WO2021085817A2 - Dérivé d'amine tertiaire et dispositif électroluminescent organique le comprenant - Google Patents

Dérivé d'amine tertiaire et dispositif électroluminescent organique le comprenant Download PDF

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WO2021085817A2
WO2021085817A2 PCT/KR2020/010960 KR2020010960W WO2021085817A2 WO 2021085817 A2 WO2021085817 A2 WO 2021085817A2 KR 2020010960 W KR2020010960 W KR 2020010960W WO 2021085817 A2 WO2021085817 A2 WO 2021085817A2
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WO2021085817A3 (fr
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석문기
고병수
임철수
박용필
한갑종
오유진
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주식회사 랩토
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Priority to CN202080076161.2A priority Critical patent/CN114641469A/zh
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    • C—CHEMISTRY; METALLURGY
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero 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
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    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses

Definitions

  • the present invention relates to a tertiary amine derivative and an organic electroluminescent device including the same, wherein the organic electroluminescent device including a capping layer by the tertiary amine derivative has a high refractive index characteristic and an ultraviolet absorption characteristic at the same time.
  • LCD Liquid Crystal Display
  • OLED Organic Light Emitting Diodes
  • the basic structure of an OLED display is generally an anode, a hole injection layer (HIL), a hole transporting layer (HTL), an emission layer (EML), an electron transporting layer, and It is composed of a multilayer structure of ETL) and a cathode, and has a sandwich structure in which an electronic organic multilayer film is formed between two electrodes.
  • HIL hole injection layer
  • HTL hole transporting layer
  • EML emission layer
  • ETL electron transporting layer
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • organic light emitting device when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.
  • organic light emitting devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.
  • Materials used as the organic material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.
  • Light-emitting materials include blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors depending on the light-emitting color.
  • a host/dopant system may be used as a luminescent material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host mainly constituting the light emitting layer and having excellent light emission efficiency is mixed in a light emitting layer, excitons generated from the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
  • organic light emitting devices In order to sufficiently express the excellent characteristics of the above-described organic light emitting device, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., have been developed. The performance of organic light emitting devices is recognized by products.
  • the organic light emitting device is exposed to an external light source, so it is in an environment exposed to ultraviolet rays having high energy. Accordingly, there is a problem that the organic material constituting the organic light emitting device is continuously affected. In order to prevent exposure to such a high-energy light source, the problem can be solved by applying a capping layer having ultraviolet absorption characteristics to the organic light-emitting device.
  • the efficiency of an organic light-emitting device can be generally divided into internal luminescent efficiency and external luminescent efficiency.
  • the internal luminous efficiency is related to the efficiency of the formation of excitons in the organic layer in order to perform light conversion.
  • External luminous efficiency refers to the efficiency in which light generated in the organic layer is emitted to the outside of the organic light-emitting device.
  • CPL capping layer
  • the present invention is a first electrode; An organic material layer disposed on the first electrode; A second electrode disposed on the organic material layer; And a capping layer disposed on the second electrode, wherein the organic material layer or the capping layer provides an organic electroluminescent device including a tertiary amine derivative represented by Formula 1 below.
  • Z 1 is O or S
  • n, p and q are each independently 0 or 1
  • Ar 1 and Ar 2 are the same as each other, and a cyano group; An aryl group substituted with a cyano group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoxazole group; And a substituted or unsubstituted benzthiazole group; It is any one selected from among.
  • the compound described in the present specification may be used as a material for an organic material layer or a capping layer of an organic light-emitting device.
  • the compound according to the present invention exhibits ultraviolet absorption characteristics, thereby minimizing damage to organic materials in the organic light-emitting device by an external light source, and improving efficiency, low driving voltage, and/or lifespan characteristics in the organic light-emitting device.
  • a first electrode 110 is a first electrode 110, a hole injection layer 210, a hole transport layer 215, a light emitting layer 220, an electron transport layer 230, an electron injection layer on the substrate 100 according to an embodiment of the present invention.
  • 235, a second electrode 120, and a capping layer 300 are sequentially stacked on an organic light-emitting device.
  • FIG. 2 is a graph of light refraction and absorption characteristics when a tertiary amine derivative according to an embodiment of the present invention is used.
  • first and second may be used to describe various elements, but the elements should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another component. For example, without departing from the scope of the present invention, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element. Singular expressions include plural expressions unless the context clearly indicates otherwise.
  • substituted or unsubstituted refers to a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a hydroxy group, a silyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkoxy group, an alke It may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a nil group, an aryl group, a hetero aryl group, and a heterocyclic group.
  • each of the substituents exemplified above may be substituted or unsubstituted.
  • the biphenyl group may be interpreted as an aryl group, or may be interpreted as a phenyl group substituted with a phenyl group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • the alkyl group may be linear, branched or cyclic.
  • the number of carbon atoms in the alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methyl
  • a hydrocarbon ring group means any functional group or substituent derived from an aliphatic hydrocarbon ring.
  • the hydrocarbon cyclic group may be a saturated hydrocarbon cyclic group having 5 to 20 ring carbon atoms.
  • an aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the number of ring carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less.
  • aryl groups include phenyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, quincphenyl group, sexyphenyl group, triphenylenyl group, pyrenyl group, peryleneyl group, naphtha
  • a senyl group, a pyrenyl group, a benzofluoranthenyl group, a chrysenyl group, etc. can be illustrated, it is not limited to these.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heteroaryl group may be a heteroaryl group including one or more of O, N, P, Si, and S as heterogeneous elements.
  • the N and S atoms may be oxidized in some cases, and the N atom(s) may be quaternized in some cases.
  • the number of ring carbon atoms in the heteroaryl group is 2 or more and 30 or less or 2 or more and 20 or less.
  • the heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the polycyclic heteroaryl group may have, for example, a bicyclic or tricyclic structure.
  • heteroaryl group examples include thiophene group, furan group, pyrrole group, imidazole group, pyrazolyl group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group , Tetrazine group, triazole group, tetrazole group, acridyl group, pyridazine group, pyrazinyl group, quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyrido pyrimidine group, pyrido pyrazino Pyrazine group, isoquinoline group, cinnoly group, indole group, isoindole group, indazole group, carbazole group, N-aryl carbazole group, N-heteroaryl carbazole group, N-alkyl
  • N-oxide aryl groups corresponding to the monocyclic hetero aryl group or polycyclic hetero aryl group for example, quaternary salts such as a pyridyl N-oxide group and a quinolyl N-oxide group. Not limited.
  • the silyl group includes an alkyl silyl group and an aryl silyl group.
  • the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Not limited.
  • the boron group includes an alkyl boron group and an aryl boron group.
  • the boron group include, but are not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, diphenyl boron group, and phenyl boron group.
  • the alkenyl group may be linear or branched.
  • the number of carbon atoms is not particularly limited, but is 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.
  • Examples of the alkenyl group include, but are not limited to, a vinyl group, 1-butenyl group, 1-pentenyl group, 1,3-butadienyl aryl group, styrenyl group, and styrylvinyl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, and may include a polycyclic aryl group or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • aryl amine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthylamine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group, but are not limited thereto.
  • examples of the heteroallylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group.
  • the heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.
  • an arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • adjacent group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, another substituent substituted on an atom where the corresponding substituent is substituted, or a substituent that is three-dimensionally adjacent to the substituent.
  • two methyl groups can be interpreted as “adjacent groups”
  • 1,1-diethylcyclopentene 2
  • the two ethyl groups can be interpreted as “adjacent groups” to each other.
  • the tertiary amine derivative compound according to an embodiment of the present invention is represented by the following formula (1).
  • Z 1 is O or S
  • n, p and q are each independently 0 or 1
  • Ar 1 and Ar 2 are the same as each other, and a cyano group; An aryl group substituted with a cyano group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoxazole group; And a substituted or unsubstituted benzthiazole group; It is any one selected from among.
  • the tertiary amine derivative represented by Formula 1 may be any one selected from compounds represented by Formula 2 below, and the following compounds may be further substituted.
  • FIG. 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment of the present invention.
  • a first electrode 110 a hole injection layer 210, a hole transport layer 215, a light emitting layer 220, and an electron are sequentially stacked on a substrate 100.
  • a transport layer 230, an electron injection layer 235, a second electrode 120, and a capping layer 300 may be included.
  • the first electrode 110 and the second electrode 120 are disposed to face each other, and the organic material layer 200 may be disposed between the first electrode 110 and the second electrode 120.
  • the organic material layer 200 may include a hole injection layer 210, a hole transport layer 215, a light emitting layer 220, an electron transport layer 230, and an electron injection layer 235.
  • the capping layer 300 presented in the present invention is a functional layer deposited on the second electrode 120 and includes an organic material according to Formula 1 of the present invention.
  • the first electrode 110 has conductivity.
  • the first electrode 110 may be formed of a metal alloy or a conductive compound.
  • the first electrode 110 is generally an anode, but its function as an electrode is not limited.
  • the first electrode 110 may be formed on the substrate 100 by using an electrode material deposition method, an electron beam evaporation method, or a sputtering method.
  • the material of the first electrode 110 may be selected from materials having a high work function to facilitate injection of holes into the organic light-emitting device.
  • the capping layer 300 proposed in the present invention is applied when the emission direction of the organic light-emitting device is front emission, and thus, the first electrode 110 uses a reflective electrode.
  • These materials include Mg (magnesium), Al (aluminum), Al-Li (aluminum-lithium), Ca (calcium), Mg-In (magnesium-indium), and Mg-Ag (magnesium-silver), which are not oxides. It can also be made using the same metal.
  • carbon substrate flexible electrode materials such as CNT (carbon nanotube) and graphene (graphene) may be used.
  • the organic material layer 200 may be formed of a plurality of layers.
  • the organic material layer 200 includes a hole transport region 210 to 215 disposed on the first electrode 110, a light emitting layer 220 disposed on the hole transport region, and the light emitting layer
  • the electron transport regions 230 to 235 disposed on the 220 may be included.
  • the capping layer 300 includes an organic compound represented by Formula 1 to be described later.
  • the hole transport regions 210 to 215 are provided on the first electrode 110.
  • the hole transport regions 210 to 215 may include at least one of a hole injection layer 210, a hole transport layer 215, a hole buffer layer, and an electron blocking layer (EBL). It plays a role and generally has a thicker thickness than the electron transport region because the hole mobility is faster than the electron mobility.
  • EBL electron blocking layer
  • the hole transport regions 210 to 215 may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the hole transport regions 210 to 215 may have a single layer structure of the hole injection layer 210 or the hole transport layer 215, or may have a single layer structure made of a hole injection material and a hole transport material. have.
  • the hole transport regions 210 to 215 have a single-layer structure made of a plurality of different materials, or a hole injection layer 210/hole transport layer 215 sequentially stacked from the first electrode 110, Hole injection layer 210 / hole transport layer 215 / hole buffer layer, hole injection layer 210 / hole buffer layer, hole transport layer 215 / hole buffer layer, or hole injection layer 210 / hole transport layer 215 / electron
  • EBL blocking layer
  • the hole injection layer 210 may be formed on the anode by various methods such as a vacuum deposition method, a spin coating method, a cast method, and an LB method.
  • the deposition conditions are 100 to 500 depending on the compound used as the material of the hole injection layer 210 and the structure and thermal characteristics of the hole injection layer 210.
  • the deposition rate at °C can be freely controlled by around 1 ⁇ /s, and is not limited to specific conditions.
  • the coating conditions are different depending on the characteristics between the compound used as the material of the hole injection layer 210 and the layers formed as the interface, but the coating speed and coating are used for even film formation. After the solvent is removed, heat treatment or the like is required.
  • the hole transport regions 210 to 215 are, for example, m-MTDATA, TDATA, 2-TNATA, NPB, ⁇ -NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, and TCTA.
  • the hole transport regions 210 to 215 may have a thickness of about 100 to about 10,000 ⁇ , and the organic material layers of each hole transport region 210 to 215 are not limited to the same thickness. For example, if the thickness of the hole injection layer 210 is 50 ⁇ , the thickness of the hole transport layer 215 may be 1000 ⁇ , and the thickness of the electron blocking layer may be 500 ⁇ .
  • the thickness condition of the hole transport regions 210 to 215 may be set to a degree that satisfies the efficiency and lifetime within a range in which the increase in the driving voltage of the organic light emitting device does not increase.
  • the organic material layer 200 includes a hole injection layer 210, a hole transport layer 215, a functional layer having a hole injection function and a hole transport function at the same time, a buffer layer, an electron blocking layer, a light emitting layer 220, a hole blocking layer, an electron transport layer ( 230), an electron injection layer 235, and one or more layers selected from the group consisting of a functional layer having an electron transport function and an electron injection function at the same time.
  • the hole transport regions 210 to 215 may use doping to improve characteristics like the light emitting layer 220, and doping of a charge-generating material into the hole transport regions 210 to 215 will improve the electrical properties of the organic light emitting device. I can.
  • the charge-generating material is generally composed of a material having very low HOMO and LUMO.
  • the LUMO of the charge-generating material has a similar value to that of the hole transport layer 215 material. Due to such a low LUMO, the electrons of the LUMO are vacant, and holes are easily transferred to the adjacent hole transport layer 215 to improve electrical characteristics.
  • the charge-generating material may be, for example, a p-dopant.
  • the p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.
  • the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane Quinone derivatives such as phosphorus (F4-TCNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; Cyano group-containing compounds; And the like, but are not limited thereto.
  • the hole transport regions 210 to 215 may further include a charge generating material to improve conductivity.
  • the charge generating material may be uniformly or non-uniformly dispersed in the hole transport regions 210 to 215.
  • the charge generating material may be, for example, a p-dopant.
  • the p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.
  • p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and the like. However, it is not limited thereto.
  • the hole transport regions 210 to 215 may further include at least one of a hole buffer layer and an electron blocking layer in addition to the hole injection layer 210 and the hole transport layer 215.
  • the hole buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer 220.
  • a material included in the hole buffer layer a material capable of being included in the hole transport regions 210 to 215 may be used.
  • the electron blocking layer is a layer that serves to prevent injection of electrons from the electron transport regions 230 to 235 to the hole transport regions 210 to 215.
  • the electron blocking layer may use a material having a high T1 value so as not only to block electrons moving to the hole transport region, but also to prevent the excitons formed in the light emitting layer 220 from diffusing into the hole transport regions 210 to 215.
  • a host of the light emitting layer 220 having a high T 1 value may be used as a material for the electron blocking layer.
  • the emission layer 220 is provided on the hole transport regions 210 to 215.
  • the emission layer 220 may have a thickness of, for example, about 100 ⁇ to about 1000 ⁇ or about 100 ⁇ to about 300 ⁇ .
  • the emission layer 220 may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the light emitting layer 220 is a region where holes and electrons meet to form excitons, and the material forming the light emitting layer 220 must have an appropriate energy band gap to exhibit high light emission characteristics and a desired light emission color, and generally play two roles as a host and a dopant.
  • Eggplant is made of two materials, but is not limited thereto.
  • the host may include at least one of the following TPBi, TBADN, ADN (also referred to as "DNA”), CBP, CDBP, TCP, and mCP, and if the characteristics are appropriate, the material is not limited thereto.
  • the dopant of the emission layer 220 may be an organic metal complex.
  • the content of a general dopant may be selected from 0.01 to 20%, and is not limited thereto in some cases.
  • the electron transport regions 230 to 235 are provided on the emission layer 220.
  • the electron transport regions 230 to 235 may include at least one of a hole blocking layer, an electron transport layer 230 and an electron injection layer 235, but is not limited thereto.
  • the electron transport regions 230 to 235 may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.
  • the electron transport regions 230 to 235 may have a single layer structure of the electron injection layer 235 or the electron transport layer 230, or may have a single layer structure made of an electron injection material and an electron transport material. have.
  • the electron transport regions 230 to 235 have a single layer structure made of a plurality of different materials, or an electron transport layer 230 / electron injection layer 235 sequentially stacked from the light emitting layer 220, and hole blocking.
  • the layer/electron transport layer 230/electron injection layer 235 may have a structure, but is not limited thereto.
  • the thickness of the electron transport regions 230 to 235 may be, for example, about 1000 ⁇ to about 1500 ⁇ .
  • the electron transport regions 230 to 235 are various such as vacuum evaporation method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser induced thermal imaging (LITI), etc. It can be formed using a method.
  • the electron transport region 230 may include an anthracene compound.
  • the electron transport region is, for example, Alq3(Tris(8-hydroxyquinolinato)aluminum),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2 ,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10 -dinaphthylanthracene,TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl),BCP(2,9-Dimethyl-4,7-diphenyl-1,10- phenanthroline),Bphen(4,7-Diphen
  • the electron transport layer 230 is selected as a material having a fast electron mobility or a slow electron mobility according to the structure of the organic light emitting device, it is necessary to select a variety of materials, and in some cases, the following Liq or Li may be doped.
  • the electron transport layers 230 may have a thickness of about 100 ⁇ to about 1000 ⁇ , for example, about 150 ⁇ to about 500 ⁇ . When the thickness of the electron transport layers 230 satisfies the above-described range, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.
  • the electron transport regions 230 to 235 include the electron injection layer 235
  • the electron transport regions 230 to 235 select a metal material that facilitates injection of electrons, and LiF, LiQ (Lithium quinolate), Lanthanum group metals such as Li 2 O, BaO, NaCl, CsF, and Yb, or halogenated metals such as RbCl and RbI may be used, but are not limited thereto.
  • the electron injection layer 235 may also be formed of a material in which an electron transport material and an insulating organo metal salt are mixed.
  • the organometallic salt may be a material having an energy band gap of approximately 4 eV or more.
  • the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. I can.
  • the electron injection layers 235 may have a thickness of about 1 ⁇ to about 100 ⁇ , and about 3 ⁇ to about 90 ⁇ . When the thickness of the electron injection layers 235 satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
  • the electron transport regions 230 to 235 may include a hole blocking layer.
  • the hole blocking layer includes, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), and Balq It can be, but is not limited thereto.
  • the second electrode 120 is provided on the electron transport regions 230 to 235.
  • the second electrode 120 may be a common electrode or a cathode.
  • the second electrode 120 may be a transmissive electrode or a transflective electrode.
  • the second electrode 120 may be used in combination with a metal having a relatively low work function, an electroconductive compound, an alloy, and the like.
  • the second electrode 120 is a transflective electrode or a reflective electrode.
  • the second electrode 120 is Li (lithium), Mg (magnesium), Al (aluminum), Al-Li (aluminum-lithium), Ca (calcium), Mg-In (magnesium-indium), Mg-Ag (magnesium -Silver) or a compound or mixture containing them (eg, a mixture of Ag and Mg).
  • a plurality of layer structures including a reflective film or a semi-transmissive film formed of the material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • ZnO zinc oxide
  • ITZO indium tin zinc oxide
  • the second electrode 120 may be connected to the auxiliary electrode.
  • the resistance of the second electrode 120 may be reduced.
  • a hard or soft material may be used as the material of the substrate 100.
  • the hard material is soda lime glass, alkali-free glass, aluminosilicate glass PC (polycarbonate), PES (polyethersulfone), COC (cyclic olefin copolymer), PET (polyethylene terephthalate), PEN (polyethylene naphthalate), etc. can be used as the soft material. .
  • the organic light emitting diode As voltages are applied to the first electrode 110 and the second electrode 120, respectively, holes injected from the first electrode 110 pass through the hole transport regions 210 to 215 and the emission layer The electrons are moved to 220, and electrons injected from the second electrode 120 are transferred to the emission layer 220 through the electron transport regions 230 to 235. The electrons and holes recombine in the emission layer 220 to generate excitons, and the excitons fall from the excited state to the ground state to emit light.
  • the light path generated in the light emitting layer 220 may exhibit very different trends depending on the refractive indexes of organic and inorganic materials constituting the organic light emitting device.
  • Light passing through the second electrode 120 may pass only light transmitted at an angle smaller than the critical angle of the second electrode 120.
  • light that contacts the second electrode 120 greater than the critical angle is totally reflected or reflected, and thus cannot be emitted to the outside of the organic light-emitting device.
  • the refractive index of the capping layer 300 When the refractive index of the capping layer 300 is high, it contributes to the improvement of luminous efficiency by reducing such total reflection or reflection, and when it has an appropriate thickness, it contributes to high efficiency improvement and color purity by maximizing the micro-cavity phenomenon. .
  • the capping layer 300 is positioned on the outermost side of the organic light-emitting device, and does not affect the driving of the device at all and has a profound effect on device characteristics. Therefore, the capping layer 300 is important from both viewpoints of improving device characteristics as well as an internal protection role of an organic light-emitting device.
  • Organic materials absorb light energy in a specific wavelength range, which depends on the energy band gap. If the energy band gap is adjusted for the purpose of absorption of the UV region that may affect organic materials inside the organic light emitting device, the capping layer 300 can be used for the purpose of protecting the organic light emitting device including improving optical properties. have.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the obtained compound was dissolved in 100 mL of tetrahydrofuran, slowly acidified (pH ⁇ 2) with a 4N hydrochloric acid solution, and stirred at 50° C. for 4 hours. After cooling to room temperature, tetrahydrofuran was removed by distillation under reduced pressure, and diethyl ether was added thereto, followed by stirring. The resulting solid was filtered under reduced pressure, and the filtered wet body was suspended in 200 mL of water, and the acidity was adjusted to 8 or more with a saturated sodium carbonate solution, followed by stirring for 1 hour. The resulting solid was filtered, washed with water, and dried under reduced pressure. The obtained compound was purified by column chromatography to obtain 5.0 g (yield: 67%) of a compound (intermediate (1)).
  • the resulting precipitate was filtered under reduced pressure and washed with chloroform.
  • the filtered wet body was suspended in 600 mL of water, and the pH was adjusted to 8 or higher with saturated sodium carbonate solution, followed by extraction with chloroform and layer separation.
  • the separated chloroform layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.
  • the concentrated residue was slurried with dichloromethane and normal hexane to obtain 28.0 g (yield: 58%) of a yellow solid compound (intermediate (3)).
  • the filtered wet body was basified (pH>8) with saturated sodium carbonate solution and extracted with 190 mL of dichloromethane. The separated organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain 3.6 g (yield: 47.6%) of a pale orange solid compound (intermediate (5)).
  • the filtered wet body was dissolved in 70 mL of tetrahydrofuran, 30 mL of 6N hydrochloric acid was added, and the mixture was stirred for 1 hour.
  • the mixture was basified (pH 7-8) with saturated sodium carbonate solution and extracted with dichloromethane.
  • the separated organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain 2.72 g (yield: 59.9%) of a brown solid compound (intermediate (6)).
  • the resulting precipitate was filtered under reduced pressure and washed with chloroform.
  • the filtered wet body was suspended in 600 mL of water, and the pH was adjusted to 8 or higher with saturated sodium carbonate solution, followed by extraction with chloroform and layer separation.
  • the separated chloroform layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.
  • the concentrated residue was slurried with dichloromethane and normal hexane to obtain 28.0 g (yield: 58%) of a yellow solid compound (intermediate (8)).
  • 6-hydroxy-2-naphthonitrile 6-Hydroxy-2-naphthonitrile 10.0 g (59.1 mmol) was dissolved in dichloromethane (DCM) 300 mL, and pyridine (Pyridine) 14.0 g (177.3 mmol) was added dropwise. The temperature was lowered to 0°C. Tf 2 O 20.0 g (70.9 mmol) was slowly added dropwise, and the temperature was raised to room temperature, followed by reaction for 12 hours.
  • DCM dichloromethane
  • reaction mixture was cooled to room temperature, filtered through a pad of Celite, and distilled under reduced pressure to remove the solvent.
  • the obtained mixture was purified by column chromatography to obtain 3.1 g (yield: 66.2%) of compound 2-48 (LT18-30-263) as a brown solid.
  • intermediate (3) 5.0 g (19.3 mmol), intermediate (11) 12.2 g (40.5 mmol), Pd (dba) 2 1.1 mg (1.9 mmol), 50% t-Bu 3 P 1.6 g ( 3.9 mmol), NaOtBu 5.6 g (57.9 mmol) and Xylene 80 mL were added and mixed, and then reacted at 120° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, extracted with chloroform, and the solvent was removed under reduced pressure.
  • intermediate (13) 5.0 g (18.2 mmol), intermediate (11) 11.5 g (38.1 mmol), Pd (dba) 2 1.0 mg (1.8 mmol), 50% t-Bu 3 P 1.5 g ( 3.6 mmol), 5.2 g (54.5 mmol) of NaOtBu, and 80 mL of Xylene were added and mixed, and then reacted at 120° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, extracted with chloroform, and the solvent was removed under reduced pressure.
  • the obtained compound was purified by silica gel column chromatography (Hex:EA), dissolved in acetone, and then solidified while slowly adding methanol dropwise to obtain 1.1 g (yield: 10.5%) of a yellow solid compound 2-153 (LT20-35-365). Got it.
  • J.A. Measure n (refractive index) and k (extinction coefficient) using WOOLLAM's Ellipsometer.
  • the glass substrate (0.7T) was washed in Ethanol, DI Water, and Acetone for 10 minutes each, followed by oxygen plasma treatment on the glass substrate for 2 minutes at 125 W at 2 ⁇ 10 -2 Torr and 9 ⁇ 10 to deposit the compound on the glass substrate at a vacuum degree of 7 Torr at a rate of 1 ⁇ / sec 800 ⁇ it will be produced danmak.
  • REF01 was used as a compound in the preparation of a single film for evaluation of optical properties.
  • Table 1 shows the optical properties of the compounds according to Comparative Test Examples and Test Examples 1 to 17.
  • Optical properties are the refractive index constant at 450 nm and 620 nm wavelength and the absorption constant at 380 nm wavelength.
  • n values in the blue region (450 nm) and red region (620 nm) of Comparative Test Example (REF01) were 2.000 and 1.846, respectively, whereas most of the compounds according to the present invention were As a result, it was confirmed to have a higher refractive index than Comparative Test Example compound (REF01) in the blue region, green region, and red region. This satisfies the high refractive index value required to secure a high viewing angle in the blue region.
  • the k value at 380 nm corresponding to the starting stage of the UV region was also high in most of the example compounds. This may contribute to substantially improving the lifespan of the organic electroluminescent device by effectively absorbing the high-energy external light source in the UV region and minimizing damage to organic materials inside the organic light-emitting device.
  • ITO a transparent electrode
  • 2-TNATA was used as the hole injection layer
  • NPB was the hole transport layer
  • ⁇ -ADN was the host of the emission layer
  • Pyene-CN was the blue fluorescent dopant
  • Liq was the electron injection layer
  • Mg:Ag was used as a negative electrode.
  • the structures of these compounds are as shown in the following formula.
  • Blue fluorescent organic light emitting device is ITO (180 nm) / 2-TNATA (60 nm) / NPB (20 nm) / ⁇ -ADN:Pyrene-CN 10% (30 nm) / Alq 3 (30 nm) / Liq (2 nm) / Mg:Ag (1:9, 10 nm) / REF (60nm) was deposited in the order to fabricate a device. Before depositing the organic substance is applied to the ITO electrodes 2 ⁇ 10 - was for 2 minutes plasma treatment to 125W at 2 Torr.
  • Organics are 9 ⁇ 10 - were deposited at a vacuum degree of 7 Torr, Liq was 0.1 ⁇ / sec, ⁇ -ADN is 0.18 ⁇ / on the basis of sec Pyrene-CN was co-deposited with 0.02 ⁇ / sec, all the remaining organics were 1 It was deposited at a rate of ⁇ /sec.
  • the capping layer material used in the experiment was selected as REF01. After the device was manufactured, the device was sealed in a glove box filled with nitrogen gas to prevent contact with air and moisture. After forming a partition wall with 3M's adhesive tape, barium oxide, a moisture absorbent that can remove moisture, was added and a glass plate was attached.
  • Table 2 shows the electroluminescence characteristics of the organic light emitting devices prepared in Comparative Examples and Examples 1 to 17.
  • the tertiary amine derivative compound according to the present invention can be used as a material for the capping layer of organic electronic devices including organic light emitting devices, and organic electronic devices including organic light emitting devices using the same have efficiency and driving voltage. It can be seen that it exhibits excellent properties in terms of stability, etc. In particular, the compound according to the present invention exhibited high efficiency characteristics due to excellent micro-cavity capability.
  • the compound of Formula 1 has surprisingly desirable properties for use as a capping layer in OLED.
  • the compounds of the present invention can be applied to industrial organic electronic device products due to these properties.
  • the above synthesis example is an example, and the reaction conditions may be changed as necessary.
  • the compound according to an embodiment of the present invention may be synthesized to have various substituents using methods and materials known in the art. By introducing various substituents to the core structure represented by Chemical Formula 1, it may have properties suitable for use in an organic electroluminescent device.
  • the tertiary amine derivative compound according to the present invention may be used to improve the quality of an organic electroluminescent device by being used for an organic material layer and/or a capping layer of an organic electroluminescent device.
  • the organic electroluminescent device When the compound is used for the capping layer, the organic electroluminescent device exhibits its original characteristics and at the same time, the lifespan can be improved by the optical characteristics of the compound.

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Abstract

L'invention concerne un dérivé d'amine tertiaire absorbant efficacement une source de lumière extérieure à haute énergie dans une région UV de façon à réduire au minimum les dommages subis par des matériaux organiques dans un dispositif électroluminescent organique, ce qui contribue à une amélioration sensible de la durée de vie du dispositif électroluminescent organique. Un dispositif électroluminescent organique selon la présente invention comprend : une première électrode ; une seconde électrode ; et une ou plusieurs couches de matériaux organiques disposées entre la première électrode et la seconde électrode ; et une couche de recouvrement, la couche de recouvrement comprenant un dérivé d'amine tertiaire représenté par la formule chimique 1 selon la présente invention.
PCT/KR2020/010960 2019-10-31 2020-08-18 Dérivé d'amine tertiaire et dispositif électroluminescent organique le comprenant WO2021085817A2 (fr)

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CN114057718A (zh) * 2022-01-17 2022-02-18 浙江华显光电科技有限公司 三苯胺衍生物、制剂、有机光电器件及显示或照明装置

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KR101379133B1 (ko) * 2008-05-29 2014-03-28 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 그들을 사용한 유기 전기발광 소자
WO2014104144A1 (fr) * 2012-12-26 2014-07-03 出光興産株式会社 Composé amine à cycles condensés contenant de l'oxygène, composé amine à cycles condensés contenant du soufre et élément électroluminescent organique
CN108699438B (zh) * 2016-03-03 2021-11-30 默克专利有限公司 用于有机电致发光器件的材料
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