WO2017191896A1 - Composé électroluminescent organique et dispositif électroluminescent organique le comportant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique le comportant Download PDF

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WO2017191896A1
WO2017191896A1 PCT/KR2017/002959 KR2017002959W WO2017191896A1 WO 2017191896 A1 WO2017191896 A1 WO 2017191896A1 KR 2017002959 W KR2017002959 W KR 2017002959W WO 2017191896 A1 WO2017191896 A1 WO 2017191896A1
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substituted
unsubstituted
organic electroluminescent
alkyl
aryl
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PCT/KR2017/002959
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English (en)
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Hong-Se OH
Young-Kwang Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020170024353A external-priority patent/KR20170124957A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US16/093,695 priority Critical patent/US10797243B2/en
Priority to JP2018554333A priority patent/JP6846438B2/ja
Priority to CN201780024400.8A priority patent/CN109071413B/zh
Priority to EP17792799.3A priority patent/EP3452442B1/fr
Publication of WO2017191896A1 publication Critical patent/WO2017191896A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • 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
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • 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
    • H10K85/30—Coordination compounds
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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 disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device In order to enhance the efficiency and stability of an organic EL device, it has a structure of a multilayer comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • the selection of a compound comprised in the hole transport layer is known as a method for improving the characteristics of a device such as hole transport efficiency to the light-emitting layer, luminous efficiency, lifespan, etc.
  • CuPc copper phthalocyanine
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
  • MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
  • Korean Patent Appln. Laying-Open No. KR 10-2015-0066202 discloses a benzo[b]fluorene substituted with an arylamino, etc. However, the reference does not specifically disclose a compound in which an arylamino, etc., is substituted at the fifth carbon position of a benzo[b]fluorene.
  • the objective of the present disclosure is to provide an organic electroluminescent compound which can be used to produce an organic electroluminescent device having excellent lifespan properties, improved luminous efficiency due to an increase of triplet energy, and/or excellent thermal stability due to a decrease of deposition temperature.
  • the present inventors found that luminous efficiency is improved due to an increase of triplet energy and/or thermal stability is improved due to a decrease of deposition temperature by having a substituent at the fifth carbon position of an organic electroluminescent compound having a structure of benzo[b]fluorene. More specifically, the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
  • Ar 1 to Ar 6 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or a substituted or unsubstituted spiro[fluorene-(C3-C30)cycloalkane]yl; or Ar 1 and Ar 2 , Ar 3 and Ar 4 , and Ar 5 and Ar 6 may be linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
  • L 2 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, with a proviso that where n is 0, L 2 does not exist;
  • R 1 and R 2 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon
  • R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • n represents an integer of 1 to 2, where m is 2, each of NAr 1 Ar 2 may be the same or different;
  • n an integer of 0 to 2, where n is 2, each of NAr 3 Ar 4 may be the same or different;
  • a represents an integer of 1 to 5, where a is an integer of 2 or more, each of R 1 may be the same or different;
  • b represents an integer of 1 to 4, where b is an integer of 2 or more, each of R 2 may be the same or different;
  • the heteroaryl(ene) contains at least one hetero atom selected from B, N, O, S, Si, and P;
  • the heterocycloalkyl contains at least one hetero atom selected from O, S, and N.
  • an organic electroluminescent device having excellent luminous efficiency and/or thermal stability can be produced.
  • the luminous efficiency and/or thermal stability of the organic electroluminescent device is excellent, a relatively long lifespan of the device can be achieved.
  • the present disclosure relates to an organic electroluminescent compound of formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
  • the organic electroluminescent material of the present disclosure may comprise at least one compound represented by formula 1.
  • the compound represented by formula 1 may be comprised in at least one layer constituting an organic electroluminescent device, and may be comprised in a light-emitting layer as a phosphorescent host material and/or a hole transport layer as a hole transport material, but is not limited thereto.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • “5- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 5 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 20, more preferably 5 to 15; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetra
  • the compound of formula 1 may be represented by the following formula 2 or 3:
  • Ar 1 to Ar 6 , L 1 , L 2 , R 1 , R 2 , a, b, m, and n are as defined in formula 1.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • Ar 1 to Ar 6 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or a substituted or unsubstituted spiro[fluorene-(C3-C30)cycloalkane]yl; or Ar 1 and Ar 2 , Ar 3 and Ar 4 , and Ar 5 and Ar 6 may be linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted 5- to 15-membered heteroaryl, or a substituted or unsubstituted spiro[fluorene-(C5-C8)cycloalkane]yl, and more preferably, Ar 1 to Ar 4 each independently represent a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C20)aryl; a 5- to 15-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C12)aryl; an unsubstituted spiro[fluorene-cyclopentane]yl; or an unsubstituted spiro[fluorene-cyclohexane]yl.
  • Ar 1 to Ar 4 may each independently represent a phenyl, a biphenyl, a terphenyl, a fluorenyl substituted with a methyl(s), a fluorenyl substituted with a phenyl(s), a benzofluorenyl substituted with a methyl(s), a naphthylphenyl, a phenyl substituted with a fluorene, a pyridinyl substituted with a phenyl, a dibenzofuranyl, a dibenzothiophenyl, a dibenzosilolyl substituted with a methyl(s), a dibenzosilolyl substituted with a phenyl(s), a spiro[fluorene-cyclopentane]yl, a spiro[fluorene-cyclohexane]yl, etc.
  • Ar 5 and Ar 6 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a mono- or polycyclic, 5- to 15-membered alicyclic or aromatic ring, and more preferably, Ar 5 and Ar 6 each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl; or may be linked to each other to form a monocyclic, 5- to 15-membered alicyclic ring.
  • Ar 5 and Ar 6 may each independently represent a methyl, a phenyl, etc., or may be linked to each other to form a spirocyclopentane.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, preferably represents a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 15-membered heteroarylene, and more preferably represents a single bond, an unsubstituted (C6-C20)arylene, or an unsubstituted 5- to 15-membered heteroarylene.
  • L 1 may represent a single bond, a phenylene, a naphthylene, a biphenylene, a naphthylphenylene, a pyridinephenylene, a pyridinylene, a phenylpyridinylene, a bipyridinylene, a dibenzofuranylene, a dibenzothiophenylene, etc.
  • L 2 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, with a proviso that where n is 0, L 2 does not exist.
  • L 2 preferably represents a single bond, or a substituted or unsubstituted (C6-C12)arylene, and more preferably represents a single bond, or an unsubstituted (C6-C12)arylene.
  • L 2 may represent a single bond, a phenylene, etc.
  • R 1 and R 2 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon
  • R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted 5- to 15-membered heteroaryl, or a substituted or unsubstituted spiro[fluorene-(C5-C8)cycloalkane]yl;
  • Ar 5 and Ar 6 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a mono- or polycyclic, 5- to 15-membered alicyclic or aromatic ring;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 15-membered heteroarylene;
  • L 2 represents a single bond, or a substituted or unsub
  • Ar 1 to Ar 4 each independently represent a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C20)aryl; a 5- to 15-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C12)aryl; an unsubstituted spiro[fluorene-cyclopentane]yl; or an unsubstituted spiro[fluorene-cyclohexane]yl; Ar 5 and Ar 6 each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl; or may be linked to each other to form a monocyclic, 5- to 15-membered alicyclic ring; L 1 represents a single bond, an unsubstituted (
  • the organic electroluminescent compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to a person skilled in the art. For example, it can be prepared according to the following reaction schemes.
  • Ar 1 to Ar 6 , L 1 , L 2 , R 1 , R 2 , a, b, m, and n are as defined in formula 1, and X represents a halogen.
  • the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the above material may be a host material of a light-emitting layer, specifically a host material of an organic electroluminescent device emitting red light.
  • the above material may be a hole transport material, specifically a hole transport material of an organic electroluminescent device emitting red light.
  • the material may be a hole transport material comprised in the hole transport layer adjacent to the light-emitting layer.
  • the above material can be comprised of the organic electroluminescent compound according to the present disclosure alone, or can further include conventional materials generally used in organic electroluminescent materials.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise at least one organic electroluminescent compound of formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the organic electroluminescent compound of the present disclosure may be comprised in at least one layer of the light-emitting layer, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, the electron transport layer, the electron buffer layer, the electron injection layer, the interlayer, the hole blocking layer, and the electron blocking layer, preferably in at least one layer of the light-emitting layer and the hole transport layer.
  • the organic electroluminescent compound can be used in at least one of the layers.
  • the organic electroluminescent compound of the present disclosure may be comprised as a hole transport material.
  • the compound of the present disclosure may be comprised in the hole transport layer adjacent to the light-emitting layer.
  • the organic electroluminescent compound of the present disclosure may be comprised as a host material.
  • the organic electroluminescent compound of the present disclosure may be used as the hole transport material, and may provide an organic electroluminescent device having excellent lifespan properties, improved luminous efficiency due to an increase of triplet energy, and/or excellent thermal stability due to a decrease of deposition temperature.
  • the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure as a host material can further comprise one or more host compounds besides the organic electroluminescent compound of the present disclosure, and can further comprise one or more dopants.
  • the organic electroluminescent compound of the present disclosure is comprised as a host material (first host material) of the light-emitting layer
  • another compound can be comprised as a second host material.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the host material of a compound other than the organic electroluminescent compound of the present disclosure can be any of the known hosts.
  • the compound which can be comprised as a host material of a light-emitting layer where the compound of the present disclosure is used as a hole transport material, and the compound which can be comprised as a second host material where the compound of the present disclosure is used as a host material may be preferable in terms of luminous efficiency if they are selected from the group consisting of the compounds represented by the following formulas 11 to 16:
  • A represents -O- or -S-
  • R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, or -SiR 25 R 26 R 27 ; in which R 25 to R 27 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-member
  • Y 3 to Y 5 each independently, represent CR 34 or N, preferably at least one of them are N;
  • R 34 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 1 and B 2 each independently, represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 3 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • L 5 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
  • the examples of the second host material are as follows, but are not limited thereto.
  • TPS represents a triphenylsilyl group
  • the dopant comprised in the organic electroluminescent device according to the present disclosure may be preferably at least one phosphorescent dopant.
  • the phosphorescent dopant materials applied to the organic electroluminescent device according to the present disclosure are not particularly limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), may be more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and may be even more preferably ortho-metallated iridium complex compounds.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may be preferably selected from the group consisting of the compounds of formulas 101 to 104 below, but is not limited thereto.
  • L is selected from the following structures:
  • R 100 , R 134 , and R 135 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; adjacent substituents of R 106 to R 109 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and adjacent substituents of R 120 to R
  • R 124 to R 133 and R 136 to R 139 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 124 to R 127 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • X represents CR 11 R 12 , O, or S
  • R 11 and R 12 each independently, represent a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R 208 to R 211 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • f and g each independently, represent an integer of 1 to 3; where f or g is an integer of 2 or more, each R 100 may be the same or different; and
  • s represents an integer of 1 to 3.
  • a composition for preparing an organic electroluminescent device preferably a composition for preparing an organic electroluminescent device emitting red light.
  • the composition is preferably for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device and comprises the compound of the present disclosure.
  • the compound of the present disclosure may be comprised in the composition for preparing a hole transport layer adjacent to the light-emitting layer.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise the composition for preparing the organic electroluminescent device according to the present disclosure.
  • the organic electroluminescent device may further comprise, in addition to the organic electroluminescent compound represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise, besides the organic electroluminescent compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue, a red, or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise a yellow or an orange light-emitting layer.
  • a surface layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole transport layer or the electron blocking layer may also be multi-layers.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each of the multi-layers may use a multi-component of compounds.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer which is further included, may be used as a hole auxiliary layer or an electron blocking layer.
  • the hole auxiliary layer and the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the light-emitting medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the light-emitting medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • the reductive dopant layer may be employed as a charge-generating layer to prepare an organic EL device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as spin coating, dip coating, flow coating methods, etc., can be used.
  • a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
  • a display system for example, for smartphones, tablets, notebooks, PCs, TVs, or vehicles, or a lighting system, for example, an indoor or outdoor lighting system, can be produced.
  • An OLED device comprising the organic electroluminescent compound of the present disclosure was produced as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4' -diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine (compound HI-1) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 90 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine (compound HT-1) was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound C-4 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited as follows.
  • Compound B-198 as below was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-71 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 2 wt% (the amount of dopant) based on the total amount of the dopant and host to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nit of the produced OLED device are provided in Table 2 below.
  • OLED devices were produced in the same manner as in Device Example 1, except for using the compounds shown in Table 2 for the second hole transport layer.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nit of the produced OLED devices are provided in Table 2 below.
  • Comparative Examples 1 to 3 Production of an OLED device comprising a
  • OLED devices were produced in the same manner as in Device Example 1, except for using the compounds shown in Table 2 for the second hole transport layer.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nit of the produced OLED devices are provided in Table 2 below.
  • OLED devices were produced in the same manner as in Device Example 1, except for using the compounds shown in Table 3 for the second hole transport layer, and using compound B-199 for the host.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nit of the produced OLED devices are provided in Table 3 below.
  • Comparative Examples 4 and 5 Production of an OLED device comprising a conventional organic electroluminescent compound
  • OLED devices were produced in the same manner as in Device Example 4, except for using the compounds shown in Table 3 for the second hole transport layer.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nit of the produced OLED devices are provided in Table 3 below.
  • the devices using the organic electroluminescent compound according to the present disclosure in a second hole transport layer have excellent luminous efficiency.
  • the second hole transport layer can also function as a hole auxiliary layer or a light-emitting auxiliary layer.
  • the organic electroluminescent compound according to the present disclosure has a benzo[b]fluorene structure in which the substituent is bonded at the fifth carbon position. Accordingly, the luminous efficiency of the device increases due to the increase of triplet energy, and the thermal stability of the device is excellent due to the decrease of deposition temperature even when the molecular weight of the compounds are the same. This can be verified from Table 4 below.

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Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. L'utilisation du composé électroluminescent organique selon l'invention permet d'obtenir un dispositif électroluminescent organique présentant d'excellentes performances lumineuses.
PCT/KR2017/002959 2016-05-03 2017-03-20 Composé électroluminescent organique et dispositif électroluminescent organique le comportant WO2017191896A1 (fr)

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US16/093,695 US10797243B2 (en) 2016-05-03 2017-03-20 Organic electroluminescent compound and organic electroluminescent device comprising the same
JP2018554333A JP6846438B2 (ja) 2016-05-03 2017-03-20 有機電界発光化合物及びそれを含む有機電界発光デバイス
CN201780024400.8A CN109071413B (zh) 2016-05-03 2017-03-20 有机电致发光化合物和包含其的有机电致发光装置
EP17792799.3A EP3452442B1 (fr) 2016-05-03 2017-03-20 Composé électroluminescent organique et dispositif électroluminescent organique le comportant

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WO2019185061A1 (fr) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation
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CN114163301A (zh) * 2021-10-28 2022-03-11 陕西维世诺新材料有限公司 一种苯并[b]芴衍生物的制备方法及其衍生物

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CN114163301A (zh) * 2021-10-28 2022-03-11 陕西维世诺新材料有限公司 一种苯并[b]芴衍生物的制备方法及其衍生物

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