CN113754618A - 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 PDF

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CN113754618A
CN113754618A CN202110625491.9A CN202110625491A CN113754618A CN 113754618 A CN113754618 A CN 113754618A CN 202110625491 A CN202110625491 A CN 202110625491A CN 113754618 A CN113754618 A CN 113754618A
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compound
cover layer
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咸昊完
安贤哲
金东骏
李东炫
闵丙哲
韩政佑
李萤振
安慈恩
权桐热
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Dongjin Semichem Co Ltd
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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>
Figure DDA0003100883950000011

Description

Novel compound for cover layer and organic light-emitting element comprising same
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 one or more fused rings of 4 or more rings are bonded to two amine cores, such as benzonaphthofuran, benzonaphthylthiophene, and the like, and which has a wide band gap in which a visible light region is hardly absorbed and a high refractive index, and which can increase the absorption wavelength in an 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 due to 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 of the organic light emitting device, and improve stability by protecting the 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>
Figure BDA0003100883930000031
< chemical formula 1-1>
Figure BDA0003100883930000041
< chemical formula 1-2>
Figure BDA0003100883930000042
(in the above chemical formula 1, chemical formula 1-1 and chemical formula 1-2,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
a is < chemical formula 1-1> or < chemical formula 1-2>,
x is O, S, Se, Te, NAr, CRR ', SiRR ' or GeRR ',
b is composed of a 5-membered ring, a 6-membered ring or a combination thereof,
r, R ', R1 and R2 are each 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, adjacent R and R', adjacent R1A plurality of adjacent R2May or may not form a ring by bonding to each other,
l1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50,
l and m are each independently an integer of 0 to 3,
position bound into N).
In addition, in one embodiment of the present invention,
an organic light-emitting element including a cap layer containing the above compound is provided.
According to the compound for a cap layer of an embodiment of the present invention, an arylamine compound in which 4 or more rings are fused into two amine cores in the form of, for example, benzonaphthofuran, benzonaphthylthiophene, or the like, 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 thus can realize an organic light-emitting device having high color purity, high efficiency, and long lifetime when applied to a cap layer of an organic light-emitting device.
In addition, it is possible to improve refractive index by optimizing the arrangement of the film between molecules, prevent recrystallization between molecules and maintain a stable state of the film when heat is generated during driving of the organic light emitting device because of having a higher glass transition temperature (Tg) and a higher dew point temperature (Td), and improve stability by protecting the device from external air and moisture, thereby improving external quantum efficiency and remarkably improving lifespan.
Next, the effects described above and the additional effects will be described in detail.
Drawings
Fig. 1 is a cross-sectional view schematically illustrating a layer structure of an organic light-emitting element.
FIG. 2 shows the results of measurement of absorption intensity in the wavelength 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 claims, the term "aryl" may be taken to include, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenylPhenanthryl, triphenylene, phenylene, or the like,
Figure BDA0003100883930000071
Fluoro, fluoranthenyl, benzofluorenyl, benzotrriphenylene, benzo
Figure BDA0003100883930000072
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 BDA0003100883930000073
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,
Figure BDA0003100883930000074
An azolyl ring,
Figure BDA0003100883930000075
And a heterocyclic group comprising a diazole ring, a benzofuran ring, a thiazole ring, a thiadiazole ring, a benzothiophene ring, a triazole 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 2-50 and containing one or more hetero elements.
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 explicitly defined otherwise, tablesThe aryl group is 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.
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>
Figure BDA0003100883930000091
< chemical formula 1-1>
Figure BDA0003100883930000101
< chemical formula 1-2>
Figure BDA0003100883930000102
In the above chemical formula 1, chemical formula 1-1 and chemical formula 1-2,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
a is a chemical formula 1-1 or a chemical formula 1-2,
x is O, S, Se, Te, NAr, CRR ', SiRR ' or GeRR ',
b is composed of a 5-membered ring, a 6-membered ring or a combination thereof,
r, R ', R1 and R2 are each 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, adjacent R and R', adjacent R, R 'and R' are not adjacent1A plurality of adjacent R2May or may not form a ring by bonding to each other,
l1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50,
l and m are each independently integers of 0 to 3, and are the positions bonded to N.
The compound represented by the above chemical formula 1, which is an arylamine compound in which 4 or more fused rings in the form of, for example, benzonaphthofuran, benzonaphthylthiophene, etc. are bonded to two amine cores, can increase the absorption wavelength in the ultraviolet region while having a wide band gap in which the visible light region is difficult to absorb and a high refractive index, and can realize an organic light-emitting element having high color purity, high efficiency, and 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 service life is remarkably improved.
Further, in chemical formula 1-1, the fused ring of 4 rings or more is fixed to the position shown in chemical formula 1-1 through the position where L2 is bonded to the amine core (N). The binding site as described above can optimize the molecular thin film arrangement of the compound of the present invention compared to other binding sites, and can increase the absorption wavelength of the ultraviolet region while having a high refractive index, thereby enabling an organic light-emitting element having high color purity, high efficiency, and long lifetime to be realized when applied to a cover layer.
Further, in chemical formula 1-2, the fused ring of 4 rings or more is fixed to the benzene ring position of the outer contour as shown in chemical formula 1-2 through the position where L2 is bonded to the amine core (N). The binding site as described above can optimize the molecular thin film arrangement of the compound of the present invention compared to the case of binding to an internal aromatic ring, and can raise the absorption wavelength of the ultraviolet region while having a high refractive index, thereby enabling realization of an organic light-emitting element having high color purity, high efficiency, and long life when applied to a cover layer.
As a specific example compound of the compound for a cap layer of the present invention, the chemical formula 1 may be represented by the following chemical formula 2 or the following chemical formula 3.
< chemical formula 2>
Figure BDA0003100883930000121
< chemical formula 3>
Figure BDA0003100883930000122
In the above chemical formula 2 and chemical formula 3,
the definitions of a are each independently the same as those in chemical formula 1 above, and the definitions of Ar1 to Ar3 and L1 are the same as those in chemical formula 1 above.
Further, A may be each independently the above chemical formula 1-1 or chemical formula 1-2, and may be the same or different from each other.
The compound for a cover layer of the present invention represented by chemical formula 2 or chemical formula 3 may more effectively improve the refractive index by including two fused rings having 4 or more rings than chemical formula 1.
The two fused rings of 4 or more rings may be respectively bound to two amine cores (N) in a manner as shown in chemical formula 2, or simultaneously bound to the same amine core (N) in a manner as shown in chemical formula 3.
Further, as a specific example compound of the compound for a cap layer of the present invention, the above chemical formula 1-1, which is an example of a in the above chemical formulae 1 to 3, may be represented by the following chemical formula 1-1-1, chemical formula 1-1-2, or chemical formula 1-1-3.
< chemical formula 1-1-1>
Figure BDA0003100883930000131
< chemical formula 1-1-2>
Figure BDA0003100883930000141
< chemical formulas 1-1-3>
Figure BDA0003100883930000142
In the above chemical formula 1-1-1, chemical formula 1-1-2 and chemical formula 1-1-3,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-1.
As shown in the above chemical formula 1-1-1, chemical formula 1-1-2 or chemical formula 1-1-3, when B in chemical formula 1-1 is the compound of the present invention having a 6-membered ring structure as A, the refractive index can be improved and the absorption in the visible ray region can be minimized. Specifically, the compound of the present invention may have formula 1-1-1, in which the 4-ring fused ring is located at a linear position with the amine core (N), as a.
Further, as specific exemplary compounds of the compound for a cap layer of the present invention, the above chemical formula 1-2, which is an exemplary a in the above chemical formulas 1 to 3, may be represented by the following chemical formula 1-2-1, chemical formula 1-2-2, or chemical formula 1-2-3.
< chemical formula 1-2-1>
Figure BDA0003100883930000151
< chemical formula 1-2-2>
Figure BDA0003100883930000152
< chemical formula 1-2-3>
Figure BDA0003100883930000153
In the above chemical formula 1-2-1, chemical formula 1-2-2, and chemical formula 1-2-3,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-2.
As shown in the above chemical formula 1-2-1, chemical formula 1-2-2 or chemical formula 1-2-3, when the compound of the present invention having a structure in which B in chemical formula 1-2 is a 6-membered ring is used as A, the refractive index can be improved and the absorption in the visible ray region can be minimized.
Further, the above chemical formula 1-2-1 may be represented by the following chemical formula 1-2-4. The compound of the present invention having chemical formula 1-2-4 in which the 4-ring condensed ring and the amine core (N) are located at an absolutely linear position by fixing the binding position as described above as a can have a higher refractive index.
< chemical formula 1-2-4>
Figure BDA0003100883930000161
In the above chemical formulas 1-2-4,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-2.
Further, as a specific example compound of the compound for a cover layer of the present invention, the above chemical formula 1 may be represented by the following chemical formula 4, chemical formula 5 or chemical formula 6. Specifically, the chemical formula 2 may be represented by chemical formula 4 or chemical formula 5, and the chemical formula 3 may be represented by chemical formula 6.
< chemical formula 4>
Figure BDA0003100883930000171
< chemical formula 5>
Figure BDA0003100883930000172
< chemical formula 6>
Figure BDA0003100883930000181
In the above chemical formulas 4 to 6,
ar1 to Ar3 and L1 are as defined in the above chemical formula 1,
the definitions of X, R1, R2, l, and m are each independently the same as those in chemical formula 1 above.
In the compound for a cover layer of the present invention represented by any one of chemical formulas 4 to 6 described above, by allowing the specific 4-ring and the amine (N) to be bound to a linear position, it is possible to significantly improve the absorption intensity in the ultraviolet region while having a high refractive index.
In addition, in the above chemical formulas 1 to 6, the above X may each independently be O or S. The compound of the present invention as described above can minimize the volume characteristics of the core, and can have a high refractive index in spite of its low molecular weight, and thus is excellent in thermal stability upon deposition. In addition, when X is O, the deposition temperature may be lowered.
In addition, in the chemical formulas 1 to 6, the R1 and R2 may be hydrogen. The compound of the present invention as described above can minimize pi-conjugation of the substituent, thereby minimizing absorption in the visible ray region.
In addition, in the above chemical formulas 1 to 3, the above L2 may each independently be a direct bond, phenylene, biphenylene, or a combination thereof, and specifically may be a direct bond. The compound of the present invention as described above can minimize pi conjugation of the amine linker, thereby minimizing absorption in the visible ray region, and can effectively improve refractive index.
In addition, in the above chemical formulas 1 to 6, the above L1 may be p-phenylene (p-phenylene), p-biphenylene (p-biphenylene), p-terphenylene (p-terphenylene), naphthylene (naphthylene), pyridylene (pyridylene), dibenzofuranylene (dibenzofuranylene), dibenzothiophenylene (dibenzothiophenylene), dimethylfluorenyl (dimethylfluorrylene), carbazolyl (carbazolyl) or a combination thereof. The compound of the present invention as described above can have a higher refractive index and can more effectively enhance the absorption intensity in the ultraviolet region. Specifically, the L1 may be a terphenylene group. In the present specification, p-phenylene means 1, 4-phenylene, p-biphenylene means biphenylene in which two 1, 4-phenylenes are linked, and p-terphenylene means terphenylene in which 3 1, 4-phenylenes are linked.
Further, in the above chemical formulas 1 to 6, the above Ar1 to Ar3 may each independently include the above a, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, or a combination thereof. The compound of the present invention as described above can minimize the volume characteristics of the substituents, thereby optimizing the inter-molecular thin film arrangement and thereby having a high refractive index, and can also minimize the absorption in the visible ray region.
In addition, in the above chemical formula 1 to the above chemical formula 3, the above a may be represented by any one of the following chemical formulas a-1 to a-14.
Figure BDA0003100883930000211
In the above chemical formulae A-1 to A-14,
x is O, S, N-Ph or CRR ', R and R' are as defined in the above chemical formula 1, and q are each independently an integer of 0 to 3.
In addition, in the chemical formulas 1 to 6, any one of the Ar1 to Ar3 may be represented by any one of the following chemical formulas B-1 to B-8.
Figure BDA0003100883930000221
In the above chemical formulas B-1 to B-8, q are each independently an integer of 0 to 3.
In addition, in the chemical formulas 1 to 6, the L1 may be represented by any one of the following chemical formulas C-1 to C-9.
Figure BDA0003100883930000231
In the above chemical formulas C-1 to C-9, q are each independently an integer of 0 to 4.
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.
Figure BDA0003100883930000241
Figure BDA0003100883930000251
Figure BDA0003100883930000261
Figure BDA0003100883930000271
Figure BDA0003100883930000281
Figure BDA0003100883930000291
Figure BDA0003100883930000301
Figure BDA0003100883930000311
Figure BDA0003100883930000321
Figure BDA0003100883930000331
Figure BDA0003100883930000341
Figure BDA0003100883930000351
Figure BDA0003100883930000361
Figure BDA0003100883930000371
Figure BDA0003100883930000381
Figure BDA0003100883930000391
Figure BDA0003100883930000401
Figure BDA0003100883930000411
Figure BDA0003100883930000421
Figure BDA0003100883930000431
Figure BDA0003100883930000441
Figure BDA0003100883930000451
Figure BDA0003100883930000461
Figure BDA0003100883930000471
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>
Figure BDA0003100883930000481
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 an 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 a cover layer, 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
Figure BDA0003100883930000491
Further, the refractive index of the above-mentioned cover layer at a wavelength of 450nm may be 2.20 or more, specifically 2.25 or more, more specifically 2.30 or more, and the ultraviolet absorption intensity at a wavelength of 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
Figure BDA0003100883930000511
Deposition rate per second and
Figure BDA0003100883930000512
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 substance, general substances can be used, for examplehexacyano-Hexaazatriphenylene (HATCN) may 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 BDA0003100883930000521
Oxadiazole derivatives, benzotriazole derivatives, phenanthroline derivatives, or the hole-blocking materials described in Japanese patent application laid-open No. 11-329734(A1), and the like, and the most typical of these include Balq (bis (8-hydroxy-8-yl)-2-methylquinoline) - (4-phenylphenoxy) aluminum), phenanthrolines (phenanthrolines) class of compounds (for example: BCP (bathocuproine) by UDC corporation), and the like. 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, can be produced using known materials.
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 cover layer 3000 may be formed on the above-mentioned substrateThe 1 st electrode 1000 has an outer surface on both sides thereof 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 BDA0003100883930000541
More specifically, it may be 300 to 300
Figure BDA0003100883930000542
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 26
Figure BDA0003100883930000551
In a round-bottomed flask, 2.0g of 3-bromonaphtho [2,3-b ]]Benzofuran (3-bromounapthho [2,3-b ]]benzofuran), 1.1g of N4, N4'-diphenyl- [1,1' -biphenyl]-4,4' -diamine (N4, N4' -diphenyl- [1,1' -biphenyl)]-4,4' -diamine), 1.0g of t-BuONa, 0.3g of Pd2(dba)30.2ml of (t-Bu)3After dissolving P in 70ml of tolueneReflux stirring was performed. 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, methyl chloride) and recrystallized after filtration under reduced pressure, thereby obtaining 3.50g of compound 26 (yield 69%).
m/z：768.28(100.0％)、769.28(61.1％)、770.28(18.9％)、771.29(3.8％)
Production example 2: synthesis of Compound 39
Figure BDA0003100883930000561
Compound 39 was synthesized in the same manner as in preparation example 1, except that N4, N4 "-diphenyl- [1,1':4', 1" -triphenyl ] -4,4 "-diamine (N4, N4" -diphenyl- [1,1':4',1 "-terphenyl ] -4, 4" -diamine) was used in place of N4, N4'-diphenyl- [1,1' -biphenyl ] -4,4'-diamine (N4, N4' -diphenyl- [1,1'-biphenyl ] -4,4' -diamine). (yield 70%)
m/z：844.31(100.0％)、845.31(67.9％)、846.32(22.5％)、847.32(5.2％)
Production example 3: synthesis of Compound 45
Figure BDA0003100883930000571
Compound 45 was synthesized in the same manner as in preparation example 1, except that N4, N4-diphenyl- [1,1'-biphenyl ] -4,4' -diamine (N4, N4-diphenyl- [1,1'-biphenyl ] -4,4' -diamine) was used in place of N4, N4'-diphenyl- [1,1' -biphenyl ] -4,4'-diamine (N4, N4' -diphenyl- [1,1'-biphenyl ] -4,4' -diamine). (yield 67%)
m/z：768.28(100.0％)、769.28(61.1％)、770.28(18.9％)、771.29(3.8％)
Production example 4: synthesis of Compound 67
Figure BDA0003100883930000581
Compound 67 was synthesized in the same manner as in preparation example 1, except that 9-bromonaphtho [2,1-b ] benzofuran (9-bromonaphtho [1,2-b ] benzofurans) was used in place of 3-bromonaphtho [2,3-b ] benzofuran. (yield 66%)
m/z：768.28(100.0％)、769.28(61.1％)、770.28(18.9％)、771.29(3.8％)
Production example 5: synthesis of Compound 91
Figure BDA0003100883930000582
Compound 91 was synthesized in the same manner as in preparation example 1, except that 9-bromonaphtho [1,2-b ] benzofuran (9-bromonaphtho [1,2-b ] benzofurans) was used in place of 3-bromonaphtho [2,3-b ] benzofuran. (yield 65%)
m/z：768.28(100.0％)、769.28(61.1％)、770.28(18.9％)、771.29(3.8％)
Production example 6: synthesis of Compound 164
Figure BDA0003100883930000591
Compound 164 was synthesized by the same method as in preparation example 1, except that 3-bromobenzo [ b ] naphtho [2,3-d ] thiophene (3-bromobenzo [ b ] naphtho [2,3-d ] thiophene) was used in place of 3-bromonaphtho [2,3-b ] benzofuran (3-bromonaphtho [2,3-b ] benzofuran). (yield 68%)
m/z：800.23(100.0％)、801.24(61.0％)、802.24(18.3％)、802.23(10.5％)、803.23(5.6％)、803.24(4.0％)、801.23(2.3％)、804.23(1.8％)
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 ]
Figure BDA0003100883930000601
Example 1
Forming a hole injection layer on an Indium Tin Oxide (ITO) substrate having a reflective layer containing Ag
Figure BDA0003100883930000611
HI01,
Figure BDA0003100883930000612
And as a hole transport layer
Figure BDA0003100883930000613
HT01 (b), the light-emitting layer was prepared by doping BH01: BD 013%
Figure BDA0003100883930000614
The film of (1). Next, the film is formed as an electron transport layer
Figure BDA0003100883930000615
ET01 Liq (1:1) followed by deposition
Figure BDA0003100883930000616
The electron injection layer is formed. MgAg was then deposited at a thickness of 15nm and then produced in production example 1 above the cathode as a capping layerA compound of formula (I) and (II)
Figure BDA0003100883930000617
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 6
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 6, 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 ]
Figure BDA0003100883930000621
<Test example 1>Evaluation of organic light-emitting element Performance
The performance of the organic light emitting devices according to examples 1 to 6 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 7.81 0.143 0.044 161
Example 2 3.48 10 7.92 0.144 0.043 171
Example 3 3.48 10 7.88 0.144 0.043 167
Example 4 3.49 10 7.73 0.142 0.046 156
Example 5 3.49 10 7.70 0.142 0.046 152
Example 6 3.48 10 7.85 0.144 0.043 163
Comparative example 1 3.49 10 6.20 0.136 0.055 76
Comparative example 2 3.49 10 6.17 0.137 0.054 80
Comparative example 3 3.49 10 6.63 0.138 0.052 91
Comparative example 4 3.50 10 6.15 0.136 0.055 71
Comparing the examples of the present invention with the comparative examples, it can be seen that 4 or more fused rings in the form of, for example, benzonaphthofurans, benzonaphthylthiophenes, etc. are combined with an aromatic amine having two amine cores (N) in the present invention, and thus, compared with comparative examples 1 and 2 in which 3-ring fused rings are combined and comparative examples 3 and 4 in which 4-ring fused rings are combined but the combination position in which the fused ring is combined in an amine core (N) is different from that of the present invention, an organic light emitting element having high color purity, high efficiency, and long lifetime can be realized because the film arrangement of the molecules is excellent and the absorption wavelength of the ultraviolet region is increased while having a high refractive index.
<Test example 2>Evaluation of refractive index
Using compound 26, compound 39, compound 45, and compound 164 produced through the above steps and comparative compound 1(ref.1) to comparative compound 3(ref.3) of table 2, 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 a wavelength of 450nm was measured using an ellipsometer apparatus (j.a. woollam co.inc, M-2000X). The results are shown in table 4 below.
[ TABLE 4 ]
Figure BDA0003100883930000641
As shown in table 4 above, it was confirmed that the refractive indices of compound 26, compound 39, compound 45 and compound 164 were 2.25 or more, specifically 2.30 or more, more specifically 2.35 or more.
<Test example 3>Evaluation of absorption intensity in ultraviolet region
Using compound 26, compound 39, and compound 45 produced through the above procedure and comparative compound 1(ref.1) and comparative compound 3(ref.3) of table 2, respectively, a deposited film having a thickness of 30nm was produced on a silicon substrate using a vacuum deposition apparatus, and then an absorption wavelength at a wavelength of 340nm to 460nm was measured using an ellipsometer apparatus (j.a. woollam co.inc, M-2000X). The results are shown in FIG. 2.
When the absorption intensity of the compounds 26, 39 and 45 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, more specifically 50% or more in comparison with the comparative compounds 1(ref.1) and 3(ref.3), specifically in comparison with the comparative compound 3 (ref.3).

Claims (19)

1. A compound for a capping layer represented by the following chemical formula 1:
chemical formula 1
Figure FDA0003100883920000011
Chemical formula 1-1
Figure FDA0003100883920000012
Chemical formula 1-2
Figure FDA0003100883920000013
In the above chemical formula 1, chemical formula 1-1 and chemical formula 1-2,
ar1 to Ar3 are each independently substituted or unsubstituted aryl of C6 to C50, or substituted or unsubstituted heteroaryl of C2 to C50,
a is a chemical formula 1-1 or a chemical formula 1-2,
x is O, S, Se, Te, NAr, CRR ', SiRR ' or GeRR ',
b is composed of a 5-membered ring, a 6-membered ring or a combination thereof,
r, R ', R1 and R2 are each 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, adjacent R and R', adjacent R1A plurality of adjacent R2May or may not form a ring by bonding to each other,
l1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50,
l and m are each independently an integer of 0 to 3,
x is the position of binding into N.
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
Figure FDA0003100883920000021
Chemical formula 3
Figure FDA0003100883920000031
In the above chemical formula 2 and chemical formula 3,
each definition for a is independently the same as that in the above chemical formula 1,
definitions of Ar1 to Ar3 and L1 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 above chemical formula 1-1 is represented by the following chemical formula 1-1-1, chemical formula 1-1-2 or chemical formula 1-1-3:
chemical formula 1-1
Figure FDA0003100883920000032
Chemical formula 1-1-2
Figure FDA0003100883920000033
Chemical formula 1-1-3
Figure FDA0003100883920000041
In the above chemical formula 1-1-1, chemical formula 1-1-2 and chemical formula 1-1-3,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-1.
4. The compound for a cover layer according to claim 1, characterized in that:
the above chemical formula 1-2 is represented by the following chemical formula 1-2-1, chemical formula 1-2-2 or chemical formula 1-2-3:
chemical formula 1-2-1
Figure FDA0003100883920000042
Chemical formula 1-2
Figure FDA0003100883920000051
Chemical formula 1-2-3
Figure FDA0003100883920000052
In the above chemical formula 1-2-1, chemical formula 1-2-2, and chemical formula 1-2-3,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-2.
5. The compound for a cover layer according to claim 1, characterized in that:
the above chemical formula 1-2 is represented by the following chemical formula 1-2-4:
chemical formula 1-2-4
Figure FDA0003100883920000053
In the above chemical formulas 1-2-4,
the definitions of X, L2, R1, R2, l and m are the same as those in the above chemical formula 1-2.
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 4, chemical formula 5 or chemical formula 6:
chemical formula 4
Figure FDA0003100883920000061
Chemical formula 5
Figure FDA0003100883920000062
Chemical formula 6
Figure FDA0003100883920000071
In the above chemical formulas 4 to 6,
ar1 to Ar3 and L1 are as defined in the above chemical formula 1,
the definitions of X, R1, R2, l, and m are each independently the same as those in chemical formula 1 above.
7. The compound for a cover layer according to claim 1, characterized in that:
the above X is O or S.
8. The compound for a cover layer according to claim 1, characterized in that:
r1 and R2 are each hydrogen.
9. The compound for a cover layer according to claim 1, characterized in that:
the above L2 is a direct bond, phenylene, biphenylene or a combination thereof.
10. The compound for a cover layer according to claim 1, characterized in that:
l1 is p-phenylene, p-biphenylene, p-terphenylene, naphthylene, pyridinylene, dibenzofuranylene, dibenzothiophenylene, dimethylfluorenyl, carbazolyl, or a combination thereof.
11. The compound for a cover layer according to claim 1, characterized in that:
ar1 through Ar3 each independently include A, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, or combinations thereof, as described above.
12. The compound for a cover layer according to claim 1, characterized in that:
a is represented by any one of the following chemical formulae A-1 to A-14:
Figure FDA0003100883920000091
in the above chemical formulae A-1 to A-14,
x is O, S, N-Ph or CRR ', R and R' are as defined in the above chemical formula 1, and q are each independently an integer of 0 to 3.
13. The compound for a cover layer according to claim 1, characterized in that:
any one of the above Ar1 to Ar3 is represented by any one of the following chemical formulae B-1 to B-8:
Figure FDA0003100883920000101
in the above chemical formulae B-1 to B-8,
q is each independently an integer of 0 to 3.
14. The compound for a cover layer according to claim 1, characterized in that:
the above L1 is represented by any one of the following chemical formulae C-1 to C-9:
Figure FDA0003100883920000111
in the above chemical formulae C-1 to C-9,
q is each independently an integer of 0 to 4.
15. The compound for a cover layer according to claim 1, characterized in that:
the above chemical formula 1 is represented by any one of the following compounds:
Figure FDA0003100883920000121
Figure FDA0003100883920000131
Figure FDA0003100883920000141
Figure FDA0003100883920000151
Figure FDA0003100883920000161
Figure FDA0003100883920000171
Figure FDA0003100883920000181
Figure FDA0003100883920000191
Figure FDA0003100883920000201
Figure FDA0003100883920000211
Figure FDA0003100883920000221
Figure FDA0003100883920000231
Figure FDA0003100883920000241
Figure FDA0003100883920000251
Figure FDA0003100883920000261
Figure FDA0003100883920000271
Figure FDA0003100883920000281
Figure FDA0003100883920000291
Figure FDA0003100883920000301
Figure FDA0003100883920000311
Figure FDA0003100883920000321
Figure FDA0003100883920000331
Figure FDA0003100883920000341
Figure FDA0003100883920000351
16. an organic light-emitting element, comprising:
a cover layer comprising the compound for cover layer according to any one of claim 1 to claim 15.
17. The organic light-emitting element according to claim 16, 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.
18. The organic light-emitting element according to claim 16, wherein:
the thickness of the covering layer is 100 to
Figure FDA0003100883920000361
19. The organic light-emitting element according to claim 16, wherein:
the refractive index of the covering layer at a wavelength of 450nm is 2.25 or more.
CN202110625491.9A 2020-06-04 2021-06-04 Novel compound for cover layer and organic light-emitting element comprising same Pending CN113754618A (en)

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