WO2015001726A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2015001726A1
WO2015001726A1 PCT/JP2014/003169 JP2014003169W WO2015001726A1 WO 2015001726 A1 WO2015001726 A1 WO 2015001726A1 JP 2014003169 W JP2014003169 W JP 2014003169W WO 2015001726 A1 WO2015001726 A1 WO 2015001726A1
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group
substituted
unsubstituted
atom
substituent
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PCT/JP2014/003169
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Japanese (ja)
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紀昌 横山
秀一 林
直朗 樺澤
剛史 山本
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保土谷化学工業株式会社
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Priority to JP2014557916A priority Critical patent/JP5749870B1/ja
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    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/302—Details of OLEDs of OLED structures
    • H10K2102/3023—Direction of light emission
    • H10K2102/3026—Top emission
    • 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
    • H10K50/80—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
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to an organic electroluminescence element (hereinafter abbreviated as an organic EL element) which is a self-luminous element suitable for various display devices, and more particularly to an organic EL element using a specific arylamine compound.
  • the present invention relates to an organic EL element in which the light extraction efficiency is greatly improved.
  • the organic EL element is a self-luminous element, it has been actively researched because it is brighter and more visible than a liquid crystal element and can be clearly displayed.
  • a light emitting element having a top emission structure in which a metal having a high work function is used for an anode and light is emitted from the upper part has been used.
  • a light emitting element having a bottom emission structure in which the area of the light emitting part is limited by the pixel circuit, a light emitting element having a top emission structure has an advantage that a wide light emitting part can be obtained.
  • a semitransparent electrode such as LiF / Al / Ag (for example, see Non-Patent Document 2), Ca / Mg (for example, see Non-Patent Document 3), LiF / MgAg, or the like is used as a cathode.
  • the effect of the capping layer in the light emitting device having the top emission structure is that a light emitting device using Ir (ppy) 3 as a light emitting material has a current efficiency of 38 cd / A when there is no capping layer.
  • a light emitting device using Ir (ppy) 3 has a current efficiency of 38 cd / A when there is no capping layer.
  • an efficiency improvement of about 1.7 times as 64 cd / A was recognized.
  • the maximum point of transmittance and the maximum point of efficiency of the translucent electrode and the capping layer do not necessarily coincide with each other, and the maximum point of light extraction efficiency is determined by the interference effect. (For example, refer nonpatent literature 3).
  • a metal mask with high definition for the formation of the capping layer, but such a metal mask has a problem that the alignment accuracy is deteriorated due to thermal distortion. That is, ZnSe has a high melting point of 1100 ° C. or higher (see, for example, Non-Patent Document 3), and cannot be deposited at an accurate position with a high-definition mask. Many inorganic substances have high deposition temperatures and are not suitable for use with high-definition masks, and may damage the light-emitting elements themselves. Further, in the film formation by the sputtering method, the light emitting element is damaged, and therefore a capping layer containing an inorganic material cannot be used.
  • Alq 3 is a green light-emitting material or electron transport.
  • organic EL material generally used as a material, it has weak absorption in the vicinity of 450 nm used for a blue light emitting element. Therefore, in the case of a blue light emitting element, there is a problem that both the color purity is lowered and the light extraction efficiency is lowered.
  • JP-A-8-048656 Japanese Patent No. 3194657 WO2013-038627
  • the object of the present invention is to improve the device characteristics of the organic EL device, in particular, to greatly improve the light extraction efficiency, and has a high refractive index and excellent thin film stability and durability.
  • An object of the present invention is to provide an organic EL device having a capping layer made of a material that does not absorb in the wavelength regions of blue, green and red.
  • the physical properties of the capping layer material suitable for the present invention include (1) high refractive index, (2) vapor deposition and no thermal decomposition, (3) stable thin film state, 4) The glass transition temperature is high.
  • the physical characteristics of the element suitable for the present invention include (1) high light extraction efficiency, (2) no decrease in color purity, and (3) light transmission without change over time. (4) Long life can be mentioned.
  • the present inventors selected a specific arylamine compound having a high refractive index and capped the arylamine material, focusing on the excellent stability and durability of the thin film.
  • the present invention was completed.
  • the following organic EL elements are provided.
  • the capping layer is an arylamine compound represented by the following general formula (1)
  • An organic EL element including
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted Represents a substituted fused polycyclic aromatic group, and n represents an integer of 0 to 4.
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 is represented by the following structural formula (B) It is a monovalent group or has the monovalent group as a substituent.
  • R 1 , R 2 , R 3 and R 4 may be the same or different from each other, and may be a linking group, or a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, substituent.
  • R 1 , R 2 , R 3 and R 4 may be the same or different from each other and have a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group or substituent.
  • An optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, and an optionally substituted carbon A linear or branched alkenyl group having 2 to 6 atoms, an optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, or a substituent.
  • R 1 , R 3 and R 4 may be the same or different from each other, and may have a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group or substituent.
  • R 3 and R 4 is a single bond, a substituted or unsubstituted methylene group, an oxygen atom, through a sulfur atom or N-Ar 8 may be bonded to each other to form a ring .
  • Ar 6, Ar 8 May be the same or different from each other, and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • R 1 , R 2 , R 3 and R 4 may be the same or different from each other and have a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group or substituent.
  • An optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, and an optionally substituted carbon A linear or branched alkenyl group having 2 to 6 atoms, an optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, or a substituent.
  • R 1 , R 2 , R 3 and R 4 may be the same or different from each other and have a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group or substituent.
  • An optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, and an optionally substituted carbon A linear or branched alkenyl group having 2 to 6 atoms, an optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, or a substituent.
  • R 3 , R 4 , R 5 , R 6 , R 7 and R 8 may be the same or different from each other, and may be a linking group, or a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group.
  • Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, provided that Only one of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ar 5 , Ar 6 , Ar 7 is a linking group, X is a nitrogen atom, and Y is an oxygen atom Or except for the case of sulfur atoms.
  • any two of Ar 1 , Ar 2 , Ar 3 , Ar 4 are a monovalent group represented by the structural formula (B), or substituted for the monovalent group
  • the organic EL device according to 1) which is a group.
  • Ar 1 and Ar 4 are the monovalent group represented by the structural formula (B), or have the monovalent group as a substituent.
  • the organic EL element of description is the monovalent group represented by the structural formula (B), or have the monovalent group as a substituent.
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 to Ar 4 in formula (1), or “substituted or unsubstituted condensed hydrocarbon group”
  • phenanthryl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, Indolyl group, carbazolyl group, benzotriazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group Benzimidazolyl group, a pyrazolyl group, and a dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like.
  • Ar 1 and Ar 2 , or Ar 3 and Ar 4 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or N—Ar 8 to form a ring.
  • N in “N—Ar 8 ” represents a nitrogen atom
  • Ar 8 represents “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or Examples of the “substituted or unsubstituted condensed polycyclic aromatic group” include the same groups as those exemplified above, and the substituents that these groups may have are also exemplified below. Substituents can be mentioned.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 4 in the general formula (1), Specifically, deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, a linear or branched alkyl group having 1 to 6 carbon atoms such as n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms such as ethyloxy group
  • N—Ar 8 means “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted or unsubstituted aromatic complex”. It means the same as “N—Ar 8 ” defined for “ring group” or “substituted or unsubstituted condensed polycyclic aromatic group”.
  • R 1 to R 8 A linear or branched alkyl group having 1 to 6 carbon atoms which may have ", a" cycloalkyl group having 5 to 10 carbon atoms which may have a substituent "or" a substituent.
  • “Straight or branched alkenyl group having 2 to 6 carbon atoms” which may have “straight or branched alkyl group having 1 to 6 carbon atoms”, “5 to 10 carbon atoms”
  • Specific examples of the cycloalkyl group or the linear or branched alkenyl group having 2 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group , Neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group and 2-butenyl group.
  • N—Ar 8 means “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted or unsubstituted aromatic complex”. It means the same as “N—Ar 8 ” defined for “ring group” or “substituted or unsubstituted condensed polycyclic aromatic group”.
  • “substituents” are represented by R 1 to R 8. Having a straight or branched alkyl group having 1 to 6 carbon atoms "," a cycloalkyl group having 5 to 10 carbon atoms having a substituent "or” straight chain having 2 to 6 carbon atoms having a substituent "
  • the “substituent” in the “like or branched alkenyl group” is the “substituted aromatic hydrocarbon group” or “substituted aromatic heterocyclic group” represented by Ar 1 to Ar 4 in the general formula (1).
  • lifted, and the aspect which can be taken can also mention the same thing.
  • “substituents” are represented by R 1 to R 8.
  • Specific examples of the “linear or branched alkyloxy group having 1 to 6 atoms” or “cycloalkyloxy group having 5 to 10 carbon atoms” specifically include a methyloxy group, an ethyloxy group, and an n-propyloxy group.
  • N—Ar 8 means “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted or unsubstituted aromatic complex”. It means the same as “N—Ar 8 ” defined for “ring group” or “substituted or unsubstituted condensed polycyclic aromatic group”.
  • “substituents” are represented by R 1 to R 8.
  • the “substituent” in the “straight-chain or branched alkyloxy group having 1 to 6 carbon atoms” or “cycloalkyloxy group having 5 to 10 carbon atoms having a substituent” includes the above general formula (1
  • R 1 to R 8 Represented by R 1 to R 8 in the structural formulas (B), (B-1), (B-2), (B-3), (B-4), (B ′), "Aromatic hydrocarbon group”, “Aromatic heterocyclic group” in “Substituted aromatic hydrocarbon group”, “Substituted or unsubstituted aromatic heterocyclic group” or “Substituted or unsubstituted condensed polycyclic aromatic group”
  • a “condensed polycyclic aromatic group” is a “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the general formula (1), “substituted or unsubstituted aromatic group”
  • Ar 1 to Ar 4 in the general formula (1)
  • the “substituent” in the “hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” is the “substituted” represented by Ar 1 to Ar 4 in the above general formula (1).
  • the “aryloxy group” in the “substituted aryloxy group” specifically includes phenyloxy group, tolyloxy group, biphenylyloxy group, terphenylyloxy group, naphthyloxy group, anthryloxy group, phenanthryloxy group.
  • N—Ar 8 means “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted or unsubstituted aromatic complex”. It means the same as “N—Ar 8 ” defined for “ring group” or “substituted or unsubstituted condensed polycyclic aromatic group”.
  • Substituted aryloxy represented by R 1 to R 8 in the structural formulas (B), (B-1), (B-2), (B-3), (B-4), and (B ′)
  • the “substituent” in the “group” is the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycycle” represented by Ar 1 to Ar 4 in the general formula (1).
  • n represents an integer of 0 to 4, and n is preferably 0, 1 or 2, and more preferably 0 or 1.
  • at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 is the structural formula (B), or at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 is the structure
  • An embodiment having the formula (B) as a substituent, or at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 is the structural formula (B), and Ar 1 , Ar 2 , Ar 3 , Ar 4
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 Or at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 is the above-described structural formula (B), or Ar 1 , Ar 2 , Ar 3 , or Ar 4 has the structural formula (B) as a substituent, or any one of Ar 1 , Ar 2 , Ar 3 , Ar 4 is the structural formula (B)
  • Ar 1 and Ar 4 have the structural formula (B-1), (B-3) or (B-4) as a substituent.
  • the embodiment or the embodiment represented by the structural formula (B-2) is more preferable.
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 in the general formula (1) include an aromatic hydrocarbon group, a condensed polycyclic aromatic group, the structural formula (B), a thienyl group, a benzothienyl group, and a dibenzofura.
  • Nyl group and dibenzothienyl group are preferable, and phenyl group, biphenylyl group, terphenylyl group, naphthyl group, phenanthryl group, fluorenyl group, the structural formula (B), thienyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group are More preferred are a phenyl group, a biphenylyl group, a fluorenyl group, the structural formula (B), a dibenzofuranyl group, and a dibenzothienyl group.
  • Ar 5 , Ar 6 and Ar 7 in the structural formulas (B), (B-2) and (B ′) are aromatic hydrocarbon groups, condensed polycyclic aromatic groups, thienyl groups, benzothienyl groups, dibenzos A furanyl group and a dibenzothienyl group are preferable, and a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a thienyl group, a benzothienyl group, a dibenzofuranyl group, and a dibenzothienyl group are more preferable.
  • R 1 , R 2 , R 3 , R 4 , Ar 5 , Ar 6 , Ar 7 is a linking group.
  • X represents a carbon atom or a nitrogen atom
  • Y represents a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom.
  • Y when Y is an oxygen atom or a sulfur atom, Y has no Ar 7 linking group or substituent (Ar 7 does not exist), and when X and Y are nitrogen atoms, Any one of Ar 5 , Ar 6 , Ar 7 is a linking group or a substituent (no two of Ar 5 , Ar 6 , Ar 7 exist), X is a nitrogen atom and Y is a carbon atom In this case, any one of Ar 5 and Ar 6 is a linking group or a substituent (any of Ar 5 and Ar 6 does not exist).
  • Y when X is a nitrogen atom, Y is preferably a nitrogen atom.
  • the linking group of Ar 5 , Ar 6 or Ar 7 is Ar 1 , It is bonded to the carbon atom of Ar 2 , Ar 3 , Ar 4 (the structural formula (B) or (B ′) becomes a substituent of Ar 1 , Ar 2 , Ar 3 or Ar 4 ).
  • the structural formulas (B) and (B ′) when X is a carbon atom, Y is preferably a carbon atom, an oxygen atom, or a sulfur atom, and more preferably an oxygen atom or a sulfur atom.
  • the case where X is a nitrogen atom and Y is an oxygen atom or a sulfur atom is excluded from the present invention.
  • the arylamine compound represented by the general formula (1) that is preferably used in the organic EL device of the present invention is a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, or a capping layer of the organic EL device. It can be used as a constituent material.
  • the thickness of the capping layer is preferably in the range of 30 nm to 120 nm, and more preferably in the range of 40 nm to 80 nm.
  • the refractive index of the capping layer is 1.85 or more when the wavelength of light transmitted through the capping layer is in the range of 450 nm to 750 nm. More preferably.
  • the capping layer may be produced by laminating two or more different constituent materials.
  • the organic EL element of the present invention has a capping layer having a refractive index higher than that of the semi-transparent electrode provided outside the transparent or semi-transparent electrode, an organic EL element capable of greatly improving the light extraction efficiency is provided. can get.
  • the arylamine compound represented by the general formula (1) for the capping layer a film can be formed at a temperature of 400 ° C. or lower, so that the light emitting element is not damaged.
  • the light extraction efficiency of each color can be optimized using the fine mask, and can be suitably applied to a full color display, and a clear and bright image with good color purity can be displayed.
  • the organic EL element of the present invention uses a material for an organic EL element having a high refractive index and excellent thin film stability and durability as a material for the capping layer, compared with a conventional organic EL element, The light extraction efficiency can be greatly improved. Furthermore, it has become possible to realize an organic EL element with high efficiency and long life.
  • FIG. 3 is a diagram showing organic EL element configurations of Examples 10 to 13 and Comparative Example 1.
  • the arylamine compound represented by the general formula (1) that is suitably used in the organic EL device of the present invention is a novel compound, and these compounds can be synthesized, for example, as follows.
  • a 2-aminoarylazobenzene derivative is synthesized from a 1,2-diaminobenzene derivative and a nitroaryl derivative by a known method, and an oxidative cyclization reaction with bis (acetato-O) phenyliodine is performed.
  • a benzotriazole derivative having a group can be synthesized (see, for example, Non-Patent Document 4).
  • a bromo-substituted product of a benzotriazole derivative having an aryl group can be synthesized.
  • an arylamine compound represented by the general formula (1) of the present invention can be synthesized by performing a condensation reaction such as an Ullmann reaction or a Buchwald-Hartwig reaction between the bromo-substituted product and diarylamine. .
  • the brominated benzotriazole derivative can also be synthesized by brominating the synthesized benzotriazole derivative having an aryl group with N-bromosuccinimide or the like.
  • bromo-substituted products having different substitution positions can be obtained by changing the bromination reagent and conditions.
  • the arylamine compound represented by General formula (1) of this invention is compoundable by performing the same reaction.
  • Suzuki coupling of a boronic acid or a boronic acid ester derivative see, for example, Non-Patent Document 5 synthesized by reacting various aryl halides with pinacol borane or bis (pinacolato) diboron, for this bromo-substituted product.
  • the arylamine compound represented by the general formula (1) of the present invention can also be synthesized by performing a cross coupling reaction such as (see, for example, Non-Patent Document 6). Further, a boronic acid or a boronic acid ester (for example, see Non-Patent Document 5) derivative is synthesized from the bromo-substituted product, and a cross-coupling reaction such as Suzuki coupling with an aryl halide having various diarylamino groups (for example, The arylamine compound represented by the general formula (1) of the present invention can also be synthesized by performing Non-Patent Document 6).
  • a cross coupling reaction such as (see, for example, Non-Patent Document 6).
  • a boronic acid or a boronic acid ester for example, see Non-Patent Document 5
  • a cross-coupling reaction such as Suzuki coupling with an aryl halide having various diarylamino groups
  • a benzothiazole group, a benzothiazole group, a benzothiazole derivative, a benzoxazole derivative, or a bromo substituent of an indole derivative having a corresponding substituent, or a bromo substituent after bromination An arylamine compound represented by the general formula (1) of the present invention having a benzoxazole group or an indole group can be synthesized.
  • Tg glass transition point
  • refractive index is an index for improving the light extraction efficiency.
  • the glass transition point (Tg) was measured with a high sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
  • the refractive index was measured using a spectroscopic measurement device (F10-RT-UV, manufactured by Filmetrics) by preparing a thin film of 80 nm on a silicon substrate.
  • the organic EL device of the present invention for example, in the case of a light emitting device having a top emission structure, a metal anode, a hole transport layer, a light emitting layer, an electron transport layer, a translucent cathode, Containing a capping layer, having a hole injection layer between the anode and the hole transport layer, having an electron blocking layer between the hole transport layer and the light emitting layer, and between the light emitting layer and the electron transport layer And those having an electron injection layer between the electron transport layer and the cathode.
  • each layer of the organic EL element is preferably about 200 nm to 750 nm, and more preferably about 350 nm to 600 nm.
  • the film thickness of the capping layer is preferably 30 nm to 120 nm, for example, and more preferably 40 nm to 80 nm. In this case, good light extraction efficiency can be obtained. Note that the thickness of the capping layer can be changed as appropriate depending on the type of the light emitting material used for the light emitting element, the thickness of the organic EL element other than the capping layer, and the like.
  • an electrode material having a large work function such as ITO or gold is used.
  • an arylamine compound having a structure in which three or more triphenylamine structures are connected by a divalent group not containing a single bond or a hetero atom in the molecule for example, starburst Materials such as triphenylamine derivatives of various types, various triphenylamine tetramers, porphyrin compounds represented by copper phthalocyanine, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials are used. be able to.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • N, N′-diphenyl-N, N′-di (m-tolyl) benzidine hereinafter abbreviated as TPD
  • NPD N, N′-diphenyl- N, N'-di ( ⁇ -naphthyl) benzidine
  • TAPC 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane
  • N, N, N ′, N′-tetrabiphenylylbenzidine especially two triphenylamine structures in the molecule
  • an arylamine compound having a structure in which a single bond or a divalent group not containing a hetero atom is connected, for example, N, N, N ′, N′-tetrabiphenylylbenzidine.
  • arylamine compounds having a structure in which three or more triphenylamine structures in the molecule are linked by a divalent group not containing a single bond or a hetero atom such as various triphenylamine trimers and tetramers Is preferably used.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • the material usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the structure of a benzidine derivative such as TPD.
  • TPD a benzidine derivative
  • TCTA N-carbazolyl triphenylamine
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • Ad-Cz 2,2-bis (4-carbazol-9-ylphenyl) adamantane
  • Carbazole derivatives such as 9- [4- (carbazol-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene and triarylamine structures
  • a compound having an electron-blocking action such as a compound having an electron can be used.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • the light emitting layer of the organic EL device of the present invention metal complexes of quinolinol derivatives such as Alq 3 , various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, and the like are used. be able to.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used in addition to the light-emitting material.
  • quinacridone coumarin, rubrene, perylene, and derivatives thereof
  • benzopyran derivatives rhodamine derivatives, aminostyryl derivatives, and the like
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • a phosphorescent material can be used as the light emitting material.
  • a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
  • Green phosphorescent emitters such as Ir (ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6, red phosphorescent emitters such as Btp 2 Ir (acac), and the like are used as host materials.
  • carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (CBP), TCTA, and mCP can be used.
  • p-bis (triphenylsilyl) benzene (UGH2) and 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl-1H-benzimidazole) ) (TPBI) or the like, and a high-performance organic EL element can be manufactured.
  • the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
  • Non-Patent Document 7 a material that emits delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN as a light-emitting material.
  • CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • a phenanthroline derivative such as bathocuproine (BCP) or aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter abbreviated as BAlq).
  • BCP bathocuproine
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, pyridoindole derivatives, carbodiimides Derivatives, quinoxaline derivatives, phenanthroline derivatives, silole derivatives, and the like can be used.
  • quinolinol derivatives such as Alq 3 and BAlq
  • various metal complexes such as Alq 3 and BAlq
  • triazole derivatives triazine derivatives
  • oxadiazole derivatives oxadiazole derivatives
  • thiadiazole derivatives pyridoindole derivatives
  • carbodiimides Derivatives quinoxaline derivatives, phenanthroline derivatives, silole derivatives, and the like
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone,
  • an alkali metal salt such as lithium fluoride and cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal oxide such as aluminum oxide
  • a material usually used for the layer and further doped with a metal such as cesium can be used.
  • an electrode material having a low work function such as aluminum, an alloy having a lower work function such as a magnesium silver alloy, a magnesium calcium alloy, a magnesium indium alloy, an aluminum magnesium alloy, ITO, IZO or the like is used as an electrode material.
  • an arylamine compound represented by the general formula (1) may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • the organic EL element having the top emission structure has been described.
  • the present invention is not limited to this, and the organic EL element having the bottom emission structure or the dual emission structure that emits light from both the top and bottom directions is used.
  • organic EL elements In these cases, an electrode in a direction in which light is extracted from the light emitting element to the outside needs to be transparent or translucent.
  • the refractive index of the material constituting the capping layer is preferably larger than the refractive index of the adjacent electrode.
  • the refractive index of the material constituting the capping layer is preferably larger than the refractive index of the adjacent electrode, and the refractive index may be 1.70 or more, more preferably 1.80 or more, and 1.85. The above is particularly preferable.
  • the glass transition point was calculated
  • the compound of the present invention has a glass transition point of 100 ° C. or higher. This indicates that the thin film state is stable in the compound of the present invention.
  • a deposited film having a thickness of 80 nm was formed on a silicon substrate, and the refractive index at 633 nm was measured using a spectroscopic measurement apparatus (F10-RT-UV, manufactured by Filmetrics).
  • F10-RT-UV spectroscopic measurement apparatus
  • the comparative compounds (2-1), (2-2) and Alq 3 having the following structural formula were also measured (see, for example, Patent Document 3).
  • the compound of the present invention has a value higher than the refractive index of 1.70 to 1.81 of the comparative compounds (2-1), (2-2) and Alq 3 , The improvement of the extraction efficiency can be expected.
  • the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport on a glass substrate 1 on which a reflective ITO electrode is previously formed as a metal anode 2.
  • the layer 6, the electron injection layer 7, the cathode 8, and the capping layer 9 were deposited in this order.
  • the glass substrate 1 formed with ITO having a thickness of 150 nm was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250 ° C. for 10 minutes. Then, after performing UV ozone treatment for 2 minutes, this glass substrate with ITO was attached in a vacuum evaporation machine, and pressure was reduced to 0.001 Pa or less. Subsequently, a compound (HIM-1) having the following structural formula was formed to a thickness of 5 nm as a hole injection layer 3 so as to cover the metal anode 2. On the hole injection layer 3, the comparative compound (2-1) was formed as a hole transport layer 4 so as to have a film thickness of 70 nm.
  • compound EMD-1 NUBD370 manufactured by SFC Co., Ltd.
  • compound EMH-1 ABS113 manufactured by SFC Co., Ltd.
  • Binary vapor deposition was performed at a vapor deposition rate of 5:95, and a film thickness of 25 nm was formed.
  • lithium fluoride was formed as the electron injection layer 7 so as to have a film thickness of 0.5 nm.
  • a magnesium silver alloy was formed as a cathode 8 so as to have a film thickness of 14 nm.
  • Example 1 the compound (1-1) of Example 1 was formed as the capping layer 9 so as to have a film thickness of 60 nm.
  • the characteristic measurement was performed at normal temperature in air
  • Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the manufactured organic EL element.
  • Example 10 the organic layer was formed under the same conditions except that the compound (1-32) of Example 2 was formed to a film thickness of 60 nm instead of the compound (1-1) of Example 1 as the capping layer 9.
  • An EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 the organic layer was formed under the same conditions except that the compound (1-2) of Example 3 was formed to a film thickness of 60 nm instead of the compound (1-1) of Example 1 as the capping layer 9.
  • An EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 the organic layer was formed under the same conditions except that the compound (1-22) of Example 4 was formed to a thickness of 60 nm instead of the compound (1-1) of Example 1 as the capping layer 9.
  • An EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 1 For comparison, an organic EL device was manufactured under the same conditions as in Example 10 except that Alq 3 was formed to a thickness of 60 nm instead of the compound (1-1) of Example 1 as the capping layer 9. Produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • the driving voltage at a current density of 10 mA / cm 2 is the device of Comparative Example 1 (4.19 V) using Alq 3 and the devices of Examples 10 to 13 (4.17 to 4.18 V). ), The luminance, light emission efficiency, and power efficiency are almost the same as those of Comparative Example 1 using Alq 3 (light emission efficiency: 5.13 cd / A, power efficiency: 3.78 lm / W). In contrast, the devices of Examples 10 to 13 (light emission efficiency: 5.31 to 5.36 cd / A, power efficiency: 3.98 to 4.06 lm / W) were all improved.
  • the arylamine compound represented by the general formula (1) suitably used in the organic EL device of the present invention has a high refractive index, can greatly improve the light extraction efficiency, and the thin film state is stable. Therefore, it is excellent as a compound for an organic EL device.
  • the use of the compound having no absorption in each of the blue, green, and red wavelength regions is particularly suitable for displaying a clear and bright image with good color purity. For example, it has become possible to develop home appliances and lighting.

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  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un élément électroluminescent organique qui est pourvu d'une couche de revêtement qui possède un indice de réfraction élevé et d'excellentes caractéristiques en termes de stabilité et de durabilité de film mince, et qui est configurée en un matériau qui ne possède pas d'absorption dans des régions de longueur d'onde bleue, verte et rouge, afin d'améliorer des caractéristiques d'élément de l'élément électroluminescent organique, en particulier dans le but d'améliorer considérablement l'efficacité d'extraction de lumière. L'élément électroluminescent organique comprend séquentiellement au moins une électrode positive, une couche de transport de trous, une couche électroluminescente, une couche de transport d'électrons, une électrode négative et une couche de revêtement dans cet ordre, la couche de revêtement contenant un composé aryle amine représenté par la formule générale (1).
PCT/JP2014/003169 2013-07-03 2014-06-13 Élément électroluminescent organique WO2015001726A1 (fr)

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WO2021114801A1 (fr) * 2019-12-11 2021-06-17 广东阿格蕾雅光电材料有限公司 Composé arylamine à base d'imidazopyridine et son utilisation
CN112940013A (zh) * 2019-12-11 2021-06-11 广东阿格蕾雅光电材料有限公司 一种咪唑并吡啶的芳胺类化合物及其应用
US11878968B2 (en) 2021-07-09 2024-01-23 Plexium, Inc. Aryl compounds and pharmaceutical compositions that modulate IKZF2
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CN113937233A (zh) * 2021-09-30 2022-01-14 武汉天马微电子有限公司 一种有机电致发光器件及其应用

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JP2015092485A (ja) 2015-05-14
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