CN114163337A - Compound for reflective electrode protection layer and back light-emitting element comprising same - Google Patents

Compound for reflective electrode protection layer and back light-emitting element comprising same Download PDF

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CN114163337A
CN114163337A CN202111063596.6A CN202111063596A CN114163337A CN 114163337 A CN114163337 A CN 114163337A CN 202111063596 A CN202111063596 A CN 202111063596A CN 114163337 A CN114163337 A CN 114163337A
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reflective electrode
compound
emitting element
protection layer
group
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咸昊完
安贤哲
金熙宙
金东骏
李东炫
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 reflective electrode protection layer of a back light emitting device represented by the following chemical formula 1.<Chemical formula 1>
Figure DDA0003257361000000011

Description

Compound for reflective electrode protection layer and back light-emitting element comprising same
Technical Field
The present invention relates to a compound for a reflective electrode protection layer and a back light emitting element 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.
In addition, the light emitting material may be classified into a fluorescent material derived from a singlet excited state of electrons, a phosphorescent material derived from a triplet excited state of electrons, and a delayed fluorescent material derived from electron movement from a triplet excited state to a singlet excited state according to a light emitting mechanism, and may be classified into blue, green, red, and yellow and vermilion light emitting materials required for realizing more excellent natural colors according to light emitting colors.
A general organic light-emitting element 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 will move to the light-emitting layer via the hole transport layer, and electrons injected from the cathode will move to the light-emitting layer via the electron transport layer. The holes and electrons recombine in the light-emitting layer and form excitons. Light is generated during the process of the exciton transforming from the excited state to the ground state.
In addition, the efficiency of an organic light emitting element can be generally classified into internal light emitting efficiency and external light emitting efficiency. The internal light emission efficiency is related to the efficiency of generating excitons and 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%.
For the front surface light emitting element as described above, there have been efforts to develop a cover material having a high refractive index for light extraction.
On the other hand, in the back light emitting element, the light reflected by the reflective cathode is emitted toward the driving thin film transistor, i.e., toward the transparent anode. In this case, Alq3 having excellent thermal stability is generally used as a protective film for protecting a reflective electrode which is likely to cause corrosion of an organic light emitting element, but since ash (ash) is generated during deposition to form an uneven protective film, a gap is formed between the electrode and the protective film, and moisture or oxygen penetrates, resulting in a short service life. In order to compensate for the above-mentioned disadvantages, a compound for an organic protective film is used as a material of the protective film, but in order to improve the service life of the back light emitting element which is gradually increased in size, there have been efforts to develop a compound for a reflective electrode protective film which can form a more uniform thin film, has a low deposition temperature, and has excellent thermal stability.
Disclosure of Invention
Accordingly, an object of the present invention is to provide a back light emitting device having a further improved lifetime by providing a protective layer which can protect the reflective electrode and the inside of the back light emitting device from moisture, oxygen, and external contamination, and which can form a uniform thin film and has excellent thermal stability.
Next, the above-described problems and additional problems will be described in detail.
As a means for solving the above-mentioned problems,
as an embodiment of the present invention, there is provided a compound for a reflective electrode protection layer of a back light-emitting element represented by the following chemical formula 1:
< chemical formula 1>
Figure BDA0003257360980000031
In the chemical formula 1, the first and second organic solvents,
Ar1to Ar4Each independently is a substituted or unsubstituted aryl group of C6-C50, or a substituted or unsubstituted heteroaryl group of C2-C50,
l is a substituted or unsubstituted arylene group having from C6 to C50 and consisting of 1 or 2 rings or a substituted or unsubstituted heteroarylene group having from C2 to C50 and consisting of 1 or 2 rings,
L1to L4Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50.
In addition, as an embodiment of the present invention,
provided is a back surface light emitting element including: a1 st electrode and a 2 nd reflective electrode; 1 or more organic layers interposed between the 1 st and 2 nd reflective electrodes; and a reflective electrode protection layer disposed outside the 2 nd reflective electrode, the reflective electrode protection layer containing the compound for reflective electrode protection layer.
The compound for a reflective electrode protection layer according to the present invention is a compound containing 2 arylamine groups in which the volume characteristics of a linker are minimized, can effectively improve the stability of an element under oxygen, moisture, and external contamination because the intermolecular thin film arrangement is excellent, and can suppress the generation of foreign substances at the time of deposition because the higher purity of the compound can be easily secured. In addition, since the extended form of the aryl, fused aryl or heteroaryl group is included to have a high glass transition temperature (Tg) and a high decomposition temperature (Td), it is possible to prevent intermolecular recrystallization and maintain a stable state of the thin film when heat is generated during driving of the rear light emitting element, thereby achieving a low deposition temperature.
Next, the effects described above and the additional effects will be described in detail.
Drawings
Fig. 1 is a schematic cross-sectional view illustrating a structure of a back surface light-emitting element according to an embodiment of the present invention.
Fig. 2 is an electron micrograph (SEM) of the film uniformity.
[ notation ] to show
200: hole injection layer
300: hole transport layer
400: luminescent layer
500: electron transport layer
600: electron injection layer
1000: electrode 1 (anode, transparent electrode)
2000: electrode 2 (cathode, reflective electrode)
3000: reflective electrode protection 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" may refer to groups such as those comprising phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylene, phenylene, perylene,
Figure BDA0003257360980000061
Fluoro, fluoranthenyl, benzofluorenyl, benzotrriphenylene, benzo
Figure BDA0003257360980000062
Aryl group of C5-50 including aromatic ring such as pyridyl, anthryl, stilbenyl and pyrenyl, and "heteroaryl" refers to aromatic ring group including pyrrolyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, quinolyl, isoquinolyl, quinoxalyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dipyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyridine ring, dipyridamole ring, pyridine ring, etc
Figure BDA0003257360980000063
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 BDA0003257360980000064
An azolyl ring,
Figure BDA0003257360980000065
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 at least one hetero element and having C2-50 atoms.
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" means substituted or unsubstituted with any one or more groups selected from the group consisting of deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, or C-C alkyl group, C-C alkylsulfinyl group, C-C alkylsulfonyl group, C-C alkylsulfanyl group, C-C fluoroalkyl group, C-C alkenyl group, C-C alkoxy group, C-C N-alkylamino group, C-C N, N-dialkylamino group, substituted or unsubstituted C-C mercapto group, C-C N-alkylsulfamoyl group, C-C N, N-dialkylsulfamoyl group, C-C silyl group, C-C cycloalkyl group, C-C heterocycloalkyl group, C-C aryl group, and C-C heteroaryl group, etc., but is not particularly limited thereto. 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.
Next, the present invention will be described in detail.
The compound for the reflective electrode protection layer of the back light-emitting element according to the present invention may be represented by the following chemical formula 1:
< chemical formula 1>
Figure BDA0003257360980000081
In the chemical formula 1, the first and second organic solvents,
Ar1to Ar4Each independently is a substituted or unsubstituted aryl group of C6-C50, or a substituted or unsubstituted heteroaryl group of C2-C50,
l is a substituted or unsubstituted arylene group having from C6 to C50 and consisting of 1 or 2 rings or a substituted or unsubstituted heteroarylene group having from C2 to C50 and consisting of 1 or 2 rings,
L1to L4Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50.
Specifically, in the chemical formula 1, Ar1And Ar2、Ar3And Ar4Each may be identical to each other. More specifically, Ar1To Ar4Any one or more of these groups may be a substituted or unsubstituted aryl group of C12 or more, a substituted or unsubstituted fused aryl group of C10 or more, a substituted or unsubstituted heteroaryl group of C5 or more, or a substituted or unsubstituted fused heteroaryl group of C7 or more.
In particular toIn the chemical formula 1, Ar1And Ar2May be each independently an aryl group of C12 or more, a condensed aryl group of C10 or more, a heteroaryl group of C5 or more, or a condensed heteroaryl group of C7 or more, Ar3And Ar4May each independently be an aryl group of C6 or less or a heteroaryl group of C5 or less. Thereby, the thermal stability of the compound at the time of deposition can be improved by lowering the deposition temperature.
Further, in Ar of the chemical formula 11To Ar4The difference in the number of carbons between the selected 2 species and the remaining 2 species may be 6 or more, respectively. Thereby, it is possible to have a high glass transition temperature (Tg) while lowering the deposition temperature, and thus thermal stability at the time of deposition and driving is excellent.
In the chemical formula 1, Ar1And Ar2May each independently be a phenanthryl group, a triphenylene group, or a pyrenyl group. In the case as described above, it is possible to have a high glass transition temperature (Tg), and thus thermal stability at the time of element driving is excellent.
In the chemical formula 1, L may be phenylene or heteroarylene of C5 or less. Specifically, L may be a phenylene group or a 6-membered ring structure substituted with one or more N, and may be, for example, a phenylene group, a pyridyl group, a pyrimidyl group or a triazinyl group. In the case as described above, the thermal stability of the compound at the time of deposition can be improved by lowering the deposition temperature.
In said chemical formula 1, L, L1And L2May have meta-binding or ortho-binding. Specifically, L, L1And L2At least one of which may be m-phenylene or o-phenylene. Therefore, lower deposition temperature can be realized, and the thickness of the protective layer can be improved more favorably due to the distortion of the compound, so that the service life of the element can be prolonged effectively.
Further, in the chemical formula 1, Ar1To Ar4And at least one of L may be pyridyl, pyrimidinyl, pyrazinyl, or triazinyl. In the case described above, excellent intermolecular binding can be ensured by the nitrogen atomAnd the service life can be effectively prolonged by arrangement.
The deposition temperature of the compound of formula 1 is at
Figure BDA0003257360980000101
The temperature at/sec may be 320 ℃ or lower.
The compound of chemical formula 1 may have a glass transition temperature (Tg) of 85 ℃ or more.
The following compounds are specific examples of the compound of chemical formula 1 according to the present invention. The following examples are merely illustrative of the present invention and the present invention is not limited thereto.
Figure BDA0003257360980000111
Figure BDA0003257360980000121
Figure BDA0003257360980000131
Figure BDA0003257360980000141
Figure BDA0003257360980000151
Figure BDA0003257360980000161
Figure BDA0003257360980000171
Figure BDA0003257360980000181
Figure BDA0003257360980000191
Figure BDA0003257360980000201
Figure BDA0003257360980000211
The general synthesis reaction formula of the compound according to an embodiment of the present invention is shown below, but is not limited thereto.
< reaction formula 1>
Figure BDA0003257360980000221
In another embodiment of the present invention, there is provided a back light-emitting element containing the compound for a reflective electrode protective layer according to the present invention as described above in a reflective electrode protective layer.
Next, a back surface light emitting element according to the present invention will be described in more detail.
The present invention provides a back surface light emitting element comprising: a1 st electrode and a 2 nd reflective electrode; 1 or more organic layers interposed between the 1 st and 2 nd reflective electrodes; and a reflective electrode protection layer disposed outside the 2 nd reflective electrode, the reflective electrode protection layer containing the compound for reflective electrode protection layer. The back surface light emitting element may specifically be an organic light emitting element which emits light from the back surface.
The reflective electrode is an opaque electrode that reflects light transmitted from a light emitting layer interposed inside the electrode.
The organic layer may have a structure in which 2 or more light-emitting layers are stacked, and a 2 nd protective layer may be provided outside the reflective electrode protective layer. Specifically, the second protective layer may be an inorganic substance, and may be, for example, silicon nitride or silicon oxide.
The reflective electrode protection layer may have a thickness of 2500 a to 2500 a
Figure BDA0003257360980000231
Specifically, it may be 4000 to 4000
Figure BDA0003257360980000232
In the case as described above, the service life of the reflective electrode can be further improved.
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 back 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, transparent electrode) and a 2 nd electrode (cathode, reflective electrode). Wherein the 1 st electrode may be a transparent electrode and the 2 nd electrode may be a reflective electrode.
Fig. 1 is a sectional view schematically illustrating the structure of a back surface light-emitting element according to an embodiment of the present invention. A back surface light emitting element according to an embodiment of the present invention can be manufactured in a structure as shown in fig. 1.
As shown in fig. 1, the back light-emitting element may have a structure in which 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 reflective electrode protection layer 3000 are stacked in this order from bottom to top. The 1 st electrode may be a transparent electrode and the 2 nd electrode may be a reflective electrode. When light is emitted to the outside through the 1 st electrode and back-surface light emission is performed, the 2 nd electrode can reflect light generated inside in the direction of the 1 st electrode again as a reflective electrode.
The 1 st electrode 1000 is used as a hole injection electrode for injecting holes into the back light-emitting element. 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).
Meanwhile, the hole injection layer 200 may be formed by depositing a hole injection layer material on the upper portion of the 1 st electrode 1000 using 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 BDA0003257360980000251
Deposition rate per second and
Figure BDA0003257360980000252
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.
Further, 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, a langmuir-blodgetta (LB) method, or the like. In the formation of the hole transport layer 300 by the vacuum deposition method, the deposition conditions thereof will vary depending on the compound used, but are generally selected within the almost same range of conditions as in the formation of the hole injection layer 200. The hole transport layer 300 may 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.
Meanwhile, the light emitting layer 400 may 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, a langmuir-blodgetta (LB) method, or the like. When the light-emitting layer 400 is formed by the vacuum deposition method, the deposition conditions thereof will vary depending on the compound used, but are generally selected within the almost same range as the conditions for forming the hole injection layer 200. As the material of the light-emitting layer, a known compound can be used as a host or a dopant.
In the case where a phosphorescent dopant is used together with 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 diffusion of triplet excitons or holes into the electron transport layer 500. The hole-blocking material that can be used is not particularly limited, and any known material can be selected and used. For example, it is possible to use
Figure BDA0003257360980000261
The most typical 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 (phenanthrolines) compounds (e.g., BCP (bathocuproine) from UDC). The light emitting layer 400 of the present invention as described above may include 1 or more or 2 or more blue light emitting layers.
In addition, the electron transport layer 500 is formed on the light emitting layer 400, and may be formed by a method such as 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 suitable within almost the same range of conditions as the formation of the hole injection layer 200.
Further, 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 method such as a vacuum deposition method, a spin coating method, a casting method, or the like.
In addition, the 2 nd electrode 2000 is used as an electron injection electrode, and can reflect light generated in a light emitting layer inside the electrode. The electron injection layer 600 may be formed on the upper portion thereof by a vacuum deposition method, a spin coating method, or the like. As a material of the 2 nd electrode 2000, various metals that can reflect light may be used, and for example, aluminum (Al), silver (Ag), or the like may be used, but is not limited thereto.
In the back surface light emitting element of the present invention, a plurality of layers may be added as necessary in addition to the above-described layers.
Further, the thickness of each organic layer formed by the present invention may be adjusted to a desired degree, specifically, 10 to 1000nm, more specifically, 20 to 150 nm.
As shown in fig. 1, the reflective electrode protection layer 3000 is formed on the outer surface of the 2 nd electrode 2000 to protect the reflective electrode.
Next, the present invention will be described in more detail by way of a synthesis example of a compound according to an embodiment of the present invention and a manufacturing example of a back surface light-emitting element. The following synthesis examples and examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.
Synthesis example 1: synthesis of Compound 1
Figure BDA0003257360980000271
In a round-bottomed flask, 4.0g of 4-bromo-1,1':4',1 "-terphenyl (4-bromo-1,1':4', 1" -terphenyl), 3.4g of N1, N4-diphenylbenzene-1,4-diamine (N1, N4-diphenylbenzene-1,4-diamine), 1.9g of t-Buona, 0.5g of Pd2(dba)30.5ml of (t-Bu)3After dissolving P in 120ml 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 MC (Methylene chloride) and recrystallized after filtration under reduced pressure, thereby obtaining 6.0g of compound 1. (yield 65%)
m/z：716.32(100.0％)、717.32(59.1％)、718.33(17.0％)、719.33(3.2％)
Synthesis example 2: synthesis of Compound 19
Figure BDA0003257360980000281
Compound 19 was synthesized in the same manner as in Synthesis example 1, using 9-bromophenanthrene (9-bromophenanthrene) in place of 4-bromo-1,1':4',1 "-terphenyl (4-bromoo-1, 1':4', 1" -terphenyl). (yield 70%)
m/z：612.26(100.0％)、613.26(50.1％)、614.26(12.5％)、615.27(2.0％)
Synthesis example 3: synthesis of Compound 20
Figure BDA0003257360980000291
Compound 20 was synthesized in the same manner as in Synthesis example 1, except that N1, N3-diphenylbenzene-1,3-diamine (N1, N3-diphenylbenzene-1,3-diamine) was used in place of N1, N4-diphenylbenzene-1,4-diamine (N1, N4-diphenylbenzene-1,4-diamine) and 9-bromophenanthrene (9-bromophenanthrene) was used in place of 4-bromo-1,1':4',1 '-terphenyl (4-bromoo-1, 1':4', 1' -terphenyl). (yield 60%)
m/z：612.26(100.0％)、613.26(50.1％)、614.26(12.5％)、615.27(2.0％)
Synthesis example 4: synthesis of Compound 28
Figure BDA0003257360980000292
Compound 28 was synthesized in the same manner as in Synthesis example 1, except that N4, N4'-diphenyl- [1,1' -biphenyl ] -4,4'-diamine (N4, N4' -diphenylyl- [1,1'-biphenyl ] -4,4' -diamine) was used in place of N1, N4-diphenylbenzene-1,4-diamine (N1, N4-diphenylbenzene-1,4-diamine) and 2-bromobenzo (2-bromobisphenylene) was used in place of 4-bromo-1,1':4',1 '-terphenyl (4-bromoo-1, 1':4', 1' -terphenyl). (yield 63%)
m/z：788.3191(100.0％)、789.3225(64.9％)、790.3259(20.7％)、791.3292(4.3％)
Synthesis example 5: synthesis of Compound 130
Figure BDA0003257360980000301
Compound 130 was synthesized in the same manner as in Synthesis example 1, except that pyridine-2,6-diamine (pyridine-2,6-diamine) was used in place of N1, N4-diphenylbenzene-1,4-diamine (N1, N4-diphenylbenzene-1,4-diamine) and 9-bromophenanthrene (9-bromophenanthrene) was used in place of 4-bromo-1,1':4',1 '-terphenyl (4-bromoo-1, 1':4', 1' -terphenyl). (yield 61%)
m/z：613.25(100.0％)、614.26(49.0％)、615.26(11.8％)、616.26(2.0％)、614.25(1.1％)
Fabrication of back side light emitting devices
A back surface light emitting element was manufactured in the structure shown in fig. 1. The back light-emitting element is formed by sequentially laminating a substrate 100/an anode (hole injection electrode, transparent 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, reflective electrode 2000)/a reflective electrode protection layer 3000 in this order from bottom to top.
The compounds used in the organic layer located inside the electrode of the back light-emitting element of the present invention are shown in table 1 below.
[ TABLE 1 ]
Figure BDA0003257360980000311
Example 1
Forming a hole injection layer on an Indium Tin Oxide (ITO) substrate
Figure BDA0003257360980000312
HI01,
Figure BDA0003257360980000313
And as a hole transport layer
Figure BDA0003257360980000314
HT01 (g), and doping with BH01: BD 013% to form a film
Figure BDA0003257360980000315
The light emitting layer of (a). Next, the film is formed as an electron transport layer
Figure BDA0003257360980000321
ET01 Liq (1:1) followed by deposition
Figure BDA0003257360980000322
The electron injection layer is formed. Further, as a reflective electrode deposition formation
Figure BDA0003257360980000323
Al in a thickness and deposited over the reflective electrode (cathode) as a protective layer for the reflective electrode
Figure BDA0003257360980000324
Thickness of compound 1 produced in synthesis example 1. The back light emitting element was manufactured by encapsulating the element in a glove box (Encapsulation).
Examples 2 to 5
A reflective electrode protection layer was formed by deposition of each of the compounds produced in synthesis examples 2 to 5 in the same manner as in example 1, thereby producing a back light-emitting device.
Example 6
According to the followingThe same process as in example 1 was conducted, wherein the film was formed as a reflective electrode protective layer
Figure BDA0003257360980000326
The compound 1 produced in synthesis example 1 was synthesized to produce a back surface light-emitting element.
Example 7
The production was carried out in the same manner as in example 1, wherein the film was formed as a reflective electrode protective layer
Figure BDA0003257360980000325
The compound 1 produced in synthesis example 1 was synthesized to produce a back surface light-emitting element.
Comparative examples 1 and 2
A reflective electrode protection layer was formed by a method similar to that of example 1, using comparative compound 1(ref.1) and comparative compound 2(ref.2) shown in table 2 below, respectively, to manufacture a back light emitting device.
[ TABLE 2 ]
Figure BDA0003257360980000331
Comparative example 3: manufacture of front-side light-emitting element
Forming a hole injection layer on an Indium Tin Oxide (ITO) substrate having a reflective layer containing Ag
Figure BDA0003257360980000332
HI01,
Figure BDA0003257360980000333
And as a hole transport layer
Figure BDA0003257360980000334
HT01 (g), and doping with BH01: BD 013% to form a film
Figure BDA0003257360980000335
The light emitting layer of (a). Next, the film is formed as an electron transport layer
Figure BDA0003257360980000336
ET01 Liq (1:1) followed by deposition
Figure BDA0003257360980000337
The electron injection layer is formed. Next, MgAg was deposited as a transparent electrode (cathode) at a thickness of 15nm, and then comparative compound 1(Ref.1) was deposited over the cathode as a light efficiency improving layer
Figure BDA0003257360980000338
Is deposited to a thickness of (a). The front light emitting element was manufactured by encapsulating (Encapsulation) the element in a glove box.
Evaluation of the Performance of the component
The performance of the devices according to examples 1 to 7 and comparative examples 1 to 3, i.e., the current density and the luminance with respect to the applied voltage, were evaluated under atmospheric pressure conditions by applying a voltage to a gievi 2400 source measurement unit (kinetey 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 ]
Op.V mA/cm2 Cd/A LT50
Example 1 3.6 10 9.5 1030
Example 2 3.6 10 9.5 1050
Example 3 3.6 10 9.5 1080
Example 4 3.6 10 9.5 1040
Example 5 3.6 10 9.5 1090
Example 6 3.6 10 9.5 1290
Example 7 3.6 10 9.5 1280
Comparative example 1 3.6 10 9.5 820
Comparative example 2 3.6 10 9.5 690
Comparative example 3 3.7 10 5.5 560
It was found that the compound of the present invention has 2 arylamine structures bonded through a linker whose volume characteristics are minimized, and thus bubbles and recrystallization are not formed on the surface and side of deposition, and thus a thin film can be stably formed, as compared to comparative examples 1 and 2. Thereby, the stability of the element under oxygen, moisture and external contamination can be effectively improved, and the service life can be remarkably improved. In addition, it can be seen that the back light emitting structure of the present invention is used to protect the reflective electrode and to improve the lifespan
Figure BDA0003257360980000351
The electrode protection layer having the above thickness is preferable, but is formed by stacking in the front emission structure as shown in comparative example 3
Figure BDA0003257360980000352
A thick light efficiency improving layer leads to a significant reduction in efficiency and lifetime. That is, when the front emission structure is laminated to a certain thickness or more in order to sufficiently achieve the function as an electrode protection layer, the element balance is finally deteriorated and the lifetime is reduced due to a significant decrease in transmittance and a decrease in light extraction efficiency. Further, a comparison between examples 6 and 7 shows that
Figure BDA0003257360980000353
The service life can be further improved even in the case of lamination
Figure BDA0003257360980000354
The above thickness does not exhibit a significant service life improvement effect in proportion to the thickness. Whereby it can be learned through the application
Figure BDA0003257360980000355
Can reduce the consumption of the protective film material and can be commercialized more efficiently.
Film uniformity measurement
3g each of comparative compound 1(ref.1), comparative compound 2(ref.2), compound 19, and compound 20 was vacuum-deposited on a glass substrate, and the top and side surfaces were measured by a scanning electron microscope (SEM, hitachi, SU8010) after heat treatment at 100 ℃ for 30 minutes, and the results are shown in fig. 2. Referring to fig. 2, it can be seen that the compound of the present invention forms a uniform thin film on both the upper end and the side of the cross section, compared to the comparative example, indicating that a stable thin film can be effectively formed. Although not shown, other compounds proposed in the synthesis example of the present invention can form a uniform thin film.

Claims (14)

1. A compound for a reflective electrode protection layer of a back light-emitting element represented by the following chemical formula 1:
chemical formula 1
Figure FDA0003257360970000011
In the chemical formula 1, the first and second organic solvents,
Ar1to Ar4Each independently is a substituted or unsubstituted aryl group of C6-C50, or a substituted or unsubstituted heteroaryl group of C2-C50,
l is a substituted or unsubstituted arylene group having from C6 to C50 and consisting of 1 or 2 rings or a substituted or unsubstituted heteroarylene group having from C2 to C50 and consisting of 1 or 2 rings,
L1to L4Each independently is a direct bond, a substituted or unsubstituted arylene group of C6 to C50, or a substituted or unsubstituted heteroarylene group of C2 to C50.
2. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
Ar1and Ar2Each independently an aryl group of C12 or more, a fused aryl group of C10 or more, a heteroaryl group of C5 or more, or a fused heteroaryl group of C7 or more,
Ar3and Ar4Each independently is an aryl group of C6 or less or a heteroaryl group of C5 or less.
3. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
at Ar1To Ar4The difference in the number of carbons between the selected 2 species and the remaining 2 species is 6 or more, respectively.
4. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
Ar1and Ar2Each independently is a phenanthryl, triphenylene, or pyrenyl group.
5. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
l is phenylene or heteroarylene of C5 or less.
6. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
L、L1and L2Has meta-binding or ortho-binding.
7. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
L、L1and L2At least one of which is m-phenylene or o-phenylene.
8. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
Ar1to Ar4And at least one of L is pyridyl, pyrimidinyl, pyrazinyl, or triazinyl.
9. The compound for a reflective electrode protection layer of a back light-emitting element according to claim 1,
the compound of chemical formula 1 is any one of compounds represented by the following chemical formulae:
Figure FDA0003257360970000041
Figure FDA0003257360970000051
Figure FDA0003257360970000061
Figure FDA0003257360970000071
Figure FDA0003257360970000081
Figure FDA0003257360970000091
Figure FDA0003257360970000101
Figure FDA0003257360970000111
Figure FDA0003257360970000121
Figure FDA0003257360970000131
Figure FDA0003257360970000141
10. a back side light emitting device, comprising:
a1 st electrode and a 2 nd reflective electrode;
1 or more organic layers interposed between the 1 st and 2 nd reflective electrodes; and the number of the first and second groups,
a reflective electrode protection layer disposed outside the 2 nd reflective electrode, comprising the compound for a reflective electrode protection layer according to any one of claims 1 to 9.
11. The back surface light-emitting element according to claim 10,
the reflective electrode protection layer has a thickness of 2500 to
Figure FDA0003257360970000151
12. The back surface light-emitting element according to claim 10,
the organic layer has a structure in which 2 or more light-emitting layers are stacked.
13. The back surface light-emitting element according to claim 10,
a 2 nd protective layer is further provided on the outer side of the reflective electrode protective layer.
14. The back surface light-emitting element according to claim 10,
the 2 nd protective layer comprises silicon nitride or silicon oxide.
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