WO2019147030A1 - Composé électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci Download PDF

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WO2019147030A1
WO2019147030A1 PCT/KR2019/000998 KR2019000998W WO2019147030A1 WO 2019147030 A1 WO2019147030 A1 WO 2019147030A1 KR 2019000998 W KR2019000998 W KR 2019000998W WO 2019147030 A1 WO2019147030 A1 WO 2019147030A1
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substituted
unsubstituted
organic electroluminescent
alkyl
compound
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PCT/KR2019/000998
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English (en)
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Jin-Ri HONG
Young-Mook Lim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020190003137A external-priority patent/KR20190090695A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US16/962,276 priority Critical patent/US20210062081A1/en
Priority to DE112019000238.4T priority patent/DE112019000238T5/de
Priority to JP2020536209A priority patent/JP7252961B2/ja
Priority to CN201980006924.3A priority patent/CN111511879A/zh
Publication of WO2019147030A1 publication Critical patent/WO2019147030A1/fr
Priority to US18/522,818 priority patent/US20240101892A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [ see Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device 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.
  • the organic layer of the organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • the materials used in the organic layer can be classified into 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, an electron injection material, etc., depending on their functions.
  • 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, an electron injection material, etc.
  • holes from the anode and electrons from the cathode are injected into a light-emitting layer by the application of electric voltage, and excitons having high energy are produced by the recombination of the holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light from the energy when the organic light-emitting compound returns to the ground state from the excited state
  • the organic electroluminescent device has a multi-layer structure in order to enhance its efficiency and stability, wherein the selection of compounds contained in the hole transport layer, etc., is recognized as a means for improving device characteristics such as hole transport efficiency to light-emitting layer, luminous efficiency and lifespan.
  • 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
  • JP 2014-047197 A discloses an organic EL device comprising benzofluorenyl amine compounds such as the following structure having hole transporting characters; however, it is still necessary for improving the light-emitting efficiency and lifespan.
  • the object of the present disclosure is firstly, to provide an organic electroluminescent compound being able to prepare an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan; secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
  • R 1 and R 2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring;
  • R 3 and R 4 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, or a substituted or unsubstituted tri(C6-C30)ary
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to each other to form a substituted or unsubstituted ring;
  • a represents an integer from 1 to 4
  • b represents an integer of 1 or 2
  • each of R 3 or each of R 4 may be the same or different;
  • c represents an integer of 1 or 2, when c is an integer of 2, each of Ar 1 or each of Ar 2 may be the same or different.
  • An OLED device using an organic electroluminescent compound according to the present disclosure in a hole transport layer and/or a hole auxiliary layer is significantly improved in terms of luminous efficiency and driving lifespan as compared with OLED devices using a conventional organic electroluminescent compound.
  • the present disclosure relates to the organic electroluminescent compound represented by formula 1 above, the organic electroluminescent material comprising the organic electroluminescent compound, and the organic electroluminescent device comprising the organic electroluminescent material.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any 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.
  • (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.
  • “(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.
  • cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 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, toyly, 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 group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Ge and 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25; having preferably 1 to 4 heteroatoms, and may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); examples of the heteroaryl specifically include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, tri
  • 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-imidazopyridin
  • Halogen includes F, Cl, Br, and I.
  • Ortho position is a compound with substituents, which are adjacent between 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 or unsubstituted ring is meant to be a substituted or unsubstituted, (C3-C30) mono- or polycyclic, alicyclic, aromatic ring or the combination thereof, preferably, may be a substituted or unsubstituted, (C5-C25) mono- or polycyclic, alicyclic, aromatic ring or the combination thereof, more preferably, may be (C5-C18) mono- or polycyclic, alicyclic, aromatic ring or the combination thereof.
  • 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 organic electroluminescent compound according to one embodiment is represented by the following formula 1.
  • R 1 and R 2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring;
  • R 3 and R 4 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, or a substituted or unsubstituted tri(C6-C30)ary
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to each other to form a substituted or unsubstituted ring;
  • a represents an integer from 1 to 4
  • b represents an integer of 1 or 2
  • each of R 3 or each of R 4 may be the same or different;
  • c represents an integer of 1 or 2, when c is an integer of 2, each of Ar 1 or each of Ar 2 may be the same or different.
  • the organic electroluminescent compound of formula 1 may be comprised in a hole transport layer and/or a hole auxiliary layer.
  • the hole auxiliary layer may be placed between the hole transport layer and the light-emitting layer, and may be effective to promote or block the hole transport rate, thereby enabling the charge balance to be controlled.
  • the organic electroluminescent compound of formula 1 forms a resonance structure so that the flow of holes and electrons can be appropriately balanced, thereby the efficiency of the organic electroluminescent device comprising the organic electroluminescent compound can be improved.
  • the organic electroluminescent compound increases hole injection and hole mobility as well as the HOMO energy level by introducing an electron-rich arylamine group into a benzofluorene structure which is easy to recieve holes, thereby further facilitating hole injection.
  • the organic electroluminescent compound of formula 1 may be represented by one of the following formulae 1-1 to 1-6.
  • R 1 to R 4 , Ar 1 , Ar 2 , L, a, and b are as defined in formula 1 above.
  • R 1 and R 2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring; preferably, each independently may be hydrogen, a substituted or unsubstituted (C1-C18)alkyl, or a substituted or unsubstituted (C6-C18)aryl; more preferably, each independently may be hydrogen, a substituted or unsubstituted (C1-C4)alkyl, or a substituted or unsubstituted (C6-C12)aryl.
  • R 1 and R 2 each independently may be hydrogen, methyl, or phenyl.
  • R 3 and R 4 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, or a substituted or unsubstituted or unsubstituted (C
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; preferably, may be a single bond or a substituted or unsubstituted (C6-C18)arylene; more preferably, may be a single bond or a substituted or unsubstituted (C6-C12)arylene.
  • L may be a single bond or phenylene.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to each other to form a substituted or unsubstituted ring; preferably, each independently may be one of the substituents listed in the following group I.
  • a 1 to A 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl; preferably, each independently may be a substituted or unsubstituted (C1-C18)alkyl or a substituted or unsubstituted (C6-C18)aryl; more preferably, each independently may be a substituted or unsubstituted (C1-C4)alkyl or a substituted or unsubstituted (C6-C12)aryl.
  • a 1 to A 3 each independently may be methyl, phenyl, or naphthyl.
  • L' represents a substituted or unsubstituted (C6-C30)arylene or a substituted or unsubstituted (3- to 30-membered)heteroarylene; preferably, each independently may be a substituted or unsubstituted (C6-C25)arylene or a substituted or unsubstituted (5- to 25-membered)heteroarylene; more preferably, each independently may be a substituted or unsubstituted (C6-C18)arylene or a substituted or unsubstituted (5- to 18-membered)heteroarylene.
  • group I represents a bonding position with N.
  • Ar 1 and Ar 2 each independently may be a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (3- to 25-membered)heteroaryl, or may be linked to each other to form a substituted or unsubstituted (C3-C25) mono- or polycyclic aromatic ring, whose at least one carbon atom in the formed aromatic ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; preferably, each independently may be one of the substituents listed in the following group II or may be linked to each other, so that the amine group forms a substituted or unsubstituted carbazole.
  • the organic electroluminescent compound of formula 1 may be represented by one of the following formulae I-1 to I-4.
  • R 1 to R 4 , L, a, and b are as defined in formula 1;
  • R 5 represents hydrogen or -NR x R y ;
  • R x and R y each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • d represents an integer of 1 or 2, when d is 2, each of R 5 may be the same or different.
  • R 5 represents hydrogen or -NR x R y , wherein R x and R y each independently may be hydrogen or a substituted or unsubstituted (C6-C30)aryl; preferably, each independently may be hydrogen or a substituted or unsubstituted (C6-C18)aryl; more preferably, each independently may be hydrogen or a substituted or unsubstituted (C6-C12)aryl.
  • R 5 may be hydrogen or an amine substituented with phenyl.
  • a represents an integer of 1 to 4
  • b represents an integer of 1 or 2
  • each of R 3 and each of R 4 may be the same or different
  • c represents an integer of 1 or 2 when c is 2
  • each of Ar 1 or each of Ar 2 may be the same or different.
  • R 1 and R 2 each independently represent hydrogen, a substituted or unsubstituted (C1-C18)alkyl, or a substituted or unsubstituted (C6-C18)aryl;
  • R 3 and R 4 each independently represent hydrogen or a substituted or unsubstituted (C6-C18)aryl;
  • L represents a single bond or a substituted or unsubstituted (C6-C18)arylene;
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl, or may be linked to each other to form a substituted or unsubstituted (C3-C25) mono- or polycyclic, aromatic ring.
  • R 1 and R 2 each independently represent hydrogen, methyl, or phenyl; R 3 and R 4 each independently represent hydrogen or phenyl; L represents a single bond or phenylene; Ar 1 and Ar 2 each independently represent one of the substituents listed in the group II or may be linked to each other, so that the amine group forms a substituted or unsubstituted carbazole.
  • organic electroluminescent compound of formula 1 may be more specifically illustrated by the following compounds, but are not limited thereto:
  • the compound of formula 1 according to the present disclosure may be produced by a synthetic method known to a person skilled in the art, and for example referring to the following reaction schemes 1 to 3, but is not limited thereto:
  • R 1 to R 4 , Ar 1 , Ar 2 , a, and b are as defined in formula 1, and X 1 , X 2 , and X 4 each independently represent Cl, Br, or I.
  • the present disclosure may provide an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.
  • the organic electroluminescent material may consist of the organic electroluminescent compound of the present disclosure as a sole compound, or may further comprise conventional materials generally used in organic electroluminescent materials.
  • the organic electroluminescent compound of formula 1 may be included as hole transport layer (HTL) materials in the organic electroluminescent device.
  • HTL hole transport layer
  • the organic electroluminescent material of the present disclosure may contain at least one host compound in addition to the organic electroluminescent compound of formula 1.
  • a host compound according to one embodiment can use any of the known phosphorescent hosts.
  • the host material may be particularly preferably selected from the group consisting of the compounds represented by the following formula 2 or 3, but is not limited thereto.
  • Ma represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • A represents S, O, NR 7 or CR 8 R 9 ;
  • Ra to Rd each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstitute
  • R 7 to R 9 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 to c each independently represent an integer of 1 to 4, d represents an integer 1 to 3;
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • the compounds represented by one of formulae 2 and 3 may be illustrated by the following compounds, but are not limited thereto:
  • TPS represents a triphenylsilyl group
  • the organic electroluminescent material may further comprise at least one dopant.
  • the dopont comprised in the organic electroluminescent material of the present disclosure may be at least one phosphorescent or fluorescence dopant, preferably phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more 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 compound represented by the following formula 101 may be used as the dopant, but is not limited thereto:
  • L is selected from the following structure 1 or 2:
  • R 100 to R 103 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 100 to R 103 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine,
  • R 104 to R 107 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R 107 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofur
  • R 201 to R 211 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; R 201 to R 211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring; and
  • n an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto:
  • 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.
  • the organic electroluminescent compound of formula 1 of the present disclosure may be comprised in at least one layer constituting the organic electroluminescent device.
  • the organic layer may comprise a hole transport layer and/or a hole auxiliary layer comprising the organic electroluminescent compound of formula 1.
  • the hole transport layer and/or the hole auxiliary layer may be comprised solely of the organic electroluminescent compound of the present disclosure, or may be comprised of at least two species of the organic electroluminescent compounds; and may be further comprised of conventional materials included in the organic electroluminescent material.
  • the organic layer may comprise a hole transport layer and a hole auxiliary layer, and may further comprise at least one layer selected from a hole injection layer, a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer, wherein each layer may be constituted of multi-layers.
  • the organic layer may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
  • 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 be also applied to the organic electroluminescent device comprising QD (quantum dot).
  • first electrode and the second electrode may be an anode and the other may be a cathode.
  • 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.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole injection layer may be doped as p-dopant.
  • 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 or the electron blocking layer may be multi-layers, wherein each layer may use a plurality of compounds.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
  • the electron injection layer may be doped as n-dopant.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or 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 hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a halogenated metal layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the operation stability for the organic electroluminescent device may be obtained by the surface layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the halogenated metal includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to produce an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device 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 device (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 then 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 then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound A-28 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer (a hole auxiliary layer) having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound H-211 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
  • the two materials were evaporated to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer by doping a dopant in an amount of 2 wt% based on the total amount of the host and dopant.
  • compounds ET-1 and EI-1 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.
  • an Al cathode having a thickness of 1,500 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED device was produced.
  • OLED devices of Device Examples 2 and 3 were produced in the same manner as in Device Example 1, except that compounds A-44 and A-68 were used as the second hole transport material, respectively.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound Ref-1 was used as the second hole transport material.
  • OLED of Device Examples 1 to 3 uisng the organic electroluminescent compound of the present disclosure exhibits far superior effects on the driving voltage, the luminous efficiency, and the lifespan as compared with the OLED of Comparative Example 1, so that the characteristics being able to overcome the conventional problems can be confirmed in that the lifespan is lowered with an increase of efficiency.
  • an organic electroluminescent compound according to the present disclosure when used as material(s) in a hole transport layer and/or a hole auxiliary layer, it is possible to have advantages in increasing the light-emitting efficiency and lifespan as well as lowering the voltage used to emit light of the same luminance.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique comprenant celui-ci. Le composé électroluminescent organique selon la présente invention est contenu dans une couche de transport de trous et/ou une couche auxiliaire de trous, de sorte qu'un dispositif électroluminescent organique ayant un rendement lumineux amélioré et une durée de vie améliorée peut être fabriqué.
PCT/KR2019/000998 2018-01-25 2019-01-24 Composé électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci WO2019147030A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US16/962,276 US20210062081A1 (en) 2018-01-25 2019-01-24 Organic electroluminescent compound and organic electroluminescent device comprising the same
DE112019000238.4T DE112019000238T5 (de) 2018-01-25 2019-01-24 Organische elektrolumineszierende verbindung und diese umfassende organische elektrolumineszierende vorrichtung
JP2020536209A JP7252961B2 (ja) 2018-01-25 2019-01-24 有機エレクトロルミネセント化合物及びこれを含む有機エレクトロルミネセントデバイス
CN201980006924.3A CN111511879A (zh) 2018-01-25 2019-01-24 有机电致发光化合物以及包含其的有机电致发光装置
US18/522,818 US20240101892A1 (en) 2018-01-25 2023-11-29 Organic electroluminescent compound and organic electroluminescent device comprising the same

Applications Claiming Priority (4)

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KR10-2018-0009157 2018-01-25
KR20180009157 2018-01-25
KR1020190003137A KR20190090695A (ko) 2018-01-25 2019-01-10 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2019-0003137 2019-01-10

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US18/522,818 Continuation US20240101892A1 (en) 2018-01-25 2023-11-29 Organic electroluminescent compound and organic electroluminescent device comprising the same

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CN111785841A (zh) * 2020-07-09 2020-10-16 吉林奥来德光电材料股份有限公司 一种有机电致发光器件及其应用
CN111909126A (zh) * 2020-09-10 2020-11-10 吉林奥来德光电材料股份有限公司 基于杂蒽衍生物的有机电致发光材料及制备方法与应用

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KR20140016653A (ko) * 2012-07-30 2014-02-10 삼성디스플레이 주식회사 화합물을 포함하는 유기 발광 소자
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KR20120013278A (ko) * 2009-12-31 2012-02-14 (주)씨에스엘쏠라 유기 광소자 및 이를 위한 유기 광합물
KR20130110347A (ko) * 2012-03-29 2013-10-10 에스에프씨 주식회사 인데노페난트렌 유도체 및 이를 포함하는 유기전계발광소자
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CN111909126A (zh) * 2020-09-10 2020-11-10 吉林奥来德光电材料股份有限公司 基于杂蒽衍生物的有机电致发光材料及制备方法与应用

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