brightness, the component (a) preferably contains silica particles having sodium atoms. Examples of the form of sodium atom include ion (Na + ) Salts with silanol groups (Si-ONa). The content of sodium atoms in the component (a) is preferably 100 to 5000 ppm by weight. Silica particles having sodium atoms can be synthesized by the reaction of strongly basic sodium silicate as a silicon source with an inorganic acid as a strong acid under alkaline conditions. The sodium atom of the silica particle may be detected at a central portion at the intersection point of the major axis and the minor axis in the captured image of the cross section of the primary particle using the TEM-EDX described above.
Regarding the content of the component (a), from the viewpoint of suppressing luminance unevenness, siO is used in the pixel dividing layer 2 The amount is preferably 1 to 50% by weight, more preferably 5 to 20% by weight. In addition, from the same point of view, all silicon dioxide components in the pixel dividing layer are also represented by SiO 2 The amount is preferably 1 to 50% by weight, more preferably 7 to 30% by weight. Herein referred to as SiO 2 The converted content refers to: based on the technical knowledge of the person skilled in the art,the weight of the moisture in the silica particles varying with the thermal history is removed to convert the content.
In the organic EL display device of the present invention, the pixel-dividing layer preferably further contains 1 to 50 ppm by weight of (c) hafnium atoms (hereinafter, may be referred to as (c) component) from the viewpoint of further reducing the unevenness of brightness. More preferably 1 to 30 ppm by weight. The component (c) is preferably contained in the pixel dividing layer as inorganic particles containing hafnium atoms.
Examples of the inorganic particles containing the component (c) include hafnium oxide (HfO 2 ) A complex oxide of a metal other than hafnium and hafnium, a solid solution of an oxide of a metal other than hafnium and hafnium oxide, hafnium oxynitride, a complex oxynitride of a metal other than hafnium and hafnium, and a solid solution of an oxynitride of a metal other than hafnium and hafnium oxynitride. Among them, hafnium oxide (HfO is preferable in view of excellent effect of reducing luminance unevenness 2 ) Or a complex oxide of a metal other than hafnium and hafnium, more preferably a complex oxide of zirconium and hafnium (ZrO 2 -HfO 2 )。
Examples of the inorganic particles containing the component (c) include those commercially available in the form of powder, such as Hafnium oxide P, hafnium oxide R, hafnium oxide S (all of them are manufactured by ATI METALS corporation) and Hafnium oxide fine particles (manufactured by the high purity chemical research). As another method, in the process of preparing a pigment dispersion liquid containing the component (b) described later, fine particles generated by wet grinding the surface of a grinding medium containing the component (c) with mechanical energy may be co-dispersed with the component (b), whereby the component (c) is contained in the finally obtained pixel-divided layer.
The content of the component (c) may be determined by cutting a portion of the pixel-divided layer in the range of 0.2 to 0.8 μm in the film depth direction from the outermost layer, heating and ashing the pixel-divided layer at a temperature of 800 ℃ or higher using an electric furnace, further performing thermal decomposition with sulfuric acid, nitric acid and hydrofluoric acid, then performing thermal dissolution with dilute hydrochloric acid to obtain a solution, and using the solution as an analysis sample, and quantifying the solution by ICP (high frequency inductively coupled plasma) emission spectrometry. As an analysis device, PS3520VDDII (manufactured by Hitachi High-Tech Science) can be used.
(D) coloring Material
When coloring is required from the viewpoints of light shielding and reflection prevention, the photosensitive resin composition used in the present invention preferably contains (D) a coloring material. The photosensitive resin composition containing the (D) coloring material is preferable because the pixel-dividing layer is a layer containing the (D) coloring material, and the effects described below are obtained. The coloring material (D) is a compound that absorbs light of a specific wavelength, and particularly, a compound that is colored by absorbing light of a wavelength (380 to 780 nm) of visible light. By containing the coloring material (D), the cured film obtained from the photosensitive resin composition can be colored, and the coloring property can be imparted to color light transmitted through the cured film of the photosensitive resin composition or light reflected from the cured film of the photosensitive resin composition into a desired color. Further, light shielding properties can be imparted to shield (D) light of the wavelength absorbed by the coloring material from light transmitted through the cured film of the photosensitive resin composition or light reflected from the cured film of the photosensitive resin composition.
The content of the coloring material (D) used in the present invention is preferably 1 wt% or more, more preferably 10 wt% or more, and still more preferably 15 wt% or more in the pixel-dividing layer. When the content ratio is within the above range, light-shielding properties, colorability, or tintability can be improved. On the other hand, the content ratio is preferably 70% by weight or less, more preferably 65% by weight or less, and still more preferably 60% by weight or less. When the content ratio is within the above range, sensitivity at the time of exposure can be improved.
Examples of the coloring material (D) include known compounds such as (D1) organic pigments, (D2) inorganic pigments, and (D3) dyes that absorb light having a wavelength of visible light and are colored in white, red, orange, yellow, green, blue, or violet. These coloring materials may be used in combination of 2 or more kinds, or may be used in combination of 2 or more kinds. The pixel division layer obtained by combining 2 or more kinds is preferable because it has the effects described later. By combining 2 or more colors, the color matching property can be improved by matching light transmitted through or reflected from the cured film of the photosensitive resin composition to a desired color coordinate.
By using (D1) an organic pigment as (D) a coloring material, the characteristics of (D1) an organic pigment, that is, a chemical structure change or a functional group conversion function, can be utilized to adjust the transmission spectrum or absorption spectrum of a cured film of the photosensitive resin composition by transmitting or blocking light of a desired specific wavelength, and the like, thereby improving the color matching property. The details of such (D1) organic pigment are set forth later.
By using (D2) an inorganic pigment as (D) a coloring material, the heat resistance and weather resistance of the cured film of the photosensitive resin composition can be improved due to the characteristics of (D2) an inorganic pigment, that is, the excellent heat resistance and weather resistance. Examples of the inorganic pigment (D2) include zirconium nitride, zirconium oxide, titanium oxide, barium carbonate, zinc white, zinc sulfide, lead white, calcium carbonate, barium sulfate, white carbon, alumina white, silica, kaolin, talc, bentonite, iron oxide red, molybdenum chrome orange, chrome vermilion, yellow lead, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, chrome green, titanium cobalt green, cobalt chrome green, victoria green, ultramarine, prussian blue, cobalt blue, sky blue, cobalt silica blue, cobalt zinc silica blue, manganese violet, cobalt violet, graphite, and silver tin alloy; or particles of metals such as titanium, copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium or silver, oxides, composite oxides, sulfides, sulfates, nitrates, carbonates, nitrides, carbides or oxynitrides
Among them, in order to make the surface roughness (Ra 1) of the pixel dividing layer 1.0nm to 50nm, an inorganic pigment having a large specific gravity such as zirconium nitride is preferably dispersed. As will be described later, the reason for this is that pigment precipitation during development is expected in the pixel division layer belonging to the halftone exposure portion. The inorganic pigment has problems such as pigment aggregation, thickening, and sensitivity decrease with time, but the alkali solubility of an exposed portion, an unexposed portion, and a halftone exposed portion, which will be described later, can be suitably adjusted by setting the acid equivalent of the component (a) to 200g/mol or more and 500g/mol or less. If the acid equivalent of the component (a) is less than 200g/mol, for example, when a cured film of the positive photosensitive resin composition is obtained, the alkali solubility of the unexposed portion becomes high, and the difference in dissolution rate from the exposed portion becomes small, so that a desired pattern cannot be formed. By setting the acid equivalent to 200g/mol or more, the solubility of the unexposed portion can be suppressed, and a pattern with less residues in the opening portion due to the adhesion of the dissolved matter from the unexposed portion can be formed. Further, by setting the acid equivalent of the component (a) to 500g/mol or less, dispersion stabilization of zirconium nitride particles can be promoted, and a photosensitive resin composition excellent in storage stability can be obtained.
(D3) The dye is a compound that colors an object by chemisorption, strong interaction, or the like of a substituent such as an ionic group or a hydroxyl group in the dye with a surface structure of the object, and is generally soluble in a solvent or the like. In addition, in the coloring with a dye, since molecules are adsorbed to an object one by one, the coloring power is high and the color development efficiency is high. As the dye, for example, a direct dye, a reactive dye, a sulfur dye, a vat dye, a sulfur dye, an acid dye, a metal-containing acid dye, a basic dye, a mordant dye, an acid mordant dye, a disperse dye, a cationic dye, a fluorescent whitening dye, or the like can be classified. According to the material system, anthraquinone-based dyes, azo-based dyes, azine-based dyes, phthalocyanine-based dyes, methine-based dyes, oxazine-based dyes, quinoline-based dyes, indigo-based dyes, carbocationic-based dyes, vat-based dyes, pyrenone-based dyes, perylene-based dyes, triarylmethane-based dyes, xanthene-based dyes, and the like are exemplified, and anthraquinone-based dyes, azo-based dyes, azine-based dyes, methine-based dyes, triarylmethane-based dyes, xanthene-based dyes, and the like are preferable from the viewpoints of solubility in (C) an organic solvent and heat resistance.
Among them, in order to make the surface roughness (Ra 1) of the pixel dividing layer 1.0nm to 50nm, it is preferable to contain (D3-1) a salt-forming compound formed of an acid dye and a basic dye as (D) a coloring material. The reason for this is that by containing (D3-1) a salt-forming compound formed from an acid dye and a basic dye, precipitation of the dye upon development is expected in the pixel division layer belonging to the halftone exposure portion.
(D3-1) A salt-forming compound formed from an acid dye and a basic dye means a compound obtained by reacting an acid dye with a basic dye. Is a chemically stable compound obtained by a chemical (salt formation) reaction between an acidic dye having an anionic dye ion and a basic dye having a cationic dye ion.
The acid dye is a compound having an acidic substituent such as a sulfo group or a carboxyl group in the molecule of the dye, or an anionic water-soluble dye as a salt thereof. The acid dye includes dyes having an acid substituent such as a sulfo group or a carboxyl group, and classified as direct dyes. Among them, the acid dye preferably contains a xanthene acid dye, since the amount of the residue at the opening can be reduced. The xanthene acid dye more preferably contains rhodamine acid dyes such as c.i. acid red 50, 52, 289, and the like, from the viewpoint of further reducing the amount of the opening residues. In addition, from the viewpoint of improving the blackness of the cured film, the rhodamine-based acid dye further preferably contains c.i. acid red 52.
Basic dye is a compound having a basic group such as an amino group or an imino group in a molecule, or a salt thereof, and is a dye that becomes a cation in an aqueous solution. Among them, the basic dye preferably contains a triarylmethane basic dye in order to improve the blackness of the cured film. The triarylmethane-based basic dye more preferably contains c.i. basic blue 7 and/or c.i. basic blue 26, from the viewpoint of further improving the blackness of the cured film.
Salt-forming compounds of acid dyes and basic dyes can be synthesized by known methods. For example, when an aqueous acid dye solution and an aqueous basic dye solution are prepared separately and mixed slowly with stirring, a salt compound of the acid dye and the basic dye is produced as a precipitate. This salt-forming compound can be obtained by recovering it by filtration. The resulting salt-forming compound is preferably dried at about 60 to 70 ℃.
Further, blackening can be achieved by setting the content of the salt-forming compound in the photosensitive resin composition to 10 parts by weight or more relative to 100 parts by weight of the alkali-soluble resin (a), and opening residues can be reduced by setting the content to 75 parts by weight or less. By containing the salt-forming compound in this range, alkali solubility of an exposed portion, an unexposed portion, and a halftone exposed portion, which will be described later, can be appropriately adjusted.
In addition, when it is desired to improve the blackness of the cured film, (D3-2) a nonionic dye is preferably contained as (D) a coloring material.
(D3-2) nonionic dyes are dyes other than acid dyes and basic dyes, and refer to dyes having no ionic structure.
Examples of the nonionic dye include: c.i. disperse orange 5; c.i. disperse red 58; c.i. disperse blue 165; azo nonionic dyes such as solvent red 18; c.i. vat blue 4; c.i. disperse red 22, 60; c.i. disperse violet 26, 28, 31; c.i. disperse blue 14, 56, 60; c.i. solvent violet 13, 31, 36; and anthraquinone nonionic dyes such as c.i. solvent blue 35, 36, 45, 63, 78, 87, 97, 104, 122.
Among them, anthraquinone nonionic dyes are preferable from the viewpoint of improving the blackness of the cured film.
Organic pigment (D1)
Examples of the organic pigment (D1) used as the coloring material (D) include phthalocyanine pigments, anthraquinone pigments, quinacridone pigments, pyranthrone pigments, dioxazine pigments, thioindigo pigments, pyrrolopyrrole dione pigments, quinoline yellow pigments, reduction pigments, indoline pigments, isoindoline pigments, isoindolinone pigments, benzofuranone pigments, perylene pigments, aniline pigments, azo pigments, azomethine pigments, condensed azo pigments, carbon black, metal complex pigments, lake pigments, toner pigments, and fluorescent pigments. From the viewpoint of heat resistance, anthraquinone pigments, quinacridone pigments, pyranthrone pigments, pyrrolopyrrole dione pigments, benzofuranone pigments, perylene pigments, condensed azo pigments, and carbon black are preferable.
In the present invention, the photosensitive resin composition used in forming the pixel-dividing layer preferably contains an organic pigment from the viewpoint of imparting light-shielding properties to the pixel-dividing layer. The photosensitive resin composition contains an organic pigment, and the pixel-dividing layer is preferably a layer containing an organic pigment, since the following effects can be obtained. In this case, it is preferable that an organic black pigment and/or a mixed-color organic black pigment (hereinafter, may be referred to as component (b)) be further contained as the (D1) organic pigment.
Examples of the organic black pigment include benzodifuranone-based black pigments, perylene-based black pigments, and azomethine-based black pigments.
Examples of the benzodifuranone black pigment include pigments disclosed in international publication No. 2009/010521. As commercial products of the benzodifuranone-based Black pigment formed from the compound represented by the formula (5) described below, irgaphor Black (registered trademark) S0100CF, experimental Black 582 (all of the above are manufactured by BASF corporation) can be preferably used.
Examples of perylene black pigments include c.i. pigment black 31, c.i. pigment black 32, perylenetetracarboxylic acid benzimidazole or a derivative thereof, and pigments disclosed in international publication No. 2005/078023. As commercial products, spectrase (registered trademark) Black S0084, spectrasense Black L0086, spectrasense Black K0087, spectrasense Black K0088 (all of which are manufactured by BASF corporation) can be used.
Examples of the azomethine-based black pigment include pigments disclosed in U.S. patent application publication No. 2002-121228. As a commercially available product, chromofine Black A1103 (manufactured by dai refining industries, ltd.) can be used.
The color-mixed organic black pigment is a pigment mixture containing (b-1) at least one color organic pigment selected from the group consisting of organic yellow pigment, organic red pigment and organic orange pigment (hereinafter, sometimes referred to as (b-1) component) and (b-2) at least one color organic pigment selected from the group consisting of organic blue pigment and organic violet pigment (hereinafter, sometimes referred to as (b-2) component), and the content of (b-2) component is 20% by weight or more relative to the total amount of (b-1) component and (b-2) component.
Examples of the organic yellow pigment include c.i. pigment yellow 24, 120, 138, 139, 151, 175, 180, 185, 181, 192, 193, and 194. Examples of the organic orange pigment include c.i. pigment orange 13, 36, 43, 60, 61, 62, 64, 71, 72. Examples of the organic red pigment include c.i. pigment red 122, 123, 149, 178, 177, 179, 180, 189, 190, 202, 209, 254, 255, 264. Examples of the organic blue pigment include c.i. pigment blue 15 and 15: 1. 15: 2. 15: 3. 15: 6. 16, 25, 56, 57, 60, 61, 64, 65, 66, 75, 79, 80. Examples of the organic violet pigment include c.i. pigment violet 19, 23, 29, 32, and 37.
Among the above components belonging to the component (b), the component (b) contained in the pixel-dividing layer in the organic EL display device of the present invention preferably contains an organic black pigment, and the organic black pigment contains a compound represented by the formula (5) or the formula (6) and/or an isomer thereof, from the viewpoint of reducing luminance unevenness. The component (b) contained in the pixel-dividing layer more preferably contains a compound represented by formula (7) or an isomer thereof. The compounds represented by the formulas (5) to (7) can be synthesized by reacting 2, 5-dihydroxy-1, 4-benzenediacetic acid with isatin or a derivative thereof in the presence of an acidic catalyst, and then colored.
[ chemical formula 3]
[ chemical formula 4]
In the formula (5) and the formula (6), R 22 1 ~R 31 10 Each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
[ chemical formula 5]
The component (b) may be a component obtained by subjecting the component (b) to a pulverization treatment by a known method such as a solvent salt pulverization method or an acid paste method, in view of further suppressing the uneven brightness. When the benzodifuranone-based black pigment is miniaturized, the compound represented by the formula (8) or a salt thereof is allowed to coexist and adsorbed on the pigment surface, whereby uneven brightness may be easily suppressed.
[ chemical formula 6]
In the formula (8), n and m represent integers, and each independently represents 0 to 2.
Wherein n+m is more than or equal to 1.
In the case where the component (b) contains a benzodifuranone-based black pigment, it is preferable that the pigment has a coating layer containing silica on its surface in order to improve the developability and suppress development residues at the opening. The silica contained in the coating layer herein is not the component (a) described above, but forms part of the component (b).
The content of the component (b) is preferably 1% by weight or more, more preferably 10% by weight or more, in the pixel-dividing layer, from the viewpoint of exhibiting high light-shielding properties. In view of reducing uneven brightness, it is preferably 50% by weight or less, more preferably 30% by weight or less.
In addition, when the component (a) is contained in addition to the component (b), the content of the component (a) is SiO based on 100 parts by weight of the component (b) in terms of reducing the uneven brightness 2 The amount is preferably 20 to 70 parts by weight, more preferably 30 to 50 parts by weight in terms of the amount. That is, in the organic EL display device of the present invention, the content of the component (a) relative to the component (b) in the pixel-dividing layer is represented by SiO 2 The amount of the components is preferably 20 to 70 parts by weight.
(E) lyophobic Material
When the organic EL layer is formed by the inkjet method, the photosensitive resin composition used in the present invention preferably contains a lyophobic material. As the lyophobic material, a known material such as a fluorine-based polymer or a fluorine-containing compound having a silane compound is used, and a lyophobic material having at least an amide group or a urethane group is preferable. The presence of an amide group or a urethane group improves the compatibility with the alkali-soluble resin (a), and has the effect of reducing defects such as shrinkage cavity and improving uniformity of the film thickness of the cured film, thereby reducing display defects in the display device.
Examples of the lyophobic material include 2- (perfluorobutyl) ethyl (meth) acrylate, 2- (perfluorohexyl) ethyl (meth) acrylate, and commercially available "Megaface (registered trademark)" RS-72-K, RS-72-A, RS-75, RS-76-E, RS-76-NS, RS-78, and RS-90 (DIC).
Preferable examples of the epoxy group-containing (meth) acrylate monomer include glycidyl acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether (4-HBAGE), 4-hydroxybutyl methacrylate glycidyl ether, an acrylate having an alicyclic epoxy group, and a methacrylate having an alicyclic epoxy group.
The lyophobic material (E) having an amide group or a urethane group may be a copolymer obtained by copolymerizing a (meth) acrylic monomer substituted with a different functional group. By copolymerizing different functional groups substituted for the (meth) acrylic monomer, balance of lyophobicity and solubility can be easily obtained. Examples thereof include hydroxyl group-containing (meth) acrylates, hydroxyl group-containing (meth) acrylamides, alkoxy group-containing (meth) acrylates, blocked isocyanate group-containing (meth) acrylates, phenoxy group-containing (meth) acrylates, alkyl (meth) acrylates, vinyl group-containing compounds, and the like. Examples of the hydroxyl group-containing (meth) acrylic acid esters include 2-hydroxyethyl (meth) acrylate and the like. Examples of the hydroxyl group-containing (meth) acrylamides include N-methylolacrylamide. Examples of the (meth) acrylic acid ester having an alkoxy group include 3-methacryloxypropyl methyl dimethoxy silane. Examples of the blocked isocyanate group-containing (meth) acrylate include 2- (0- [1' -methylpropyleneamino ] carboxyamino) ethyl methacrylate (Karenz MOI-BM: manufactured by Showa electric Co., ltd.; registered trademark) and the like. Examples of the phenoxy group-containing (meth) acrylic acid esters include 2-phenoxybenzyl acrylate and 3-phenoxybenzyl acrylate. The alkyl (meth) acrylate is a diluted monomer of an unsubstituted or substituted alkyl (meth) acrylate having an alkyl group having 1 to 12 carbon atoms, which is unsubstituted or may be substituted with at least one of an amino group, a monoalkylamino group, a dialkylamino group, a hydrocarbon aromatic ring, and a heterocyclic ring, or an acid anhydride is cleaved and added to a hydroxyl group, and examples thereof include alkyl acrylates. Examples of the vinyl-containing compound include n-butyl vinyl ether.
The compound contained in the lyophobic material (E) having an amide group or a urethane group is usually a (co) polymer. The (co) polymer as the compound contained in the lyophobic material (E) can be obtained by a known polymerization method. The (co) polymer can be obtained by ionic polymerization such as radical polymerization, anionic polymerization, and the like. The polymer may be any of random copolymer, block copolymer and graft (co) polymer, and may be an alternating copolymer. Here, a free radical (co) polymerization method is exemplified. The lyophobic material (E) can be obtained by randomly copolymerizing a predetermined amount of dimethyl (meth) acrylamide, a predetermined amount of fluorine-containing (meth) acrylate monomer, and a predetermined amount of epoxy-containing (meth) acrylate, hydroxyl-containing (meth) acrylamide, alkoxy-containing (meth) acrylate, blocked isocyanate-containing (meth) acrylate, phenoxy-containing (meth) acrylate, alkyl (meth) acrylate, vinyl-containing compound, as required, with a radical polymerization initiator in an appropriate solvent. In the random copolymerization, a chain transfer agent may be added as needed. As the radical polymerization initiator, for example, tert-butyl peroxy-2-ethylhexanoate can be used. As the chain transfer agent, for example, dodecyl mercaptan may be used. As the solvent, for example, an inert solvent such as cyclohexanone may be used.
The weight average molecular weight of the lyophobic material (E) having an amide group or a urethane group is preferably in the range of 1500 to 50000. By setting the molecular weight to be within this range, the resin composition can be more easily dissolved in a solvent used for the photosensitive resin composition. Further, a molecular weight in this range is preferable because the defoaming property of the photosensitive resin composition solution is improved. From the viewpoint that the obtained cured film is likely to exhibit sufficient liquid repellency, the liquid repellent material (E) having an amide group or a urethane group is preferably 0.1 part by weight or more, more preferably 0.3 part by weight or more, based on 100 parts by weight of the alkali-soluble resin (a). In addition, from the viewpoint of not easily generating liquid repellency in the pixel and easily obtaining high durability, it is preferably 10 parts by weight or less, more preferably 5 parts by weight or less.
Spacer >
In the organic EL display device of the present invention, the spacers 4 are provided on the pixel dividing layer. As a first object, by providing the spacers, the contact area between the substrate and the vapor deposition mask when the organic EL layer is formed can be reduced, and thus, particle generation during the process can be suppressed. As a result, the yield of the panel can be reduced and the deterioration of the light emitting element can be suppressed. As a second object, as described above, it is necessary to form spacers on the pixel dividing layer in order to support the structure to be covered on the second electrode in the subsequent step and to secure the strength of the display device. The spacers must be patterned in the same manner as the pixel dividing layers, and the residues in the removed portions may cause defects such as short circuits and black spots. Further, the shape of the edge of the spacer may cause the second electrode to break, and thus workability such as gentle forward taper is also required.
The spacer is not particularly limited as long as it is a material having desired mechanical and electrical properties, and is not limited to any of known organic and inorganic substances, and is preferably a cured film of a photosensitive resin composition in view of processability. In addition, by forming the same material as the pixel dividing layer by one-step processing, the yield of the panel can be improved and the cost can be reduced, with the process time reduced.
As described above, the problem of separation of the pixel dividing layer and the organic EL layer is also the same problem at the interface where the spacer and the organic EL layer are in contact, and therefore, in the present invention, when the maximum value of the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is set to Ramax, ramax is 1.0nm to 50 nm. Further, the surface roughness (Ra 2) of the spacer is more preferably Ramax. In addition, both the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer may be Ramax. The surface roughness of the spacer may be measured by an Atomic Force Microscope (AFM) in the same manner as the pixel dividing layer.
Further, since the spacers are formed on the outermost surface of the substrate, the surfaces of the spacers become interfaces with the organic EL layer. Conventionally, since the adhesion between the spacer and the organic EL layer is poor, peeling is likely to occur, and particularly, it is a great problem in flexible products. In the present invention, the anchoring effect can be obtained by setting the surface roughness (Ra 2) of the spacer to 1.0nm or more, and the adhesion to the organic EL layer can be improved by setting the surface roughness to preferably 5.0nm or more, more preferably 20nm or more. In addition, if the surface roughness (Ra 2) of the spacer is 1.0nm or more, the anchor effect can be obtained, and it is preferably 50nm or less for the purpose of suppressing pinholes in the second electrode and defects in a sealing process described later. In the case where the adhesion is improved by a large Ra2, it is effective to ensure that the interface between the spacer and the organic EL layer is as large as possible, and in the case where Ra2 is larger than the surface roughness Ra1 of the pixel dividing layer, that is, ra2 is Ramax, the area of the interface between the substrate and the organic EL layer is preferably 50% or more of the area of the interface between the spacer and the organic EL layer. This means that the spacer is 50% or more of the surface area of the substrate.
When Ra1 and Ra2 are larger than 1.0nm, in addition to the effect of improving the adhesion, it is possible to suppress the reflection of external light of the display device by increasing the diffuse reflection light of the substrate. In general, when external light is incident on a substrate, both specular reflection light and diffuse reflection light are generated on the surface of the substrate, and the total amount of the two reflection light is the amount of reflection light, but when a person recognizes that the person is dazzling or reflecting, the influence of the specular reflection light is large. That is, in order to ensure the display quality of the display device, it is effective to increase the diffuse reflection light of the substrate and reduce the specular reflection light. That is, by making the surface roughness Ra1 and Ra2 of the pixel dividing layer and the spacers included on the surface of the substrate larger than 1.0nm, the diffuse reflected light on the surface of the substrate increases, and as a result, the display quality of the display device is ensured.
Further, when the absolute value of the difference between Ra1 and Ra2 is 1.0nm or more, two anchoring effects are obtained, and the adhesion is improved, which is more preferable.
In addition, the shape of the edge of the spacer may cause the second electrode to break, and therefore, a gentle positive taper is preferable. Here, the positive taper means: an angle formed by a tangent line at an interface of the pixel dividing layer and the spacer and a tangent line at a position of 50% film thickness of a maximum thickness of the spacer in a surface of the tapered portion of the spacer is less than 90 degrees.
The thickness of the spacer is usually 0.3 μm to 10 μm, and is not particularly limited as long as it is sufficient to contact the vapor deposition mask and support the structure covering the second electrode.
< organic EL layer >)
In the organic EL display device of the present invention, the structure of the organic EL layer 5 is not particularly limited, and may be any of (1) a hole transport layer/light emitting layer, (2) a hole transport layer/light emitting layer/electron transport layer, and (3) a light emitting layer/electron transport layer, for example. The above-described configuration may be a plurality of stacked layers with the charge generation layer interposed therebetween. The charge generation layer, which is also commonly referred to as an electron extraction layer, a connection layer, an intermediate electrode, an intermediate conductive layer, an intermediate insulating layer, may be formed using a known material. The tandem type is preferable because the emission luminance and the emission lifetime can be expected to be improved. Specific examples of the tandem type include a stacked structure including a charge generation layer between an anode and a cathode, such as (4) a hole transport layer/light emitting layer/electron transport layer/charge generation layer/hole transport layer/light emitting layer/electron transport layer, (5) a hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/charge generation layer/hole injection layer/hole transport layer/light emitting layer/electron transport layer/light emitting layer/charge generation layer/electron transport layer/light emitting layer/electron transport layer.
Each of the layers may be a single layer or a plurality of layers, or may be doped. In particular, the electron transport layer and the charge generation layer are preferably metal doped layers doped with metal, and thus the electron transport ability and the ability to inject electrons into other adjacent layers can be improved. In addition to the above layers, a protective layer (cover layer) may be provided, so that the light emission efficiency can be further improved by the optical interference effect. The thickness of each layer is usually selected from 1 to 200nm in consideration of the influence on the resistance value of each layer material and the extraction efficiency of EL light emission.
< hole transport layer >)
The hole transport layer is formed, for example, by a method of laminating or mixing one or more hole transport materials, or a method of using a mixture of a hole transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride may be added to the hole transport material to form a hole transport layer. The hole transporting material is not particularly limited as long as it can form a thin film necessary for manufacturing a light emitting element, and can inject holes from an electrode serving as an anode and further transport holes. The hole transport layer may be a single layer or may be formed by stacking a plurality of layers.
Preferable examples of the hole transporting material include triphenylamine derivatives such as 4,4' -bis (N- (3-methylphenyl) -N-phenylamino) biphenyl, 4' -bis (N- (1-naphthyl) -N-phenylamino) biphenyl, 4',4″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, biscarbazole derivatives such as bis (N-allylcarbazole) and bis (N-alkylcarbazole), pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives, and other heterocyclic compounds having the aforementioned monomers in the side chain in the polymer system, polycarbonates, styrene derivatives, polythiophenes, polyanilines, polyfluorenes, polyvinylcarbazole, polysilanes, and the like.
< luminescent layer >)
In the light-emitting layer, the injected electrons recombine with holes to emit light. The ability to perform various types of multicolor light emission by selecting the materials constituting the light-emitting layer is a major feature of organic EL display devices.
The light-emitting layer is a layer that emits light by excitation of a light-emitting material by recombination energy generated by collision of holes with electrons. The light-emitting layer may be a single layer or may be formed by stacking a plurality of layers, and each layer may be formed of a light-emitting material (host material and/or dopant material). Each light-emitting layer may be composed of only one of the host material and the dopant material, or may be composed of a combination of 1 or more host materials and 1 or more dopant materials, respectively. That is, in each light-emitting layer, only the host material or the dopant may emit light, or both the host material and the dopant may emit light. The light-emitting layer is preferably composed of a combination of a host material and a dopant material, from the viewpoint of efficiently utilizing electric energy and obtaining light emission of high color purity. The dopant material may be included in the bulk of the host material or may be included in a portion of the host material.
From the viewpoint of suppressing the concentration extinction phenomenon, the content of the dopant material in the light-emitting layer is preferably 30 parts by weight or less, more preferably 20 parts by weight or less, relative to 100 parts by weight of the host material.
The light emitting layer may be formed by: for example, a method of co-evaporating a host material and a dopant material; a method of vapor deposition after mixing a host material and a dopant material in advance; etc.
Examples of the host material constituting the light-emitting material include naphthalene, anthracene, phenanthrene, pyrene, and the like,And compounds having a condensed aromatic ring such as tetracene, triphenylene, perylene, fluoranthene, fluorene, and indene. Two or more of them may be used. Three as light emitting layersThe host material used for linear light emission (phosphorescence) is preferably a metal chelate hydroxyquinoline (oxinoid) compound, a dibenzofuran derivative, a dibenzothiophene derivative, a carbazole derivative, an indolocarbazole derivative, a triazine derivative, a triphenylene derivative, or the like. Among them, compounds having an anthracene skeleton or a pyrene skeleton are more preferable because high-efficiency light emission is easily obtained.
Examples of the dopant material constituting the light-emitting material include condensed ring derivatives such as anthracene and pyrene; metal complex compounds such as tris (8-hydroxyquinoline) aluminum; bisstyryl derivatives such as bisstyryl anthracene derivatives and distyryl benzene derivatives; tetraphenylbutadiene derivatives; dibenzofuran derivatives; carbazole derivatives; indolocarbazole derivatives; a polyphenylene ethylene derivative; etc. The dopant material used for triplet emission (phosphorescence) of the light-emitting layer is preferably a metal complex compound containing at least one metal selected from the group consisting of iridium (Ir), ruthenium (Ru), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re). The ligand constituting the metal complex compound may be appropriately selected depending on the desired emission color, the performance of the organic EL display device, and the relationship with the host compound, and is preferably a nitrogen-containing aromatic heterocycle having a phenylpyridine skeleton, a phenylquinoline skeleton, a carbene skeleton, or the like. Specifically, tris (2-phenylpyridyl) iridium complex, bis (2-phenylpyridyl) (acetylacetonate) iridium complex, tetraethylporphyrin platinum complex, and the like can be mentioned. Two or more of them may be used.
< Electron transport layer >)
The electron transport layer is a layer that transports electrons injected from the cathode to the light emitting layer. In order to achieve a low driving voltage, the organic EL layer of the present invention preferably also contains an electron transport layer. The electron transport layer is expected to have high electron injection efficiency and to efficiently transport the injected electrons. Therefore, the electron transport layer is preferably the following: the electron affinity and electron mobility are high, and the stability is excellent, and impurities which become traps (trap) are not easily generated during manufacturing and use. Particularly, when the film thickness is large, the low molecular weight compound is easily crystallized and the like, and thus the film quality is deteriorated, and therefore, the compound having a molecular weight of 400 or more is preferable. In view of the balance between the transport of holes and electrons, it is preferable that the electron transport layer has an effect of preventing the flow of unbound holes from the anode to the cathode, and the electron transport layer of the present invention includes a hole blocking layer that can prevent the movement of holes in a similar manner. The electron transport layer may be a single layer or a stack of layers.
Examples of the electron transport material constituting the electron transport layer include fused polycyclic aromatic derivatives such as naphthalene and anthracene. Two or more of them may be used. Among these, compounds having a heteroaromatic ring structure containing electron-accepting nitrogen are preferred from the viewpoint of further reducing the driving voltage and obtaining high-efficiency light emission.
The electron accepting nitrogen referred to herein means a nitrogen atom forming multiple bonds between adjacent atoms. Since the nitrogen atom has high electronegativity, the multiple bond has a property of accepting electrons. Therefore, the aromatic heterocycle containing an electron accepting nitrogen has high electron affinity. The electron transporting material having electron accepting nitrogen easily accepts electrons from the cathode having high electron affinity, and thus can further reduce the driving voltage. In addition, the supply of electrons to the light-emitting layer increases, and the recombination probability increases, so that the light-emitting efficiency increases.
Examples of the heteroaromatic ring containing an electron-accepting nitrogen include a triazine ring and a pyridine ring. As the compound having such a heteroaromatic ring structure, triazole derivatives such as N-naphthyl-2, 5-diphenyl-1, 3, 4-triazole, bipyridine derivatives such as 2, 5-bis (6 ' - (2 ',2 "-bipyridyl)) -1, 1-dimethyl-3, 4-diphenylsilole, and bipyridine derivatives such as 1, 3-bis (4 ' - (2, 2':6'2" -bipyridyl)) benzene may be preferably used from the viewpoint of electron transport ability. Two or more of them may be used.
Further, as a substance satisfying the conditions required for the electron transport layer, a compound having a phenanthroline (phenanthrine) skeleton can be mentioned. In order to obtain stable luminescence over a long period of time, a material excellent in thermal stability and film formation is desired, and among the compounds having a phenanthroline skeleton, a compound having a three-dimensional structure of a substituent itself, or a three-dimensional structure by steric repulsion with the phenanthroline skeleton or steric repulsion with an adjacent substituent, or a compound having a plurality of phenanthroline skeletons linked is preferable. In the case of linking a plurality of phenanthroline skeletons, a compound including a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, and a substituted or unsubstituted aromatic heterocyclic ring in the linking unit is more preferable.
The electron-transporting material is not limited to one compound having a phenanthroline skeleton, and a plurality of the above-described compounds may be used in combination, or one or more known electron-transporting materials may be used in combination with the above-described compounds. The known electron transport material is not particularly limited, and examples thereof include quinolinol derivative metal complexes typified by 8-hydroxyquinolinylaluminum, benzoquinolinol metal complexes, tropone metal complexes, flavonol metal complexes, perylene derivatives, pyrenone derivatives, naphthalene, coumarin derivatives, oxadiazole derivatives, aldazin derivatives, bisstyryl derivatives, pyrazine derivatives, phenanthroline derivatives, quinoline derivatives, benzimidazole derivatives, triazole derivatives, quinoxaline derivatives, benzoquinoline derivatives, and the like. These electron transport materials may be used alone or in combination with different electron transport materials. In addition, a compound having a nitrogen-containing aromatic heterocycle such as a phenanthroline derivative or an oligopyridine derivative may be used. In particular, a compound having a phenanthroline skeleton described later is preferable because it exhibits excellent electron transport ability.
The electron transport material may be used alone, or 2 or more of the electron transport materials may be mixed, or 1 or more of the electron transport materials may be mixed with the electron transport material. In addition, the electron transport layer in the present invention preferably contains a donor-type doping material. The donor-type dopant is a compound that improves the electron injection barrier, thereby facilitating electron injection from the cathode or the electron injection layer to the electron transport layer and further improving the conductivity of the electron transport layer. In the present invention, the donor-type dopant preferably contains 1 or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, inorganic salts of the metals, and complexes of the metals and organic substances. The donor-type dopant is preferably an inorganic salt or a complex with an organic substance, compared to a metal simple substance, in view of easy vapor deposition in vacuum and excellent handling, and is more preferably a complex with an organic substance in view of easy handling in the atmosphere and easy adjustment of the concentration to be added.
< Charge generation layer >)
The charge generation layer generally includes a bilayer, and specifically, a pn junction type charge generation layer including an n-type charge generation layer and a p-type charge generation layer can be used. The pn junction type charge generation layer generates charges by applying a voltage to the organic EL layer, or separates the charges into holes and electrons, which are injected into the light emitting layer through the hole transport layer and the electron transport layer. Specifically, the plurality of light-emitting layers included in the organic EL layer function as an intermediate charge generation layer. The n-type charge generation layer supplies electrons to the light emitting layer present on the anode side, and the p-type charge generation layer supplies holes to the light emitting layer present on the cathode side. Therefore, the light-emitting luminance and the light-emitting efficiency of the organic EL layer including the plurality of light-emitting layers can be further improved, the driving voltage can be reduced, and the light-emitting lifetime of the organic EL layer can be further improved. For this reason, in the present invention, the organic EL layer preferably contains a charge generation layer. In the present invention, as described later, the charge generation layer preferably contains a donor-type dopant material, and the donor-type dopant material preferably contains 1 or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, inorganic salts of the metals, and complexes of the metals and organic substances.
The n-type charge generation layer preferably includes an n-type dopant material and a host material, and known materials can be used for these. For example, an alkali metal, an alkaline earth metal, or a rare earth metal can be used as the n-type dopant. As the host material, a compound having a nitrogen-containing aromatic heterocycle such as a compound having a phenanthroline skeleton or an oligopyridine derivative can be used. In particular, a compound having a phenanthroline skeleton, which will be described later, is preferable because it exhibits excellent properties as a host material for the n-type charge generation layer, and it is possible to use a combination of these compounds.
The p-type charge generation layer preferably includes a p-type dopant material and a host material, and known materials can be used for these. For example, as the p-type dopant material, there may be used tetrafluorene-7, 8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivative, decene derivative, iodine, feCl 3 、FeF 3 、SbCl 5 Etc. As the p-type doping material, an axial derivative is preferable. As the host material, an arylamine derivative is preferable.
< Compound having phenanthroline skeleton >)
In the present invention, the electron transport layer and/or the charge generation layer preferably contains a compound having a phenanthroline skeleton represented by the following general formula (1).
[ chemical formula 7]
Here, R is 1 ~R 8 Each of which may be the same or different, is selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, and a heterocyclic group. Wherein R is 1 、R 3 、R 6 、R 8 At least one of them is selected from adamantyl, norbornyl, phenylvinyl, beta-naphthyl, phenanthryl, pyrenyl.
In the present invention, the electron transport layer and/or the charge generation layer more preferably contains a compound having a phenanthroline skeleton represented by the following general formula (2).
[ chemical formula 8]
Here, R is 9 ~R 16 Each of which may be the same or different from the hydrogen sourceSon, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, X 1 Is selected from the group consisting of a plurality of combinations of the above. Wherein R is 9 ~R 16 At least one of them is X 1 . n represents a natural number of 2 to 6. X is X 1 The coupling unit is a single bond or an n-valent coupling unit derived from any one of benzene, anthracene, pyridine, ethylene, thiophene, furan, methylene (methyl), carbazole, cyclohexane, spirobifluorene, triphenylamine, triptycene, and a structure formed by combining the above compounds, and is used for coupling a plurality of phenanthroline skeletons.
Among these substituents, alkyl represents a saturated aliphatic hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc., and may or may not have a substituent. The additional substituent in the case of substitution is not particularly limited, and examples thereof include an alkyl group, a halogen group, an aryl group, a heteroaryl group, and the like, and this is also common in the following description. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 to 20, more preferably 1 to 8, from the viewpoints of easiness of obtaining and cost. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, or an adamantyl group, and may or may not have a substituent. The number of carbon atoms of the alkyl moiety is not particularly limited, and is preferably in the range of 3 to 20. The aralkyl group represents an aromatic hydrocarbon group such as a benzyl group or a phenethyl group, which is an aliphatic hydrocarbon, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. In addition, alkenyl represents an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, etc., which may be unsubstituted or substituted. In addition, cycloalkenyl groups include unsaturated alicyclic hydrocarbon groups containing a double bond such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, and the like, which may be unsubstituted or substituted. The alkynyl group represents an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and may be unsubstituted or substituted. The alkoxy group represents an aliphatic hydrocarbon group having an ether bond, such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The alkylthio group is a group obtained by replacing an oxygen atom of an ether bond of an alkoxy group with a sulfur atom. Examples of the aryl ether group include an aromatic hydrocarbon group such as a phenoxy group, which may be unsubstituted or substituted with an ether bond. The arylthio ether group is a group in which an oxygen atom of an ether bond of the arylthio ether group is replaced with a sulfur atom. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group, or the like, and may be unsubstituted or substituted. Examples of the heterocyclic group include aliphatic rings having an atom other than carbon in the ring, such as pyran ring, piperidine ring, and cyclic amide, and may or may not have a substituent. The number of carbon atoms of the heterocyclic group is not particularly limited, and is preferably in the range of 2 to 20. Halogen represents fluorine, chlorine, bromine or iodine. The haloalkane, haloalkene, and haloalkyne are, for example, trifluoromethyl and the like, and represent groups in which a part or all of the alkyl group, alkenyl group, or alkynyl group is substituted with halogen, and the remaining part may be unsubstituted or substituted. The aldehyde group, carbonyl group, ester group, carbamoyl group, amino group may include a group substituted with an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic ring, or the like, and the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic ring may be unsubstituted or substituted. Silyl represents a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The siloxane group means a silicon compound group via an ether bond, such as a trimethylsiloxane group, which may be unsubstituted or substituted. In addition, a ring structure may be formed between adjacent substituents. The ring structure formed may be unsubstituted or substituted.
In addition, the substituent itself has a three-dimensional structure or forms a three-dimensional structure by steric repulsion with the phenanthroline skeleton or an adjacent substituent, and thus the compound containing the phenanthroline skeleton has low planarity, is less likely to be crystallized, and can maintain a good amorphous thin film state. The substituent itself has a three-dimensional structure, for example, a three-dimensional structure such as t-butyl, adamantyl, or norbornyl, and a bulky three-dimensional structure other than a two-dimensional planar structure, and may be unsubstituted or substituted. The substituent that forms a three-dimensional structure by steric repulsion with the phenanthroline skeleton or an adjacent substituent means that the substituent plane is in a plane different from the plane of the phenanthroline skeleton by steric repulsion between the substituent and the phenanthroline skeleton or between the substituent and an adjacent substituent although the substituent itself has a planar structure. These conditions can be examined using molecular modeling, computational chemistry, and the like.
In addition, by connecting a plurality of phenanthroline skeletons, the compound containing the phenanthroline skeletons is increased in molecular weight, and crystallization is not likely to occur even when the glass transition temperature is increased, so that a good amorphous thin film state can be maintained.
In the compound having a phenanthroline skeleton of the general formula (1) in the present invention, it is further preferable to introduce substituents at positions 2, 4, 7 and 9 of the phenanthroline skeleton. These substituents are the same as those described above. The compound having a phenanthroline skeleton is specifically, but not limited to, the following structure.
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
The host material of the electron transport layer and/or the charge generation layer is not requiredThe compound having a phenanthroline skeleton is limited to one, and a plurality of compounds having a phenanthroline skeleton may be used in combination, or one or more known host materials may be used in combination with a compound having a phenanthroline skeleton. The known host material is not particularly limited, and conventionally known anthracene, phenanthrene, pyrene, perylene, and the like can be used,Such as fused ring derivatives, metal complexes of quinolinol derivatives represented by tris (8-hydroxyquinoline) aluminum, benzoxazole derivatives, stilbene derivatives, benzothiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, oxadiazole derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyryl benzene derivatives, metal complexes of quinolinol derivatives combined with different ligands, oxadiazole derivative metal complexes, benzoxazole derivative metal complexes, coumarin derivatives, pyrrolopyridine derivatives, pyrenone derivatives, thiadiazole pyridine derivatives, and polyphenylene derivatives, polyparaphenylene derivatives and polythiophene derivatives in a polymer system.
In addition, although a compound having a phenanthroline skeleton can be used as a dopant material, it is preferable to use the compound as a host material because it has excellent electron transport ability.
< second electrode >)
In the present invention, the second electrode 6 needs to be a light-reflective electrode in the case of a bottom emission type, and needs to be a light-transmissive electrode in the case of a top emission type.
In the case of the bottom emission type, a material exhibiting high visible light reflectance and low electric resistance at a film thickness of a predetermined film or more is preferable, and Ag or an Ag alloy film mainly containing Ag is useful because it has high reflectance. As the Ag alloy film, mgAg alloy containing Ag as a main component, or the like can be used. Al or an Al alloy film containing Al as a main body is also preferable as the second electrode for bottom emission. The Cr-containing AlCr alloy film and the Ni-containing AlNi alloy film are preferable because they have a high reflectance equivalent to that of pure Al and can realize low resistance.
In the case of the top emission type, for example, a transparent conductive metal oxide such as tin oxide, indium oxide, or Indium Tin Oxide (ITO) may be used, and a thin film of MgAg alloy which can be produced by vapor deposition is also preferable in order to avoid damage to the organic EL layer.
The resistance of the second electrode is not limited as long as it can supply a sufficient current to the light emission of the light emitting element, and is preferably low in terms of power consumption of the light emitting element. The thickness of the electrode may be arbitrarily selected according to characteristics such as transmittance and resistance, and may be used between 100 and 300nm in the case of a bottom emission type or between 10 and 30nm in the case of a top emission type.
< wiring, TFT >
In the present invention, as described above, a wiring, a TFT7, and other driving circuits may be provided as components included in the substrate 1.
In the case where the organic EL display device is of an active-drive top emission type, the island-shaped first electrode 2 patterned is often connected to the TFT7 formed in advance as a part of the substrate 1.
Examples of the semiconductor layer of the TFT include a-Si (amorphous silicon), p-Si (polycrystalline silicon), microcrystalline silicon, an oxide typified by In-Ga-Zn-O, LTPO (Low Temperature Polycrystalline Oxide, low-temperature polycrystalline oxide) In which p-Si and an oxide are used together, and both a-Si TFT and p-Si TFT are generally used. The a-si tft has low mobility as an index indicating the ease of movement of electrons, and can be manufactured on a large substrate even with a relatively short manufacturing process, and thus can be widely used for small to large displays. On the other hand, the p-si tft has high mobility, and a driver circuit and the like can be formed on a substrate. The manufacturing process is longer than a-Si, and the manufacturing difficulty is high on a large substrate, so that it is preferable to be mainly used for small and medium-sized displays. In particular, p-Si in a p-SiTFT can be usually formed by irradiating a laser beam with a-Si as a starting film, and then immediately melting and crystallizing the film. In addition, there is a step of doping phosphorus or boron into Si, which is not used in the manufacturing step of the a-Si TFT, and the threshold value of the TFT characteristics can be controlled by doping impurities into the Si film.
The TFTs are roughly classified into bottom gate type and top gate type in terms of their structure. The a-SiTFT is preferably bottom gate type and the p-SiTFT is preferably top gate type. For example, in the case of a top gate type, the semiconductor layer is connected to the drain electrode and the source electrode, and a gate electrode is provided above the semiconductor layer. The TFT is formed on the substrate by repeating the essential steps of thin film formation, patterning, etching, and cleaning several times. The method of forming the TFT may use a known method. In addition, in the case of the bottom gate type, the gate electrode is arranged at the lowermost layer, a semiconductor layer/insulating film is provided at the upper layer, and a source electrode and a drain electrode are formed at the upper layer. The gate electrode may be connected to the source electrode and the drain electrode by a straight line to form an inverted triangle, which is also called an "inverted staggered structure".
< planarization layer >)
In particular, in the case where wiring and TFT7 are provided in the substrate 1 as shown in fig. 2, for example, the planarizing layer 8 is preferably used. By providing the planarizing layer 8, the wiring and the irregularities of the TFT7 can be covered and planarized. In this case, since the first electrode 2 is provided on the planarizing layer, it is preferable that the first electrode 2 is connected to the wiring and the TFT7 through a contact hole formed in the planarizing layer 8. The planarizing layer 8 is not limited to any of known organic or inorganic materials, and is preferably a cured film containing a photosensitive resin composition from the viewpoint of processability. The planarizing layer 8 can be coated by, for example, a spin coating method, a slit coating method, a dip coating method, a spray coating method, or a printing method, for example, because a thin film can be uniformly formed on a large substrate.
The photosensitive resin composition preferably contains (a) an alkali-soluble resin, (B) a photosensitive agent, and (C) an organic solvent, and may further contain (D) a coloring material. As the photosensitive resin composition, a combination containing (a) an alkali-soluble resin and (B) a photosensitive agent enables pattern processing using photosensitivity. In addition, by containing the organic solvent (C), a state of varnish can be formed, and coatability may be improved. Further, by containing the coloring material (D) in the photosensitive resin composition, the planarizing layer can be blackened. The photosensitive resin composition may further contain other components.
Examples of the material of the alkali-soluble resin (a) include acrylic resins, epoxy resins, polyamide resins, silicone resins, precursors of these resins, and the like, and the film thickness is not particularly limited as long as it is sufficient to cover the irregularities. In the case where coloring is required from the viewpoints of light shielding and reflection prevention, a coloring material is preferably contained appropriately.
< sealing layer >)
After the second electrode is formed, it is preferably sealed by a sealing layer 9, for example, as shown in fig. 5. This is because the light-emitting element of the organic EL has poor resistance to oxygen and moisture, and it is preferable to seal the light-emitting element in an atmosphere in which oxygen and moisture are as little as possible in order to obtain a highly reliable display device. As for the member used for the sealing layer 9, a member having high gas barrier properties is preferably selected, and is appropriately selected from glass, a resin film, a gas barrier film, and the like, similarly to the substrate 1. For example, as an example of the gas barrier film, siO may be mentioned 2 (silicon oxide), siN (silicon nitride), siON (silicon oxynitride) and the like. In addition, siO may be used 2 A sealing layer 9 made of a resin material such as an acrylic resin or a silicone resin is provided on a layer made of a material such as (silicon oxide), siN (silicon nitride) or SiON (silicon oxynitride). In the case of a top emission type display device, it is preferable to form the display device from a light-transmitting material.
In addition, among adhesives used in the case where adhesion is required, a material having high gas barrier properties is also required, and may be selected from conventionally known materials such as a two-liquid epoxy adhesive (XNR, manufactured by Nagase ChemteX (inc.), a sealing material for organic devices (MOISTURE CUT, manufactured by MORESCO), and the like, or may be a method of melting sintered glass in the peripheral portion of the display device by laser.
In addition, in consideration of moisture, it is also effective to introduce a desiccant in the sealing step. As the drying agent, barium oxide, calcium oxide, and the like are known, and are not particularly limited as long as the adsorption performance of moisture is high.
< polarizing layer >)
For example, as shown in fig. 5, the organic EL display device of the present invention preferably further has a polarizing layer 10. Specifically, the linearly polarized layer and the λ/4 retardation layer are laminated to suppress reflection of light incident on the display device from the outside. The linearly polarized layer is not particularly limited, and for example, a film obtained by dyeing a polyvinyl alcohol film with iodine and uniaxially stretching the film is often used. The material constituting the λ/4 phase difference layer is not particularly limited, and polyimide-based resins having heat resistance and the like are preferable.
< ultraviolet absorbing layer >)
For example, as shown in fig. 5, the organic EL display device of the present invention preferably has an ultraviolet absorbing layer 11. By providing the ultraviolet absorbing layer 11, deterioration of the substrate and the organic EL layer 5 due to ultraviolet light can be suppressed, and reliability of the display device can be improved. The ultraviolet absorbing layer 11 is preferably a layer that absorbs light having a wavelength of 320nm or less, more preferably a layer that absorbs light having a wavelength of 360nm or less, and even more preferably a layer that absorbs light having a wavelength of 420nm or less. However, since light having a wavelength of 420nm or more overlaps with the emission wavelength of blue for display, the ultraviolet absorbing layer 11 preferably has a high transmittance in a region having a wavelength of 420nm or more. This is particularly effective in the case of using the organic EL display device of the present invention outdoors.
The ultraviolet absorbing layer 11 preferably contains a polyimide resin, a polyamide resin, a polyamideimide resin, a polycarbonate resin, a polyester resin, a polyethersulfone resin, a polyarylate resin, a polyolefin resin, a polyethylene terephthalate resin, a polymethyl methacrylate resin, a polysulfone resin, a polyethylene resin, a polyvinyl chloride resin, an alicyclic olefin polymer resin, an acrylic polymer resin, a cellulose ester resin, or the like. They may be contained in 2 or more kinds thereof. Of these, polyimide resins and polyamide resins are more preferable.
The ultraviolet absorbing layer 11 layer may contain an ultraviolet absorber. Examples of the ultraviolet absorber include benzophenone-based compounds, oxybenzophenone-based compounds, benzotriazole-based compounds, salicylate-based compounds, acrylonitrile-based compounds, cyanoacrylate-based compounds, hindered amine-based compounds, triazine-based compounds, nickel complex salt-based compounds, ultrafine titanium oxide, metal complex salt-based compounds, and other known polymer ultraviolet absorbers. Two or more of them may be contained. The ultraviolet absorber is preferably a benzotriazole-based compound or a benzophenone-based compound, and more preferably a benzotriazole-based compound, from the viewpoint of excellent transparency.
Examples of the polymer ultraviolet absorber include ultraviolet absorbers obtained by copolymerizing a reactive ultraviolet absorber RUVA-93 manufactured by the chemical company of Otsuka and an acrylic monomer.
Method for manufacturing organic EL display device
The method for manufacturing an organic EL display device according to the present invention is a method for manufacturing an organic EL display device having a substrate, which has a first electrode 2, a pixel dividing layer 3, and a spacer 4 on a base material 1, and having a step of processing the pixel dividing layer 3 and the spacer 4 together, wherein a photomask used for the simultaneous processing is a halftone photomask having a light transmitting portion, a light shielding portion, and a semi-transmitting portion.
An example of a method of manufacturing an organic EL display device according to the present invention will be described with reference to the case of manufacturing the top emission type organic EL display device of fig. 5.
First, wirings and TFTs 7 are provided on a substrate as a resin film. As the step, a wiring for securing electrical connection is arranged in addition to the TFT forming step such as "gate electrode forming step", "gate insulating film forming step", "Si film forming step", "source electrode and drain electrode forming step", and the like, and can be formed by a known method.
Next, the planarizing layer 8 is coated by a slit coating method to form a film, and then cured by heating. At this time, a contact hole for connection with the first electrode 2 is provided in advance, and if the material used for the planarizing layer 8 is photosensitive, photolithography processing can be used for coping with the contact hole; if not photosensitive, conventional etching processes using the resist material as a mask can be used. In this way, the substrate 1 is completed.
Next, agPdCu and ITO were sequentially formed as first electrodes 2 on the substrate, and patterning was performed to form the first electrodes 2.
In the method for manufacturing an organic EL display device of the present invention, the pixel dividing layer 3 is formed in the void of the first electrode 2, and the spacer 4 is further formed on the pixel dividing layer. As a step, after a photosensitive resin is applied over the entire surface, an opening is formed in the first electrode by photolithography, and the opening is formed as a display pixel.
In the method for manufacturing an organic EL display device according to the present invention, the steps of forming the pixel division layer 3 and forming the spacers 4 on the pixel division layer are performed by a collective process, and the photomask for collectively processing the pixel division layer 3 and the spacers 4 needs to be a halftone photomask having a light transmitting portion, a light shielding portion, and a semi-transmitting portion. In general, when processing using photosensitivity is performed, a full-tone mask composed of a light shielding portion and a light transmitting portion is used, but the halftone mask used in the present invention means the following photomask: for example, as shown in fig. 6, a pattern including a light transmitting portion 12 and a light shielding portion 14 is provided, and a semi-transmissive portion 13 having a lower transmittance than the light transmitting portion 12 and a higher transmittance than the light shielding portion 14 is provided between the light transmitting portion 12 and the light shielding portion 14. By performing exposure using a halftone photomask, a pattern having a step shape can be formed after development and after heat curing. When the photosensitive resin composition is positive, the exposed portion irradiated with the active chemical rays through the light-transmitting portion is alkali-soluble and becomes an opening, and the unexposed portion not irradiated with the active chemical rays through the light-shielding portion becomes a thick film, which corresponds to the spacer 4, and the halftone exposed portion irradiated with the active chemical rays through the semi-transmitting portion corresponds to the pixel-divided layer 3 having a film thickness smaller than that of the spacer 4. Conversely, in the case where the photosensitive resin composition is negative, the cured portion irradiated with the active chemical rays through the light transmitting portion corresponds to the spacer 4, and the halftone exposed portion irradiated with the active chemical rays through the semi-transmissive portion corresponds to the pixel dividing layer 3.
As described later, as the halftone photomask used in the present invention, the transmittance of the semi-transmissive portion is preferably 15 to 50% of the transmittance of the transmissive portion. When the transmittance of the light transmitting portion is (% TFT), the transmittance (% THT) of the semi-light transmitting portion is preferably 15% or more, more preferably 20% or more. When the transmittance (% THT) of the semi-transparent portion is within the above range, the exposure amount at the time of forming the cured pattern having the step shape can be reduced, and thus the takt time can be shortened. On the other hand, the transmittance (% THT) of the semi-transmissive portion is preferably 50% or less, more preferably 45% or less. When the transmittance (% THT) of the semi-transparent portion is within the above range, the difference in film thickness between the spacer 4 and the pixel dividing layer 3 can be sufficiently increased, and the reliability of the display device can be improved. When the transmittance of the semi-transmissive portion is within the above range, a sufficient exposure amount of the active chemical rays is not obtained in the semi-transmissive portion during patterning of the photosensitive resin composition, and a difference occurs in the surface roughness of the pixel dividing layer 3 and the spacer 4 after the development step performed after the irradiation of the active chemical rays. In this way, by setting a difference in absolute value of the difference between the surface roughness Ra1 of the pixel dividing layer 3 and the surface roughness Ra2 of the spacer 4, two anchoring effects are obtained as described above, and improvement in adhesion is achieved. In order to effectively obtain the anchoring effect, the difference between Ra1 and Ra2 is also preferably ensured to be 1.0nm or more. In addition to the transmittance of the semi-transparent portion, ra1 and Ra2 can be adjusted by adjusting the resin composition including a coloring material, a lyophobic material, and the like in the photosensitive resin composition.
In addition to the above-described process using a halftone photomask, several methods such as mechanical polishing using an abrasive, shot blasting using an abrasive, wet blasting, plasma treatment, dry etching such as RIE, and the like can be combined to adjust the surface roughness, and in the present invention, the halftone photomask must be used so that the absolute value of the difference between Ra1 and Ra2 is 1.0nm or more.
In the method for manufacturing an organic EL display device of the present invention, a step of cleaning may be provided before the step of forming the organic EL layer 5, which will be described later. In general, contamination in a preceding step such as photolithography is often left on the surface of the first electrode, and therefore, wet cleaning and dry cleaning are effective. In the case of wet cleaning, an organic solvent, a surfactant, water, an acid solution, an alkali solution, or the like can be used, and selected from dipping, ultrasonic cleaning, boiling cleaning, and the like. In addition, in the case of dry cleaning, the cleaning may be selected from glow discharge treatment, plasma discharge treatment, UV/ozone treatment, and the like. In the case of dry cleaning in an oxygen atmosphere, the contamination can be removed and the work function can be adjusted. By adjusting the characteristics of the first electrode 2, the efficiency of carrier injection from the first electrode 2 into the adjacent organic EL layer 5 is increased, and as a result, the characteristics of the display device such as luminous efficiency and reliability are easily improved.
Next, the method for manufacturing an organic EL display device according to the present invention includes a step of forming the organic EL layer 5. The layers constituting the organic EL layer 5, such as a hole transport layer, a light emitting layer, and an electron transport layer, can be formed by a known method, for example, a mask vapor deposition method or an inkjet method.
The mask vapor deposition method is a method of patterning an organic compound by vapor deposition using a vapor deposition mask, and includes, for example, a method of vapor deposition in which a vapor deposition mask having a desired pattern as an opening is disposed on a vapor deposition source side of a substrate. In order to obtain a high-precision vapor deposition pattern, it is important to adhere a vapor deposition mask having high flatness to a substrate, and a technique of applying tension to the vapor deposition mask, a technique of adhering the vapor deposition mask to the substrate by a magnet disposed on the back surface of the substrate, or the like is generally employed. However, since the occurrence of particles due to the contact between the substrate and the vapor deposition mask may reduce the yield of the panel and deteriorate the light emitting element, it is preferable to make the spacers 4 in contact with the vapor deposition mask as small as possible.
Examples of the method for producing the vapor deposition mask include etching, mechanical polishing, sandblasting, sintering, laser processing, use of a photosensitive resin, and electroforming, and when a fine pattern is required, etching and electroforming methods excellent in processing accuracy are preferably employed.
In the mask vapor deposition method and the inkjet method, the finer the pattern is, the higher the difficulty is, and therefore, for example, it is required to use a light-emitting layer or the like for determining the light-emitting color at a minimum. In this case, for example, by sharing each color such as a hole transport layer and an electron transport layer other than the light-emitting layer, film formation is allowed on the entire surface, and thus, improvement in the yield of the panel and reduction in cost can be achieved.
The method for manufacturing an organic EL display device of the present invention further includes a step of forming the second electrode 6. The formation method may be a known method, and is preferably a vacuum deposition method because deterioration and damage of the organic El layer 5 serving as a substrate are easily avoided.
In the method of manufacturing the organic EL display device of fig. 5, after the step of forming the second electrode 6, the sealing layer 9, the polarizing layer 10, and the ultraviolet absorbing layer 11 are sequentially laminated. Each layer can be formed by a known method, and the organic EL display device of fig. 5 is completed in the above-described manner.
Examples
The present invention will be described below with reference to examples, but the present invention is not limited to these examples.
In the following evaluations, the number of tests n was not described, and the evaluation was performed with n=1.
Film thickness measurement of pixel dividing layer and spacer, taper observation >
The thicknesses of the pixel isolation layer and the spacer in each of the examples and the comparative examples were measured by using a surface roughness measuring machine (SURFCOM 1400D, manufactured by tokyo precision) based on the level difference between the pixel isolation layer and the spacer on the patterned substrate (100 mm×100 mm). In the case of the taper shape, a cross section obtained by cutting the patterned substrate was observed using a scanning electron microscope (SEM, manufactured by S-3000N,Hitachi High-Technologies).
Surface roughness of pixel dividing layer and spacer
The surface roughness of the pixel separation layer and the spacer in each of examples and comparative examples was observed on the pixel separation layer and the spacer of the patterned substrate (100 mm×100 mm) using an atomic force microscope (AFM, division Icon, bruker corporation), and in the results, an arithmetic average roughness (Ra) was used. As observation conditions, an RTESP-300 probe, a tapping mode, a scanning size of 5 μm ≡, a scanning rate of 0.1Hz, and the number of sampling lines of 1024 were set.
Observation of silica particles contained in the pixel-dividing layer
The silica particles contained in the pixel-divided layers in each of examples and comparative examples were measured using a transmission electron microscope-energy dispersive X-ray spectrometry (TEM-EDX) under a magnification condition of 50000 times by using an image analysis type particle size distribution measuring machine (Mac-View, manufactured by MOUNTECH). That is, in the cross section of the pixel division layer of the patterned substrate (100 mm×100 mm), silica particles (test n number 30) in the photographed image of 30 TEMs were randomly selected, and the long diameter, the short diameter, and the aspect ratio in the photographed image of the TEM were measured for each particle, and silica particles having a long diameter (nm) of 5 to 30nm and an aspect ratio in the range of 1.0 to 1.5 were defined as component (a). In the case where the short diameter and the long diameter in the captured image of the TEM are equal to each other, that is, in the case of a perfect circle, the diameter of 1 silica particle is regarded as the long diameter. As representative values showing characteristics of the silica particles belonging to the component (a), an average value of primary particle diameters, that is, an average value of long diameters is calculated, and a value obtained by rounding off the first decimal place and an average value of aspect ratios, that is, an average value of aspect ratios of the respective silica particles belonging to the component (a) are calculated, and a value obtained by rounding off the second decimal place is used.
The results of the cross-sectional analysis of examples 23, 24, and 25 in which the component (a) was present in table 10 are shown in table 11, with or without the component (a) being a, and with the component (a) being not B, in each of examples and comparative examples.
< diffuse reflectance measurement >)
For the diffuse reflectance measurement of the substrates in each of examples and comparative examples, the surface of the patterned substrate (100 mm. Times.100 mm) on which the pixel separation layer and the spacer were formed was measured using a spectrocolorimeter (manufactured by CM-2600d,KONICA MINOLTA JAPAN Co.), and the diffuse reflectance of 550nm wavelength in the SCE mode was used as the specular reflected light. The higher the diffuse reflectance, the more specular light can be suppressed, and the characteristics are determined to be good.
< test of adhesion >)
In the adhesion test of the organic EL display devices in each of examples and comparative examples, as shown in fig. 7, a metal cylinder having a diameter of 5mm was fixed to a central portion of a surface of a substrate (100 mm×100 mm) on which a light-emitting element was formed, the surface being opposite to the surface on which the light-emitting element was formed, and after repeating bending operation along the cylinder in a range from 0 ° of the wrap angle of the cylinder (a state in which the substrate is flat) to 180 ° of the wrap angle of the cylinder (a state in which the substrate is folded back on the basis of the cylinder), the bent portion was observed with an optical microscope. The peeling was judged to be characteristic (C) when the adhesion was low in the case of bending operation 1 to 100 times, characteristic (B) when it was 101 to 1000 times, and characteristic (a) when it was high in the case of 1001 times or more. The test was performed 10 times (the number of test n was 10), and the result that the number of times until peeling occurred was the smallest was adopted.
< test of weather resistance reliability >
The weather resistance reliability test of the organic EL display devices in each of the examples and comparative examples was performed after the organic EL display devices manufactured in each of the examples and comparative examples described later were left to stand at room temperature of 23 ℃ and humidity of 45% for 24 hours. In the test, 10 display devices (test n number is 10) were put in, and when no corrosion was observed in the second electrode, it was considered that the weather resistance was good, and it was determined that (a) was found that even when corrosion was observed in one of the electrodes, it was considered that pinholes were present in the second electrode, and it was determined that (B) was found that the second electrode was provided with pinholes.
< test of Electrical reliability >)
In the electrical reliability test of the organic EL display devices in each of the examples and comparative examples, the current value when a voltage of 5V was applied between the adjacent 2 stripe-shaped first electrodes was measured in the organic EL display devices fabricated in each of the examples and comparative examples described later. In the measurement, the smaller the current value, the smaller the leakage current, and the better the characteristics were determined, using a digital source meter (manufactured by 2400,Keithley Instruments). The test was performed at 20 (the number of test n was 20), and an average value of 10 times after 5 pieces of the measurement result were removed was used.
< test of luminescence Property >)
In the organic EL display devices produced in each of the examples and comparative examples described below, 10mA/cm was passed through 1 light-emitting element in which 1 pair of first and second electrodes intersecting each other was selected 2 The voltage and the luminance at this time were measured. For measurement of voltage, a digital source meter (manufactured by 2400,Keithley Instruments Co., ltd.) was used, and for measurement of luminance, a spectral radiance meter (manufactured by CS-1000,KONICA MINOLTA Co.) was used.
Design of first electrode and half tone photomask
Fig. 6 shows the designs of the first electrode and the halftone photomask in each of the examples and the comparative examples. As shown in fig. 6a, 100 first electrodes 2 having a line width of 60 μm, a pitch of 100 μm, and a length of 10mm were produced in a stripe shape at the central portion of the base material 1 (100 mm×100 mm). That is, the exposed portion of the base material 1 was 40 μm wide. On the other hand, in the positive type halftone photomask b, the line widths were adjusted at a pitch of 100 μm so that the light shielding portion 14 became a spacer and the semi-transmissive portion 13 became a pixel dividing layer. In the negative halftone photomask c, the line widths I and II are adjusted so that the light transmitting portion 12 serves as a spacer and the semi-light transmitting portion 13 serves as a pixel dividing layer. In any case, the pixel dividing layer and the spacers are aligned in the gap of the first electrode as shown in fig. 6. In the completed substrate, the line width I corresponds to the interface where the pixel division layer and the organic EL layer are in contact, and the line width II corresponds to the interface where the spacer and the organic EL layer are in contact.
Preparation of photosensitive resin composition
The photosensitive resin compositions R-1 to R-15 used in the examples and comparative examples were prepared in the following manner. Among the compounds used, a compound abbreviated as "is used, and the names are shown below.
BAHF:2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
BFE:1, 2-bis (4-formylphenyl) ethane
BIP-PHBZ:4,4',4 "-methylenetriphenol (manufactured by Asahi organic materials Co., ltd.)
BYK-333: organosilicon surfactant "BYK" (registered trademark) 333 (BYK-Chemie Co., ltd.)
DAE: diaminodiphenyl ethers
DFA: n, N-dimethylformamide dimethyl acetal
DMAA: n, N-dimethylacrylamide
DPCA-60: caprolactone 6 mol modified dipentaerythritol hexaacrylate (6 functional acrylate having 6 pentonoxy chains, manufactured by Nippon chemical Co., ltd.)
EL: lactic acid ethyl ester
FAMAC-6: 2- (perfluorohexyl) ethyl methacrylate
GBL: gamma-butyrolactone
GMA: glycidyl methacrylate
HA: hydroxy-containing diamine compound
HMOM-TPHAP: a compound (manufactured by Benzhou chemical industry Co., ltd.) having a phenolic hydroxyl group and substituents having a molecular weight of 40 or more at both ortho-positions with respect to the phenolic hydroxyl group, represented by the following chemical formula
[ chemical formula 13]
KBM-403: 3-epoxypropoxypropyl trimethoxysilane (Xinyue chemical Co., ltd.)
MAP: 3-aminophenol; m-aminophenol
MBA: acetic acid 3-methoxy-n-butyl ester
MEK-ST-40: silica particle dispersion (manufactured by Nissan chemical industries Co., ltd.). The solvent is methyl ethyl ketone
MEK-ST-L: silica particle dispersion (manufactured by Nissan chemical industries Co., ltd.). The solvent is methyl ethyl ketone
Memms: methyltrimethoxysilane
NA: 5-norbornene-2, 3-dicarboxylic acid anhydride; nadic acid anhydride
TMOS: tetramethoxysilane
NCI-831: "Adeka Arkls" (registered trademark) NCI-831 (manufactured by ADEKA)
NMP: n-methyl-2-pyrrolidone
ODPA: bis (3, 4-dicarboxyphenyl) ether dianhydride; oxydiphthalic dianhydride
OSCAL-1421: silica particle dispersion (manufactured by Nissan catalyst chemical industry Co., ltd.). The solvent is isopropanol
PGME: propylene glycol monomethyl ether
PGMEA: propylene glycol monomethyl ether acetate
PhTMS: phenyl trimethoxysilane
S0100CF: irgaphor Black (registered trademark) S0100CF
SiDA:1, 3-bis (3-aminopropyl) tetramethyldisiloxane
S-20000: "SOLSPERSE" (registered trademark) 20000 (polyether dispersant, manufactured by Lubrizol)
Tmsu ca: 3-trimethoxysilylpropyl succinic anhydride
TrisP-PA:1, 1-bis (4-hydroxyphenyl) -1- [4- [1- (4-hydroxyphenyl) -1-methylethyl ] phenyl ] ethane (manufactured by Benzhou chemical industry Co., ltd.)
WR-301: "ADEKA ARKLS" (registered trademark) WR-301 (manufactured by ADEKA)
Karenz MOI-BM: 2- (0- [1' -Methylpropyleneamino ] carboxyamino) ethyl methacrylate
Bisphenol AF:2, 2-bis (4-hydroxyphenyl) hexafluoropropane (manufactured by Central Glass Co., ltd.)
6FDA:2,2- (3, 4-dicarboxyphenyl) hexafluoropropane dianhydride; 4,4' -hexafluoropropane-2, 2-diyl-bis (1, 2-phthalic anhydride)
Pigment dispersant 1: pigment dispersant 1 (solid content 100% by weight) disclosed in synthesis example 2 of Japanese patent application laid-open No. 2020/70352. A polymer type dispersant having a linear polyalkyleneamine structure and a polyether polymer chain.
Synthesis example 1 Synthesis of polyimide resin (PI-1)
31.13g (0.085 mol; 77.3mol% with respect to structural units derived from all amines and derivatives thereof) of BAHF, 1.24g (0.0050 mol; 4.5mol% with respect to structural units derived from all amines and derivatives thereof) of SiDA, 2.18g (0.020 mol; 18.2mol% with respect to structural units derived from all amines and derivatives thereof) of MAP as a capping agent, 150.00g of NMP were weighed out in a three-necked flask under a dry nitrogen flow, and dissolved. To this was added a solution of 31.02g (0.10 mol; 100mol% relative to the structural units derived from the whole carboxylic acid and its derivatives) of ODPA dissolved in 50.00g of NMP, and stirred at 20℃for 1 hour, followed by 50℃for 4 hours. Then, 15g of xylene was added thereto, and the mixture was stirred at 150℃for 5 hours while azeotroping water with xylene. After the completion of the reaction, the reaction solution was poured into 3L of water, and the resultant was filtered to obtain a solid precipitate. The obtained solid was washed 3 times with water and dried by a vacuum dryer at 80℃for 24 hours to obtain a polyimide resin (PI-1). The polyimide resin (PI-1) thus obtained had a weight average molecular weight (Mw) of 27,000 and an acid equivalent weight of 350.
Synthesis example 2 Synthesis of HA
In a three-necked flask, 18.31g (0.05 mol) of BAHF, 17.42g (0.3 mol) of propylene oxide, 100mL of acetone were weighed and dissolved. A solution of 20.41g (0.11 mol) of 3-nitrobenzoyl chloride dissolved in 10mL of acetone was added dropwise thereto. After the completion of the dropwise addition, the reaction was carried out at-15℃for 4 hours, and then the reaction was returned to room temperature. The white solid precipitated was filtered off and dried in vacuo at 50 ℃. 30g of the obtained solid was placed in a 300mL stainless steel autoclave, dispersed in 250mL of 2-methoxyethanol, and 2g of 5% palladium-carbon was added. Hydrogen was introduced thereinto with a balloon, and the mixture was reacted at room temperature for 2 hours. After 2 hours, it was confirmed that the balloon was no longer collapsed. After the completion of the reaction, the reaction mixture was filtered, and the palladium compound as a catalyst was removed and concentrated by distillation under reduced pressure to obtain a hydroxyl group-containing diamine compound (HA) having the following structure.
[ chemical formula 14]
Synthesis example 3 Synthesis of polyimide precursor resin (PIP-1)
44.42g (0.10 mol; 100mol% relative to the structural units derived from the entire carboxylic acid and its derivatives) of 6FDA and 150g of NMP were weighed and dissolved in a three-necked flask under a dry nitrogen flow. To this was added a solution of 14.65g (0.040 mol; 32.0mol% with respect to structural units derived from all amines and derivatives thereof) of BAHF, 18.14g (0.030 mol; 24.0mol% with respect to structural units derived from all amines and derivatives thereof) of HA, 1.24g (0.0050 mol; 4.0mol% with respect to structural units derived from all amines and derivatives thereof) of SiDA dissolved in 50g of NMP, and stirred at 20℃for 1 hour, followed by stirring at 50℃for 2 hours. Next, a solution of 5.46g (0.050 mol; 40.0mol% relative to the structural units derived from the entire amine and its derivatives) of MAP dissolved as a capping agent in 15g of NMP was added, and stirred at 50℃for 2 hours. Then, a solution of 23.83g (0.20 mol) of DFA dissolved in 15g of NMP was added. After the completion of the addition, the mixture was stirred at 50℃for 3 hours. After the completion of the reaction, the reaction solution was cooled to room temperature, and then the reaction solution was poured into 3L of water, and the solid precipitate was obtained by filtration. After the obtained solid was washed 3 times with water, it was dried with a vacuum dryer at 80℃for 24 hours to obtain a polyimide precursor resin (PIP-1). The polyimide precursor resin (PIP-1) obtained had a weight average molecular weight (Mw) of 20,000 and an acid equivalent of 450.
Synthesis example 4 Synthesis of polyimide precursor resin (PIP-2)
21.2g (0.035 mol) of HA, 7.0g (0.035 mol) of DAE, 1.2g (0.005 mol) of SiDA obtained in Synthesis example 2 were dissolved in 400g of NMP under a dry nitrogen flow. To this, 31.0g (0.10 mol) of ODPA was added together with 50g of NMP, and stirred at 40℃for 1 hour. Then, 5.5g (0.050 mol) of MAP was added thereto and stirred at 40℃for 1 hour. Further, a solution in which 8.3g (0.07 mol) of DFA was dissolved in 10g of NMP was added. After the completion of the addition, the mixture was stirred at 40℃for 3 hours. After the completion of stirring, the solution was cooled to room temperature, and then the solution was poured into 3L of water to obtain a white precipitate. The precipitate was collected by filtration, washed 3 times with water, and dried with a vacuum dryer at 50℃for 72 hours to give an alkali-soluble resin (PIP-2) comprising a polyimide precursor resin having an acid equivalent of 275 g/mol.
Synthesis example 5 Synthesis of polyimide precursor resin (PIP-3)
The amount of DFA charged in the same manner as in Synthesis example 4 was set to 13.1g (0.11 mol), whereby an alkali-soluble resin (PIP-3) containing a polyimide precursor resin having an acid equivalent of 329g/mol was obtained.
Synthesis example 6 Synthesis of polyimide precursor resin (PIP-4)
The amount of DFA charged in the same manner as in Synthesis example 4 was set to 16.7g (0.14 mol), whereby an alkali-soluble resin (PIP-4) containing a polyimide precursor resin having an acid equivalent of 366g/mol was obtained.
Synthesis example 7 Synthesis of polybenzoxazole resin (PBO-1)
34.79g (0.095 mol; 95.0mol% relative to structural units derived from all amines and derivatives thereof) of BAHF, 1.24g (0.0050 mol; 5.0mol% relative to structural units derived from all amines and derivatives thereof) of SiDA, 75.00g of NMP were weighed into a 500mL round bottom flask fitted with a Dean-Stark trap filled with toluene and a condenser, and dissolved. To this was added a solution of 19.06g (0.080 mol; 66.7mol% with respect to structural units derived from all carboxylic acids and derivatives thereof) of BFE, 6.57g (0.040 mol; 33.3mol% with respect to structural units derived from all carboxylic acids and derivatives thereof) of NA as a capping agent dissolved in 25.00g of NMP, stirred at 20℃for 1 hour, followed by stirring at 50℃for 1 hour. Then, the mixture was heated and stirred at 200℃or higher for 10 hours under nitrogen atmosphere to carry out dehydration reaction. After the completion of the reaction, the reaction solution was poured into 3L of water, and the resultant was filtered to obtain a solid precipitate. After the obtained solid was washed 3 times with water, it was dried with a vacuum dryer at 80℃for 24 hours to obtain a polybenzoxazole resin (PBO-1). The weight average molecular weight (Mw) of the obtained polybenzoxazole resin (PBO-1) was 25,000 and the acid equivalent was 330.
Synthesis example 8 Synthesis of polybenzoxazole precursor resin (PBOP-1)
34.79g (0.095 mol; 95.0mol% relative to structural units derived from all amines and derivatives thereof) of BAHF, 1.24g (0.0050 mol; 5.0mol% relative to structural units derived from all amines and derivatives thereof) of SiDA, 70.00g of NMP were weighed into a 500mL round bottom flask fitted with a Dean-Stark trap filled with toluene and a condenser, and dissolved. To this was added a solution of BFE in which 19.06g (0.080 mol; 66.7mol% relative to the structural units derived from the whole carboxylic acid and its derivatives) was dissolved in 20.00g of NMP, and stirred at 20℃for 1 hour, followed by 50℃for 2 hours.
Next, a solution of 6.57g (0.040 mol; 33.3mol% relative to the structural units derived from the entire carboxylic acid and its derivatives) of NA as a blocking agent dissolved in 10g of NMP was added and stirred at 50℃for 2 hours. Then, the mixture was stirred at 100℃for 2 hours under a nitrogen atmosphere. After the completion of the reaction, the reaction solution was poured into 3L of water, and the resultant was filtered to obtain a solid precipitate. After the obtained solid was washed 3 times with water, it was dried with a vacuum dryer at 80℃for 24 hours to obtain a polybenzoxazole precursor resin (PBOP-1). The weight average molecular weight (Mw) of the obtained polybenzoxazole precursor resin (PBOP-1) was 20,000 and the acid equivalent was 330.
Synthesis example 9 Synthesis of polysiloxane resin solution (PS-1)
A three-necked flask was charged with 23.84g (35 mol%) of MeTMS, 49.57g (50 mol%) of PhTMS, 3.81g (5 mol%) of TMOS, and 76.36g of PGMEA. Air was introduced into the flask at 0.05L/min, and the mixed solution was heated to 40℃with stirring by an oil bath. While stirring the mixed solution further, an aqueous phosphoric acid solution obtained by dissolving 0.271g of phosphoric acid in 28.38g of water was added dropwise over 10 minutes. After the completion of the dropwise addition, the mixture was stirred at 40℃for 30 minutes to hydrolyze the silane compound. After the hydrolysis was completed, a solution of 13.12g (10 mol%) of TMSSucA dissolved in 8.48g of PGMEA was added. Then, after the bath temperature was set to 70℃and stirred for 1 hour, the bath temperature was then raised to 115 ℃. After the initiation of the temperature rise, the internal temperature of the solution reached 100℃after about 1 hour, and the mixture was heated and stirred for 2 hours from this point (the internal temperature was 100 to 110 ℃). The resin solution obtained by heating and stirring for 2 hours was cooled in an ice bath, and then anion exchange resin and cation exchange resin were added in amounts of 2 wt% relative to the resin solution, respectively, and stirred for 12 hours. After stirring, the anion exchange resin and the cation exchange resin were removed by filtration to obtain a polysiloxane resin solution (PS-1). The polysiloxane resin obtained had a weight average molecular weight (Mw) of 4,200 and a carboxylic acid equivalent (acid equivalent) of 700g/mol.
Synthesis example 10 Synthesis of sensitizer (quinone diazide compound b-1)
21.22g (0.05 mol) of TrisP-PA (trade name, manufactured by Benzhou chemical Co., ltd.) and 36.27g (0.135 mol) of 5-naphthoquinone diazide sulfonyl chloride were dissolved in 450g of 1, 4-dioxane under a dry nitrogen stream, and left at room temperature. 15.18g of triethylamine mixed with 50g of 1, 4-dioxane was added dropwise thereto so that the temperature in the system did not reach 35℃or higher. After the dropwise addition, the mixture was stirred at 30℃for 2 hours. The triethylamine salt was filtered and the filtrate was put into water. The precipitated precipitate was then collected by filtration. The precipitate was dried by a vacuum dryer to obtain a sensitizer (quinone diazide compound b-1) of the following structure.
[ chemical formula 15]
< preparation of salt-forming Compound d-1 >
Into a separable flask were charged 9.25g (0.018 mol) of c.i. basic blue 7 as a basic dye, 200g of pure water, and stirred at 60 ℃ for 30 minutes. An aqueous solution of 11.50g (0.019.8 mol) of c.i. acid red 52 as an acid dye dissolved in 120g of pure water was added thereto, and the mixture was stirred at 60 ℃ for 60 minutes. Then, the heating was stopped, and the mixture was cooled to room temperature with stirring. After cooling to room temperature, the reaction solution was filtered to obtain a purple solid. The solid was dried under reduced pressure at 60℃for 8 hours to give a salt-forming compound d-1.
< preparation of salt-forming Compound d-2 >
The salt-forming compound d-2 was obtained by using c.i. basic blue 26 as a basic dye instead of c.i. basic blue 7 in the same manner as d-1.
Preparation of pigment Dispersion 1
To 742.39g of PGMEA as a solvent component, 15.00g of S-20000 as a pigment-dispersing agent having a basic group was added, and then 2.70g of a PGMEA solution containing 1.00 wt% of 4-methylbenzenesulfonic acid was added. Then, after stirring at atmospheric pressure/a liquid temperature of 25℃for 1 hour, the mixture was allowed to stand for 6 hours, whereby the basic group of S-20000 and the sulfo group of 4-methylbenzenesulfonic acid were previously salified. Further, 149.91g of an alkali-soluble resin solution (a resin solution obtained by dissolving the PIP-1 in such a manner that the solid content becomes 30 wt% using PGMEA (solid content: 30.0 wt%) was added), and after stirring for 30 minutes, 90.00g of a benzodifuranone black pigment represented by the following structure was mixed and stirred for 20 minutes, to obtain a pre-dispersion. The pre-dispersion was fed to a dispersion medium filled with 75% by volumeIn a bead mill ("Torayceram" (registered trademark), manufactured by eastern co.ltd., ltd.) was subjected to 1 dispersion treatment, followed by a wet medium dispersion treatment in a circulating manner. After 30 minutes, the pigment dispersion was taken out from the outlet of the disperser into a glass bottle, and the pigment dispersion thus obtained was set in a laser diffraction/scattering particle size distribution measuring apparatus (UPA 150, manufactured by Microtrac corporation) to measure the average dispersion particle diameter. The pigment dispersion having an average dispersion particle diameter at the time point of 30 minutes from sampling as a median particle diameter D50 (cumulative 50% volume average diameter) of 150±10nm and as a median particle diameter D90 (cumulative 90% volume average diameter) of 300±30nm was regarded as "pigment dispersion 1".
[ chemical formula 16]
Preparation of pigment Dispersion 2
The same procedure as for "pigment dispersion 1" was used to dissolve PIP-1 using MBA instead of PGMEA, to prepare "pigment dispersion 2".
Preparation of pigment Dispersion 3
200g of zirconium nitride particles (manufactured by ZrN, NISSHINENGINEERING Co., ltd.), 50g of polyimide precursor resin (PIP-1), and 1000g of gamma-butyrolactone (GBL) manufactured by a thermal plasma method were charged into a tank, and stirred with a homomixer for 20 minutes to obtain a pre-dispersion. To 75% by volume ofDispersion machine with centrifugal separator for zirconia beads (Ultra Apex Mill, HIROSHIMA METAL)&MACHINERY), and the obtained pre-dispersion was dispersed at a rotational speed of 10m/s for 3 hours to obtain a pigment dispersion 3 having a solid content concentration of 20 wt% and a coloring material/resin (weight ratio) =80/20. The composition is shown in Table 1.
TABLE 1
TABLE 1
Preparation of pigment Dispersion 4
The charged alkali-soluble resin was made PIP-2 by the same method as in the pigment dispersion liquid 3, thereby obtaining a pigment dispersion liquid 4.
Preparation of pigment Dispersion 5
The pigment dispersion 5 was obtained by setting the alkali-soluble resin charged to PIP-3 in the same manner as in the pigment dispersion 3.
Preparation of pigment Dispersion 6
The charged alkali-soluble resin was made PIP-4 by the same method as in the pigment dispersion liquid 3, thereby obtaining a pigment dispersion liquid 6.
Preparation of pigment Dispersion 7
To 770.00g of PGMEA as a solvent, 30.00g of pigment dispersant 1 was added, followed by stirring for 5 minutes, 100.00g of ZCR-1569H was added, and stirring was continued for 30 minutes. Further, 100.00g of S0100CF was added as the component (b), followed by stirring for 30 minutes to obtain a pre-stirred solution. The pre-stirred solution was fed to a container filled with the solution at a filling rate of 75% by volumeIn a vertical bead mill of composite oxide (zirconia: hafnium oxide: yttrium oxide: aluminum oxide=93.3:1.5:4.9:0.3 by weight, manufactured by Toli corporation), a first wet medium dispersion treatment was performed in a cyclic manner at a peripheral speed of 8m/s for 3 hours. Further, the liquid is fed to the container filled with +.>In a vertical bead mill having a composite oxide of a crushing medium (zirconium oxide: hafnium oxide: yttrium oxide: aluminum oxide=93.3:1.5:4.9:0.3, manufactured by Toli corporation), a second wet medium dispersion treatment was performed at a peripheral speed of 9m/s for 6 hours in a cyclic manner, and then filtration was performed by a filter having a diameter of 0.8 μm, whereby a pigment dispersion liquid 1 having a solid content of 20.00 wt% was produced. The blending weights of the respective raw materials are shown in Table 2.
TABLE 2
Preparation of photosensitive resin composition R-1
Under a yellow lamp, the gamma-butyrolactone (GBL) and Ethyl Lactate (EL) were 1:1, a polyimide precursor resin PI-1 obtained in synthesis example 1 as an alkali-soluble resin (a), a compound B-1 obtained in synthesis example 10 as a photosensitizer (B), a compound D-1 as a salt-forming compound formed from an acid dye and a basic dye, a c.i. solvent blue 45 as a nonionic dye D-3, a thermally chromogenic compound f-1 (BIP-PHBZ) represented by the following structure, a thermal crosslinking agent g-1 (HMOM-TPHAP) as another additive, a compound h-1 (bisphenol AF) having a phenolic hydroxyl group, and an adhesion improver i-1 (KBM-403) were added in amounts shown in table 3, and stirred and dissolved to prepare a positive photosensitive resin composition R-1.
[ chemical formula 17]
TABLE 3
Preparation of photosensitive resin compositions R-2 to R-6
R-2 to R-6 were prepared in the same manner as R-1, with the compositions shown in Table 3.
Preparation of photosensitive resin composition R-7
Under a yellow lamp, 0.20g of NCI-831 as a sensitizer was added to 13.01g of PGMEA, and the mixture was stirred for 3 minutes to dissolve the same. To this, 4.28g of an alkali-soluble polyimide resin solution A (a resin solution obtained by dissolving PI-1 with PGMEA so that the solid content becomes 30% by weight) and 1.02g of an alkali-soluble Cardo resin solution A (an amine value of 0 (mgKOH/g), a resin acid value of 90 (mgKOH/g), and a solid content of 44.2% by weight were added, "ADEKA ARKLS" (registered trademark) WR-301 (manufactured by ADEKA), which is a PGMEA solution of an alkali-soluble Cardo resin having a carboxyl group as an alkali-soluble group, were added, and 0.99g of DPCA-60, which is a compound having 2 or more radical-polymerizable groups, were stirred to obtain a blended solution. This blended solution was mixed with 10.50g of pigment dispersion 1 sampled from the supernatant of a glass bottle container, and stirred for 30 minutes to obtain negative photosensitive resin composition R-7. The blending amounts of the raw materials are shown in Table 4.
TABLE 4
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Preparation of photosensitive resin composition R-8
A negative photosensitive resin composition R-8 was prepared by using an alkali-soluble polyimide resin solution B (a resin solution obtained by dissolving PI-1 in MBA so that the solid content became 30 wt%) instead of the alkali-soluble polyimide resin solution a, and using a pigment dispersion 2 instead of the pigment dispersion 1, by the same procedure as R-7. The blending amounts of the raw materials are shown in Table 4.
Synthesis example 11 Synthesis of lyophobic Material (e-1) and (e-2)
To a 1000mL reaction vessel equipped with a stirring device, a reflux condenser, a dropping funnel, a thermometer and a nitrogen gas inlet, 100 parts by weight of cyclohexanone was added, and the temperature was raised to 110℃under a nitrogen gas atmosphere. The monomer mixed solutions shown in table 5 were added dropwise using a dropping funnel at a constant rate of 2 hours while maintaining the temperature of cyclohexanone at 110 ℃. After the completion of the dropwise addition, the monomer solution was heated to 115℃and reacted for 2 hours to obtain lyophobic materials (e-1) and (e-2).
TABLE 5
/>
Synthesis example 12 Synthesis of phenolic resin (j-1)
Under a dry nitrogen stream, 108.0g (1.00 mol) of m-cresol, 75.5g (0.93 mol) of 37 wt% aqueous formaldehyde solution, 0.63g (0.005 mol) of oxalic acid dihydrate and 264g of methyl isobutyl ketone were charged, and the reaction mixture was refluxed while carrying out polycondensation reaction for 4 hours. Then, the temperature of the oil bath was raised over 3 hours, and then the pressure in the flask was reduced to 4.0kPa to 6.7kPa, volatile components were removed, and the dissolved resin was cooled to room temperature to obtain a Novolac phenol resin (j-1). According to GPC, the weight average molecular weight was 3,500.
Preparation of photosensitive resin compositions R-9 and R-10
The components were mixed in the mixing ratio shown in table 6 under a yellow lamp, and the mixture was stirred sufficiently at room temperature to dissolve the components. Then, the obtained solution was filtered through a filter having a pore size of 1. Mu.m, to obtain positive photosensitive resin compositions R-9 and R-10.
TABLE 6
Preparation of photosensitive resin composition R-11
To 93.8g of pigment dispersion 3, 50.5g of alkali-soluble resin (PIP-1), 17.0g of quinone diazide compound (b-1) as a photoacid generator, 13.6g of phenol compound (h-1, bisphenol AF), 0.2g of silicone surfactant (BYK-333), 105.0g of GBL, 720.0g of PGME were added to give a positive photosensitive resin composition R-11 having a total solid content concentration of 10% by weight and a pigment/resin (weight ratio) =15/85. The composition is shown in Table 7.
TABLE 7
Preparation of photosensitive resin composition R-12
The same method as for R-11 was used to obtain a positive photosensitive resin composition R-12 by substituting the pigment dispersion 3 with the pigment dispersion 4 and substituting PIP-1 with PIP-2 as the alkali-soluble resin. The composition is shown in Table 7.
Preparation of photosensitive resin composition R-13
The same method as for R-11 was used to obtain a positive photosensitive resin composition R-13 by substituting the pigment dispersion 3 with the pigment dispersion 5 and substituting PIP-1 with PIP-3 as the alkali-soluble resin. The composition is shown in Table 7.
Preparation of photosensitive resin composition R-14
The same method as for R-11 was used to obtain a positive photosensitive resin composition R-14 by substituting the pigment dispersion 3 with the pigment dispersion 6 and substituting PIP-1 with PIP-4 as the alkali-soluble resin. The composition is shown in Table 7.
Preparation of photosensitive resin composition R-15
Polyimide precursor resin (PIP-1) (10.0 g) as (a) alkali-soluble resin, f-1 (1.2 g) as (B) sensitizer, and PGME (32.0 g) and GBL (8.0 g) as (C) organic solvent were added under a yellow lamp. Then, usingThe obtained solution was filtered to obtain a positive photosensitive resin composition R-15.
Preparation of photosensitive resin composition R-16
To a mixed solvent of 8.50g of MBA and 16.16g of PGMEA, 0.38g of OXE03 as a photopolymerization initiator was added under a yellow lamp, and the mixture was stirred for 10 minutes to dissolve the same. To this was added 1.88g of MEK-ST-40 as the silica particle dispersion (component (a)), and the mixture was stirred for 10 minutes to dissolve the silica particles. Next, 4.61G of ZAH-106, 0.45G of TR4020G, 0.38G of DPCA-60, and 0.97G of GA-5060P were added and stirred for 30 minutes to give a clear blend. To this blend, 16.69g of pigment dispersion 7 was mixed and stirred for 30 minutes to prepare a negative photosensitive resin composition R-16 having a solid content of 15.00 wt%. The blending weights of the respective raw materials are shown in Table 8.
TABLE 8
Preparation of photosensitive resin composition R-17
As in the case of R-16, OSCAL-1421 was used in place of MEK-ST-40 to prepare a negative photosensitive resin composition R-17 in the amount shown in Table 8. The blending weights of the respective raw materials are shown in Table 8.
Preparation of photosensitive resin composition R-18
As in the case of R-16, a negative photosensitive resin composition R-18 was prepared using MEK-ST-L instead of MEK-ST-40 in the amounts shown in Table 8. The blending weights of the respective raw materials are shown in Table 8.
Examples 1 to 25 and comparative examples 1 to 3 >, respectively
The surface roughness of the pixel dividing layer and the spacer, the diffuse reflection light of the substrate, the adhesion of the organic EL display device, the weather resistance reliability, the electrical reliability, and the light emission characteristics in each of the examples and the comparative examples were evaluated as follows.
First, agPdCu (100 nm) and crystalline ITO (10 nm) as first electrodes were sequentially formed into 100 strips having a line width of 60 μm, a pitch of 100 μm, and a length of 10mm by vacuum sputtering at the central portion of a PET substrate of 100mm×100 mm. That is, the exposed portion of the substrate was 40 μm wide. The photosensitive resin compositions according to the examples and comparative examples shown in table 9 were applied by spin coating, and then baked on a hot plate at 100 ℃ for 2 minutes to form a film.
After UV exposure of the film via a halftone photomask shown in table 9, development was performed with a 2.38% tmah aqueous solution, and only the unexposed portion was dissolved in the case of negative type, and only the exposed portion was dissolved in the case of positive type, followed by rinsing with pure water to obtain a pattern. Then, the resultant was cured in an oven at 250℃under a nitrogen atmosphere for 60 minutes to obtain a substrate having a pattern of the pixel dividing layer and the spacers. In all examples and comparative examples, the rotation speed was adjusted so that the thickness of the pixel dividing layer was 1.5um and the thickness of the spacer was 1.5um.
In comparative example 1, a photomask commonly called a full tone mask having no semi-transmissive portion was used to manufacture the pixel dividing layer and the spacer, respectively. That is, after the application, pre-baking, exposure, development, and curing of the pixel division layer, the process of applying, pre-baking, exposure, development, and curing of the spacer is performed. In comparative example 3, roughening treatment in RIE mode, oxygen, 1000W, and 60 seconds was performed after curing using a plasma treatment apparatus (SPC-100B+H,Hitachi High-Technologies).
In this state, the surface roughness of the pixel dividing layer and the spacer and the diffuse reflection light of the substrate were evaluated, and the results are shown in table 10.
Next, the organic EL layer was formed over the entire surface of the patterned substrate by a vacuum deposition method. The vacuum degree at the time of vapor deposition was set to 1×10 -3 Pa or less, and rotating the substrate relative to the vapor deposition source during vapor deposition. First, as a hole injection layer, the compound (HT-1) was evaporated to 10nm, and as a hole transport layer, the compound (HT-2) was evaporated to 50nm. Next, as the light-emitting layer, the compound (GH-1) as a host material and the compound (GD-1) as a dopant material were vapor deposited to a thickness of 40nm so that the doping concentration became 10% by volume. Next, as an electron transport layer, the compound (ET-1) and LiQ were mixed in a volume ratio of 1:1 are laminated to a thickness of 40 nm. The hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer described above are referred to as a first light emitting unit.
Then, liQ of 2nm was vapor deposited as an electron injection layer. The structure of the compound used as the organic EL layer is shown below.
[ chemical formula 18]
[ chemical formula 19]
Further, mg and Ag were mixed in a volume ratio of 10:1 were vapor deposited at 10nm as 20 stripe-like second electrodes having a line width of 400 μm, a pitch of 500 μm and a length of 10 mm. The film thickness referred to herein is a value displayed by a quartz oscillation type film thickness monitor.
In this way, an organic EL display device having 200 light emitting elements in which 100 first electrodes, 20 second electrodes, and the like intersect was completed. Fig. 8 is a schematic view of the organic EL display device of the present embodiment, and fig. 9 is a schematic view of a light-emitting element in which an organic EL layer is omitted. Then, the adhesion, weather resistance reliability, and electrical reliability of the organic EL display device were evaluated. The results are shown in Table 10.
[ Table 9-1]
[ Table 9-2]
TABLE 10-1
TABLE 10-2
TABLE 11
Example 26 >
An organic EL display device was produced in the same manner as in example 1 except that, in the first light-emitting unit, only the compound (ET-1) was used instead of LiQ in the electron transport layer, and the adhesion, weather resistance reliability, electrical reliability, and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 27 >
An organic EL display device was produced in the same manner as in example 1 except that, in the first light-emitting unit, only the compound (ET-2) was used instead of LiQ in the electron transport layer, and the adhesion, weather resistance reliability, electrical reliability, and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 28 >
An organic EL display device was produced in the same manner as in example 1 except that, in the first light-emitting unit, only the compound (ET-3) was used instead of LiQ in the electron transport layer, and the adhesion, weather resistance reliability, electrical reliability, and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 29 >
An organic EL display device was produced in the same manner as in example 1 except that, in the first light-emitting unit, only the compound (ET-4) was used instead of LiQ in the electron transport layer, and the adhesion, weather resistance reliability, electrical reliability, and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 30 >
After a patterned substrate was obtained in the same manner as in example 1, a first light-emitting unit was laminated as an organic EL layer. Then, on the first light-emitting cell, as an n-type charge generation layer, the compound (ET-1) and the metal Li as a doping material were formed into a compound (ET-1) at a deposition rate ratio: li=99: 1, and then, as a p-type charge generation layer, the compound (HT-1) was evaporated to 10nm.
After the charge generation layer, the same organic EL layer as the first light emitting unit is formed again, thereby making a tandem type. Then, liQ was vapor deposited as an electron injection layer for 2nm. Further, mg and Ag were mixed in a volume ratio of 10:1 were vapor deposited at 10nm as 20 stripe-like second electrodes having a line width of 400 μm, a pitch of 500 μm and a length of 10 mm. The film thickness referred to herein is a value displayed by a quartz oscillation type film thickness monitor.
In this way, an organic EL display device having 200 light emitting elements where 100 first electrodes, 20 second electrodes, and they intersect was completed. Then, the adhesion, weather resistance, electrical reliability, and light emission characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 31 >
An organic EL display device was produced in the same manner as in example 30, except that the compound (ET-1) in the n-type charge generation layer was changed to the compound (ET-2), and the adhesiveness, weather resistance reliability, electrical reliability and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 32 >
An organic EL display device was produced in the same manner as in example 30, except that the compound (ET-1) in the n-type charge generation layer was changed to the compound (ET-3), and the adhesiveness, weather resistance reliability, electrical reliability and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Example 33 >
An organic EL display device was produced in the same manner as in example 30, except that the compound (ET-1) in the n-type charge generation layer was changed to the compound (ET-4), and the adhesiveness, weather resistance reliability, electrical reliability and light-emitting characteristics of the organic EL display device were evaluated. The conditions of the photosensitive resin composition and photomask are shown in table 9, and the evaluation results are shown in table 10.
Description of the reference numerals
1. Substrate material
2. First electrode
3. Pixel dividing layer
4. Spacing piece
5. Organic EL layer
6. Second electrode
7 TFT
8. Planarization layer
9. Sealing layer
10. Polarizing layer
11. Ultraviolet absorbing layer
12. Light transmitting part
13. Semi-transparent part
14. Light shielding part
15. Cylinder column
16 Range of Ra1 to be measured
17 Range of Ra2 to be measured
18. Organic EL display device
19. Light-emitting element
Claims (18)
1. An organic EL display device having a substrate, which has a first electrode, a pixel dividing layer, and a spacer on a base material, and an organic EL layer and a second electrode,
When the maximum value between the surface roughness (Ra 1) of the pixel dividing layer and the surface roughness (Ra 2) of the spacer is Ramax, ramax is 1.0nm to 50 nm.
2. The organic EL display device as claimed in claim 1, wherein Ra1 becomes Ramax.
3. The organic EL display device according to claim 2, wherein an area of an interface between the substrate and the organic EL layer is 50% or more of an area of an interface between the pixel dividing layer and the organic EL layer.
4. The organic EL display device as claimed in claim 1, wherein Ra2 becomes Ramax.
5. The organic EL display device according to claim 4, wherein an area of an interface between the substrate and the organic EL layer is 50% or more of an area of an interface between the spacer and the organic EL layer.
6. The organic EL display device according to any one of claims 1 to 5, wherein an absolute value of a difference between Ra1 and Ra2 is 1.0nm or more.
7. The organic EL display device as claimed in any one of claims 1 to 6, wherein the pixel dividing layer comprises silica particles having a primary particle diameter of 5 to 30 nm.
8. The organic EL display device as claimed in any one of claims 1 to 7, wherein the pixel-dividing layer comprises a cured film of a photosensitive resin composition containing an alkali-soluble resin.
9. The organic EL display device according to claim 8, wherein the alkali-soluble resin contains 1 or more selected from the group consisting of an acrylic resin, a phenolic resin, a polysiloxane resin, a Cardo resin, a polyimide precursor resin, a polybenzoxazole resin, and a polybenzoxazole precursor resin.
10. The organic EL display device as claimed in claim 8 or 9, wherein the photosensitive resin composition comprises a coloring material.
11. The organic EL display device as claimed in any one of claims 8 to 10, wherein the photosensitive resin composition comprises a lyophobic material.
12. The organic EL display device as claimed in any one of claims 1 to 11, wherein the organic EL layer comprises an electron transport layer and/or a charge generation layer.
13. An organic EL display device as claimed in claim 12 wherein the electron transport layer and/or charge generation layer comprises a donor dopant.
14. The organic EL display device according to claim 13, wherein the donor-type dopant contains 1 or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, inorganic salts of the metals, and complexes of the metals and organic substances.
15. The organic EL display device according to any one of claim 12 to 14, wherein the electron transporting layer and/or the charge generating layer comprises a compound having a phenanthroline skeleton represented by the following general formula (1),
[ chemical formula 1]
Here, R is 1 ~R 8 Each of which may be the same or different and is selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, and a heterocyclic group; wherein R is 1 、R 3 、R 6 、R 8 At least one of them is selected from adamantyl, norbornyl, phenylvinyl, beta-naphthyl, phenanthryl, pyrenyl.
16. The organic EL display device according to any one of claim 12 to 14, wherein the electron transporting layer and/or the charge generating layer comprises a compound having a phenanthroline skeleton represented by the following general formula (2),
[ chemical formula 2]
Here, R is 9 ~R 16 Each of which may be the same or different, is selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, a heteroaryl group, a heterocyclic group, and X 1 Is selected; wherein R is 9 ~R 16 At least one of them is X 1 The method comprises the steps of carrying out a first treatment on the surface of the n represents a natural number of 2 to 6; x is X 1 Is a single bond, or an n-valent linking unit derived from any one of benzene, anthracene, pyridine, ethylene, thiophene, furan, methylene, carbazole, cyclohexane, spirobifluorene, triphenylamine, triptycene, and a structure formed by combining them, and linking a plurality of phenanthroline skeletons.
17. A method for manufacturing an organic EL display device, comprising a substrate having a first electrode, a pixel dividing layer, and a spacer on a base material,
the manufacturing method includes a step of processing the pixel division layer and the spacer together, and the photomask used for the processing together is a half-tone photomask having a light transmitting portion, a light shielding portion, and a semi-light transmitting portion.
18. The method for manufacturing an organic EL display device as claimed in claim 17, wherein the transmittance of the semi-transparent portion is 15 to 50% of the transmittance of the transparent portion.
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