WO2015152650A1 - 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2015152650A1
WO2015152650A1 PCT/KR2015/003291 KR2015003291W WO2015152650A1 WO 2015152650 A1 WO2015152650 A1 WO 2015152650A1 KR 2015003291 W KR2015003291 W KR 2015003291W WO 2015152650 A1 WO2015152650 A1 WO 2015152650A1
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group
substituted
unsubstituted
aryl
alkyl
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PCT/KR2015/003291
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English (en)
French (fr)
Korean (ko)
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장분재
이동훈
허동욱
한미연
강민영
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주식회사 엘지화학
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Priority claimed from KR1020150017929A external-priority patent/KR20150115622A/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201580017744.7A priority Critical patent/CN106132937B/zh
Priority to CN201910006887.8A priority patent/CN109970670B/zh
Priority to US15/301,607 priority patent/US10510963B2/en
Priority to CN201910006879.3A priority patent/CN109912523B/zh
Publication of WO2015152650A1 publication Critical patent/WO2015152650A1/ko
Priority to US16/158,171 priority patent/US10916710B2/en
Priority to US17/064,409 priority patent/US11877510B2/en

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Definitions

  • the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually 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 to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Described herein is a heterocyclic compound and an organic light emitting device comprising the same.
  • Ar1 and Ar2 are the same as each other, deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthioxy and arylthioxy , Alkyl sulfoxy group, aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a group, an arylphosphine group, and a heterocyclic group; Deuterium, halogen group, nitrile group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amino
  • L is substituted or unsubstituted phenylene; Or substituted or unsubstituted biphenylylene,
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstit
  • R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstit
  • n 1 to 5
  • a is an integer of 0 to 3
  • b is an integer from 0 to 4,
  • an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, luminescence, electron transport, or electron injection materials.
  • the compounds described herein may be preferably used as a light emitting layer, an electron transport or electron injection material, more preferably may be used as a material for electron transport or electron injection.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exe
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • substituted or unsubstituted is preferably deuterium; An alkyl group; An alkoxy group; And it may mean that it is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups.
  • the compound represented by Formula 1 may be substituted or unsubstituted with at least one deuterium.
  • the substituent of the compound represented by Formula 1 may be substituted or unsubstituted with at least one deuterium.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group may be represented by a chemical formula of -SiRR'R ", wherein R, R 'and R" are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.
  • the boron group may be represented by the formula of -BRR'R ", wherein R, R 'and R" are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • aryl amine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or may be a polycyclic heterocyclic group.
  • the heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
  • examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
  • the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • examples of the aryl amine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group or a substituted or unsubstituted monocyclic and polycyclic diaryl. It means an amine group.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, triphenylene group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group including one or more of N, O, P, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazo
  • hetero aryl group is aromatic
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
  • the description of one aryl group may apply.
  • the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
  • heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl group may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • heteroarylene is a divalent group.
  • the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, and the like.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.
  • the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.
  • Ar1, Ar2, L, R3, R4, a, b and m are the same as defined in Formula 1,
  • R11, R12, R21 and R22 are the same as those of R3 and R4,
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsub
  • r11 and r12 are the same as or different from each other, and each independently an integer of 0 to 5,
  • r21 and r22 are the same as or different from each other, and each independently an integer of 0 to 4,
  • Formula 1 may be represented by any one of 5 to 8.
  • Ar 1, Ar 2, L, R 1 to R 4, m, a, and b are defined in Formula 1.
  • Chemical Formula 2 may be represented by any one of the following Chemical Formulas 2-1 to 2-4.
  • Ar1, Ar2, L, R3, R4, a and b are the same as defined in Formula 1,
  • R 11, R 12, r 11 and r 12 are as shown in Formula 2.
  • Chemical Formula 3 may be represented by any one of the following Chemical Formulas 3-1 to 3-4.
  • Ar1, Ar2, L, R3, R4, a and b are the same as defined in Formula 1,
  • X1 and X2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
  • X1 and X2 are the same as or different from each other, and each independently an alkyl group.
  • X1 and X2 are a methyl group.
  • Ar1 and Ar2 are the same as each other, deuterium, and a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group; Or a phenanthryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group.
  • Ar1 and Ar2 are the same as each other, a phenyl group unsubstituted or substituted with deuterium; Naphthyl group unsubstituted or substituted with deuterium; Naphthyl group unsubstituted or substituted with deuterium; Or a phenanthryl group unsubstituted or substituted with deuterium.
  • Ar1 and Ar2 are the same as each other, a phenyl group; Biphenyl group; Naphthyl group; Or a phenanthryl group.
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; Phosphine oxide groups; An aryl group unsubstituted or substituted with deuterium, an alkyl group or an alkoxy group; Or a heterocyclic group, or may be combined
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring.
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Deuterium, halogen group, nitrile group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkyl sulfoxy group, aryl sulfoxide Period, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, aryl force An alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a pin group and a heterocyclic group; Or deuterium, halogen group, nit
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkoxy group, and an aryl group; Or an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkoxy group, and an aryl group, or one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkoxy group, and an aryl group in combination with each other To form a substituted or unsubstituted ring.
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; An alkyl group; Or an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group, and an alkoxy group, or combine with each other to form a ring.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted monocyclic to tricyclic aryl group, or combine with each other to form a substituted or unsubstituted ring.
  • R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a substituted or unsubstituted ring.
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; An alkyl group; Or an aryl group, or combine with each other to form a ring.
  • the R1 and R2 are the same as or different from each other, and each independently an alkyl group; Or an aryl group, or combine with each other to form a ring.
  • the R1 and R2 are the same as or different from each other, and each independently an alkyl group; Or a phenyl group, or combine with each other to form a ring.
  • the R1 and R2 are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or combine with each other to form a ring.
  • the R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Aryl phosphine group; Or a phosphine oxide group.
  • the R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Or an alkyl group.
  • R3 and R4 are hydrogen.
  • R4 is hydrogen
  • R3 is hydrogen
  • L is deuterium, halogen group, nitrile group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio Aryl thioxy group, alkyl sulfoxy group, aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group Phenylene unsubstituted or substituted with one or more substituents selected from the group consisting of a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; Or deuterium, halogen group, nitrile group, nitro group, hydroxy group,
  • L is phenylene; Or biphenylylene.
  • L may be any one selected from the following structures.
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • the The part can be any one selected from the following structures.
  • R1 and R2 have the same definition as in Formula 1,
  • the structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
  • m is 1.
  • m is 1 or 2.
  • the compound of Formula 1 may be any one selected from the following compounds.
  • the compound represented by Chemical Formula 1 may be prepared based on the preparation examples described below. According to one embodiment, it may be prepared in the same manner as in Scheme 1 below.
  • Ar 1, Ar 2, L, R 1, R 2, R 3, R 4, a, b, and m are defined in Formula 1.
  • a compound of Chemical Formula 1 is prepared by coupling a triazine derivative compound substituted with halogen and an aromatic compound substituted with boronic acid or boronic acid derivatives using a palladium catalysis. can do.
  • organic light emitting device including the compound represented by any one of Formulas 1 to 8.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound of any one of Formulas 1 to 8. Provided is an element.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention 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 and the like as an organic material layer.
  • 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 a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes
  • the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes is It includes a compound of formula (1).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes any one of Formulas 1 to 8.
  • the electron transport layer, the electron injection layer or the layer at the same time the electron transport and electron injection comprises a compound of the formula (1).
  • the organic material layer includes a light emitting layer and an electron transport layer
  • the electron transport layer includes any one of Formulas 1 to 8.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of any one of Formulas 1 to 8. .
  • the organic material layers may be formed of the same material or different materials.
  • the first electrode A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode.
  • An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
  • two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously performing electron transport and electron injection, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound.
  • the heterocyclic compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • heterocyclic compound when included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
  • the organic light emitting device of the present specification is a material known in the art, except that at least one layer of the organic material layer includes any one compound of Formulas 1 to 8, that is, a compound represented by any one of Formulas 1 to 8. It can be prepared by the method.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • 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 of any one of Formulas 1 to 8 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, 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.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) 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-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, 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 light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including 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 cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 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-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 500 kPa was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following compound [HI-A] was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound [HAT] (50 kPa) and the following compound [HT-A] (600 kPa) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
  • aluminum 2 ⁇ / sec the vacuum degree during deposition was 1 ⁇ 10
  • An organic light-emitting device was manufactured by maintaining ⁇ 7 to 5 ⁇ 10 ⁇ 8 torr.
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 2] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 3] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 5] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 7] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 13] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 27] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 32] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 36] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 80] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [ET-A] was used instead of [Compound 1] of [Example 1].
  • An organic light emitting device was manufactured in the same manner as in [Example 1], except that [ET-B] was used instead of [Compound 1] of [Example 1].
  • the driving voltage and the luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA / cm 2 , and a time (T 90 ) 90% of the initial luminance at a current density of 20 mA / cm 2 was measured. Measured. The results are shown in Table 1 below.
  • the compound represented by the formula (1) according to the present invention can be used in the organic layer capable of simultaneous electron injection and electron transport of the organic light emitting device.
  • the organic light emitting device using the same it has a low driving voltage and high efficiency, and the stability of the device can be improved by hole stability of the compound.
  • the compound represented by Chemical Formula 1 according to the present invention has excellent thermal stability, and when used in an organic layer capable of simultaneously injecting and transporting electrons, it is possible to mix n-type dopants.
PCT/KR2015/003291 2014-04-04 2015-04-02 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 WO2015152650A1 (ko)

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US15/301,607 US10510963B2 (en) 2014-04-04 2015-04-02 Heterocyclic compound and organic light-emitting element comprising same
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US16/158,171 US10916710B2 (en) 2014-04-04 2018-10-11 Heterocyclic compound and organic light-emitting element comprising same
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WO2017179883A1 (ko) * 2016-04-12 2017-10-19 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
CN107353281A (zh) * 2016-05-10 2017-11-17 株式会社Lg化学 新型化合物及包含它的有机发光元件
CN107814775A (zh) * 2016-09-12 2018-03-20 Cmdl有限公司 芴基三嗪衍生物有机化合物及包含其的有机电致发光器件
WO2018117562A1 (ko) * 2016-12-20 2018-06-28 주식회사 두산 유기 화합물 및 이를 이용한 유기 전계 발광 소자
CN108349914A (zh) * 2015-10-27 2018-07-31 株式会社Lg化学 有机发光器件
CN108701773A (zh) * 2016-02-19 2018-10-23 诺瓦尔德股份有限公司 包含用于有机发光二极管(oled)的基质化合物混合物的电子传输层
CN110248930A (zh) * 2017-02-15 2019-09-17 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN110800122A (zh) * 2017-08-02 2020-02-14 株式会社Lg化学 有机电致发光器件
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