CN111936506B

CN111936506B - Compound and organic light-emitting element comprising same

Info

Publication number: CN111936506B
Application number: CN201980023345.XA
Authority: CN
Inventors: 金京嬉; 洪玩杓; 琴水井; 徐尚德
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-11-02
Filing date: 2019-11-01
Publication date: 2023-11-07
Anticipated expiration: 2039-11-01
Also published as: CN111936506A; WO2020091506A1; KR102290022B1; KR20200050887A

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light-emitting element comprising same

Technical Field

The present specification relates to a compound and an organic light emitting device including the same.

The present application claims priority from korean patent application No. 10-2018-0133639, filed to the korean patent office on 11/02 of 2018, the entire contents of which are incorporated herein.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.

There is a continuing need to develop new materials for use in organic light emitting devices as described above.

Disclosure of Invention

Technical problem

The present specification provides compounds and organic light emitting devices comprising the same.

Solution to the problem

The present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

l1 and L2 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

x1 and X2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or substituents are combined with each other to form a substituted or unsubstituted ring,

x3 and X4 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

DR1 and DR2 are the same or different from each other, each independently is a substituted or unsubstituted aryl group containing deuterium,

R1 to R6 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

m and n1 to n4 are the same or different from each other and are each independently 0 or 1,

r1 is an integer of 0 to 5, and when R1 is 2 or more, R1 are the same or different from each other,

r2 is an integer of 0 to 3, and when R2 is 2 or more, R2 are the same or different from each other,

r3 is an integer of 0 to 6, and when R3 is 2 or more, R3 are the same or different from each other,

r4 is an integer of 0 to 5, and when R4 is 2 or more, R4 are the same or different from each other,

r5 is an integer of 0 to 5, and when R5 is 2 or more, R5 are the same or different from each other,

r6 is an integer of 0 to 6, and when R6 is 2 or more, R6 is the same or different from each other.

In addition, the present specification provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.

Effects of the invention

The compound according to an embodiment of the present specification is used for an organic light emitting device, so that a driving voltage of the organic light emitting device can be reduced, and light efficiency can be improved. In addition, the life characteristics of the device can be improved by utilizing the thermal stability of the compound.

Drawings

Fig. 1 to 3 illustrate examples of an organic light emitting device according to an embodiment of the present specification.

[ description of the symbols ]

101: substrate board

102: anode

103: hole injection layer

104: hole transport layer

105: electron blocking layer

106: light-emitting layer

107: electron transport layer

108: electron injection layer

110: cathode electrode

Detailed Description

The present specification will be described in more detail below.

The compound represented by the above chemical formula 1 has a long life and high efficiency characteristics when used as a dopant for a light emitting layer of an organic light emitting device as a structure having an aryl group containing deuterium and a benzonaphthalenyl amine group containing silyl group in a (benzo) fluorene ring.

The compound represented by the above chemical formula 1 contains at least one deuterium. The chemical nature of the compound is almost unchanged when hydrogen is replaced by deuterium. However, the atomic weight of deuterium is twice that of hydrogen, and thus the physical properties of deuterated compounds may vary. As an example, the compound substituted with deuterium becomes lower in vibrational level. The deuterium-substituted compound can prevent reduction of the quantum efficiency caused by reduction of van der Waals force between molecules or collision due to vibration between molecules. In addition, the C-D bond may improve the stability of the compound. Accordingly, the compound represented by chemical formula 1 may improve efficiency and lifetime of the device by including deuterium.

In the present specification, examples of substituents are described below, but are not limited thereto.

In the present description of the invention,refers to the location of the connection.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen groups, nitrile groups, alkyl groups, cycloalkyl groups, amine groups, silyl groups, phosphine oxide groups, aryl groups, and heteroaryl groups, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.

In the present specification, the connection of 2 or more substituents means that hydrogen of any substituent is connected to other substituents. For example, isopropyl group may be linked to phenyl group to formIs a substituent of (a).

In this specification, 3 substituent linkages include not only linkage in which (substituent 1) to (substituent 2) to (substituent 3) are continuous but also linkage in which (substituent 1) and (substituent 2) are linked.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 30 carbon atoms, 3 to 20 carbon atoms, 3 to 10 carbon atoms, or 3 to 6 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, or the like, but is not limited thereto.

In the present specification, silyl groups are substituents containing Si and having the above Si atom directly bonded as a radical, represented by-SiR ₂₀₁ R ₂₀₂ R ₂₀₃ R represents ₂₀₁ To R ₂₀₃ Each of which may be the same or different from the other, may be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but are not limited thereto.

In the present specification, aryl means a 1-valent group of an aromatic hydrocarbon or an aromatic hydrocarbon derivative having 1-valent. In the present specification, an aromatic hydrocarbon means a compound having pi electrons completely conjugated and including a planar ring, and a group derived from an aromatic hydrocarbon means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed in an aromatic hydrocarbon. In the present specification, an aryl group includes a 1-valent group formed by connecting 2 or more aromatic hydrocarbons or aromatic hydrocarbon derivatives. The aryl group is not particularly limited, but is preferably an aryl group having 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, perylenyl, A group, a fluorenyl group, etc., but is not limited thereto.

In the present specification, a fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

In this specification, when the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which substituents of five-membered rings of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The above-mentioned substituted fluorenyl group includes, but is not limited to, 9 '-spirobifluorene, spiro [ cyclopentane-1, 9' -fluorene ], spiro [ benzo [ c ] fluorene-7, 9-fluorene ], and the like.

In this specification, the heteroaryl group contains 1 or more of N, O, S, si and Se as hetero atoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl (phtalazine), pteridinyl (pteridine), pyridopyrimidinyl (pyridopyrimidine), pyridopyrazinyl (pyrazino pyrazine), isoquinolinyl, indolyl, pyridoindolyl (pyridoindoxyl), indenopyrimidinyl (5H-indeno pyrimidine), carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline (phenanthrinyl), thiazolyl, iso->Azolyl, (-) -and (II) radicals>Diazolyl, thiadiazolyl, and the like, but is not limited thereto.

In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.

In the present specification, arylene means a group having two bonding positions in an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.

In the present specification, heteroarylene refers to a group having two binding sites in heteroaryl, i.e., a 2-valent group. They may be suitable for the above description of heteroaryl groups, except that each is a 2-valent group.

In this specification, an "adjacent" group refers to a substituent substituted on an atom directly bonded to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups, except for the 1-valent groups.

In the present specification, the aromatic ring may be a single ring or multiple rings, and may be selected from the above examples of aryl groups, except for 1.

In this specification, a heterocyclic ring contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The heterocycle may be a single ring or a multiple ring, may be an aromatic, aliphatic, or an aromatic and aliphatic condensed ring, and may be selected from the examples of heteroaryl groups, except for not being 1-valent.

In the present specification, me means-CH ₃ I.e. methyl.

The following describes in detail the compound represented by the above chemical formula 1.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, each independently being a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 2 to 20 carbon atoms. The above arylene or heteroarylene group is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted fluorenylene group.

In one embodiment of the present description, L1 and L2 are the same or different from each other, each independently being a direct bond, or phenylene.

In one embodiment of the present description, L1 and L2 are directly bonded.

In one embodiment of the present description, L1 and L2 are identical to each other.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are combined with each other to form a substituted or unsubstituted five-membered or six-membered ring.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or are combined with each other to form a substituted or unsubstituted five-membered or six-membered ring.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, and each is independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aromatic hydrocarbon ring having 6 to 20 carbon atoms, which are bonded to each other.

In an embodiment of the present specification, X1 and X2 are the same or different from each other, and each is independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a fluorene ring formed by combining with each other.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, each independently is a methyl group, or a phenyl group, or are phenyl groups while being bonded to each other to form a fluorene ring.

In one embodiment of the present description, X1 and X2 are each methyl.

In one embodiment of the present description, X1 and X2 are each phenyl.

In one embodiment of the present disclosure, X1 is methyl and X2 is phenyl.

In one embodiment of the present disclosure, X1 is phenyl and X2 is methyl.

In one embodiment of the present disclosure, X1 and X2 are each phenyl and combine with each other to form a fluorene ring.

The compound represented by the above chemical formula 1 contains a silyl group substituted with X3 or X4. The benzofuranyl group is substituted with a silyl group, and thus the luminous efficiency of the device is increased and the lifetime characteristics are excellent.

In one embodiment of the present specification, X3 and X4 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

In one embodiment of the present description, 3X 3 are the same or different from each other.

In one embodiment of the present description, 3X 4 are the same or different from each other.

In one embodiment of the present description, 2X 3 are identical to each other and the remaining 1X 3 are different.

In one embodiment of the present description, 2X 4 are identical to each other and the remaining 1X 4 are different.

In one embodiment of the present description, 3X 3 are identical to each other.

In one embodiment of the present description, 3X 4 are identical to each other.

In one embodiment of the present specification, X3 and X4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, X3 and X4 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, X3 and X4 are the same or different from each other, and are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, X3 and X4 are the same or different from each other and are each independently hydrogen, deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, or fluorenyl.

In one embodiment of the present description, X3 and X4 are the same or different from each other and are each independently methyl, or phenyl.

In one embodiment of the present description, X3 and X4 are identical to each other.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently are aryl groups comprising deuterium and substituted or unsubstituted.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently is an aryl group having 6 to 30 carbon atoms which contains deuterium and is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently is an aryl group having 6 to 20 carbon atoms which contains deuterium and is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In an embodiment of the present specification, DR1 and DR2 are the same or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted with deuterium and an alkyl group having 1 to 6 carbon atoms.

In an embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group, and the above DR1 and DR2 are substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms containing deuterium.

In an embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently is a phenyl group substituted with deuterium, a phenyl group substituted with deuterium and t-butyl group, or a biphenyl group substituted with deuterium.

In one embodiment of the present specification, DR1 and DR2 are phenyl groups substituted with deuterium.

In an embodiment of the present specification, DR1 and DR2 are identical to each other.

In the present specification, the substitution of N% of hydrogen of a substituent with deuterium means that N% of the total number of hydrogen that can be substituted excluding the position where the substituent is bonded to the parent structure is substituted with deuterium (D). For example, substitution of 20% of the hydrogens of the phenyl group with deuterium means that 1 of the hydrogens of the phenyl group, which are 20% of the 5 hydrogens that can be substituted, are substituted with deuterium (D). Substitution of 33% of the hydrogen of the biphenyl with deuterium means substitution with 3 deuterium.

In one embodiment of the present disclosure, more than 40% of the hydrogens of DR1 and DR2 are replaced with deuterium. In another embodiment, more than 60% are substituted with deuterium. In another embodiment, more than 80% are substituted with deuterium. In another embodiment, more than 90% are substituted with deuterium. In another embodiment, 100% is substituted with deuterium.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms substituted with deuterium at least 40%.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms substituted with deuterium at least 60%.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms substituted with deuterium at least 80%.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms substituted with deuterium at least 90%.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently is an aryl group having 6 to 20 carbon atoms substituted with 100% deuterium.

In one embodiment of the present specification, DR1 and DR2 are the same or different from each other, each independently being a phenyl group substituted with 100% deuterium, or a biphenyl group substituted with 100% deuterium.

In one embodiment of the present description, DR1 and DR2 are phenyl groups substituted with 100% deuterium.

In one embodiment of the present specification, DR1 and DR2 contain alkyl groups as substituents in addition to deuterium.

In one embodiment of the present specification, DR1 and DR2 contain an alkyl group having 1 to 6 carbon atoms as a substituent in addition to deuterium.

In one embodiment of the present specification, DR1 and DR2 contain methyl, ethyl, propyl, isopropyl, or tert-butyl as substituents in addition to deuterium.

In one embodiment of the present specification, R1 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, R1 to R6 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R6 are the same or different from each other, and each is independently hydrogen or deuterium.

In one embodiment of the present description, R1 to R6 are hydrogen.

In one embodiment of the present description, m is 0 or 1.

In an embodiment of the present specification, n1 to n4 are the same or different from each other, and each is independently 0 or 1.

In one embodiment of the present description, n1+n2 has a value of 1 or 2.

In one embodiment of the present description, n3+n4 has a value of 1 or 2.

In one embodiment of the present description, n1+n2 has a value of 1.

In one embodiment of the present description, n3+n4 has a value of 1.

In one embodiment of the present description, n1+n2 has a value of 1 or 2, and n3+n4 has a value of 1 or 2.

In one embodiment of the present description, the value of n1+n2 and the value of n3+n4 are equal.

In one embodiment of the present specification, the above chemical formula 1

Identical to each other.

In one embodiment of the present specification, the above chemical formula 1Identical to each other.

In one embodiment of the present specification, the above chemical formula 1Are the same or different from each other, and are each independently selected from the following structures.

In the above structures, X5 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

In one embodiment of the present description, 3X 5 are the same or different from each other.

In one embodiment of the present description, 2X 5 are the same and the remaining 1X 5 are different.

In one embodiment of the present description, 3X 5 are identical to each other.

In one embodiment of the present description, X5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present description, X5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, X5 is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, X5 is hydrogen, deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, or fluorenyl.

In one embodiment of the present description, X5 is methyl, or phenyl.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2.

[ chemical formula 2]

In the above-mentioned chemical formula 2,

the definitions of L1, L2, X1 to X4, DR1, DR2, R1 to R6, m, n1 to n4, and R1 to R6 are the same as those in chemical formula 1.

In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-4.

[ chemical formula 2-1]

[ chemical formula 2-2]

[ chemical formulas 2-3]

[ chemical formulas 2-4]

In the above chemical formulas 2-1 to 2-4,

l1, L2, X1 to X4, DR1, DR2, R1 to R6, R1 to R6 and n1 to n4 are as defined in chemical formula 1,

r11 is an integer of 0 to 3, and when R11 is 2 or more, R1 is the same or different.

In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-12.

[ chemical formula 3-1]

[ chemical formula 3-2]

[ chemical formula 3-3]

[ chemical formulas 3-4]

[ chemical formulas 3-5]

[ chemical formulas 3-6]

[ chemical formulas 3-7]

[ chemical formulas 3-8]

[ chemical formulas 3-9]

[ chemical formulas 3-10]

[ chemical formulas 3-11]

[ chemical formulas 3-12]

In the above chemical formulas 3-1 to 3-12,

In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 4-1 to 4-4.

[ chemical formula 4-1]

[ chemical formula 4-2]

[ chemical formula 4-3]

[ chemical formula 4-4]

In the above chemical formulas 4-1 to 4-4,

the definitions of L1, L2, X1 to X4, DR1, DR2, R1 to R6, m, and n1 to n4 are the same as those in chemical formula 1.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.

/>

The compound according to an embodiment of the present specification can be produced by a production method described below. Substituents may be added or removed as necessary, and the positions of the substituents may be changed. The starting materials, the reaction conditions, and the like may be modified based on techniques known in the art.

For example, the compound represented by the above chemical formula 1 can produce a nucleation structure as in the following reaction formula 1. Substituents may be combined according to methods known in the art, and the kinds, positions or number of substituents may be changed according to techniques known in the art. The substituent may be bonded as in the following formula 1, but is not limited thereto.

[ general formula 1]

In the above formula 1, the definitions of L1, L2, R1 to R6, m, X1 to X4, and R1 to R6 are the same as those in the above formula 1. In the above general formula, only DR1 and DR2 are described as phenyl groups substituted with deuterium, but if an amine group substituted with an aryl group substituted with deuterium is used, a compound in which DR1 and DR2 are aryl groups substituted with deuterium can be obtained.

The present specification provides an organic light emitting device comprising the above-mentioned compound.

The present specification provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.

In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.

In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.

In the present specification, the term "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target region. The size of the "layers" is not limited, and the respective "layers" may be the same or different in size. In one embodiment, the size of the "layer" may be equal to the entire device, may correspond to the size of a particular functional area, or may be as small as a single sub-pixel (sub-pixel).

In the present specification, the inclusion of a specific a substance in the B layer means that i) a case where 1 or more a substances are included in the B layer of one layer, and ii) a case where the B layer is composed of 1 or more layers and a substances are included in 1 or more layers in the B layer of the plurality of layers are all included.

In the present specification, the meaning that a specific substance a is contained in C layers or D layers includes i) 1 or more layers contained in C layers of 1 or more, or ii) 1 or more layers contained in D layers of 1 or more, or ii) C layers of 1 or more and D layers of 1 or more, respectively.

The organic light emitting device according to the present specification may include an additional organic layer in addition to the above-described light emitting layer.

The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like may be provided. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula H.

[ chemical formula H ]

In the above-mentioned chemical formula H,

l21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

R21 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms containing N, O or S.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; arylene having 6 to 20 carbon atoms; or a heteroarylene group having 2 to 20 carbon atoms which contains N, O or S. The above arylene or heteroarylene group is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. In another embodiment, the above "substituted or unsubstituted" means substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms, or does not have any substituent.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted thienyl group of 2 valency.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, phenylene, naphthylene, or a 2-valent thienyl group.

In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently is a direct bond, phenylene, or naphthylene.

In one embodiment of the present description, L21 and L22 are direct bonds.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with Y1, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with Y1.

In an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with Y1, or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with Y1.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently is a monocyclic to pentacyclic aryl group substituted or unsubstituted by Y1, or a monocyclic to pentacyclic heteroaryl group substituted or unsubstituted by Y1.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently is a monocyclic to tetracyclic aryl group substituted or unsubstituted with Y1, or a monocyclic to tetracyclic heteroaryl group substituted or unsubstituted with Y1.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by Y1, a biphenyl group substituted or unsubstituted by Y1, a terphenyl group substituted or unsubstituted by Y1, a naphthyl group substituted or unsubstituted by Y1, an anthryl group substituted or unsubstituted by Y1, a phenanthryl group substituted or unsubstituted by Y1, a fluorenyl group substituted or unsubstituted by Y1, a benzofluorenyl group substituted or unsubstituted by Y1, a furyl group substituted or unsubstituted by Y1, a thienyl group substituted or unsubstituted by Y1, a carbazolyl group substituted or unsubstituted by Y1, a dibenzofuranyl group substituted or unsubstituted by Y1, a naphthobenzofuranyl group substituted or unsubstituted by Y1, a dibenzothiophenyl group substituted or unsubstituted by Y1, a naphthobenzothienyl group substituted or unsubstituted by Y1, a naphthothiophenyl group substituted or unsubstituted by Y1, a pyridine substituted or unsubstituted by Y1, a pyrimidine substituted or unsubstituted by Y1, a quinoline substituted or unsubstituted by Y1, a 1-substituted or a quinoline substituted or unsubstituted by a 1.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted by Y1, a biphenyl group substituted or unsubstituted by Y1, a naphthyl group substituted or unsubstituted by Y1, an anthryl group, a phenanthryl group, a phenacyl group, a thienyl group substituted or unsubstituted by Y1, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, a pyridyl group, an isoquinolyl group, or an indolo [3,2,1-jk ] carbazolyl group.

In an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium, a dibenzofuranyl group substituted or unsubstituted with deuterium, a dibenzothienyl group substituted or unsubstituted with deuterium, or a naphthobenzofuranyl group substituted or unsubstituted with deuterium.

In an embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, a 1-naphthyl group substituted or unsubstituted with deuterium, a 2-naphthyl group substituted or unsubstituted with deuterium, or a dibenzofuranyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group.

In one embodiment of the present description, ar1 is a substituted or unsubstituted aryl group and Ar2 is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Y1 is deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Y1 is deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is deuterium, a halogen group, a nitrile group, a methyl group, a cyclohexyl group, a trimethylsilyl group, or a phenyl group.

In one embodiment of the present specification, Y1 is deuterium, fluoro, nitrile, methyl, cyclohexyl, or trimethylsilyl.

In one embodiment of the present specification, R21 to R28 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, R21 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R21 to R28 are the same or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present description, R21 to R28 are hydrogen.

In one embodiment of the present disclosure, R21 to R28 are deuterium.

In one embodiment of the present specification, R21 and R23 to R28 are the same or different from each other, each independently is hydrogen or deuterium, and R27 is a group represented by L23-Ar 3.

In one embodiment of the present specification, R21 and R23 to R28 are hydrogen, and R27 is a group represented by L23-Ar 3.

In one embodiment of the present specification, R21 and R23 to R28 are deuterium, and R27 is a group represented by L23-Ar 3.

The definitions of L23 and Ar3 are the same as those in the chemical formula H-1 described later.

In one embodiment of the present specification, the compound represented by the above formula H is any one selected from the following compounds.

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In one embodiment of the present specification, the above formula H is represented by the following formula H-1.

[ chemical formula H-1]

In the above-mentioned chemical formula H-1,

l21, L22, R21, R23 to R28, ar1 and Ar2 are as defined in the formula H,

l23 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, L23 is the same as the definition of L21 and L22 described above.

In one embodiment of the present specification, ar3 is the same as Ar1 and Ar2 described above.

In one embodiment of the present specification, ar3 is phenyl, biphenyl, naphthyl, anthryl, phenanthryl, dibenzofuranyl, naphthobenzofuranyl, pyridinyl, or isoquinolinyl substituted with deuterium.

In one embodiment of the present specification, ar3 is phenyl substituted or unsubstituted with deuterium, 1-naphthyl substituted or unsubstituted with deuterium, 2-naphthyl substituted or unsubstituted with deuterium, or dibenzofuranyl substituted or unsubstituted with deuterium.

In one embodiment of the present description, L23 is a direct bond, phenylene, naphthylene, or a 2-valent thienyl group.

In one embodiment of the present disclosure, L23 is a direct bond.

In one embodiment of the present specification, the compound represented by the above formula H-1 is any one selected from the following compounds.

/>

In one embodiment of the present specification, when the compound represented by the above formula H is substituted with deuterium, it is substituted with deuterium by 30% or more. In another embodiment, the structure of formula H above is substituted with deuterium by 40% or more. In another embodiment, the structure of formula H above is substituted with deuterium by 60% or more. In another embodiment, the structure of formula H above is substituted with deuterium by 80% or more. In another embodiment, the structure of formula H above is 100% substituted with deuterium.

In one embodiment of the present specification, when the compound represented by the above formula H-1 is substituted with deuterium, it is substituted with deuterium by 30% or more. In another embodiment, the structure of formula H-1 above is substituted with deuterium by more than 40%. In another embodiment, the structure of formula H-1 above is substituted with deuterium by 60% or more. In another embodiment, the structure of formula H-1 above is more than 80% substituted with deuterium. In another embodiment, the structure of formula H-1 above is 100% substituted with deuterium.

An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including a compound represented by the above chemical formula 1 as a dopant of the light emitting layer and a compound represented by the above chemical formula H as a host of the light emitting layer.

In one embodiment of the present specification, the content of the compound represented by the above chemical formula 1 is 0.01 to 30 parts by weight, 0.1 to 20 parts by weight, or 0.5 to 10 parts by weight based on 100 parts by weight of the compound represented by the above chemical formula H.

In one embodiment of the present specification, the light-emitting layer may be formed of a compound represented by the formula HOne step comprises a host substance. In this case, the host material (mixed host compound) further contained includes an aromatic condensed ring derivative, a heterocyclic compound or the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include dibenzofuran derivatives and trapezoidal furan compoundsPyrimidine derivatives, etc., but are not limited thereto.

The mixing ratio of the compound represented by the above chemical formula H and the above mixed host compound is 95:5 to 5:95, more preferably 30:70 to 70:30.

In one embodiment of the present specification, the mixed host compound is a compound represented by the chemical formula H.

In one embodiment of the present specification, the host of the light-emitting layer includes 2 or more compounds represented by the chemical formula H.

In one embodiment of the present specification, the host of the light emitting layer includes 2 compounds represented by the chemical formula H.

In one embodiment of the present specification, the light emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H is blue.

An organic light emitting device according to an embodiment of the present specification includes 2 or more light emitting layers, and at least one of the 2 or more light emitting layers includes a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula H. The light emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H is blue, and the light emitting layer not including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H may include a blue, red, or green light emitting compound known in the art.

In an embodiment of the present disclosure, the organic layer includes a hole injection layer or a hole transport layer.

In an embodiment of the present disclosure, the organic layer includes an electron injection layer or an electron transport layer.

In an embodiment of the present disclosure, the organic layer includes an electron blocking layer.

In an embodiment of the present disclosure, the organic layer includes a hole blocking layer.

In an embodiment of the present specification, the organic light emitting device further includes 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In an embodiment of the present specification, the organic light emitting device includes: a first electrode; a second electrode provided opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and an organic layer having 2 or more layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

In one embodiment of the present specification, the 2 or more organic layers may be selected from 2 or more layers among a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that performs hole transport and hole injection simultaneously, and an electron blocking layer.

In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.

In one embodiment of the present disclosure, the first electrode is a cathode, and the second electrode is an anode.

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to an embodiment of the present specification is illustrated in fig. 1 to 3. The above-described fig. 1 to 3 illustrate an organic light emitting device, and are not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. The compound represented by the above chemical formula 1 is contained in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer.

Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. According to an embodiment of the present specification, the compound represented by chemical formula 1 described above is included in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer. According to another embodiment, the compound represented by chemical formula 1 above is contained in a hole injection layer or a hole transport layer.

Fig. 3 illustrates a structure of an organic light-emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, and a cathode 110 are sequentially stacked on a substrate 101. According to an embodiment of the present specification, the compound represented by chemical formula 1 described above is included in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer. According to another embodiment, the compound represented by the above chemical formula 1 is contained in a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, or an electron injection layer.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the light emitting layer includes the above compound, i.e., the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H.

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

In addition, the compound represented by the above chemical formula 1 or the compound represented by the above chemical formula H may be used not only in the vacuum vapor deposition method but also in the solution coating method to form the organic layer in the production of the organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. For example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium Metals such as lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO ₂ And/or Al, but is not limited thereto.

The organic light emitting device according to the present specification may include an additional light emitting layer other than the light emitting layer including the compound represented by the above chemical formula 1 or the compound represented by the above chemical formula H. The additional light emitting layer may comprise a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include dibenzofuran derivatives and trapezoidal furan compounds Pyrimidine derivatives, etc., but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene having an arylamine group,Bisindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.

The hole injection layer is a layer that receives holes from the electrode. The hole injection substance is preferably the following: a substance having a hole transporting ability, an effect of receiving holes from the anode, and an excellent hole injecting effect for the light emitting layer or the light emitting material. Further, a substance which can prevent migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital ) of the hole injecting substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; hexanitrile hexaazatriphenylene organic compounds; quinacridone (quinacridone) is an organic substance; perylene (perylene) based organic compounds; polythiophene-based conductive polymers such as anthraquinone and polyaniline are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring them to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting material is a material that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a material having high mobility to electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ The complex of (a) is not limited to, but is an organic radical compound, a hydroxyflavone-metal complex, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, suitable cathode materials are the usual materials having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and aluminum or silver layers are associated in each case.

The electron beamThe in-layer is a layer that receives electrons from the electrode. The electron injection material is preferably the following: a substance having an excellent electron-transporting ability, an effect of receiving electrons from the second electrode, and an excellent electron-injecting effect to the light-emitting layer or the light-emitting material. Further, it is preferable that excitons generated in the light-emitting layer are prevented from migrating to the hole injection layer, and that the thin film forming ability is excellent. Specifically fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).

The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device. The known material can be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs hole injection and hole transport at the same time.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the electron injection layer. Specifically, there are Diazole derivatives or triazole derivatives, phenanthroline derivativesOrganisms, aluminum complexes (aluminum complexes), and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

Modes for carrying out the invention

In the following, examples, comparative examples, and the like are described in detail for the purpose of specifically describing the present specification. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. Examples and comparative examples of the present description are provided to more fully illustrate the present description to those skilled in the art.

Synthesis example 1

Under nitrogen atmosphere, 5.0g of intermediate A-1-a, 1.3g of amine A-1-b (phenyl-d 5-amine, benzen-d 5-amine), 2.0g of sodium tert-butoxide]After dissolution in toluene (130 ml), 0.14g of Bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) palladium (0)]Heated at 120℃and stirred for 10 hours. At the end of the reaction, the reaction solution was cooled to room temperature, and water and NH were added ₄ Cl solution (aq. NH) ₄ Cl) and separating the solution, and then performing MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by column chromatography (toluene/hexane) to give 4.2g of intermediate A-1 (yield 80%, mass (Mass) [ M+]＝387)。

After 3.8g of intermediate 1-1, 4.2g of intermediate A-1, 1.6g of sodium t-butoxide were dissolved in toluene (100 ml) under nitrogen atmosphere, 0.11g of bis (tri-t-butylphosphine) palladium (0) was added, and the mixture was heated at 120℃and stirred for 12 hours. At the end of the reaction, the reaction mixture was cooled to room temperature, and thenWater and NH ₄ Cl solution (aq. NH) ₄ Cl) and separating the solution, and then performing MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 6.5g of Compound 1 (yield 63%, mass [ M+)]＝964)。

Synthesis example 2

2.4g of intermediate A-2 was obtained (yield 76%, mass [ M+ ] =387) by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-2-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

In the synthesis of compound 1 of synthesis example 1, 4.2g of compound 2 (yield 70%, mass [ m+ ] =964) was obtained by the same method as the synthesis of compound 1 except that 2.4g of a-2 was used instead of a-1.

Synthesis example 3

18g of 7-hydroxy-2-naphthylboronic acid (7-hydroxymaphthalen-2-yl) carboxylic acid, 20g of 2-bromo-5-chlorophenyl-2-propanol (2- (2-bromoo-5-chlorophenyl) propane-2-ol) and 33g of potassium carbonate are dissolved in 400ml of 1, 4-di-ethylene carbonate under a nitrogen atmosphereAfter alkane and 100ml of water, 1.9g of Pd (PPh ₃ ) ₄ Stirring is carried out for 10 hours. At the end of the reaction, the reaction solution was cooled and NH was added ₄ Cl solution (aq. NH) ₄ Cl) and extracted with ethyl acetate, followed by MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was subjected to reduced pressureThe organic solvent was removed to give 20g of intermediate 3-a (yield 79%, mass [ M+)]＝313)。

20g of intermediate 3-a obtained without further purification was dissolved in chloroform and cooled to 0℃and then 12mL of methanesulfonic acid was slowly added dropwise. The reaction solution was heated at 40℃and stirred for 4 hours. Cooling the reaction solution to room temperature, adding water for extraction, collecting only the organic layer, adding NaHCO ₃ Solution (aq. NaHCO) ₃ ) Neutralization is performed. After extraction of the organic solution, mgSO was performed ₄ (anhydrous) treatment and filtration. The filtered solution was depressurized to remove the organic solvent and recrystallized (CHCl) ₃ Hexane) to give 13g of intermediate 3-b (yield 69%, mass [ M ] ]＝295)。

Under nitrogen, 13g of intermediate 3-b, 15g of potassium carbonate, 8.4ml of perfluorobutane sulfonyl fluoride [ perfluorobutanesulfonyl floride ] were charged]And a 300ml flask of Dimethylformamide (DMF) were stirred at room temperature for 1 hour. After the completion of the reaction, water was added and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in toluene and then NH was added ₄ Cl solution (aq. NH) ₄ Cl) is extracted, mgSO is performed ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (ethyl acetate: hexane) to obtain 18g of intermediate 3-c (yield 72%, mass [ M+)]＝577)。

2.2g of intermediate A-3 was obtained (yield: 70%, mass [ M+ ] =387) by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-3-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthetic example 1.

1.6g of intermediate 3-c, 2.1g of amine A-3, 1.8g of potassium phosphate [ potassium phosphate ] under a nitrogen atmosphere]After dissolving in toluene (25 ml), 28mg of bis (tri-t-butylphosphine) palladium (0) was added thereto, and the mixture was heated at 120℃and stirred for 20 hours. At the end of the reaction, the reaction solution was cooled to room temperature, and water and NH were added ₄ Cl solution (aq. NH) ₄ Cl) and separating the solution, and then performing MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (hexane/toluene), whereby 1.8g of Compound 3 was obtained (yield 64%, mass [ M+)]＝1014)。

Synthesis example 4

In the synthesis of intermediate 3-a of synthesis example 3, 9.2g of intermediate 4-a (yield 73%, mass [ m+ ] =313) was obtained by the same method as the synthesis of intermediate 3-a except that 9.1g of 6-hydroxy-2-naphthylboronic acid (6-hydroxynaphalen-2-yl) was used instead of 7-hydroxy-1-naphthylboronic acid.

The synthesis of intermediate 3-b of synthesis example 3 was performed in the same manner as the synthesis of intermediate 3-b except that 9.2g of 4-a was used instead of 3-a, thereby obtaining 6.8g of intermediate 4-b (yield 78%, mass [ m+ ] =295).

10g of intermediate 4-c (yield 76%, mass [ M+ ] =577) was obtained by the same method as the synthesis method of intermediate 3-c, except that 6.8g of 4-b was used instead of 3-b in the synthesis of intermediate 3-c of synthesis example 3.

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2.3g of intermediate A-4 (yield 73%, mass [ M+ ] =387) was obtained by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-4-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

In the synthesis of compound 3 of synthesis example 3, 2.0g of compound 4 was obtained (yield 67%, mass [ m+ ] =1014) by the same method as the synthesis of compound 3, except that 1.7g of 4-c was used instead of intermediate 3-c and 2.3g of a-4 was used instead of a-3.

Synthesis example 5

The synthesis of intermediate 3-a of synthesis example 3 was performed in the same manner as the synthesis of intermediate 3-a except that 9.1g of 7-hydroxy-3-naphthylboronic acid (7-hydroxynaphalen-3-yl) was used instead of 7-hydroxy-1-naphthylboronic acid, thereby obtaining 8.8g of intermediate 5-a (yield 70%, mass [ m+ ] =313).

The synthesis of intermediate 3-b of synthesis example 3 was performed in the same manner as the synthesis of intermediate 3-b except that 8.8g of 5-a was used instead of 3-a, thereby obtaining 6.5g of intermediate 5-b (yield 78%, mass [ m+ ] =295).

8.7g of intermediate 5-c (yield 69%, mass [ M+ ] =577) was obtained by the same method as the synthesis method of intermediate 3-c, except that 6.5g of 5-b was used instead of 3-b in the synthesis of intermediate 3-c of synthesis example 3.

2.1g of intermediate A-5 was obtained (yield 67%, mass [ M+ ] =387) by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-5-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

In the synthesis of compound 3 of synthesis example 3, 1.9g of compound 5 was obtained (yield 68%, mass [ m+ ] =1014) by the same method as the synthesis of compound 3, except that 1.6g of 5-c was used instead of intermediate 3-c and 2.1g of a-5 was used instead of a-3.

Synthesis example 6

The synthesis of intermediate 3-a of synthesis example 3 was performed in the same manner as the synthesis of intermediate 3-a except that 4.5g of 6-hydroxy-3-naphthylboronic acid (6-hydroxynaphalen-3-yl) was used instead of 7-hydroxy-1-naphthylboronic acid, thereby obtaining 5.1g of intermediate 6-a (yield 81%, mass [ m+ ] =313).

3.7g of intermediate 6-b (yield 77%, mass [ M+ ] =295) was obtained by producing the intermediate by the same method as the synthesis method of intermediate 3-b except that 5.1g of 6-a was used instead of 3-a in the synthesis of intermediate 3-b of synthesis example 3.

In the synthesis of intermediate 3-c of synthesis example 3, 5.6g of intermediate 6-c was obtained (yield 78%, mass [ M+ ] =577) by the same method as the synthesis of intermediate 3-c, except that 3.7g of 6-b was used instead of 3-b.

In the synthesis of compound 3 of synthesis example 3, 1.8g of compound 6 was obtained (yield 68%, mass [ m+ ] =1014) by the same method as the synthesis of compound 3, except that 1.5g of 6-c was used instead of intermediate 3-c and 2.0g of a-2 was used instead of a-3.

Synthesis example 7

In the synthesis of intermediate 3-a of synthesis example 3, the same procedure as the synthesis of intermediate 3-a was repeated except that 3.0g of 7-hydroxy-3-naphthylboronic acid was used in place of 7-hydroxy-1-naphthylboronic acid and 5.0g of (2-bromo-5-chlorophenyl) benzhydrol [ (2-bromol-5-chlorophenylmethanol ] was used in place of 2-bromo-5-chlorophenyl-2-propanol, whereby 4.3g of intermediate 7-a was obtained (yield 74%, mass [ m+ ] =437).

2.8g of intermediate 7-b (yield 68%, mass [ M+ ] =419) was obtained by the same method as the synthesis method of intermediate 3-b, except that 4.3g of 7-a was used instead of 3-a in the synthesis of intermediate 3-b in synthesis example 3.

3.6g of intermediate 7-c (yield 77%, mass [ M+ ] =702) was obtained by the same method as the synthesis method of intermediate 3-c, except that 2.8g of 7-b was used instead of 3-b in the synthesis of intermediate 3-c of synthesis example 3.

4.1g of intermediate A-6 was obtained (yield 79%, mass [ M+ ] =449) by the same method as the synthesis method of intermediate A-1, except that 5.0g of A-6-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

In the synthesis of compound 3 of synthesis example 3, 2.5g of compound 7 was obtained (yield 69%, mass [ m+ ] =1262) by the same method as the synthesis of compound 3, except that 2.0g of 7-c was used instead of intermediate 3-c and 2.2g of a-6 was used instead of a-3.

Synthesis example 8

In the synthesis of intermediate 3-a of synthesis example 3, the same procedure as that of the synthesis of intermediate 3-a was repeated except that 18g of 7-hydroxy-3-naphthylboronic acid was used in place of 7-hydroxy-1-naphthylboronic acid and 20g of methyl2-bromo-5-chlorobenzoate [ methyl 2-bromoo-5-chlorobenzoate ] was used in place of 2-bromo-5-chlorophenyl-2-propanol, whereby 19g of intermediate 8-a was obtained (yield 76%, mass [ m+ ] =313).

A flask containing 19g of intermediate 8-a obtained without further purification, concentrated sulfuric acid (2.0 mL), acetic acid (300 mL) and chloroform (140 mL) was heated and stirred at 80℃for 4 hours. The reaction solution was cooled to room temperature, and then the solvent was removed under reduced pressure, and dissolved again in toluene. Addition of NaHCO ₃ Solution (aq. NaHCO) ₃ ) After separation of the liquid, mgSO was carried out ₄ (anhydrous) treatment and filtration. The filtered solvent was removed under reduced pressure, and purified by recrystallization (ethyl acetate/hexane) to give 11g of intermediate 8-b (yield 65%, mass [ M+)]＝281)。

To a solution of 9.1g of 2-bromo-1,1'-biphenyl [2-bromo-1,1' -biphenyl ] in 400ml of tetrahydrofuran (THF anhydrous) cooled to-78 ℃]Slowly adding n-butyllithium [ n-butyl llithium ] dropwise into the flask of (C)](16 mL,2.5M in hexane) and then stirred at the same temperature for one hour. After confirming the completion of the lithium-halogen substitution reaction, 11g of intermediate 8-b was added, and the temperature was slowly raised to room temperature and stirred at room temperature for 8 hours. Adding water and NH ₄ Cl solution (aq. NH) ₄ Cl) and separating the solution, and then performing MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, whereby 10g of intermediate 8-c was obtained.

In the synthesis of intermediate 3-b of synthesis example 3, 7.2g of intermediate 8-d (yield 68%, mass [ M+ ] =417) was obtained by the same method as the synthesis of intermediate 3-b, except that 10g of 8-c was used instead of 3-a.

In the synthesis of intermediate 3-c of synthesis example 3, 9.2g of intermediate 8-e (yield 76%, mass [ M+ ] =699) was obtained by the same method as the synthesis of intermediate 3-c, except that 7.2g of 8-d was used instead of 3-b.

2.2g of intermediate A-7 was obtained (yield: 70%, mass [ M+ ] =387) by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-7-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

In the synthesis of compound 3 of synthesis example 3, 3.1g of compound 8 was obtained (yield 64%, mass [ m+ ] =1136) by the same method as the synthesis of compound 3, except that 3.0g of 8-e was used instead of intermediate 3-c and 3.3g of a-7 was used instead of a-3.

Synthesis example 9

In the synthesis of intermediate 3-a of synthesis example 3, 9.8g of intermediate 9-a (yield 78%, mass [ m+ ] =313) was obtained by the same method as the synthesis of intermediate 3-a except that 9.1g of 4-hydroxy-1-naphthylboronic acid (4-hydroxynaphalen-1-yl) was used instead of 7-hydroxy-1-naphthylboronic acid.

The synthesis of intermediate 3-b of synthesis example 3 was performed in the same manner as the synthesis of intermediate 3-b except that 9.8g of 9-a was used instead of 3-a, thereby obtaining 6.8g of intermediate 9-b (yield 74%, mass [ m+ ] =295).

9.6g of intermediate 9-c (yield 73%, mass [ M+ ] =577) was obtained by the same method as the synthesis method of intermediate 3-c, except that 6.8g of 9-b was used instead of 3-b in the synthesis of intermediate 3-c in synthesis example 3.

In the synthesis of compound 3 of synthesis example 3, 2.2g of compound 9 was obtained (yield 63%, mass [ m+ ] =1014) by the same method as the synthesis of compound 3, except that 2.0g of 6-c was used instead of intermediate 3-c and 2.7g of a-4 was used instead of a-3.

Synthesis example 10

In the synthesis of intermediate 3-a of synthesis example 3, the same procedure as that of the synthesis of intermediate 3-a was repeated except that 3.6g of 4-hydroxy-1-naphthylboric acid was used in place of 7-hydroxy-1-naphthylboric acid and 5.0g of 1- (2-bromo-5-chlorophenyl) -1-phenylethanol [1- (2-bromoyl-5-chlorophenyl) -1-phenylethan-1-ol ] was used in place of 2-bromo-5-chlorophenyl-2-propanol, whereby 4.6g of intermediate 10-a was obtained (yield 77% and mass [ m+ ] =375).

3.1g of intermediate 10-b was obtained (yield: 71%, mass [ m+ ] =357) by the same method as the synthesis method of intermediate 3-b, except that 4.6g of 10-a was used instead of 3-a in the synthesis of intermediate 3-b of synthesis example 3.

In the synthesis of intermediate 3-c of synthesis example 3, 5.0g of intermediate 10-c was obtained (yield 75%, mass [ M+ ] =639) by the same method as the synthesis of intermediate 3-c, except that 3.1g of 10-b was used instead of 3-b.

In the synthesis of compound 3 of synthesis example 3, 2.1g of compound 10 was obtained (yield 62%, mass [ m+ ] =1076) by the same method as the synthesis of compound 3, except that 2.0g of 10-c was used instead of intermediate 3-c and 2.4g of a-7 was used instead of a-3.

Synthesis example 11

2.3g of intermediate A-8 (yield 74%, mass [ M+ ] =437) was obtained by the same method as the synthesis method of intermediate A-1, except that 3.0g of A-8-a was used instead of A-1-a in the synthesis of intermediate A-1 of synthesis example 1.

2.0g of compound 11 (yield 71%, mass [ m+ ] =1064) was obtained by the same method as the synthesis method of compound 1 except that 2.3g of a-8 was used instead of a-1 in the synthesis of compound 1 of synthesis example 1.

Synthesis example 12

In the synthesis of intermediate A-1 of Synthesis example 1, 4.5g of intermediate A-9 was obtained (yield 69%, mass [ M+ ] =467) by the same method as the synthesis of intermediate A-1 except that 5.2g of A-5-a was used in place of A-1-a and 2.5g of A-9-b was used in place of A-1-b.

In the synthesis of compound 3 of synthesis example 3, 3.2g of compound 12 was obtained (yield 57%, mass [ m+ ] =1174) by the same method as the synthesis of compound 3, except that 2.8g of 5-c was used instead of intermediate 3-c and 4.5g of a-9 was used instead of a-3.

Synthesis example 13

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In the synthesis of intermediate A-1 of Synthesis example 1, 2.5g of intermediate A-10 was obtained (yield: 71%, mass: M+ ] =442) by the same method as the synthesis of intermediate A-1 except that 3.0g of A-4-a was used in place of A-1-a and 1.2g of A-10-b was used in place of A-1-b.

In the synthesis of compound 3 of synthesis example 3, 2.0g of compound 13 was obtained (yield 63%, mass [ m+ ] =1124) by the same method as the synthesis of compound 3, except that 1.6g of 9-c was used instead of intermediate 3-c and 2.5g of a-10 was used instead of a-3.

Example 1

To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.

On the ITO transparent electrode thus preparedHexanitrile Hexaazabenzophenanthrene (HAT) of the following formulaAnd performing thermal vacuum evaporation to form a hole injection layer.

On the hole injection layer, 4' -bis [ N- (1-naphthyl) -N-phenylamino group of the following chemical formula as a hole transporting substance]Biphenyl (NPB)Vacuum evaporation is performed to form a hole transport layer.

Next, on the hole transport layer, [ HT-A ] is formed ]To be used forAnd vacuum evaporation is performed to form an electron blocking layer. Then, on the electron blocking layer, [ BH-2 ] is used as a light-emitting body]To->And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer.

At the same time as vapor deposition of the above-mentioned light-emitting layer, 3 wt% of compound 1 was used as a blue light-emitting dopant with respect to 100% of the total weight of the host. On the light-emitting layer, the [ TPBI]And LiQ in a weight ratio of 1:1, therebyAn electron transport layer is formed by the thickness of (a). On the first electron transport layer, will [ LiF ]]Vacuum evaporation is performed to give->An electron injection layer is formed by the thickness of (a). On the second electron transport layer, by +.>Aluminum was vapor deposited to form a cathode.

In the process, the evaporation rate of the organic matters is maintained to be 0.4 toLithium fluoride maintenance of cathode>Is kept at>Is maintained at a vacuum degree of 1×10 at the time of vapor deposition ^-7 Up to 5X 10 ^-8 The support is thus fabricated into an organic light emitting device.

Examples 2 to 17 and comparative examples 1 to 5

An organic light-emitting device was manufactured in the same manner as in example 1, except that the host and the dopant compound described in table 1 below were used as the light-emitting layer material in example 1 above.

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The organic light emitting devices fabricated according to the above examples 1 to 17 and comparative examples 1 to 5 were fabricated at 10mA/cm ² The drive voltage, efficiency and lifetime were measured at the current density of (c). For the lifetime, the time required for 97% relative to the initial luminance was measured (T97). The results are shown in table 1 below.

TABLE 1

	Main body	Dopant(s)	Luminous efficiency (Cd/A)	Life, T97 (time)
					Example 1	BH-2	Compound 1	6.11	112
Example 2	BH-2	Compound 4	6.42	120
					Example 3	BH-2	Compound 5	6.24	117
Example 4	BH-2	Compound 6	6.05	122
					Example 5	BH-2	Compound 8	6.13	126
Example 6	BH-2	Compound 9	6.3	120
					Example 7	BH-2	Compound 11	6.21	110
Example 8	BH-2	Compound 12	6.30	118
					Example 9	BH-2	Compound 13	6.32	125
Example 10	BH-1	Compound 1	6.15	114
					Example 11	BH-1	Compound 8	6.25	124
Example 12	BH-1	Compound 9	6.48	127
					Example 13	BH-1	Compound 10	6.12	122
Example 14	BH-3	Compound 9	6.35	120
					Example 15	BH-3	Compound 1	6.12	113
Example 16	BH-4	Compound 7	6.42	115
					Example 17	BH-4	Compound 9	6.5	125
Comparative example 1	BH-2	BD-1	5.21	96
					Comparative example 2	BH-2	BD-2	5.42	102
Comparative example 3	BH-1	BD-3	2.10	52
					Comparative example 4	BH-1	BD-4	2.01	48
Comparative example 5	BH-1	BD-5	1.82	36

As shown in table 1 above, it is understood that the organic light emitting devices of examples 1 to 17 including the compound of the present invention as a dopant of the light emitting layer are excellent in light emitting efficiency and/or lifetime as compared with the organic light emitting devices of comparative examples 1 to 5.

Claims

1. A compound represented by the following chemical formula 1:

Chemical formula 1

In the chemical formula 1 described above, a compound having the formula,

l1 and L2 are each independently a direct bond,

x1 and X2 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, or are each phenyl groups and are bonded to each other while forming a fluorene ring,

x3 and X4 are the same or different from each other and are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,

DR1 and DR2 are the same or different from each other and are each independently an aryl group having 6 to 20 carbon atoms substituted with deuterium or an aryl group having 6 to 20 carbon atoms substituted with deuterium and an alkyl group having 1 to 6 carbon atoms,

r1 to R6 are the same or different from each other and are each independently hydrogen or deuterium,

m and n1 to n4 are identical to or different from each other and are each independently 0 or 1, the value of n1+n2 is 1 or 2, and the value of n3+n4 is 1 or 2,

r1 is an integer of 0 to 5, and R1 is 2 or more, R1 are the same or different from each other,

r2 is an integer of 0 to 3, and R2 is 2 or more, R2 are the same or different from each other,

r3 is an integer of 0 to 6, and R3 is 2 or more, R3 are the same or different from each other,

r4 is an integer of 0 to 5, and R4 is 2 or more, R4 are the same or different from each other,

R5 is an integer of 0 to 5, and R5 is 2 or more, R5 are the same or different from each other,

r6 is an integer of 0 to 6, and R6 is 2 or more, R6 are the same or different from each other.

2. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2:

chemical formula 2

In the chemical formula 2 described above, the chemical formula,

3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-4:

chemical formula 2-1

Chemical formula 2-2

Chemical formula 2-3

Chemical formulas 2-4

In the chemical formulas 2-1 to 2-4,

l1, L2, X1 to X4, DR1, DR2, R1 to R6, R1 to R6 and n1 to n4 are as defined in chemical formula 1, and

r11 is an integer of 0 to 3, and R1 is the same or different when R11 is 2 or more.

4. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-12:

chemical formula 3-1

Chemical formula 3-2

Chemical formula 3-3

Chemical formulas 3-4

Chemical formulas 3-5

Chemical formulas 3-6

Chemical formulas 3-7

Chemical formulas 3-8

Chemical formulas 3-9

Chemical formula 3-10

Chemical formulas 3-11

Chemical formula 3-12

In the chemical formulas 3-1 to 3-12,

5. The compound of claim 1, wherein n1+n2 has a value of 1 and n3+n4 has a value of 1.

6. The compound of claim 1, wherein DR1 and DR2 are the same or different from each other and are each independently phenyl substituted with deuterium, phenyl substituted with deuterium and tert-butyl, or biphenyl substituted with deuterium.

7. The compound according to claim 1, wherein X1 and X2 are the same or different from each other and are each independently methyl, or phenyl, or are each phenyl while being bonded to each other to form a fluorene ring.

8. The compound of claim 1, wherein X3 and X4 are the same or different from each other and are each independently methyl, or phenyl.

9. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:

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10. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 9.

11. The organic light-emitting device of claim 10, wherein the organic layer comprises a light-emitting layer comprising the compound.

12. The organic light-emitting device according to claim 10, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound and a compound represented by the following chemical formula H:

chemical formula H

In the chemical formula H described above, the amino acid sequence,

ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

13. The organic light-emitting device according to claim 10, wherein the organic layer further comprises 1 layer or 2 layers or more selected from a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.