US20230114182A1 - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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US20230114182A1
US20230114182A1 US17/611,452 US202017611452A US2023114182A1 US 20230114182 A1 US20230114182 A1 US 20230114182A1 US 202017611452 A US202017611452 A US 202017611452A US 2023114182 A1 US2023114182 A1 US 2023114182A1
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Seonwoo KIM
Hojung Lee
Sujeong GEUM
Hoon Jun Kim
Jae Seung Ha
Ji Young Choi
Wanpyo HONG
Woochul LEE
Joo Ho Kim
Moung Gon KIM
Kyunghee KIM
Hye Min CHO
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LG Chem Ltd
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LG Chem Ltd
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Assigned to LG CHEM, LTD. reassignment LG CHEM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HONG, Wanpyo, LEE, Woochul, CHO, HYE MIN, CHOI, JI YOUNG, GEUM, Sujeong, HA, JAE SEUNG, KIM, HOON JUN, KIM, JOO HO, KIM, KYUNGHEE, KIM, MOUNG GON, KIM, Seonwoo, LEE, HOJUNG
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Definitions

  • the present specification relates to an organic light emitting device.
  • an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween.
  • the organic material layer has in many cases a multi-layered structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device, and for example, may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides an organic light emitting device.
  • the present specification provides an organic light emitting device including: a positive electrode; a negative electrode; and an organic material layer including a light emitting layer provided between the positive electrode and the negative electrode,
  • the light emitting layer includes one or more of compounds represented by any one of the following Formulae 1-1 to 1-3 and a compound represented by the following Formula 2.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group,
  • n11, n21, and n31 are each an integer from 0 to 6
  • n12, n13, n22, n32, and n33 are each an integer from 0 to 7
  • n23 is an integer from 0 to 5
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,
  • Ar12, Ar13, Ar23, Ar24, Ar31, and Ar32 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
  • n11 and m21 are an integer from 0 or 4, and m22 is an integer from 1 to 5,
  • Formulae 1-1 to 1-3 each have at least one or more deuteriums
  • A1 to A3 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,
  • At least one of A1 and A2 is represented by Formula 2-C,
  • X is NRa1; O; or S,
  • E1 is one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,
  • R1 to R5 and Ra1 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,
  • r1 to r3 are an integer from 1 to 4, and when r1 to r3 are 2 or higher, substituents in the parenthesis are the same as or different from each other, and
  • the organic light emitting device described in the present specification has a low driving voltage and has excellent efficiency characteristics and an excellent service life by including one or more of compounds represented by any one of Formulae 1-1 to 1-3 and a compound represented by Formula 2 in a light emitting layer.
  • FIGS. 1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
  • the present specification provides an organic light emitting device including a light emitting layer including compounds represented by any one of Formulae 1-1 to 1-3 and a compound represented by Formula 2. Specifically, the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 are included as a host and a dopant, respectively.
  • the compound represented by Formula 2 has excellent light emission characteristics due to a narrow full-width at half-maximum, but the service life performance thereof is slightly insufficient.
  • Formulae 1-1 to 1-3 include deuterium.
  • the service life of a device is improved.
  • chemical properties of the compound are rarely changed.
  • the atomic weight of deuterium is twice that of hydrogen, physical properties of a deuterated compound may be changed.
  • a compound substituted with deuterium has a lower level of vibrational energy. Quantum calculations revealed changes in the vibrational energy according to the deuterium substitution rate of the compound, but a vibrational energy of about 2 kcal/mol was decreased constantly for each number of deuterium substitutions.
  • the compound substituted with deuterium may prevent a decrease in quantum efficiency caused by a decrease in intermolecular Van der Waals force or a collision due to intermolecular vibration.
  • the stability of the compound may be improved by a C-D bond, which is stronger than a C—H bond.
  • the organic light emitting device of the present invention may include compounds represented by Formulae 1-1 to 1-3 and a compound represented by Formula 2 together, thereby improving a service life problem while maintaining excellent light emission characteristics of the compound of Formula 2.
  • the compounds of Formulae 1-1 to 1-3 including deuterium may be prepared by a publicly-known deuteration reaction.
  • the compounds represented by Formulae 1-1 to 1-3 may be formed using a deuterated compound as a precursor, or deuterium may also be introduced into a compound via a hydrogen-deuterium exchange reaction in the presence of an acid catalyst using a deuterated solvent.
  • N % substitution with deuterium means that N % of hydrogen available in the corresponding structure is substituted with deuterium.
  • 25% substitution of dibenzofuran with deuterium means that two of eight hydrogens of dibenzofuran are substituted with deuteriums.
  • the degree of deuteration may be confirmed by a publicly-known method such as nuclear magnetic resonance spectroscopy ( 1 H NMR) or GC/MS.
  • the substitution includes being substituted with deuterium even when the substituted substituent is not specified.
  • * means a moiety that is fused or linked.
  • Cn means n carbon atoms.
  • Cn-Cm means “n to m carbon atoms”.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and a position to be substituted is not limited as long as the position is a position at which the hydrogen atom is substituted, that is, a position at which the substituent may be substituted, and when two or more are substituted, the two or more substituents may be the same as or different from each other.
  • the term “substituted or unsubstituted” means being substituted with one or two or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an aryl group; and a heterocyclic group, being substituted with a substituent to which two or more substituents among the exemplified substituents are linked, or having no substituent.
  • the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent to which two phenyl groups are linked.
  • the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C20 alkyl group; a C3-C60 cycloalkyl group; a C6-C60 aryl group; and a C2-C60 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.
  • substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C20 alkyl group; a C3-C60 cycloalkyl group; a C6-C60 aryl group; and a C2-C60 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or
  • the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C10 alkyl group; a C3-C30 cycloalkyl group; a C6-C30 aryl group; and a C2-C30 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.
  • substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C10 alkyl group; a C3-C30 cycloalkyl group; a C6-C30 aryl group; and a C2-C30 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or
  • the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C6 alkyl group; a C3-C20 cycloalkyl group; a C6-C20 aryl group; and a C2-C20 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.
  • the fact that two or more substituents are linked indicates that hydrogen of any one substituent is changed into another substituent.
  • an isopropyl group and a phenyl group may be linked to each other to become a substituent of
  • the case where three substituents are linked to one another includes not only a case where (Substituent 1)-(Substituent 2)-(Substituent 3) are consecutively linked to one another, but also a case where (Substituent 2) and (Substituent 3) are linked to (Substituent 1).
  • two phenyl groups and an isopropyl group may be linked to each other to become a substituent of
  • substituted with A or B includes not only the case of being substituted with A alone or with B alone, but also the case of being substituted with A and B.
  • an alkyl group may be straight-chained or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 20. Specifically, the number of carbon atoms is more preferably 1 to 10; or 1 to 6.
  • the alkoxy group is one in which an alkyl group is linked to an oxygen atom
  • the alkylthio group is one in which an alkyl group is linked to a sulfur atom
  • the above-described description on the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.
  • an alkenyl group may be straight-chained or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30; 2 to 20; 2 to 10; or 2 to 5.
  • Specific examples thereof 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.
  • a cycloalkyl group is not particularly limited, but has preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6.
  • the cycloalkyl group includes not only a single ring group, but also a double ring group such as a bridgehead, a fused ring, and a spiro ring.
  • cyclopropyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but are not limited thereto.
  • cycloalkene is a ring group which has a double bond present in a hydrocarbon ring, but is not aromatic, and the number of carbon atoms thereof is not particularly limited, but may be 3 to 60, and may be 3 to 30 according to an exemplary embodiment.
  • the cycloalkene includes not only a single ring group, but also a double ring group such as a bridgehead, a fused ring, and a spiro ring.
  • Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, cyclohexene, and the like, but are not limited thereto.
  • a silyl group may be represented by a formula of —SiY 11 Y 12 Y 13 , and the Y 11 , Y 12 , and Y 13 may be each hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
  • silyl group examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but are not limited thereto.
  • an amine group may be selected from the group consisting of —NH 2 ; an alkylamine group; an alkylarylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group; and a heteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. In the case of an arylamine group, the number of carbon atoms thereof is 6 to 60. According to another exemplary embodiment, the number of carbon atoms of the arylamine group is 6 to 40.
  • the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; an anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; an N-phenylnaphthylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group;
  • the alkylamine group means an amine group in which an alkyl group is substituted with N of the amine group, and includes a dialkylamine group, an alkylarylamine group, and an alkylheteroarylamine group.
  • the arylamine group means an amine group in which an aryl group is substituted with N of the amine group, and includes a diarylamine group, an arylheteroarylamine group, and an alkylarylamine group.
  • the heteroarylamine group means an amine group in which a heteroaryl group is substituted with N of the amine group, and includes a diheteroarylamine group, an arylheteroarylamine group, and an alkylheteroarylamine group.
  • an alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • an arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • an alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • an aryl group is not particularly limited, but has preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of a monocyclic aryl group as the aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • polycyclic aryl group examples include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but are not limited thereto.
  • No. 9 carbon atom (C) of a fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.
  • the substituted aryl group may also include a form in which an aliphatic ring is fused to the aryl group.
  • a tetrahydronaphthalene group, a dihydroindene group and a dihydroanthracene group having the following structures are included in the substituted aryl group.
  • one of the carbons of a benzene ring may be linked to another position.
  • a fused hydrocarbon ring group means a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and is a form in which the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring are fused.
  • the fused ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring include a tetrahydronaphthalene group, a dihydroindene group, and a dihydroanthracene group, but are not limited thereto.
  • the alkylaryl group means an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further linked.
  • an arylalkyl group means an alkyl group substituted with an aryl group, and a substituent other than the alkyl group may be further linked.
  • the aryloxy group is one in which an aryl group is linked to an oxygen atom
  • the arylthio group is one in which an aryl group is linked to a sulfur atom
  • the above-described description on the aryl group may be applied to the aryl group of the aryloxy group and the arylthio group.
  • An aryl group of an aryloxy group is the same as the above-described examples of the aryl group.
  • examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like
  • examples of the arylthioxy group include a phenylthioxy group, a 2-methylphenylthioxy group,
  • a heterocyclic group is a cyclic group including one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20.
  • heterocyclic group examples include a pyridyl group; a quinoline group; a thiophene group; a dibenzothiophene group; a furan group; a dibenzofuran group; a naphthobenzofuran group; a carbazole group; a benzocarbazole group; a naphthobenzothiophene group; a dibenzosilole group; a naphthobenzosilole group; a hexahydrocarbazole group; dihydroacridine group; a dihydrodibenzoazasiline group; a phenoxazine group; a phenothiazine group; a dihydrodibenzoazasiline group; a spiro(dibenzosilole-dibenzoazasiline) group; a spiro(acridine-fluorene) group, and the like, but are
  • heterocyclic group may be applied to a heteroaryl group except for being aromatic.
  • an aromatic hydrocarbon ring means a hydrocarbon ring in which pi electrons are completely conjugated and are planar, and the description on the aryl group may be applied to an aromatic hydrocarbon ring except for being divalent.
  • the number of carbon atoms of the aromatic hydrocarbon ring may be 6 to 60; 6 to 30; 6 to 20; or 6 to 10.
  • an aliphatic hydrocarbon ring has a cyclically bonded structure, and means a non-aromatic ring.
  • the aliphatic hydrocarbon ring include cycloalkyl or cycloalkene, and the above-described description on the cycloalkyl group or cycloalkenyl group may be applied to the aliphatic hydrocarbon ring except for being divalent.
  • the number of carbon atoms of the aliphatic hydrocarbon ring may be 3 to 60; 3 to 30; 3 to 20; 3 to 10; 5 to 50; 5 to 30; 5 to 20; 5 to 10; or 5 and 6.
  • a substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which aromatic rings are fused.
  • a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring form a fused ring.
  • the fused ring of the aromatic ring and the aliphatic ring include a 1,2,3,4-tetrahydronaphthalene group, a 2,3-dihydro-1H-indene group, and the like, but are not limited thereto.
  • the “adjacent” group may mean a substituent substituted with an atom directly linked to an atom in which the corresponding substituent is substituted, a substituent disposed to be sterically closest to the corresponding substituent, or another substituent substituted with an atom in which the corresponding substituent is substituted.
  • two substituents substituted at the ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as groups which are “adjacent” to each other.
  • substituents (four in total) linked to two consecutive carbons in an aliphatic ring may be interpreted as “adjacent” groups.
  • the “adjacent groups are bonded to each other to form a ring” among the substituents means that a substituent is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring.
  • a five-membered or six-membered ring formed by bonding adjacent groups means that a ring including a substituent participating in the ring formation is five-membered or six-membered. It is possible to include an additional ring fused to the ring including the substituent participating in the ring formation.
  • the aliphatic hydrocarbon ring when a substituent of an aromatic hydrocarbon ring or an aryl group is bonded to an adjacent substituent to form an aliphatic hydrocarbon ring, the aliphatic hydrocarbon ring includes two pi electrons (carbon-carbon double bond) of an aromatic hydrocarbon ring or an aryl group, even though a double bond is not specified.
  • aryl group may be applied to an arylene group except for being divalent.
  • cycloalkyl group may be applied to a cycloalkylene group except for being divalent.
  • Formulae 1-1 to 1-3 each include at least one or more deuteriums.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C10 alkyl group.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C13 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C10 aryl group which is unsubstituted or substituted with deuterium.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group which is unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.
  • Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.
  • Ar11 is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.
  • Ar11 is a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group which is unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.
  • Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.
  • one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.
  • one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.
  • one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.
  • one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.
  • one or Ar12 and Ar13 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.
  • Ar12 and Ar13 are each hydrogen; or deuterium.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C10 alkyl group.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C13 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.
  • one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.
  • Ar23 and Ar24 are each hydrogen; or deuterium.
  • one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.
  • one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.
  • one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.
  • one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.
  • one or Ar31 and Ar32 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.
  • Ar31 and Ar32 are each hydrogen; or deuterium.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 10 carbon atoms, which is unsubstituted or substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond; a phenylene group which is unsubstituted or substituted with deuterium; or a naphthylene group which is unsubstituted or substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond or any one selected from the following structures.
  • D means deuterium
  • k1 is an integer from 0 to 4
  • k2 is an integer from 0 to 6.
  • k1 is an integer from 1 to 4.
  • k2 is an integer from 1 to 6. In an exemplary embodiment of the present specification, kl is 1 or higher. In another exemplary embodiment, k1 is 2 or higher. In still another exemplary embodiment, k1 is 3 or higher. In yet another exemplary embodiment, k1 is 4.
  • k2 is 1 or higher. In another exemplary embodiment, k2 is 2 or higher. In still another exemplary embodiment, k2 is 3 or higher. In yet another exemplary embodiment, k2 is 4 or higher. In yet another exemplary embodiment, k2 is 5 or higher. In yet another exemplary embodiment, k2 is 6.
  • m11 is 0.
  • m11 is 1.
  • m22 is 1 or higher.
  • m22 is 1.
  • m11+n12 is an integer from 0 to 7.
  • m21+n22 is an integer from 0 to 7.
  • m22+n23 is an integer from 0 to 7.
  • n11 is 1 or higher. In another exemplary embodiment, n11 is 2 or higher. In another exemplary embodiment, n11 is 3 or higher. In another exemplary embodiment, n11 is 4 or higher. In another exemplary embodiment, n11 is 5 or higher. In yet another exemplary embodiment, n11 is 6.
  • n12 is 1 or higher. In another exemplary embodiment, n12 is 2 or higher. In still another exemplary embodiment, n12 is 3 or higher. In yet another exemplary embodiment, n12 is 4 or higher. In yet another exemplary embodiment, n12 is 5 or higher. In yet another exemplary embodiment, n12 is 6 or higher. In yet another exemplary embodiment, n12 is 7.
  • n13 is 1 or higher. In another exemplary embodiment, n13 is 2 or higher. In still another exemplary embodiment, n13 is 3 or higher. In yet another exemplary embodiment, n13 is 4 or higher. In yet another exemplary embodiment, n13 is 5 or higher. In yet another exemplary embodiment, n13 is 6 or higher. In yet another exemplary embodiment, n13 is 7.
  • n11+n12+n13 is 2 or higher. In another exemplary embodiment, n11+n12+n13 is 4 or higher. In still another exemplary embodiment, n11+n12+n13 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13 is 14 or higher. In yet another exemplary embodiment, n11+n12+n13 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13 is 20.
  • n11+n12+n13 is 19 or lower. In another exemplary embodiment, n11+n12+n13 is 17 or lower. In still another exemplary embodiment, n11+n12+n13 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13 is 13 or lower. In yet another exemplary embodiment, n11+n12+n13 is 11 or lower. In yet another exemplary embodiment, n11+n12+n13 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13 is 7 or lower. In yet another exemplary embodiment, n11+n12+n13 is 5 or lower.
  • n11+n12+n13+k1 is 2 or higher. In another exemplary embodiment, n11+n12+n13+k1 is 4 or higher. In still another exemplary embodiment, n11+n12+n13+k1 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 14 or higher.
  • n11+n12+n13+k1 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 20 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 22 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 24.
  • n11+n12+n13+k1 is 23 or lower. In another exemplary embodiment, n11+n12+n13+k1 is 21 or lower. In still another exemplary embodiment, n11+n12+n13+k1 is 19 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 17 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 13 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 11 or lower.
  • n11+n12+n13+k1 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 7 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 5 or lower.
  • n11+n12+n13+k2 is 2 or higher. In another exemplary embodiment, n11+n12+n13+k2 is 4 or higher. In still another exemplary embodiment, n11+n12+n13+k2 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 14 or higher.
  • n11+n12+n13+k2 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 20 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 22 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 24 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 26.
  • n11+n12+n13+k2 is 25 or lower. In another exemplary embodiment, n11+n12+n13+k2 is 23 or lower. In still another exemplary embodiment, n11+n12+n13+k2 is 21 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 19 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 17 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 13 or lower.
  • n11+n12+n13+k2 is 11 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 7 or lower.
  • n21 is 1 or higher. In another exemplary embodiment, n21 is 2 or higher. In still another exemplary embodiment, n21 is 3 or higher. In yet another exemplary embodiment, n21 is 4 or higher. In yet another exemplary embodiment, n21 is 5 or higher. In yet another exemplary embodiment, n21 is 6.
  • n22 is 1 or higher. In another exemplary embodiment, n22 is 2 or higher. In still another exemplary embodiment, n22 is 3 or higher. In yet another exemplary embodiment, n22 is 4 or higher. In yet another exemplary embodiment, n22 is 5 or higher. In yet another exemplary embodiment, n22 is 6 or higher. In yet another exemplary embodiment, n22 is 7.
  • n23 is 1 or higher. In another exemplary embodiment, n23 is 2 or higher. In still another exemplary embodiment, n23 is 3 or higher. In yet another exemplary embodiment, n23 is 4 or higher. In yet another exemplary embodiment, n23 is 5.
  • n21+n22+n23 is 2 or higher. In another exemplary embodiment, n21+n22+n23 is 4 or higher. In still another exemplary embodiment, n21+n22+n23 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23 is 14 or higher. In yet another exemplary embodiment, n21+n22+n23 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23 is 18.
  • n21+n22+n23 is 17 or lower. In another exemplary embodiment, n21+n22+n23 is 15 or lower. In still another exemplary embodiment, n21+n22+n23 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23 is 11 or lower. In yet another exemplary embodiment, n21+n22+n23 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23 is 5 or lower.
  • n21+n22+n23+k1 is 2 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 4 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 14 or higher.
  • n21+n22+n23+k1 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 18 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 20 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 22.
  • n21+n22+n23+k1 is 21 or lower. In another exemplary embodiment, n21+n22+n23+k1 is 19 or lower. In still another exemplary embodiment, n21+n22+n23+k1 is 17 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 15 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 11 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 5 or lower.
  • n21+n22+n23+k2 is 2 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 4 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 14 or higher.
  • n21+n22+n23+k2 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 18 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 20 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 22 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 24.
  • n21+n22+n23+k2 is 23 or lower. In another exemplary embodiment, n21+n22+n23+k2 is 21 or lower. In still another exemplary embodiment, n21+n22+n23+k2 is 19 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 17 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 15 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 11 or lower.
  • n21+n22+n23+k2 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 5 or lower.
  • n31 is 1 or higher. In another exemplary embodiment, n31 is 2 or higher. In still another exemplary embodiment, n31 is 3 or higher. In yet another exemplary embodiment, n31 is 4 or higher. In yet another exemplary embodiment, n31 is 5 or higher. In yet another exemplary embodiment, n31 is 6.
  • n32 is 1 or higher. In another exemplary embodiment, n32 is 2 or higher. In still another exemplary embodiment, n32 is 3 or higher. In yet another exemplary embodiment, n32 is 4 or higher. In yet another exemplary embodiment, n32 is 5 or higher. In yet another exemplary embodiment, n32 is 6 or higher. In yet another exemplary embodiment, n32 is 7.
  • n33 is 1 or higher. In another exemplary embodiment, n33 is 2 or higher. In still another exemplary embodiment, n33 is 3 or higher. In yet another exemplary embodiment, n33 is 4 or higher. In yet another exemplary embodiment, n33 is 5 or higher. In yet another exemplary embodiment, n33 is 6 or higher. In yet another exemplary embodiment, n33 is 7.
  • n31+n32+n33 is 2 or higher. In another exemplary embodiment, n31+n32+n33 is 4 or higher. In still another exemplary embodiment, n31+n32+n33 is 6 or higher. In yet another exemplary embodiment, n31+n32+n33 is 8 or higher. In yet another exemplary embodiment, n31+n32+n33 is 10 or higher. In yet another exemplary embodiment, n31+n32+n33 is 12 or higher. In yet another exemplary embodiment, n31+n32+n33 is 14 or higher. In yet another exemplary embodiment, n31+n32+n33 is 16 or higher. In yet another exemplary embodiment, n31+n32+n33 is 18 or higher. In yet another exemplary embodiment, n31+n32+n33 is 20.
  • n31+n32+n33 is 19 or lower. In another exemplary embodiment, n31+n32+n33 is 17 or lower. In still another exemplary embodiment, n31+n32+n33 is 15 or lower. In yet another exemplary embodiment, n31+n32+n33 is 13 or lower. In yet another exemplary embodiment, n31+n32+n33 is 11 or lower. In yet another exemplary embodiment, n31+n32+n33 is 9 or lower. In yet another exemplary embodiment, n31+n32+n33 is 7 or lower. In yet another exemplary embodiment, n31+n32+n33 is 5 or lower.
  • n31+n32+n33+k1 is 2 or higher. In another exemplary embodiment, n31+n32+n33+k1 is 4 or higher. In still another exemplary embodiment, n31+n32+n33+k1 is 6 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 8 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 10 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 12 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 14 or higher.
  • n31+n32+n33+k1 is 16 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 18 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 20 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 22 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 24.
  • n31+n32+n33+k1 is 23 or lower. In another exemplary embodiment, n31+n32+n33+k1 is 21 or lower. In still another exemplary embodiment, n31+n32+n33+k1 is 19 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 17 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 15 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 13 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 11 or lower.
  • n31+n32+n33+k1 is 9 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 7 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 5 or lower.
  • 30% or more of Formulae 1-1 to 1-3 are substituted with deuterium.
  • 40% or more of Formulae 1-1 to 1-3 are substituted with deuterium.
  • 60% or more of Formulae 1-1 to 1-3 are substituted with deuterium.
  • 80% or more of Formulae 1-1 to 1-3 are substituted with deuterium.
  • 100% of Formulae 1-1 to 1-3 are substituted with deuterium.
  • n11 is 6, and Ar12 and Ar13 are deuterium.
  • n21 is 6, and Ar23 and Ar24 are deuterium.
  • n31 is 6, and Ar31 and Ar32 are deuterium.
  • Formulae 1-1 to 1-3 include at least one hydrogen. That is, Formulae 1-1 to 1-3 are deuterated to less than 100%.
  • Formula 1-1 is any one selected from the following Formulae 101 to 104.
  • Formula 1-2 is any one selected from the following Formulae 111 to 114.
  • Formula 1-3 is any one selected from the following Formulae 121 to 124.
  • Formulae 1-1 and 1-2 are represented by Formula 101, 102, 111, or 112.
  • the driving voltage of the device is low, which is advantageous in constructing a highly efficient device.
  • the compound represented by Formula 1-1 is any one selected from the following compounds.
  • the compound represented by Formula 1-2 is any one selected from the following compounds.
  • the compound represented by Formula 1-3 is any one selected from the following compounds.
  • A1 to A3 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused.
  • At least one of A1 and A2 is represented by the following Formula 2-C.
  • X is NRa1; 0; or S.
  • Ra1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.
  • Ra1 is a substituted or unsubstituted aryl group.
  • Ra1 is a substituted or unsubstituted C6-C30 aryl group.
  • Ra1 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C10 alkyl group, or a substituent to which two or more groups selected from the above group are linked.
  • Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C6 alkyl group, a substituent to which two or more groups selected from the above group are linked.
  • Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 alkyl group.
  • Ra1 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, or CD 3 .
  • E1 is one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,
  • E1 is one ring selected from the group consisting of a C6-C20 aromatic hydrocarbon ring, a C5-C20 aliphatic hydrocarbon ring, a C2-C20 aromatic hetero ring containing 0, a C2-C20 aliphatic hetero ring containing 0, a C2-C20 aromatic hetero ring containing S, a C2-C20 aliphatic hetero ring containing S, a C2-C20 aromatic hetero ring containing N, and a C2-C20 aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.
  • E1 is one ring selected from the group consisting of a C6-C10 aromatic hydrocarbon ring, a C5-C10 aliphatic hydrocarbon ring, a C2-C10 aromatic hetero ring containing 0, a C2-C10 aliphatic hetero ring containing 0, a C2-C10 aromatic hetero ring containing S, a C2-C10 aliphatic hetero ring containing S, a C2-C10 aromatic hetero ring containing N, and a C2-C10 aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.
  • E1 is one ring selected from the group consisting of a monocyclic or bicyclic aromatic hydrocarbon ring, a monocyclic or bicyclic aliphatic hydrocarbon ring, a monocyclic or bicyclic aromatic hetero ring containing O, a monocyclic or bicyclic aliphatic hetero ring containing O, a monocyclic or bicyclic aromatic hetero ring containing S, a monocyclic or bicyclic aliphatic hetero ring containing S, a monocyclic or bicyclic aromatic hetero ring containing N, and a monocyclic or bicyclic aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.
  • E1 forms one ring selected from the group consisting of a benzene ring; an indene ring; a furan ring; a benzofuran ring; a thiophene ring; a benzothiophene ring; a silole ring; a benzosilole ring; a pyrrole ring; an indole ring; a cyclopentene ring; a cyclohexene ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a dihydrofuran ring; a dihydrothiophene ring; and a dihydrosilole ring, or a ring in which two selected from the above group are fused.
  • E1 is a benzene ring; a cyclopentene ring; a cyclohexne ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a tetrahydronaphthalene ring; a dihydroindene ring; a tetrahydromethanonaphthalene ring; or a tetrahydroethanonaphthalene ring.
  • E1 is selected from the following structures.
  • the rings having the following structure are unsubstituted or substituted with R1 or R2.
  • Y3 is O; S; Si(Ra6) (Ra7); or N(Ra8),
  • Y4 is O; S; Si(Ra6) (Ra7); C(Ra6) (Ra7); or N(Ra8), and
  • Ra6 to Ra8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring.
  • Ra6 to Ra8 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.
  • Ra6 to Ra8 are the same as or different from each other, and are each independently C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C6 alkyl group, and a C1-C6 alkoxy group or a substituent to which two or more groups selected from the above group are linked, or are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.
  • Ra6 to Ra8 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, or are bonded to each other to form a fluorene ring which is unsubstituted or substituted with a methyl group, an isopropyl group, or a tert-butyl group.
  • Ra8 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.
  • Ra8 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.
  • Ra8 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.
  • At least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a C6-C30 aromatic hydrocarbon ring in which a C5-C30 hydrocarbon ring or a C2-C30 hetero ring is fused or unfused.
  • At least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a C6-C10 aromatic hydrocarbon ring in which a C5-C10 hydrocarbon ring or a C2-C10 hetero ring is fused or unfused.
  • At least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a benzene ring; or a naphthalene ring.
  • A1 is represented by Formula 2-C, and A2 is a benzene ring.
  • A1 is a benzene ring
  • A2 is represented by Formula 2-C.
  • A1 and A2 are the same as or different from each other, and are each independently represented by Formula 2-C.
  • A3 is a benzene ring.
  • Formula 2 is represented by any one selected from the following Formulae 204 to 207.
  • R1 to R5, r1, and r3 are the same as those defined in Formula 2,
  • E1 and E2 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,
  • X1 and X2 are the same as or different from each other, and are each independently NRa1; O; or S,
  • Ra1's are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring, and
  • r1′′ and r2′′ are an integer of 1 or higher, and when r1′′ and r2′′ are each 2 or higher, substituents in the parenthesis are the same as or different from each other.
  • a plurality of R1′′'s are the same as or different from each other.
  • a plurality of R2′′'s are the same as or different from each other.
  • r1, r2, r1′′, and r2′′ are an integer of 10 or lower. In another exemplary embodiment, r1, r2, r1′′, and r2′′ are an integer of 8 or lower. In still another exemplary embodiment, r1, r2, r1′′, and r2′′ are an integer of 4 or lower.
  • E1 and E2 are the same as or different from each other, and are each independently a C6-C20 aromatic hydrocarbon ring; a C5-C20 aliphatic hydrocarbon ring; or a fused ring of a C6-C20 aromatic hydrocarbon ring and a C5-C20 aliphatic hydrocarbon ring.
  • E1 and E2 are the same as or different from each other, and are each independently a monocyclic to bicyclic aromatic hydrocarbon ring; a monocyclic to bicyclic aliphatic hydrocarbon ring; or a fused ring of a monocyclic aromatic hydrocarbon ring and a monocyclic aliphatic hydrocarbon ring.
  • E1 and E2 are the same as or different from each other, and each independently form one ring selected from the group consisting of a benzene ring; an indene ring; a furan ring; a benzofuran ring; a thiophene ring; a benzothiophene ring; a silole ring; a benzosilole ring; a pyrrole ring; an indole ring; a cyclopentene ring; a cyclohexene ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a dihydrofuran ring; a dihydrothiophene ring; and a dihydrosilole ring, or a ring in which two selected from the above group are fused.
  • E1 and E2 are the same as or different from each other, and are each independently a benzene ring; a cyclopentene ring; a cyclohexne ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a tetrahydronaphthalene ring; a dihydroindene ring; a tetrahydromethanonaphthalene ring; or a tetrahydroethanonaphthalene ring.
  • E1 and E2 are the same as or different from each other, and are each independently selected from the following structures.
  • the rings having the following structure are unsubstituted or substituted with R1 or R2.
  • Y 3 is O; S; Si(Ra6) (Ra7); or N(Ra8),
  • Y 4 is O; S; Si(Ra6) (Ra7); C(Ra6) (Ra7); or N(Ra8), and
  • Ra6 to Ra8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring.
  • E1 and E2 are the same as or different from each other, and are each independently a benzene ring; a cyclopentene ring; or a cyclohexene ring.
  • Ra1 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.
  • Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.
  • Ra1 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.
  • R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; or a group represented by the following Formula 3-A, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.
  • R4 and R4 are bonded to adjacent R1 or R2 to form a substituted or unsubstituted ring while being a substituted or unsubstituted cycloalkyl group.
  • R4 and R5 are the same as or different from each other, and are ach independently a substituted or unsubstituted C3-C30 cycloalkyl group; or a group represented by the following Formula 3-A, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.
  • R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cyclohexyl group; or a substituted or unsubstituted adamantyl group; or a group represented by the following Formula 3-A, or are bonded to adjacent R1 or R2 to form a substituted or unsubstituted ring.
  • R4 and R5 are the same as or different from each other, and are bonded to adjacent R1 or R2 to form a ring which is unsubstituted or substituted with a methyl group, while being each independently a cyclohexyl group which is unsubstituted or substituted with a methyl group.
  • R4 and R5 are the same as or different from each other, and are bonded to adjacent R1 or R2 to form a ring which is unsubstituted or substituted with R31, while being each independently a group represented by the following Formula 3-A.
  • R4 and R5 are a group represented by the following Formula 3-A.
  • R31 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,
  • r31 is an integer from 0 to 5, and when r31 is 2 or higher, R31's are the same as or different from each other, and
  • r31 when r31 is 2 or higher, a plurality of R31's are the same as or different from each other.
  • R31 may be bonded to adjacent R1 or R2 to form a ring.
  • R31 is linked to the ortho position with respect to nitrogen (N) while being a substituent other than hydrogen.
  • a substituent other than hydrogen (R31 of a halogen group, a cyano group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, a heterocyclic group, a cycloalkyl group, an alkylsilyl group, an arylsilyl group, an arylalkyl group, an alkylamine group, an arylamine group, a heteroarylamine group, and the like) is linked to one or two of the positions represented by a dotted line, which is the ortho position.
  • a substituent may be further linked to or a ring may be formed at the meta or para position with respect to nitrogen (N).
  • R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsub
  • R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C60 arylsilyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heterocyclic group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C6-C60 arylamine group; or a substituted or unsubstituted heteroarylamine group, or are bonded to an adjacent substitu
  • R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C10 alkyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C6-C30 aryl group or a substituent to which two or more groups selected from the above group are linked; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a
  • R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group which is unsubstituted or substituted with deuterium, a halogen group, or a C6-C30 aryl group; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; a C6-C30 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkoxy group, a C9
  • R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a fluoro group; a cyano group; a methyl group which is unsubstituted or substituted with deuterium; an ethyl group; an isopropyl group which is unsubstituted or substituted with deuterium; a tert-butyl group which is unsubstituted or substituted with deuterium; an isopropyl group substituted with a phenyl group and deuterium; a cyclohexyl group; an adamantyl group; a trimethylsilyl group; a triphenylsilyl group; a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, an isopropyl group, a tert-butyl group, CD
  • R1 to R3 and R31 are bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hetero ring; or a substituted or unsubstituted aliphatic hetero ring.
  • R1 is bonded to adjacent R1 to form a substituted or unsubstituted ring.
  • R2 is bonded to adjacent R2 to form a substituted or unsubstituted ring.
  • R3 is bonded to adjacent R3 to form a substituted or unsubstituted ring.
  • R31 is bonded to adjacent R31 to form a substituted or unsubstituted ring.
  • aliphatic hydrocarbon ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other may become a C5-C20 aliphatic hydrocarbon ring.
  • the aliphatic hydrocarbon ring may be a cyclohexene ring; a cyclopentene ring; a bicyclo[2.2.1]heptene ring; or a bicyclo[2.2.2]octene ring, and the ring is unsubstituted or substituted with a methyl group.
  • an aromatic hydrocarbon ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other may become a C6-C20 aromatic hydrocarbon ring.
  • the aromatic hydrocarbon ring may be an indene ring; or a spiro[indene-fluorene]ring, and the ring is unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.
  • an aromatic hetero ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other may be a C5-C20 aromatic hetero ring including one or more of 0, S, Si, and N.
  • the aromatic hetero ring may be a furan ring; a dihydrofuran ring; a benzofuran ring; a naphthofuran ring; a thiophene ring; a dihydrothiophene ring; a benzothiophene ring; a naphthofuran ring; an indole ring; a benzoindole ring; a silole ring; a benzosilole ring; or a naphthosilole ring, and the ring is unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.
  • two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's are bonded to each other to form one ring of Cy1 to Cy4 to be described below.
  • * is a carbon that participates in the formation of a ring among R1 to R3, R6, and R7,
  • Y10 is O; S; Si(Ra3) (Ra4); or N(Ra5),
  • Y11 is O; S; Si(Ra3) (Ra4); C(Ra3) (Ra4); or N(Ra5),
  • R41 to R44 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring,
  • p6 is an integer from 1 to 3
  • r41 is an integer from 0 to 10
  • r42 is an integer from 0 to 4
  • r43 is an integer from 0 to 2
  • r44 is an integer from 0 to 4 and when r41 to r44 are each 2 or higher, substituents in the parenthesis are the same as or different from each other.
  • a plurality of R41's are the same as or different from each other.
  • a plurality of R42's are the same as or different from each other.
  • a plurality of R43's are the same as or different from each other.
  • a plurality of R44's are the same as or different from each other.
  • * is a position in which a substituent is fused with Formula 2.
  • p6 is 1 or 2.
  • R41 to R43 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.
  • R41 to R43 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, and are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group; or a C2-C20 hetero ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.
  • R41 to R43 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group which is unsubstituted or substituted with deuterium; an isopropyl group; a tert-butyl group; or a phenyl group.
  • R41 is bonded to R41 to make a form in which a Cy1 ring is a double ring (a bicycloalkyl ring or a bicycloalkene ring), such as a bridgehead, or a fused ring.
  • a Cy1 ring is a double ring (a bicycloalkyl ring or a bicycloalkene ring), such as a bridgehead, or a fused ring.
  • the Cy1 is a bicyclo[2.2.2]octene ring; or a bicyclo[2.2.1]heptene ring, and the ring is unsubstituted or substituted with R41.
  • R42 is bonded to adjacent R42 to form a substituted or unsubstituted aliphatic hydrocarbon ring.
  • R42 is bonded to adjacent R42 to form a C5-C30 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, or a C1-C10 alkyl group substituted with deuterium.
  • R42 is bonded to adjacent R42 to form a C5-C20 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group substituted with deuterium.
  • R43 is bonded to adjacent R43 to form a substituted or unsubstituted C5-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C30 aromatic hetero ring; or a substituted or unsubstituted C2-C30 aliphatic hydrocarbon ring.
  • R43 is bonded to adjacent R43 to form an indene ring; a benzene ring; a naphthalene ring; a cyclopentene ring; a cyclohexene ring; a tetrahydronaphthalene ring; a bicyclo[2.2.2]octene ring; a bicyclo[2.2.1]heptene ring; a benzofuran ring; a benzothiophene ring; a benzosilole ring; or an indole ring, and the ring is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C6 alkyl group, and a C6-C20 aryl group or a substituent to which two or more groups selected from the above group are linked.
  • R1 to R3 and R31 may be applied to R44.
  • R44 is bonded to adjacent R44 to form a substituted or unsubstituted hydrocarbon ring.
  • R44 is bonded to adjacent R44 to form a benzene ring which is unsubstituted or substituted with R1 to R3.
  • Ra3 to Ra5 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.
  • Ra3 and Ra4 are the same as or different from each other, and are each independently a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, or are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.
  • Ra3 and Ra4 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, or are bonded to each other to form a fluorene ring which is unsubstituted or substituted with a methyl group, an isopropyl group, or a tert-butyl group.
  • Ra5 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.
  • Ra5 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.
  • Ra5 is a phenyl group which is unsubstituted or substituted with deuterium, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.
  • Y10 is O; S; Si(Ra3) (Ra4); or N(Ra5).
  • Cy1 is one selected from the following structures.
  • Cy2 is one selected from the following structures, and Y10, R42, and r42 are the same as those described above.
  • p7 is 1 to 3
  • r421 is an integer from 0 to 10
  • R42's are the same as or different from each other.
  • Cy3 is one selected from the following structures.
  • Y11 is the same as that described above,
  • R431 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
  • r431 is an integer from 0 to 2
  • r432 is an integer from 0 to 4
  • r433 is an integer from 0 to 6
  • R431's are the same as or different from each other.
  • R431 is the same except that R431 forms a ring in the above-described definition of R43.
  • R43 is hydrogen; deuterium; a methyl group; an isopropyl group; a tert-butyl group; or a phenyl group.
  • the heterocyclic group of R1 to R3 and R6 includes one or more of N, O, S, and Si as a heteroatom.
  • the O-containing heterocyclic group of R1 to R3 and R6 may be a benzofuran group; a dibenzofuran group; or a naphthobenzofuran group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.
  • the S-containing heterocyclic group of R1 to R3 and R6 may be a benzothiophene group; a dibenzothiophene group; or a naphthobenzothiophene group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.
  • the Si-containing heterocyclic group of R1 to R3 and R6 may be a benzosilole group; a dibenzosilole group; or a naphthobenzosilole group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.
  • the N-containing heterocyclic group of R1 to R3 and R6 is represented by a substituted or unsubstituted pyridyl group; or one of the following Formulae 2-A-1 to 2-A-6.
  • Y1 is C or Si
  • p1 is 0 or 1
  • Y6 and Y7 are the same as or different from each other, and are each independently O; S; C(T26) (T27); or Si (T26) (T27),
  • T11 to T16 and T20 to T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring
  • Cy5 is an aliphatic hydrocarbon ring
  • Cy6 is an aromatic hydrocarbon ring
  • t28 is an integer from 0 to 10
  • t29 is an integer from 0 to 10
  • substituents in the parenthesis are the same as or different from each other.
  • Y6 is O; or S.
  • Y6 is C(T26) (T27); or Si(T26) (T27).
  • Y6 is C(T26) (T27).
  • Y7's are the same as or different from each other, and are each independently O; S; or C(T26) (T27).
  • t28 is an integer from 0 to 6, and when t28 is 2 or higher, a plurality of T28's are the same as or different from each other.
  • t29 is an integer 0 to 10, and when t29 is 2 or higher, a plurality of T29's are the same as or different from each other.
  • T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkylsilyl group; or a substituted or unsubstituted arylsilyl group, or are bonded to an adjacent substituent to form a ring.
  • T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C1-C30 alkylsilyl group; or a substituted or unsubstituted C6-C60 arylsilyl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.
  • T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group; or a C1-C30 alkylsilyl group, or are bonded to an adjacent substituent to form a C6-C30 aromatic hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.
  • T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a methyl group which is unsubstituted or substituted with deuterium; an isopropyl group; a tert-butyl group; a phenyl group which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group; or a trimethylsilyl group, or are bonded to an adjacent substituent to form a benzene ring which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group.
  • T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or are bonded to each other to form a substituted or unsubstituted C5-C20 hydrocarbon ring.
  • T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; or a methyl group, or are bonded to each other to form a fluorene ring; or a dibenzosilole ring which is unsubstituted or substituted with a tert-butyl group, while being a phenyl group which is unsubstituted or substituted with a tert-butyl group.
  • Y1 is C.
  • Y1 is Si.
  • a site including Y1 is a direct bond.
  • T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C1-C30 alkylsilyl group.
  • T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium; or a substituted or unsubstituted C1-C18 alkylsilyl group.
  • T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group; a phenyl group; or a trimethylsilyl group.
  • T26 and T27 are each a methyl group.
  • T20 to T27 are each a methyl group.
  • T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.
  • T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium.
  • T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a tert-butyl group; or a phenyl group.
  • T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; or a tert-butyl group.
  • T29 is bonded to adjacent T29 to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • T29 is bonded to adjacent T29 to form a benzene ring.
  • T28 is hydrogen; deuterium; a tert-butyl group; or a phenyl group.
  • T28 is hydrogen; deuterium; or a tert-butyl group.
  • T28 is hydrogen; or deuterium.
  • T29 is hydrogen; or deuterium.
  • Cy5 is a C5-C20 aliphatic hydrocarbon ring.
  • Cy5 is a cyclopentane ring; a cyclohexane ring; or a cycloheptane ring.
  • Cy5 is a cyclohexane ring.
  • Cy6 is a C6-C20 aromatic hydrocarbon ring.
  • Cy6 is a benzene ring; or a naphthalene ring.
  • Cy6 is a benzene ring.
  • T17 to T19 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and at least one of T17 to T19 is a substituted or unsubstituted aryl group.
  • T17 to T19 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, and at least one of T17 to T19 is a substituted or unsubstituted C6-C30 aryl group.
  • T17 to T19 are the same as or different from each other, and are each independently a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium, and at least one of T17 to T19 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.
  • one of T17 to T19 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, and two of T17 to T19 are a C1-C6 alkyl group which is unsubstituted or substituted with deuterium.
  • T17 to T19 are the same as or different from each other, and are each independently a C1-C6 alkyl group; or a C6-C20 aryl group, and at least one of T17 to T19 is a C6-C20 aryl group.
  • T17 is a substituted or unsubstituted aryl group
  • T18 is a substituted or unsubstituted alkyl group
  • T19 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • T17 to T19 are the same as or different from each other, and are each independently a methyl group which is unsubstituted or substituted with deuterium; or a phenyl group which is unsubstituted or substituted with deuterium, and at least one of T17 to T19 is a phenyl group which is unsubstituted or substituted with deuterium.
  • one of T17 to T19 is a phenyl group which is unsubstituted or substituted with deuterium, and two of T17 to T19 are a methyl group which is unsubstituted or substituted with deuterium.
  • T17 to T19 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, and at least one of T17 to T19 is a phenyl group.
  • one of T17 to T19 is a phenyl group, and the other two are a methyl group.
  • Formula 2 includes one or more aliphatic hydrocarbon rings.
  • an aliphatic hydrocarbon ring may be included in one or more of A1 to A3, E1, and E2, R1 to R5 may be bonded to an adjacent substituent to form an aliphatic hydrocarbon ring, or R4 or R5 may be an aryl group in which an aliphatic hydrocarbon ring is fused.
  • the aliphatic hydrocarbon ring may be specifically a cyclopentene ring substituted with a methyl group, or a cyclohexene ring substituted with a methyl group.
  • Formula 2 is asymmetric with respect to a center line.
  • the center line is a line penetrating B of a mother nucleus structure and a benzene ring at the bottom. That is, in the following structure, the left and right substituents or structures are different with respect to the dotted line.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • the case where Formula 2 includes a tert-butyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-butyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-butyl group.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • the case where Formula 2 includes a tert-amyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-amyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-amyl group.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • the case where Formula 2 includes a tert-butyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-butyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-butyl group.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • the case where Formula 2 includes a tert-amyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-amyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-amyl group.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • Formulae 1-1 to 1-3 include one or more hydrogens.
  • Formula 2 when Formula 2 includes four or more tert-butyl groups, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.
  • Formula 2 when Formula 2 includes four or more tert-amyl groups, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.
  • R1 to R3 are a tert-butyl group and R4 and R5 are a phenyl group substituted with a tert-butyl group
  • one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.
  • R1 and R2 are a tert-butyl group
  • R4 and R5 are a phenyl group substituted with a tert-butyl group
  • R3 is a diphenylamine group or a carbazole group
  • one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.
  • Formula 2 excludes compounds of Group Z1.
  • the compound represented by Formula 2 is any one selected from the following compounds.
  • the compounds of Formulae 1-1 to 1-3 may be prepared as in the following Reaction Schemes 1 to 6, and the compound of Formula 2 may be prepared as in the following Reaction Scheme 7.
  • the following Reaction Schemes 1 to 7 describe synthesis procedures of partial compounds corresponding to Formulae 1-1 to 1-3 and 2 of the present application, but various compounds corresponding to Formulae 1-1 to 1-3 and 2 of the present application may be synthesized using the synthesis procedures as in the following Reaction Schemes 1 to 7, a substituent may be bonded by methods known in the art, and the type and position of substituent and the number of substituents may be changed according to the technology known in the art.
  • the organic light emitting device of the present specification may be manufactured by typical methods and materials for manufacturing an organic light emitting device, except that a light emitting layer is formed using one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2.
  • a light emitting layer including one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 may be formed as an organic material layer by not only a vacuum deposition method, but also a solution application method.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, a spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present specification may also be composed of a structure including the light emitting layer, but may be composed of a structure further including an additional organic material layer.
  • the additional organic material layer may be one or more layers of a hole injection layer, a hole transport layer, a layer which simultaneously transports and injects holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which simultaneously transports and injects electrons, and a hole blocking layer.
  • the structure of the organic light emitting device is not limited thereto, and may include a fewer or greater number of organic material layers.
  • the light emitting layer includes one or more of the compounds represented by any one of Formulae 1-1 to 1-3 as a host, and includes the compound represented by Formula 2 as a dopant.
  • the light emitting layer includes one of the compounds represented by any one of Formulae 1-1 to 1-3 as a host.
  • the light emitting layer includes two of the compounds represented by any one of Formulae 1-1 to 1-3 as a host.
  • one of the compounds represented by any one of Formulae 1-1 to 1-3 is referred to as a first host, and the other compound is referred to as a second host.
  • the weight ratio of the first host and the second host is 1:9 to 9:1, preferably 3:7 to 7:3.
  • a dopant in the light emitting layer may be included in an amount of 0.1 part by weight to 50 parts by weight, preferably 1 part by weight to 30 parts by weight, and more preferably 1 part by weight to 10 parts by weight, based on 100 parts by weight of the host. Within the above range, energy transfer from the host to the dopant occurs efficiently.
  • the maximum light emission peak of the light emitting layer including one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 is present within a range from 400 nm to 500 nm. That is, the light emitting layer is a blue light emitting layer.
  • the structure of the organic light emitting device of the present specification may have a structure as illustrated in FIGS. 1 and 2 , but is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which a positive electrode 2 , a light emitting layer 3 , an electron transporting layer 8 , and a negative electrode 4 are sequentially stacked on a substrate 1 .
  • the light emitting layer 3 may include one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2.
  • FIG. 2 exemplifies a structure of an organic light emitting device in which a positive electrode 2 , a hole injection layer 5 , a hole transport layer 6 , an electron blocking layer 7 , a light emitting layer 3 , an electron transport layer 8 , an electron injection layer 9 , and a negative electrode 4 are sequentially stacked on a substrate 1 .
  • the light emitting layer 3 may include one or more of the compounds represented by any one of Formulae 1-1 and the compound represented by Formula 2.
  • the organic light emitting device may be manufactured by depositing a metal or a metal oxide having conductivity, or an alloy thereof on a substrate to form a positive electrode, forming an organic material layer including the first organic material layer and the second organic material layer described above thereon, and then depositing a material, which may be used as a negative electrode, thereon, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic electronic device may also be made by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.
  • the organic material layer may also have a multi-layered structure further including a hole injection layer, a hole transport layer, a layer which simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which simultaneously injects and transports electrons, a hole blocking layer, and the like.
  • the organic material layer may be manufactured to include a fewer number of layers by a method such as a solvent process, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method instead of a deposition method, using various polymer materials.
  • the positive electrode is an electrode which injects holes, and as a positive electrode material, materials having a high work function are usually preferred so as to facilitate the injection of holes into an organic material layer.
  • the positive electrode material which may be used in the present invention include: a metal, such as vanadium, chromium, copper, zinc, and gold, or an alloy thereof; a metal oxide, 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; a conductive polymer, 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 negative electrode is an electrode which injects electrons, and as a negative electrode material, materials having a low work function are usually preferred so as to facilitate the injection of electrons into an organic material layer.
  • the negative electrode material include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multi-layer structured material, such as LiF/Al or LiO 2 /Al; and the like, but are not limited thereto.
  • the hole injection layer is a layer serving to facilitate the injection of holes from the positive electrode to the light emitting layer, and may have a single-layered or multi-layered structure.
  • a hole injection material is a material which may proficiently receive holes from a positive electrode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the neighboring organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
  • a hole injection layer has a multi-layered structure of two or more layers, and each layer includes a material different from each other.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a hole transport material is suitably a material having high hole mobility which may receive holes from a positive electrode or a hole injection layer and transfer the holes to a light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
  • a hole transport layer material and/or a hole injection layer material known in the art may be used as the layer which simultaneously transports and injects holes.
  • an electron transport layer material and/or an electron injection layer material known in the art may be used as the layer which simultaneously transports and injects electrons.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • materials known in the art may be used.
  • the light emitting layer may emit red, green, or blue light, and may be composed of a phosphorescent material or a fluorescent material.
  • the light emitting material is a material which may accept holes and electrons from a hole transport layer and an electron transport layer, respectively, and combine the holes and the electrons to emit light in a visible ray region, and is preferably a material having high quantum efficiency for fluorescence or phosphorescence.
  • Alq 3 8-hydroxy-quinoline aluminum complexes
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • benzoxazole-based, benzthiazole-based and benzimidazole-based compounds poly(p-phenylenevinylene) (PPV)-based polymers
  • spiro compounds polyfluorene, lubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include fused aromatic ring derivatives, or hetero ring-containing compounds, and the like.
  • examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • examples of the hetero ring-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples thereof are not limited thereto.
  • a phosphorescent material such as bis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr), or octaethylporphyrin platinum (PtOEP), or a fluorescent material such as tris(8-hydroxyquinolino)aluminum (Alq 3 ) as a light emitting dopant, but the light emitting dopant is not limited thereto.
  • PIQIr(acac) bis(1-phenylquinoline)acetylacetonate iridium
  • PQIr(acac) bis(1-phenylquinoline)acetylacetonate iridium
  • PtOEP octaethylporphyrin
  • the light emitting layer emits green light
  • a phosphorescent material such as fac tris(2-phenylpyridine)iridium (Ir(ppy) 3 ), or a fluorescent material such as tris(8-hydroxyquinolino)aluminum (Alq 3 ), as the light emitting dopant, but the light emitting dopant is not limited thereto.
  • the light emitting layer emits blue light
  • a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic
  • a fluorescent material such as spiro-DPVBi, spiro-6P, distyryl benzene (DSB), distyryl arylene (DSA), a PFO-based polymer or a PPV-based polymer
  • the light emitting dopant is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer serves to facilitate the transport of electrons, and has a single-layered or multi-layered structure.
  • An electron transport material is suitably a material having high electron mobility which may proficiently accept electrons from a negative electrode and transfer the electrons to a light emitting layer. Specific examples thereof include: A1 complexes of 8-hydroxyquinoline; complexes including Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto.
  • an electron transport layer has a multi-layered structure of two or more layers, and each layer includes a material different from each other.
  • the electron injection layer serves to facilitate the injection of electrons.
  • An electron injection material is preferably a compound which has a capability of transporting electrons, an effect of injecting electrons from a negative electrode, and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, and is also excellent in the ability to form a thin film.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compounds 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-naphtholato) aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a dual emission type according to the material to be used.
  • Compound BH-2-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-([1,1′-biphenyl]-3-yl)-10-bromoanthracene was changed into 9-bromo-10-(4-(naphthalen-2-yl)phenyl)anthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed into dibenzo[b,d]furan-3-ylboronic acid.
  • MS: [M+H]+ 547
  • Compound BH-33 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-34 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-35 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-35-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid.
  • MS: [M+H]+ 526
  • Compound BH-36 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-35-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-38 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl-2,3,5,6-d4)-boronic acid.
  • MS: [M+H]+ 526
  • Compound BH-40 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid.
  • MS: [M+H]+ 526
  • Compound BH-41 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-42 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-43 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-44 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 533
  • Compound BH-47 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-47-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid.
  • MS: [M+H]+ 453
  • Compound BH-48 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-[4-(1-naphthalenyl)phenyl-2,3,5,6-d4]-boronic acid.
  • MS: [M+H]+ 526
  • Compound BH-49 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-1-yl)phenyl-2,3,5,6-d4)-boronic acid.
  • MS: [M+H]+ 526
  • Compound BH-50 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-2-yl)phenyl)-boronic acid.
  • MS: [M+H]+ 522
  • Compound BH-51 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-2-yl)phenyl)-boronic acid.
  • MS: [M+H]+ 522
  • Compound BH-57-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid.
  • MS: [M+H]+ 314
  • Compound BH-57 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-57-b, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl)-boronic acid.
  • MS: [M+H]+ 515
  • BD-2-b was obtained from BD-2-a and 1-([1,1′-biphenyl]-2-yl)-5-tert-butyl-N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-1H-indole-2-amine in the same manner as in
  • BD-17-b was obtained from BD-17-a and N-(4-tert-butylphenyl)-4,4,6,6-tetramethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-3-amine in the same manner as in
  • BD-18-b (30.47 g, 56.8 mmol), 4-(tert-butyl)aniline (8.48 g, 56.8 mmol), Pd(Pt-Bu 3 ) 2 (0.58 g, 1.1 mmol), and NaOt-Bu (10.92 g, 113.7 mmol) were dissolved in toluene (284 ml) and stirred while being refluxed.
  • the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO 4 , filtered, concentrated, and purified with column chromatography to obtain BD-18-c (26.55 g, yield 72%).
  • BD-19-b was obtained from BD-19-a and 1-bromo-3,5-dichlorobenzene in the same manner as in Synthesis Example
  • BD-20-a was obtained from BD-14-a and 4-(tert-butyl)-2-methylaniline in the same manner as in Synthesis Example
  • BD-20-b was obtained from BD-20-a and 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan in the same manner as in Synthesis Example ⁇ 77-d>.
  • BD-21-b was obtained from BD-21-a and 4 ′,5-di-tert-butyl-[1,1′-biphenyl]-2-amine in the same manner as in

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WO2020054676A1 (ja) * 2018-09-10 2020-03-19 学校法人関西学院 有機電界発光素子
KR20190127529A (ko) * 2018-12-19 2019-11-13 머티어리얼사이언스 주식회사 유기전계발광소자

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WO2021107745A1 (ko) 2021-06-03
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