WO2018181370A1 - Composé ayant une structure d'azacarbazole, et dispositif électroluminescent organique - Google Patents

Composé ayant une structure d'azacarbazole, et dispositif électroluminescent organique Download PDF

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WO2018181370A1
WO2018181370A1 PCT/JP2018/012526 JP2018012526W WO2018181370A1 WO 2018181370 A1 WO2018181370 A1 WO 2018181370A1 JP 2018012526 W JP2018012526 W JP 2018012526W WO 2018181370 A1 WO2018181370 A1 WO 2018181370A1
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group
substituted
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carbon atoms
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安達　千波矢
卓也 上原
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保土谷化学工業株式会社
国立大学法人九州大学
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound suitable for an organic electroluminescence element which is a self-luminous element suitable for various display devices and the element, and more specifically, a compound having an azacarbazole structure, and an organic electroluminescence using the compound
  • the present invention relates to an element (hereinafter abbreviated as an organic EL element).
  • 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.
  • CBP 4,4′-di (N-carbazolyl) biphenyl
  • the excitation triplet level of the host compound is the excitation triplet level of the light emitter. It has become clear that it must be higher.
  • FIrpic which is a blue phosphorescent light emitting material represented by the following formula
  • the external quantum efficiency of the phosphorescent light emitting element remains at about 6%. This is thought to be because the triplet exciton level by FIrpic is insufficient because the excited triplet level of FIrpic is 2.67 eV, whereas the excited triplet level of CBP is as low as 2.57 eV. It was. This is demonstrated by the fact that the photoluminescence intensity of a thin film obtained by doping FIrpic into CBP shows temperature dependence (see Non-Patent Document 3).
  • mCBP 3,3′-di (9H-carbazol-9-yl) -1,1′-biphenyl
  • Tg glass transition point
  • the physical properties that the organic compound to be provided by the present invention should have include (1) high excitation triplet level, (2) bipolar transportability, and (3) stable thin film state. I can give you something.
  • the physical characteristics that the organic EL element to be provided by the present invention should have include (1) high luminous efficiency, (2) high luminance, and (3) low practical driving voltage. Can give.
  • the present inventors pay attention to the fact that the azacarbazole structure has a high excited triplet level and an electron transporting ability, and design a compound using the excited triplet level as an index.
  • a compound having a novel azacarbazole structure having characteristics suitable for phosphorescence and TADF light-emitting devices was found.
  • various organic EL devices were prototyped using the compound, and the characteristics of the devices were evaluated. As a result, the present invention was completed.
  • the following compound having an azacarbazole skeleton and an organic EL device are provided.
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1).
  • A, B, C, D, E, F, G, and H each represents at least one nitrogen atom and represents a carbon atom or a nitrogen atom
  • X, Y, and Z are the same or different from each other.
  • R 1 to R 10 are the same or different from each other. Hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group , A trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a linear chain having 1 to 6 carbon atoms which may have a substituent Or a branched alkyloxy group, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group , A substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsub
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-1).
  • A, B, C, D, E, F, G, and H each represents at least one nitrogen atom and represents a carbon atom or a nitrogen atom
  • X, Y, and Z are the same or different from each other.
  • R 1 to R 10 are the same or different from each other. Hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group , A trifluoromethyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a linear chain having 1 to 6 carbon atoms which may have a substituent Or a branched alkyloxy group, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group , A substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsub
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-2).
  • At least one of A, B, C and D represents a nitrogen atom and represents a carbon atom or a nitrogen atom
  • X, Y and Z may be the same or different from each other, and may be substituted or unsubstituted.
  • L represents a single bond, a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted group.
  • R 1 to R 10 may be the same or different from each other, Hydrogen atom, fluorine atom, chlorine atom, cyano group, trifluorome A til group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, and an optionally substituted cycloalkyl group having 5 to 10 carbon atoms A linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a linear or branched chain having 1 to 6 carbon atoms which may have a substituent An alkyloxy group, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, substituted or An unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-3).
  • At least one of A, B, C and D represents a nitrogen atom and represents a carbon atom or a nitrogen atom
  • X and Y may be the same or different from each other, and are substituted or unsubstituted aromatic.
  • L represents a disubstituted amino group substituted by a single bond, a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, or a substituted or unsubstituted aromatic group.
  • R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a deuterium atom. , Fluorine atom, chlorine atom, cyano group, trifluoromethyl Group, nitro group, optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, optionally substituted cycloalkyl group having 5 to 10 carbon atoms A linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a linear or branched group having 1 to 6 carbon atoms which may have a substituent.
  • Alkyloxy group optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
  • Single bond a substituted or unsubstituted methylene group, linked to each other through an oxygen atom or a sulfur atom may form a ring.
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-4).
  • At least one of A, B, C and D represents a nitrogen atom and represents a carbon atom or a nitrogen atom
  • X and Y may be the same or different from each other, and are substituted or unsubstituted aromatic.
  • L represents a disubstituted amino group substituted by a single bond, a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, or a substituted or unsubstituted aromatic group.
  • R 1 to R 10 may be the same or different from each other, and may be a hydrogen atom or a deuterium atom. , Fluorine atom, chlorine atom, cyano group, trifluoromethyl Group, nitro group, optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, optionally substituted cycloalkyl group having 5 to 10 carbon atoms A linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a linear or branched group having 1 to 6 carbon atoms which may have a substituent.
  • Alkyloxy group optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
  • Single bond a substituted or unsubstituted methylene group, linked to each other through an oxygen atom or a sulfur atom may form a ring.
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-5).
  • At least one of A, B, C and D represents a nitrogen atom and represents a carbon atom or a nitrogen atom
  • X and Y may be the same or different from each other, and are substituted or unsubstituted aromatic.
  • L represents a disubstituted amino group substituted by a single bond, a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, or a substituted or unsubstituted aromatic group.
  • R 1 to R 7 may be the same or different from each other, and may be a hydrogen atom or a deuterium atom. , Fluorine atom, chlorine atom, cyano group, trifluoromethyl , A nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, A linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent Oxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted A condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group
  • the present invention is a compound having an azacarbazole skeleton represented by the following general formula (1-6).
  • At least one of A, B, C and D represents a nitrogen atom and represents a carbon atom or a nitrogen atom
  • X and Y may be the same or different from each other, and are substituted or unsubstituted aromatic.
  • L represents a disubstituted amino group substituted by a single bond, a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, or a substituted or unsubstituted aromatic group.
  • R 1 to R 7 may be the same or different from each other, and may be a hydrogen atom or a deuterium atom. , Fluorine atom, chlorine atom, cyano group, trifluoromethyl , A nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, A linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent Oxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted A condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group
  • the organic layer is a light emitting layer, and the aza represented by the general formula (1)
  • General Formula (1) General Formula (1-1), X, Y, Z in General Formula (1-2) and General Formula (1-3), General Formula (1-4), General Formula (1- 5), “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by X and Y in general formula (1-6), or “substituted or unsubstituted
  • aromatic hydrocarbon group “aromatic heterocyclic group”
  • fused polycyclic aromatic group” in the substituted condensed polycyclic aromatic group specifically includes a phenyl group, a biphenylyl group, a terphenylyl group.
  • substituents are further substituted by the above-exemplified substituents. May be. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • these groups may have a substituent, and as the substituent, X, Y, Z in the general formula (1), general formula (1-1), general formula (1-2) and “Substituted aromatic hydrocarbon group” represented by X and Y in general formula (1-3), general formula (1-4), general formula (1-5), and general formula (1-6), “Substituted aromatic heterocyclic group” or “Substituted condensed polycyclic aromatic group” “Aromatic hydrocarbon group”, “Aromatic heterocyclic group” or “Condensed polycyclic aromatic group” may have “Substitution”
  • the thing similar to what was shown regarding "group” can be mention
  • the “condensed polycyclic aromatic divalent group” represents a divalent group formed by removing two hydrogen atoms from the above “aromatic hydrocarbon”, “aromatic heterocycle” or “fused polycyclic aromatic”.
  • these divalent groups may have a substituent, and examples of the substituent include general formula (1), general formula (1-1), general formula (1-2), and general formula (1-3 ), A general formula (1-4), a general formula (1-5), a “substituted aromatic hydrocarbon group”, a “substituted aromatic heterocyclic group” represented by L in the general formula (1-6) or
  • lifted and the aspect which can be taken can also mention the same thing.
  • the linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent "C1-C6 linear or branched alkyl group", “C5-C10 cycloalkyl group” or "C2-C6 linear or branched alkenyl group”
  • Specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, and n-butyl group.
  • Til isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, vinyl, allyl, iso Examples thereof include a propenyl group and a 2-butenyl group, and these groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituents in the “cycloalkyl group having 5 to 10 atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, Cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Groups; alkenyl groups such as vinyl groups and allyl groups; Aryloxy groups such as phenyloxy group and tolyloxy group; ary
  • R 1 to R 10 in formula (1), formula (1-1), formula (1-2), formula (1-3), formula (1-4), and formula (1- 5) “a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R 1 to R 7 in formula (1-6); “Linear or branched alkyloxy group having 1 to 6 carbon atoms” in “optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms” or “C5 to 10 carbon atoms” Specific examples of the cycloalkyloxy group include a methyloxy group, an ethyloxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, and an n-hexyloxy group.
  • cyclopentyloxy Ci group cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, etc.
  • these groups are single bonds, substituted or unsubstituted methylene groups And may be bonded to each other via an oxygen atom or a sulfur atom to form a ring.
  • R 1 to R 10 in formula (1) formula (1-1), formula (1-2), formula (1-3), formula (1-4), and formula (1- 5) “a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent” represented by R 1 to R 7 in formula (1-6) or “having a substituent
  • the “substituent” in the cycloalkyloxy group having 5 to 10 carbon atoms is a straight chain having 1 to 6 carbon atoms having a substituent represented by R 1 to R 10 in the general formula (1).
  • the “aromatic hydrocarbon group”, “aromatic heterocyclic group”, or “fused polycyclic aromatic group” in the “unsubstituted fused polycyclic aromatic group” includes the above general formula (1), general formula ( 1-1) X, Y, Z in formula (1-2) and formula (1-3), formula (1-4), formula (1-5), formula (1-6) "Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed polycyclic aromatic group” represented by X or Y And the same as those shown for the “aro
  • these groups may have a substituent, and as the substituent, X, Y, Z in the general formula (1), general formula (1-1), general formula (1-2) and “Substituted aromatic hydrocarbon group” represented by X and Y in general formula (1-3), general formula (1-4), general formula (1-5), and general formula (1-6), “Substituted aromatic heterocyclic group” or “Substituted condensed polycyclic aromatic group” “Aromatic hydrocarbon group”, “Aromatic heterocyclic group” or “Condensed polycyclic aromatic group” may have “Substitution”
  • the thing similar to what was shown regarding "group” can be mention
  • the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 1 to R 7 in the general formula (1-6) is specifically a phenyloxy group, biphenylyl Oxy, terphenylyloxy, naphthyloxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy, triphenylenyloxy, pyrenyloxy, perylenyloxy, etc.
  • These groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Further, these groups may have a substituent, and as the substituent, X, Y, Z in the general formula (1), general formula (1-1), general formula (1-2) and “Substituted aromatic hydrocarbon group” represented by X and Y in general formula (1-3), general formula (1-4), general formula (1-5), and general formula (1-6), “Substituted aromatic heterocyclic group” or “Substituted condensed polycyclic aromatic group” “Aromatic hydrocarbon group”, “Aromatic heterocyclic group” or “Condensed polycyclic aromatic group” may have “Substitution”
  • the thing similar to what was shown regarding "group” can be mention
  • R 1 to R 10 in formula (1), formula (1-1), formula (1-2), formula (1-3), formula (1-4), and formula (1- 5) A disubstituted substituent substituted with a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group represented by R 1 to R 7 in formula (1-6)
  • the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “amino group” includes X, Y in the general formula (1) and general formula (1-1).
  • substituents examples include X, Y and Z in the general formula (1) and general formula (1-1), and the general formula (1-2), “Substituted aromatic hydrocarbon group” represented by X and Y in general formula (1-3), general formula (1-4), general formula (1-5), and general formula (1-6), “Substituted aromatic heterocyclic group” or “Substituted condensed polycyclic aromatic group” “Aromatic hydrocarbon group”, “Aromatic heterocyclic group” or “Condensed polycyclic aromatic group” may have “Substitution” The thing similar to what was shown regarding "group” can be mention
  • X, Y and Z in the general formula (1) are preferably a diphenylamino group and a dimethylacridinyl group, more preferably a carbazolyl group and a diphenylacridinyl group, and particularly preferably a 3,9'-bicarbazolyl group.
  • a phenyl group is preferable, and a single bond is more preferable.
  • R 1 to R 10 in the general formula (1) are preferably a hydrogen atom or a deuterium atom, and more preferably a hydrogen atom from the viewpoint of synthesis.
  • the compound having an azacarbazole structure represented by the general formula (1) preferably used in the present invention has a higher excited triplet level than conventional materials, has an ability to confine excellent triplet excitons, and is a thin film The state is stable.
  • the compound having an azacarbazole structure represented by the general formula (1) preferably used in the present invention can be used as a constituent material of a light emitting layer of an organic EL device.
  • the compound represented by the general formula (1) which is superior in bipolar transportability as compared with conventional materials, the light emission efficiency is improved and the practical driving voltage is lowered.
  • the compound having an azacarbazole structure represented by the general formula (1) preferably used in the present invention is useful as a host compound of a light emitting layer of an organic EL device, and an organic EL device is produced using the compound.
  • an organic EL device is produced using the compound.
  • FIG. 1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 1).
  • FIG. 2 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 2).
  • FIG. 3 is a 1 H-NMR chart of the compound of Example 3 of the present invention (Compound 4).
  • FIG. 3 is a 1 H-NMR chart of the compound of Example 4 of the present invention (Compound 5).
  • FIG. 3 is a diagram showing organic EL element configurations of Examples 11 to 13 and Comparative Example 1.
  • the compound having an azacarbazole structure of the present invention can be synthesized, for example, as follows. First, ⁇ -carboline (5H-pyrido [4,3-b] indole) is synthesized from 1- (pyridin-4-yl) -1H-benzo [d] [1,2,3] triazole by Greve-Ullmann reaction. be able to. By reacting this ⁇ -carboline with 1,4-dibromobenzene, 5- (4-bromophenyl) -5H-pyrido [4,3-b] indole can be synthesized. A compound having an azacarbazole structure of the present invention can be synthesized by subjecting the carboline derivative having a bromo group to a condensation reaction such as a Backwald-Hartwig reaction or an Ullmann reaction.
  • a condensation reaction such as a Backwald-Hartwig reaction or an Ullmann reaction.
  • 5-phenyl-5H-pyrido [4,3-b] indole is synthesized by reacting ⁇ -carboline with iodobenzene, and then brominated with N-bromosuccinimide or the like to give 8- Bromo-5-phenyl-5H-pyrido [4,3-b] indole can be synthesized.
  • a compound having a carboline structure of the present invention can be synthesized by subjecting the carboline derivative having a bromo group to a condensation reaction such as a Backwald-Hartwig reaction or an Ullmann reaction.
  • bromo-substituted products with different substitution positions can be obtained by changing dibromobenzene with different substitution positions, reagents for bromination, and conditions.
  • Tg glass transition point
  • work function is an index of the energy level as the light emitting host material.
  • the glass transition point (Tg) was measured with a high sensitivity differential scanning calorimeter (DSC6200, manufactured by Seiko Instruments Inc.) using powder.
  • the work function was measured using an atmospheric photoelectron spectrometer (AC-3 type, manufactured by Riken Keiki Co., Ltd.) by forming a 100 nm thin film on the ITO substrate.
  • the excited triplet level of the compound of the present invention can be calculated from the measured phosphorescence spectrum.
  • the phosphorescence spectrum can be measured using a commercially available spectrophotometer.
  • a general method for measuring phosphorescence spectrum a method in which it is dissolved in a solvent and irradiated with excitation light at a low temperature (for example, see Non-Patent Document 4) or vapor deposited on a silicon substrate to form a thin film at a low temperature. There is a method of irradiating excitation light and measuring a phosphorescence spectrum.
  • the excited triplet level can be calculated by reading the wavelength of the first peak on the short wavelength side of the phosphorescence spectrum or the wavelength of the rising position on the short wavelength side and converting it to the light energy value according to the following equation.
  • the excited triplet level is an indicator of the confinement of triplet excitons in the phosphorescent emitter.
  • E is the value of light energy
  • h Planck's constant (6.63 ⁇ 10 ⁇ 34 Js)
  • c is the speed of light (3.00 ⁇ 10 8 m / s)
  • ⁇ is the short wavelength of the phosphorescence spectrum. This represents the wavelength (nm) of the rising edge.
  • 1 eV becomes 1.60 ⁇ 10 ⁇ 19 J.
  • an anode As the structure of the organic EL device of the present invention, on the substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, a cathode, And those having an electron injection layer between the electron transport layer and the cathode.
  • anode hole transport layer, light emitting layer, electron transport layer, electron injection layer, cathode
  • An anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode can also be used.
  • the light emitting layer, the hole transport layer, and the electron transport layer may have a structure in which two or more layers are laminated.
  • an electrode material having a large work function such as ITO or gold is used.
  • a hole injection layer of the organic EL device of the present invention in addition to a porphyrin compound typified by copper phthalocyanine, a naphthalene diamine derivative, a starburst type triphenylamine derivative, three or more triphenylamine structures in the molecule, Triphenylamine trimers and tetramers such as arylamine compounds having a structure linked by a divalent group containing no bond or hetero atom, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymers Materials can 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 referred to as “a”)
  • NPD N, N, N ′, N′-tetrabiphenylylbenzidine
  • Benzidine derivatives 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and tetramers, and carbazole derivatives 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.
  • a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly (styrene sulfonate) (hereinafter abbreviated as PSS) is used.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • These polymer materials can 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.
  • a material in which trisbromophenylamine hexachloroantimony is further P-doped to a material usually used for the layer, or a polymer having a TPD structure in its partial structure A compound or the like can be used.
  • TCTA 4,4 ′, 4 ′′ -tri (N-carbazolyl) triphenylamine
  • TCTA 9,9-bis [4- (carbazole- 9-yl) phenyl] fluorene
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • Ad 2,2-bis (4-carbazol-9-ylphenyl) adamantane
  • Carbazole derivatives such as 9- [4- (carbazol-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene
  • a compound having an electron blocking action such as a compound having a triarylamine structure 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.
  • various metal complexes such as metal complexes of quinolinol derivatives including tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ), anthracene derivatives, bisstyrylbenzene derivatives , Pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, and the like can be used.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • a compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) of the present invention as the host material, mCP , Thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used.
  • the dopant material quinacridone, coumarin, rubrene, anthracene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like 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.
  • a phosphorescent light emitting 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, and red phosphorescent emitters
  • Btp 2 Ir (acac) and Ir (piq) 3 are used.
  • a host material a compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) of the present invention, a hole injection / transport host material such as CBP, TCTA, mCP, etc. A carbazole derivative or the like can be used.
  • a hole injection / transport host material such as CBP, TCTA, mCP, etc.
  • a carbazole derivative or the like can be used.
  • an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like 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
  • 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.
  • 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.
  • an element having a structure in which a light-emitting layer manufactured using a compound having a different work function as a host material is stacked adjacent to a light-emitting layer manufactured using the compound of the present invention can be manufactured (for example, non-patented). Reference 5).
  • a phenanthroline derivative such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
  • BCP bathocuproine
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
  • 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.
  • various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, as well as metal complexes of quinolinol derivatives including Alq 3 and BAlq.
  • Derivatives, phenanthroline derivatives, silole derivatives, benzimidazole derivatives such as TPBI, and the like 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.
  • 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 or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
  • the glass transition point was calculated
  • Inventive Example 2 Compound 141 ° C.
  • Inventive Example 3 Compound 152 ° C.
  • Inventive Example 4 Compound 150 ° C.
  • the compound of the present invention has an energy level suitable as a material for the light emitting layer, which is comparable to that of mCBP generally used as a light emitting host.
  • Example 1 of the present invention a 10 ⁇ 5 mol / L toluene solution was prepared.
  • this toluene solution was irradiated with ultraviolet light at 300 K while passing nitrogen, fluorescence having a peak wavelength of 392 nm was observed.
  • Example 7 instead of the compound of Example 1 of the present invention (Compound 1), a 10 ⁇ 5 mol / L toluene solution of the compound of Example 2 of the present invention (Compound 2) was prepared, and the characteristics were evaluated in the same manner. Went. As a result, fluorescence having a peak wavelength of 373 nm was observed.
  • Example 7 instead of the compound of Example 1 of the present invention (Compound 1), a 10 ⁇ 5 mol / L toluene solution of the compound of Example 3 of the present invention (Compound 4) was prepared, and the characteristics were evaluated in the same manner. Went. As a result, fluorescence having a peak wavelength of 371 nm was observed.
  • Example 7 instead of the compound of Example 1 of the present invention (Compound 1), a 10 ⁇ 5 mol / L toluene solution of the compound of Example 4 of the present invention (Compound 5) was prepared, and the characteristics were evaluated in the same manner. Went. As a result, fluorescence having a peak wavelength of 369 nm was observed.
  • the organic EL element has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
  • the layer 5, the light emitting layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 100 nm was formed was washed with an organic solvent, and then the surface was washed by UV ozone treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
  • NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • TCTA was formed as a first hole transport layer 4 so as to have a film thickness of 20 nm at a deposition rate of 2.0 ⁇ / sec.
  • the second hole transport layer 5 was formed such that the compound of Example 2 of the present invention (Compound 2) had a film thickness of 15 nm at a deposition rate of 2.0 ⁇ / sec. .
  • the compound of Example 2 of the present invention (Compound 2) and the light emitting material 2- [4- [3- (N-phenyl-9H-carbazole) shown below are used.
  • -3-yl) -9H-carbazol-9-yl] phenyl] -4,6-diphenyl-1,3,5-triazine (compound 112), the deposition rate ratio of which is compound of compound of Example 2 of the present invention (compound 2) ):
  • Luminescent material (compound 112) binary deposition was performed at a deposition rate of 85:15 to form a film thickness of 20 nm.
  • TPBi was formed as an electron transport layer 8 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • lithium fluoride was formed as the electron injection layer 9 so as to have a film thickness of 0.7 nm at a deposition rate of 0.1 ⁇ / sec.
  • aluminum was deposited to a thickness of 100 nm to form the cathode 10.
  • the characteristic measurement was performed at normal temperature in air
  • the organic EL element has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
  • the layer 5, the light emitting layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 100 nm was formed was washed with an organic solvent, and then the surface was washed by UV ozone treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
  • NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • TCTA was formed as a first hole transport layer 4 so as to have a film thickness of 20 nm at a deposition rate of 2.0 ⁇ / sec.
  • the compound (compound 4) of Example 3 of the present invention was formed as a second hole transport layer 5 so as to have a film thickness of 15 nm at a deposition rate of 2.0 ⁇ / sec. .
  • the compound of Example 3 of the present invention (Compound 4) and the light emitting material (Compound 112) are deposited. 4):
  • the light-emitting material (compound 112) was subjected to binary vapor deposition at a vapor deposition rate of 85:15 to form a film thickness of 20 nm.
  • TPBi was formed as an electron transport layer 8 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • lithium fluoride was formed as the electron injection layer 9 so as to have a film thickness of 0.7 nm at a deposition rate of 0.1 ⁇ / sec.
  • aluminum was deposited to a thickness of 100 nm to form the cathode 10.
  • the characteristic measurement was performed at normal temperature in air
  • the organic EL element has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
  • the layer 5, the light emitting layer 6, the hole blocking layer 7, the electron transport layer 8, the electron injection layer 9, and the cathode (aluminum electrode) 10 were deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 100 nm was formed was washed with an organic solvent, and then the surface was washed by UV ozone treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
  • NPD was formed as a hole injection layer 3 so as to cover the transparent anode 2 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • TCTA was formed as a first hole transport layer 4 so as to have a film thickness of 20 nm at a deposition rate of 2.0 ⁇ / sec.
  • the compound (Compound 5) of Example 4 of the present invention was formed as a second hole transport layer 5 so as to have a film thickness of 15 nm at a deposition rate of 2.0 ⁇ / sec. .
  • the compound (compound 5) of Example 4 of the present invention and the light emitting material (Compound 112) are deposited. 5):
  • the light emitting material (compound 112) was subjected to binary vapor deposition at a vapor deposition rate of 85:15 to form a film thickness of 20 nm.
  • TPBi was formed as an electron transport layer 8 so as to have a film thickness of 30 nm at a deposition rate of 2.0 ⁇ / sec.
  • lithium fluoride was formed as the electron injection layer 9 so as to have a film thickness of 0.7 nm at a deposition rate of 0.1 ⁇ / sec.
  • aluminum was deposited to a thickness of 100 nm to form the cathode 10.
  • the characteristic measurement was performed at normal temperature in air
  • Luminescence when DC voltage is applied to the organic EL device produced using the compound of Example 2 (Compound 2), the compound of Example 3 (Compound 4), and the compound of Example 4 (Compound 5) of the present invention Table 1 summarizes the measurement results of the characteristics.
  • Example 11 As shown in Table 1, the voltage when a current density of 10 mA / cm 2 was passed was 7.8 V in Example 11 and 7.8 V in Example 11 compared to 7.8 V in Comparative Example 1 using mCBP. In 6.8V and Example 13, the value which was substantially equal to 7.0V or fell was shown.
  • Example 11 For the luminance, substantially equal with respect to 1116cd / m 2 of Comparative Example 1 using mCBP, Example 11, 1107cd / m 2, Example 12, 1550cd / m 2, and 1237cd / m 2 in Example 13, Or it showed a greatly improved value.
  • the organic EL device using the compound of the present invention can achieve a significant decrease in driving voltage and a significant improvement in light emission efficiency as compared with a device using mCBP.
  • the compound having azacarbazole of the present invention has good thin film stability and is excellent as a material for the light emitting layer, particularly as a host material for the light emitting layer. Moreover, the brightness

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Le problème décrit par la présente invention porte sur la fourniture d'un composé hôte destiné à une couche électroluminescente, le composé étant un matériau hautement efficace pour un dispositif électroluminescent organique, présente un niveau de triplet excité élevé, et est capable de confiner complètement des excitons triplets d'émetteurs phosphorescents et de fluorescence retardée thermiquement activée (TADF), et possède une excellente stabilité de film mince, c'est-à-dire, présente un point de transition vitreuse (Tg) élevé ; ainsi qu'un dispositif électroluminescent organique hautement efficace et hautement luminescent utilisant le composé. La solution selon la présente invention porte sur un dispositif électroluminescent organique qui a une paire d'électrodes et au moins une couche organique prise en sandwich entre ces derniers, le dispositif électroluminescent organique étant caractérisé en ce que la couche organique est une couche électroluminescente. L'invention concerne également un composé ayant une structure d'azacarbazole représenté par la formule générale (1) qui est utilisé en tant que matériau constituant la couche électroluminescente.
PCT/JP2018/012526 2017-03-28 2018-03-27 Composé ayant une structure d'azacarbazole, et dispositif électroluminescent organique WO2018181370A1 (fr)

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WO2004095891A1 (fr) * 2003-04-23 2004-11-04 Konica Minolta Holdings, Inc. Materiau pour dispositif electroluminescent organique, dispositif electroluminescent organique, dispositif d'eclairage et affichage
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WO2011016202A1 (fr) * 2009-08-05 2011-02-10 保土谷化学工業株式会社 Composé ayant une structure de cycle anthracène substitué et une structure de cycle pyridoindole et dispositif électroluminescent organique
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WO2015175678A1 (fr) * 2014-05-14 2015-11-19 President And Fellows Of Harvard College Matériaux pour diodes électroluminescentes organiques
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