WO2020009398A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDF

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WO2020009398A1
WO2020009398A1 PCT/KR2019/007999 KR2019007999W WO2020009398A1 WO 2020009398 A1 WO2020009398 A1 WO 2020009398A1 KR 2019007999 W KR2019007999 W KR 2019007999W WO 2020009398 A1 WO2020009398 A1 WO 2020009398A1
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substituted
unsubstituted
alkyl
organic electroluminescent
membered
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French (fr)
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Doo-Hyeon Moon
So-mi PARK
Du-Yong PARK
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020190078713A external-priority patent/KR102836228B1/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to DE112019002827.8T priority Critical patent/DE112019002827T5/en
Priority to CN201980045174.0A priority patent/CN112400007A/en
Priority to JP2020573315A priority patent/JP7402831B2/en
Publication of WO2020009398A1 publication Critical patent/WO2020009398A1/en
Anticipated expiration legal-status Critical
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    • 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
    • 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
    • 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
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • the TPD/Alq 3 bilayer small molecule organic electroluminescent device with green-emission which is constituted with a light-emitting layer and a charge transport layer, was first developed by Tang, et al., of Eastman Kodak in 1987. Thereafter, the studies on an organic electroluminescent device have been rapidly commercialized.
  • An organic electroluminescent device (OLED) changes electric energy into light by applying electricity to an organic electroluminescent material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • An organic electroluminescent device has a multi-layer structure including a hole transport zone, a light-emitting layer, and an electron transport zone, etc., in order to improve its efficiency and stability.
  • 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
  • an organic electroluminescent device using these materials has problems of reduction in luminous efficiency and lifespan. It is because, when an organic electroluminescent device is driven under high current, thermal stress occurs between an anode and a hole injection layer, thereby such thermal stress significantly reduces the lifespan of the device. Further, since the organic material used in the hole transport zone has very high hole mobility, there have been problems in that the hole-electron charge balance is broken and the quantum efficiency (cd/A) is lowered. Thus, new compounds that can replace the conventional compound used in a hole transport zone are necessary. In addition, the studies on various materials and devices for improving the luminous efficiency, the driving voltage and/or the lifespan characteristics of the organic electroluminescent device have been conducted.
  • KR 2017-0096770 A merely discloses a compound in which an amine is bonded to a specific position of benzonaphthothiophene or benzonaphthofuran as a compound comprised in a hole transport layer of an organic electroluminescent device.
  • the object of the present disclosure is to provide an organic electroluminescent compound effective for producing an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan.
  • the present inventors found that the aforementioned objective can be achieved due to the organic electroluminescent compound represented by the following formula 1, which decreases the degree of free rotation and increases the rigidity of the molecule through the steric hindrance of the molecule without significantly changing the triplet energy, as compared with the compound disclosed in KR 2017-0096770 A, and then completed the present invention.
  • X represents O or S
  • Ar 1 to Ar 4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or Ar 1 and Ar 2 , and Ar 3 and Ar 4 may be linked to each other to form a ring;
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • R 1 and R 2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • a represents an integer of 1 to 4
  • b represents an integer of 1 to 5
  • each of R 1 and each of R 2 may be the same or different
  • p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, when the sum of p and q is 2, L 1 and L 2 , and Ar 1 to Ar 4 may be the same or different.
  • the organic electroluminescent compound according to the present disclosure can provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifespan.
  • 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 material 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, etc.
  • a hole transport zone means a zone where holes move between the first electrode and the light-emitting layer.
  • the hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may each be a single layer or multi-layers in which two or more layers are stacked.
  • the hole transport zone may include a first hole transport layer and a second hole transport layer.
  • the second hole transport layer may be at least one layer of a plurality of hole transport layers and includes at least one of a hole auxiliary layer, a light-emitting auxiliary, and/or an electron blocking layer.
  • the hole transport zone may include a first hole transport layer and a second hole transport layer.
  • the first hole transport layer may be placed between the first electrode and the light-emitting layer and the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer.
  • the second hole transport layer may be a role of a hole transport layer, a light-emitting auxiliary, a hole auxiliary layer and/or an electron blocking layer.
  • the hole transport layer may be placed between the anode (or hole injection layer) and a light-emitting layer, and may function to smoothly move the holes transferred from the anode to the light-emitting layer and to block the electrons transferred from the cathode to remain in the light-emitting layer.
  • 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. 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 the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer When 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 the 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 the 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, can be used for a light-emitting auxiliary layer, a hole auxiliary layer, and an electron blocking layer, etc.
  • the light-emitting auxiliary layer, the hole auxiliary layer, and/or the electron blocking layer may have an effect of improving the luminous efficiency and/or lifespan of the organic electroluminescent device.
  • (C1-C30)alkyl 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 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n -butyl, isobutyl, tert -butyl, etc.
  • (C2-C30)alkenyl is a linear or branched alkyl having 1 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, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • "(3- to 7-membered)heterocycloalkyl” is a cycloalkyl having 3 to 7 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 7, including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, O, S and N.
  • the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
  • aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, me
  • the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, p-terphenyl-4-
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge.
  • the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated.
  • the above heteroatom may be linked with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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 (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstit
  • the above heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
  • the heteroaryl specifically may include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothioph
  • the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridiny
  • Ortho position is a compound with substituents, which are adjacent to each other, e.g., at the 1 and 2 positions on benzene.
  • Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene.
  • Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
  • 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.
  • the substituents each independently represent (C1-C20)alkyl and/or (C6-C25)aryl. According to another embodiment, the substituents each independently represent at least one of (C1-C10)alkyl and (C6-C18)aryl. For example, the substituents each independently may be at least one of methyl, phenyl, naphthyl, and biphenyl.
  • a ring formed by linked to an adjacent substituent means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents; preferably, may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof.
  • the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S.
  • heteroaryl(ene) and heterocycloalkyl each independently may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si P, and Ge. Further, the above heteroatom may be linked with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-
  • the compound represented by the formula 1 may be represented by any one of the following formulae 2 to 4.
  • X, Ar 1 to Ar 4 , L 1 , L 2 , R 1 , R 2 , a, b, p and q are as defined in formula 1. According to one embodiment, the sum of p and q may be 1.
  • X represents O or S.
  • Ar 1 to Ar 4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or Ar 1 and Ar 2 may be linked to each other to form a ring, and Ar 3 and Ar 4 may be linked to each other to form a ring.
  • Ar 1 to Ar 4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C20)alkylamino, a substituted or unsubstituted mono- or di- (C6-C25)arylamino, or a substituted or unsubstituted (C1-C20)alkyl(C6-C25)arylamino.
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • Ar 1 to Ar 4 each independently may be an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted phenanthrenyl, an unsubstituted naphthylphenyl, phenyl-substituted or unsubstituted dimethylfluorenyl, an unsubstituted diphenylfluorenyl, an unsubstituted terphenyl, spirobifluorenyl, phenyl-substituted or unsubstituted dibenzothiophenyl, dibenzofuranyl, or at least one phenyl- and/or at least one biphenyl-substituted carbazolyl.
  • Ar 1 and Ar 2 , or Ar 3 and Ar 4 each independently may be selected from the following group.
  • Ar 1 when Ar 1 is phenyl, Ar 2 may be any one of the following compounds.
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; according to one embodiment, L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3- to 25-membered)heteroarylene; according to another embodiment, L 1 and L 2 each independently represent a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (3- to 18-membered)heteroarylene. For example, L 1 and L 2 each independently may be a single bond, an unsubstituted phenylene, or an unsubstituted naphthylene.
  • R 1 and R 2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-
  • a represents an integer of 1 to 4
  • b represents an integer of 1 to 5
  • each of R 1 and each of R 2 may be the same or different; and according to one embodiment, a and b may be 1.
  • p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, when the sum of p and q is 2, each of the substituents may be the same or different; and according to one embodiment, the sum of p and q may be 1. For example, when p is 0, q is 1; and when p is 1, q is 0.
  • the compound represented by formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.
  • the organic electroluminescent compound of the present disclosure may be produced by a synthetic method known to a person skilled in the art.
  • the organic electroluminescent compound of the present disclosure may be synthesized as represented by the following reaction schemes 1 to 3, but is not limited thereto.
  • exemplary synthesis examples of the compounds represented by formulae 2 to 4 are described, but they are based on Buchwald-Hartwig cross coupling reaction, Wittig reaction, Ullmann-coupling reaction, Suzuki cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, and Phosphine-mediated reductive cyclization reaction, etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formulae 2 to 4 other than the substituents described in the specific synthesis examples are bonded.
  • the dopant which can be used in combination with the compound of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant is not particulary limited, but may be a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
  • the dopant may use the compound represented by any one of by the following formulae 101 to 103, but is not limited thereto:
  • L is selected from the following structure 1 or 2:
  • R 100 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, halogen, deuterium- or halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to an adjacent substituent(s) to form a ring; specifically, R 106 to R 109 may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring;
  • R 124 to R 127 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring;
  • R 201 to R 211 each independently represent hydrogen, deuterium, halogen, deuterium- or halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or alkyl- or deuterium-substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring;
  • r each independently represent an integer of 1 to 3; when r is 2 or more, each of R 100 may be the same or different; and
  • n an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto.
  • the compound represented by formula 1 of the present disclosure may be contained in at least one layer, e.g., 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, constituting the organic electroluminescent device.
  • the compound represented by formula 1 of the present disclosure may be contained in a hole transport zone, preferably a second hole transport layer of the hole transport zone, but is not limited thereto.
  • the organic electroluminescent material e.g., at least one material of 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, and an electron injection material, may comprise the compound represented by formula 1 above.
  • the materials may be a hole transport zone material.
  • the hole transport zone material may be comprised solely of the organic electroluminescent compound represented by formula 1, or may further comprise conventional materials included in the organic electroluminescent material.
  • An organic electroluminescent material may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • the organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode.
  • One of the first electrode and the second electrode may be an anode and the other may be a cathode.
  • the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the organic layer may comprise at least one 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 device according to the present disclosure layer may comprise the organic electroluminescent compound represented by formula 1 above, and may further comprise conventional materials included in the organic electroluminescent material.
  • the organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 above may represent high luminous efficiency and/or long lifespan characteristics.
  • the present disclosure can provide a display device by using the compound represented by the formula 1. That is, it is possible to manufacture a display device or a lighting device using the compound of the present disclosure.
  • the organic electroluminescent compound of the present disclosure can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.
  • An OLED was produced by using the organic electroluminescent compound of the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and then was stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to be 10 -6 torr.
  • the compound of the following Table 1 (a second hole transport material) was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport zone (an auxiliary layer) having a thickness of 60 nm on the first hole transport zone.
  • a light-emitting layer was then deposited as follows.
  • Compound H-1 as host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-71 as a dopant was introduced into another cell of the apparatus.
  • the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport zone.
  • compounds ET-1 and EI-1 were introduced into another cell, were evaporated at a rate of 1:1, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • compound EI-1 as an electron injection layer having a thickness of 2 nm was deposited on the electron transport layer, and an Al cathode having a thickness of 1500 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer, and thereby the OLED was produced.
  • OLEDs were produced in the same manner as in Device Examples 1 to 3, except that the compound of the following Table 1 was used in the second hole transport zone.
  • the time taken to reduce to 98% at a constant current based on a luminance of 5,000 nit (lifespan; T98), of Device Example 2 and Comparative Example 1, is 98 hrs and 18 hrs, respectively.
  • the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure has a low driving voltage and/or high power efficiency compared with the organic electroluminescent device not comprising the compound of the present disclosure.
  • the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure may have improved lifespan characteristics.

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Abstract

The present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and long lifespan can be provided compared with the conventional organic electroluminescent device.

Description

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
The TPD/Alq3 bilayer small molecule organic electroluminescent device with green-emission, which is constituted with a light-emitting layer and a charge transport layer, was first developed by Tang, et al., of Eastman Kodak in 1987. Thereafter, the studies on an organic electroluminescent device have been rapidly commercialized. An organic electroluminescent device (OLED) changes electric energy into light by applying electricity to an organic electroluminescent material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes. An organic electroluminescent device has a multi-layer structure including a hole transport zone, a light-emitting layer, and an electron transport zone, etc., in order to improve its efficiency and stability.
In addition, the studies on the new compounds capable of improving the performance of the organic electroluminescent device have been actively conducted since the performance of an organic electroluminescent device depends largely on the compound contained in each zone or layer thereof. For example, copper phthalocyanine (CuPc), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N′-diphenyl-N,N′-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TPD), 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc., were used as a compound comprised in a hole transport zone in an organic electroluminescent device. However, an organic electroluminescent device using these materials has problems of reduction in luminous efficiency and lifespan. It is because, when an organic electroluminescent device is driven under high current, thermal stress occurs between an anode and a hole injection layer, thereby such thermal stress significantly reduces the lifespan of the device. Further, since the organic material used in the hole transport zone has very high hole mobility, there have been problems in that the hole-electron charge balance is broken and the quantum efficiency (cd/A) is lowered. Thus, new compounds that can replace the conventional compound used in a hole transport zone are necessary. In addition, the studies on various materials and devices for improving the luminous efficiency, the driving voltage and/or the lifespan characteristics of the organic electroluminescent device have been conducted.
KR 2017-0096770 A merely discloses a compound in which an amine is bonded to a specific position of benzonaphthothiophene or benzonaphthofuran as a compound comprised in a hole transport layer of an organic electroluminescent device.
The object of the present disclosure is to provide an organic electroluminescent compound effective for producing an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan.
The present inventors found that the aforementioned objective can be achieved due to the organic electroluminescent compound represented by the following formula 1, which decreases the degree of free rotation and increases the rigidity of the molecule through the steric hindrance of the molecule without significantly changing the triplet energy, as compared with the compound disclosed in KR 2017-0096770 A, and then completed the present invention.
Figure PCTKR2019007999-appb-I000001
In formula 1,
X represents O or S;
Ar1 to Ar4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or Ar1 and Ar2, and Ar3 and Ar4 may be linked to each other to form a ring;
L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are 2 or more, each of R1 and each of R2 may be the same or different; and
p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, when the sum of p and q is 2, L1 and L2, and Ar1 to Ar4 may be the same or different.
The organic electroluminescent compound according to the present disclosure can provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifespan.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The term "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 material layer constituting an organic electroluminescent device, as necessary.
The term "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. For example, 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, etc.
The term "a hole transport zone" means a zone where holes move between the first electrode and the light-emitting layer. For example, the hole transport zone may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may each be a single layer or multi-layers in which two or more layers are stacked. According to one embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer. The second hole transport layer may be at least one layer of a plurality of hole transport layers and includes at least one of a hole auxiliary layer, a light-emitting auxiliary, and/or an electron blocking layer. Further, according to another embodiment, the hole transport zone may include a first hole transport layer and a second hole transport layer. The first hole transport layer may be placed between the first electrode and the light-emitting layer and the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer. The second hole transport layer may be a role of a hole transport layer, a light-emitting auxiliary, a hole auxiliary layer and/or an electron blocking layer.
The hole transport layer may be placed between the anode (or hole injection layer) and a light-emitting layer, and may function to smoothly move the holes transferred from the anode to the light-emitting layer and to block the electrons transferred from the cathode to remain in the light-emitting layer. 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. 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 the hole transport, or for preventing the overflow of electrons. When 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 the electron transport, or for preventing the overflow of holes. In addition, 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 the hole injection rate), thereby enabling the charge balance to be controlled.
Also, 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. When the organic electroluminescent device contains two or more hole transport layers, the hole transport layer, which is further included, can be used for a light-emitting auxiliary layer, a hole auxiliary layer, and an electron blocking layer, etc. The light-emitting auxiliary layer, the hole auxiliary layer, and/or the electron blocking layer may have an effect of improving the luminous efficiency and/or lifespan of the organic electroluminescent device.
Herein, "(C1-C30)alkyl" 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 20, and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30)alkenyl" is a linear or branched alkyl having 1 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, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7-membered)heterocycloalkyl" is a cycloalkyl having 3 to 7 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 7, including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, O, S and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. "(C6-C30)aryl(ene)" is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure. Examples of the aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, etc. More specifically, the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, etc.
Herein, "(3- to 30-membered)heteroaryl(ene)" is an aryl having 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge. The above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated. The above heteroatom may be linked with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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 (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, and a substituted or unsubstituted (C1-C30)alkyl(C6-30)arylamino. Also, the above heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure. Examples of the heteroaryl specifically may include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl, germafluorenyl, etc. More specifically, the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl , 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acrylidinyl, 2-acrylidinyl, 3-acrylidinyl, 4-acrylidinyl, 9-acrylidinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl, etc. "Halogen" includes F, Cl, Br, and I.
Herein, "ortho (o)," "meta (m)," and "para (p)" are meant to signify the substitution position of all substituents. Ortho position is a compound with substituents, which are adjacent to each other, e.g., at the 1 and 2 positions on benzene. Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene. Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
In addition, "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. The substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3-to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino each independently are at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl-substituted or unsubstituted (3- to 30-membered)heteroaryl, (3- to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, (C1-C30)alkyl-substituted or unsubstituted mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment, the substituents each independently represent (C1-C20)alkyl and/or (C6-C25)aryl. According to another embodiment, the substituents each independently represent at least one of (C1-C10)alkyl and (C6-C18)aryl. For example, the substituents each independently may be at least one of methyl, phenyl, naphthyl, and biphenyl.
Herein, "a ring formed by linked to an adjacent substituent" means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents; preferably, may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S.
In the formulae of the present disclosure, heteroaryl(ene) and heterocycloalkyl each independently may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si P, and Ge. Further, the above heteroatom may be linked with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, and a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
The compound represented by the formula 1 may be represented by any one of the following formulae 2 to 4.
Figure PCTKR2019007999-appb-I000002
Figure PCTKR2019007999-appb-I000003
In formulae 2 to 4, X, Ar1 to Ar4, L1, L2, R1, R2, a, b, p and q are as defined in formula 1. According to one embodiment, the sum of p and q may be 1.
In formulae 1 to 4, X represents O or S.
In formulae 1 to 4, Ar1 to Ar4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or Ar1 and Ar2 may be linked to each other to form a ring, and Ar3 and Ar4 may be linked to each other to form a ring. According to one embodiment, Ar1 to Ar4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C20)alkylamino, a substituted or unsubstituted mono- or di- (C6-C25)arylamino, or a substituted or unsubstituted (C1-C20)alkyl(C6-C25)arylamino. According to another embodiment, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl. For example, Ar1 to Ar4 each independently may be an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted phenanthrenyl, an unsubstituted naphthylphenyl, phenyl-substituted or unsubstituted dimethylfluorenyl, an unsubstituted diphenylfluorenyl, an unsubstituted terphenyl, spirobifluorenyl, phenyl-substituted or unsubstituted dibenzothiophenyl, dibenzofuranyl, or at least one phenyl- and/or at least one biphenyl-substituted carbazolyl.
According to one embodiment, Ar1 and Ar2, or Ar3 and Ar4 each independently may be selected from the following group. For example, when Ar1 is phenyl, Ar2 may be any one of the following compounds.
Figure PCTKR2019007999-appb-I000004
Figure PCTKR2019007999-appb-I000005
Figure PCTKR2019007999-appb-I000006
Figure PCTKR2019007999-appb-I000007
Figure PCTKR2019007999-appb-I000008
Figure PCTKR2019007999-appb-I000009
Figure PCTKR2019007999-appb-I000010
Figure PCTKR2019007999-appb-I000011
Figure PCTKR2019007999-appb-I000012
In formulae 1 to 4, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; according to one embodiment, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3- to 25-membered)heteroarylene; according to another embodiment, L1 and L2 each independently represent a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (3- to 18-membered)heteroarylene. For example, L1 and L2 each independently may be a single bond, an unsubstituted phenylene, or an unsubstituted naphthylene.
In formulae 1 to 4, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; according to one embodiment, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl; according to another embodiment, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, an unsubstitued (C1-C10)alkyl, an unsubstitued (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl. For example, R1 and R2 may be hydrogen.
In formulae 1 to 4, a represents an integer of 1 to 4, b represents an integer of 1 to 5, when a and b each are 2 or more, each of R1 and each of R2 may be the same or different; and according to one embodiment, a and b may be 1.
In formulae 1 to 4, p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, when the sum of p and q is 2, each of the substituents may be the same or different; and according to one embodiment, the sum of p and q may be 1. For example, when p is 0, q is 1; and when p is 1, q is 0.
The compound represented by formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.
Figure PCTKR2019007999-appb-I000013
Figure PCTKR2019007999-appb-I000014
Figure PCTKR2019007999-appb-I000015
Figure PCTKR2019007999-appb-I000016
Figure PCTKR2019007999-appb-I000017
Figure PCTKR2019007999-appb-I000018
Figure PCTKR2019007999-appb-I000019
Figure PCTKR2019007999-appb-I000020
Figure PCTKR2019007999-appb-I000021
Figure PCTKR2019007999-appb-I000022
Figure PCTKR2019007999-appb-I000023
Figure PCTKR2019007999-appb-I000024
Figure PCTKR2019007999-appb-I000025
Figure PCTKR2019007999-appb-I000026
Figure PCTKR2019007999-appb-I000027
Figure PCTKR2019007999-appb-I000028
Figure PCTKR2019007999-appb-I000029
Figure PCTKR2019007999-appb-I000030
Figure PCTKR2019007999-appb-I000031
Figure PCTKR2019007999-appb-I000032
Figure PCTKR2019007999-appb-I000033
Figure PCTKR2019007999-appb-I000034
Figure PCTKR2019007999-appb-I000035
Figure PCTKR2019007999-appb-I000036
Figure PCTKR2019007999-appb-I000037
Figure PCTKR2019007999-appb-I000038
Figure PCTKR2019007999-appb-I000039
Figure PCTKR2019007999-appb-I000040
Figure PCTKR2019007999-appb-I000041
Figure PCTKR2019007999-appb-I000042
Figure PCTKR2019007999-appb-I000043
Figure PCTKR2019007999-appb-I000044
Figure PCTKR2019007999-appb-I000045
Figure PCTKR2019007999-appb-I000046
Figure PCTKR2019007999-appb-I000047
The organic electroluminescent compound of the present disclosure may be produced by a synthetic method known to a person skilled in the art. For example, the organic electroluminescent compound of the present disclosure may be synthesized as represented by the following reaction schemes 1 to 3, but is not limited thereto.
[Reaction Scheme 1]
Figure PCTKR2019007999-appb-I000048
Figure PCTKR2019007999-appb-I000049
[Reaction Scheme 2]
Figure PCTKR2019007999-appb-I000050
Figure PCTKR2019007999-appb-I000051
[Reaction Scheme 3]
Figure PCTKR2019007999-appb-I000052
Figure PCTKR2019007999-appb-I000053
In reaction schemes 1 to 3, X, Ar1 to Ar4, L1, L2, R1, R2, a, b, p and q are as defined in formula 1.
As described above, exemplary synthesis examples of the compounds represented by formulae 2 to 4 according to one embodiment are described, but they are based on Buchwald-Hartwig cross coupling reaction, Wittig reaction, Ullmann-coupling reaction, Suzuki cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and Phosphine-mediated reductive cyclization reaction, etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formulae 2 to 4 other than the substituents described in the specific synthesis examples are bonded.
The dopant which can be used in combination with the compound of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant is not particulary limited, but may be a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
The dopant may use the compound represented by any one of by the following formulae 101 to 103, but is not limited thereto:
Figure PCTKR2019007999-appb-I000054
Figure PCTKR2019007999-appb-I000055
wherein, L is selected from the following structure 1 or 2:
Figure PCTKR2019007999-appb-I000056
R100 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
R101 to R109 and R111 to R123 each independently represent hydrogen, deuterium, halogen, deuterium- or halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to an adjacent substituent(s) to form a ring; specifically, R106 to R109 may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring; R120 to R123 may be linked to an adjacent substituent(s) to form a ring, e.g., R120 and R121 may be linked to each other to form at least one of alkyl-, aryl-, aralkyl- and alkylaryl-substituted or unsubstituted benzene ring, or at least one alkyl-substituted or unsubstituted fluorene ring, dibenzofuran ring, or dibenzothiophene ring;
R124 to R127 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring;
R201 to R211 each independently represent hydrogen, deuterium, halogen, deuterium- or halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or alkyl- or deuterium-substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a ring, e.g., alkyl-substituted or unsubstituted indene ring, alkyl-substituted or unsubstituted benzothiophene ring, or alkyl-substituted or unsubstituted benzofuran ring;
r each independently represent an integer of 1 to 3; when r is 2 or more, each of R100 may be the same or different; and
n represents an integer of 1 to 3.
The specific examples of the dopant compound include the following, but are not limited thereto.
Figure PCTKR2019007999-appb-I000057
Figure PCTKR2019007999-appb-I000058
Figure PCTKR2019007999-appb-I000059
Figure PCTKR2019007999-appb-I000060
Figure PCTKR2019007999-appb-I000061
Figure PCTKR2019007999-appb-I000062
Figure PCTKR2019007999-appb-I000063
Figure PCTKR2019007999-appb-I000064
Figure PCTKR2019007999-appb-I000065
Figure PCTKR2019007999-appb-I000066
Figure PCTKR2019007999-appb-I000067
Figure PCTKR2019007999-appb-I000068
Figure PCTKR2019007999-appb-I000069
Figure PCTKR2019007999-appb-I000070
Figure PCTKR2019007999-appb-I000071
Figure PCTKR2019007999-appb-I000072
Figure PCTKR2019007999-appb-I000073
Figure PCTKR2019007999-appb-I000074
Figure PCTKR2019007999-appb-I000075
Figure PCTKR2019007999-appb-I000076
Figure PCTKR2019007999-appb-I000077
Figure PCTKR2019007999-appb-I000078
Figure PCTKR2019007999-appb-I000079
Figure PCTKR2019007999-appb-I000080
Figure PCTKR2019007999-appb-I000081
Figure PCTKR2019007999-appb-I000082
Figure PCTKR2019007999-appb-I000083
The compound represented by formula 1 of the present disclosure may be contained in at least one layer, e.g., 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, constituting the organic electroluminescent device. In addition, the compound represented by formula 1 of the present disclosure may be contained in a hole transport zone, preferably a second hole transport layer of the hole transport zone, but is not limited thereto.
The organic electroluminescent material, e.g., at least one material of 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, and an electron injection material, may comprise the compound represented by formula 1 above. The materials may be a hole transport zone material. The hole transport zone material may be comprised solely of the organic electroluminescent compound represented by formula 1, or may further comprise conventional materials included in the organic electroluminescent material.
An organic electroluminescent material according to one embodiment may be used as light-emitting materials for a white organic light-emitting device. The white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units. In addition, the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode and the other may be a cathode. Wherein, the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode. The organic layer may comprise at least one 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 device according to the present disclosure layer may comprise the organic electroluminescent compound represented by formula 1 above, and may further comprise conventional materials included in the organic electroluminescent material. The organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 above may represent high luminous efficiency and/or long lifespan characteristics.
In addition, the present disclosure can provide a display device by using the compound represented by the formula 1. That is, it is possible to manufacture a display device or a lighting device using the compound of the present disclosure. Specifically, the organic electroluminescent compound of the present disclosure can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.
Hereinafter, the preparation method of a compound according to the present disclosure, and the properties thereof will be represented in detail with reference to the representative compounds of the present disclosure in order to understand the present disclosure in detail. However, the present disclosure is not limited to the following examples.
[Example 1] Preparation of Compound C-123
Figure PCTKR2019007999-appb-I000084
Figure PCTKR2019007999-appb-I000085
1) Preparation of Compound 1-1
Compound A (37 g, 205.05 mmol), 2-bromo-6-chlorobenzaldehyde (30 g, 136.7 mmol), tetrakis(triphenylphosphine)palladium (4.7 g, 4.1 mmol), potassium carbonate (47.2 g, 341.75 mmol), 400 mL of tetrahydrofuran, and 100 mL of distilled water were added into a reaction vessel and stirred for 4 hours at 100℃. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. After the extracted organic layer was dried with magnesium sulfate, the solvent was removed therefrom with a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain compound 1-1 (35 g, yield: 94%).
2) Preparation of Compound 1-2
Compound 1-1 (35 g, 128.32 mmol) and (methoxymethyl)triphenylphosphinium chloride (66 g, 192.48 mmol) were added into a reaction vessel in 350 mL of tetrahydrofuran; thereafter, 193 mL of potassium tert-butoxide (1M) was added dropwise to the mixture at 0℃. After completion of dropwise addition, the reaction temperature was slowly raised to room temperature and further the mixture was stirred for 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and the extracted organic layer was dried with magnesium sulfate. Thereafter, the solvent was removed therefrom with a rotary evaporator and then the remaining product was purified by column chromatography to obtain compound 1-2 (31g, yield: 80%).
3) Preparation of Compound 1-3
After compound 1-2 (31 g, 103.06 mmol) was dissolved in chlorobenzene, 3.1 mL of Eaton's reagent was added slowly dropwise to a reaction vessel. After completion of dropwise addition, the mixture was further stirred for 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. After the extracted organic layer was dried with magnesium sulfate, the solvent was removed therefrom with a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain compound 1-3 (24.4 g, yield: 88%).
4) Preparation of Compound C-123
Compound 1-3 (3.5 g, 13.02 mmol), N,9-diphenyl-9H-carbazole-2-amine (4.8 g, 14.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.6 g, 0.65 mmol), tri-tert-butylphosphine (0.3 mL, 1.30 mmol), sodium tert-butoxide (1.9 g, 19.53 mmol), and 65 mL of toluene were added into a reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-123 (6 g, yield: 81%).
Figure PCTKR2019007999-appb-I000086
[Example 2] Preparation of Compound C-124
Figure PCTKR2019007999-appb-I000087
Compound 1-3 (3.0 g, 11.16 mmol), N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole-2-amine (5.0 g, 12.28 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.5 g, 0.56 mmol), tri-tert-butylphosphine (0.3 mL, 1.12 mmol), sodium tert-butoxide (1.6 g, 16.74 mmol), and 56 mL of toluene were added into a reaction vessel and refluxed for 1 hour. The reaction mixture was cooled to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-124 (2 g, yield: 28%).
Figure PCTKR2019007999-appb-I000088
[Example 3] Preparation of Compound C-125
Figure PCTKR2019007999-appb-I000089
Compound 1-3 (3.5 g, 13.02 mmol), N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine (5.2 g, 14.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.6 g, 0.65 mmol), tri-tert-butylphosphine (0.3 mL, 1.30 mmol), sodium tert-butoxide (1.9 g, 19.53 mmol), and 65 mL of toluene were added into a reaction vessel and refluxed for1 hour. The reaction mixture was cooled to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain the compound C-125 (1.3 g, yield: 17%).
Figure PCTKR2019007999-appb-I000090
Hereinafter, the properties of an organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure will be explained in order to understand the present disclosure in detail. However, the following examples description is intended to explain the characteristics of an OLED according to the present disclosure in order to understand the present disclosure in detail, and the present disclosure is not meant in any way to restrict the following examples.
[Device Examples 1 to 3] Producing an OLED including the organic
electroluminescent compound according to the present disclosure
An OLED was produced by using the organic electroluminescent compound of the present disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to be 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 90 nm on the ITO substrate. Compound HI-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Next, compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole transport zone having a thickness of 10 nm on the second hole injection layer. The compound of the following Table 1 (a second hole transport material) was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport zone (an auxiliary layer) having a thickness of 60 nm on the first hole transport zone. After forming the hole injection layers and the hole transport zones, a light-emitting layer was then deposited as follows. Compound H-1 as host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-71 as a dopant was introduced into another cell of the apparatus. The dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport zone. Next, compounds ET-1 and EI-1 were introduced into another cell, were evaporated at a rate of 1:1, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. Next, compound EI-1 as an electron injection layer having a thickness of 2 nm was deposited on the electron transport layer, and an Al cathode having a thickness of 1500 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer, and thereby the OLED was produced.
[Comparative Examples 1 and 2] Producing an OLED using the compound not
according to the present disclosure
OLEDs were produced in the same manner as in Device Examples 1 to 3, except that the compound of the following Table 1 was used in the second hole transport zone.
The compounds used in Device Examples 1 to 3 and Comparative Examples 1 and 2 are shown as follows.
Figure PCTKR2019007999-appb-I000091
Figure PCTKR2019007999-appb-I000092
Figure PCTKR2019007999-appb-I000093
Figure PCTKR2019007999-appb-I000094
The results of the driving voltage, the power efficiency, and CIE color coordinates at a luminance of 1,000 nit of the OLEDs produced as described above, are shown in the following Table 1.
Figure PCTKR2019007999-appb-I000095
In addition, the time taken to reduce to 98% at a constant current based on a luminance of 5,000 nit (lifespan; T98), of Device Example 2 and Comparative Example 1, is 98 hrs and 18 hrs, respectively.
In the Device Examples and Comparative Examples above, it was confirmed that the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure has a low driving voltage and/or high power efficiency compared with the organic electroluminescent device not comprising the compound of the present disclosure. At the same time or selectively, the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure may have improved lifespan characteristics.

Claims (8)

  1. An organic electroluminescent compound represented by the following formula 1:
    Figure PCTKR2019007999-appb-I000096
    wherein,
    X represents O or S;
    Ar1 to Ar4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or Ar1 and Ar2, and Ar3 and Ar4 may be linked to each other to form a ring;
    L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
    R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
    a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are 2 or more, each of R1 and each of R2 may be the same or different; and
    p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, and when the sum of p and q is 2, L1 and L2, and Ar1 to Ar4 may be the same or different.
  2. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino each independently represent at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl-substituted or unsubstituted (3- to 30-membered)heteroaryl, (3- to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, (C1-C30)alkyl-substituted or unsubstituted mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.
  3. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulae 2 to 4:
    Figure PCTKR2019007999-appb-I000097
    Figure PCTKR2019007999-appb-I000098
    wherein,
    p and q each independently represent 0 or 1, whrein the sum of p and q is 1; and
    X, Ar1 to Ar4, L1, L2, R1, R2, a, and b are as defined in claim 1.
  4. The organic electroluminescent compound according to claim 1, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C20)alkylamino, a substituted or unsubstituted mono- or di- (C6-C25)arylamino, or a substituted or unsubstituted (C1-C20)alkyl(C6-C25)arylamino;
    L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3- to 25-membered)heteroarylene;
    R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl; and
    p and q each independently represent 0 or 1, provided that the sum of p and q is 1.
  5. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2019007999-appb-I000099
    Figure PCTKR2019007999-appb-I000100
    Figure PCTKR2019007999-appb-I000101
    Figure PCTKR2019007999-appb-I000102
    Figure PCTKR2019007999-appb-I000103
    Figure PCTKR2019007999-appb-I000104
    Figure PCTKR2019007999-appb-I000105
    Figure PCTKR2019007999-appb-I000106
    Figure PCTKR2019007999-appb-I000107
    Figure PCTKR2019007999-appb-I000108
    Figure PCTKR2019007999-appb-I000109
    Figure PCTKR2019007999-appb-I000110
    Figure PCTKR2019007999-appb-I000111
    Figure PCTKR2019007999-appb-I000112
    Figure PCTKR2019007999-appb-I000113
    Figure PCTKR2019007999-appb-I000114
    Figure PCTKR2019007999-appb-I000115
    Figure PCTKR2019007999-appb-I000116
    Figure PCTKR2019007999-appb-I000117
    Figure PCTKR2019007999-appb-I000118
    Figure PCTKR2019007999-appb-I000119
    Figure PCTKR2019007999-appb-I000120
    Figure PCTKR2019007999-appb-I000121
    Figure PCTKR2019007999-appb-I000122
    Figure PCTKR2019007999-appb-I000123
    Figure PCTKR2019007999-appb-I000124
    Figure PCTKR2019007999-appb-I000125
    Figure PCTKR2019007999-appb-I000126
    Figure PCTKR2019007999-appb-I000127
    Figure PCTKR2019007999-appb-I000128
    Figure PCTKR2019007999-appb-I000129
    Figure PCTKR2019007999-appb-I000130
    Figure PCTKR2019007999-appb-I000131
    Figure PCTKR2019007999-appb-I000132
    Figure PCTKR2019007999-appb-I000133
  6. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
  7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
  8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is contained in a hole transport zone.
PCT/KR2019/007999 2018-07-03 2019-07-02 Organic electroluminescent compound and organic electroluminescent device comprising the same Ceased WO2020009398A1 (en)

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