CN112467048A - Organic light-emitting element including capping layer and capping layer compound suitable for use in the organic light-emitting element - Google Patents

Organic light-emitting element including capping layer and capping layer compound suitable for use in the organic light-emitting element Download PDF

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CN112467048A
CN112467048A CN202010921212.9A CN202010921212A CN112467048A CN 112467048 A CN112467048 A CN 112467048A CN 202010921212 A CN202010921212 A CN 202010921212A CN 112467048 A CN112467048 A CN 112467048A
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organic light
compound
emitting element
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咸昊完
安贤哲
金熙宙
金东骏
韩政佑
金昇好
安慈恩
权桐热
李成圭
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Dongjin Semichem Co Ltd
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    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • H10K50/865—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. light-blocking layers
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract

The present invention relates to an organic light-emitting device including a cap layer and a compound for a cap layer suitable for the organic light-emitting device, and provides an organic light-emitting device in which the cap layer includes a compound having a difference of more than 0.15 between a refractive index at 450nm and a refractive index at 530nm, and a compound for a cap layer suitable for the organic light-emitting device.

Description

Organic light-emitting element including capping layer and capping layer compound suitable for use in the organic light-emitting element
Technical Field
The present invention relates to an organic light-emitting element including a cap layer and a compound for a cap layer suitable for the organic light-emitting element.
Background
Recently, a self-luminous organic light emitting device capable of being driven at a low voltage has been attracting attention as a next-generation display device because it is superior to a Liquid Crystal Display (LCD), which is a mainstream of a flat display device, in view angle and contrast ratio, does not require a backlight, can be reduced in weight and thickness, consumes less power, has a wide color reproduction range, and the like.
Materials used as an organic layer in an organic light emitting diode can be broadly classified into a light emitting layer material, a hole injection material, a hole transport material, an electron injection material, and the like according to their functions.
The light-emitting layer material may be classified into a polymer and a monomolecular according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons, a phosphorescent material derived from a triplet excited state of electrons, and a delayed fluorescent material derived from electron transfer from a triplet excited state to a singlet excited state according to a light-emitting mechanism, and the light-emitting layer material may be classified into blue and green light-emitting materials, and yellow and vermilion light-emitting materials required for realizing a natural color more excellent than that of a red light-emitting material according to light-emitting colors.
In addition, in order to improve color purity and luminous efficiency by energy transfer, a host/dopant substance may be used as the light-emitting substance. The principle is that a dopant, which is a light-emitting substance having an energy band gap smaller than that of the host, is mixed into the light-emitting layer in a small amount, so that excitons generated in the host are transferred to the dopant and light is emitted. By the principle as described above, light of a desired wavelength can be obtained depending on the types of the host and the dopant.
In addition, the efficiency of an organic light emitting element can be generally classified into internal light emitting efficiency and external light emitting efficiency. The internal light emission efficiency is related to the efficiency of generating excitons and realizing light conversion in an organic layer interposed between the 1 st electrode and the 2 nd electrode, such as a hole transport layer, a light emitting layer, and an electron transport layer, and theoretically, the internal light emission efficiency of fluorescence is 25% and phosphorescence is 100%.
In addition, the external light emission efficiency refers to the efficiency with which light generated in the organic layer is extracted to the outside of the organic light emitting element, and it has been known that about 20% of the internal light emission efficiency can be extracted to the outside. As a method for improving external light emission efficiency, various organic compounds having a high refractive index are generally used as a material of a cover layer in order to prevent loss of light irradiated to the outside due to total reflection, and efforts have been made up until now to develop an organic compound having a high refractive index and thin film stability capable of improving external light emission efficiency.
Documents of the prior art
Patent document
(patent document 1) Korean laid-open patent No. 10-2004-0098238
Disclosure of Invention
The purpose of the present invention is to provide an organic light-emitting element which can improve the absorption intensity in the ultraviolet region and realize high efficiency, high color purity, and long life in all regions of blue, green, and red by using, as a material for a cover layer, a compound having a difference between the refractive index at 450nm and the refractive index at 530nm of more than 0.15, and optionally a refractive index at 450nm of 2.26 or more and an attenuation coefficient value at 430nm of 0.10 or less.
As a means for solving the above-mentioned problems,
an embodiment of the present invention provides an organic light emitting device including a capping layer, the capping layer including a compound having a refractive index difference of more than 0.15 between a refractive index at 450nm and a refractive index at 530 nm. Specifically, the difference between the refractive index of the compound at 450nm and the refractive index at 530nm may be 0.16 or more.
Further, the refractive index of the above compound at 450nm may be 2.26 or more, and the attenuation coefficient value at 430nm may be 0.10 or less. Specifically, the refractive index of the above-mentioned compound at 450nm may be 2.28 or more, and the attenuation coefficient value at 430nm may be 0.10 or less, more specifically, the refractive index of the above-mentioned compound at 450nm may be 2.30 or more, and the attenuation coefficient value at 430nm may be 0.10 or less.
Further, the above-mentioned compound may have an attenuation coefficient value at 450nm of less than 0.01, and an attenuation coefficient value at 380nm of more than 0.5.
Further, the above compound may include one or more tertiary amine structures.
Further, the thickness of the above-mentioned cover layer may be 100 to
Figure BDA0002666797580000043
The organic light emitting element may include a1 st electrode and a 2 nd electrode, and 1 or more blue light emitting layers may be included between the 1 st electrode and the 2 nd electrode.
Another embodiment of the present invention provides a compound for a capping layer of an organic light emitting device, represented by the following chemical formula 1.
< chemical formula 1>
Figure BDA0002666797580000041
In the above-described chemical formula 1,
A. b, C are each independently a substituted or unsubstituted aryl group having C6-C50, or a substituted or unsubstituted heteroaryl group having C2-C50, A, B, C is represented by one or more of the following chemical formulae 1-1, 1-2, or 1-3,
L1to L3Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted arylene groupThe heteroarylene group of C2 to C50.
< chemical formula 1-1>
Figure BDA0002666797580000042
< chemical formula 1-2>
Figure BDA0002666797580000051
< chemical formula 1-3>
Figure BDA0002666797580000052
In the above chemical formula 1-1, chemical formula 1-2 or chemical formula 1-3,
x is independently C, CR, N, O, S, NR or CRR ', wherein R and R' are independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 mercapto, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl.
Specifically, the compound for a cover layer may be any of the following compounds.
Figure BDA0002666797580000061
According to the organic light emitting element including the capping layer of the embodiment of the invention, high efficiency and high color purity can be achieved and the service life can be prolonged by controlling the refractive index and the attenuation coefficient of the capping layer.
Specifically, by using a compound having a difference of more than 0.15 between the refractive index at 450nm and the refractive index at 530nm as the material of the cover layer, it is possible to enlarge the absorption wavelength of the ultraviolet region and thereby improve the lifetime when exposed to external ultraviolet rays.
Further, it is possible to enhance the light extraction effect and thereby achieve a high efficiency effect by using a high refractive index compound having a refractive index of 2.26 or more at 450nm as a material of the cover layer.
Further, it is possible to minimize the absorption wavelength in the blue visible region and thereby achieve high color purity by using a compound having an attenuation coefficient k of 0.10 or less at 430nm as a material of the cover layer.
In addition, it is possible to maintain a lower deposition temperature and form a higher glass transition temperature (Tg) by using a compound having a condensed ring and one tertiary amine group as a material of the capping layer, thereby improving thermal stability of the compound when performing deposition engineering.
Next, the effects described above and the additional effects will be described in detail.
Drawings
Fig. 1 is a sectional view schematically illustrating the configuration of an organic light emitting element according to an embodiment of the present invention.
[ notation ] to show
100: substrate
200: hole injection layer
300: hole transport layer
400: luminescent layer
500: electron transport layer
600: electron injection layer
1000: 1 st electrode
2000: 2 nd electrode
3000: covering layer
Detailed Description
Before explaining the present invention in detail, it is to be understood that the terminology used in the description is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention which will be limited only by the scope of the appended claims. Unless otherwise specifically stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.
Throughout this specification and the claims which follow, unless the context clearly dictates otherwise, the word "comprise", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated item, step, or series of items or steps but not the exclusion of any other item, step, or series of items or steps.
Throughout this specification and the claims, the term "aryl" is meant to include, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylene, phenylene, perylene, and,
Figure BDA0002666797580000091
Fluoro, fluoranthenyl, benzofluorenyl, benzotrriphenylene, benzo
Figure BDA0002666797580000092
Aryl group of C5-50 including aromatic ring such as pyrrolyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, quinolyl, isoquinolyl, quinoxalyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and a group consisting of pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, diazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrryl ring
Figure BDA0002666797580000093
An alkyl ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring,
Figure BDA0002666797580000094
An azolyl ring,
Figure BDA0002666797580000095
Diazole ring, benzo
Figure BDA0002666797580000096
And a heterocyclic group comprising an azole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a benzotriazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring or the like, and an aromatic ring having a carbon number of 3-50 and containing one or more hetero elements.
Throughout the present specification and claims, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen, amino group, nitro group, nitrile group, or alkyl group of C1 to C30, alkenyl group of C2 to C30, alkoxy group of C1 to C30, cycloalkyl group of C3 to C20, heteroalkyl group of C3 to C20, aryl group of C6 to C30, heteroaryl group of C3 to C30, and the like. In addition, throughout the specification of the present application, the same symbols have the same meaning unless explicitly stated otherwise.
Moreover, various embodiments of the invention may be combined with other certain embodiments, unless explicitly stated to the contrary. Next, embodiments of the present invention and effects thereof will be explained.
An organic light emitting element according to an embodiment of the present invention includes: 1 or more organic layers formed between the 1 st and 2 nd electrodes; and a cover layer formed on one side surface of the 1 st electrode and the 2 nd electrode and on one or more side surfaces opposite to the organic layer; the organic light-emitting element of (1), wherein the covering layer of the present invention may comprise a compound having a difference of more than 0.15 in refractive index at 450nm from that at 530 nm.
The compound as described above has a higher refractive index in the blue region, so that the efficiency of the organic light emitting element can be more effectively improved.
Specifically, the difference between the refractive index of the compound at 450nm and the refractive index at 530nm may be 0.16 or more, more specifically, 0.17 or more. Thereby, it is possible to enlarge the absorption wavelength of the ultraviolet region and thereby improve the life span when exposed to external ultraviolet rays.
Further, the refractive index of the above compound at 450nm may be 2.26 or more, and the attenuation coefficient value at 430nm may be 0.10 or less.
Specifically, the refractive index of the above compound at 450nm may be 2.28 or more, and the attenuation coefficient value at 430nm may be 0.10 or less.
More specifically, the above-mentioned compound may have a refractive index of 2.30 or more at 450nm and an attenuation coefficient value of 0.10 or less at 430nm, and the above-mentioned compound may minimize absorption in a visible ray region while having a higher refractive index, so that efficiency and color purity of the organic light emitting element may be more effectively improved.
By using a compound satisfying the above conditions as a material of the capping layer, it is possible to enhance light extraction efficiency and obtain a high-efficiency organic light emitting element, and it is also possible to minimize an absorption wavelength in a blue visible light region and thereby achieve high color purity.
Further, the above compound may have an attenuation coefficient value at 450nm of less than 0.01. By satisfying the above range, it is possible to minimize the absorption wavelength in the blue visible region and thereby achieve higher color purity.
Further, the above compound may have an attenuation coefficient value at 380nm of more than 0.5. By satisfying the above range, it is possible to enhance the absorption intensity in the ultraviolet region and thereby realize an element more stable when exposed to external ultraviolet rays.
The present invention also provides a compound for a cover layer, which has one or more tertiary amine structures, as a compound for a cover layer that can be used as a material for the cover layer. Specifically, the compound for an overcoat layer may have a tertiary amine structure.
By using the compound for a capping layer of the present invention as described above, it is possible to maintain a lower deposition temperature and form a higher glass transition temperature (Tg), thereby improving thermal stability of the compound when performing deposition engineering.
Specific examples of the compound for a cover layer of the present invention include compounds for a cover layer represented by the following chemical formula 1.
< chemical formula 1>
Figure BDA0002666797580000111
In the above-described chemical formula 1,
A. b, C are each independently a substituted or unsubstituted aryl group of C6 to C50, or a substituted or unsubstituted heteroaryl group of C2 to C50,
A. b, C is represented by the following chemical formula 1-1, chemical formula 1-2 or chemical formula 1-3,
L1to L3Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50.
< chemical formula 1-1>
Figure BDA0002666797580000121
< chemical formula 1-2>
Figure BDA0002666797580000122
< chemical formula 1-3>
Figure BDA0002666797580000123
In the above chemical formula 1-1, chemical formula 1-2 or chemical formula 1-3,
x are each, independently of one another, C, CR, N, O, S, NR or CRR',
r and R' are respectively and independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 sulfydryl, substituted or unsubstituted C6-C50 aryl or substituted or unsubstituted C2-C50 heteroaryl.
As a specific example, two or more of A, B, C of chemical formula 1 may be represented by the following chemical formula 1-1, chemical formula 1-2, or chemical formula 1-3. The compound of the present invention as described above has two or more condensed aryl groups, and thus can effectively improve the refractive index.
As a specific example, one or more of A, B, C of chemical formula 1 may be represented by chemical formula 1-1 below. The compounds of the present invention as described above may have a high refractive index although they have a low molecular weight.
As a specific example, the above chemical formula 1-1 may be a substituted or unsubstituted naphthyl group. The compound of the present invention as described above can minimize absorption in the visible light region and thereby achieve high color purity by including one or more non-polar substituents, i.e., naphthyl group.
Specific examples of the compound for a cover layer of the present invention include the following compounds for a cover layer.
Figure BDA0002666797580000141
Next, an organic light emitting element according to an embodiment of the present invention will be described in detail.
In one embodiment of the present invention, the organic light emitting device may include a1 st electrode, a 2 nd electrode, an organic layer interposed between the 1 st electrode and the 2 nd electrode, and a cover layer, and the cover layer may be disposed outside one or more of the 1 st electrode and the 2 nd electrode.
Among both side surfaces of the 1 st electrode or the 2 nd electrode, a side adjacent to the organic layer interposed between the 1 st electrode and the 2 nd electrode is referred to as an inner side, and a side not adjacent to the organic layer is referred to as an outer side. That is, when the capping layer is disposed outside the 1 st electrode, the 1 st electrode will be interposed between the capping layer and the organic layer, and when the capping layer is disposed outside the 2 nd electrode, the 2 nd electrode will be interposed between the capping layer and the organic layer.
In one embodiment of the present invention, the organic light emitting element may include a plurality of organic layers of 1 layer or more on the inner sides of the 1 st electrode and the 2 nd electrode, and a cover layer may be formed on the outer side of one or more of the 1 st electrode and the 2 nd electrode. That is, the cover layer may be formed on the outer side of the 1 st electrode and the outer side of the 2 nd electrode at the same time, or may be formed only on the outer side of the 1 st electrode or the outer side of the 2 nd electrode.
The coating layer may contain the coating layer compound of the present invention, may contain the coating layer compound of the present invention alone, or may contain two or more kinds of known compounds.
The organic layer may include a hole transport layer, a light emitting layer, and an electron transport layer, which generally constitute the light emitting section, but is not limited thereto.
Specifically, the organic light emitting element according to an embodiment of the present invention may include 1 or more organic layers constituting a light emitting portion such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL) between a1 st electrode (anode) and a 2 nd electrode (cathode).
Fig. 1 is a sectional view schematically illustrating the configuration of an organic light emitting element according to an embodiment of the present invention. An organic light emitting element according to an embodiment of the present invention may be manufactured in a structure as shown in fig. 1.
The organic light emitting element may be formed by sequentially stacking a substrate 100, a capping layer 3000, a1 st electrode 1000, a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, an electron injection layer 600, a 2 nd electrode 2000, and a capping layer 3000 in this order from below.
As the substrate 100, a substrate generally used for an organic light-emitting element can be used, and in particular, a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, handling convenience, and water resistance can be used.
The 1 st electrode 1000 is used as a hole injection electrode for injecting holes in the organic light emitting device. The 1 st electrode 1000 is manufactured using a material having a low work function to inject holes, and may be formed of a transparent material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or graphene (graphene).
The hole injection layer 200 may be formed by depositing a hole injection layer material on the 1 st electrode 1000 by a method such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, or the like. When the hole injection layer 200 is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the desired structure and thermal characteristics of the hole injection layer 200, and the deposition temperature of 50 to 500 ℃ and the deposition temperature of 10 ℃ may be generally used-8To 10-3Vacuum degree of torr (torr) of 0.01 to
Figure BDA0002666797580000171
Deposition rate per second and
Figure BDA0002666797580000172
the layer thickness is suitably selected within the range of 5 μm. Further, a charge generation layer may be additionally deposited on the surface of the hole injection layer 200 as needed. As the charge generation layer material, a general material, for example, hexacyano-Hexaazatriphenylene (HATCN) can be used.
Next, the hole transport layer 300 may be formed by depositing a hole transport layer material on the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a casting method, or a langmuir-blodgett (LB) method. In the case of forming the hole transport layer 300 by the above-described vacuum deposition method, the deposition conditions thereof will vary depending on the compound used, but are generally selected within the range of conditions almost the same as those for forming the hole injection layer 200. The hole transport layer 300 can be formed using a known compound. The hole transport layer 300 may be 1 or more layers as described above, and although not shown in fig. 1, an emission assist layer may be additionally formed on the hole transport layer 300.
The light emitting layer 400 can be formed by depositing a light emitting material on the hole transport layer 300 or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a casting method, or a langmuir-blodgetta (LB) method. When the light-emitting layer 400 is formed by the vacuum deposition method, the deposition conditions may vary depending on the compound used, but are generally selected within the range of conditions almost the same as those for forming the hole-injecting layer 200. As the material of the light-emitting layer, a known compound can be used as a host or a dopant.
In addition, when a phosphorescent dopant is simultaneously used in the material of the light emitting layer, a hole blocking material (HBL) may be additionally stacked on the upper portion of the light emitting layer 400 by a vacuum deposition method or a spin coating method in order to prevent a phenomenon that triplet excitons or holes are diffused into the electron transporting layer 500. The hole-blocking material used in this case is not particularly limited, and any known material can be selected and used. For example, it is possible to use
Figure BDA0002666797580000181
Oxadiazole derivatives, benzotriazole derivatives, phenanthroline derivatives, or the hole-blocking materials described in Japanese unexamined patent publication No. 11-329734(A1), and the most typical examples thereof include Balq (bis (8-hydroxy-2-methylquinoline) - (4-phenylphenoxy) aluminum), phenanthroline compounds (e.g., BCP (bathocuproine) available from UDC). The light emitting layer 400 of the present invention as described above may include 1 or more or 2 or more blue light emitting layers.
The electron transport layer 500 is formed on the light emitting layer 400, and may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. The deposition conditions of the electron transport layer 500 will vary depending on the compound used, but are generally selected to be within almost the same range as the conditions for forming the hole injection layer 200.
The electron injection layer 600 may be formed by depositing an electron injection layer material on the electron transport layer 500, and may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.
The hole injection layer 200, the hole transport layer 300, the light-emitting layer 400, and the electron transport layer 500 of the organic light-emitting device can be produced using the following materials, but are not limited thereto.
Figure BDA0002666797580000191
The 2 nd electrode 2000 is used as an electron injection electrode, and may be formed on the electron injection layer 600 by a vacuum deposition method, a spin coating method, or the like. As a material of the 2 nd electrode 2000, various metals can be used. As specific examples, substances such as aluminum, gold, silver, magnesium, and the like are included, but not limited thereto.
The organic light emitting device of the present invention may be an organic light emitting device having not only the above-described structure including the capping layer 3000, the 1 st electrode 1000, the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, the 2 nd electrode 2000, and the capping layer 3000, but also any of various structures, and may further include an intermediate layer including 1 or 2 layers as necessary.
Further, the thickness of each organic layer formed by the present invention may be adjusted as much as necessary, specifically, 10 to 1000nm, more specifically, 20 to 150 nm.
As shown in fig. 1, the cover layer 3000 may be formed on an outer surface of both side surfaces of the 1 st electrode 1000 on which the hole injection layer 200 is not formed. Further, the outer surface on which the electron injection layer 600 is not formed may be formed on both side surfaces of the 2 nd electrode 2000, but is not limited thereto. The capping layer 3000 as described above may be formed by deposition engineering, and the thickness of the capping layer 3000 may be 100 to 100 a
Figure BDA0002666797580000201
More specifically, it may be 300 to 300
Figure BDA0002666797580000202
Figure BDA0002666797580000203
The problem of the decrease in the transmittance of the cover layer 3000 can be prevented by the thickness adjustment method described above.
Although not shown in fig. 1, in one embodiment of the present invention, an organic layer for performing various functions may be additionally formed between the capping layer 3000 and the 1 st electrode 1000 or between the capping layer 3000 and the 2 nd electrode 2000. Alternatively, an organic material layer for performing various functions may be additionally formed on the upper portion (outer surface) of the cover layer 3000, but the present invention is not limited thereto.
Next, an organic light emitting element including a capping layer according to an embodiment of the present invention will be described in detail with reference to manufacturing examples and embodiments. The following production examples and examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following production examples and examples.
< production example 1> Synthesis of Compound 1
Figure BDA0002666797580000211
2- (4'-bromo- [1,1' -biphenyl) was charged in a round-bottomed flask]-4-yl) naphthalene (2- (4'-bromo- [1,1' -biphenyl)]-4-yl) naphthalene)3.0g, [1,1' -biphenyl]-4-amine ([1,1' -biphenyl)]-4-amine)1.4g、t-BuONa 1.2g、Pd2(dba)3 0.3g、(t-Bu)30.4ml of P was dissolved in 80ml of toluene, followed by stirring under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC) and was terminated after addition of water. The organic layer was extracted with MC and recrystallized after filtration under reduced pressure, thereby obtaining 3.6g of compound 1 (yield 60%).
m/z：725.31(100.0％)、726.31(61.4％)、727.31(18.2％)、728.32(3.6％)
< production example 2> Synthesis of Compound 2
Figure BDA0002666797580000221
Compound 2 was synthesized according to the same method as in preparation example 1, except that bis (4- (naphthalen-2-yl) phenyl) amine (bis (4- (naphthyl-2-yl) phenyl) amine) was used instead of [1,1'-biphenyl ] -4-amine ([1,1' -biphenyl ] -4-amine) (yield 65%).
m/z：699.29(100.0％)、700.30(58.8％)、701.30(17.0％)、702.30(3.2％)
< production example 3> Synthesis of Compound 3
Figure BDA0002666797580000222
The preparation was carried out in the same manner as in preparation example 1, wherein compound 3 was synthesized using 9- (4'-bromo- [1,1' -biphenyl ] -4-yl) phenanthrene (9- (4'-bromo- [1,1' -biphenyl ] -4-yl) phenanthrene) and bis (4- (naphthalen-2-yl) phenyl) amine (bis (4- (naphtalen-2-yl) phenyl) amine) in place of 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) naphthalene (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) phenalene) and [1,1'-biphenyl ] -4-amine ([1,1' -biphenyl ] -4-amine) (yield 61%).
m/z：749.31(100.0％)、750.31(63.5％)、751.31(19.6％)、752.32(4.0％)
< production example 4> Synthesis of Compound 4
Figure BDA0002666797580000231
The preparation was carried out in the same manner as in preparation example 1, except that 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) naphthalene (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) naphthalene and [1,1'-biphenyl ] -4-amine ([1,1' -biphenyl ] -4-yl) were replaced with 2-bromotriphenylene (2-bromotriphenylene) and 4'- (naphthalene-2-yl) - [1,1' -biphenyl ] -4-amine to synthesize compound 4 (yield 59%).
m/z：747.29(100.0％)、748.30(63.2％)、749.30(19.6％)、750.30(4.0％)
< production example 5> Synthesis of Compound 5
Figure BDA0002666797580000241
Compound 5 was synthesized in the same manner as in production example 1, except that 4- (naphthalen-2-yl) aniline (4- (naphthalen-2-yl) aniline) was used in place of [1,1'-biphenyl ] -4-amine ([1,1' -biphenyl ] -4-amine) (yield 63%).
m/z：775.32(100.0％)、776.33(65.4％)、777.33(21.0％)、778.33(4.4％)
Manufacture of organic light-emitting element
An organic light-emitting element was manufactured in the structure described in fig. 1, but a part of the layers was omitted as described below, and a cap layer 3000 was formed only on the upper portion. Specifically, the organic light emitting device is manufactured by sequentially laminating the 1 st electrode 1000, the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, the 2 nd electrode 2000, and the cover layer 3000 in this order from below. The substances shown in table 1 below were used for the hole injection layer 200, the hole transport layer 300, the light-emitting layer 400, and the electron transport layer 500.
[ TABLE 1 ]
Figure BDA0002666797580000251
< example 1> production of organic light-emitting element
Over an Indium Tin Oxide (ITO) substrate formed with a reflective layer containing Ag, a hole injection layer HI01 was formed
Figure BDA0002666797580000252
HATCN
Figure BDA0002666797580000253
Hole transport layer HT01
Figure BDA0002666797580000254
After the deposition, the light-emitting layer was doped with BH01: BD 013%
Figure BDA0002666797580000255
Film formation is performed. Next, as an electron transport layer, ET01: Liq (1:1)
Figure BDA0002666797580000256
Deposition of LiF after film formation
Figure BDA0002666797580000257
Figure BDA0002666797580000258
Thereby forming an electron injection layer. Next, MgAg was deposited to a thickness of 15nm to form a 2 nd electrode, and then the compound 1 produced in the above production example 1 was coated on the 2 nd electrode as a coating layer
Figure BDA0002666797580000259
Is deposited to a thickness of (a). The organic light-emitting element was manufactured by encapsulating (Encapsulation) the above-described element in a glove box.
< example 2 to example 5> production of organic light emitting element
The organic light-emitting element was produced by the same method as in example 1 above, and after the cover layer was formed using each of the compounds 2 to 5 produced in production examples 2 to 5, the organic light-emitting element was produced.
< comparative examples 1 to 3> production of organic light-emitting element
The organic light-emitting device was manufactured in the same manner as in example 1, and after the cover layer was formed using the compounds of comparative examples 1(ref.1) to 3(ref.3) represented by the following chemical formulas, respectively.
Figure BDA0002666797580000261
Figure BDA0002666797580000271
< test example 1> evaluation of refractive index and attenuation coefficient
Using the compounds 1 to 5 and the compounds of comparative examples 1(ref.1) to 3(ref.3) produced in the above process, a deposited film having a thickness of 30nm was produced on a silicon substrate using a vacuum deposition apparatus, and then refractive indices at 450nm, 530nm and attenuation coefficients at 430nm were measured using an ellipsometer apparatus (j.a. woollam co.inc, M-2000X). The results are shown in table 2 below.
[ TABLE 2 ]
Figure BDA0002666797580000272
As shown in Table 2, it was confirmed that the difference in refractive index between the compounds 1 to 5 of the present invention at 450nm and 530nm was more than 0.15, specifically 0.16 or more, more specifically 0.17 or more. Further, it was confirmed that the compounds 1 to 5 of the present invention exhibited high refractive indices of 2.26 or more at 450nm and had attenuation coefficient values of 0.10 or less at 430 nm.
< test example 2> evaluation of performance of organic light emitting element
The performance of the organic light emitting devices according to examples 1 to 5 and comparative examples 1 to 3, i.e., the current density and the luminance with respect to the applied voltage, were evaluated under atmospheric pressure conditions by applying a voltage to a gieviy 2400source measurement unit (kinetey 2400source measurement unit) to inject electrons and holes and measuring the luminance when light is emitted using a Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), and the results are shown in table 3.
[ TABLE 3 ]
Op.V mA/cm2 Cd/A CIEx CIEy LT97
Example 1 3.50 10 7.71 0.143 0.041 167
Example 2 3.50 10 7.70 0.143 0.041 170
Example 3 3.50 10 7.63 0.143 0.042 164
Example 4 3.50 10 7.52 0.143 0.042 155
Example 5 3.50 10 7.83 0.143 0.040 175
Comparative example 1 3.51 10 6.87 0.130 0.053 97
Comparative example 2 3.50 10 7.00 0.138 0.051 125
Comparative example 3 3.51 10 6.65 0.139 0.056 120
As shown in table 3, it was confirmed that the organic light-emitting devices of examples 1 to 5 of the present invention using compounds 1 to 5 of the present invention having a refractive index difference of more than 0.15 at 450nm and 530nm, a high refractive index of 2.26 or more and an attenuation coefficient value at 430nm of 0.10 or less were improved in efficiency, color purity and lifetime as compared with the comparative examples.

Claims (15)

1. An organic light-emitting element characterized in that:
is an organic light-emitting element including a covering layer,
the above-mentioned capping layer comprises a compound having a difference of more than 0.15 in refractive index at 450nm and 530 nm.
2. The organic light-emitting element according to claim 1, wherein:
the difference between the refractive index of the compound at 450nm and the refractive index at 530nm is more than 0.16.
3. The organic light-emitting element according to claim 1, wherein:
the compound has a refractive index at 450nm of 2.26 or more and an attenuation coefficient value at 430nm of 0.10 or less.
4. The organic light-emitting element according to claim 1, wherein:
the compound has a refractive index at 450nm of 2.28 or more and an attenuation coefficient value at 430nm of 0.10 or less.
5. The organic light-emitting element according to claim 1, wherein:
the compound has a refractive index at 450nm of 2.30 or more and an attenuation coefficient value at 430nm of 0.10 or less.
6. The organic light-emitting element according to claim 1, wherein:
the attenuation coefficient value of the compound at 450nm is less than 0.01.
7. The organic light-emitting element according to claim 1, wherein:
the above compound has an attenuation coefficient value at 380nm of more than 0.5.
8. The organic light-emitting element according to claim 1, wherein:
the above compounds include more than one tertiary amine structure.
9. The organic light-emitting element according to claim 1, wherein:
the thickness of the covering layer is 100 to
Figure FDA0002666797570000021
10. The organic light-emitting element according to any one of claims 1 to 9, wherein:
the organic light emitting element includes a1 st electrode and a 2 nd electrode,
the display device includes 1 or more blue light emitting layers between the 1 st electrode and the 2 nd electrode.
11. A compound for use in an overlay, characterized by:
is a compound for a cap layer of an organic light-emitting element,
represented by the following chemical formula 1,
< chemical formula 1>
Figure FDA0002666797570000031
In the above-described chemical formula 1,
A. b, C are each independently a substituted or unsubstituted aryl group having C6-C50, or a substituted or unsubstituted heteroaryl group having C2-C50, A, B, C is represented by one or more of the following chemical formulae 1-1, 1-2, or 1-3,
L1to L3Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50,
< chemical formula 1-1>
Figure FDA0002666797570000032
< chemical formula 1-2>
Figure FDA0002666797570000041
< chemical formula 1-3>
Figure FDA0002666797570000042
In the above chemical formula 1-1, chemical formula 1-2 or chemical formula 1-3,
x is independently C, CR, N, O, S, NR or CRR ', wherein R and R' are independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 mercapto, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl.
12. The compound for a cover layer according to claim 11, wherein:
two or more of A, B, C of chemical formula 1 are represented by chemical formula 1-1, chemical formula 1-2, or chemical formula 1-3.
13. The compound for a cover layer according to claim 11, wherein:
at least one of A, B, C in chemical formula 1 is represented by chemical formula 1-1.
14. The compound for a cover layer according to claim 11, wherein:
the above chemical formula 1-1 is a substituted or unsubstituted naphthyl group.
15. The compound for a cover layer according to claim 11, wherein:
the compound for a cover layer is any one of the following compounds,
Figure FDA0002666797570000051
Figure FDA0002666797570000061
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