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WO2020226280A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2020226280A1
WO2020226280A1 PCT/KR2020/004051 KR2020004051W WO2020226280A1 WO 2020226280 A1 WO2020226280 A1 WO 2020226280A1 KR 2020004051 W KR2020004051 W KR 2020004051W WO 2020226280 A1 WO2020226280 A1 WO 2020226280A1
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group
formula
divalent
substituted
layer
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Korean (ko)
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허동욱
홍성길
허정오
차용범
이재탁
양정훈
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers

Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Unexamined Patent Publication 10-2013-0135162
  • the present specification is to provide a heterocyclic compound and an organic light emitting device including the same.
  • L1 is a direct bond; A substituted or unsubstituted divalent to tetravalent phenyl group; A substituted or unsubstituted divalent to tetravalent biphenyl group; Or a substituted or unsubstituted divalent to tetravalent terphenyl group,
  • L2 is a divalent to tetravalent phenyl group; Biphenyl group of divalent to tetravalent; Or a divalent to tetravalent terphenyl group,
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted divalent to tetravalent aryl group,
  • Ar1 is a divalent group represented by the following formula A1,
  • n 0 or 1
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r2 and r4 are the same as or different from each other and are each independently an integer of 0 to 4,
  • a1, a2, b1 and b2 are the same as or different from each other, and each independently an integer of 1 to 3,
  • R2 is the same as or different from each other
  • R4 is the same as or different from each other
  • X1 and X2 are each hydrogen, directly connected to each other, or connected through -O- or -S-,
  • any one of Q1 to Q16 is connected to L3 of Chemical Formula 2, the other is connected to L4 of Chemical Formula 2, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Formula 1 or 2 It provides a light emitting device.
  • the compound according to the exemplary embodiment of the present specification is used in an organic light-emitting device, so that a driving voltage of the organic light-emitting device may be lowered and light efficiency may be improved. In addition, it is possible to improve the life characteristics of the device by the thermal stability of the compound.
  • 1 and 2 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • the compound represented by Formula 1 at least one cyano group is connected to the end of the core structure in which quinazoline is connected to phenylene or naphthylene.
  • the compound represented by Formula 2 has one or more cyano groups connected to the end of the core structure in which quinazoline is connected to a polycyclic spiro structure or diphenylfluorene.
  • the compound of Formula 1 or 2 is used as an electron transport layer or an electron injection layer. When used as a material, the long life characteristics of the organic light-emitting device are improved due to the increase of the dipole moment in the molecule.
  • a cyano group is connected to the end of the structure, so that the high efficiency and low voltage characteristics are improved compared to the compounds having different substitution positions of the cyano group.
  • the compound represented by Formula 1 does not contain a naphthalene linker in L1 and L2, but compared to a compound containing a naphthalene linker, high efficiency and low voltage characteristics are improved.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Alkyl group; Aryl group; And substituted with one or two or more substituents selected from the group consisting of a heteroaryl group containing one or more heteroatoms other than carbon, or substituted with a substituent to which two or more substituents are connected, or not having any substituents Means that.
  • substituents when two or more substituents are connected, it means that hydrogen of any one substituent is connected with another substituent.
  • an isopropyl group and a phenyl group are connected or It may be a substituent of.
  • connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are Includes connections.
  • two phenyl groups and isopropyl groups are connected or It may be a substituent of. The same applies to those in which four or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, o
  • an aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative.
  • an aromatic hydrocarbon refers to a compound in which pi electrons are completely conjugated and includes a planar ring
  • a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon.
  • the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other.
  • the aryl group is not particularly limited, but includes 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the substituted fluorenyl group when the fluorenyl group may be substituted, includes all compounds in which the substituents of the pentagonal rings of fluorene are spied to each other to form an aromatic hydrocarbon ring.
  • the substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited thereto.
  • the heterocyclic group is an atom other than carbon and includes one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, and S.
  • the number of carbon atoms is not particularly limited, the number of carbon atoms is 2 to 50; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13.
  • heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazino-pyrazine group, isoquinoline group, indole group, carbazole group, benzoxa Sol group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxadiazole group,
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic, and may be selected from examples of the heterocyclic group.
  • the heteroaryl group refers to a monovalent aromatic heterocycle.
  • the aromatic heterocycle refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, and refers to a group including at least one of O, N, and S in the ring as a hetero atom.
  • the aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring.
  • the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms are connected to each other. 2 to 50 carbon atoms of the heteroaryl group; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13.
  • L1 is a direct bond; A substituted or unsubstituted divalent to tetravalent phenyl group; A substituted or unsubstituted divalent to tetravalent biphenyl group; Or a substituted or unsubstituted divalent to tetravalent terphenyl group.
  • L1 is a direct bond; A divalent to tetravalent phenyl group unsubstituted or substituted with a cyano group or an alkyl group; A divalent to tetravalent biphenyl group unsubstituted or substituted with a cyano group or an alkyl group; Or a cyano group or a divalent to tetravalent terphenyl group unsubstituted or substituted with an alkyl group.
  • L1 is a direct bond; A divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group.
  • L1 is a direct bond; A divalent to trivalent phenyl group; Or a biphenyl group of divalent to trivalent.
  • L1 is a direct bond; Divalent phenyl group; Divalent biphenyl group; Or a divalent terphenyl group.
  • L1 is a trivalent phenyl group.
  • L2 is an unsubstituted divalent to tetravalent phenyl group; Unsubstituted divalent to tetravalent biphenyl group; Or an unsubstituted divalent to tetravalent terphenyl group.
  • L2 is a divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group.
  • L2 is a divalent to trivalent phenyl group; Or a biphenyl group of divalent to trivalent.
  • L2 is a divalent phenyl group; Divalent biphenyl group; Or a divalent terphenyl group.
  • L2 is a trivalent phenyl group; Trivalent biphenyl group; Or a trivalent terphenyl group.
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted divalent to tetravalent aryl group.
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted divalent to tetravalent aryl group having 6 to 30 carbon atoms.
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a divalent to trivalent aryl group having 6 to 20 carbon atoms.
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted divalent to tetravalent phenyl group; A substituted or unsubstituted divalent to tetravalent biphenyl group; A substituted or unsubstituted divalent to tetravalent terphenyl group; A substituted or unsubstituted divalent to tetravalent naphthyl group; A substituted or unsubstituted divalent to tetravalent fluorenyl group; A substituted or unsubstituted divalent to tetravalent phenanthrenyl group; A substituted or unsubstituted divalent to tetravalent anthracenyl group; A substituted or unsubstituted divalent to tetravalent pyrenyl group; Or a substituted or unsubstituted divalent to tetravalent ch
  • L3 is a direct bond; A divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group.
  • L3 is a direct bond; A divalent to trivalent phenyl group; Or a biphenyl group of divalent to trivalent.
  • L3 is a direct bond; Divalent phenyl group; Divalent biphenyl group; Or a divalent terphenyl group.
  • L3 is a trivalent phenyl group.
  • L4 is a direct bond; A divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group.
  • L4 is a direct bond; A divalent to trivalent phenyl group; Or a biphenyl group of divalent to trivalent.
  • L4 is a direct bond; Divalent phenyl group; Divalent biphenyl group; Or a divalent terphenyl group.
  • L4 is a direct bond; Trivalent phenyl group; Trivalent biphenyl group; Or a trivalent terphenyl group.
  • L1, L3, and L4 are the same as or different from each other, and each independently a direct bond or selected from the following structures, and L2 is selected from the following structures.
  • L1, L3, and L4 are the same as or different from each other, and each independently a direct bond or selected from the following structures, and L2 is selected from the following structures.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C5 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R1 is an aryl group having 6 to 20 carbon atoms.
  • R1 is an aryl group having 6 to 20 carbon atoms
  • R2 is hydrogen or deuterium
  • R1 is a phenyl group; Biphenyl group; Or a naphthyl group.
  • R3 is an aryl group having 6 to 20 carbon atoms.
  • R3 is an aryl group having 6 to 20 carbon atoms
  • R4 is hydrogen or deuterium
  • R3 is a phenyl group; Biphenyl group; Or a naphthyl group.
  • R2 is each hydrogen or deuterium.
  • R4 is each hydrogen or deuterium.
  • r2 and r4 are the same as or different from each other and are each independently an integer of 0 to 4, when r2 is 2 or more, R2 is the same or different from each other, and when r4 is 2 or more, R4 is the same as each other. Or different.
  • r2 is 0.
  • r4 is 0.
  • Chemical Formula 1 is represented by the following Chemical Formula 101 or 102.
  • L1, L2, R1, R2, r2, m, a1, and b1 are as defined in Formula 1.
  • Chemical Formula 2 is represented by the following Chemical Formula 201 or 202.
  • L3, L4, R3, R4, r4, Ar1, a2, and b2 are as defined in Chemical Formula 2.
  • m is 0 or 1.
  • Ar1 is a divalent group represented by the following Chemical Formula A1.
  • X1 and X2 are each hydrogen, directly connected to each other, or connected through -O- or -S-,
  • any one of Q1 to Q16 is connected to L3 of Chemical Formula 2, the other is connected to L4 of Chemical Formula 2, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 is a divalent group represented by any one of the following Formulas A11 to A14.
  • the substituents not connected to L3 or L4 in Formula 2 of Q1 to Q16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the substituents not connected to L3 or L4 in Formula 2 of Q1 to Q16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted C 1 to C 6 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • the substituent not connected to L3 or L4 in Formula 2 is hydrogen.
  • Ar1 is a divalent group selected from the following structures.
  • the structure is deuterium; Cyano group; Alkyl group; Aryl group; Or substituted or unsubstituted with a heteroaryl group,
  • Ar1 is a divalent group selected from the following structures.
  • the structure is deuterium; Cyano group; Alkyl group; Aryl group; Or substituted or unsubstituted with a heteroaryl group,
  • a1, a2, b1, and b2 are the same as or different from each other, and are each independently an integer of 1 to 3.
  • a1 is 1 or 2.
  • a1 is 1.
  • a1 is 2.
  • a2 is 1 or 2.
  • a2 is 1.
  • a2 is 2.
  • Chemical Formula 1 is represented by Chemical Formula 103 or 104 below.
  • R1, R2, r2, m, L2 and b1 are as defined in Formula 1,
  • L11 is a direct bond; A substituted or unsubstituted divalent phenyl group; Or a substituted or unsubstituted divalent biphenyl group,
  • R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r12 is an integer of 0 to 4, and when r12 is 2 or more, R12 is the same as or different from each other.
  • R11 is an aryl group having 6 to 20 carbon atoms.
  • R11 is a phenyl group.
  • R12 is hydrogen
  • r12 is 0.
  • L11 is a direct bond.
  • b1 is 1 or 2.
  • b1 is 1.
  • b1 is 2.
  • b2 is 1 or 2.
  • b2 is 1.
  • b2 is 2.
  • -L2-(CN) b1 of Formula 1 or -L4-(CN) b2 of Formula 2 is selected from the following structures.
  • L21 is a direct bond; Divalent phenyl group; Or a divalent biphenyl group.
  • L21 is a direct bond; Or a divalent phenyl group.
  • L21 is a direct bond.
  • -L2-(CN) b1 of Formula 1 or -L4-(CN) b2 of Formula 2 is selected from the following structures.
  • L1 is a direct bond; A divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group,
  • L2 is a divalent to trivalent phenyl group; Biphenyl group of divalent to trivalent; Or a divalent to trivalent terphenyl group,
  • L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a divalent to trivalent aryl group having 6 to 20 carbon atoms,
  • R1 is an aryl group having 6 to 20 carbon atoms
  • R2 is hydrogen or deuterium
  • R3 is an aryl group having 6 to 20 carbon atoms
  • R4 is hydrogen or deuterium
  • the substituent not connected to L3 or L4 in Formula 2 is hydrogen.
  • the heterocyclic compound represented by Formula 1 is any one selected from the following compounds.
  • the heterocyclic compound represented by Formula 2 is any one selected from the following compounds.
  • the compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. If necessary, a substituent may be added or removed, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, and the like can be changed based on techniques known in the art.
  • the compound represented by Formula 1 may have a core structure as shown in Formula 1 below
  • the compound represented by Formula 2 may have a core structure as shown in Formula 2 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. Substituents may be combined as shown in Formulas 1 and 2 below, but are not limited thereto.
  • L1, L2, R1, R2, r2, m, a1 and b1 are as defined in Chemical Formula 1
  • L3, L4, Ar1, R3, R4, r4, The definitions of a2 and b2 are as defined in Chemical Formula 2.
  • X is halogen and more preferably bromo or chloro.
  • the reaction is a Suzuki coupling reaction, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction may be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.
  • the present specification provides an organic light-emitting device including the above-described compound.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
  • the'layer' is meant to be compatible with the'film' mainly used in the present technical field, and means a coating covering a desired area.
  • the size of the'layer' is not limited, and each'layer' may be the same or different in size. In one embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional region, and may be as small as a single sub-pixel.
  • the meaning that a specific A material is included in the B layer means that i) one or more A material is included in one layer B, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B Includes all those included in one or more of the floors.
  • the meaning that a specific A material is included in the C layer or the D layer means i) is included in one or more of the C layers, ii) is included in one or more of the D layers, iii ) It means both included in one or more layers C and one or more layers D.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes an emission layer, and the emission layer includes a heterocyclic compound represented by Formula 1 above.
  • the organic material layer includes an electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons, or a hole blocking layer, and simultaneously performing the electron injection layer, the electron transport layer, and electron injection and transport.
  • the layer or hole blocking layer includes a heterocyclic compound represented by Formula 1 above.
  • the electron injection layer, the electron transport layer, the layer for simultaneously injecting and transporting electrons or the hole blocking layer includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals. .
  • the organic alkali metal compound or the organic alkaline earth metal compound When used as an n-type dopant, stability against holes from the light emitting layer can be secured, thereby improving the life of the organic light emitting device.
  • the electron mobility of the electron transport layer may be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the emission layer, thereby increasing luminous efficiency.
  • LiQ is more preferable as the n-type dopant used in the electron transport layer in the present specification.
  • the electron transport layer may include the heterocyclic compound represented by Formula 1 and the n-type dopant in a weight ratio of 1:9 to 9:1.
  • the heterocyclic compound of Formula 1 and the n-type dopant may be included in a ratio of 2:8 to 8:2, more preferably 3:7 to 7:3.
  • the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; An emission layer provided between the first electrode and the second electrode; And one or more organic material layers provided between the emission layer and the first electrode, or between the emission layer and the second electrode.
  • the at least one organic material layer is a hole injection layer and a hole transport layer. It further includes at least one layer selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the second electrode is a cathode, and the second electrode is an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • 1 and 2 illustrate an organic light-emitting device, but are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which an anode 102, an emission layer 106, and a cathode 108 are sequentially stacked on a substrate 101.
  • the compound represented by Formula 1 is included in the emission layer.
  • an anode 102 an anode 102, a hole injection layer 103, a first hole transport layer 104, a second hole transport layer 105, a light emitting layer 106, an electron injection and transport layer 107 and a cathode on the substrate 101.
  • the structure of an organic light emitting device in which (108) is sequentially stacked is illustrated.
  • the compound represented by Formula 1 is included in the electron injection and transport layer 107.
  • the organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that the emission layer includes the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form the anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • Metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There may be a multilayered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • an anthracene derivative substituted with deuterium may be used as a host material for the emission layer.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamine group.
  • the substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Further, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the hole transport layer may have a multilayer structure. For example, it may include a first hole transport layer and a second hole transport layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is preferable, and a material having high mobility for electrons is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material, as used according to the prior art.
  • suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron-injection material is excellent in the ability to transport electrons, and has an electron-receiving effect from the second electrode and an excellent electron-injection effect on the light-emitting layer or the light-emitting material. In addition, a material that prevents the excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • 8-hydroxyquinolinato lithium bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • a compound represented by Formula E2 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used as in the above reaction formula.
  • a compound represented by Formula E3 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E4 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E5 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E6 was prepared in the same manner as in the manufacturing method of E1 in Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E7 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E8 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E9 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E10 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E11 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E12 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E13 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a compound represented by Formula E14 was prepared in the same manner as in the manufacturing method of E1 of Preparation Example 1, except that each starting material was used in the above reaction formula.
  • a compound represented by Formula E15 was prepared in the same manner as in the manufacturing method of E1 in Preparation Example 1, except that each starting material was used in the above reaction scheme.
  • a glass substrate coated with a thin film of 1000 ⁇ of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • the following HAT compound 50 ⁇ and the following HT-A compound 60 ⁇ were sequentially vacuum-deposited on the hole injection layer to form a first hole transport layer and a second hole transport layer.
  • the following BH compound and BD compound with a film thickness of 200 ⁇ were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to form a light emitting layer.
  • the compound E1 of Preparation Example 1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 10 ⁇ and aluminum in a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec, the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec, and the deposition rate of aluminum was 2 ⁇ /sec, and the vacuum degree during deposition was 1 ⁇ 10. Maintaining -7 to 5 ⁇ 10 -5 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds E2 to E15 shown in Table 1 below were used instead of compound E1, respectively.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds ET-A to ET-J shown in Table 1 below were used instead of Compound E1 of Preparation Example 1.
  • Example 1 (E1) 4.44 5.00 (0.142, 0.096) 201
  • Example 2 (E2) 4.50 5.13 (0.142, 0.096) 184
  • Example 3 (E3) 4.45 5.10 (0.142, 0.096) 190
  • Example 4 (E4) 4.42 5.30 (0.142, 0.096) 211
  • Example 5 (E5) 4.60 4.87 (0.142, 0.096) 293
  • Example 6 (E6) 4.34 5.18 (0.142, 0.097) 176
  • Example 7 (E7) 4.49 5.03 (0.142, 0.096) 220
  • Example 8 (E8) 4.28 5.40 (0.142, 0.099) 202
  • Example 9 (E9) 4.33 5.21 (0.142, 0.096) 200
  • Example 10 (E10) 4.61 4.95 (0.142, 0.099) 244
  • Example 10 (E10) 4.61 4.95 (0.142, 0.099) 244
  • Example 10 (E10) 4.61 4.95 (0.142, 0.099) 244
  • Example 10 (
  • the compound represented by Formula 1 or 2 according to the present invention may be used in an organic material layer capable of simultaneously injecting electrons and transporting electrons in an organic light-emitting device.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1, et un dispositif électroluminescent organique le comprenant.
PCT/KR2020/004051 2019-05-03 2020-03-25 Composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2020226280A1 (fr)

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