WO2023054110A1 - Élément luminescent - Google Patents

Élément luminescent Download PDF

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Publication number
WO2023054110A1
WO2023054110A1 PCT/JP2022/035146 JP2022035146W WO2023054110A1 WO 2023054110 A1 WO2023054110 A1 WO 2023054110A1 JP 2022035146 W JP2022035146 W JP 2022035146W WO 2023054110 A1 WO2023054110 A1 WO 2023054110A1
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WIPO (PCT)
Prior art keywords
group
ring
bonded
compound
layer
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PCT/JP2022/035146
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English (en)
Japanese (ja)
Inventor
慎一 稲員
敏明 佐々田
浩平 浅田
太一 安倍
孝幸 飯島
孝和 斎藤
謙 吉岡
Original Assignee
住友化学株式会社
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Publication of WO2023054110A1 publication Critical patent/WO2023054110A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the ring L 1 is a pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, diazole ring or triazole ring, and these rings may have a substituent, and the ring
  • L2 is a benzene ring, a pyridine ring, or a diazabenzene ring, and these rings may have a substituent.
  • Ar H1 and Ar H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • n H1 represents an integer of 0 or more.
  • L H1 represents a divalent group, and the divalent group may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • a X1 and a X2 each independently represent an integer of 0 or more.
  • Ar 1 X1 and Ar 2 X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded; and these groups may have a substituent.
  • At least one of the plurality of X'' is a cross-linking group.
  • the cross-linking group is at least one cross-linking group selected from Group A of cross-linking groups. (Crosslinking group A group)
  • the "alkyl group” may be either linear or branched.
  • the number of carbon atoms in the linear alkyl group is generally 1-50, preferably 1-20, more preferably 1-10, not including the number of carbon atoms in the substituents.
  • the number of carbon atoms in the branched alkyl group is usually 3-50, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
  • the alkyl group may have a substituent.
  • a polycyclic heterocyclic compound is preferably a group consisting of a boron atom, an oxygen atom, a sulfur atom and a nitrogen atom, since the light-emitting device of the present disclosure has superior luminance lifetime.
  • a polycyclic heterocyclic compound containing in the ring at least one selected from and more preferably a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom in the ring More preferred are polycyclic heterocyclic compounds containing a boron atom and a nitrogen atom that does not form a double bond in the ring.
  • ⁇ EST of the low-molecular-weight compound (B) may be 2.0 eV or less, 1.5 eV or less, 1.0 eV or less, or 0.80 eV or less. However, it is preferably 0.60 eV or less, more preferably 0.55 eV or less, and even more preferably 0.50 eV or less, because the luminance lifetime of the light-emitting element of the present disclosure is superior.
  • ⁇ EST of the low-molecular-weight compound (B) may be 0.001 eV or more, 0.01 eV or more, 0.10 eV or more, or 0.20 eV or more. may be 0.30 eV or more, or 0.40 eV or more.
  • Y 1 is preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group, more preferably an oxygen atom, It is a sulfur atom or a group represented by -N(Ry)-, more preferably a group represented by -N(Ry)-, and these groups may have a substituent.
  • Ar BP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
  • L BP1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an alkylene group or an arylene group, still more preferably an arylene group, these groups may have a substituent.
  • Examples and preferred ranges of the arylene group and divalent heterocyclic group in LBP1 are the same as those of the arylene group and divalent heterocyclic group in Ar Y1 described below.
  • the alkylene group in LBP1 is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
  • Examples and preferred ranges of R BP1 are the same as examples and preferred ranges of R X1 to R X3 described later.
  • the structural unit represented by the formula (X) below is preferable to further include a structural unit represented by formula (Y) described below.
  • the number of carbon atoms in the aromatic heterocyclic ring in ring L 1 is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 10, not including the number of carbon atoms in substituents. , particularly preferably 1 to 5, particularly preferably 1 to 3.
  • the number of heteroatoms in the aromatic heterocyclic ring in ring L 1 is preferably 1 to 30, more preferably 1 to 10, still more preferably 1 to 5, not including the number of heteroatoms in the substituents. , particularly preferably 1 to 3.
  • Examples of the ring L 1 include aromatic heterocycles containing one or more nitrogen atoms in the ring among the aromatic heterocycles exemplified in the section of the heterocyclic group described above, and the aromatic heterocycle may have a substituent.
  • MAP1 represents a group obtained by removing one hydrogen atom from the metal complex represented by formula (1).
  • MAP2 represents a group obtained by removing two hydrogen atoms from the metal complex represented by formula (1).
  • MAP3 represents a group obtained by removing three hydrogen atoms from the metal complex represented by formula (1).
  • L AP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R AP1 )-, an oxygen atom or a sulfur atom, and these groups are It may have a substituent.
  • the structural unit represented by the formula (X) below is superior, the structural unit represented by the formula (X) below and It is preferable to further include a structural unit represented by formula (Y) described below.
  • the first compound, the compound (A1), and the compound (B1) electrically interact to efficiently convert the first compound to the compound (A1).
  • the compound (B1) can be made to emit light more efficiently, and the luminance of the light-emitting element of the present disclosure Better life.
  • the first compound preferably exhibits solubility in a solvent capable of dissolving the compound (B1) and the compound (A1), since the light-emitting device of the present disclosure can be produced by a wet method. .
  • the polymer compound (A) may have at least one function selected from a host material, an assist dopant material, and a dopant material. It may have at least two functions of the assist dopant material and the dopant material, or may have three functions of the host material, the assist dopant material and the dopant material.
  • the compound (B1) is preferably a host material, an assist dopant material, or a dopant material, since the light-emitting device of the present disclosure has a superior luminance lifetime.
  • the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. good too.
  • Examples and preferred ranges of the aryl group, which is a substituent of the amino group are the same as the examples and preferred ranges of the aryl group in Ar H1 and Ar H2 .
  • Examples and preferred ranges of the monovalent heterocyclic group which is a substituent of the amino group are the same as the examples and preferred range of the monovalent heterocyclic group in Ar 1 H1 and Ar 2 H2 .
  • Preferred substituents that Ar H1 and Ar H2 may have are a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, and a monovalent A heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group , a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, even if these groups further have a substituent good.
  • a divalent heterocyclic group is preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, or pyridine because the light-emitting device of the present disclosure has superior luminance lifetime.
  • the first polymer compound is a polymer compound containing at least one structural unit selected from the group consisting of structural units represented by formula (X) and structural units represented by formula (Y).
  • the first polymer compound is preferably a polymer compound different from the polymer compound (A), the polymer compound (B), and the polymer compound containing a structural unit having a cross-linking group.
  • the structural unit (B) and a structural unit having a cross-linking group are more preferably polymer compounds.
  • the arylene group represented by the structural unit Ar Y1 represented by the formula (Y) is preferably a monocyclic or bicyclic to hexacyclic aromatic group because the light-emitting element of the present disclosure has a superior luminance lifetime.
  • Examples of structural units represented by formula (Y) include structural units comprising at least one arylene group represented by formulas (Y-101)-(Y-141), and formulas (Y-201)-( Y-209) consisting of at least one divalent heterocyclic group, at least one arylene group represented by formulas (Y-301) to (Y-306) and at least one Structural units composed of a divalent group directly bonded to a divalent heterocyclic group are exemplified.
  • Examples of structural units represented by formula (X) include structural units represented by the following formula.
  • the first polymer compound can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), Suzuki reaction, Yamamoto , Buchwald reaction, Stille reaction, Negishi reaction, Kumada reaction, and other coupling reactions using a transition metal catalyst.
  • the method of charging the monomers includes a method of charging the entire amount of the monomers into the reaction system at once, a method of charging a part of the monomers and reacting them, and then charging the remaining monomers all at once. Examples thereof include a method of continuously or dividedly charging, a method of continuously or dividingly charging a monomer, and the like.
  • the antioxidant may be any compound that is soluble in the same solvent as the compound (B1) and compound (A1) and does not inhibit light emission and charge transport. mentioned.
  • the content of the antioxidant is usually 0.00001 when the total content of the compound (B1) and the compound (A1) is 100 parts by mass. ⁇ 10 parts by mass.
  • Antioxidants may be used singly or in combination of two or more.
  • the content of the compound of the second layer in the layer (2) is, for example, 0.01 to 0.01 when the total content of the compound of the second layer and the material of the second layer is 100 parts by mass. It is 99 parts by mass, and since the light-emitting device of the present disclosure has a superior luminance lifetime, it is preferably 0.1 to 90 parts by mass, more preferably 0.5 to 70 parts by mass, and even more preferably 1 to 50 parts by mass. 3 to 30 parts by mass, particularly preferably 5 to 20 parts by mass.
  • the polymer compound of the second layer has excellent hole-transporting property of the polymer compound of the second layer, and the luminance life of the light-emitting device of the present disclosure is superior, so the structure represented by formula (X) It preferably contains a unit and a structural unit represented by formula (Y).
  • the formula (X) contained in the polymer compound of the second layer may be within a range in which the function of the polymer compound of the second layer can be exhibited.
  • the formula (X) contained in the polymer compound of the second layer contains a structural unit represented by the formula (X) and a structural unit represented by the formula (Y), the formula (X) contained in the polymer compound of the second layer.
  • the total content of the structural units represented by the formula (Y) and the structural units represented by the formula (Y) is, for example, 0.1 with respect to the total content of the structural units contained in the polymer compound of the second layer. It is preferably 1 to 100 mol %, more preferably 1 to 100 mol %, because the hole transport property of the polymer compound of the second layer is excellent and the luminance life of the light emitting device of the present disclosure is more excellent. is 10 to 100 mol%, more preferably 30 to 100 mol%, still more preferably 50 to 100 mol%, particularly preferably 70 to 100 mol%, particularly preferably 90 to 100 mol% is.
  • the second layer is a layer containing a crosslinked compound of a compound having a crosslinkable group, and the compound having a crosslinkable group contains a structural unit having a crosslinkable group. It is preferably a molecular compound.
  • Structural unit mA represented by formula (Z′) is usually an integer of 0 to 10, and is preferably an integer of 0 to 7, more preferably an integer of 0 to 7, because the light-emitting device of the present disclosure has a superior luminance life. It is an integer of 0 to 4, more preferably an integer of 0 to 2, particularly preferably 0 or 1, particularly preferably 0.
  • m is usually an integer of 0 to 10, preferably an integer of 0 to 7, more preferably an integer of 0 to 4, and still more preferably 0, because the light-emitting device of the present disclosure has a superior luminance lifetime. It is an integer of ⁇ 2, and particularly preferably 0.
  • the content of the structural unit represented by the formula (X) is such that the polymer compound having the cross-linking group functions. It is acceptable if it is within the range of When the polymer compound having a cross-linking group contains the structural unit represented by formula (X), the content of the structural unit represented by formula (X) is the amount of the structural unit contained in the polymer compound having a cross-linking group. With respect to the total content, for example, 0.1 to 99.9 mol%, the hole transport property of the polymer compound having a cross-linking group is excellent, and the luminance life of the light emitting device of the present disclosure is more excellent.
  • low-molecular-weight compounds having a cross-linking group examples include the compounds shown below.
  • the first emissive layer is typically the first layer.
  • the hole-injecting layer is the second layer or layer containing a hole-injecting material, preferably a layer containing a hole-injecting material.
  • the hole-injecting material contained in the hole-injecting layer includes, for example, the holes that the first composition may contain. Infusion materials are included.
  • the hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.
  • the light-emitting device of the present disclosure can be manufactured, for example, by sequentially laminating each layer on a substrate. Specifically, an anode is provided on a substrate, layers such as a hole injection layer and a hole transport layer are provided thereon, a light emitting layer is provided thereon, and an electron transport layer, an electron injection layer and the like are provided thereon.
  • a light-emitting device can be manufactured by providing a layer and further laminating a cathode thereon.
  • a cathode is provided on a substrate, layers such as an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, and a hole injection layer are provided thereon, and an anode is further provided thereon.
  • the light-emitting element of the present disclosure is suitable as a light source for backlight of a liquid crystal display device, a light source for illumination, organic EL lighting, a display device such as a computer, a television, and a mobile terminal (e.g., an organic EL display and an organic EL television). can be used.
  • a metal complex MC3 was synthesized by the following method.
  • the filter top was washed with a mixed solvent of chloroform and tetrahydrofuran (volume ratio: 1).
  • the obtained filtrate was concentrated under reduced pressure, recrystallized three times using a mixed solvent of heptane and 2-propanol (volume ratio 8:1), and dried under reduced pressure at 50°C to obtain compound MC3F (12.2 g, white solid) was obtained in 90% yield.
  • the HPLC area percentage value of compound MC3F was greater than 99.5%.
  • a light-emitting device CD2 was fabricated in the same manner as in Example D3, except that “polymer compound HTL-1” was used. EL light emission was observed by applying a voltage to the light emitting element CD2. LT70 of the light emitting element CD2 was measured. Also, the CIE chromaticity coordinates of the light-emitting element CD2 at 50 mA/cm 2 were measured.
  • a light-emitting device D10 was produced in the same manner as above. EL emission was observed by applying a voltage to the light emitting element D10. LT70 of the light-emitting element D10 was measured. Also, the CIE chromaticity coordinates of the light-emitting element D10 at 50 mA/cm 2 were measured.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention fournit un élément luminescent d'une excellente durée de vie de luminance.　Plus précisément, l'invention concerne un élément luminescent qui possède une anode, une cathode, et une première ainsi qu'une seconde couche agencées entre l'anode et la cathode. La première couche comprend un composé (A1) et un composé (B1), et ladite seconde couche comprend au moins un composé choisi dans un groupe constitué d'un composé (A2) et d'un composé (B2). Le composé (A1) et le composé (A2) consistent en au moins un élément choisi dans un groupe constitué : d'un complexe métallique représenté par la formule (1) ; et d'un composé à haut poids moléculaire (A) qui contient une unité structurale possédant un groupe dans lequel au moins un atome d'hydrogène est retiré du complexe métallique représenté par la formule (1). Le composé (B1) et le composé (B2) consistent en au moins un élément choisi dans un groupe constitué : d'un composé à faible poids moléculaire (B) possédant un squelette hétérocyclique condensé (b) ; et d'un composé à haut poids moléculaire qui contient une unité structurale possédant un groupe dans lequel au moins un atome d'hydrogène est retiré du composé à faible poids moléculaire (B).
PCT/JP2022/035146 2021-09-29 2022-09-21 Élément luminescent WO2023054110A1 (fr)

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JP2021160161 2021-09-29

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015092840A1 (fr) * 2013-12-16 2015-06-25 株式会社日立製作所 Élément électroluminescent organique
WO2019004248A1 (fr) * 2017-06-30 2019-01-03 住友化学株式会社 Composé macromoléculaire, et élément luminescent mettant en œuvre celui-ci
WO2019004247A1 (fr) * 2017-06-30 2019-01-03 住友化学株式会社 Élément luminescent, et composé polymère avantageux pour la fabrication de celui-ci
US20200308209A1 (en) * 2019-03-28 2020-10-01 Samsung Display Co., Ltd. Organic light-emitting device and electronic apparatus
WO2020203209A1 (fr) * 2019-03-29 2020-10-08 住友化学株式会社 Élément électroluminescent et composition pour élément électroluminescent
US20210098721A1 (en) * 2019-10-01 2021-04-01 Samsung Display Co., Ltd. Organic electroluminescence device
JP2021057593A (ja) * 2019-10-01 2021-04-08 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子
US20210130382A1 (en) * 2019-10-30 2021-05-06 Lg Display Co., Ltd. Organometallic compound, organic light emitting diode and organic light emitting device including the same
CN113444207A (zh) * 2021-06-22 2021-09-28 南京邮电大学 一种本征可拉伸发光弹性体及其制备方法与应用
US20220190276A1 (en) * 2020-12-15 2022-06-16 Samsung Display Co., Ltd. Light-emitting device and an electronic apparatus including same
US20220293863A1 (en) * 2021-03-03 2022-09-15 Samsung Display Co., Ltd. Light-emitting device and electronic apparatus including the same

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015092840A1 (fr) * 2013-12-16 2015-06-25 株式会社日立製作所 Élément électroluminescent organique
WO2019004248A1 (fr) * 2017-06-30 2019-01-03 住友化学株式会社 Composé macromoléculaire, et élément luminescent mettant en œuvre celui-ci
WO2019004247A1 (fr) * 2017-06-30 2019-01-03 住友化学株式会社 Élément luminescent, et composé polymère avantageux pour la fabrication de celui-ci
US20200308209A1 (en) * 2019-03-28 2020-10-01 Samsung Display Co., Ltd. Organic light-emitting device and electronic apparatus
WO2020203209A1 (fr) * 2019-03-29 2020-10-08 住友化学株式会社 Élément électroluminescent et composition pour élément électroluminescent
US20210098721A1 (en) * 2019-10-01 2021-04-01 Samsung Display Co., Ltd. Organic electroluminescence device
JP2021057593A (ja) * 2019-10-01 2021-04-08 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子
US20210130382A1 (en) * 2019-10-30 2021-05-06 Lg Display Co., Ltd. Organometallic compound, organic light emitting diode and organic light emitting device including the same
US20220190276A1 (en) * 2020-12-15 2022-06-16 Samsung Display Co., Ltd. Light-emitting device and an electronic apparatus including same
US20220293863A1 (en) * 2021-03-03 2022-09-15 Samsung Display Co., Ltd. Light-emitting device and electronic apparatus including the same
CN113444207A (zh) * 2021-06-22 2021-09-28 南京邮电大学 一种本征可拉伸发光弹性体及其制备方法与应用

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