WO2020054989A1 - 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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WO2020054989A1
WO2020054989A1 PCT/KR2019/010420 KR2019010420W WO2020054989A1 WO 2020054989 A1 WO2020054989 A1 WO 2020054989A1 KR 2019010420 W KR2019010420 W KR 2019010420W WO 2020054989 A1 WO2020054989 A1 WO 2020054989A1
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substituted
unsubstituted
group
alkyl
organic electroluminescent
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PCT/KR2019/010420
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French (fr)
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Ji-Won UM
Hong-Se OH
Ga-Won Lee
Sang-Hee Cho
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020190080081A external-priority patent/KR102534322B1/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN201980060088.7A priority Critical patent/CN112714766B/en
Publication of WO2020054989A1 publication Critical patent/WO2020054989A1/en

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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C07—ORGANIC CHEMISTRY
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic electroluminescent device was first developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • An organic electroluminescent device changes electric energy into light by applying electricity to an organic luminous material, and commonly has a structure comprising an anode, a cathode, and an organic layer between the two electrodes.
  • the organic layer of the OLED 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, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., as necessary.
  • 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 (containing host and dopant materials), 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 (containing host and dopant materials), 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 an energy when the
  • the most important factor determining luminous efficiency of an OLED is light-emitting materials.
  • the light-emitting materials are required to have the following features: high quantum efficiency, high mobility of an electron and a hole, and uniformity and stability of the formed light-emitting material layer.
  • the light-emitting material is classified into blue, green, and red light-emitting materials according to the light-emitting color, and further includes yellow or orange light-emitting materials.
  • the light-emitting material is classified into a host material and a dopant material in a functional aspect.
  • a host material as a solvent in a solid state and an energy transmitter should have high purity and a suitable molecular weight in order to be deposited under vacuum.
  • a host material is required to have high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve a long lifetime, and easy formability of an amorphous thin film.
  • the objective of the present disclosure is to provide an organic electroluminescent compound having good thermal stability, and effective for producing an organic electroluminescent device having low driving voltage, high luminous efficiency and/or long lifetime properties.
  • a compound having a low glass transition temperature (Tg) may reduce the charge mobility in a thin film and deteriorate the performance of an OLED device.
  • Tg glass transition temperature
  • the present inventors have developed a novel organic electroluminescent compound having a planar main core, which can assist pi-pi stacking in a vacuum deposition layer to lead to rapid charge mobility, and having a high Tg in spite of its low molecular weight, which can provide excellent morphological stability.
  • the present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
  • a 1 to A 11 each independently, represent N or CR 1 ;
  • X 1 represents N, NR 3 or CR 4 , X 2 represents N or C; with the proviso that at least one of X 1 and X 2 contains N;
  • R 1 , R 3 , R 4 , Ar 1 and Ar 2 each independently, represent hydrogen, deuterium, a halogen, a 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
  • L 1 each independently, represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene.
  • the organic electroluminescent compound according to the present disclosure has good thermal stability, and in addition or alternatively, can provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifetime properties.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) 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 meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
  • the above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be 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, and more preferably 2 to 10.
  • the above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • the term "(C3-C30)cycloalkyl(ene)" is meant to be 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 meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N.
  • the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is meant to be 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 25, more preferably 6 to 18.
  • the above aryl may be partially saturated, and may comprise a spiro structure.
  • the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
  • the aryl may include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a benzanthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a naphthacenyl group, a pyrenyl group, a 1-chrysenyl group, a 2-chrysenyl group, a 3-chrysenyl group, a 4-chrysenyl group, a 5-chrysenyl group, a 6-chrysenyl group, a benzo[c]phenanthryl group, a benzo[g]chrysenyl group, a 1-triphenylenyl group, a 2-triphenylen
  • (3- to 30-membered)heteroaryl(ene) is meant to be an aryl group having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
  • the above heteroaryl 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); and may comprise a spiro structure.
  • the above heteroaryl may include a monocyclic ring-type heteroaryl such as 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 such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindo
  • the heteroaryl may include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 6-pyrimidinyl group, a 1,2,3-triazin-4-yl group, a 1,2,4-triazin-3-yl group, a 1,3,5-triazin-2-yl group, a 1-imidazolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 1-indolidinyl group, a 2-indolidinyl group, a 3-indolidinyl group, a 5-indolidinyl group, a 6-indolidinyl group, a 7-indolidinyl group, an 8-indolidinyl group, a 2-imidazopyr
  • ortho indicates that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called an ortho position.
  • Meta indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is called a meta position.
  • Para indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is called a para position.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e., a substituent.
  • the substituents are at least one selected from the group consisting of a (C1-C20)alkyl; a (C6-C25)aryl and a (3- to 25-membered)heteroaryl.
  • the substituents, each independently are at least one selected from the group consisting of a (C1-C10)alkyl, a (C6-C18)aryl and a (5- to 20-membered)heteroaryl.
  • the substituents, each independently may be at least one selected from the group consisting of a methyl, a phenyl, a naphthyl, a biphenyl, and a dibenzofuranyl.
  • a ring formed by a linkage of adjacent substituents means that at least two adjacent substituents are linked to or fused with each other to form a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof; and preferably, a substituted or unsubstituted mono- or polycyclic (3- to 26-membered) alicyclic or aromatic ring, or the combination thereof.
  • the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.
  • the heteroaryl(ene) and the heterocycloalkyl may contain at least one heteroatom selected from B, N, O, S, Si, and P.
  • the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, a halogen, a 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)aryls
  • a 1 to A 11 each independently, represent N or CR 1 . According to one embodiment of the present disclosure, A 1 to A 11 , each independently, represent CR 1 .
  • R 1 each independently, represents hydrogen, deuterium, a halogen, a 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
  • each of R 1 may be the same or different.
  • R 1 each independently, represents hydrogen, deuterium, an unsubstituted (C1-C20)alkyl, an unsubstituted (C6-C25)aryl, or an unsubstituted (5- to 25-membered)heteroaryl; or two or more adjacent R 1 ’s may be linked to each other to form a ring(s).
  • R 1 each independently, represents hydrogen, or two or more adjacent R 1 ’s may be linked to each other to form a ring(s).
  • the ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof; and preferably, an unsubstituted mono- or polycyclic (5- to 25-membered) alicyclic or aromatic ring, or the combination thereof.
  • the ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.
  • the ring may be a benzene ring, a pyridine ring, a benzofuran ring, or a benzothiophene ring, etc.
  • X 1 represents N, NR 3 or CR 4
  • X 2 represents N or C; with the proviso that at least one of X 1 and X 2 contains N.
  • X 1 represents N, NR 3 or CR 4
  • X 2 represents C
  • X 1 represents N or NR 3
  • X 1 may represent N or CR 4
  • X 2 represents C
  • X 1 may represent NR 3 .
  • formula 1 represents a single bond or a double bond, respectively, depending on the substituent bonded.
  • X 2 represents N, linked to X 2 represents a single bond
  • X 1 represents N, linked to X 1 represents a double bond.
  • R 3 and R 4 each independently, represent hydrogen, deuterium, a halogen, a 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
  • R 3 and R 4 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 3 and R 4 each independently, represent hydrogen, deuterium, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl.
  • R 3 each independently, may represent a phenyl
  • R 4 each independently, may represent hydrogen.
  • Ar 1 and Ar 2 each independently, represent hydrogen, deuterium, a halogen, a 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
  • Ar 1 and Ar 2 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- 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 each independently, represents an unsubstituted (C6-C18)aryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s) and/or a (3- to 20-membered)heteroaryl(s); or a di(C6-C18)arylamino unsubstituted or substituted with a (C1-C6)alkyl(s).
  • Ar 2 each independently, represents hydrogen, deuterium, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl.
  • Ar 1 each independently, represents a phenyl; a biphenyl; a pyridyl unsubstituted or substituted with a phenyl(s); a pyrimidinyl unsubstituted or substituted with a phenyl(s); a triazinyl unsubstituted or substituted with at least one of a phenyl(s), a biphenyl(s), a naphthyl(s), and a dibenzofuranyl(s); a quinazolinyl substituted with a phenyl(s); a quinoxalinyl substituted with a phenyl(s); a carbazolyl; a dibenzofuranyl(s); a quinazol
  • L 1 each independently, represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene.
  • L 1 each independently, represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene.
  • L 1 each independently, represents a single bond, an unsubstituted (C6-C18)arylene, or a (5- to 20-membered)heteroarylene unsubstituted or substituted with a (C6-C10)aryl(s).
  • L 1 each independently, represents a single bond, a phenylene, a naphthylene, a biphenylene, a pyridylene, a pyrimidinylene substituted with a phenyl(s), a triazinylene substituted with a phenyl(s), a quinazolinylene, a quinoxalinylene, a benzoquinazolinylene, or a benzoquinoxalinylene, etc.
  • the compound represented by formula 1 may be represented by any one of the following formulas 2 to 8.
  • Y 1 represents NR 5 , O, S or CR 6 R 7 . According to one embodiment of the present disclosure, Y 1 represents O or S.
  • T 1 to T 4 each independently, represent CR 8 or N.
  • R 1 , R 2 , and R 5 to R 8 each independently, represent hydrogen, deuterium, a halogen, a 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,
  • each of R 1 , each of R 2 , and each of R 8 may be the same or different.
  • R 1 , R 2 , and R 5 to R 8 each independently, represent hydrogen, deuterium, an unsubstituted (C1-C20)alkyl, an unsubstituted (C6-C25)aryl, or an unsubstituted (3- to 25-membered)heteroaryl.
  • R 1 , R 2 , and R 5 to R 8 each independently, represent hydrogen or deuterium.
  • R 1 , R 2 , and R 5 to R 8 each independently, may represent hydrogen.
  • a each independently, represents an integer of 1 or 2; b and c, each independently, represent an integer of 1 to 4; and d represents an integer of 1 to 3.
  • R 1 and each of R 2 may be the same or different.
  • a 1 to A 11 , X 1 , X 2 , L 1 , Ar 1 and Ar 2 are as defined in formula 1 above.
  • the compound represented by formula 1 may be represented by any one of the following formulas 11 to 13.
  • a 1 to A 11 , R 3 , L 1 , Ar 1 and Ar 2 are as defined in formula 1 above.
  • the compound represented by formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.
  • the organic electroluminescent compound of the present disclosure may be prepared by a synthetic method known to one skilled in the art.
  • the organic electroluminescent compound of the present disclosure can be prepared by referring to the following reaction schemes, but is not limited thereto.
  • a 1 to A 11 , X 1 , X 2 , R 1 , R 2 , R 5 , L 1 , Ar 1 , and Ar 2 are each as defined in formulas 1 to 8.
  • the dopant that may be used in combination with the compound of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant.
  • the phosphorescent dopant is not particularly limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may include the compound represented by the following formula 101, but is not limited thereto.
  • L is selected from the following structures 1 and 2:
  • R 100 to R 103 and R 104 to R 107 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to an adjacent substituent to form a ring(s).
  • adjacent R 100 to R 103 may be linked to each other to form a ring, e.g., a substituted or unsubstituted, quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline or indenoquinoline ring, together with pyridine;
  • a ring e.g., a substituted or unsubstituted, quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline or indenoquinoline ring, together with pyridine;
  • R 104 to R 107 may be linked to an adjacent substituent to form a ring(s), e.g., a substituted or unsubstituted, naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine or benzothienopyridine ring, together with benzene;
  • a ring(s) e.g., a substituted or unsubstituted, naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine or benzothienopyridine ring, together with benzene;
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent to form a ring(s); and
  • s represents an integer of 1 to 3.
  • dopant The specific examples of the dopant are as follows, but are not limited thereto.
  • the compound represented by formula 1 of the present disclosure may be comprised in at least one layer consistituting an organic electroluminescent device, and for example, at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting 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 compound represented by formula 1 of the present disclosure is not limited thereto, but may be included in the light-emitting layer, and may be included in the light-emitting layer as a host material.
  • the organic electroluminescent materials of the present disclosure may comprise the compound represented by formula 1.
  • the material may be a light-emitting material.
  • the light-emitting material may consist of only the compound represented by formula 1, and may further comprise a conventional material(s) included in organic electroluminescent materials.
  • the organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
  • One of the first and second electrodes may be an anode, and the other may be a cathode.
  • 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 first electrode and the second electrode may each be formed with 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 both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the hole injection layer may be further doped with a p-dopant, and the electron injection layer may be further doped with an n-dopant.
  • the organic electroluminescent device of the present disclosure may comprise the compound represented by formula 1, and may further comprise a conventional material(s) included in organic electroluminescent devices.
  • the organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 of the present disclosure may exhibit a high luminous efficiency and/or long lifetime properties.
  • the present disclosure may provide a display system by using the compound represented by formula 1.
  • a display system e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars, or a lighting system, e.g., an outdoor or indoor lighting system, by using the compound of the present disclosure.
  • An OLED comprising the organic electroluminescent compound according to the present disclosure was produced, as follows: 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, ethanol and distilled water, 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 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 HT-2 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 having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: The compound described as a host material in Table 2 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 and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • An OLED was produced in the same manner as in Device Example 1, except that compound CBP was used as a host of the light-emitting layer.
  • the OLED comprising the compound according to the present disclosure as a host material has low driving voltage and/or high luminous efficiency and/or long lifetime as compared with an OLED comprising a conventional organic electroluminescent compound.
  • the organic electroluminescent compound of the present disclosure has a high-fused structure, so that it has a relatively high glass transition temperature (Tg) as compared with other organic electroluminescent compounds having similar molecular weights, and thus the compound of the present disclosure has good thermal stability.

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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 of the present disclosure having good thermal stability, it is possible to provide an organic electroluminescent device having lower driving voltage, higher luminous efficiency and/or longer lifetime properties as compared with a 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.
An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. An organic electroluminescent device was first developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
An organic electroluminescent device (OLED) changes electric energy into light by applying electricity to an organic luminous material, and commonly has a structure comprising an anode, a cathode, and an organic layer between the two electrodes. The organic layer of the OLED 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, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., as necessary. 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 (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on their functions. In the OLED, 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 an energy when the organic light-emitting compound returns to a ground state from the excited state.
The most important factor determining luminous efficiency of an OLED is light-emitting materials. The light-emitting materials are required to have the following features: high quantum efficiency, high mobility of an electron and a hole, and uniformity and stability of the formed light-emitting material layer. The light-emitting material is classified into blue, green, and red light-emitting materials according to the light-emitting color, and further includes yellow or orange light-emitting materials. In addition, the light-emitting material is classified into a host material and a dopant material in a functional aspect. Preferably, a host material as a solvent in a solid state and an energy transmitter should have high purity and a suitable molecular weight in order to be deposited under vacuum. Furthermore, a host material is required to have high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve a long lifetime, and easy formability of an amorphous thin film.
Recently, an urgent task is the development of an OLED having high efficiency and long lifetime. In particular, the development of highly excellent light-emitting material over conventional materials is urgently required, considering the EL properties necessary for medium- and large-sized OLED panels.
Meanwhile, U.S. Patent No. 6,706,423 (published on March 16, 2004) discloses a compound containing an indole as a light-emitting material, but the development for improving performances of an OLED is still required.
The objective of the present disclosure is to provide an organic electroluminescent compound having good thermal stability, and effective for producing an organic electroluminescent device having low driving voltage, high luminous efficiency and/or long lifetime properties.
A compound having a low glass transition temperature (Tg) may reduce the charge mobility in a thin film and deteriorate the performance of an OLED device. As a result of intensive studies, the present inventors have developed a novel organic electroluminescent compound having a planar main core, which can assist pi-pi stacking in a vacuum deposition layer to lead to rapid charge mobility, and having a high Tg in spite of its low molecular weight, which can provide excellent morphological stability. Specifically, the present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
Figure PCTKR2019010420-appb-I000001
wherein
A1 to A11, each independently, represent N or CR1;
X1 represents N, NR3 or CR4, X2 represents N or C; with the proviso that at least one of X1 and X2 contains N;
R1, R3, R4, Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more adjacent R1’s may be linked to each other to form a ring(s); where if a plurality of R1’s is present, each of R1 may be the same or different; and
L1, each independently, represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene.
The organic electroluminescent compound according to the present disclosure has good thermal stability, and in addition or alternatively, can provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifetime properties.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure, and is not meant in any way to restrict the scope of the disclosure.
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 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 (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
Herein, the term "(C1-C30)alkyl(ene)" is meant to be a linear or branched alkyl(ene) 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. The term "(C2-C30)alkenyl" is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term "(C2-C30)alkynyl" is meant to be 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, and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term "(C3-C30)cycloalkyl(ene)" is meant to be 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. The term "(3- to 7-membered)heterocycloalkyl" is meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term "(C6-C30)aryl(ene)" is meant to be 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 25, more preferably 6 to 18. The above aryl may be partially saturated, and may comprise a spiro structure. The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. More specifically, the aryl may include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a benzanthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a naphthacenyl group, a pyrenyl group, a 1-chrysenyl group, a 2-chrysenyl group, a 3-chrysenyl group, a 4-chrysenyl group, a 5-chrysenyl group, a 6-chrysenyl group, a benzo[c]phenanthryl group, a benzo[g]chrysenyl group, a 1-triphenylenyl group, a 2-triphenylenyl group, a 3-triphenylenyl group, a 4-triphenylenyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 9-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, an o-terphenyl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-quaterphenyl group, a 3-fluoranthenyl group, a 4-fluoranthenyl group, an 8-fluoranthenyl group, a 9-fluoranthenyl group, a benzofluoranthenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,3-xylyl group, a 3,4-xylyl group, a 2,5-xylyl group, a mesityl group, an o-cumenyl group, an m-cumenyl group, a p-cumenyl group, a p-tert-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 4'-methylbiphenylyl group, a 4"-tert-butyl-p-terphenyl-4-yl group, a 9,9-dimethyl-1-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, a 9,9-dimethyl-3-fluorenyl group, a 9,9-dimethyl-4-fluorenyl group, a 9,9-diphenyl-1-fluorenyl group, a 9,9-diphenyl-2-fluorenyl group, a 9,9-diphenyl-3-fluorenyl group, a 9,9-diphenyl-4-fluorenyl group, etc.
The term "(3- to 30-membered)heteroaryl(ene)" is meant to be an aryl group having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl 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); and may comprise a spiro structure. The above heteroaryl may include a monocyclic ring-type heteroaryl such as 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 such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. More specifically, the heteroaryl may include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 6-pyrimidinyl group, a 1,2,3-triazin-4-yl group, a 1,2,4-triazin-3-yl group, a 1,3,5-triazin-2-yl group, a 1-imidazolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 1-indolidinyl group, a 2-indolidinyl group, a 3-indolidinyl group, a 5-indolidinyl group, a 6-indolidinyl group, a 7-indolidinyl group, an 8-indolidinyl group, a 2-imidazopyridinyl group, a 3-imidazopyridinyl group, a 5-imidazopyridinyl group, a 6-imidazopyridinyl group, a 7-imidazopyridinyl group, an 8-imidazopyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinyl group, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a 9-carbazolyl group, an azacarbazolyl-1-yl group, an azacarbazolyl-2-yl group, an azacarbazolyl-3-yl group, an azacarbazolyl-4-yl group, an azacarbazolyl-5-yl group, an azacarbazolyl-6-yl group, an azacarbazolyl-7-yl group, an azacarbazolyl-8-yl group, an azacarbazolyl-9-yl group, a 1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a 2-tert-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-tert-butyl-1-indolyl group, a 4-tert-butyl-1-indolyl group, a 2-tert-butyl-3-indolyl group, a 4-tert-butyl-3-indolyl group, a 1-dibenzofuranyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, a 4-dibenzofuranyl group, a 1-dibenzothiophenyl group, a 2-dibenzothiophenyl group, a 3-dibenzothiophenyl group, a 4-dibenzothiophenyl group, a 1-silafluorenyl group, a 2-silafluorenyl group, a 3-silafluorenyl group, a 4-silafluorenyl group, a 1-germafluorenyl group, a 2-germafluorenyl group, a 3-germafluorenyl group, a 4-germafluorenyl group, etc. "Halogen" includes F, Cl, Br, and I.
In addition, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes, which represent the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called an ortho position. Meta indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is called a meta position. Para indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is called a para position.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e., a substituent. In the present disclosure, the substituents of the substituted (C1-C30)alkyl(ene), the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), 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; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituents, each independently, are at least one selected from the group consisting of a (C1-C20)alkyl; a (C6-C25)aryl and a (3- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, the substituents, each independently, are at least one selected from the group consisting of a (C1-C10)alkyl, a (C6-C18)aryl and a (5- to 20-membered)heteroaryl. For example, the substituents, each independently, may be at least one selected from the group consisting of a methyl, a phenyl, a naphthyl, a biphenyl, and a dibenzofuranyl.
In the formulas of the present disclosure, a ring formed by a linkage of adjacent substituents means that at least two adjacent substituents are linked to or fused with each other to form a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof; and preferably, a substituted or unsubstituted mono- or polycyclic (3- to 26-membered) alicyclic or aromatic ring, or the combination thereof. Also, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.
Herein, the heteroaryl(ene) and the heterocycloalkyl, each independently, may contain at least one heteroatom selected from B, N, O, S, Si, and P. Also, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, a halogen, a 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.
In formula 1, A1 to A11, each independently, represent N or CR1. According to one embodiment of the present disclosure, A1 to A11, each independently, represent CR1.
R1, each independently, represents hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more adjacent R1’s may be linked to each other to form a ring(s). If a plurality of R1’s is present, each of R1 may be the same or different. According to one embodiment of the present disclosure, R1, each independently, represents hydrogen, deuterium, an unsubstituted (C1-C20)alkyl, an unsubstituted (C6-C25)aryl, or an unsubstituted (5- to 25-membered)heteroaryl; or two or more adjacent R1’s may be linked to each other to form a ring(s). According to another embodiment of the present disclosure, R1, each independently, represents hydrogen, or two or more adjacent R1’s may be linked to each other to form a ring(s). The ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof; and preferably, an unsubstituted mono- or polycyclic (5- to 25-membered) alicyclic or aromatic ring, or the combination thereof. Also, the ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. For example, the ring may be a benzene ring, a pyridine ring, a benzofuran ring, or a benzothiophene ring, etc.
In formula 1, X1 represents N, NR3 or CR4, and X2 represents N or C; with the proviso that at least one of X1 and X2 contains N. Specifically, when X2 represents N, X1 represents N, NR3 or CR4, and when X2 represents C, X1 represents N or NR3. For example, when X2 represents N, X1 may represent N or CR4, and when X2 represents C, X1 may represent NR3. In formula 1,
Figure PCTKR2019010420-appb-I000002
represents a single bond or a double bond, respectively, depending on the substituent bonded. For example, when X2 represents N,
Figure PCTKR2019010420-appb-I000003
linked to X2 represents a single bond, and when X1 represents N,
Figure PCTKR2019010420-appb-I000004
linked to X1 represents a double bond.
R3 and R4, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a ring(s). According to one embodiment of the present disclosure, R3 and R4, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, R3 and R4, each independently, represent hydrogen, deuterium, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl. For example, R3, each independently, may represent a phenyl, and R4, each independently, may represent hydrogen.
In formula 1, Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. According to one embodiment of the present disclosure, Ar1 and Ar2, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- 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 of the present disclosure, Ar1, each independently, represents an unsubstituted (C6-C18)aryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s) and/or a (3- to 20-membered)heteroaryl(s); or a di(C6-C18)arylamino unsubstituted or substituted with a (C1-C6)alkyl(s). According to another embodiment of the present disclosure, Ar2, each independently, represents hydrogen, deuterium, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl. For example, Ar1, each independently, represents a phenyl; a biphenyl; a pyridyl unsubstituted or substituted with a phenyl(s); a pyrimidinyl unsubstituted or substituted with a phenyl(s); a triazinyl unsubstituted or substituted with at least one of a phenyl(s), a biphenyl(s), a naphthyl(s), and a dibenzofuranyl(s); a quinazolinyl substituted with a phenyl(s); a quinoxalinyl substituted with a phenyl(s); a carbazolyl; a dibenzofuranyl; a benzoquinazolinyl substituted with a phenyl(s); a benzoquinoxalinyl substituted with a phenyl(s); or a dimethylfluorenylphenylamino, etc. For example, Ar2, each independently, represents hydrogen, deuterium, a phenyl, or a pyridyl, etc.
In formula 1, L1, each independently, represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene. According to one embodiment of the present disclosure, L1, each independently, represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene. According to another embodiment of the present disclosure, L1, each independently, represents a single bond, an unsubstituted (C6-C18)arylene, or a (5- to 20-membered)heteroarylene unsubstituted or substituted with a (C6-C10)aryl(s). For example, L1, each independently, represents a single bond, a phenylene, a naphthylene, a biphenylene, a pyridylene, a pyrimidinylene substituted with a phenyl(s), a triazinylene substituted with a phenyl(s), a quinazolinylene, a quinoxalinylene, a benzoquinazolinylene, or a benzoquinoxalinylene, etc.
The compound represented by formula 1 may be represented by any one of the following formulas 2 to 8.
Figure PCTKR2019010420-appb-I000005
Figure PCTKR2019010420-appb-I000006
Figure PCTKR2019010420-appb-I000007
Figure PCTKR2019010420-appb-I000008
In formulas 2 to 4, Y1 represents NR5, O, S or CR6R7. According to one embodiment of the present disclosure, Y1 represents O or S.
In formulas 5 to 7, T1 to T4, each independently, represent CR8 or N.
In formulas 2 to 8, R1, R2, and R5 to R8, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. If a plurality of R1’s, a plurality of R2’s, and a plurality of R8’s, each independently, are present, each of R1, each of R2, and each of R8 may be the same or different. According to one embodiment of the present disclosure, R1, R2, and R5 to R8, each independently, represent hydrogen, deuterium, an unsubstituted (C1-C20)alkyl, an unsubstituted (C6-C25)aryl, or an unsubstituted (3- to 25-membered)heteroaryl. According to one embodiment of the present disclosure, R1, R2, and R5 to R8, each independently, represent hydrogen or deuterium. For example, R1, R2, and R5 to R8, each independently, may represent hydrogen.
In formulas 2 to 8, a, each independently, represents an integer of 1 or 2; b and c, each independently, represent an integer of 1 to 4; and d represents an integer of 1 to 3. Each of R1 and each of R2 may be the same or different.
In formulas 2 to 8, A1 to A11, X1, X2, L1, Ar1 and Ar2 are as defined in formula 1 above.
The compound represented by formula 1 may be represented by any one of the following formulas 11 to 13.
Figure PCTKR2019010420-appb-I000009
Figure PCTKR2019010420-appb-I000010
In formulas 11 to 13, A1 to A11, R3, L1, Ar1 and Ar2 are as defined in formula 1 above.
The compound represented by formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.
Figure PCTKR2019010420-appb-I000011
Figure PCTKR2019010420-appb-I000012
Figure PCTKR2019010420-appb-I000013
Figure PCTKR2019010420-appb-I000014
Figure PCTKR2019010420-appb-I000015
Figure PCTKR2019010420-appb-I000016
Figure PCTKR2019010420-appb-I000017
Figure PCTKR2019010420-appb-I000018
Figure PCTKR2019010420-appb-I000019
Figure PCTKR2019010420-appb-I000020
Figure PCTKR2019010420-appb-I000021
Figure PCTKR2019010420-appb-I000022
Figure PCTKR2019010420-appb-I000023
Figure PCTKR2019010420-appb-I000024
Figure PCTKR2019010420-appb-I000025
Figure PCTKR2019010420-appb-I000026
Figure PCTKR2019010420-appb-I000027
Figure PCTKR2019010420-appb-I000028
Figure PCTKR2019010420-appb-I000029
Figure PCTKR2019010420-appb-I000030
The organic electroluminescent compound of the present disclosure may be prepared by a synthetic method known to one skilled in the art. For example, the organic electroluminescent compound of the present disclosure can be prepared by referring to the following reaction schemes, but is not limited thereto.
[Reaction Scheme 1]
Figure PCTKR2019010420-appb-I000031
Figure PCTKR2019010420-appb-I000032
[Reaction Scheme 2]
Figure PCTKR2019010420-appb-I000033
Figure PCTKR2019010420-appb-I000034
Figure PCTKR2019010420-appb-I000035
[Reaction Scheme 3]
Figure PCTKR2019010420-appb-I000036
Figure PCTKR2019010420-appb-I000037
Figure PCTKR2019010420-appb-I000038
Figure PCTKR2019010420-appb-I000039
[Reaction Scheme 4]
Figure PCTKR2019010420-appb-I000040
Figure PCTKR2019010420-appb-I000041
[Reaction Scheme 5]
Figure PCTKR2019010420-appb-I000042
Figure PCTKR2019010420-appb-I000043
Figure PCTKR2019010420-appb-I000044
[Reaction Scheme 6]
Figure PCTKR2019010420-appb-I000045
Figure PCTKR2019010420-appb-I000046
[Reaction Scheme 7]
Figure PCTKR2019010420-appb-I000047
Figure PCTKR2019010420-appb-I000048
Figure PCTKR2019010420-appb-I000049
[Reaction Scheme 8]
Figure PCTKR2019010420-appb-I000050
Figure PCTKR2019010420-appb-I000051
Figure PCTKR2019010420-appb-I000052
[Reaction Scheme 9]
Figure PCTKR2019010420-appb-I000053
Figure PCTKR2019010420-appb-I000054
Figure PCTKR2019010420-appb-I000055
[Reaction Scheme 10]
Figure PCTKR2019010420-appb-I000056
Figure PCTKR2019010420-appb-I000057
Figure PCTKR2019010420-appb-I000058
In reaction schemes 1 to 10, A1 to A11, X1, X2, R1, R2, R5, L1, Ar1, and Ar2 are each as defined in formulas 1 to 8.
Although illustrative synthesis examples of the compound represented by formula 1 were described above, one skilled in the art will be able to readily understand that all of them are based on a Buchwald-Hartwig cross-coupling reaction, an N-arylation reaction, a H-mont-mediated etherification reaction, a Miyaura borylation reaction, a Suzuki cross-coupling reaction, an Intramolecular acid-induced cyclization reaction, a Pd(II)-catalyzed oxidative cyclization reaction, a Grignard reaction, a Heck reaction, a Cyclic Dehydration reaction, an SN1 substitution reaction, an SN2 substitution reaction, a Phosphine-mediated reductive cyclization reaction, a Vilsmeier-Haack reaction, and etc., and the above reactions proceed even when substituents, which are defined in formula 1 above but are not specified in the specific synthesis examples, are bonded.
The dopant that may be used in combination with the compound of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant is not particularly limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The dopant comprised in the organic electroluminescent device of the present disclosure may include the compound represented by the following formula 101, but is not limited thereto.
Figure PCTKR2019010420-appb-I000059
In formula 101, L is selected from the following structures 1 and 2:
Figure PCTKR2019010420-appb-I000060
R100 to R103 and R104 to R107, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to an adjacent substituent to form a ring(s). Specifically, adjacent R100 to R103 may be linked to each other to form a ring, e.g., a substituted or unsubstituted, quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline or indenoquinoline ring, together with pyridine;
R104 to R107 may be linked to an adjacent substituent to form a ring(s), e.g., a substituted or unsubstituted, naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine or benzothienopyridine ring, together with benzene;
R201 to R211, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent to form a ring(s); and
s represents an integer of 1 to 3.
The specific examples of the dopant are as follows, but are not limited thereto.
Figure PCTKR2019010420-appb-I000061
Figure PCTKR2019010420-appb-I000062
Figure PCTKR2019010420-appb-I000063
Figure PCTKR2019010420-appb-I000064
Figure PCTKR2019010420-appb-I000065
Figure PCTKR2019010420-appb-I000066
Figure PCTKR2019010420-appb-I000067
Figure PCTKR2019010420-appb-I000068
Figure PCTKR2019010420-appb-I000069
Figure PCTKR2019010420-appb-I000070
Figure PCTKR2019010420-appb-I000071
Figure PCTKR2019010420-appb-I000072
Figure PCTKR2019010420-appb-I000073
Figure PCTKR2019010420-appb-I000074
Figure PCTKR2019010420-appb-I000075
Figure PCTKR2019010420-appb-I000076
Figure PCTKR2019010420-appb-I000077
Figure PCTKR2019010420-appb-I000078
Figure PCTKR2019010420-appb-I000079
Figure PCTKR2019010420-appb-I000080
Figure PCTKR2019010420-appb-I000081
Figure PCTKR2019010420-appb-I000082
The compound represented by formula 1 of the present disclosure may be comprised in at least one layer consistituting an organic electroluminescent device, and for example, at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting 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 compound represented by formula 1 of the present disclosure is not limited thereto, but may be included in the light-emitting layer, and may be included in the light-emitting layer as a host material.
The organic electroluminescent materials of the present disclosure, for example, at least one 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 layer, may comprise the compound represented by formula 1. The material may be a light-emitting material. The light-emitting material may consist of only the compound represented by formula 1, and may further comprise a conventional material(s) included in organic electroluminescent materials.
The organic electroluminescent device according to the present disclosure comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes. One of the first and second electrodes may be an anode, and the other may be a cathode. 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 first electrode and the second electrode may each be formed with 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 both-sides emission type according to the kinds of the material forming the first electrode and the second electrode. In addition, the hole injection layer may be further doped with a p-dopant, and the electron injection layer may be further doped with an n-dopant.
The organic electroluminescent device of the present disclosure may comprise the compound represented by formula 1, and may further comprise a conventional material(s) included in organic electroluminescent devices. The organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 of the present disclosure may exhibit a high luminous efficiency and/or long lifetime properties.
The present disclosure may provide a display system by using the compound represented by formula 1. In addition, it is possible to produce a display system or a lighting system by using the compound of the present disclosure. Specifically, it is possible to produce a display system, e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars, or a lighting system, e.g., an outdoor or indoor lighting system, by using the compound of the present disclosure.
Hereinafter, the preparation method of the compound according to the present disclosure and the properties thereof will be explained in detail. However, the present disclosure is not limited to the following examples.
Example 1: Preparation of compound C-15
Figure PCTKR2019010420-appb-I000083
Figure PCTKR2019010420-appb-I000084
Synthesis of compound 1-1
In a reaction vessel, 100 g of 1-fluoro-2-nitrobenzene (0.709 mol), 90.4 g of 2-chloroaniline (0.709 mol), 59.7 g of potassium hydroxide (1.063 mol), and 800 mL of dimethylsulfoxide were added, and the mixture was stirred at 150℃ for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 62 g of compound 1-1 (yield: 35%).
Synthesis of compound 1-2
In a reaction vessel, 72 g of compound 1-1 (0.290 mol), 326.6 g of Tin(II) chloride dehydrate (1.448 mol), and 1400 mL of ethanol were added, and the mixture was stirred at 70℃ for 2 hours. After completion of the reaction, the reaction mixture was slowly cooled to 0℃ and then neutralized with an aqueous sodium hydroxide solution. After neutralization, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 53 g of compound 1-2 (yield: 63%).
Synthesis of compound 2-1
In a reaction vessel, 60 g of oxindol (0.450 mol), 105 mL of N,N-dimethylformamide (1.350 mol), 126 mL of phosphorus oxychloride (1.350 mol), and 1200 mL of 1,2-dichloroethene were added, and the mixture was stirred at 50℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then neutralized with an aqueous potassium carbonate solution. After neutralization, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 35 g of compound 2-1 (yield: 43%).
Synthesis of compound 2-2
In a reaction vessel, 32.5 g of compound 2-1 (0.181 mol), 33.1 g of phenylboronic acid (0.271 mol), 10.5 g of tetrakis(triphenylphosphine)palladium(0) (0.009 mol), 48 g of potassium carbonate (0.452 mol), 880 mL of toluene, 220 mL of ethanol, and 220 mL of distilled water were added, and the mixture was stirred at 130℃ for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 38.3 g of compound 2-2 (yield: 95%).
Synthesis of compound 3-1
In a reaction vessel, 20.7 g of compound 1-2 (95.0 mmol), 21 g of compound 2-2 (95.0 mmol), 21.7 g of sodium metabisulfite (114.0 mmol), and 320 mL of N,N-dimethylformamide were added, and the mixture was stirred at 180℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 19.5 g of compound 3-1 (yield: 40%).
Synthesis of compound 3-2
In a reaction vessel, 19 g of compound 3-1 (45.2 mmol), 1.0 g of palladium(II) acetate (4.52 mmol), 3.3 g of tricyclohexylphosphine tetrafluoroborate (9.04 mmol), 44.2 g of cesium carbonate (135.6 mmol), and 230 mL of N,N-dimethylacetamide were added, and the mixture was stirred at 130℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 3.5 g of compound 3-2 (yield: 20%).
Synthesis of compound C-15
In a reaction vessel, 2.7 g of compound 3-2 (7.0 mmol), 1.7 g of 2-chloro-4-phenylquinazoline (7.0 mmol), 0.32 g of tris(dibenzylideneacetone)dipalladium(0) (0.35 mmol), 0.32 mL of tri-tert-butylphosphine (0.70 mmol), 1.7 g of sodium tert-butoxide (18.0 mmol), and 135 mL of o-xylene were added, and the mixture was stirred at 120℃ for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 2.7 g of compound C-15 (yield: 65%).
The physical properties of the synthesized compound are summarized in Table 1 below.
Figure PCTKR2019010420-appb-I000085
H-NMR data of compound C-15
Figure PCTKR2019010420-appb-I000086
Hereinafter, the properties of an OLED comprising the compound according to the present disclosure will be explained. However, the following examples merely illustrate the properties of an OLED according to the present disclosure in detail, and the present disclosure is not limited to the following examples.
Device Example 1: Producing an OLED comprising the compound according
to the present disclosure
An OLED comprising the organic electroluminescent compound according to the present disclosure was produced, as follows: 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, ethanol and distilled water, 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 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, 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 HT-2 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 having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was formed thereon as follows: The compound described as a host material in Table 2 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 and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.
Comparative Example 1: Producing an OLED comprising a compound not
according to the present disclosure
An OLED was produced in the same manner as in Device Example 1, except that compound CBP was used as a host of the light-emitting layer.
The results of the driving voltage and luminous efficiency at a luminance of 1,000 nit, and the time taken to reduce from the initial luminance of 100% to a luminance of 95% at a constant current in a luminance of 5,000 nit (lifetime: T95) of the OLEDs produced in the Device Example and the Comparative Example, are shown in Table 2 below.
Figure PCTKR2019010420-appb-I000087
From Table 2 above, it can be confirmed that the OLED comprising the compound according to the present disclosure as a host material has low driving voltage and/or high luminous efficiency and/or long lifetime as compared with an OLED comprising a conventional organic electroluminescent compound. In addition, it can be recognized that the organic electroluminescent compound of the present disclosure has a high-fused structure, so that it has a relatively high glass transition temperature (Tg) as compared with other organic electroluminescent compounds having similar molecular weights, and thus the compound of the present disclosure has good thermal stability.
The compounds used in the Device Example and the Comparative Example are shown in Table 3 below.
Figure PCTKR2019010420-appb-I000088
Figure PCTKR2019010420-appb-I000089

Claims (8)

  1. An organic electroluminescent compound represented by the following formula 1:
    Figure PCTKR2019010420-appb-I000090
    wherein
    A1 to A11, each independently, represent N or CR1;
    X1 represents N, NR3 or CR4, X2 represents N or C; with the proviso that at least one of X1 and X2 contains N;
    R1, R3, R4, Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more adjacent R1’s may be linked to each other to form a ring(s); where if a plurality of R1’s is present, each of R1 may be the same or different; and
    L1, each independently, represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene.
  2. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted (C1-C30)alkyl(ene), the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), 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; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
  3. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 2 to 8:
    Figure PCTKR2019010420-appb-I000091
    Figure PCTKR2019010420-appb-I000092
    Figure PCTKR2019010420-appb-I000093
    Figure PCTKR2019010420-appb-I000094
    wherein,
    Y1 represents NR5, O, S or CR6R7;
    T1 to T4, each independently, represent CR8 or N;
    R1, R2, and R5 to R8, each independently, represent hydrogen, deuterium, a halogen, a 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, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
    a, each independently, represents an integer of 1 or 2; b and c, each independently, represent an integer of 1 to 4; d represents an integer of 1 to 3;
    where if a plurality of R1’s, a plurality of R2’s, and a plurality of R8’s, each independently, are present, each of R1, each of R2, and each of R8 may be the same or different; and
    A1 to A11, X1, X2, L1, Ar1 and Ar2 are as defined in claim 1.
  4. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 11 to 13:
    Figure PCTKR2019010420-appb-I000095
    Figure PCTKR2019010420-appb-I000096
    wherein, A1 to A11, R3, L1, Ar1 and Ar2 are as defined in claim 1.
  5. The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula 1 is any one selected from the group consisting of the following compounds:
    Figure PCTKR2019010420-appb-I000097
    Figure PCTKR2019010420-appb-I000098
    Figure PCTKR2019010420-appb-I000099
    Figure PCTKR2019010420-appb-I000100
    Figure PCTKR2019010420-appb-I000101
    Figure PCTKR2019010420-appb-I000102
    Figure PCTKR2019010420-appb-I000103
    Figure PCTKR2019010420-appb-I000104
    Figure PCTKR2019010420-appb-I000105
    Figure PCTKR2019010420-appb-I000106
    Figure PCTKR2019010420-appb-I000107
    Figure PCTKR2019010420-appb-I000108
    Figure PCTKR2019010420-appb-I000109
    Figure PCTKR2019010420-appb-I000110
    Figure PCTKR2019010420-appb-I000111
    Figure PCTKR2019010420-appb-I000112
    Figure PCTKR2019010420-appb-I000113
    Figure PCTKR2019010420-appb-I000114
    Figure PCTKR2019010420-appb-I000115
    Figure PCTKR2019010420-appb-I000116
  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 comprised as a host material.
PCT/KR2019/010420 2018-09-14 2019-08-16 Organic electroluminescent compound and organic electroluminescent device comprising the same WO2020054989A1 (en)

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