CN113773318A - Novel compound for cover layer and organic light-emitting element comprising same - Google Patents
Novel compound for cover layer and organic light-emitting element comprising same Download PDFInfo
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Abstract
The present invention provides a compound for a capping layer represented by the following chemical formula 1 and an organic light emitting device including the same.<Chemical formula 1>
。
Description
Technical Field
The present invention relates to a compound for a cap layer and an organic light emitting device including the same.
Background
Materials used as an organic layer in an organic light-emitting element can be roughly classified into a light-emitting material, a hole-injecting material, a hole-transporting material, an electron-injecting material, and the like according to their functions.
The light-emitting materials may be classified into fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to the light-emitting mechanism, and may be classified into blue, green, and red light-emitting materials according to the emission color.
A general organic light emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. The hole transport layer, the light emitting layer, and the electron transport layer are organic thin films made of organic compounds.
The driving principle of the organic light emitting element structured as described above is as follows.
When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer via the hole transport layer, and electrons injected from the cathode move to the light-emitting layer via the electron transport layer. The holes and the electrons are recombined in the light-emitting layer to generate excitons.
Light is generated in the process of the above-described exciton being converted from the excited state to the ground state. 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 achieving light conversion in organic layers such as a hole transport layer, a light emitting layer, and an electron transport layer interposed between the 1 st electrode and the 2 nd electrode, 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 the light extraction efficiency, various organic compounds having a refractive index of 1.7 or more are generally used as a capping layer in order to prevent loss of light irradiated to the outside due to total reflection, and in order to improve the performance of an organic light emitting element, development of an organic compound having a high refractive index and thin film stability, which can improve the external light emission efficiency, has been conventionally conducted.
Disclosure of Invention
The present invention provides a compound for a cap layer of an organic light emitting element, which is an arylamine compound in which a hetero-bicyclic ring containing 1 or more nitrogen (N) is bonded to two amine cores in the form of indolizine or imidazopyridine, and which has a wide band gap in which absorption of visible light is difficult and a high refractive index, and which can increase the absorption wavelength in the ultraviolet region, thereby achieving high color purity, high efficiency, and a long lifetime, and an organic light emitting element including the compound for a cap layer.
Further, it is an object of the present invention to provide a compound for a capping layer and an organic light emitting device, which can improve a refractive index by optimizing an arrangement of a film between molecules, prevent recrystallization between molecules by a high glass transition temperature (Tg) and a high dew point temperature (Td), maintain a stable state of the film when heat is generated during driving, and improve stability by protecting a device from external air and moisture, thereby improving external quantum efficiency and remarkably improving a lifetime.
Next, the above-described problems and additional problems will be described in detail.
In order to solve the above-mentioned problems, in one embodiment of the present invention,
provided is a compound for a capping layer represented by the following chemical formula 1:
< chemical formula 1>
(in the above-mentioned chemical formula 1,
x1 to X7 are each independently C, CR or N, wherein R is each independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted alkyl group of C1 to C30, substituted or unsubstituted alkenyl group of C2 to C30, substituted or unsubstituted alkoxy group of C1 to C30, substituted or unsubstituted mercapto group of C1 to C30, substituted or unsubstituted aryl group of C6 to C50, or substituted or unsubstituted heteroaryl group of C2 to C50, adjacent R may form a ring or not by bonding with each other,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
l, L0 to L3 are each independently a directly bound, substituted or unsubstituted arylene of C6 to C50, or heteroarylene of C2 to C50).
In addition, in one embodiment of the present invention,
an organic light-emitting element containing the compound for a cap layer as described above is provided.
According to the compound for a cap layer of an embodiment of the present invention, an arylamine compound in which a heterobicyclic ring containing 1 or more nitrogen (N) in a form of indolizine or imidazopyridine, in which nitrogen (N) is required to be located at a specific position, is bonded to two amine cores can increase an absorption wavelength in an ultraviolet region while having a wide band gap and a high refractive index, in which absorption of visible light is difficult, and can realize an organic light-emitting device having high color purity, high efficiency, and a long lifetime when applied to a cap layer of an organic light-emitting device.
In addition, the refractive index can be improved by optimizing the film arrangement between molecules.
In addition, since it has a high glass transition temperature (Tg) and a high dew point temperature (Td), it is possible to prevent recrystallization between molecules and maintain a stable state of a thin film when heat is generated during driving of an organic light emitting element, and it is also possible to improve stability by protecting the element from external air and moisture, thereby improving external quantum efficiency and remarkably improving a lifetime.
Next, the effects described above and the additional effects will be described in detail.
Drawings
Fig. 1 is a schematic cross-sectional view of a layer structure of an organic light-emitting element according to an embodiment of the present invention.
FIG. 2 is a graph showing the measurement of the absorption wavelength in the range of 340nm to 460 nm.
[ 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 terms "comprise", "comprises", "comprising" and "comprising" are used merely to indicate the inclusion of a stated item, step or series of items or steps, and not to foreclose 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,
Fluoro, fluoranthenyl, benzofluorenyl, benzotrriphenylene, benzo
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
An alkyl ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, a derivative thereof, a salt thereof, a derivative thereof, a salt thereof, a derivative thereof, and a pharmaceutical composition comprising a compound thereof,
An azolyl ring,
A diazole ring, a benzofuran ring, a thiazole ringA C2-50 aromatic ring including at least one hetero element, a heterocyclic group consisting of a thiadiazole ring, a benzothiophene ring, a benzotriazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, and a dibenzofuran ring.
In addition, Ar in the formulax(wherein x is an integer) unless otherwise specifically defined, represents a substituted or substituted aryl group of C6 to C50, or a substituted or unsubstituted heteroaryl group of C2 to C50, Lx(wherein x is an integer) unless otherwise specifically defined, represents a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50, Rx(wherein, x is an integer) unless otherwise specifically defined, represents hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 mercapto group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2-C50 heteroaryl group.
Throughout the present specification and claims, the term "substituted or unsubstituted" may refer to a compound substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen, amino, cyano, nitrile, nitro, nitroso, sulfamoyl, isothiocyanate, thiocyanate, carboxyl, or C1-C30 alkyl, C1-C30 alkylsulfinyl, C1-C30 alkylsulfonyl, C1-C30 alkylsulfanyl, C1-C12 fluoroalkyl, C2-C30 alkenyl, C1-C30 alkoxy, C1-C12N-alkylamino, C2-C20N, N-dialkylamino, substituted or unsubstituted C1-C30 mercapto, C1-C6N-alkylsulfamoyl, C2-C12N, n-dialkyl sulfamoyl, silyl of C3-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C50, heteroaryl of C3-C50, 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.
The organic light emitting element according to an embodiment of the present invention may be an organic light emitting element including a capping layer. Specifically, the organic light emitting device may include a1 st electrode, a 2 nd electrode, 1 or more organic layers interposed between the 1 st electrode and the 2 nd electrode, and a cover layer disposed outside one or more of the 1 st electrode and the 2 nd electrode and containing the compound for a cover layer of the present invention.
Specific examples of the compound for a cap layer of the present invention include compounds for a cap layer represented by the following chemical formula 1.
< chemical formula 1>
In the above-described chemical formula 1,
x1 to X7 are each independently C, CR or N, wherein R is each independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted alkyl group of C1 to C30, substituted or unsubstituted alkenyl group of C2 to C30, substituted or unsubstituted alkoxy group of C1 to C30, substituted or unsubstituted mercapto group of C1 to C30, substituted or unsubstituted aryl group of C6 to C50, or substituted or unsubstituted heteroaryl group of C2 to C50, adjacent R may form a ring or not by bonding with each other,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
l, L0 to L3 are each independently a directly bound, substituted or unsubstituted arylene of C6 to C50, or heteroarylene of C2 to C50.
In the above, the substituent at the time of substitution may be deuterium, halogen, nitro, nitrile group, substituted or unsubstituted alkyl group of C1 to C30, substituted or unsubstituted alkenyl group of C2 to C30, substituted or unsubstituted alkoxy group of C1 to C30, substituted or unsubstituted mercapto group of C1 to C30, substituted or unsubstituted aryl group of C6 to C50, or substituted or unsubstituted heteroaryl group of C2 to C50.
Any one of the above X1 to X7 is C, and L is directly bonded to C.
The compound of the present invention represented by the above chemical formula 1, which is an arylamine compound in which a heterobicyclic ring containing 1 or more nitrogen (N) in a form of indolizine or imidazopyridine, in which the nitrogen (N) must be located at a specific position, is bonded to two amine cores, can increase the absorption wavelength in the ultraviolet region while having a wide band gap in which absorption of visible light is difficult and a high refractive index, and can realize an organic light-emitting device having high color purity, high efficiency, and a long lifetime. In addition, it is possible to optimize the inter-molecular thin film arrangement by minimizing the volume characteristic of the end portion of the aromatic amine and thereby improve the refractive index, and it is possible to prevent the inter-molecular recrystallization and maintain the stable state of the thin film when heat is generated during the driving of the organic light emitting element because of having a higher glass transition temperature (Tg) and a higher dew point temperature (Td), and it is also possible to improve the stability by protecting the element from the external air and moisture, thereby implementing the organic light emitting element in which the external quantum efficiency is improved and the lifetime is significantly improved.
As a specific example compound of the compound for a cap layer of the present invention, the above chemical formula 1 may include a compound for a cap layer represented by the following chemical formula 2 or chemical formula 3.
< chemical formula 2>
< chemical formula 3>
In the above chemical formula 2 and chemical formula 3,
definitions of X1 to X7, L, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1.
Any one of the above X1 to X7 is C, and L, L1 or L2 is directly bonded to C.
The compound for a cover layer of the present invention represented by chemical formula 2 or chemical formula 3 may effectively improve the refractive index even at a smaller molecular weight by including two or more hetero-bicyclic rings compared to chemical formula 1.
The two hetero-bicyclic rings may be bonded to two amine cores (N) respectively in a manner as shown in chemical formula 2, or may be simultaneously bonded to the same amine core (N) of the two in a manner as shown in chemical formula 3.
Further, as specific example compounds of the compound for a cover layer of the present invention, the above chemical formula 1 may include a compound for a cover layer represented by the following chemical formula 4.
< chemical formula 4>
In the above-mentioned chemical formula 4,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l is an integer of 0 to 5,
each m is independently an integer of 0 to 4.
Specifically, l may be an integer of 1 or more.
In the compound for a capping layer of the present invention represented by chemical formula 4, the hetero-bicyclic ring is bonded to the amine core (N) through direct bonding or through one or more phenylene groups, as compared to chemical formula 1, and thus, it is possible to minimize absorption in a long wavelength region while achieving a high refractive index.
Further, as a specific example compound of the compound for a cover layer of the present invention, the above chemical formula 1 may include a compound for a cover layer represented by the following chemical formula 5.
< chemical formula 5>
In the above-mentioned chemical formula 5,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l is an integer of 0 to 5,
each m is independently an integer of 0 to 4.
Specifically, l may be an integer of 1 or more.
The compound for a capping layer of the present invention represented by the above chemical formula 5 is bonded to the amine core (N) through direct bonding or through one or more 1, 4-phenylene groups, compared to the above chemical formula 1, and thus can improve stability upon exposure to external ultraviolet rays by increasing the absorption wavelength of the ultraviolet region while having a high refractive index.
Further, as specific exemplary compounds of the compound for a cover layer of the present invention, the above chemical formula 1 may include a compound for a cover layer represented by the following chemical formula 6 or the following chemical formula 7.
< chemical formula 6>
< chemical formula 7>
In the above chemical formula 6 and chemical formula 7,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l are each independently an integer of 0 to 5,
each m is independently an integer of 0 to 4.
Specifically, l may be an integer of 1 or more.
The compound for a capping layer of the present invention represented by chemical formula 6 or chemical formula 7 includes not only two or more hetero-bicyclic rings but also a structure in which the hetero-bicyclic rings are bonded to the amine core (N) through direct bonding or through one or more phenylene groups, as compared to chemical formula 1, and thus can minimize absorption in a long wavelength region while achieving a high refractive index.
The two hetero-bicyclic rings may be bonded to two amine cores (N), respectively, in a manner as shown in chemical formula 6, or may be simultaneously bonded to the same amine core (N) of the two in a manner as shown in chemical formula 7.
Further, as specific exemplary compounds of the compound for a cover layer of the present invention, the above chemical formula 1 may include a compound for a cover layer represented by the following chemical formula 8 or the following chemical formula 9.
< chemical formula 8>
< chemical formula 9>
In the above chemical formula 8 and chemical formula 9,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l are each independently an integer of 0 to 5,
each m is independently an integer of 0 to 4.
Specifically, l may be an integer of 1 or more.
The compound for a capping layer of the present invention represented by chemical formula 8 or 9 includes not only two or more hetero-bicyclic rings but also the hetero-bicyclic ring having a structure in which it is bonded to the amine core (N) through direct bonding or through one or more 1, 4-phenylene groups, as compared to chemical formula 1, and thus can have a high refractive index and improve stability upon exposure to external ultraviolet rays by increasing the absorption wavelength of the ultraviolet region.
The two hetero-bicyclic rings may be bonded to two amine cores (N), respectively, in a manner as shown in chemical formula 8, or may be simultaneously bonded to the same amine core (N) of the two in a manner as shown in chemical formula 9.
Further, in the above chemical formulas 1 to 9, L, L0 to L3 may each independently include phenylene, biphenylene, terphenylene, naphthylene, or a combination thereof. Although not limited, any one or more of L, L0 to L3 may be a1, 4-phenylene group, and specifically, L, L0 to L3 may be composed of one or more 1, 4-phenylene groups. In the case as described above, it is possible to have a lower deposition temperature while maintaining a high refractive index.
Further, in the above chemical formulas 1 to 9, X1 to X7 may each independently be C or CR. Wherein the definition of R is the same as that in the above chemical formula 1. Specifically, CR may be CH. Thereby, the volume characteristic can be reduced and the long wavelength absorption can be minimized.
In addition, in the above chemical formula 1 to the above chemical formula 9, any one or more of X1 to X7 may be N. This can realize a higher refractive index and can further effectively improve the absorption intensity in the ultraviolet region. Specifically, at least one of X1 and X3 may be N. More specifically, X1 may be N.
Further, in the above chemical formulas 1 to 9, X2 may be C. That is, by combining L, L1 to L3 at the X2 position of the hetero-bicyclic ring, the refractive index can be raised and the absorption intensity in the ultraviolet region can be raised.
In addition, in the above chemical formulas 1 to 9, Ar1 to Ar3 may each independently include phenyl, biphenyl, terphenyl, naphthyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenanthryl, triphenylene, or a combination thereof, and in the case of the above, volume characteristics may be minimized, and absorption in the ultraviolet region may be improved because the intermolecular film arrangement is excellent and may have a high refractive index.
In addition, when the above chemical formula 1 is represented by the following chemical formula 10, any one or more of A, Ar1, Ar2, Ar3 may include any one of the following chemical formulas a-1 to a-26. In the following chemical formulae a-1 to a-26, a is a binding site to which L, L1 to L3 bind.
< chemical formula 10>
In addition, in the above chemical formulas 1 to 9, any one or more of-L1-Ar 1, -L2-Ar 2, and-L3-Ar 3 may include any one selected from the following chemical formulas B-1 to B-8 or any one selected from the following chemical formulas B-1 to B-8.
In the above chemical formulae B-1 to B-8, q is each independently an integer of 0 to 3, and is a bonding site to the amine core (N).
By including the structures of the above chemical formulas B-1 to B-8, high refractive index, stability of the alignment of the intermolecular thin film, enhancement of absorption intensity in the ultraviolet region, and minimization of absorption in the blue region can be excellently achieved. Specifically, at least one of the groups-L1-Ar 1, -L2-Ar 2 and-L3-Ar 3 may be represented by the formula B-8.
Furthermore, in the above chemical formula 1 to the above chemical formula 9, the above L0 may include any one of the following chemical formulas C-1 to C-8.
In the above chemical formulae C-1 to C-8, q is each independently an integer of 0 to 4, and is a bonding site to the amine core (N).
Specifically, L0 may be of the formula C-1 above, in which case q may be 2 or 3.
The chemical formula 1 may be a compound for a cap layer represented by any one of the following compounds. The following compounds are merely illustrative of the present invention and the present invention is not limited thereto.
An example of the compound for a cover layer of the present invention can be synthesized by amination, and its general synthesis reaction formula is shown below.
< reaction formula 1>
< reaction formula 2>
< reaction formula 3>
In another embodiment of the present invention, there is provided an organic light-emitting element including a cap layer containing the compound for a cap layer as described above.
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, and 1 or more organic layers interposed between the 1 st electrode and the 2 nd electrode, and the cover layer may be disposed outside one or more of the 1 st electrode and the 2 nd electrode.
Specifically, the thickness of the cover layer may be 100 to 100
Further, the refractive index of the above-mentioned coating layer at 450nm may be 2.20 or more, specifically 2.25 or more, and the ultraviolet absorption intensity at 380nm may be 0.7 or more, specifically 0.8 or more.
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.
According to an embodiment of the present invention, the organic light emitting device 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 any 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.
Further, the above-mentioned coating layer may include the compound for coating layer according to the present invention, may include the compound for coating layer according to the present invention alone, or may include two or more or a combination 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.
As shown in fig. 1, the organic light emitting device may be formed by sequentially stacking a substrate 100, 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 bottom to top.
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 may 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 may be generally set to a deposition temperature of 50 to 500 ℃ and a deposition temperature of 10 ℃-8To 10-3Vacuum degree of torr (torr) of 0.01 to
Deposition rate per second and
the layer thickness range to 5 μm is suitably selected. 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
Examples of the most representative examples of the oxadiazole derivative, the benzotriazole derivative, the phenanthroline derivative, and the hole-blocking material described in Japanese patent application laid-open No. 11-329734(A1) include Balq (bis (8-hydroxy-2-methylquinoline) - (4-phenylphenoxy) aluminum), and phenanthroline compounds (e.g., BCP (bathocuproine) from UDC). The light-emitting layer 400 of the present invention 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 organic layers of the organic light emitting device, such as the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500, may be manufactured using known materials, but are not limited thereto.
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 various structures, 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, as described above, or may be an organic light emitting device including 1 or 2 additional intermediate layers, as necessary.
Further, the thickness of each organic layer formed by the present invention may be adjusted to a desired degree, specifically, 1 to 1000nm, more specifically, 1 to 100 nm.
The capping 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
More specifically, it may be 300 to 300
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, according to an 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 17
In a round-bottomed flask, 2.0g of 2- (4'-bromo- [1,1' -biphenyl)]-4-yl) indolizine (2- (4'-bromo- [1,1' -biphenyl)]-4-yl) indolizine), 1.2g of N4, N4'-diphenyl- [1,1' -biphenyl]-4,4' -diamine (N4, N4' -diphenyl- [1,1' -biphenyl)]-4,4' -diamine), 1.1g of t-BuONa, 0.3g of Pd2(dba)30.2ml of (t-Bu)3P was dissolved in 80ml of toluene and then stirred under reflux. The reaction was confirmed by Thin Layer Chromatography (TLC) and was terminated after the addition of water. The organic layer was extracted with dichloromethane (MC, methylene chloride) and recrystallized after filtration under reduced pressure, thereby obtaining 3.5g of compound 17 (yield 66%).
m/z：688.29(100.0％)、689.29(56.7％)、690.29(15.9％)、691.30(2.9％)
Production example 2: synthesis of Compound 53
Compound 53 was synthesized in the same manner as in preparation example 1, except that 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) imidazo [1,2-a ] pyridine (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) imidozo [1,2-a ] pyridine) was used instead of 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine). (yield 68%)
m/z：720.30(100.0％)、721.30(56.3％)、722.31(14.6％)、723.31(2.5％)、722.30(1.2％)
Production example 3: synthesis of Compound 65
The preparation was carried out in the same manner as in preparation example 1, except that 2- (4-bromophenyl) imidazo [1,2-a ] pyridine (2- (4-bromophenyl) imidozo [1,2-a ] pyridine) and N4, N4 "-diphenyl- [1,1':4', 1" -triphenyl ] -4,4 "-diamine (N4, N4" -diphenyl- [1,1':4',1 "-terphenyl ] -4, 4" -diamine) were used in place of 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine) and N4, N4'-diphenyl- [1,1' -biphenyl ] -4,4'-diamine (N4, N4' -diphenyl- [1,1'-biphenyl ] -4,4' -diamine) synthesized compound 65. (yield 63%)
m/z：796.33(100.0％)、797.33(62.8％)、798.34(18.3％)、799.34(4.0％)、798.33(1.4％)
Production example 4: synthesis of Compound 71
The preparation was carried out in the same manner as in preparation example 1, except that 2- (4-bromophenyl) imidazo [1,2-a ] pyridine (2- (4-bromophenyl) imidozo [1,2-a ] pyridine) and 4'- (naphthalen-2-yl) - [1,1' -biphenyl ] -4-amine (4'- (naphthalen-2-yl) - [1,1' -biphenyl ] -4-amine) were used instead of 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine) and bis (4- (naphthalen-2-yl) phenyl) amine (bis (4- (naphthalene-2-yl) phenyl) amine) to synthesize compound 71. (yield 66%)
m/z：720.30(100.0％)、721.30(56.3％)、722.31(14.6％)、723.31(2.5％)、722.30(1.2％)
Production example 5: synthesis of Compound 72
The production was carried out in the same manner as in production example 1, except that 2- (4-bromophenyl) imidazo [1,2-a ] pyridine (2- (4-bromophenyl) imidozo [1,2-a ] pyridine) and 4'- (imidazo [1,2-a ] pyridin-2-yl) - [1,1' -biphenyl ] -4-amine (4'- (imidozo [1,2-a ] pyrindin-2-yl) - [1,1' -biphenyl ] -4-amine) were used instead of 2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine (2- (4'-bromo- [1,1' -biphenyl ] -4-yl) indolizine) and bis (4- (naphthalen-2-yl) phenyl) amine (bis (4- (naphth-2-yl) phenyl) amine ) phenyl) amine) synthesized compound 72. (yield 61%)
m/z：796.33(100.0％)、797.33(62.8％)、798.34(18.3％)、799.34(4.0％)、798.33(1.4％)
Manufacture of organic light-emitting element
An organic light emitting element was manufactured in the structure shown in fig. 1. The organic light-emitting element is formed by sequentially stacking a substrate 100, an anode (hole injection 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 cathode (electron injection electrode 2000), and a cover layer 3000 in this order from bottom to top.
The compounds used in the organic layer located inside the electrode of the organic light-emitting element of the present invention are shown in table 1 below.
[ TABLE 1 ]
Example 1
Forming a hole injection layer on an Indium Tin Oxide (ITO) substrate having a reflective layer containing Ag
HI01,
And as a hole transport layer
HT01 (b), the light-emitting layer was prepared by doping BH01: BD 013%
The film of (1). Next, the film is formed as an electron transport layer
ET01 Liq (1:1) followed by deposition
The electron injection layer is formed. MgAg was then deposited in a thickness of 15nm, and the compound produced in production example 1 was then coated over the cathode as a coating layer
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.
Examples 2 to 5
The organic light emitting element was manufactured by performing the same manufacturing method as in example 1 above and forming the capping layer by deposition of the compounds manufactured by manufacturing examples 2 to 5, respectively.
Comparative examples 1 to 4
The fabrication was performed in the same manner as in example 1 above, in which the organic light-emitting element was fabricated by forming the capping layer by deposition using comparative compound 1(ref.1) to comparative compound 4(ref.4) shown in table 2 below, respectively.
[ TABLE 2 ]
<Test example 1>Evaluation of organic light-emitting element Performance
The performance of the organic light emitting devices according to examples 1 to 5 and comparative examples 1 to 4, 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 gievi 2400 source measurement unit (kiethly 2400 source 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 ]
| Classification | Op.V | mA/cm2 | Cd/A | CIEx | CIEy | LT97 |
| Example 1 | 3.48 | 10 | 7.49 | 0.139 | 0.044 | 160 |
| Example 2 | 3.48 | 10 | 7.60 | 0.140 | 0.044 | 171 |
| Example 3 | 3.48 | 10 | 7.70 | 0.140 | 0.044 | 180 |
| Example 4 | 3.49 | 10 | 7.65 | 0.139 | 0.045 | 175 |
| Example 5 | 3.48 | 10 | 7.73 | 0.140 | 0.044 | 183 |
| Comparative example 1 | 3.49 | 10 | 6.30 | 0.131 | 0.057 | 70 |
| Comparative example 2 | 3.48 | 10 | 6.94 | 0.136 | 0.050 | 105 |
| Comparative example 3 | 3.49 | 10 | 6.86 | 0.137 | 0.052 | 110 |
| Comparative example 4 | 3.49 | 10 | 6.52 | 0.133 | 0.055 | 88 |
As a result of comparison of examples of the present invention, it was found that the present invention can minimize the volume characteristics and have a high refractive index by combining a hetero-bicyclic ring such as imidazopyridine with an aromatic amine having two amine cores, while also increasing the absorption wavelength of the ultraviolet region and effectively improving the efficiency and lifetime of the organic light emitting element at a higher Tg, as compared to comparative example 1.
In addition, the present invention can minimize the volume characteristic of the core and improve the polarizability of the molecule by including the hetero-bicyclic ring in which nitrogen (N) is located at a specific position, and can form a stable thin film while improving the refractive index by an excellent thin film arrangement, thereby realizing an organic light emitting element of low driving voltage, high color purity, high efficiency, and long lifespan, as compared to comparative examples 2 to 4.
<Test example 2>Evaluation of refractive index
Using compound 17, compound 53, and compound 65 of the present invention produced through the above steps and comparative compound 1(ref.1) to comparative compound 4(ref.4) of table 2 described above, respectively, a deposited film having a thickness of 30nm was produced on a silicon substrate using a vacuum deposition apparatus, and then the refractive index at 450nm was measured using an ellipsometer apparatus (j.a. woollam co.inc, M-2000X). The results are shown in table 4 below.
[ TABLE 4 ]
As shown in table 4, it was confirmed that the refractive index of compound 17, compound 53 and compound 65 of the present invention was 2.20 or more, specifically 2.25 or more.
<Test example 3>Evaluation of absorption intensity in ultraviolet region
Using the compound 53 and the compound 65 of the present invention produced by the above procedure and the comparative compound 1(ref.1) and the comparative compound 3(ref.3) of the above table 2, respectively, a deposited film having a thickness of 30nm was produced on a silicon substrate by a vacuum deposition apparatus, and then an absorption wavelength at a wavelength of 340nm to 460nm was measured by an ellipsometer apparatus (j.a. woollam co.inc., M-2000X). The results are shown in FIG. 2.
When the absorption intensity of the compound 53 and the compound 65 of the present invention is 0.8 or more, specifically 0.9 or more in the ultraviolet absorption region of 380nm, it was confirmed that the absorption intensity was improved by 30% or more, specifically 50% or more, compared with the comparative compound 3 (ref.3).
Claims (23)
1. A compound for a capping layer represented by the following chemical formula 1:
chemical formula 1
In the above-described chemical formula 1,
x1 to X7 are each independently C, CR or N, wherein R is each independently hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted alkyl group of C1 to C30, substituted or unsubstituted alkenyl group of C2 to C30, substituted or unsubstituted alkoxy group of C1 to C30, substituted or unsubstituted mercapto group of C1 to C30, substituted or unsubstituted aryl group of C6 to C50, or substituted or unsubstituted heteroaryl group of C2 to C50, adjacent R may form a ring or not by bonding with each other,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
l, L0 to L3 are each independently a directly bound, substituted or unsubstituted arylene of C6 to C50, or heteroarylene of C2 to C50.
2. The compound for a cover layer according to claim 1, characterized in that:
the chemical formula 1 is represented by the following chemical formula 2 or the following chemical formula 3:
chemical formula 2
Chemical formula 3
In the above chemical formula 2 and chemical formula 3,
definitions of X1 to X7, L, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1.
3. The compound for a cover layer according to claim 1, characterized in that:
the chemical formula 1 is represented by the following chemical formula 4:
chemical formula 4
In the above-mentioned chemical formula 4,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l is an integer of 0 to 5,
each m is independently an integer of 0 to 4.
4. The compound for a cover layer according to claim 1, characterized in that:
the chemical formula 1 is represented by the following chemical formula 5:
chemical formula 5
In the above-mentioned chemical formula 5,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l is an integer of 0 to 5,
each m is independently an integer of 0 to 4.
5. The compound for a cover layer according to claim 1, characterized in that:
the chemical formula 1 is represented by the following chemical formula 6 or the following chemical formula 7:
chemical formula 6
Chemical formula 7
In the above chemical formula 6 and chemical formula 7,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l are each independently an integer of 0 to 5,
each m is independently an integer of 0 to 4.
6. The compound for a cover layer according to claim 1, characterized in that:
the chemical formula 1 is represented by the following chemical formula 8 or the following chemical formula 9:
chemical formula 8
Chemical formula 9
In the above chemical formula 8 and chemical formula 9,
the definitions of X1 to X7, L0 to L3, Ar1 to Ar3 are the same as those in the above chemical formula 1,
each definition of R1 is independently the same as that of R in the above chemical formula 1,
l are each independently an integer of 0 to 5,
each m is independently an integer of 0 to 4.
7. The compound for a cover layer according to claim 1, characterized in that:
each of the above X1 to X7 is independently C or CR.
8. The compound for a cover layer according to claim 7, wherein:
r in the above CR is hydrogen.
9. The compound for a cover layer according to claim 1, characterized in that:
any one or more of X1 to X7 is N.
10. The compound for a cover layer according to claim 1, characterized in that:
at least one of X1 and X3 is N.
11. The compound for a cover layer according to claim 1, characterized in that:
x2 represents C.
12. The compound for a cover layer according to claim 1, characterized in that:
each of the above L, L0 through L3 independently comprises phenylene, biphenylene, terphenylene, naphthylene, or combinations thereof.
13. The compound for a cover layer according to claim 1, characterized in that:
each of Ar1 through Ar3 described above independently includes phenyl, biphenyl, terphenyl, naphthyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenanthryl, triphenylene, or combinations thereof.
14. The compound for a cover layer according to claim 1, characterized in that:
when the chemical formula 1 is represented by the following chemical formula 10, any one or more of A, Ar1, Ar2, and Ar3 includes any one of the following chemical formulae A-1 to A-26:
chemical formula 10
15. The compound for a cover layer according to claim 1, characterized in that:
any one or more of the above-mentioned-L1-Ar 1, -L2-Ar 2 and-L3-Ar 3 includes any one selected from the following chemical formulae B-1 to B-8 or includes any one selected from the following chemical formulae B-1 to B-8:
in the above chemical formulae B-1 to B-8,
q is each independently an integer of 0 to 3.
16. The compound for a cover layer according to claim 15, wherein:
at least one of the above-mentioned-L1-Ar 1, -L2-Ar 2 and-L3-Ar 3 is represented by the above-mentioned chemical formula B-8.
17. The compound for a cover layer according to claim 1, characterized in that:
the above L0 includes any one of the following chemical formulas C-1 to C-8:
in the above chemical formulae C-1 to C-8,
q is each independently an integer of 0 to 4.
18. The compound for a cover layer according to claim 17, wherein:
l0 may be represented by the formula C-1, wherein q is 2 or 3.
19. The compound for a cover layer according to claim 1, characterized in that:
the above chemical formula 1 is any one of the following compounds:
20. an organic light-emitting element, comprising:
a cover layer comprising the compound for cover layer according to any one of claim 1 to claim 19.
21. The organic light-emitting element according to claim 20, wherein:
the organic light emitting element includes:
a1 st electrode and a 2 nd electrode; and the number of the first and second groups,
1 or more organic layers interposed between the 1 st electrode and the 2 nd electrode;
the cover layer is disposed outside one or more of the 1 st electrode and the 2 nd electrode.
22. The organic light-emitting element according to claim 20, wherein:
the thickness of the covering layer is 100 to
23. The organic light-emitting element according to claim 20, wherein:
the refractive index of the covering layer at a wavelength of 450nm is 2.20 or more.
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