CN109206327B - Novel compound and organic light emitting device comprising the same - Google Patents

Novel compound and organic light emitting device comprising the same Download PDF

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CN109206327B
CN109206327B CN201810699323.2A CN201810699323A CN109206327B CN 109206327 B CN109206327 B CN 109206327B CN 201810699323 A CN201810699323 A CN 201810699323A CN 109206327 B CN109206327 B CN 109206327B
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compound
chemical formula
layer
organic light
present
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CN109206327A (en
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咸昊完
安贤哲
姜京敏
金东骏
闵丙哲
文锺勋
徐净雅
李萤振
林东焕
林大喆
金昇好
权桐热
李成圭
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Dongjin Semichem Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to novel arylamine compounds, which, when used as a Hole Transport Layer (HTL), a light emitting auxiliary layer (HT prime), or a Hole Injection Layer (HIL), can increase hole injection and transport characteristics, thereby providing high efficiency and long life effects of devices.

Description

Novel compound and organic light emitting device comprising the same
Technical Field
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In the organic light emitting diode, materials used as the organic layer may be broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like according to functions. The luminescent materials are classified into high-molecular and low-molecular materials according to molecular weight, and into fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to luminescence mechanism, and the luminescent materials are classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to exhibit better natural colors according to luminescence colors. Also, in order to increase color purity and increase luminous efficiency by energy transfer, a host/dopant species may be used as a light-emitting substance. The principle is that when a dopant having a small energy band gap and excellent light emission efficiency as compared with a host mainly constituting a light emitting layer is mixed in a small amount in an auxiliary layer, excitons generated in the host are transported to the dopant, and light having high efficiency is emitted. At this time, the wavelength of the host shifts to the wavelength band of the dopant, and thus light of a desired wavelength can be obtained according to the type of the dopant and the host used.
As a substance used for such an organic light-emitting device, various compounds have been known, but in the case of an organic light-emitting device using a substance known so far, development of a new material is continuously required due to a high driving voltage, low efficiency and short lifetime. Accordingly, there is a continuous effort to develop an organic light emitting device having low voltage driving, high luminance and long life using a substance having excellent characteristics.
Prior art literature
Patent literature
Japanese laid-open patent 10-2015-530735
Disclosure of Invention
The present invention provides novel compounds and organic light emitting devices comprising the same.
However, the problems to be solved by the present invention are not limited to the above-described problems, and other problems not described can be clearly understood by those skilled in the art to which the present invention pertains from the following descriptions.
The first embodiment of the present invention provides a compound represented by the following chemical formula 1.
Chemical formula 1
In the above-mentioned chemical formula 1,
Ar 1 to Ar 3 Each independently is a substituted or unsubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Is a heteroaryl group of (a),
Ar 4 ar and Ar 5 Each independently is a substituted or unsubstituted C 6 ～C 10 Aryl, ar of (2) 4 Ar and Ar 5 The sum of the number of carbon atoms is 16 or less,
r and R' are each independently hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, substituted or unsubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Is a heteroaryl group of (a),
R 1 r is R 2 Each independently is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl of (2), or substituted or unsubstituted C 6 ～C 30 Is a group consisting of an aryl group,
l is substituted or unsubstituted C 6 ～C 30 Arylene of (2), or substituted or unsubstituted C 5 ～C 30 Is a heteroarylene group of (c),
l is 0 or an integer from 1 to 4, m is 0 or an integer from 1 to 3, n is 0 or an integer from 1, and o is an integer from 1 to 4.
The second embodiment of the present invention provides an organic light emitting device comprising the compound of the present invention.
The present invention relates to a novel compound having a fluorene structure and an arylamine structure having a branched aryl group introduced at the end thereof, and more particularly, to a novel compound having a fluorene structure and a branched aryl group introduced at the end thereof, which are directly combined with an arylamine to form a deep HOMO and a high LUMO, thereby easily blocking electrons, increasing pi conjugation by a branched aryl group having a linking group extended, and having excellent thin film alignment of molecules, thereby suppressing a roll-off phenomenon due to rapid hole mobility, thereby realizing a long-life device. And fixing the other aryl group of the aryl groups of the arylamine to C 16 Aryl groups that are not branched aryl groups to maintain proper HOMO and LUMO, high T1, and thus efficiently form excitons within the light emitting layer to realize a high efficiency organic light emitting device.
In the compound of the present invention, when used as a Hole Transport Layer (HTL), a light emitting auxiliary layer (HT prime), or a Hole Injection Layer (HIL), hole injection and transport characteristics can be increased, and thus high efficiency and long life of the device can be provided. The compound of the present invention can maintain high triplet energy to exhibit high efficiency, and can maintain high Tg due to a terminal branched substituent composed of 4 or more aryl groups, thereby exhibiting thin film stability and long life effect when the device is driven.
The compound of the present invention has the effects of high luminous efficiency, high color purity, etc., and is suitable for organic light emitting devices, organic light emitting devices for solar power generation, etc., thereby making a great contribution to the Organic Light Emitting Diode (OLED) industry of flexible displays, illuminators, etc.
Drawings
Fig. 1 shows a schematic view of an organic light emitting device according to an example of the present invention.
Description of the reference numerals
100: substrate board
200: hole injection layer
300: hole transport layer
400: light-emitting layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: cathode electrode
Detailed Description
Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art to which the present invention pertains can easily implement the present invention.
However, the present invention can be realized in many different forms and is not limited to the examples and embodiments described herein. In the drawings, for the purpose of clearly explaining the present invention, parts irrelevant to the explanation are omitted, and like reference numerals are given to like parts throughout the specification.
Throughout the present specification, when one element is located "on" another element, it includes not only the case where one element is in contact with another element but also the case where another element exists between two elements.
Throughout the specification, when a portion "comprises" a structural element, unless specifically stated to the contrary, it is meant that other structural elements may also be included, rather than excluded. The terms "about," "substantially," and the like as used throughout the present specification are used in their numerical or near-numerical meanings when referring to manufacturing and material tolerances, to prevent an ill-minded infringer from improperly utilizing the disclosure of the exact or absolute numerical values mentioned to aid in understanding the present invention. The term "to (a) step" or "a step of" as used throughout the specification of the present invention does not mean "a step of".
Throughout the present specification, the term "combination thereof" included in Markush (Markush) -type expression means a mixture or combination of one or more selected from the group consisting of a plurality of structural elements described in Markush-type expression, and means that one or more selected from the group consisting of the plurality of structural elements is included.
Throughout the present specification, the expression "a and/or B" means "a or B, or a and B".
Throughout the present specification, the term "aryl" is meant to include C 6-30 Aromatic hydrocarbon ring groups of (C) are, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylalkenyl, phenylalkenyl,Phenyl, fluoran thiophene methyl, benzofluorenyl, benzotriphenylenyl, and benzo +.>Aromatic rings of radicals, anthracenyl, stilbene, pyrenyl, etc., as "heteroaryl" as C comprising at least one hetero element 5-30 For example, the aromatic ring of (a) is meant to include an aromatic ring formed from pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthrene cry yl, acridinyl, phenanthroline, thienyl and a pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ringAromatic heterocyclic groups.
Throughout the present specification, the term "alkyl" may comprise straight or branched chain saturated or unsaturated C 1 -C 6 Alkyl groups, for example, may include methyl, ethyl, propyl, butyl, pentyl, hexyl, or all isomers thereof, but are likely not limited thereto.
Throughout the present specification, the term "substituted or unsubstituted" means to be selected from the group consisting of heavy hydrogen, halogen, amino, nitrile, nitro, silane, alkyl or C 1 ～C 20 Alkyl, alkenyl or C 2 ～C 20 Alkenyl, alkoxy or C 1 ～C 20 Alkoxy, cycloalkyl or C 3 ～C 20 Cycloalkyl, heterocycloalkyl or C 3 ～C 20 Is a heterocycloalkyl group or C 5 ～C 30 Aryl or C of (2) 5 ～C 30 More than one group of the heteroaryl group is substituted or unsubstituted. Also, throughout the specification of the present invention, the same reference numerals may have the same meaning unless specifically mentioned.
The first embodiment of the present invention provides a compound represented by the following chemical formula 1:
chemical formula 1
Ar 1 To Ar 3 Each independently is a substituted or unsubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Is a heteroaryl group of (a),
Ar 4 ar and Ar 5 Each independently is a substituted or unsubstituted C 6 ～C 10 But Ar is Ar 4 Ar and Ar 5 The sum of the number of carbon atoms is 16 or less,
r and R' are each independently hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, substituted or unsubstitutedSubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Is a heteroaryl group of (a),
R 1 r is R 2 Each independently is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl of (2), or substituted or unsubstituted C 6 ～C 30 Is a group consisting of an aryl group,
l is substituted or unsubstituted C 6 ～C 30 Arylene of (2), or substituted or unsubstituted C 5 ～C 30 Is a heteroarylene group of (c),
l is 0 or an integer from 1 to 4, m is 0 or an integer from 1 to 3, n is 0 or an integer from 1, and o is an integer from 1 to 4.
In one embodiment of the present invention, R is selected if l, m or o is 2 or more 1 、R 2 Ar and Ar 3 May be the same or different groups, respectively. For example, if o is 2, ar 3 May be two phenyl groups, or one phenyl group and one naphthyl group.
In one embodiment of the present invention, ar is as described above 1 To Ar 3 And each independently may be phenyl, naphthyl, biphenyl, phenanthryl, or triphenylene.
In one embodiment of the present invention, ar is as described above 4 Ar and Ar 5 Each independently may be phenyl or naphthyl.
In one embodiment of the present invention, the above-mentioned L may be phenylene or biphenylene.
In one embodiment of the present invention, each of R and R' may be independently methyl or phenyl.
In one embodiment of the present invention, R is 1 R is R 2 May each independently be hydrogen or phenyl.
In one example of the present invention, the above compound may be represented by the following chemical formula 2:
chemical formula 2
In the above-mentioned chemical formula 2,
Ar 1 to Ar 4 、R、R`、R 1 、R 2 L, L, m and o are as defined in formula 1 above.
In one example of the present invention, the above compound may be represented by the following chemical formula 3:
chemical formula 3
In the above-mentioned chemical formula 3, a compound represented by formula 1,
Ar 1 to Ar 3 、R、R`、R 1 、R 2 L, l and m are as defined in chemical formula 1 above,
R 3 is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Or substituted or unsubstituted C 2 ～C 30 Is used as a base for the reaction of an alkenyl group,
p is 0 or an integer from 1 to 5.
In one example of the present invention, the above compound may include a compound represented by the following chemical formula 4:
chemical formula 4
In the above-mentioned chemical formula 4, a compound represented by formula 1,
Ar 1 to Ar 3 、R 1 、R 2 L, l and m are as defined in chemical formula 1 above,
R 3 is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Or substituted or unsubstituted C 2 ～C 30 Is used as a base for the reaction of an alkenyl group,
p is 0 or an integer from 1 to 5,
ar and Ar' are each independently substituted or unsubstituted C 6 ～C 30 Aryl groups of (a).
In one example of the present invention, the above compound may be represented by the following chemical formula 5:
chemical formula 5
In the above-mentioned chemical formula 5,
Ar 1 to Ar 3 、R 1 、R 2 L, l and m are as defined in chemical formula 1 above,
R 3 is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Or substituted or unsubstituted C 2 ～C 30 Is used as a base for the reaction of an alkenyl group,
p is 0 or an integer from 1 to 5,
R 4 r is R 5 Each independently is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, substituted or unsubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Heteroaryl of (a).
In one example of the present invention, the above compound may be represented by the following chemical formula 6:
chemical formula 6
In the above-mentioned chemical formula 6,
Ar 2 、Ar 3 、R 1 、R 2 l and m are as defined in chemical formula 1 above,
R 3 is hydrogen, heavy hydrogen, substituted or unsubstituted C 1 ～C 30 Or substituted or unsubstituted C 2 ～C 30 Is used as a base for the reaction of an alkenyl group,
p is 0 or an integer from 1 to 5,
R 4 r is R 5 Each independently is hydrogen, heavy hydrogen, substituted or unsubstitutedSubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, substituted or unsubstituted C 6 ～C 30 Or substituted or unsubstituted C 5 ～C 30 Heteroaryl of (a).
In one example of the present invention, the compound represented by the above chemical formula 1 may be synthesized by the reaction shown in the following reaction formula 1, but may not be limited thereto.
Reaction 1
In the above-mentioned reaction scheme, the reaction mixture,
Ar 1 to Ar 5 、R、R`、R 1 、R 2 L, l, m, n and o are as defined in chemical formula 1 above, h denotes a halogen atom.
In one example of the present invention, the compound represented by the above chemical formula 1 may include, but is not likely to be limited to, the following:
for example, the compound represented by the above chemical formula 1 may be one of the following compounds, which minimize the condensation group to maintain a higher T1, and thus maximize the exciton confinement effect in the light emitting layer:
the second embodiment of the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. The organic light-emitting device may include 1 or more organic layers containing the compound of the present invention between the first electrode and the second electrode.
In one embodiment of the present invention, the organic layer may be 1 or more layers of the hole injection layer, the hole transport layer and the light emitting auxiliary layer, for example, may be light emitting auxiliary layers, but may not be limited thereto, and in this case, the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
In the present invention, the light-emitting auxiliary layer refers to a layer formed between the hole transport layer and the light-emitting layer, and may be referred to as a second hole transport layer, a third hole transport layer, or the like depending on the number of hole transport layers.
In one example of the present invention, the organic light emitting device may include an organic layer including a hole transporting substance and an organic layer including a compound represented by the above chemical formula 1, but may not be limited thereto.
The organic light emitting device may include organic layers 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 an anode (anode) and a cathode (cathode) of 1 or more layers.
For example, the above-described organic light emitting device may be manufactured according to the structure described in fig. 1. The organic light emitting device may sequentially stack an anode (hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/light emitting layer 400/electron transport layer 500/electron injection layer 600/cathode (electron injection electrode 2000) from bottom to top.
In fig. 1, a substrate for an organic light emitting device may be used as the substrate 100, and in particular, a transparent glass substrate or a bendable plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency may be used.
The hole injection electrode 1000 serves as an anode for injecting holes of the organic light emitting device. In order to inject holes, a material having a low work function 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 anode electrode by a vacuum deposition method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, or the like. In the case of forming the hole injection layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the hole injection layer required, etc., but may be generally at a deposition temperature of 50 to 500 ℃, 10 -8 To 10 -3 Vacuum degree of torr (Torr), 0.01 toDeposition rate, < >>The layer thickness to 5 μm is suitably selected.
Next, a hole transporting layer substance is deposited on the hole injecting layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, whereby the hole transporting layer 300 can be formed. In the case of forming the hole transport layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used, but in general, it is preferable to select in the range of conditions almost the same as the formation of the hole injection layer. The hole transport layer may be one or more layers, for example, a first hole transport layer and a second hole transport layer (light-emitting auxiliary layer). At least one of the first hole transporting layer and the second hole transporting layer may include the compound of formula 1 of the present invention.
Next, a light-emitting layer substance is deposited over the hole-transporting layer or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, whereby the light-emitting layer 400 can be formed. In the case of forming the light-emitting layer by the above vacuum deposition method, the deposition conditions thereof are different depending on the compound used, but in general, it is preferable to select in the range of conditions almost the same as the formation of the hole injection layer. The light-emitting layer material may use a known compound as a host or a dopant.
In addition, when the light-emitting layer is used together with a phosphorescent dopant, a hole-suppressing material (HBL) may be laminated by a vacuum deposition method or a spin coating method in order to prevent diffusion of triplet excitons or holes into the electron-transporting layer. The hole-inhibiting substance that can be used in this case is not particularly limited, but any substance can be selected from known substances used as hole-inhibiting materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole-suppressing materials described in Japanese patent application laid-open No. 11-329734 (A1) are exemplified, and typically Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenol), phenanthroline (phe nanthrolins) compounds (such as BCP (Basso Coupoline) of Universal Display (UDC)) and the like are used.
An electron transporting layer 500 is formed on the light emitting layer 400 formed as described above, and in this case, the electron transporting layer 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 are different depending on the compound used, but in general, it is preferable to select the conditions within the range substantially equal to the conditions for forming the hole injection layer.
Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600, and in this case, the electron transport layer may be formed into a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, or the like.
The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the organic light emitting device may use the compound of the present invention or the following materials, or may use the compound of the present invention together with known materials.
The cathode 2000 for injecting electrons is formed on the electron injection layer 600 by a vacuum deposition method, a sputtering method, or the like. As the cathode, various metals can be used. Specific examples include aluminum, gold, silver, and the like.
The organic light-emitting device of the invention can not only adopt an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode structure, but also adopt the structures of organic light-emitting devices with various structures, and can also form one or two layers of intermediate layers according to requirements.
As described above, the thickness of each organic layer formed according to the present invention may be adjusted according to a desired degree, and preferably, it is specifically 10 to 1000nm, more specifically 20 to 150nm.
In the present invention, the organic layer containing the compound represented by the above chemical formula 1 has advantages in that the thickness of the organic layer can be adjusted to a molecular unit, and thus the surface is uniform and the morphological stability is outstanding.
The organic light-emitting compound according to the first embodiment of the present invention is not limited to any particular one, and may be any one as long as it is a compound having a high molecular weight.
Hereinafter, the present invention will be described more specifically with reference to examples, but the scope of the present invention is not limited to the examples.
Examples
Preparation example 1 Synthesis of IM
For the synthesis of the objective compound, the synthesis is performed through the above steps to prepare IM.
The synthesis of IM1 is described below.
48.5g of [1,1':3',1 "-tetraphenyl were placed in a round-bottomed flask]-5' -Ylboronic acid, 50.0g of 1-bromo-4-iodobenzene were dissolved in 1000ml of 1, 4-dioxane and put into 265ml of K 2 CO 3 (2M) and 6.1g of Pd (PPh) 3 ) 4 After that, the mixture was stirred under reflux. After confirming the reaction by Thin Layer Chromatography (TLC) and adding water, the reaction was terminated. The organic layer was extracted with Methyl Cellulose (MC), and after filtration under reduced pressure, recrystallization was performed to obtain 50.4g (yield 74%) of intermediate IM1.
The following IM2 to IM9 were synthesized by changing the starting materials in the same manner as in IM1 described above.
PREPARATION EXAMPLE 2 Synthesis of OP
The following synthesis of OP1 is described below.
15.0g of the above 2-bromo-9, 9-dimethyl-9H-fluorene, 5.6g of aniline, 7.9g of t-Buona, 2.0g of Pd are placed in a round-bottomed flask 2 (dba) 3 2.5ml (t-Bu) 3 After dissolving P in 200ml of toluene, stirring under reflux. After confirming the reaction by Thin Layer Chromatography (TLC) and adding water, the reaction was terminated. The organic layer was extracted with Methyl Cellulose (MC), and after filtration under reduced pressure, recrystallization was performed to obtain 11.75g (yield 75%) of OP1.
The following OP2 to OP12 were synthesized by changing the starting materials in the same manner as in the above OP1.
Synthesis example 1 Synthesis of Compound 1
In a round-bottomed flask, 3.0g of IM1, 2.8g of OP2, 1.1g of t-Buona, 0.3g of Pd 2 (dba) 3 0.3ml (t-Bu) 3 After dissolving P in 90ml of toluene, stirring under reflux. After confirming the reaction by Thin Layer Chromatography (TLC) and adding water, the reaction was terminated. The organic layer was extracted with Methyl Cellulose (MC), and after filtration under reduced pressure, column purification and recrystallization were performed to obtain 3.37g (yield 65%) of compound 1.
m/z：665.31(100.0％)、666.31(56.0％)、667.31(15.1％)、668.32(2.7％)
Synthesis example 2 Synthesis of Compound 2
Compound 2 was synthesized in the same manner as compound 1 using OP3 instead of OP2 (yield 68%).
m/z：665.31(100.0％)、666.31(56.0％)、667.31(15.1％)、668.32(2.7％)
Synthesis example 3 Synthesis of Compound 3
Compound 3 was synthesized in the same manner as compound 1 using IM7 and OP1 instead of IM1 and OP2 (yield 66%).
m/z：665.31(100.0％)、666.31(56.0％)、667.31(15.1％)、668.32(2.7％)
Synthesis example 4 Synthesis of Compound 4
Compound 4 was synthesized in the same manner as compound 1 using OP4 instead of OP2 (yield 70%).
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 5 Synthesis of Compound 5
Compound 5 was synthesized in the same manner as compound 1 using IM2 and OP4 instead of IM1 and OP2 (yield 69%).
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 6 Synthesis of Compound 6
Compound 6 was synthesized in the same manner as compound 1 using IM3 and OP4 instead of IM1 and OP2 (yield 65%).
m/z：713.31(100.0％)、714.31(60.3％)、715.31(17.6％)、716.32(3.4％)
Synthesis example 7 Synthesis of Compound 7
Compound 7 was synthesized in the same manner as compound 1 using IM4 and OP4 instead of IM1 and OP2 (yield 67%).
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 8 Synthesis of Compound 8
Compound 8 was synthesized (yield 63%) in the same manner as compound 1 using IM5 and OP4 instead of IM1 and OP 2.
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 9 Synthesis of Compound 9
Compound 9 was synthesized (yield 60%) in the same manner as compound 1 using IM6 and OP4 instead of IM1 and OP 2.
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 10 Synthesis of Compound 10
Compound 10 was synthesized in the same manner as compound 1 using IM7 and OP4 instead of IM1 and OP2 (yield 68%).
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 11 Synthesis of Compound 11
Compound 11 was synthesized in the same manner as compound 1 using IM8 and OP4 instead of IM1 and OP2 (yield 65%).
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 12 Synthesis of Compound 12
Compound 12 was synthesized (yield 60%) in the same manner as compound 1 using IM9 and OP4 instead of IM1 and OP 2.
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Synthesis example 13 Synthesis of Compound 13
Compound 13 was synthesized in the same manner as compound 1 using OP5 instead of OP2 (yield 67%).
m/z：763.32(100.0％)、764.33(64.3％)、765.33(20.3％)、766.33(4.2％)
Synthesis example 14 Synthesis of Compound 14
Compound 14 was synthesized in the same manner as compound 1 using OP6 instead of OP2 (yield 69%).
m/z：763.32(100.0％)、764.33(64.3％)、765.33(20.3％)、766.33(4.2％)
Synthesis example 15 Synthesis of Compound 15
Compound 15 was synthesized in the same manner as compound 1 using OP7 instead of OP2 (yield 75%).
m/z：789.34(100.0％)、790.34(66.3％)、791.35(21.7％)、792.35(4.7％)
Example 1: preparation of organic light-emitting device
By ultrasonic pairing of distilled waterThe glass substrate coated with Indium Tin Oxide (ITO) into a thin film was washed. After the completion of the distilled water washing, the substrate was washed with ultrasonic waves using a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma washer, and then washed with oxygen plasma for 5 minutes, and then treated with a thermal vacuum deposition (thermal evaporator) as a hole injection layer on the top of the indium tin oxide substrate>H101 of (2) and subjecting +.>Is formed into a film by HATCN of (C), and +.>BPA of (A) is formed into a film and +.>After the compound 1 of (a) was formed into a film, 3% BH01 was doped as the light-emitting layer: BD01, 2->And (5) film formation is carried out. Next, as an electron transport layer, would +.>ET01 of (c): after Liq (1:1) film formation, +.>LiF, & gt>Film formation is carried out on aluminum (Al) and the device is sealed in a glove boxEncapsulation (Encapsulation) to prepare an organic light emitting device.
Examples 2 to 15: preparation of organic light-emitting device
An organic light-emitting device in which a light-emitting auxiliary layer was formed using compounds 2 to 15 instead of compound 1 was produced in the same manner as in example 1.
Comparative examples 1 to 2
In the same manner as in example 1, the following ref.1 to ref.9 were used instead of the compound 1, respectively, to prepare organic light emitting devices.
Experimental example 1: performance evaluation of organic light emitting device
The performance of the organic light emitting devices of examples and comparative examples was evaluated by applying a voltage to inject electrons and holes using a Jiehley 2400 source measurement unit (Kiethley 2400 source measureme nt unit), and measuring the brightness at the time of light emission using a Konica Minolta spectroradiometer (CS-2000), thereby measuring the current density and brightness with respect to the applied voltage under the atmospheric pressure condition, and the results thereof are shown in Table 1.
TABLE 1
Op.V mA/cm 2 Cd/A QE(％) CIEx CIEy LT97
Example 1 3.90 10 7.02 6.14 0.140 0.109 107
Example 2 3.89 10 7.10 6.10 0.140 0.110 115
Example 3 3.91 10 7.15 6.19 0.140 0.109 125
Example 4 3.95 10 7.40 6.40 0.140 0.110 170
Example 5 3.98 10 7.45 6.35 0.141 0.110 160
Example 6 3.96 10 7.34 6.35 0.140 0.110 171
Example 7 3.95 10 7.35 6.37 0.140 0.110 166
Example 8 3.95 10 7.33 6.40 0.140 0.109 165
Example 9 3.95 10 7.30 6.38 0.139 0.110 165
Example 10 3.95 10 7.33 6.39 0.141 0.110 170
Example 11 3.94 10 7.35 6.35 0.140 0.110 165
Example 12 3.95 10 7.35 6.34 0.140 0.111 165
Example 13 3.95 10 7.35 6.40 0.140 0.110 163
Example 14 3.94 10 7.37 6.39 0.140 0.110 161
Example 15 3.96 10 7.23 6.29 0.141 0.110 151
Comparative example 1 4.25 10 6.30 5.18 0.142 0.111 50
Comparative example 2 4.28 10 6.33 5.26 0.143 0.110 49
Comparative example 3 4.05 10 6.48 5.44 0.141 0.112 64
Comparative example 4 4.03 10 6.54 5.50 0.141 0.112 70
Comparative example 5 4.02 10 6.80 5.35 0.141 0.111 85
Comparative example 6 4.05 10 6.55 5.50 0.143 0.111 66
Comparative example 7 4.09 10 6.87 5.71 0.141 0.111 79
Comparative example 8 4.05 10 6.42 5.60 0.141 0.112 60
Comparative example 9 4.09 10 6.82 5.60 0.141 0.111 72
As shown in table 1, the following results show that the driving voltage is lower, and the efficiency and life are improved in the examples of the present invention as compared with comparative examples 1 to 9.
More specifically, in the examples of the present invention, it was found that 1) an aryl amine was directly bonded to the second position of fluorene in comparison with comparative examples 1 and 2, HOMO suitable for hole transporting layer was formed, 2) a heterocycle containing no oxygen substitution in comparison with comparative examples 3 and 4 was formed, and thus chemical durability was excellent, and 3) the aryl group on the other side of the aryl group of the aryl amine was minimized to C in comparison with comparative example 5 16 The following aryl group is not a branched aryl group, and thus maintains proper HOMO and LUMO and high T1, 4), and the molecular arrangement and film formation between the branched aryl group and the amine become excellent due to the introduction of arylene group, and thus has rapid hole mobility, and thus it is understood that in the case where the compound of the present invention is applied to an organic light emitting device, the driving voltage is low, and efficiency and lifetime are greatly improved, as compared with comparative examples 6 to 9.
The above description of the present invention is for illustrative purposes, and those skilled in the art to which the present invention pertains will appreciate that it can be easily modified in other specific ways without changing the technical idea or essential features of the present invention. Accordingly, it should be understood that the various embodiments described above are illustrative in all respects, rather than restrictive. For example, each constituent element described as a single type may be implemented in a distributed manner, and a plurality of constituent elements described as distributed may be implemented in a combined manner.
The scope of the invention is indicated by the appended claims rather than by the foregoing detailed description, and all changes and modifications that come within the meaning and range of equivalency of the claims and are therefore intended to be embraced therein.

Claims (10)

1. A compound characterized by being represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
Ar 1 is a phenyl group, and is a phenyl group,
Ar 2 and Ar is a group 3 Each independently is phenyl, naphthyl, or biphenyl,
Ar 4 is a phenyl group or a naphthyl group,
Ar 5 is a phenyl group, and is a phenyl group,
r and R' are each independently hydrogen, deuterium, methyl, ethyl, propyl, phenyl, naphthyl, or biphenyl,
R 1 r is R 2 Each independently is hydrogen, heavy hydrogen, methyl, ethyl, propyl, phenyl, naphthyl, or biphenyl,
l is phenylene or biphenylene, and is a group,
l is 0 or an integer from 1 to 4, m is 0 or 1, n is 0 or 1, o is 1,
provided that when Ar 4 In the case of naphthyl, n is 0.
2. The compound according to claim 1, wherein the compound is represented by the following chemical formula 2:
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
Ar 1 to Ar 4 、R、R`、R 1 、R 2 L, m and o are as defined in claim 1.
3. The compound according to claim 2, wherein the compound is represented by the following chemical formula 3:
chemical formula 3
In the chemical formula 3 described above, the chemical formula,
Ar 1 to Ar 3 、R、R`、R 1 、R 2 L, l and m are as defined in claim 1,
R 3 is a hydrogen gas which is used as a hydrogen gas,
p is 0 or 1.
4. A compound according to claim 3, characterized in that the compound is represented by the following chemical formula 4:
chemical formula 4
In the chemical formula 4 described above, the chemical formula,
Ar 1 to Ar 3 、R 1 、R 2 L, l and m are as defined in claim 1,
R 3 is a hydrogen gas which is used as a hydrogen gas,
p is either 0 or 1 and,
ar and Ar' are each independently phenyl, naphthyl, or biphenyl.
5. The compound according to claim 4, wherein the compound is represented by the following chemical formula 5:
chemical formula 5
In the chemical formula 5 described above, in which the chemical formula is shown in the drawing,
Ar 1 to Ar 3 、R 1 、R 2 L, l and m are as defined in claim 1,
R 3 is a hydrogen gas which is used as a hydrogen gas,
p is either 0 or 1 and,
R 4 r is R 5 Each independently is hydrogen.
6. The compound of claim 5, wherein the compound is represented by the following chemical formula 6:
chemical formula 6
In the chemical formula 6 described above, the chemical formula,
Ar 2 、Ar 3 、R 1 、R 2 l and m are as defined in claim 1,
R 3 is a hydrogen gas which is used as a hydrogen gas,
p is either 0 or 1 and,
R 4 r is R 5 Each independently is hydrogen.
7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is one of the following compounds:
8. an organic light-emitting device comprising an organic layer comprising the compound of claim 1 between a first electrode and a second electrode.
9. The organic light-emitting device according to claim 8, wherein the organic layer is 1 or more layers of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.
10. The organic light-emitting device according to claim 9, wherein the organic layer is a light-emitting auxiliary layer.
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Publication number Priority date Publication date Assignee Title
KR102559469B1 (en) * 2017-07-07 2023-07-25 주식회사 동진쎄미켐 Novel compound and organic electroluminescent divice including the same
JP7406486B2 (en) 2018-06-25 2023-12-27 保土谷化学工業株式会社 Compounds with triarylamine structure and organic electroluminescent devices
KR102041137B1 (en) * 2019-04-02 2019-11-07 머티어리얼사이언스 주식회사 Organic compound and organic electroluminescent device comprising the same
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110076271A (en) * 2009-12-29 2011-07-06 주식회사 알파켐 Fluoranthene derivatives and organic electroluminescent device using the same
CN102596907A (en) * 2009-11-16 2012-07-18 出光兴产株式会社 aromatic amine derivative and organic electroluminescent element using same
CN104583176A (en) * 2012-08-31 2015-04-29 出光兴产株式会社 Aromatic amine derivative and organic electroluminescent element using same
WO2016186276A1 (en) * 2015-05-20 2016-11-24 삼성에스디아이 주식회사 Organic compound, organic optoelectronic element, and display device
WO2016199743A1 (en) * 2015-06-11 2016-12-15 保土谷化学工業株式会社 Arylamine compound and organic electroluminescent element
CN106573905A (en) * 2014-08-04 2017-04-19 东进世美肯株式会社 Novel compound and orgarnic light emitting device containing same
CN106848072A (en) * 2015-11-24 2017-06-13 东进世美肯株式会社 Organic illuminating element
CN106831313A (en) * 2017-01-25 2017-06-13 上海道亦化工科技有限公司 A kind of compound and its organic electroluminescence device with triaryl naphthalene

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6674734B2 (en) * 2014-10-29 2020-04-01 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Organic electroluminescent element material and organic electroluminescent element using the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102596907A (en) * 2009-11-16 2012-07-18 出光兴产株式会社 aromatic amine derivative and organic electroluminescent element using same
KR20110076271A (en) * 2009-12-29 2011-07-06 주식회사 알파켐 Fluoranthene derivatives and organic electroluminescent device using the same
CN104583176A (en) * 2012-08-31 2015-04-29 出光兴产株式会社 Aromatic amine derivative and organic electroluminescent element using same
CN106573905A (en) * 2014-08-04 2017-04-19 东进世美肯株式会社 Novel compound and orgarnic light emitting device containing same
WO2016186276A1 (en) * 2015-05-20 2016-11-24 삼성에스디아이 주식회사 Organic compound, organic optoelectronic element, and display device
WO2016199743A1 (en) * 2015-06-11 2016-12-15 保土谷化学工業株式会社 Arylamine compound and organic electroluminescent element
CN106848072A (en) * 2015-11-24 2017-06-13 东进世美肯株式会社 Organic illuminating element
CN106831313A (en) * 2017-01-25 2017-06-13 上海道亦化工科技有限公司 A kind of compound and its organic electroluminescence device with triaryl naphthalene

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
New hole-transporting amorphous molecular materials with high glass-transition temperatures for organic light-emitting diodes;Kenji Okumoto, et al.;《Proceedings of SPIE-The International Society for Optical Engineering》;20071231;665508/1-665508/8 *

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